The change in the X-ray dipole moment as a quantitative measure of the polarizing effect of the molecular environment: application to a complex of p-amino-p′-nitrobiphenyl with triphenylphosphine oxide

Abstract

The X-ray determined dipole moment has been used to assess the strength of the electrostatic interactions in a new complex of p-amino-p’-nitrobiphenyl, which is a suitable candidate for photo-crystallographic studies of transient species.

References

1. P. Coppens, D. V. Fomitchev, M. D. Carducci and K. Culp, J. Chem. Soc., Dalton Trans., 1998, 865.
2. Y. Zhang, G. Wu, B. R. Wenner, F. V. Bright and P. Coppens, Cryst. Eng., 1999, 2, 1.
3. T. J. Brett, S. Liu, P. Coppens and J. J. Stezowski, Chem. Commun., 1999, 551.
4. P. Piotrowiak, R. Kobetic, T. R. Schatz and G. Strati, J. Phys. Chem., 1995, 99, 2250.
5. J. Czekalla, W. Liptay and K. O. Meyer, Ber. Bunsen-Ges. Phys. Chem., 1963, 67, 465; M. N. Paddon-Row, A. M. Oliver, J. W. Warman, K. J. Smit, M. P. de Haas, H. Oevering and J. W. Verhoeven, J. Phys. Chem., 1988, 92, 6958.
6. C. Gatti, V. R. Saunders and C. Roetti, J. Chem. Phys., 1994, 101, 10 686.
7. S. T. Howard, M. B. Hursthouse, C. W. Lehmann, P. R. Mallinson and C. S. Frampton, J. Chem. Phys., 1992, 97, 2962.
8. Yu. A. Abramov, A. V. Volkov and P. Coppens, Chem. Phys. Lett., 1999, 311, 81.
9. M. C. Etter and P. W. Baures, J. Am. Chem. Soc., 1988, 110, 639.
10. SADTLER standard UV spectrum, 1962, NO. 4852UV.
11. K. A. Al-Hassan and M. A. El-Bayoumi, Chem. Phys. Lett., 1987, 138, 594.
12. Crystals of PANB/TPPO were grown by slow evaporation (four days) from an acetone solution of PANB (TCI America) and excess TPPO (Aldrich). Large transparent specimens of up to 0.5 × 1.0 × 1.0 cm³ were obtained, with an orange red color less intense than that of pure PANB. ¹H NMR indicated a 1∶1 ratio of the two components.
13. Crystal data for (C₁₈H₁₅OP)(C₁₂H₁₀N₂O₂): M= 492.49, triclinic, a= 9.2719(8), b= 10.4330(10), c= 14.4569(11)Å, α= 106.122(4), β= 107.714(5), γ= 94.691(4)°, U= 1258.47(19)ų, T= 90(1) K, space group P1̄(no. 2), Z= 2, D_c= 1.300 g cm^–3, crystal size 0.13 × 0.25 × 0.25 mm³, µ(Mo-Kα)= 0.144 mm^–1, 89125 reflections, 13140 unique reflections (R_int= 0.0421), 2θ_max= 105.54°, GOF = 0.865, R(F)= 0.033, for 9163 reflections with F_o > 4 σ(F_o), Rw(F²)= 0.084 for all reflections, 426 parameters. Data were collected by the oscillation method on a Bruker SMART 1K CCD diffractometer. Reflections were integrated by the SAINT program and scaled by SORTAV. The structure was solved by direct methods with XS in SHELXTL (SHELXTL NT Version 5.10, G. M. Sheldrick, Program for the Refinement of Crystal Structures, University of Göttingen, Germany, 1997), and refined with XL. All the non-hydrogen atoms were refined anisotropically. Positions of hydrogen atoms were located from the difference Fourier map and refined isotropically, each with its own isotropic temperature parameters. No constraint was applied in the refinement. CCDC 182/1464. See http://www.rsc.org.suppdata/cc/1999/2425/ for crystallographic data in .cif format.
14. N1⋯O3^I= 3.055(1)Å, ∠N1–H1A⋯O3^I= 146.6(1.2)°, (I = 1+x, y, 1 +z); N1⋯O3^II= 2.931(1)Å, ∠N1–H1B⋯O3^II= 176.0(1.3)°, (II = 2 –x, –y, 1 –z).
15. M. Y. Antipin, A. I. Akhmedov, Y. T. Struchkov, E. I. Matrosov and M. I. Kabachnik, Zh. Strukt. Khim., 1983, 24, 86.
16. G. Ferguson and C. Glidewell, J. Chem. Soc., Perkins Trans. 2, 1988, 2129.
17. C15⋯O2^III= 3.447(1)Å, ∠C15–H15⋯O2^III= 167.4(1.0)°, (III = 1 +x, y, z).
18. E. M. Graham, V. M. Miskowski, J. W. Perry, D. R. Coulter, A. E. Stiegman, W. P. Schaefer and R. E. Marsh, J. Am. Chem. Soc., 1989, 111, 8771.
19. A. V. Volkov, G. Wu and P. Coppens, J. Synchrotron Radiat., 1999, 6, 1007.
20. HF, 6311G** basis set, Jaguar 3.5, Schrödinger, Inc. Portland, OR, 1998.
21. O. Bastiansen, Acta Chem. Scand., 1949, 3, 408.
22. C. P. Brock and R. P. Minton, J. Am. Chem. Soc., 1989, 111, 4586.
23. T. Koritsanszky, S. Howard, T. Richter, Z. Su, P. R. Mallinson, N. K. Hansen, XD-A Computer Program Package for Multipole Refinement and Analysis of Electron Densities from Diffraction Data, Free University Berlin, Germany, 1995.
24. X–H distances taken from International Tables for Crystallography, Vol. C, were used for all C–H and N–H bonds. The κ′ restricted multipole model (KRMM)⁸ was applied, R(F)= 0.019, Rw(F²)= 0.041.