Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_coden_Cambridge 1350 _publ_contact_author_name 'Prof. Chick C. Wilson' _publ_contact_author_address ; Department of Chemistry University of Glasgow Glasgow G12 8QQ UK ; _publ_contact_author_phone 44(141)3308522 _publ_contact_author_fax 44(141)3308775 _publ_contact_author_email c.c.wilson@chem.gla.ac.uk _publ_requested_journal CrystEngComm loop_ _publ_author_name _publ_author_address 'Schmidtmann, Marc' ; Department of Chemistry University of Glasgow Glasgow G12 8QQ UK ; 'Wilson, Chick C.' ; Department of Chemistry University of Glasgow Glasgow G12 8QQ UK ; data_35lpcp3 _database_code_depnum_ccdc_archive 'CCDC 650951' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H10 Cl5 N O' _chemical_formula_weight 373.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9077(14) _cell_length_b 8.6625(17) _cell_length_c 12.910(3) _cell_angle_alpha 77.42(3) _cell_angle_beta 82.55(3) _cell_angle_gamma 88.70(3) _cell_volume 747.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.659 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.963 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8308 _exptl_absorpt_correction_T_max 0.9904 _exptl_absorpt_process_details 'fsprocess (Higashi, 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-Axis Rapid IP area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14213 _diffrn_reflns_av_R_equivalents 0.0825 _diffrn_reflns_av_sigmaI/netI 0.0718 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3392 _reflns_number_gt 2460 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2006)' _computing_cell_refinement fsprocess _computing_data_reduction fsprocess _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker AXS XP' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+18.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3392 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1445 _refine_ls_R_factor_gt 0.1185 _refine_ls_wR_factor_ref 0.3001 _refine_ls_wR_factor_gt 0.2837 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.2063(7) 0.1950(3) 0.11595(18) 0.0639(12) Uani 1 1 d . . . Cl2 Cl 0.1188(3) 0.0612(2) 0.36146(15) 0.0243(5) Uani 1 1 d . . . Cl3 Cl 0.1001(4) -0.3028(2) 0.45104(16) 0.0278(5) Uani 1 1 d . . . Cl4 Cl 0.1647(3) -0.5330(2) 0.29462(16) 0.0223(5) Uani 1 1 d . . . Cl5 Cl 0.2496(7) -0.3947(3) 0.0483(2) 0.0703(13) Uani 1 1 d . . . N1 N 0.2975(17) 0.2059(9) -0.1501(6) 0.044(2) Uani 1 1 d . . . O1 O 0.259(3) -0.0605(9) -0.0120(6) 0.131(7) Uani 1 1 d . . . H1A H 0.2605 0.0387 -0.0292 0.050 Uiso 1 1 calc R . . C1 C 0.220(2) -0.1068(11) 0.0934(8) 0.055(4) Uani 1 1 d . . . C2 C 0.1919(18) -0.0069(10) 0.1654(7) 0.036(2) Uani 1 1 d . . . C3 C 0.1528(12) -0.0656(9) 0.2737(6) 0.0201(16) Uani 1 1 d . . . C4 C 0.1450(12) -0.2279(9) 0.3161(6) 0.0184(15) Uani 1 1 d . . . C5 C 0.1741(13) -0.3300(9) 0.2451(7) 0.0221(17) Uani 1 1 d . . . C6 C 0.2112(19) -0.2700(10) 0.1368(7) 0.037(3) Uani 1 1 d . . . C7 C 0.3290(14) 0.1498(10) -0.2403(7) 0.0278(19) Uani 1 1 d . . . H7A H 0.3306 0.0385 -0.2341 0.033 Uiso 1 1 calc R . . C8 C 0.3587(12) 0.2457(10) -0.3407(6) 0.0223(16) Uani 1 1 d . . . C9 C 0.3539(12) 0.4082(9) -0.3476(6) 0.0200(16) Uani 1 1 d . . . H9A H 0.3740 0.4777 -0.4160 0.024 Uiso 1 1 calc R . . C10 C 0.3206(13) 0.4715(10) -0.2567(7) 0.0250(18) Uani 1 1 d . . . C11 C 0.2932(16) 0.3620(10) -0.1577(7) 0.032(2) Uani 1 1 d . . . H11A H 0.2707 0.4009 -0.0939 0.038 Uiso 1 1 calc R . . C12 C 0.3923(15) 0.1739(12) -0.4368(7) 0.033(2) Uani 1 1 d . . . H12A H 0.3131 0.0775 -0.4240 0.049 Uiso 1 1 calc R . . H12B H 0.5307 0.1476 -0.4501 0.049 Uiso 1 1 calc R . . H12C H 0.3549 0.2495 -0.4992 0.049 Uiso 1 1 calc R . . C13 C 0.3191(14) 0.6485(10) -0.2581(9) 0.037(2) Uani 1 1 d . . . H13A H 0.3175 0.6638 -0.1850 0.055 Uiso 1 1 calc R . . H13B H 0.2027 0.6966 -0.2875 0.055 Uiso 1 1 calc R . . H13C H 0.4363 0.6985 -0.3026 0.055 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.161(4) 0.0095(9) 0.0168(11) -0.0017(8) 0.0046(15) -0.0074(14) Cl2 0.0367(11) 0.0189(9) 0.0175(9) -0.0053(7) -0.0013(8) -0.0012(8) Cl3 0.0467(13) 0.0181(9) 0.0166(9) -0.0017(7) 0.0008(8) -0.0025(8) Cl4 0.0324(11) 0.0117(8) 0.0231(9) -0.0043(7) -0.0038(8) 0.0003(7) Cl5 0.173(4) 0.0139(10) 0.0221(12) -0.0083(9) 0.0014(17) -0.0028(16) N1 0.094(8) 0.016(4) 0.021(4) -0.003(3) -0.001(4) -0.003(4) O1 0.36(2) 0.009(3) 0.015(4) -0.003(3) -0.003(7) 0.000(7) C1 0.132(13) 0.012(4) 0.019(5) -0.003(3) -0.007(6) -0.007(6) C2 0.082(8) 0.009(4) 0.016(4) -0.002(3) -0.004(4) -0.003(4) C3 0.028(4) 0.015(4) 0.018(4) -0.006(3) 0.001(3) -0.004(3) C4 0.023(4) 0.014(3) 0.019(4) -0.004(3) -0.004(3) -0.001(3) C5 0.033(4) 0.011(3) 0.022(4) -0.004(3) -0.001(3) -0.001(3) C6 0.086(8) 0.009(4) 0.017(4) -0.006(3) -0.006(4) -0.002(4) C7 0.037(5) 0.021(4) 0.023(4) -0.001(3) 0.003(4) -0.004(4) C8 0.022(4) 0.028(4) 0.019(4) -0.007(3) -0.004(3) 0.001(3) C9 0.021(4) 0.015(3) 0.020(4) 0.006(3) -0.004(3) 0.001(3) C10 0.032(5) 0.017(4) 0.024(4) -0.003(3) 0.001(3) -0.003(3) C11 0.063(7) 0.014(4) 0.018(4) -0.007(3) 0.003(4) -0.006(4) C12 0.043(5) 0.035(5) 0.022(4) -0.013(4) 0.000(4) -0.003(4) C13 0.030(5) 0.011(4) 0.058(6) 0.003(4) 0.015(4) 0.003(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C2 1.727(8) . ? Cl2 C3 1.734(8) . ? Cl3 C4 1.711(8) . ? Cl4 C5 1.735(8) . ? Cl5 C6 1.729(9) . ? N1 C11 1.334(11) . ? N1 C7 1.346(12) . ? O1 C1 1.326(12) . ? O1 H1A 0.8400 . ? C1 C2 1.394(12) . ? C1 C6 1.403(12) . ? C2 C3 1.373(11) . ? C3 C4 1.393(10) . ? C4 C5 1.400(11) . ? C5 C6 1.373(12) . ? C7 C8 1.372(12) . ? C7 H7A 0.9500 . ? C8 C9 1.391(11) . ? C8 C12 1.495(11) . ? C9 C10 1.390(12) . ? C9 H9A 0.9500 . ? C10 C11 1.409(12) . ? C10 C13 1.529(11) . ? C11 H11A 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 N1 C7 119.0(8) . . ? C1 O1 H1A 109.5 . . ? O1 C1 C2 125.6(8) . . ? O1 C1 C6 117.4(8) . . ? C2 C1 C6 117.0(8) . . ? C3 C2 C1 121.6(8) . . ? C3 C2 Cl1 119.7(6) . . ? C1 C2 Cl1 118.7(7) . . ? C2 C3 C4 121.0(7) . . ? C2 C3 Cl2 120.6(6) . . ? C4 C3 Cl2 118.3(6) . . ? C3 C4 C5 118.2(7) . . ? C3 C4 Cl3 121.5(6) . . ? C5 C4 Cl3 120.2(6) . . ? C6 C5 C4 120.3(7) . . ? C6 C5 Cl4 120.1(6) . . ? C4 C5 Cl4 119.6(6) . . ? C5 C6 C1 121.9(8) . . ? C5 C6 Cl5 120.7(6) . . ? C1 C6 Cl5 117.3(7) . . ? N1 C7 C8 123.2(8) . . ? N1 C7 H7A 118.4 . . ? C8 C7 H7A 118.4 . . ? C7 C8 C9 117.2(8) . . ? C7 C8 C12 119.8(8) . . ? C9 C8 C12 123.0(8) . . ? C10 C9 C8 121.6(7) . . ? C10 C9 H9A 119.2 . . ? C8 C9 H9A 119.2 . . ? C9 C10 C11 116.3(7) . . ? C9 C10 C13 124.4(8) . . ? C11 C10 C13 119.2(8) . . ? N1 C11 C10 122.6(8) . . ? N1 C11 H11A 118.7 . . ? C10 C11 H11A 118.7 . . ? C8 C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C8 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1A N1 0.84 1.88 2.586(11) 141.1 . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 2.789 _refine_diff_density_min -2.035 _refine_diff_density_rms 0.222 # Attachment '2_34lpcp2_5.cif' data_34lpcp2_5 _database_code_depnum_ccdc_archive 'CCDC 650952' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H10 Cl5 N O' _chemical_formula_weight 373.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0775(9) _cell_length_b 8.3612(11) _cell_length_c 12.9536(19) _cell_angle_alpha 93.097(9) _cell_angle_beta 102.689(8) _cell_angle_gamma 100.189(7) _cell_volume 732.58(17) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1754 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 26.88 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.693 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.982 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'TWINABS V1.05 (Sheldrick, 2003)' _exptl_special_details ; non-merohedral twin ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3605 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0605 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 27.33 _reflns_number_total 3605 _reflns_number_gt 2670 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker AXS X8 Apex2' _computing_cell_refinement 'Bruker AXS SAINT V7.34A' _computing_data_reduction 'Bruker AXS SAINT V7.34A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker AXS XP' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0250P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3605 _refine_ls_number_parameters 188 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0499 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.0627 _refine_ls_wR_factor_gt 0.0591 _refine_ls_goodness_of_fit_ref 0.897 _refine_ls_restrained_S_all 0.897 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.30080(8) 0.79044(7) 0.30485(5) 0.02069(15) Uani 1 1 d . . . Cl2 Cl 0.38851(8) 0.83800(7) 0.55119(5) 0.01977(14) Uani 1 1 d . . . Cl3 Cl 0.30883(8) 0.54162(7) 0.67964(4) 0.01919(14) Uani 1 1 d . . . Cl4 Cl 0.14891(8) 0.19327(7) 0.56020(5) 0.01896(14) Uani 1 1 d . . . Cl5 Cl 0.06771(8) 0.14657(7) 0.31341(5) 0.01995(14) Uani 1 1 d . . . O1 O 0.1616(3) 0.4409(2) 0.21506(13) 0.0224(4) Uani 1 1 d . . . H1 H 0.219(4) 0.504(3) 0.190(2) 0.041(10) Uiso 1 1 d . . . C1 C 0.1981(3) 0.4701(3) 0.32095(18) 0.0156(5) Uani 1 1 d . . . C2 C 0.2655(3) 0.6237(3) 0.37599(18) 0.0146(5) Uani 1 1 d . . . C3 C 0.3011(3) 0.6461(3) 0.48598(18) 0.0136(5) Uani 1 1 d . . . C4 C 0.2658(3) 0.5128(3) 0.54330(16) 0.0135(5) Uani 1 1 d . . . C5 C 0.1946(3) 0.3588(3) 0.48986(18) 0.0133(5) Uani 1 1 d . . . C6 C 0.1605(3) 0.3377(3) 0.38061(18) 0.0145(5) Uani 1 1 d . . . C7 C 0.5240(4) 0.6845(3) 0.1051(2) 0.0287(6) Uani 1 1 d . . . H7A H 0.6005 0.6676 0.1723 0.034 Uiso 1 1 calc R . . C8 C 0.6210(3) 0.7737(3) 0.04028(19) 0.0191(5) Uani 1 1 d . . . C9 C 0.5133(3) 0.8030(3) -0.05831(19) 0.0196(5) Uani 1 1 d . . . C10 C 0.3100(4) 0.7342(3) -0.08360(19) 0.0245(6) Uani 1 1 d . . . H10A H 0.2279 0.7495 -0.1495 0.029 Uiso 1 1 calc R . . C11 C 0.2320(4) 0.6445(3) -0.0114(2) 0.0228(6) Uani 1 1 d . . . H11A H 0.0953 0.5971 -0.0306 0.027 Uiso 1 1 calc R . . C12 C 0.8401(4) 0.8405(3) 0.0761(2) 0.0401(8) Uani 1 1 d . . . H12A H 0.8919 0.8017 0.1448 0.060 Uiso 1 1 calc R . . H12B H 0.8637 0.9601 0.0834 0.060 Uiso 1 1 calc R . . H12C H 0.9069 0.8030 0.0233 0.060 Uiso 1 1 calc R . . C13 C 0.6060(4) 0.8994(3) -0.1334(2) 0.0341(7) Uani 1 1 d . . . H13A H 0.6789 1.0054 -0.0969 0.051 Uiso 1 1 calc R . . H13B H 0.5033 0.9164 -0.1938 0.051 Uiso 1 1 calc R . . H13C H 0.6971 0.8401 -0.1590 0.051 Uiso 1 1 calc R . . N1 N 0.3346(3) 0.6199(3) 0.08304(17) 0.0287(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0278(4) 0.0159(3) 0.0190(3) 0.0077(3) 0.0070(3) 0.0022(3) Cl2 0.0251(4) 0.0135(3) 0.0197(3) 0.0009(2) 0.0057(3) 0.0007(2) Cl3 0.0241(3) 0.0209(3) 0.0129(3) 0.0034(2) 0.0049(3) 0.0038(2) Cl4 0.0243(3) 0.0151(3) 0.0190(3) 0.0074(2) 0.0071(3) 0.0035(2) Cl5 0.0263(4) 0.0139(3) 0.0191(3) 0.0004(2) 0.0076(3) -0.0002(2) O1 0.0311(11) 0.0189(10) 0.0143(9) 0.0031(8) 0.0067(8) -0.0049(8) C1 0.0148(13) 0.0191(12) 0.0139(12) 0.0040(10) 0.0048(10) 0.0033(10) C2 0.0134(12) 0.0144(12) 0.0174(13) 0.0081(10) 0.0049(10) 0.0028(9) C3 0.0088(12) 0.0141(12) 0.0167(13) -0.0004(10) 0.0018(10) 0.0011(9) C4 0.0120(12) 0.0190(12) 0.0109(11) 0.0023(10) 0.0040(10) 0.0051(9) C5 0.0111(12) 0.0123(12) 0.0190(13) 0.0073(9) 0.0066(10) 0.0030(9) C6 0.0138(13) 0.0113(12) 0.0187(13) 0.0005(10) 0.0050(10) 0.0020(9) C7 0.0356(17) 0.0239(15) 0.0305(17) 0.0081(12) 0.0100(13) 0.0112(12) C8 0.0194(14) 0.0168(12) 0.0224(14) 0.0011(11) 0.0061(11) 0.0053(10) C9 0.0300(15) 0.0146(12) 0.0184(14) 0.0014(10) 0.0129(11) 0.0066(11) C10 0.0336(16) 0.0257(14) 0.0152(13) -0.0019(11) 0.0011(12) 0.0155(12) C11 0.0215(14) 0.0212(14) 0.0233(15) -0.0028(11) 0.0088(12) -0.0047(11) C12 0.0209(16) 0.0442(19) 0.052(2) -0.0010(16) 0.0009(14) 0.0095(13) C13 0.0533(19) 0.0271(15) 0.0293(17) 0.0046(13) 0.0262(14) 0.0056(13) N1 0.0395(15) 0.0217(12) 0.0248(13) 0.0030(10) 0.0100(11) 0.0026(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C2 1.724(2) . ? Cl2 C3 1.716(2) . ? Cl3 C4 1.721(2) . ? Cl4 C5 1.720(2) . ? Cl5 C6 1.724(2) . ? O1 C1 1.339(3) . ? O1 H1 0.74(3) . ? C1 C2 1.386(3) . ? C1 C6 1.404(3) . ? C2 C3 1.388(3) . ? C3 C4 1.388(3) . ? C4 C5 1.383(3) . ? C5 C6 1.378(3) . ? C7 N1 1.315(3) . ? C7 C8 1.369(3) . ? C7 H7A 0.9500 . ? C8 C9 1.394(3) . ? C8 C12 1.510(3) . ? C9 C10 1.410(3) . ? C9 C13 1.485(3) . ? C10 C11 1.378(3) . ? C10 H10A 0.9500 . ? C11 N1 1.325(3) . ? C11 H11A 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 113(2) . . ? O1 C1 C2 124.3(2) . . ? O1 C1 C6 118.3(2) . . ? C2 C1 C6 117.4(2) . . ? C1 C2 C3 121.6(2) . . ? C1 C2 Cl1 118.67(18) . . ? C3 C2 Cl1 119.72(18) . . ? C2 C3 C4 119.9(2) . . ? C2 C3 Cl2 120.11(17) . . ? C4 C3 Cl2 119.98(18) . . ? C5 C4 C3 119.47(19) . . ? C5 C4 Cl3 120.88(17) . . ? C3 C4 Cl3 119.65(18) . . ? C6 C5 C4 120.2(2) . . ? C6 C5 Cl4 120.01(18) . . ? C4 C5 Cl4 119.78(18) . . ? C5 C6 C1 121.4(2) . . ? C5 C6 Cl5 120.42(17) . . ? C1 C6 Cl5 118.16(18) . . ? N1 C7 C8 126.0(2) . . ? N1 C7 H7A 117.0 . . ? C8 C7 H7A 117.0 . . ? C7 C8 C9 118.7(2) . . ? C7 C8 C12 120.3(2) . . ? C9 C8 C12 121.0(2) . . ? C8 C9 C10 116.1(2) . . ? C8 C9 C13 122.4(2) . . ? C10 C9 C13 121.5(2) . . ? C11 C10 C9 119.1(2) . . ? C11 C10 H10A 120.5 . . ? C9 C10 H10A 120.5 . . ? N1 C11 C10 124.5(2) . . ? N1 C11 H11A 117.8 . . ? C10 C11 H11A 117.8 . . ? C8 C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C8 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C7 N1 C11 115.6(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N1 0.74(3) 1.97(3) 2.685(3) 161(3) . C11 H11A O1 0.95 2.63 3.331(3) 130.8 2_565 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.33 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.485 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.068 # Attachment '3_23lpcp.cif' data_23lpcp _database_code_depnum_ccdc_archive 'CCDC 650953' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H10 Cl5 N O' _chemical_formula_weight 373.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.3366(14) _cell_length_b 7.0801(4) _cell_length_c 19.0097(10) _cell_angle_alpha 90.00 _cell_angle_beta 125.646(2) _cell_angle_gamma 90.00 _cell_volume 2989.9(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7065 _cell_measurement_theta_min 3.07 _cell_measurement_theta_max 33.80 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.659 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 0.963 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19143 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0241 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 33.86 _reflns_number_total 5993 _reflns_number_gt 5028 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker AXS X8 Apex2' _computing_cell_refinement 'Bruker AXS SAINT V7.34A' _computing_data_reduction 'Bruker AXS SAINT V7.34A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker AXS XP' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+1.1000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5993 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0338 _refine_ls_R_factor_gt 0.0258 _refine_ls_wR_factor_ref 0.0663 _refine_ls_wR_factor_gt 0.0622 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.425104(11) 0.83806(4) 0.700606(16) 0.02010(5) Uani 1 1 d . . . Cl2 Cl 0.312878(12) 0.92301(4) 0.700725(16) 0.02027(5) Uani 1 1 d . . . Cl3 Cl 0.191835(11) 1.04290(3) 0.530573(17) 0.01937(5) Uani 1 1 d . . . Cl4 Cl 0.182161(11) 1.07235(3) 0.358658(16) 0.01934(5) Uani 1 1 d . . . Cl5 Cl 0.295087(12) 0.98805(4) 0.359585(16) 0.02177(6) Uani 1 1 d . . . O1 O 0.40103(4) 0.87765(12) 0.52619(5) 0.02025(15) Uani 1 1 d . . . H1 H 0.4245(9) 0.794(3) 0.5588(13) 0.060(6) Uiso 1 1 d . . . C1 C 0.35464(4) 0.91183(13) 0.52951(6) 0.01464(16) Uani 1 1 d . . . C2 C 0.35742(4) 0.90038(13) 0.60575(6) 0.01433(16) Uani 1 1 d . . . C3 C 0.30754(4) 0.93973(13) 0.60607(6) 0.01403(16) Uani 1 1 d . . . C4 C 0.25307(4) 0.99385(13) 0.52963(6) 0.01386(16) Uani 1 1 d . . . C5 C 0.24927(4) 1.00787(13) 0.45325(6) 0.01413(16) Uani 1 1 d . . . C6 C 0.29940(4) 0.96842(13) 0.45345(6) 0.01453(16) Uani 1 1 d . . . C7 C 0.52755(4) 0.61422(14) 0.60551(6) 0.01589(17) Uani 1 1 d . . . C8 C 0.56858(4) 0.46352(15) 0.63477(7) 0.01830(18) Uani 1 1 d . . . C9 C 0.55624(5) 0.30005(16) 0.66224(7) 0.0232(2) Uani 1 1 d . . . H9A H 0.5830 0.1957 0.6821 0.028 Uiso 1 1 calc R . . C10 C 0.50494(5) 0.28833(16) 0.66081(7) 0.0241(2) Uani 1 1 d . . . H10A H 0.4960 0.1766 0.6790 0.029 Uiso 1 1 calc R . . C11 C 0.46725(5) 0.44301(16) 0.63228(7) 0.02085(19) Uani 1 1 d . . . H11A H 0.4324 0.4367 0.6319 0.025 Uiso 1 1 calc R . . C12 C 0.53717(5) 0.79555(16) 0.57440(7) 0.0229(2) Uani 1 1 d . . . H12A H 0.5034 0.8813 0.5553 0.034 Uiso 1 1 calc R . . H12B H 0.5396 0.7695 0.5259 0.034 Uiso 1 1 calc R . . H12C H 0.5748 0.8544 0.6217 0.034 Uiso 1 1 calc R . . C13 C 0.62351(5) 0.47862(19) 0.63473(8) 0.0276(2) Uani 1 1 d . . . H13A H 0.6469 0.3616 0.6575 0.041 Uiso 1 1 calc R . . H13B H 0.6483 0.5850 0.6712 0.041 Uiso 1 1 calc R . . H13C H 0.6111 0.4991 0.5754 0.041 Uiso 1 1 calc R . . N1 N 0.47810(4) 0.60291(13) 0.60495(6) 0.01724(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.01460(10) 0.02542(12) 0.01471(10) 0.00081(9) 0.00538(8) 0.00229(8) Cl2 0.02482(12) 0.02323(12) 0.01705(11) -0.00035(9) 0.01462(10) -0.00012(9) Cl3 0.01686(10) 0.01812(10) 0.02737(13) -0.00196(9) 0.01530(10) 0.00032(8) Cl4 0.01577(10) 0.01817(10) 0.01678(11) 0.00180(8) 0.00534(9) 0.00317(8) Cl5 0.02627(12) 0.02571(12) 0.01752(11) 0.00466(9) 0.01514(10) 0.00436(9) O1 0.0180(3) 0.0234(4) 0.0246(4) 0.0059(3) 0.0154(3) 0.0053(3) C1 0.0150(4) 0.0136(4) 0.0166(4) 0.0007(3) 0.0099(3) 0.0002(3) C2 0.0131(4) 0.0140(4) 0.0137(4) 0.0000(3) 0.0066(3) 0.0002(3) C3 0.0165(4) 0.0130(4) 0.0143(4) -0.0012(3) 0.0099(3) -0.0013(3) C4 0.0131(4) 0.0121(4) 0.0177(4) -0.0014(3) 0.0097(3) -0.0007(3) C5 0.0137(4) 0.0115(4) 0.0150(4) 0.0002(3) 0.0071(3) 0.0003(3) C6 0.0175(4) 0.0134(4) 0.0146(4) 0.0009(3) 0.0104(3) 0.0004(3) C7 0.0148(4) 0.0192(4) 0.0119(4) -0.0014(3) 0.0068(3) 0.0007(3) C8 0.0151(4) 0.0218(5) 0.0149(4) -0.0045(4) 0.0070(4) 0.0024(3) C9 0.0220(5) 0.0197(5) 0.0207(5) -0.0014(4) 0.0083(4) 0.0050(4) C10 0.0268(5) 0.0193(5) 0.0227(5) 0.0027(4) 0.0125(4) 0.0003(4) C11 0.0192(4) 0.0232(5) 0.0204(5) 0.0028(4) 0.0117(4) 0.0001(4) C12 0.0234(5) 0.0242(5) 0.0221(5) 0.0032(4) 0.0139(4) -0.0006(4) C13 0.0193(5) 0.0384(6) 0.0266(6) -0.0063(5) 0.0141(4) 0.0028(4) N1 0.0155(4) 0.0199(4) 0.0155(4) 0.0014(3) 0.0086(3) 0.0018(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C2 1.7266(10) . ? Cl2 C3 1.7225(10) . ? Cl3 C4 1.7199(10) . ? Cl4 C5 1.7211(10) . ? Cl5 C6 1.7239(10) . ? O1 C1 1.3281(12) . ? O1 H1 0.83(2) . ? C1 C2 1.4087(13) . ? C1 C6 1.4096(14) . ? C2 C3 1.3951(13) . ? C3 C4 1.3976(14) . ? C4 C5 1.3975(14) . ? C5 C6 1.3965(13) . ? C7 N1 1.3479(13) . ? C7 C8 1.4067(14) . ? C7 C12 1.4994(15) . ? C8 C9 1.3897(16) . ? C8 C13 1.5058(15) . ? C9 C10 1.3891(16) . ? C9 H9A 0.9500 . ? C10 C11 1.3798(16) . ? C10 H10A 0.9500 . ? C11 N1 1.3488(14) . ? C11 H11A 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 116.1(14) . . ? O1 C1 C2 123.92(9) . . ? O1 C1 C6 119.00(9) . . ? C2 C1 C6 117.05(8) . . ? C3 C2 C1 121.75(9) . . ? C3 C2 Cl1 120.11(7) . . ? C1 C2 Cl1 118.13(7) . . ? C2 C3 C4 120.13(9) . . ? C2 C3 Cl2 120.18(7) . . ? C4 C3 Cl2 119.68(7) . . ? C5 C4 C3 119.26(8) . . ? C5 C4 Cl3 120.86(7) . . ? C3 C4 Cl3 119.88(7) . . ? C6 C5 C4 120.29(9) . . ? C6 C5 Cl4 120.17(7) . . ? C4 C5 Cl4 119.54(7) . . ? C5 C6 C1 121.51(9) . . ? C5 C6 Cl5 120.40(7) . . ? C1 C6 Cl5 118.09(7) . . ? N1 C7 C8 121.53(9) . . ? N1 C7 C12 116.95(9) . . ? C8 C7 C12 121.52(9) . . ? C9 C8 C7 117.91(9) . . ? C9 C8 C13 121.32(10) . . ? C7 C8 C13 120.76(10) . . ? C10 C9 C8 120.38(10) . . ? C10 C9 H9A 119.8 . . ? C8 C9 H9A 119.8 . . ? C11 C10 C9 118.32(10) . . ? C11 C10 H10A 120.8 . . ? C9 C10 H10A 120.8 . . ? N1 C11 C10 122.42(10) . . ? N1 C11 H11A 118.8 . . ? C10 C11 H11A 118.8 . . ? C7 C12 H12A 109.5 . . ? C7 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C7 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C7 N1 C11 119.44(9) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N1 0.83(2) 1.80(2) 2.6054(12) 163(2) . C12 H12A O1 0.98 2.52 3.3245(14) 139.5 . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 33.86 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.553 _refine_diff_density_min -0.312 _refine_diff_density_rms 0.065 # Attachment '4_26lpcp6.cif' data_26lpcp6 _database_code_depnum_ccdc_archive 'CCDC 650954' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H10 Cl5 N O' _chemical_formula_weight 373.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.4813(3) _cell_length_b 11.4515(6) _cell_length_c 12.7614(7) _cell_angle_alpha 68.164(3) _cell_angle_beta 82.613(3) _cell_angle_gamma 83.030(2) _cell_volume 735.02(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8413 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 36.25 _exptl_crystal_description 'long plate' _exptl_crystal_colour colorless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.687 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.979 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21223 _diffrn_reflns_av_R_equivalents 0.0233 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 33.73 _reflns_number_total 5864 _reflns_number_gt 4866 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker AXS X8 Apex2' _computing_cell_refinement 'Bruker AXS SAINT V7.34A' _computing_data_reduction 'Bruker AXS SAINT V7.34A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker AXS XP' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+0.1300P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5864 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0362 _refine_ls_R_factor_gt 0.0274 _refine_ls_wR_factor_ref 0.0755 _refine_ls_wR_factor_gt 0.0708 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 1.02787(5) 0.84442(2) 0.62600(2) 0.01865(6) Uani 1 1 d . . . Cl2 Cl 0.89028(5) 0.94101(2) 0.82689(2) 0.01778(6) Uani 1 1 d . . . Cl3 Cl 0.44573(5) 0.83598(3) 1.00509(2) 0.01897(6) Uani 1 1 d . . . Cl4 Cl 0.17462(5) 0.61673(2) 0.99315(2) 0.01747(6) Uani 1 1 d . . . Cl5 Cl 0.32383(5) 0.51795(2) 0.79361(2) 0.01850(6) Uani 1 1 d . . . O1 O 0.72240(16) 0.64010(7) 0.63665(7) 0.01815(15) Uani 1 1 d . . . H1 H 0.789(4) 0.6903(19) 0.5710(18) 0.053(6) Uiso 1 1 d . . . C1 C 0.66783(19) 0.68613(9) 0.71898(8) 0.01383(17) Uani 1 1 d . . . C2 C 0.79264(19) 0.78164(9) 0.72845(8) 0.01376(17) Uani 1 1 d . . . C3 C 0.72791(19) 0.82611(9) 0.81735(8) 0.01379(17) Uani 1 1 d . . . C4 C 0.53387(19) 0.77706(9) 0.89862(8) 0.01358(17) Uani 1 1 d . . . C5 C 0.41034(19) 0.68041(9) 0.89203(8) 0.01370(17) Uani 1 1 d . . . C6 C 0.47693(19) 0.63588(9) 0.80356(9) 0.01386(17) Uani 1 1 d . . . C7 C 1.06170(19) 0.68378(9) 0.38246(9) 0.01426(17) Uani 1 1 d . . . C8 C 1.0799(2) 0.69561(10) 0.26897(9) 0.01713(19) Uani 1 1 d . . . H8A H 1.2105 0.6509 0.2394 0.021 Uiso 1 1 calc R . . C9 C 0.9044(2) 0.77367(10) 0.19995(9) 0.0180(2) Uani 1 1 d . . . H9A H 0.9117 0.7815 0.1229 0.022 Uiso 1 1 calc R . . C10 C 0.7181(2) 0.84035(10) 0.24423(9) 0.01593(18) Uani 1 1 d . . . H10A H 0.5976 0.8949 0.1978 0.019 Uiso 1 1 calc R . . C11 C 0.71076(19) 0.82588(9) 0.35805(8) 0.01403(17) Uani 1 1 d . . . C12 C 1.2442(2) 0.60079(10) 0.46195(10) 0.0190(2) Uani 1 1 d . . . H12A H 1.1562 0.5515 0.5339 0.028 Uiso 1 1 calc R . . H12B H 1.3558 0.6532 0.4757 0.028 Uiso 1 1 calc R . . H12C H 1.3399 0.5434 0.4282 0.028 Uiso 1 1 calc R . . C13 C 0.5195(2) 0.89937(10) 0.41005(9) 0.0190(2) Uani 1 1 d . . . H13A H 0.5133 0.8606 0.4929 0.029 Uiso 1 1 calc R . . H13B H 0.3576 0.8986 0.3855 0.029 Uiso 1 1 calc R . . H13C H 0.5630 0.9867 0.3856 0.029 Uiso 1 1 calc R . . N1 N 0.87768(16) 0.74751(8) 0.42551(7) 0.01389(15) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.01728(12) 0.02063(12) 0.01781(11) -0.00705(9) 0.00443(9) -0.00674(9) Cl2 0.01810(12) 0.01725(11) 0.02065(12) -0.00849(9) -0.00233(9) -0.00555(9) Cl3 0.02192(13) 0.02277(12) 0.01615(11) -0.01164(9) 0.00065(9) -0.00405(9) Cl4 0.01800(12) 0.01848(11) 0.01542(11) -0.00597(9) 0.00388(9) -0.00576(9) Cl5 0.02153(13) 0.01663(11) 0.02013(12) -0.00918(9) 0.00145(9) -0.00731(9) O1 0.0245(4) 0.0172(3) 0.0142(3) -0.0079(3) 0.0029(3) -0.0046(3) C1 0.0159(4) 0.0122(4) 0.0126(4) -0.0037(3) -0.0016(3) -0.0002(3) C2 0.0134(4) 0.0134(4) 0.0134(4) -0.0036(3) 0.0003(3) -0.0028(3) C3 0.0144(4) 0.0127(4) 0.0147(4) -0.0047(3) -0.0025(3) -0.0022(3) C4 0.0150(4) 0.0141(4) 0.0124(4) -0.0055(3) -0.0017(3) -0.0009(3) C5 0.0133(4) 0.0141(4) 0.0126(4) -0.0038(3) -0.0002(3) -0.0018(3) C6 0.0154(4) 0.0121(4) 0.0144(4) -0.0047(3) -0.0012(3) -0.0027(3) C7 0.0141(4) 0.0130(4) 0.0160(4) -0.0058(3) -0.0009(3) -0.0009(3) C8 0.0166(5) 0.0187(5) 0.0171(4) -0.0090(4) 0.0016(4) 0.0002(4) C9 0.0196(5) 0.0214(5) 0.0139(4) -0.0081(4) 0.0002(4) -0.0017(4) C10 0.0154(5) 0.0170(4) 0.0153(4) -0.0058(4) -0.0021(4) -0.0006(4) C11 0.0143(4) 0.0127(4) 0.0154(4) -0.0057(3) 0.0003(3) -0.0017(3) C12 0.0185(5) 0.0181(5) 0.0206(5) -0.0075(4) -0.0051(4) 0.0024(4) C13 0.0188(5) 0.0198(5) 0.0192(5) -0.0096(4) -0.0009(4) 0.0031(4) N1 0.0146(4) 0.0135(4) 0.0135(4) -0.0053(3) 0.0000(3) -0.0012(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C2 1.7265(11) . ? Cl2 C3 1.7232(10) . ? Cl3 C4 1.7230(10) . ? Cl4 C5 1.7223(11) . ? Cl5 C6 1.7246(10) . ? O1 C1 1.3283(12) . ? O1 H1 0.88(2) . ? C1 C2 1.4071(14) . ? C1 C6 1.4088(15) . ? C2 C3 1.3981(14) . ? C3 C4 1.3965(14) . ? C4 C5 1.3987(14) . ? C5 C6 1.3947(14) . ? C7 N1 1.3524(12) . ? C7 C8 1.3950(14) . ? C7 C12 1.4987(15) . ? C8 C9 1.3869(15) . ? C8 H8A 0.9500 . ? C9 C10 1.3888(14) . ? C9 H9A 0.9500 . ? C10 C11 1.3951(14) . ? C10 H10A 0.9500 . ? C11 N1 1.3461(13) . ? C11 C13 1.5069(14) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 117.5(13) . . ? O1 C1 C2 123.88(9) . . ? O1 C1 C6 118.80(9) . . ? C2 C1 C6 117.32(9) . . ? C3 C2 C1 121.40(9) . . ? C3 C2 Cl1 120.43(8) . . ? C1 C2 Cl1 118.16(7) . . ? C4 C3 C2 120.24(9) . . ? C4 C3 Cl2 120.07(7) . . ? C2 C3 Cl2 119.69(8) . . ? C3 C4 C5 119.29(9) . . ? C3 C4 Cl3 120.36(8) . . ? C5 C4 Cl3 120.35(8) . . ? C6 C5 C4 120.16(9) . . ? C6 C5 Cl4 119.96(8) . . ? C4 C5 Cl4 119.88(7) . . ? C5 C6 C1 121.56(9) . . ? C5 C6 Cl5 120.62(8) . . ? C1 C6 Cl5 117.82(7) . . ? N1 C7 C8 121.15(9) . . ? N1 C7 C12 117.00(9) . . ? C8 C7 C12 121.85(9) . . ? C9 C8 C7 118.98(9) . . ? C9 C8 H8A 120.5 . . ? C7 C8 H8A 120.5 . . ? C8 C9 C10 119.58(9) . . ? C8 C9 H9A 120.2 . . ? C10 C9 H9A 120.2 . . ? C9 C10 C11 118.89(9) . . ? C9 C10 H10A 120.6 . . ? C11 C10 H10A 120.6 . . ? N1 C11 C10 121.34(9) . . ? N1 C11 C13 117.15(9) . . ? C10 C11 C13 121.49(9) . . ? C7 C12 H12A 109.5 . . ? C7 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C7 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 N1 C7 120.02(9) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N1 0.88(2) 1.75(2) 2.5878(12) 158.0(19) . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 33.73 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.501 _refine_diff_density_min -0.373 _refine_diff_density_rms 0.070 # Attachment '5_daum.cif' data_daum _database_code_depnum_ccdc_archive 'CCDC 650955' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H20 Cl10 N2 O2' _chemical_formula_weight 746.94 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.7761(6) _cell_length_b 14.2399(10) _cell_length_c 23.7104(17) _cell_angle_alpha 90.00 _cell_angle_beta 95.9480(10) _cell_angle_gamma 90.00 _cell_volume 2947.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9111 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 36.25 _exptl_crystal_description 'long plate' _exptl_crystal_colour colorless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.683 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 0.977 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 41576 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0283 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 33.73 _reflns_number_total 11757 _reflns_number_gt 9375 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker AXS X8 Apex2' _computing_cell_refinement 'Bruker AXS SAINT V7.34A' _computing_data_reduction 'Bruker AXS SAINT V7.34A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker AXS XP' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+0.6000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11757 _refine_ls_number_parameters 373 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0435 _refine_ls_R_factor_gt 0.0309 _refine_ls_wR_factor_ref 0.0820 _refine_ls_wR_factor_gt 0.0754 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.42640(3) 0.58497(2) 0.181073(12) 0.01720(6) Uani 1 1 d . . . Cl2 Cl 0.46449(3) 0.60646(2) 0.052391(13) 0.02063(6) Uani 1 1 d . . . Cl3 Cl 0.17647(4) 0.62800(2) -0.035961(12) 0.02175(6) Uani 1 1 d . . . Cl4 Cl -0.14999(3) 0.62753(2) 0.006024(13) 0.02080(6) Uani 1 1 d . . . Cl5 Cl -0.18530(3) 0.60470(2) 0.135227(13) 0.01918(6) Uani 1 1 d . . . Cl6 Cl -0.27629(3) 0.60684(2) 0.436499(12) 0.01753(6) Uani 1 1 d . . . Cl7 Cl -0.32143(3) 0.63999(2) 0.563459(12) 0.01876(6) Uani 1 1 d . . . Cl8 Cl -0.03855(3) 0.65118(2) 0.654118(12) 0.02230(6) Uani 1 1 d . . . Cl9 Cl 0.29177(3) 0.63913(2) 0.615888(13) 0.02116(6) Uani 1 1 d . . . Cl10 Cl 0.33414(3) 0.61154(2) 0.487501(13) 0.02052(6) Uani 1 1 d . . . O1 O 0.10461(9) 0.58530(6) 0.20702(3) 0.01534(15) Uani 1 1 d . . . O2 O 0.05152(10) 0.59847(6) 0.41365(4) 0.01829(16) Uani 1 1 d . . . H2 H 0.004(3) 0.639(2) 0.3916(13) 0.106(11) Uiso 1 1 d . . . N1 N 0.23680(11) 0.70354(7) 0.27687(4) 0.01389(17) Uani 1 1 d . . . H1 H 0.181(3) 0.653(2) 0.2473(12) 0.096(9) Uiso 1 1 d . . . N2 N -0.09087(11) 0.71191(7) 0.34266(4) 0.01450(17) Uani 1 1 d . . . C1 C 0.12152(12) 0.59529(7) 0.15340(5) 0.01308(18) Uani 1 1 d . . . C2 C 0.26632(12) 0.59653(7) 0.13217(5) 0.01348(18) Uani 1 1 d . . . C3 C 0.28403(13) 0.60599(7) 0.07461(5) 0.01444(19) Uani 1 1 d . . . C4 C 0.15530(13) 0.61539(8) 0.03507(5) 0.01510(19) Uani 1 1 d . . . C5 C 0.01000(13) 0.61493(8) 0.05416(5) 0.01470(19) Uani 1 1 d . . . C6 C -0.00627(13) 0.60495(7) 0.11173(5) 0.01405(19) Uani 1 1 d . . . C7 C 0.02757(13) 0.61275(8) 0.46740(5) 0.01465(19) Uani 1 1 d . . . C8 C -0.11891(13) 0.61914(7) 0.48609(5) 0.01419(19) Uani 1 1 d . . . C9 C -0.13960(13) 0.63195(8) 0.54318(5) 0.01485(19) Uani 1 1 d . . . C10 C -0.01285(13) 0.63755(8) 0.58359(5) 0.01541(19) Uani 1 1 d . . . C11 C 0.13426(13) 0.63139(8) 0.56636(5) 0.0156(2) Uani 1 1 d . . . C12 C 0.15373(13) 0.61954(8) 0.50910(5) 0.01520(19) Uani 1 1 d . . . C13 C 0.33255(13) 0.67674(8) 0.32214(5) 0.0154(2) Uani 1 1 d . . . C14 C 0.41121(14) 0.74477(8) 0.35557(5) 0.0189(2) Uani 1 1 d . . . H14A H 0.4779 0.7272 0.3880 0.023 Uiso 1 1 calc R . . C15 C 0.39126(14) 0.83881(9) 0.34102(5) 0.0202(2) Uani 1 1 d . . . H15A H 0.4461 0.8858 0.3631 0.024 Uiso 1 1 calc R . . C16 C 0.29157(14) 0.86422(8) 0.29432(5) 0.0179(2) Uani 1 1 d . . . H16A H 0.2779 0.9284 0.2842 0.022 Uiso 1 1 calc R . . C17 C 0.21206(13) 0.79474(8) 0.26255(5) 0.01461(19) Uani 1 1 d . . . C18 C 0.34637(15) 0.57384(8) 0.33373(5) 0.0208(2) Uani 1 1 d . . . H18A H 0.3236 0.5390 0.2982 0.031 Uiso 1 1 calc R . . H18B H 0.2737 0.5556 0.3605 0.031 Uiso 1 1 calc R . . H18C H 0.4509 0.5594 0.3501 0.031 Uiso 1 1 calc R . . C19 C 0.09868(14) 0.81462(8) 0.21236(5) 0.0191(2) Uani 1 1 d . . . H19A H 0.0074 0.7757 0.2144 0.029 Uiso 1 1 calc R . . H19B H 0.1447 0.8001 0.1775 0.029 Uiso 1 1 calc R . . H19C H 0.0697 0.8811 0.2124 0.029 Uiso 1 1 calc R . . C20 C -0.07823(13) 0.80426(8) 0.35497(5) 0.0157(2) Uani 1 1 d . . . C21 C -0.16697(15) 0.86994(8) 0.32320(5) 0.0199(2) Uani 1 1 d . . . H21A H -0.1589 0.9348 0.3323 0.024 Uiso 1 1 calc R . . C22 C -0.26776(15) 0.83944(9) 0.27787(6) 0.0222(2) Uani 1 1 d . . . H22A H -0.3292 0.8834 0.2556 0.027 Uiso 1 1 calc R . . C23 C -0.27828(14) 0.74442(8) 0.26527(5) 0.0194(2) Uani 1 1 d . . . H23A H -0.3459 0.7227 0.2341 0.023 Uiso 1 1 calc R . . C24 C -0.18832(13) 0.68139(8) 0.29889(5) 0.01531(19) Uani 1 1 d . . . C25 C 0.03308(15) 0.83180(9) 0.40474(5) 0.0216(2) Uani 1 1 d . . . H25A H 0.1287 0.7967 0.4036 0.032 Uiso 1 1 calc R . . H25B H -0.0111 0.8174 0.4400 0.032 Uiso 1 1 calc R . . H25C H 0.0542 0.8993 0.4030 0.032 Uiso 1 1 calc R . . C26 C -0.19294(15) 0.57753(8) 0.28796(5) 0.0195(2) Uani 1 1 d . . . H26A H -0.1752 0.5438 0.3241 0.029 Uiso 1 1 calc R . . H26B H -0.1131 0.5607 0.2638 0.029 Uiso 1 1 calc R . . H26C H -0.2935 0.5603 0.2689 0.029 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.01226(12) 0.02408(13) 0.01442(12) 0.00082(9) -0.00260(9) 0.00069(9) Cl2 0.01329(12) 0.03205(15) 0.01684(13) 0.00285(10) 0.00292(9) 0.00112(10) Cl3 0.02081(14) 0.03208(15) 0.01197(12) 0.00390(10) -0.00014(10) -0.00061(11) Cl4 0.01549(13) 0.02787(14) 0.01747(13) 0.00350(10) -0.00580(10) -0.00027(10) Cl5 0.01163(12) 0.02602(13) 0.01982(13) 0.00192(10) 0.00126(9) -0.00106(9) Cl6 0.01354(12) 0.02497(13) 0.01316(12) 0.00049(9) -0.00301(9) 0.00032(9) Cl7 0.01384(12) 0.02651(13) 0.01586(12) -0.00158(10) 0.00127(9) 0.00152(10) Cl8 0.02077(14) 0.03287(15) 0.01259(12) -0.00504(10) -0.00145(10) 0.00168(11) Cl9 0.01593(13) 0.02744(14) 0.01839(13) -0.00270(10) -0.00635(10) -0.00131(10) Cl10 0.01226(12) 0.02855(14) 0.02059(13) 0.00160(10) 0.00094(10) 0.00062(10) O1 0.0166(4) 0.0173(3) 0.0120(3) -0.0003(3) 0.0009(3) -0.0019(3) O2 0.0186(4) 0.0233(4) 0.0127(4) 0.0012(3) 0.0006(3) 0.0051(3) N1 0.0138(4) 0.0159(4) 0.0120(4) 0.0002(3) 0.0016(3) -0.0001(3) N2 0.0145(4) 0.0171(4) 0.0120(4) 0.0001(3) 0.0019(3) 0.0000(3) C1 0.0130(5) 0.0122(4) 0.0137(5) 0.0003(3) -0.0005(4) -0.0006(3) C2 0.0113(5) 0.0160(4) 0.0125(5) 0.0005(3) -0.0017(4) 0.0003(3) C3 0.0121(5) 0.0165(5) 0.0147(5) 0.0007(4) 0.0014(4) 0.0000(4) C4 0.0163(5) 0.0167(5) 0.0119(5) 0.0014(4) -0.0003(4) -0.0008(4) C5 0.0127(5) 0.0160(4) 0.0144(5) 0.0005(4) -0.0031(4) -0.0001(4) C6 0.0109(5) 0.0160(4) 0.0149(5) 0.0009(3) -0.0001(4) -0.0013(3) C7 0.0148(5) 0.0148(4) 0.0138(5) 0.0011(3) -0.0011(4) 0.0016(4) C8 0.0126(5) 0.0163(4) 0.0129(5) 0.0000(3) -0.0022(4) 0.0006(4) C9 0.0136(5) 0.0164(4) 0.0143(5) -0.0006(4) -0.0001(4) 0.0005(4) C10 0.0166(5) 0.0176(5) 0.0113(5) -0.0011(3) -0.0019(4) 0.0002(4) C11 0.0137(5) 0.0170(5) 0.0150(5) -0.0010(4) -0.0037(4) -0.0006(4) C12 0.0121(5) 0.0173(5) 0.0159(5) 0.0007(4) -0.0004(4) 0.0009(4) C13 0.0156(5) 0.0177(5) 0.0129(5) 0.0002(4) 0.0011(4) 0.0031(4) C14 0.0183(5) 0.0218(5) 0.0157(5) -0.0018(4) -0.0029(4) 0.0023(4) C15 0.0201(6) 0.0205(5) 0.0191(5) -0.0045(4) -0.0024(4) -0.0007(4) C16 0.0192(5) 0.0162(5) 0.0181(5) -0.0002(4) 0.0007(4) 0.0000(4) C17 0.0140(5) 0.0167(5) 0.0133(5) 0.0016(4) 0.0024(4) 0.0009(4) C18 0.0270(6) 0.0176(5) 0.0172(5) 0.0015(4) -0.0012(4) 0.0045(4) C19 0.0189(5) 0.0206(5) 0.0169(5) 0.0031(4) -0.0023(4) 0.0009(4) C20 0.0145(5) 0.0190(5) 0.0140(5) -0.0016(4) 0.0029(4) -0.0013(4) C21 0.0206(6) 0.0169(5) 0.0220(6) 0.0007(4) 0.0019(4) -0.0003(4) C22 0.0205(6) 0.0215(5) 0.0238(6) 0.0058(4) -0.0018(5) 0.0013(4) C23 0.0192(6) 0.0213(5) 0.0167(5) 0.0030(4) -0.0034(4) -0.0014(4) C24 0.0155(5) 0.0184(5) 0.0120(5) 0.0008(4) 0.0015(4) -0.0011(4) C25 0.0218(6) 0.0248(6) 0.0179(5) -0.0040(4) 0.0003(4) -0.0029(4) C26 0.0245(6) 0.0167(5) 0.0170(5) -0.0009(4) 0.0010(4) -0.0021(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C2 1.7343(11) . ? Cl2 C3 1.7201(12) . ? Cl3 C4 1.7228(12) . ? Cl4 C5 1.7246(11) . ? Cl5 C6 1.7206(12) . ? Cl6 C8 1.7274(11) . ? Cl7 C9 1.7175(12) . ? Cl8 C10 1.7214(12) . ? Cl9 C11 1.7221(11) . ? Cl10 C12 1.7176(12) . ? O1 C1 1.3030(13) . ? O1 H1 1.47(3) . ? O2 C7 1.3286(14) . ? O2 H2 0.86(3) . ? N1 C13 1.3480(14) . ? N1 C17 1.3542(14) . ? N1 H1 1.08(3) . ? N2 C24 1.3466(14) . ? N2 C20 1.3491(14) . ? C1 C2 1.4146(16) . ? C1 C6 1.4224(15) . ? C2 C3 1.3960(16) . ? C3 C4 1.3977(16) . ? C4 C5 1.3966(16) . ? C5 C6 1.3943(16) . ? C7 C8 1.4054(16) . ? C7 C12 1.4092(16) . ? C8 C9 1.3963(16) . ? C9 C10 1.3931(16) . ? C10 C11 1.3967(17) . ? C11 C12 1.3959(16) . ? C13 C14 1.3892(16) . ? C13 C18 1.4934(16) . ? C14 C15 1.3892(17) . ? C14 H14A 0.9500 . ? C15 C16 1.3863(17) . ? C15 H15A 0.9500 . ? C16 C17 1.3872(16) . ? C16 H16A 0.9500 . ? C17 C19 1.4969(16) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.3881(17) . ? C20 C25 1.5040(17) . ? C21 C22 1.3890(18) . ? C21 H21A 0.9500 . ? C22 C23 1.3867(17) . ? C22 H22A 0.9500 . ? C23 C24 1.3907(16) . ? C23 H23A 0.9500 . ? C24 C26 1.5012(16) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 118.1(11) . . ? C7 O2 H2 112(2) . . ? C13 N1 C17 122.80(10) . . ? C13 N1 H1 121.9(15) . . ? C17 N1 H1 115.1(15) . . ? C24 N2 C20 120.84(10) . . ? O1 C1 C2 123.08(10) . . ? O1 C1 C6 121.80(10) . . ? C2 C1 C6 115.11(10) . . ? C3 C2 C1 122.97(10) . . ? C3 C2 Cl1 119.88(9) . . ? C1 C2 Cl1 117.14(8) . . ? C2 C3 C4 120.05(10) . . ? C2 C3 Cl2 119.94(9) . . ? C4 C3 Cl2 120.01(9) . . ? C5 C4 C3 118.94(10) . . ? C5 C4 Cl3 120.79(9) . . ? C3 C4 Cl3 120.27(9) . . ? C6 C5 C4 120.49(10) . . ? C6 C5 Cl4 119.97(9) . . ? C4 C5 Cl4 119.54(9) . . ? C5 C6 C1 122.44(10) . . ? C5 C6 Cl5 120.45(9) . . ? C1 C6 Cl5 117.10(9) . . ? O2 C7 C8 123.58(10) . . ? O2 C7 C12 119.51(11) . . ? C8 C7 C12 116.89(10) . . ? C9 C8 C7 121.95(10) . . ? C9 C8 Cl6 119.87(9) . . ? C7 C8 Cl6 118.15(9) . . ? C10 C9 C8 119.96(11) . . ? C10 C9 Cl7 120.16(9) . . ? C8 C9 Cl7 119.87(9) . . ? C9 C10 C11 119.45(10) . . ? C9 C10 Cl8 119.93(9) . . ? C11 C10 Cl8 120.62(9) . . ? C12 C11 C10 120.14(10) . . ? C12 C11 Cl9 120.03(9) . . ? C10 C11 Cl9 119.84(9) . . ? C11 C12 C7 121.61(11) . . ? C11 C12 Cl10 120.50(9) . . ? C7 C12 Cl10 117.88(9) . . ? N1 C13 C14 119.26(10) . . ? N1 C13 C18 117.15(10) . . ? C14 C13 C18 123.58(10) . . ? C13 C14 C15 119.22(11) . . ? C13 C14 H14A 120.4 . . ? C15 C14 H14A 120.4 . . ? C16 C15 C14 120.18(11) . . ? C16 C15 H15A 119.9 . . ? C14 C15 H15A 119.9 . . ? C15 C16 C17 119.21(11) . . ? C15 C16 H16A 120.4 . . ? C17 C16 H16A 120.4 . . ? N1 C17 C16 119.29(10) . . ? N1 C17 C19 117.18(10) . . ? C16 C17 C19 123.53(10) . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N2 C20 C21 120.70(11) . . ? N2 C20 C25 117.13(10) . . ? C21 C20 C25 122.16(11) . . ? C20 C21 C22 119.06(11) . . ? C20 C21 H21A 120.5 . . ? C22 C21 H21A 120.5 . . ? C23 C22 C21 119.65(11) . . ? C23 C22 H22A 120.2 . . ? C21 C22 H22A 120.2 . . ? C22 C23 C24 119.02(11) . . ? C22 C23 H23A 120.5 . . ? C24 C23 H23A 120.5 . . ? N2 C24 C23 120.73(11) . . ? N2 C24 C26 117.05(10) . . ? C23 C24 C26 122.22(10) . . ? C20 C25 H25A 109.5 . . ? C20 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C20 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 1.08(3) 1.47(3) 2.5546(12) 179(3) . O2 H2 N2 0.86(3) 1.71(3) 2.5629(13) 175(3) . C26 H26B O1 0.98 2.47 3.3990(15) 157.4 . C18 H18B O2 0.98 2.50 3.3804(16) 148.6 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 33.73 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.559 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.076 # Attachment '6_24lpcp.cif' data_24lpcp _database_code_depnum_ccdc_archive 'CCDC 650956' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H10 Cl5 N O' _chemical_formula_weight 373.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.6844(16) _cell_length_b 13.449(3) _cell_length_c 12.804(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.622(4) _cell_angle_gamma 90.00 _cell_volume 1495.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7717 _cell_measurement_theta_min 2.79 _cell_measurement_theta_max 33.89 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.659 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.962 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22961 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0249 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 33.96 _reflns_number_total 6043 _reflns_number_gt 5008 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker AXS X8 Apex2' _computing_cell_refinement 'Bruker AXS SAINT V7.34A' _computing_data_reduction 'Bruker AXS SAINT V7.34A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker AXS XP' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+0.3000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6043 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0392 _refine_ls_R_factor_gt 0.0295 _refine_ls_wR_factor_ref 0.0799 _refine_ls_wR_factor_gt 0.0750 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.11118(3) 0.13595(2) 0.333063(19) 0.01907(6) Uani 1 1 d . . . Cl2 Cl 0.04804(3) 0.14334(3) 0.09214(2) 0.02803(8) Uani 1 1 d . . . Cl3 Cl -0.28972(3) 0.13235(2) 0.00385(2) 0.02119(6) Uani 1 1 d . . . Cl4 Cl -0.56355(3) 0.11005(2) 0.16033(2) 0.02076(6) Uani 1 1 d . . . Cl5 Cl -0.49679(3) 0.10157(3) 0.40236(2) 0.02638(7) Uani 1 1 d . . . O1 O -0.17175(9) 0.11211(6) 0.45881(6) 0.01869(15) Uani 1 1 d . . . N1 N 0.03139(11) 0.12101(6) 0.61070(7) 0.01501(16) Uani 1 1 d . . . H1 H -0.027(2) 0.1167(12) 0.5540(16) 0.044(5) Uiso 1 1 d . . . C1 C -0.19531(12) 0.11749(7) 0.35961(8) 0.01354(17) Uani 1 1 d . . . C2 C -0.07594(11) 0.12798(7) 0.28510(8) 0.01353(17) Uani 1 1 d . . . C3 C -0.10383(12) 0.13162(8) 0.17738(8) 0.01494(18) Uani 1 1 d . . . C4 C -0.25463(12) 0.12631(7) 0.13723(8) 0.01446(18) Uani 1 1 d . . . C5 C -0.37647(11) 0.11730(7) 0.20774(8) 0.01402(17) Uani 1 1 d . . . C6 C -0.34753(12) 0.11353(8) 0.31503(8) 0.01456(17) Uani 1 1 d . . . C7 C -0.03843(12) 0.12576(7) 0.70431(8) 0.01567(18) Uani 1 1 d . . . C8 C 0.05282(14) 0.13053(8) 0.79484(8) 0.0185(2) Uani 1 1 d . . . H8A H 0.0047 0.1340 0.8610 0.022 Uiso 1 1 calc R . . C9 C 0.21345(13) 0.13035(7) 0.78967(8) 0.01705(19) Uani 1 1 d . . . C10 C 0.27987(13) 0.12529(8) 0.69043(9) 0.01761(19) Uani 1 1 d . . . H10A H 0.3887 0.1255 0.6837 0.021 Uiso 1 1 calc R . . C11 C 0.18628(12) 0.12004(8) 0.60231(8) 0.01660(19) Uani 1 1 d . . . H11A H 0.2315 0.1157 0.5352 0.020 Uiso 1 1 calc R . . C12 C -0.21114(13) 0.12605(9) 0.70598(9) 0.0219(2) Uani 1 1 d . . . H12A H -0.2514 0.1206 0.6344 0.033 Uiso 1 1 calc R . . H12B H -0.2473 0.1882 0.7373 0.033 Uiso 1 1 calc R . . H12C H -0.2474 0.0696 0.7474 0.033 Uiso 1 1 calc R . . C13 C 0.31243(15) 0.13478(9) 0.88748(9) 0.0239(2) Uani 1 1 d . . . H13A H 0.4213 0.1364 0.8682 0.036 Uiso 1 1 calc R . . H13B H 0.2929 0.0760 0.9305 0.036 Uiso 1 1 calc R . . H13C H 0.2873 0.1948 0.9271 0.036 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.01175(11) 0.03147(14) 0.01395(11) 0.00116(9) -0.00252(8) -0.00258(9) Cl2 0.01557(12) 0.0557(2) 0.01283(11) 0.00205(11) 0.00152(9) -0.00419(12) Cl3 0.01980(12) 0.03246(14) 0.01122(10) 0.00160(9) -0.00403(9) -0.00167(10) Cl4 0.01240(11) 0.03168(14) 0.01810(12) 0.00121(9) -0.00463(8) -0.00101(9) Cl5 0.01314(11) 0.04960(19) 0.01644(12) 0.00340(11) 0.00202(9) -0.00092(11) O1 0.0155(3) 0.0295(4) 0.0111(3) 0.0009(3) -0.0019(3) -0.0009(3) N1 0.0157(4) 0.0178(4) 0.0116(3) 0.0000(3) -0.0015(3) 0.0002(3) C1 0.0132(4) 0.0157(4) 0.0117(4) 0.0001(3) -0.0016(3) -0.0002(3) C2 0.0109(4) 0.0177(4) 0.0119(4) -0.0001(3) -0.0023(3) -0.0009(3) C3 0.0126(4) 0.0200(5) 0.0122(4) 0.0007(3) 0.0001(3) -0.0012(3) C4 0.0153(4) 0.0176(4) 0.0104(4) 0.0003(3) -0.0032(3) -0.0003(3) C5 0.0118(4) 0.0168(4) 0.0134(4) 0.0007(3) -0.0029(3) -0.0004(3) C6 0.0115(4) 0.0192(4) 0.0129(4) 0.0010(3) 0.0002(3) 0.0003(3) C7 0.0160(4) 0.0176(4) 0.0133(4) -0.0003(3) -0.0008(3) 0.0006(3) C8 0.0217(5) 0.0217(5) 0.0122(4) -0.0011(3) -0.0017(4) 0.0003(4) C9 0.0204(5) 0.0155(4) 0.0152(4) -0.0003(3) -0.0046(4) -0.0006(4) C10 0.0159(4) 0.0190(5) 0.0178(4) 0.0012(4) -0.0041(4) -0.0002(4) C11 0.0152(4) 0.0210(5) 0.0136(4) 0.0010(3) -0.0012(3) 0.0008(4) C12 0.0165(5) 0.0298(6) 0.0195(5) -0.0012(4) 0.0016(4) 0.0009(4) C13 0.0266(6) 0.0273(6) 0.0174(5) -0.0011(4) -0.0099(4) -0.0008(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C2 1.7343(10) . ? Cl2 C3 1.7283(11) . ? Cl3 C4 1.7334(10) . ? Cl4 C5 1.7309(10) . ? Cl5 C6 1.7286(11) . ? O1 C1 1.2862(12) . ? N1 C11 1.3506(14) . ? N1 C7 1.3506(14) . ? N1 H1 0.89(2) . ? C1 C2 1.4235(15) . ? C1 C6 1.4353(14) . ? C2 C3 1.3985(14) . ? C3 C4 1.4035(14) . ? C4 C5 1.4036(15) . ? C5 C6 1.3947(14) . ? C7 C8 1.3985(15) . ? C7 C12 1.5002(16) . ? C8 C9 1.3973(16) . ? C8 H8A 0.9500 . ? C9 C10 1.4028(17) . ? C9 C13 1.5124(15) . ? C10 C11 1.3851(14) . ? C10 H10A 0.9500 . ? C11 H11A 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 N1 C7 121.88(9) . . ? C11 N1 H1 120.0(13) . . ? C7 N1 H1 118.1(13) . . ? O1 C1 C2 123.93(9) . . ? O1 C1 C6 121.78(10) . . ? C2 C1 C6 114.29(9) . . ? C3 C2 C1 123.01(9) . . ? C3 C2 Cl1 119.91(8) . . ? C1 C2 Cl1 117.08(7) . . ? C2 C3 C4 120.69(10) . . ? C2 C3 Cl2 120.05(8) . . ? C4 C3 Cl2 119.26(8) . . ? C3 C4 C5 118.41(9) . . ? C3 C4 Cl3 120.79(8) . . ? C5 C4 Cl3 120.80(7) . . ? C6 C5 C4 120.50(9) . . ? C6 C5 Cl4 120.12(8) . . ? C4 C5 Cl4 119.38(7) . . ? C5 C6 C1 123.08(10) . . ? C5 C6 Cl5 120.81(8) . . ? C1 C6 Cl5 116.11(8) . . ? N1 C7 C8 118.81(10) . . ? N1 C7 C12 118.12(9) . . ? C8 C7 C12 123.07(10) . . ? C9 C8 C7 121.18(10) . . ? C9 C8 H8A 119.4 . . ? C7 C8 H8A 119.4 . . ? C8 C9 C10 117.62(9) . . ? C8 C9 C13 121.30(11) . . ? C10 C9 C13 121.09(11) . . ? C11 C10 C9 119.79(10) . . ? C11 C10 H10A 120.1 . . ? C9 C10 H10A 120.1 . . ? N1 C11 C10 120.72(10) . . ? N1 C11 H11A 119.6 . . ? C10 C11 H11A 119.6 . . ? C7 C12 H12A 109.5 . . ? C7 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C7 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.89(2) 1.74(2) 2.6142(12) 169.1(19) . C12 H12A O1 0.98 2.36 3.1924(16) 142.0 . _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 33.96 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.563 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.066 # Attachment '7_35lpcp.cif' data_35lpcp _database_code_depnum_ccdc_archive 'CCDC 650957' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H13 Cl10 N O3' _chemical_formula_weight 657.80 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 7.0199(6) _cell_length_b 22.9038(18) _cell_length_c 15.2538(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2452.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6884 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 29.83 _exptl_crystal_description stick _exptl_crystal_colour colorless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.782 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 1.162 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16776 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0356 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 29.99 _reflns_number_total 6359 _reflns_number_gt 5576 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker AXS X8 Apex2' _computing_cell_refinement 'Bruker AXS SAINT V7.34A' _computing_data_reduction 'Bruker AXS SAINT V7.34A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker AXS XP' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.1200P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.22(4) _refine_ls_number_reflns 6359 _refine_ls_number_parameters 316 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0380 _refine_ls_R_factor_gt 0.0299 _refine_ls_wR_factor_ref 0.0658 _refine_ls_wR_factor_gt 0.0619 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.67225(8) 0.38409(2) 0.87648(4) 0.02109(12) Uani 1 1 d . . . Cl2 Cl 0.65512(9) 0.51035(2) 0.79741(4) 0.02487(13) Uani 1 1 d . . . Cl3 Cl 0.57199(9) 0.52802(2) 0.59762(4) 0.02677(13) Uani 1 1 d . . . Cl4 Cl 0.53768(9) 0.41799(3) 0.47564(4) 0.02540(13) Uani 1 1 d . . . Cl5 Cl 0.54569(9) 0.29344(2) 0.55669(4) 0.02315(12) Uani 1 1 d . . . Cl6 Cl 0.43864(9) 0.08862(2) 1.09501(4) 0.02432(13) Uani 1 1 d . . . Cl7 Cl 0.37722(9) 0.10200(3) 1.29759(4) 0.02704(13) Uani 1 1 d . . . Cl8 Cl 0.33921(9) 0.22625(3) 1.37949(4) 0.02852(14) Uani 1 1 d . . . Cl9 Cl 0.38911(8) 0.33681(2) 1.25942(4) 0.02638(13) Uani 1 1 d . . . Cl10 Cl 0.45525(8) 0.32077(2) 1.05736(4) 0.02200(12) Uani 1 1 d . . . N1 N 0.5967(3) 0.17652(9) 0.70073(13) 0.0195(4) Uani 1 1 d . . . H1 H 0.589(4) 0.2188(13) 0.705(2) 0.028(7) Uiso 1 1 d . . . O1 O 0.6193(2) 0.29090(6) 0.74635(10) 0.0183(3) Uani 1 1 d . . . O2 O 0.4723(2) 0.19495(7) 1.00210(11) 0.0217(4) Uani 1 1 d . . . H2 H 0.447(4) 0.2204(11) 0.979(2) 0.026(8) Uiso 1 1 d . . . C1 C 0.6094(3) 0.34350(9) 0.71381(14) 0.0152(4) Uani 1 1 d . . . C2 C 0.6317(3) 0.39426(9) 0.76569(15) 0.0161(4) Uani 1 1 d . . . C3 C 0.6213(3) 0.45024(9) 0.73027(15) 0.0162(4) Uani 1 1 d . . . C4 C 0.5887(3) 0.45852(10) 0.64066(16) 0.0178(5) Uani 1 1 d . . . C5 C 0.5687(3) 0.40943(9) 0.58739(15) 0.0168(4) Uani 1 1 d . . . C6 C 0.5770(3) 0.35371(9) 0.62329(15) 0.0159(4) Uani 1 1 d . . . C7 C 0.4430(3) 0.20526(9) 1.08680(15) 0.0154(4) Uani 1 1 d . . . C8 C 0.4266(3) 0.15676(9) 1.14291(16) 0.0174(5) Uani 1 1 d . . . C9 C 0.3967(3) 0.16331(10) 1.23208(15) 0.0172(4) Uani 1 1 d . . . C10 C 0.3837(3) 0.21858(10) 1.26905(15) 0.0185(4) Uani 1 1 d . . . C11 C 0.4018(3) 0.26776(10) 1.21513(15) 0.0169(4) Uani 1 1 d . . . C12 C 0.4314(3) 0.26099(9) 1.12509(15) 0.0163(4) Uani 1 1 d . . . C13 C 0.5749(3) 0.14862(10) 0.62382(16) 0.0204(5) Uani 1 1 d . . . H13A H 0.5571 0.1705 0.5715 0.024 Uiso 1 1 calc R . . C14 C 0.5783(3) 0.08812(9) 0.62030(16) 0.0186(5) Uani 1 1 d . . . C15 C 0.6060(3) 0.05803(10) 0.69863(16) 0.0189(5) Uani 1 1 d . . . H15A H 0.6101 0.0166 0.6977 0.023 Uiso 1 1 calc R . . C16 C 0.6279(3) 0.08700(9) 0.77809(15) 0.0191(5) Uani 1 1 d . . . C17 C 0.6215(3) 0.14753(10) 0.77679(16) 0.0188(5) Uani 1 1 d . . . H17A H 0.6346 0.1687 0.8300 0.023 Uiso 1 1 calc R . . C18 C 0.5529(4) 0.05721(10) 0.53391(16) 0.0229(5) Uani 1 1 d . . . H18A H 0.5487 0.0860 0.4864 0.034 Uiso 1 1 calc R . . H18B H 0.4335 0.0350 0.5348 0.034 Uiso 1 1 calc R . . H18C H 0.6599 0.0305 0.5243 0.034 Uiso 1 1 calc R . . C19 C 0.6564(4) 0.05557(10) 0.86355(16) 0.0254(5) Uani 1 1 d . . . H19A H 0.5536 0.0272 0.8719 0.038 Uiso 1 1 calc R . . H19B H 0.6551 0.0838 0.9118 0.038 Uiso 1 1 calc R . . H19C H 0.7792 0.0352 0.8627 0.038 Uiso 1 1 calc R . . O3 O 0.3620(3) 0.25662(7) 0.87082(11) 0.0205(3) Uani 1 1 d . . . H3 H 0.452(5) 0.2696(15) 0.838(2) 0.055(11) Uiso 1 1 d . . . H4 H 0.280(5) 0.2340(14) 0.839(2) 0.051(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0323(3) 0.0176(2) 0.0134(2) -0.0002(2) 0.0000(2) -0.0020(2) Cl2 0.0348(3) 0.0130(2) 0.0268(3) -0.0045(2) 0.0029(3) -0.0012(2) Cl3 0.0337(3) 0.0154(3) 0.0312(3) 0.0090(3) 0.0012(3) 0.0027(2) Cl4 0.0314(3) 0.0294(3) 0.0154(3) 0.0066(2) -0.0015(2) 0.0023(2) Cl5 0.0359(3) 0.0177(3) 0.0158(3) -0.0038(2) -0.0012(2) -0.0005(2) Cl6 0.0381(4) 0.0130(2) 0.0219(3) 0.0003(2) 0.0014(2) 0.0024(2) Cl7 0.0342(3) 0.0263(3) 0.0207(3) 0.0092(3) 0.0026(2) 0.0012(2) Cl8 0.0293(3) 0.0413(3) 0.0150(3) -0.0059(3) 0.0030(2) -0.0006(2) Cl9 0.0260(3) 0.0216(3) 0.0316(3) -0.0119(2) -0.0017(3) 0.0005(2) Cl10 0.0265(3) 0.0140(2) 0.0255(3) 0.0032(2) -0.0026(2) -0.0016(2) N1 0.0236(11) 0.0119(9) 0.0230(11) -0.0025(8) 0.0021(8) -0.0012(7) O1 0.0264(9) 0.0128(7) 0.0156(8) 0.0017(6) -0.0002(6) -0.0013(6) O2 0.0330(10) 0.0162(8) 0.0158(8) 0.0030(7) -0.0009(7) 0.0045(7) C1 0.0169(11) 0.0134(10) 0.0153(11) 0.0003(8) 0.0009(9) -0.0007(8) C2 0.0191(11) 0.0159(10) 0.0133(10) -0.0001(9) 0.0030(8) -0.0018(8) C3 0.0175(12) 0.0124(10) 0.0186(11) -0.0020(9) 0.0027(8) -0.0003(8) C4 0.0169(12) 0.0154(10) 0.0210(12) 0.0044(9) 0.0027(9) 0.0009(8) C5 0.0173(11) 0.0201(11) 0.0129(10) 0.0045(9) 0.0013(8) 0.0018(8) C6 0.0169(11) 0.0153(11) 0.0157(11) 0.0005(9) 0.0029(8) -0.0003(8) C7 0.0152(11) 0.0157(10) 0.0152(10) 0.0007(9) -0.0006(8) 0.0003(8) C8 0.0173(12) 0.0141(10) 0.0206(12) 0.0006(9) -0.0018(8) 0.0010(8) C9 0.0171(12) 0.0193(11) 0.0152(11) 0.0057(9) -0.0012(8) 0.0006(9) C10 0.0143(11) 0.0264(11) 0.0149(11) -0.0029(9) 0.0011(8) -0.0002(8) C11 0.0141(11) 0.0179(11) 0.0187(12) -0.0033(9) -0.0039(8) 0.0013(8) C12 0.0154(12) 0.0150(11) 0.0184(11) 0.0024(9) -0.0021(8) -0.0014(8) C13 0.0203(12) 0.0174(11) 0.0234(13) 0.0012(10) 0.0029(9) -0.0004(9) C14 0.0165(12) 0.0166(11) 0.0228(12) -0.0013(9) 0.0018(8) 0.0004(8) C15 0.0182(12) 0.0130(11) 0.0253(12) -0.0018(9) 0.0025(9) 0.0004(8) C16 0.0185(12) 0.0159(10) 0.0230(12) -0.0038(9) 0.0005(9) -0.0013(8) C17 0.0174(11) 0.0170(10) 0.0221(12) -0.0059(9) 0.0015(9) -0.0014(8) C18 0.0301(14) 0.0197(12) 0.0189(12) -0.0024(10) 0.0012(9) -0.0007(9) C19 0.0331(14) 0.0189(11) 0.0244(13) -0.0001(10) -0.0007(10) 0.0021(9) O3 0.0270(10) 0.0166(8) 0.0181(8) 0.0038(7) -0.0016(7) -0.0018(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C2 1.729(2) . ? Cl2 C3 1.732(2) . ? Cl3 C4 1.726(2) . ? Cl4 C5 1.730(2) . ? Cl5 C6 1.728(2) . ? Cl6 C8 1.725(2) . ? Cl7 C9 1.729(2) . ? Cl8 C10 1.722(2) . ? Cl9 C11 1.722(2) . ? Cl10 C12 1.723(2) . ? N1 C13 1.345(3) . ? N1 C17 1.348(3) . ? N1 H1 0.97(3) . ? O1 C1 1.305(3) . ? O2 C7 1.330(3) . ? O2 H2 0.70(3) . ? C1 C2 1.415(3) . ? C1 C6 1.419(3) . ? C2 C3 1.393(3) . ? C3 C4 1.399(3) . ? C4 C5 1.394(3) . ? C5 C6 1.390(3) . ? C7 C12 1.406(3) . ? C7 C8 1.407(3) . ? C8 C9 1.384(3) . ? C9 C10 1.389(3) . ? C10 C11 1.400(3) . ? C11 C12 1.398(3) . ? C13 C14 1.387(3) . ? C13 H13A 0.9500 . ? C14 C15 1.393(3) . ? C14 C18 1.507(3) . ? C15 C16 1.390(3) . ? C15 H15A 0.9500 . ? C16 C17 1.387(3) . ? C16 C19 1.502(3) . ? C17 H17A 0.9500 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? O3 H3 0.86(4) . ? O3 H4 0.91(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 N1 C17 122.1(2) . . ? C13 N1 H1 121.3(18) . . ? C17 N1 H1 116.5(18) . . ? C7 O2 H2 107(3) . . ? O1 C1 C2 122.7(2) . . ? O1 C1 C6 122.1(2) . . ? C2 C1 C6 115.24(19) . . ? C3 C2 C1 122.2(2) . . ? C3 C2 Cl1 120.76(17) . . ? C1 C2 Cl1 117.01(16) . . ? C2 C3 C4 120.8(2) . . ? C2 C3 Cl2 119.66(18) . . ? C4 C3 Cl2 119.50(17) . . ? C5 C4 C3 118.5(2) . . ? C5 C4 Cl3 121.01(18) . . ? C3 C4 Cl3 120.52(18) . . ? C6 C5 C4 120.4(2) . . ? C6 C5 Cl4 119.85(17) . . ? C4 C5 Cl4 119.71(17) . . ? C5 C6 C1 122.8(2) . . ? C5 C6 Cl5 119.76(17) . . ? C1 C6 Cl5 117.44(16) . . ? O2 C7 C12 125.0(2) . . ? O2 C7 C8 117.61(19) . . ? C12 C7 C8 117.3(2) . . ? C9 C8 C7 121.6(2) . . ? C9 C8 Cl6 121.44(17) . . ? C7 C8 Cl6 116.91(18) . . ? C8 C9 C10 120.5(2) . . ? C8 C9 Cl7 119.46(17) . . ? C10 C9 Cl7 120.03(18) . . ? C9 C10 C11 119.2(2) . . ? C9 C10 Cl8 120.13(18) . . ? C11 C10 Cl8 120.60(17) . . ? C12 C11 C10 120.1(2) . . ? C12 C11 Cl9 119.67(17) . . ? C10 C11 Cl9 120.23(17) . . ? C11 C12 C7 121.2(2) . . ? C11 C12 Cl10 121.02(17) . . ? C7 C12 Cl10 117.82(17) . . ? N1 C13 C14 120.4(2) . . ? N1 C13 H13A 119.8 . . ? C14 C13 H13A 119.8 . . ? C13 C14 C15 117.6(2) . . ? C13 C14 C18 120.1(2) . . ? C15 C14 C18 122.30(19) . . ? C16 C15 C14 121.8(2) . . ? C16 C15 H15A 119.1 . . ? C14 C15 H15A 119.1 . . ? C17 C16 C15 117.4(2) . . ? C17 C16 C19 119.7(2) . . ? C15 C16 C19 122.85(19) . . ? N1 C17 C16 120.6(2) . . ? N1 C17 H17A 119.7 . . ? C16 C17 H17A 119.7 . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? H3 O3 H4 110(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.97(3) 1.78(3) 2.715(2) 160(3) . O2 H2 O3 0.70(3) 1.94(3) 2.570(2) 149(3) . O3 H3 O1 0.86(4) 1.89(4) 2.736(2) 168(3) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.375 _refine_diff_density_min -0.355 _refine_diff_density_rms 0.074 # Attachment '8_25lpcp.cif' data_25lpcp _database_code_depnum_ccdc_archive 'CCDC 650958' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H11 Cl10 N O2' _chemical_formula_weight 639.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3420(5) _cell_length_b 11.5145(7) _cell_length_c 12.2668(8) _cell_angle_alpha 94.367(4) _cell_angle_beta 104.227(3) _cell_angle_gamma 107.084(3) _cell_volume 1206.84(13) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6789 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 29.99 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.761 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 636 _exptl_absorpt_coefficient_mu 1.175 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20424 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 30.00 _reflns_number_total 7029 _reflns_number_gt 5609 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker AXS X8 Apex2' _computing_cell_refinement 'Bruker AXS SAINT V7.34A' _computing_data_reduction 'Bruker AXS SAINT V7.34A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker AXS XP' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.4000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7029 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0429 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_ref 0.0747 _refine_ls_wR_factor_gt 0.0686 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.52636(5) 0.82464(4) 0.04531(4) 0.03155(11) Uani 1 1 d . . . Cl2 Cl 0.39581(6) 0.58411(5) -0.13613(4) 0.03589(12) Uani 1 1 d . . . Cl3 Cl 0.15339(5) 0.35042(4) -0.09800(4) 0.02804(10) Uani 1 1 d . . . Cl4 Cl 0.03359(5) 0.36227(4) 0.11907(4) 0.02240(9) Uani 1 1 d . . . Cl5 Cl 0.17436(6) 0.59781(4) 0.30179(4) 0.02884(10) Uani 1 1 d . . . Cl6 Cl 0.81450(5) 1.11198(3) 0.59906(3) 0.02063(9) Uani 1 1 d . . . Cl7 Cl 1.10025(5) 1.06587(4) 0.76302(4) 0.02716(10) Uani 1 1 d . . . Cl8 Cl 1.16661(5) 0.81797(5) 0.72037(4) 0.03165(11) Uani 1 1 d . . . Cl9 Cl 0.94982(6) 0.62042(4) 0.50857(4) 0.03269(11) Uani 1 1 d . . . Cl10 Cl 0.66481(5) 0.66813(4) 0.34716(4) 0.02784(10) Uani 1 1 d . . . N1 N 0.38113(16) 1.01898(13) 0.22985(11) 0.0185(3) Uani 1 1 d . . . H1 H 0.391(2) 0.941(2) 0.2301(17) 0.033(6) Uiso 1 1 d . . . O1 O 0.40459(14) 0.80056(11) 0.24450(10) 0.0240(3) Uani 1 1 d . . . O2 O 0.63098(15) 0.91169(11) 0.41818(11) 0.0243(3) Uani 1 1 d . . . H2 H 0.575(3) 0.860(2) 0.367(2) 0.050(8) Uiso 1 1 d . . . C1 C 0.34843(18) 0.70149(15) 0.16799(14) 0.0192(3) Uani 1 1 d . . . C2 C 0.39369(18) 0.69378(15) 0.06628(14) 0.0210(3) Uani 1 1 d . . . C3 C 0.33501(19) 0.58726(16) -0.01414(14) 0.0211(3) Uani 1 1 d . . . C4 C 0.22631(18) 0.48289(14) 0.00188(13) 0.0190(3) Uani 1 1 d . . . C5 C 0.17515(18) 0.48779(14) 0.09928(13) 0.0179(3) Uani 1 1 d . . . C6 C 0.23639(19) 0.59404(15) 0.18064(13) 0.0193(3) Uani 1 1 d . . . C7 C 0.75202(18) 0.88634(14) 0.48339(13) 0.0181(3) Uani 1 1 d . . . C8 C 0.85239(18) 0.97525(14) 0.57636(13) 0.0170(3) Uani 1 1 d . . . C9 C 0.97876(18) 0.95439(15) 0.64977(13) 0.0189(3) Uani 1 1 d . . . C10 C 1.00854(19) 0.84331(16) 0.63044(14) 0.0210(3) Uani 1 1 d . . . C11 C 0.91156(19) 0.75523(15) 0.53723(14) 0.0207(3) Uani 1 1 d . . . C12 C 0.78437(19) 0.77599(14) 0.46416(14) 0.0190(3) Uani 1 1 d . . . C13 C 0.27220(18) 1.03719(15) 0.14449(14) 0.0198(3) Uani 1 1 d . . . C14 C 0.25006(19) 1.15105(16) 0.15059(15) 0.0228(3) Uani 1 1 d . . . H14A H 0.1737 1.1664 0.0917 0.027 Uiso 1 1 calc R . . C15 C 0.33924(19) 1.24249(15) 0.24250(15) 0.0227(3) Uani 1 1 d . . . H15A H 0.3223 1.3199 0.2466 0.027 Uiso 1 1 calc R . . C16 C 0.45382(19) 1.22276(15) 0.32941(14) 0.0201(3) Uani 1 1 d . . . C17 C 0.46967(19) 1.10678(15) 0.31976(14) 0.0199(3) Uani 1 1 d . . . H17A H 0.5446 1.0888 0.3778 0.024 Uiso 1 1 calc R . . C18 C 0.1823(2) 0.93168(17) 0.04933(15) 0.0267(4) Uani 1 1 d . . . H18A H 0.2552 0.9031 0.0180 0.040 Uiso 1 1 calc R . . H18B H 0.1146 0.9587 -0.0107 0.040 Uiso 1 1 calc R . . H18C H 0.1184 0.8643 0.0784 0.040 Uiso 1 1 calc R . . C19 C 0.5577(2) 1.32113(17) 0.42792(16) 0.0291(4) Uani 1 1 d . . . H19A H 0.5820 1.2835 0.4962 0.044 Uiso 1 1 calc R . . H19B H 0.5042 1.3800 0.4415 0.044 Uiso 1 1 calc R . . H19C H 0.6546 1.3640 0.4103 0.044 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0256(2) 0.0220(2) 0.0438(3) 0.00183(19) 0.01443(19) -0.00002(17) Cl2 0.0439(3) 0.0327(3) 0.0335(3) -0.0008(2) 0.0242(2) 0.0065(2) Cl3 0.0339(2) 0.0199(2) 0.0253(2) -0.00733(16) 0.00721(17) 0.00482(17) Cl4 0.0229(2) 0.01561(18) 0.0273(2) 0.00382(15) 0.00636(16) 0.00471(15) Cl5 0.0424(3) 0.0258(2) 0.0177(2) 0.00111(16) 0.01066(18) 0.00895(19) Cl6 0.0263(2) 0.01382(18) 0.0225(2) -0.00063(14) 0.00917(15) 0.00645(15) Cl7 0.0249(2) 0.0279(2) 0.0213(2) 0.00083(17) 0.00214(16) 0.00197(17) Cl8 0.0233(2) 0.0392(3) 0.0381(3) 0.0185(2) 0.00925(18) 0.01490(19) Cl9 0.0392(3) 0.0205(2) 0.0497(3) 0.0102(2) 0.0203(2) 0.01873(19) Cl10 0.0384(2) 0.01619(19) 0.0262(2) -0.00444(16) 0.00654(18) 0.00889(17) N1 0.0204(7) 0.0163(7) 0.0193(7) 0.0028(5) 0.0061(5) 0.0062(5) O1 0.0261(6) 0.0168(6) 0.0224(6) -0.0044(5) -0.0022(5) 0.0066(5) O2 0.0280(7) 0.0184(6) 0.0219(6) -0.0033(5) -0.0033(5) 0.0107(5) C1 0.0195(8) 0.0155(7) 0.0194(8) -0.0008(6) -0.0004(6) 0.0065(6) C2 0.0176(8) 0.0175(8) 0.0258(9) 0.0017(7) 0.0047(6) 0.0044(6) C3 0.0226(8) 0.0212(8) 0.0208(8) 0.0009(6) 0.0086(6) 0.0076(7) C4 0.0204(8) 0.0152(7) 0.0191(8) -0.0024(6) 0.0024(6) 0.0061(6) C5 0.0187(7) 0.0137(7) 0.0198(8) 0.0020(6) 0.0022(6) 0.0058(6) C6 0.0226(8) 0.0188(8) 0.0168(8) 0.0020(6) 0.0039(6) 0.0087(6) C7 0.0217(8) 0.0150(7) 0.0196(8) 0.0039(6) 0.0083(6) 0.0067(6) C8 0.0218(8) 0.0127(7) 0.0187(8) 0.0022(6) 0.0101(6) 0.0049(6) C9 0.0194(8) 0.0188(8) 0.0179(8) 0.0031(6) 0.0076(6) 0.0035(6) C10 0.0185(8) 0.0248(9) 0.0248(9) 0.0111(7) 0.0108(6) 0.0085(7) C11 0.0260(8) 0.0161(8) 0.0278(9) 0.0082(6) 0.0156(7) 0.0107(7) C12 0.0250(8) 0.0138(7) 0.0197(8) 0.0013(6) 0.0089(6) 0.0068(6) C13 0.0163(7) 0.0210(8) 0.0205(8) 0.0037(6) 0.0054(6) 0.0035(6) C14 0.0198(8) 0.0228(8) 0.0242(9) 0.0043(7) 0.0027(6) 0.0071(7) C15 0.0223(8) 0.0165(8) 0.0292(9) 0.0042(7) 0.0077(7) 0.0057(6) C16 0.0194(8) 0.0170(8) 0.0219(8) 0.0020(6) 0.0068(6) 0.0022(6) C17 0.0184(8) 0.0205(8) 0.0194(8) 0.0038(6) 0.0047(6) 0.0046(6) C18 0.0247(9) 0.0267(9) 0.0240(9) -0.0019(7) 0.0017(7) 0.0069(7) C19 0.0301(10) 0.0214(9) 0.0284(10) -0.0028(7) 0.0012(7) 0.0047(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C2 1.7295(17) . ? Cl2 C3 1.7276(16) . ? Cl3 C4 1.7282(16) . ? Cl4 C5 1.7277(17) . ? Cl5 C6 1.7246(16) . ? Cl6 C8 1.7293(15) . ? Cl7 C9 1.7214(17) . ? Cl8 C10 1.7274(17) . ? Cl9 C11 1.7220(16) . ? Cl10 C12 1.7249(17) . ? N1 C13 1.346(2) . ? N1 C17 1.347(2) . ? N1 H1 0.93(2) . ? O1 C1 1.3041(18) . ? O2 C7 1.3375(19) . ? O2 H2 0.79(3) . ? C1 C6 1.414(2) . ? C1 C2 1.417(2) . ? C2 C3 1.390(2) . ? C3 C4 1.390(2) . ? C4 C5 1.395(2) . ? C5 C6 1.394(2) . ? C7 C8 1.400(2) . ? C7 C12 1.406(2) . ? C8 C9 1.393(2) . ? C9 C10 1.402(2) . ? C10 C11 1.390(2) . ? C11 C12 1.396(2) . ? C13 C14 1.385(2) . ? C13 C18 1.499(2) . ? C14 C15 1.384(2) . ? C14 H14A 0.9500 . ? C15 C16 1.398(2) . ? C15 H15A 0.9500 . ? C16 C17 1.386(2) . ? C16 C19 1.501(2) . ? C17 H17A 0.9500 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 N1 C17 122.79(14) . . ? C13 N1 H1 119.0(13) . . ? C17 N1 H1 118.1(13) . . ? C7 O2 H2 116.3(18) . . ? O1 C1 C6 122.00(15) . . ? O1 C1 C2 122.78(15) . . ? C6 C1 C2 115.22(14) . . ? C3 C2 C1 122.46(15) . . ? C3 C2 Cl1 120.75(13) . . ? C1 C2 Cl1 116.79(12) . . ? C4 C3 C2 120.67(15) . . ? C4 C3 Cl2 119.30(12) . . ? C2 C3 Cl2 120.02(13) . . ? C3 C4 C5 118.68(14) . . ? C3 C4 Cl3 120.71(12) . . ? C5 C4 Cl3 120.60(13) . . ? C6 C5 C4 120.41(15) . . ? C6 C5 Cl4 119.53(12) . . ? C4 C5 Cl4 120.06(12) . . ? C5 C6 C1 122.52(15) . . ? C5 C6 Cl5 119.87(13) . . ? C1 C6 Cl5 117.61(12) . . ? O2 C7 C8 117.88(13) . . ? O2 C7 C12 123.95(15) . . ? C8 C7 C12 118.16(14) . . ? C9 C8 C7 121.25(14) . . ? C9 C8 Cl6 120.48(12) . . ? C7 C8 Cl6 118.27(12) . . ? C8 C9 C10 119.99(15) . . ? C8 C9 Cl7 120.06(12) . . ? C10 C9 Cl7 119.94(13) . . ? C11 C10 C9 119.34(15) . . ? C11 C10 Cl8 120.57(12) . . ? C9 C10 Cl8 120.08(13) . . ? C10 C11 C12 120.57(14) . . ? C10 C11 Cl9 120.25(13) . . ? C12 C11 Cl9 119.16(13) . . ? C11 C12 C7 120.66(15) . . ? C11 C12 Cl10 120.93(12) . . ? C7 C12 Cl10 118.40(13) . . ? N1 C13 C14 118.19(15) . . ? N1 C13 C18 117.27(15) . . ? C14 C13 C18 124.55(15) . . ? C15 C14 C13 120.01(15) . . ? C15 C14 H14A 120.0 . . ? C13 C14 H14A 120.0 . . ? C14 C15 C16 121.06(15) . . ? C14 C15 H15A 119.5 . . ? C16 C15 H15A 119.5 . . ? C17 C16 C15 116.51(15) . . ? C17 C16 C19 120.74(15) . . ? C15 C16 C19 122.74(15) . . ? N1 C17 C16 121.42(15) . . ? N1 C17 H17A 119.3 . . ? C16 C17 H17A 119.3 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.93(2) 1.68(2) 2.6036(18) 173.8(19) . O2 H2 O1 0.79(3) 1.81(2) 2.5356(17) 152(2) . C17 H17A O2 0.95 2.45 3.207(2) 137.0 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.439 _refine_diff_density_min -0.372 _refine_diff_density_rms 0.073 # Attachment '9_34lpcp.cif' data_34lpcp _database_code_depnum_ccdc_archive 'CCDC 650959' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H11 Cl10 N O2' _chemical_formula_weight 639.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.7771(5) _cell_length_b 12.4154(5) _cell_length_c 16.9000(7) _cell_angle_alpha 76.399(2) _cell_angle_beta 86.657(2) _cell_angle_gamma 85.458(2) _cell_volume 2392.23(17) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9908 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 30.09 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.776 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1272 _exptl_absorpt_coefficient_mu 1.186 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 38411 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0395 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.24 _diffrn_reflns_theta_max 30.00 _reflns_number_total 13942 _reflns_number_gt 11189 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker AXS X8 Apex2' _computing_cell_refinement 'Bruker AXS SAINT V7.34A' _computing_data_reduction 'Bruker AXS SAINT V7.34A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker AXS XP' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.4000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 13942 _refine_ls_number_parameters 597 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0435 _refine_ls_R_factor_gt 0.0309 _refine_ls_wR_factor_ref 0.0722 _refine_ls_wR_factor_gt 0.0666 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl -0.33267(4) -0.39147(4) 0.69191(3) 0.02182(9) Uani 1 1 d . . . Cl2 Cl -0.26679(4) -0.48320(3) 0.53571(3) 0.02100(9) Uani 1 1 d . . . Cl3 Cl -0.05910(4) -0.39321(4) 0.42223(3) 0.02374(9) Uani 1 1 d . . . Cl4 Cl 0.08806(4) -0.22225(4) 0.47000(3) 0.02668(10) Uani 1 1 d . . . Cl5 Cl 0.01703(4) -0.12601(4) 0.62080(3) 0.02100(9) Uani 1 1 d . . . Cl6 Cl 0.08535(4) -0.16086(3) 0.93867(3) 0.02184(9) Uani 1 1 d . . . Cl7 Cl 0.24765(4) -0.33997(4) 1.04656(3) 0.02382(9) Uani 1 1 d . . . Cl8 Cl 0.25362(4) -0.58748(4) 1.03404(3) 0.02563(10) Uani 1 1 d . . . Cl9 Cl 0.11245(4) -0.65019(3) 0.90318(3) 0.02287(9) Uani 1 1 d . . . Cl10 Cl -0.05076(4) -0.46889(4) 0.79569(3) 0.02426(9) Uani 1 1 d . . . Cl11 Cl 0.16300(4) 0.08972(4) 0.66129(2) 0.02165(9) Uani 1 1 d . . . Cl12 Cl 0.24989(4) 0.00646(4) 0.50712(2) 0.02111(9) Uani 1 1 d . . . Cl13 Cl 0.46022(4) 0.11011(4) 0.40207(2) 0.02158(9) Uani 1 1 d . . . Cl14 Cl 0.58255(4) 0.29411(4) 0.45596(3) 0.02523(10) Uani 1 1 d . . . Cl15 Cl 0.49246(4) 0.37724(3) 0.60975(3) 0.02026(9) Uani 1 1 d . . . Cl16 Cl 0.19335(4) 0.06768(4) 1.01032(2) 0.02088(9) Uani 1 1 d . . . Cl17 Cl 0.34281(4) -0.12740(3) 1.11599(2) 0.01911(8) Uani 1 1 d . . . Cl18 Cl 0.54606(4) -0.24457(4) 1.03443(3) 0.02165(9) Uani 1 1 d . . . Cl19 Cl 0.60393(3) -0.16030(3) 0.84795(2) 0.01901(8) Uani 1 1 d . . . Cl20 Cl 0.45773(4) 0.03846(4) 0.74590(2) 0.01924(8) Uani 1 1 d . . . O1 O -0.18237(10) -0.22616(10) 0.71672(7) 0.0176(2) Uani 1 1 d . . . O2 O -0.04417(12) -0.24304(11) 0.83078(8) 0.0236(3) Uani 1 1 d . . . H2 H -0.081(2) -0.258(2) 0.7985(15) 0.056(8) Uiso 1 1 d . . . O3 O 0.29480(10) 0.26007(10) 0.69676(7) 0.0176(2) Uani 1 1 d . . . O4 O 0.26909(10) 0.13165(10) 0.84330(7) 0.0188(3) Uani 1 1 d . . . H4 H 0.286(2) 0.157(2) 0.7943(17) 0.068(9) Uiso 1 1 d . . . N1 N -0.18430(12) -0.01551(13) 0.72144(9) 0.0192(3) Uani 1 1 d . . . H1 H -0.1826(19) -0.087(2) 0.7178(13) 0.043(7) Uiso 1 1 d . . . N2 N 0.29276(13) 0.45318(13) 0.72588(9) 0.0213(3) Uani 1 1 d . . . H3 H 0.292(2) 0.381(2) 0.7094(16) 0.067(9) Uiso 1 1 d . . . C1 C -0.15529(14) -0.26321(13) 0.65119(10) 0.0150(3) Uani 1 1 d . . . C2 C -0.21746(14) -0.34396(14) 0.62925(10) 0.0157(3) Uani 1 1 d . . . C3 C -0.18792(14) -0.38486(13) 0.55988(10) 0.0161(3) Uani 1 1 d . . . C4 C -0.09445(14) -0.34621(14) 0.50965(10) 0.0176(3) Uani 1 1 d . . . C5 C -0.03052(14) -0.26776(14) 0.52977(10) 0.0177(3) Uani 1 1 d . . . C6 C -0.06115(14) -0.22677(14) 0.59867(10) 0.0165(3) Uani 1 1 d . . . C7 C 0.02258(14) -0.32449(14) 0.87412(10) 0.0167(3) Uani 1 1 d . . . C8 C 0.09119(14) -0.29728(14) 0.93083(10) 0.0168(3) Uani 1 1 d . . . C9 C 0.16283(14) -0.37745(14) 0.97905(10) 0.0169(3) Uani 1 1 d . . . C10 C 0.16796(14) -0.48745(14) 0.97244(10) 0.0172(3) Uani 1 1 d . . . C11 C 0.10196(14) -0.51569(14) 0.91518(10) 0.0164(3) Uani 1 1 d . . . C12 C 0.03044(14) -0.43510(14) 0.86704(10) 0.0165(3) Uani 1 1 d . . . C13 C 0.33031(14) 0.23044(13) 0.62926(9) 0.0149(3) Uani 1 1 d . . . C14 C 0.27762(14) 0.14759(14) 0.60279(9) 0.0149(3) Uani 1 1 d . . . C15 C 0.31716(14) 0.11021(14) 0.53410(10) 0.0158(3) Uani 1 1 d . . . C16 C 0.41085(14) 0.15580(14) 0.48766(9) 0.0161(3) Uani 1 1 d . . . C17 C 0.46494(14) 0.23791(14) 0.51171(10) 0.0160(3) Uani 1 1 d . . . C18 C 0.42498(14) 0.27404(13) 0.58093(10) 0.0154(3) Uani 1 1 d . . . C19 C 0.33416(13) 0.04527(13) 0.88335(9) 0.0143(3) Uani 1 1 d . . . C20 C 0.30836(14) 0.00493(14) 0.96683(9) 0.0150(3) Uani 1 1 d . . . C21 C 0.37377(14) -0.08305(14) 1.01307(9) 0.0149(3) Uani 1 1 d . . . C22 C 0.46532(14) -0.13554(13) 0.97728(9) 0.0150(3) Uani 1 1 d . . . C23 C 0.49113(13) -0.09774(14) 0.89404(10) 0.0147(3) Uani 1 1 d . . . C24 C 0.42599(14) -0.00869(14) 0.84838(9) 0.0147(3) Uani 1 1 d . . . C25 C -0.10623(15) 0.01651(15) 0.76457(10) 0.0202(4) Uani 1 1 d . . . H25A H -0.0516 -0.0372 0.7926 0.024 Uiso 1 1 calc R . . C26 C -0.10391(14) 0.12615(15) 0.76886(10) 0.0183(3) Uani 1 1 d . . . C27 C -0.18565(15) 0.20361(14) 0.72707(10) 0.0184(3) Uani 1 1 d . . . C28 C -0.26581(15) 0.16658(15) 0.68336(10) 0.0215(4) Uani 1 1 d . . . H28A H -0.3221 0.2178 0.6549 0.026 Uiso 1 1 calc R . . C29 C -0.26345(15) 0.05661(16) 0.68142(10) 0.0206(4) Uani 1 1 d . . . H29A H -0.3180 0.0318 0.6517 0.025 Uiso 1 1 calc R . . C30 C -0.01740(16) 0.15898(18) 0.81878(12) 0.0293(4) Uani 1 1 d . . . H30A H 0.0336 0.0941 0.8413 0.044 Uiso 1 1 calc R . . H30B H -0.0563 0.1873 0.8634 0.044 Uiso 1 1 calc R . . H30C H 0.0271 0.2170 0.7843 0.044 Uiso 1 1 calc R . . C31 C -0.18930(18) 0.32363(15) 0.72928(11) 0.0276(4) Uani 1 1 d . . . H31A H -0.1885 0.3300 0.7859 0.041 Uiso 1 1 calc R . . H31B H -0.2591 0.3620 0.7046 0.041 Uiso 1 1 calc R . . H31C H -0.1227 0.3574 0.6987 0.041 Uiso 1 1 calc R . . C32 C 0.36430(16) 0.46216(15) 0.78261(11) 0.0232(4) Uani 1 1 d . . . H32A H 0.4088 0.3980 0.8091 0.028 Uiso 1 1 calc R . . C33 C 0.37551(15) 0.56192(15) 0.80384(10) 0.0212(4) Uani 1 1 d . . . C34 C 0.30872(15) 0.65523(15) 0.76384(11) 0.0213(4) Uani 1 1 d . . . C35 C 0.23411(15) 0.64303(15) 0.70587(11) 0.0239(4) Uani 1 1 d . . . H35A H 0.1875 0.7052 0.6788 0.029 Uiso 1 1 calc R . . C36 C 0.22776(15) 0.54097(16) 0.68777(11) 0.0234(4) Uani 1 1 d . . . H36A H 0.1770 0.5331 0.6481 0.028 Uiso 1 1 calc R . . C37 C 0.45864(18) 0.56784(17) 0.86684(12) 0.0302(4) Uani 1 1 d . . . H37A H 0.4961 0.4940 0.8875 0.045 Uiso 1 1 calc R . . H37B H 0.4178 0.5934 0.9119 0.045 Uiso 1 1 calc R . . H37C H 0.5161 0.6199 0.8421 0.045 Uiso 1 1 calc R . . C38 C 0.31946(18) 0.76787(16) 0.78050(13) 0.0313(4) Uani 1 1 d . . . H38A H 0.2590 0.8200 0.7535 0.047 Uiso 1 1 calc R . . H38B H 0.3940 0.7946 0.7595 0.047 Uiso 1 1 calc R . . H38C H 0.3124 0.7623 0.8394 0.047 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0197(2) 0.0185(2) 0.0272(2) -0.00476(17) 0.00384(16) -0.00617(16) Cl2 0.0244(2) 0.0158(2) 0.0246(2) -0.00544(16) -0.00664(16) -0.00544(16) Cl3 0.0285(2) 0.0259(2) 0.01954(19) -0.01037(17) -0.00087(17) -0.00280(18) Cl4 0.0228(2) 0.0330(3) 0.0269(2) -0.01151(19) 0.00813(18) -0.01063(19) Cl5 0.01849(19) 0.0199(2) 0.0277(2) -0.01030(17) 0.00088(16) -0.00699(16) Cl6 0.0266(2) 0.0143(2) 0.0273(2) -0.00945(16) -0.00419(17) -0.00113(16) Cl7 0.0248(2) 0.0245(2) 0.0251(2) -0.01002(17) -0.00756(17) -0.00165(17) Cl8 0.0251(2) 0.0210(2) 0.0299(2) -0.00530(18) -0.00691(18) 0.00616(17) Cl9 0.0288(2) 0.0130(2) 0.0280(2) -0.00759(16) 0.00062(18) -0.00121(16) Cl10 0.0309(2) 0.0181(2) 0.0268(2) -0.00863(17) -0.00939(18) -0.00341(17) Cl11 0.0231(2) 0.0231(2) 0.02094(19) -0.00802(16) 0.00560(16) -0.01082(17) Cl12 0.0255(2) 0.0204(2) 0.02077(19) -0.00953(16) 0.00032(16) -0.00839(17) Cl13 0.0251(2) 0.0229(2) 0.01807(19) -0.00791(16) 0.00397(16) -0.00370(17) Cl14 0.0222(2) 0.0257(2) 0.0285(2) -0.00736(18) 0.00790(17) -0.00946(18) Cl15 0.0198(2) 0.0172(2) 0.0259(2) -0.00765(16) -0.00146(16) -0.00571(16) Cl16 0.0206(2) 0.0221(2) 0.01914(19) -0.00584(16) 0.00473(16) 0.00292(16) Cl17 0.0246(2) 0.0193(2) 0.01306(17) -0.00268(15) 0.00217(15) -0.00474(16) Cl18 0.0233(2) 0.0174(2) 0.02106(19) 0.00084(16) -0.00235(16) 0.00296(16) Cl19 0.01687(19) 0.0177(2) 0.02132(19) -0.00429(15) 0.00341(15) 0.00220(15) Cl20 0.0211(2) 0.0214(2) 0.01300(17) -0.00175(15) 0.00235(15) 0.00247(16) O1 0.0190(6) 0.0162(6) 0.0189(6) -0.0063(5) -0.0005(5) -0.0016(5) O2 0.0316(7) 0.0139(6) 0.0268(7) -0.0059(5) -0.0119(6) 0.0013(5) O3 0.0238(6) 0.0146(6) 0.0146(5) -0.0039(5) -0.0005(5) -0.0019(5) O4 0.0189(6) 0.0201(7) 0.0151(6) -0.0020(5) 0.0002(5) 0.0048(5) N1 0.0204(7) 0.0174(8) 0.0216(7) -0.0087(6) 0.0046(6) -0.0029(6) N2 0.0281(8) 0.0159(8) 0.0217(7) -0.0080(6) 0.0047(6) -0.0056(6) C1 0.0148(7) 0.0120(8) 0.0184(8) -0.0041(6) -0.0027(6) 0.0012(6) C2 0.0137(7) 0.0137(8) 0.0189(8) -0.0013(6) -0.0016(6) -0.0021(6) C3 0.0177(8) 0.0113(8) 0.0195(8) -0.0025(6) -0.0059(6) -0.0018(6) C4 0.0206(8) 0.0170(8) 0.0164(7) -0.0061(6) -0.0029(6) 0.0001(7) C5 0.0154(8) 0.0180(9) 0.0193(8) -0.0033(6) 0.0002(6) -0.0024(6) C6 0.0162(8) 0.0139(8) 0.0206(8) -0.0050(6) -0.0029(6) -0.0029(6) C7 0.0180(8) 0.0142(8) 0.0182(8) -0.0045(6) 0.0011(6) -0.0008(6) C8 0.0189(8) 0.0133(8) 0.0195(8) -0.0067(6) 0.0026(6) -0.0024(6) C9 0.0165(8) 0.0185(9) 0.0168(8) -0.0059(6) 0.0013(6) -0.0038(6) C10 0.0156(8) 0.0164(8) 0.0182(8) -0.0029(6) 0.0021(6) 0.0013(6) C11 0.0178(8) 0.0120(8) 0.0204(8) -0.0063(6) 0.0037(6) -0.0032(6) C12 0.0178(8) 0.0165(8) 0.0168(7) -0.0060(6) 0.0009(6) -0.0054(6) C13 0.0167(8) 0.0120(8) 0.0153(7) -0.0015(6) -0.0030(6) -0.0006(6) C14 0.0169(8) 0.0142(8) 0.0128(7) -0.0011(6) -0.0008(6) -0.0028(6) C15 0.0181(8) 0.0134(8) 0.0165(7) -0.0034(6) -0.0038(6) -0.0023(6) C16 0.0193(8) 0.0142(8) 0.0145(7) -0.0029(6) -0.0009(6) -0.0002(6) C17 0.0153(8) 0.0137(8) 0.0177(8) -0.0010(6) 0.0011(6) -0.0025(6) C18 0.0165(8) 0.0113(8) 0.0189(8) -0.0031(6) -0.0039(6) -0.0028(6) C19 0.0135(7) 0.0131(8) 0.0163(7) -0.0033(6) -0.0008(6) -0.0019(6) C20 0.0144(7) 0.0158(8) 0.0158(7) -0.0066(6) 0.0021(6) -0.0010(6) C21 0.0174(8) 0.0144(8) 0.0136(7) -0.0037(6) 0.0013(6) -0.0057(6) C22 0.0160(8) 0.0119(8) 0.0164(7) -0.0015(6) -0.0015(6) -0.0016(6) C23 0.0139(7) 0.0145(8) 0.0166(7) -0.0054(6) 0.0017(6) -0.0030(6) C24 0.0166(8) 0.0149(8) 0.0128(7) -0.0033(6) 0.0023(6) -0.0037(6) C25 0.0204(8) 0.0193(9) 0.0215(8) -0.0069(7) 0.0012(7) 0.0003(7) C26 0.0168(8) 0.0226(9) 0.0169(8) -0.0079(7) 0.0041(6) -0.0039(7) C27 0.0254(9) 0.0160(8) 0.0135(7) -0.0040(6) 0.0061(6) -0.0024(7) C28 0.0245(9) 0.0226(9) 0.0153(8) -0.0029(7) 0.0006(7) 0.0049(7) C29 0.0182(8) 0.0293(10) 0.0168(8) -0.0099(7) 0.0014(6) -0.0048(7) C30 0.0243(10) 0.0371(12) 0.0324(10) -0.0189(9) -0.0020(8) -0.0046(8) C31 0.0426(12) 0.0154(9) 0.0247(9) -0.0054(7) 0.0045(8) -0.0034(8) C32 0.0311(10) 0.0174(9) 0.0205(8) -0.0033(7) 0.0017(7) -0.0034(7) C33 0.0246(9) 0.0217(9) 0.0190(8) -0.0079(7) 0.0058(7) -0.0065(7) C34 0.0235(9) 0.0186(9) 0.0246(9) -0.0112(7) 0.0091(7) -0.0066(7) C35 0.0220(9) 0.0194(9) 0.0305(10) -0.0071(8) 0.0019(7) -0.0009(7) C36 0.0223(9) 0.0237(10) 0.0258(9) -0.0085(7) 0.0012(7) -0.0051(7) C37 0.0364(11) 0.0304(11) 0.0259(9) -0.0081(8) -0.0030(8) -0.0086(9) C38 0.0340(11) 0.0219(10) 0.0427(12) -0.0165(9) 0.0041(9) -0.0074(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C2 1.7250(16) . ? Cl2 C3 1.7259(16) . ? Cl3 C4 1.7296(17) . ? Cl4 C5 1.7268(17) . ? Cl5 C6 1.7307(16) . ? Cl6 C8 1.7254(17) . ? Cl7 C9 1.7240(16) . ? Cl8 C10 1.7204(17) . ? Cl9 C11 1.7229(17) . ? Cl10 C12 1.7264(16) . ? Cl11 C14 1.7262(16) . ? Cl12 C15 1.7248(16) . ? Cl13 C16 1.7285(16) . ? Cl14 C17 1.7276(16) . ? Cl15 C18 1.7350(16) . ? Cl16 C20 1.7227(16) . ? Cl17 C21 1.7229(16) . ? Cl18 C22 1.7197(16) . ? Cl19 C23 1.7250(16) . ? Cl20 C24 1.7218(16) . ? O1 C1 1.3096(19) . ? O2 C7 1.330(2) . ? O2 H2 0.78(3) . ? O3 C13 1.3148(19) . ? O4 C19 1.3359(19) . ? O4 H4 0.83(3) . ? N1 C29 1.336(2) . ? N1 C25 1.344(2) . ? N1 H1 0.91(2) . ? N2 C36 1.336(2) . ? N2 C32 1.342(2) . ? N2 H3 1.00(3) . ? C1 C6 1.413(2) . ? C1 C2 1.415(2) . ? C2 C3 1.399(2) . ? C3 C4 1.395(2) . ? C4 C5 1.390(2) . ? C5 C6 1.395(2) . ? C7 C12 1.402(2) . ? C7 C8 1.404(2) . ? C8 C9 1.390(2) . ? C9 C10 1.393(2) . ? C10 C11 1.398(2) . ? C11 C12 1.391(2) . ? C13 C18 1.409(2) . ? C13 C14 1.412(2) . ? C14 C15 1.391(2) . ? C15 C16 1.394(2) . ? C16 C17 1.392(2) . ? C17 C18 1.393(2) . ? C19 C24 1.402(2) . ? C19 C20 1.406(2) . ? C20 C21 1.390(2) . ? C21 C22 1.397(2) . ? C22 C23 1.398(2) . ? C23 C24 1.393(2) . ? C25 C26 1.382(2) . ? C25 H25A 0.9500 . ? C26 C27 1.401(2) . ? C26 C30 1.498(2) . ? C27 C28 1.399(2) . ? C27 C31 1.496(2) . ? C28 C29 1.371(3) . ? C28 H28A 0.9500 . ? C29 H29A 0.9500 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 C33 1.386(2) . ? C32 H32A 0.9500 . ? C33 C34 1.403(3) . ? C33 C37 1.506(3) . ? C34 C35 1.395(3) . ? C34 C38 1.506(2) . ? C35 C36 1.380(2) . ? C35 H35A 0.9500 . ? C36 H36A 0.9500 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O2 H2 117(2) . . ? C19 O4 H4 117.4(19) . . ? C29 N1 C25 121.71(16) . . ? C29 N1 H1 118.4(15) . . ? C25 N1 H1 119.8(15) . . ? C36 N2 C32 120.90(16) . . ? C36 N2 H3 119.6(16) . . ? C32 N2 H3 119.4(16) . . ? O1 C1 C6 122.32(14) . . ? O1 C1 C2 121.98(14) . . ? C6 C1 C2 115.69(14) . . ? C3 C2 C1 122.17(14) . . ? C3 C2 Cl1 120.51(12) . . ? C1 C2 Cl1 117.32(12) . . ? C4 C3 C2 120.15(14) . . ? C4 C3 Cl2 119.51(13) . . ? C2 C3 Cl2 120.34(12) . . ? C5 C4 C3 119.31(15) . . ? C5 C4 Cl3 119.98(13) . . ? C3 C4 Cl3 120.70(13) . . ? C4 C5 C6 120.15(15) . . ? C4 C5 Cl4 119.91(13) . . ? C6 C5 Cl4 119.94(13) . . ? C5 C6 C1 122.53(15) . . ? C5 C6 Cl5 119.35(12) . . ? C1 C6 Cl5 118.12(12) . . ? O2 C7 C12 125.07(15) . . ? O2 C7 C8 117.43(15) . . ? C12 C7 C8 117.50(15) . . ? C9 C8 C7 121.21(15) . . ? C9 C8 Cl6 120.59(13) . . ? C7 C8 Cl6 118.20(13) . . ? C8 C9 C10 120.59(15) . . ? C8 C9 Cl7 119.71(13) . . ? C10 C9 Cl7 119.70(13) . . ? C9 C10 C11 119.01(15) . . ? C9 C10 Cl8 120.64(13) . . ? C11 C10 Cl8 120.35(13) . . ? C12 C11 C10 120.15(15) . . ? C12 C11 Cl9 120.39(13) . . ? C10 C11 Cl9 119.45(13) . . ? C11 C12 C7 121.52(15) . . ? C11 C12 Cl10 120.53(13) . . ? C7 C12 Cl10 117.95(13) . . ? O3 C13 C18 123.25(14) . . ? O3 C13 C14 121.08(14) . . ? C18 C13 C14 115.61(14) . . ? C15 C14 C13 122.39(15) . . ? C15 C14 Cl11 120.34(12) . . ? C13 C14 Cl11 117.24(12) . . ? C14 C15 C16 120.27(15) . . ? C14 C15 Cl12 119.52(12) . . ? C16 C15 Cl12 120.20(12) . . ? C17 C16 C15 119.02(14) . . ? C17 C16 Cl13 120.42(12) . . ? C15 C16 Cl13 120.55(13) . . ? C16 C17 C18 120.13(14) . . ? C16 C17 Cl14 119.82(12) . . ? C18 C17 Cl14 120.05(12) . . ? C17 C18 C13 122.58(14) . . ? C17 C18 Cl15 119.65(12) . . ? C13 C18 Cl15 117.77(12) . . ? O4 C19 C24 124.99(14) . . ? O4 C19 C20 117.61(14) . . ? C24 C19 C20 117.41(14) . . ? C21 C20 C19 121.00(14) . . ? C21 C20 Cl16 120.89(12) . . ? C19 C20 Cl16 118.11(12) . . ? C20 C21 C22 120.80(14) . . ? C20 C21 Cl17 119.82(12) . . ? C22 C21 Cl17 119.38(12) . . ? C21 C22 C23 119.00(15) . . ? C21 C22 Cl18 120.81(12) . . ? C23 C22 Cl18 120.19(13) . . ? C24 C23 C22 119.81(15) . . ? C24 C23 Cl19 119.96(12) . . ? C22 C23 Cl19 120.23(13) . . ? C23 C24 C19 121.96(14) . . ? C23 C24 Cl20 119.98(12) . . ? C19 C24 Cl20 118.06(12) . . ? N1 C25 C26 121.26(17) . . ? N1 C25 H25A 119.4 . . ? C26 C25 H25A 119.4 . . ? C25 C26 C27 118.19(16) . . ? C25 C26 C30 120.06(17) . . ? C27 C26 C30 121.74(16) . . ? C28 C27 C26 118.68(16) . . ? C28 C27 C31 119.94(17) . . ? C26 C27 C31 121.38(16) . . ? C29 C28 C27 120.30(17) . . ? C29 C28 H28A 119.9 . . ? C27 C28 H28A 119.9 . . ? N1 C29 C28 119.87(16) . . ? N1 C29 H29A 120.1 . . ? C28 C29 H29A 120.1 . . ? C26 C30 H30A 109.5 . . ? C26 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C26 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C27 C31 H31A 109.5 . . ? C27 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C27 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? N2 C32 C33 122.19(18) . . ? N2 C32 H32A 118.9 . . ? C33 C32 H32A 118.9 . . ? C32 C33 C34 117.66(16) . . ? C32 C33 C37 120.02(17) . . ? C34 C33 C37 122.31(16) . . ? C35 C34 C33 118.84(16) . . ? C35 C34 C38 120.03(17) . . ? C33 C34 C38 121.10(17) . . ? C36 C35 C34 120.22(18) . . ? C36 C35 H35A 119.9 . . ? C34 C35 H35A 119.9 . . ? N2 C36 C35 120.18(17) . . ? N2 C36 H36A 119.9 . . ? C35 C36 H36A 119.9 . . ? C33 C37 H37A 109.5 . . ? C33 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C33 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C34 C38 H38A 109.5 . . ? C34 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C34 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.91(2) 1.73(2) 2.6334(19) 177(2) . O2 H2 O1 0.78(3) 1.83(3) 2.5554(17) 154(3) . N2 H3 O3 1.00(3) 1.56(3) 2.5564(19) 172(2) . O4 H4 O3 0.83(3) 1.84(3) 2.6266(16) 158(3) . C25 H25A O2 0.95 2.48 3.193(2) 131.9 . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.467 _refine_diff_density_min -0.341 _refine_diff_density_rms 0.076