Formation of a three-dimensional hydrogen-bonding network by self-assembly of the Cu^II complex of a semi-bidentate Schiff base

Abstract

Three-dimensional hydrogen-bonding networks have been found in the crystal structure of the Cu^II complex of the semi-N,O-bidentate Schiff base L₁₄, having both hydrogen donor and acceptor sites. The infinite one-dimensional channels and cavities and the helical structure are presented as a result of the complementary intermolecular hydrogen-bonding interaction (–SO₂ · · · H₂N–). Molecular mechanics calculations show the difference between calculated and X-ray structures of the Cu^II–L₁₄ complex.

References

1. W. Saenger, Angew. Chem., Int. Ed. Engl., 1980, 19, 344; G. Wenz, Angew. Chem., Int. Ed. Engl., 1994, 33, 803; N. Yoshida and K. Hayashi, J. Chem. Soc., Perkin Trans. 2, 1994, 1285; N. Yoshida and Y. Fujita, J. Phys. Chem., 1995, 99, 3671; N. Yoshida, J. Chem. Soc., Perkin Trans. 2, 1995, 2249; D. M. Davies and M. E. Deary, J. Chem. Soc., Perkin Trans. 2, 1995, 1287; M. D. Johnson and J. G. Bernard, Chem. Commun., 1996, 185; P. Bungnon, P. G. Lye, A. A. Hamdan and A. E. Merbach, Chem. Commun., 1996, 2787.
2. N. Yoshida, N. Ito and K. Ichikawa, J. Chem. Soc., Perkin Trans. 2, 1996, 965; A. V. Eliseev and H.-J. Schneider, J. Am. Chem. Soc., 1994, 116, 6081.
3. (a) C. B. Aakeröy and K. P. Seddon, Chem. Soc. Rev., 1993, 22, 397; (b) J. C. MacDonald and G. M. Whitesides, Chem. Rev., 1994, 94, 2383; (c) M. J. Zaworotko, Chem. Soc. Rev., 1994, 23, 283.
4. (a) J.-M. Lehn, Science, 1985, 227, 849; (b) J. S. Moore and S. Lee, Chem. Ind., July 1994, 556; (c) D. D. MacNicol, J. J. McKendrick and D. R. Wilson, Chem. Soc. Rev., 1978, 7, 65; (d) H. Hart, L.-T. W. Lin and D. L. Ward, J. Am. Chem. Soc., 1984, 106, 4043; (e) E. Weber, W. Seichter and I. Goldberg, Chem. Ber., 1990, 123, 811.
5. (a) M. Simard, D. Su and J. D. Wuest, J. Am. Chem. Soc., 1991, 113, 4696; (b) M. R. Ghadiri, J. R. Granja, R. A. Milligan, D. E. McRee and N. Khazanovich, Nature (London), 1993, 366, 324.
6. G. R. Desiraju, Angew. Chem., Int. Ed. Engl., 1995, 34, 2311; G. R. Desiraju, Crystal Engineering: The Design of Organic Solids, Elsevier, Amsterdam, 1989.
7. J.-M. Lehn, M. Mascal, A. DeCian and J. Fischer, J. Chem. Soc., Perkin Trans. 2, 1992, 461.
8. S. V. Kolotuchin, E. E. Fenlon, S. R. Wilson, C. J. Loweth and S. C. Zimmerman, Angew. Chem., Int. Ed. Engl., 1995, 34, 2654.
9. R. E. Melendez, C. V. K. Sharma, M. J. Zaworotko, C. Bauer and R. D. Rogers, Angew. Chem., Int. Ed. Engl., 1996, 35, 2213; C. M. White, M. F. Gonzalez, D. A. Bardwell, L. H. Rees, J. C. Jeffery, M. D. Ward, N. Armaroli, G. Calogero and F. Barigelleti, J. Chem. Soc., Dalton Trans., 1997, 727.
10. C. K. Prout and J. D. Wright, Angew. Chem., Int. Ed. Engl., 1968, 7, 659.
11. V. R. Pedireddi, W. Jones, A. P. Chorlton and R. Docherty, Chem. Commun., 1996, 997.
12. J. Yang, E. Fan, J. Geib and A. D. Hamilton, J. Am. Chem. Soc., 1993, 115, 5314.
13. A. D. Burrows, C.-W. Chan, M. M. Chowdhry, J. E. McGrady and D. M. P. Mingos, Chem. Soc. Rev., 1995, 24, 329.
14. M. P. Byrn, C. J. Curtis, S. I. Khan, P. A. Sawin, R. Turumi and C. E. Strouse, J. Am. Chem. Soc., 1990, 112, 1865; B. F. Hoskins and R. Robson, J. Am. Chem. Soc., 1990, 112, 1546; B. F. Abrahams, B. F. Hoskins, D. M. Michail and R. Robson, Nature (London), 1994, 369, 727.
15. (a) A. D. Burrows, D. M. P. Mingos, A. J. P. White and D. J. Williams, Chem. Commun., 1996, 97; (b) C.-W. Chan, D. M. P. Mingos, A. J. P. White and D. J. Williams, Chem. Commun., 1996, 81.
16. I. Goldberg, Mol. Cryst. Liq. Cryst., 1996, 278, 57.
17. (a) N. Yoshida and M. Fujimoto, Bull. Chem. Soc. Jpn., 1976, 49, 1557; (b) A. J. Atkins, D. Black, A. J. Blake, A. M. Becerra, S. Parsons, L. R.-Ramirez and M. Schröder, Chem. Commun., 1996, 457.
18. J. B. Fenn, M. Mann, C. K. Meng, S. F. Wong and C. M. Whitehouse, Science, 1989, 246, 64; V. Katta, S. K. Chowdhury and B. T. Chait, J. Am. Chem. Soc., 1990, 112, 5348; F. Bitsch, C. O. Dietrich-Buchecker, A. K. Klémiss, J.-P. Sauvage and A. Van Dorsselaer, J. Am. Chem. Soc., 1991, 113, 4023; J. T. Stults and J. C. Marsters, Rapid Commun. Mass Spectrom., 1991, 5, 359.
19. K. Wang, X. Han, R. W. Gross and G. W. Gokel, J. Am. Chem. Soc., 1995, 117, 7680; K. C. Russell, E. Leize, A. V. Dorsselaer and J.-M. Lehn, Angew. Chem., Int. Ed. Engl., 1995, 34, 209.
20. The aminophenyl sulfone moiety is twisted out of the plane of the Schiff base unit. The steric energy (E_steric) for the optimized structure of L₁₄ was evaluated to be –17.8702 kcal mol^–1.
21. Atomic coordinates, bond lengths and angles, and thermal parameters have been deposited at the Cambridge Crystallographic Data Centre (CCDC). For details of the deposition scheme, see ‘Instructions for authors’, J. Chem. Soc., Perkin Trans. 2, 1997, Issue 1. Any request to the CCDC for this material should quote the full literature citation and the reference number 100082.
22. The energy terms (kcal mol^–1) for the MM-2 force field structure are bond stretch (E_bs), bond angle (E_ba), stretch bend (E_sb), dihedral angle (E_da), improper torsion (E_it), van der Waals (E_vdw), electrostatic (E_e), and hydrogen bond (E_hb)E_tot=–227.34 kcal mol^–1(E_bs= 1.42, E_ba= 12.40, E_sb= 0.001, E_da=–40.62, E_it= 0.24, E_vdw= 15.91, E_e=–13.58, E_hb=–3.11 kcal mol^–1).
23. For the parameters, see the following reference: N. L. Allinger, J. Am. Chem. Soc., 1977, 99, 8127 Transition metals are not as easy to parametrize as first- and second-row atoms. Energy minimization calculations were performed with the use of Tektronix CAChe System, Version 3.5 in conjunction with the force field MM-2 with additional metal parameters for CAChe (van der Waals parameters for the Cu^IIion, bond-angle parameters for Cu^II⋯ N=C, Cu^II⋯ N–C and Cu^II⋯ O–C and bond stretch parameters for Cu^II⋯ N and Cu^II⋯ O).
24. The energy terms (kcal mol^–1) for the X-ray crystal structure of 1: E_tot= 271.01 kcal mol^–1(E_bs= 234.31, E_ba= 32.48, E_sb= 0.048, E_da=–15.71, E_it= 0.034, E_vdw= 23.91, E_e=–1.522, E_hb=–2.54 kcal mol^–1). The energy term E_bs is quite different for the MM-2 force-field structure and X-ray crystal structure.
25. X. Chen, S. Zhan, C. Hu, Q. Meng and Y. Liu, J. Chem. Soc., Dalton Trans., 1997, 245.
26. M. Nishio, Y. Umezawa, M. Hirota and Y. Takeuchi, Tetrahedron, 1995, 51, 8665; H. Adams, F. J. Carver, C. A. Hunter, J. C. Morales and E. M. Seward, Angew. Chem., Int. Ed. Engl., 1996, 35, 1542; P. R. Ashton, E. J. T. Chrystal, P. T. Glink, S. Menzer, C. Schiavo, N. Spencer, J. F. Stoddart, P. A. Tasker, A. J. P. White and D. J. Williams, Chem. Eur. J., 1996, 2, 709.
27. N. Yoshida and M. Fujimoto, Bull. Chem. Soc. Jpn., 1980, 53, 101; N. Yoshida, A. Furusaki and M. Fujimoto, J. Chem. Soc., Dalton Trans., 1991, 453 As for the weak hydrogen bond, see T. Steiner, Chem. Commun., 1997, 727.
28. M. Mascal, Contemp. Org. Synth., 1994, 1, 31.
29. G. A. Jeffrey and W. Saenger, Hydrogen Bonding in Biological Structures, Springer-Verlag, Berlin, 1991, ch. 8.
30. C. Davies, R. F. Langler, C. V. Krishnamohan and M. J. Zaworotko, Chem. Commun., 1997, 567.
31. The solvent DMF may control the packing among the structural units formulated (MgPPS·4DMF)₂; dimer (C–H ⋯ N distance: 2.49, 2.85 and 3.05 Å). M. Izumi, K. Ichikawa, M. Suzuki, I. Tanaka and K. W. Rudzinski, Inorg. Chem., 1995, 34, 5388.
32. O. Ermer and A. Eling, J. Chem. Soc., Perkin Trans. 2, 1994, 925; J. H. Loehlin, M. C. Etter, C. Gendreau and E. Cervasio, Chem. Mater., 1994, 6, 1218.
33. S. Hanessian, M. Simard and S. Roelens, J. Am. Chem. Soc., 1995, 117, 7630.