Combining hydrogen bonds with coordination chemistry or organometallic 7t-arene chemistry: Strategies for inorganic crystal engineering f

Journal of the Chemical Society, Dalton Transactions

Volumn , Issue 21, 2000, Pages 3855-3867

  Brammer, Lee ^a   Mareque Rivas, Juan C ^a   Reinaldo Atencio, J ^a   Fang, Shiyue ^b   Christopher Pigge, F ^b  

^a UNIVERSITY OF MISSOURI ST LOUIS   (United States)

^b UNIVERSITY OF EDINBURGH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33746974385     PISSN: 1470479X     EISSN: None     Source Type: Journal    
DOI: 10.1039/b004395h     Document Type: Article

References (72)

1. F. A. Cotton, G. Wilkinson, C. A. Murillo and M. Bochman, Advanced Inorganic Chemistry, Wiley, New York, 6th edn., 1999; M. Gerloch and E. C. Constable, Transition Metal Chemistry, VCH, Weinheim, 1994.
2. For example, see: R. Robson, in Comprehensive Siipramolecular Chemistry, Series ed. J. -M. Lehn, Volume eds. J. L. Atwood, J. E. D. Davies, D. D. MacNicol and F. Vôgtle, Pergamon, Oxford, 1996, Vol. 6, pp. 733-755;
3. M. J. Zawarotko, Chem. Soc. Re\:, 1994,23,283;
4. K. A. Hirsch, S. R. Wilson and J. S. Moore, Chem. Eur. J., 1997, 3, 765;
5. K. A. Hirsch, S. R. Wilson and J. S. Moore, Chem. Commun., 1998, 13;
6. L. Carlucci, G. Ciani, D. Proserpio and A. Sironi, J. Am. Chem. Soc., 1995,117,4562;
7. L. Carlucci, G. Ciani, D. Proserpio and A. Sironi, Chem. Commun., 1996, 1393.
8. M. Fujita, in Comprehensive Siipramolecular Chemistry, Series ed. J.-M. Lehn, Volume eds. J. L. Atwood, J. E. D. Davies, D. D. MacNicol and F. Vôgtle, Pergamon, Oxford, 1996, vol. 9, pp. 253282;
9. M. Fujita, Chem. Soc. Rev., 1998, 27, 417;
10. P. J. Stang and B. Olenyuk, Ace. Chem. Res., 1997, 30, 502;
11. C. J. Jones, Chem. Soc. A-., 1998,27,289.
12. J. P. Collman, L. S. Hegedus, J. R. Norton and R. G. Finke, Principles and Applications of Organotransilion Metal Chemistry, University Science Books, Mill Valley, CA, 1987;
13. Ch. Elschenbroich and A. Salzer, Organoinetallics: A Concise Introduction, VCH, Weinheim, 2nd edn., 1992.
14. For example, see: A. Solladie-Cavallo, Polyhedron, 1985, 4, 901;
15. F. Rose-Munch and E. Rose, Curr. Org. Chem., 1999, 3, 445;
16. M. F. Semmelhack, in Comprehensive Organometallic Chemistry II, eds. E. Abel, F. G. A. Stone and G. Wilkinson, Pergamon, Oxford, 1995, vol. 12, p. 979.
17. (a) G. R. Desiraju, Crystal Engineering: The Design of Organic Solids, Elsevier, New York, 1989;
18. (b) M. C. Etter, Ace. Chem. Res., 1990, 23, 120;
19. F. H. Alien, W. D. S. Motherwell, P. R. Raithby, G. P. Shields and R. Taylor, Neu- J. Client., 1999,23,25.
20. For crystal structures of benzoic acid, terephthalic acid isophthalic acid and trimesic acid, see refs. 7a, (7b,c), (7d,e) and 7f, respectively;
21. (a) R. Feld, M. S. Lehman, K. W. Mutr and J. C. Speakman, Z. Kristatlogr., 1981,157, 215;
22. (b) M. Bailey and C. J. Brown, Ada Crystallogr., 1967, 22, 387;
23. A. Domenicano, G. Schultz, I. Hargittai, M. Colapietro, G. Portalone, P. George and C. W. Bock, Struct. Chem., 1990, l, 107;
24. R. Alcala and S. Martinez-Carrera, Ada Crystallogr., Sect. B, 1972, 28, 1671;
25. (e) J. L. Derissen, Acta Crystallogr., Sect. B, 1974, 30, 2764;
26. (f) F. H. Herbstein, in Comprehensive Siipramolecular Chemistry, eds. D. D. MacNicoI, F. Toda and R. Bishop, Pergamon, Oxford, UK, vol. 6, ch, 3, 1996 and references therein.
27. The term siipramoleailar synthon, is hereafter contracted to synthon, see: G. R. Desiraju, Angew. Chew., Int. Ed. Eng!., 1995, 34, 2311;
28. (b) for a review of graph set nomenclature for classifying hydrogen bonds, see: J. Bernstein, R. E. Davis, L. Shimoni and N.-L. Chang, Angeu: Chem., Int. Ed. Engt., 1995,34, 1555.
29. (a) C. B. Aakeröy and A. M. Beatty, Chem. Commun., 1998, 1067;
30. (b) C. B Aakeröy, A. M. Beatty and D. S. Leinen, J. Am. Chem. Soc., 1998, 120, 7383;
31. C. B. Aakeröy and A. M. Beatty, Cryst. Eng., 1998,1,39.
32. (a) F. Jaber, F. Charbonnier, R. Faure and M. Petit-Ramel, Z. Kristallogr., 1994, 209, 536. In related substituted nicotinic acid analogues it has been shown that unpredictability can arise due to silver carboxylate (Ag-O) bond formation. See: (6) C. B. Aakeröy and A. M. Beatty, J. AM. Struct., 1999,474, 91.
33. J. C. Mareque Rivas and L. Brammer, New J. Chem., 1998, 22, 1315.
34. R. Atencio, L. Brammer, S. Fang and F. C. Pigge, Neu- J. Chem., 1999,23,461.
35. See synthesis of [Pt(NC5H5)4p, in Gmelin Handbuch der Anorganische Chemie, Verlag Chemie, Weinheim, 1957, vol. 68D.
36. A. D. Hunter, V. Mozoi and S. T. Tsai, Organometallics, 1992, 11, 2251.
37. A. D. Hunter, L. Shilliday, W. S. Furey and M. J. Zaworotko, Organometallics, 1992, 11, 1550.
38. SHELXTL 5.0, Bruker (Siemens) Analytical X-Ray Instruments, Inc., 1995.
39. (a) G. M. Sheldrick, SADABS, Empirical absorption correction program, University of Göttingen, 1995, based upon the method of Blessing;17 (b) R. H. Blessing, Acta Crystallogr., Sect. A, 1995, 51, 33.
40. A channel of soh-ated chloride ions has recently been reported in the crystal structure of a copper coordination polymer: C. Janiak, T. G. Scharmann, W. Günther, W. Hinrichs and D. Lentz, Chem. Ber., 1996,129,991.
41. (a) See, J. C. Mareque Rivas, Ph.D. Thesis, University of MissouriSt. Louis, 1999 for further details;
42. (b) cell dimensions: o=ll. 9622(1), 6=11.9510(1), c = 45.7593(2) A,/? = 90.073(1)°, K=6541. 8(1) A3 at 213(5) K. Rl =0.069, wR2 = 0.195. Refined as monoclinic, space group 72, with numerous restraints applied.
43. In fact the chloride ligands lie off axis in 1 by 9°, but precisely on axis in 3-7HA""
44. C, H, N elemental analysis of the crystals suggests a formula consistent with 3-8H2O, but the crystallographic model did not suggest inclusion of an additional water molecule.
45. C. B. Aakeröy, A. M. Beatty and D. S. Leinen, Angew. Chem., Int. Ed., 1999,38,1815.
46. V. A. Russell, C. Evans, W. Li and M. D. Ward, Science, 1997, 276, 575.
47. (a) M. A. S. Goher and T. C. W. Mak, Inorg. Chim. Acta, 1985,101, L27;
48. (b) CSD REFCODES: BADHAP, BADXIX, BADKAS, TEXFEH;
49. M. H. Chou, D. J. Szalda, C. Creutz and N. Sutin, Inorg. Chem., 1994,33, 1674;
50. two other published structures not yet in the CSD also contain such amide-amide interactions;'11'24;
51. (e) C. B. Aakeröy, A. M. Beatty, D. S. Leinen and K. R. Lorimer, Chem. Commun., 2000, 935;
52. (f) CSD REFCODES: D1SFIU, FUWGIN, GOKMAU, NUSGOX, NUSGUD;
53. (g) CSD REFCODES: BEXPAU10, BEXPEZ10, ISNARU, JOSDAW01, KULSEG, TANCRU
54. (a) A. D. Burrows, C.-W. Chan, M. M. Chowdhry, J. E. McGrady and D. M. P. Mingos, Chem. Soc. Rer., 1995, 24, 329;
55. (b) A. D. Burrows, S. Menzer, D. M. P. Mingos, A. J. P. White and D. J. Williams, J. Chem. Soc., Dalton Trans., 1997, 4237;
56. M. T. Allen, A. D. Burrows and M. F. Mahon, J. Chem. Soc., Dation Trans., 1999, 215;
57. A. D. Burrows, R. W. Harrington and M. F. Mahon, Cryst EngComm., 2000, 12.
58. A. S. Batsanov, M. J. Begley, M. \V. George, P. Hubberstey, M. Munakata, C. E. Russell and P. H. Wallon, J. Chem. Soc, Dalton Trans., 1999, 4251.
59. Z. Q. Qin, M. C. Jennings, R. J. Puddephatt and K. W. Muir, Cryst EngComm., 2000, 11.
60. D. Braga, F. Grcpioni, P. Sabatino and G. R. Desiraju, Organometallics, 1994, 13, 3532;
61. see also work on [Co(t|s-C5H4COOH)(T]5-C5H4COO)] in D. Braga, L. Maini, M. Polito and F. Grepioni, Organomelallics, 1999, 18, 2577.
62. M. M. Kubicki, P. Richard, B. Gautheron, M. Viotte, S. Toma, M. Hudecek and V. Gajda, J. Organomet. Chan., 1994, 476, 55.
63. D. Braga, F. Grepioni and G. R. Desiraju, Chem. Rev., 1998, 98, 1375;
64. D. Braga and F. Grepioni, Acc. Chem. Re\\, 1997, 30, 81;
65. D. Braga and F. Grepioni, J. Chem. Soc., Dation Trans., 1999, 1.
66. J. C. Mareque Rivas and L. Brammer, Coord. Chem. Re\\, 1999,183, 43.
67. This nomenclature summarizes the sequence of hydrogen bond donor (D) and acceptor (A) groups on each of the two interacting molecules, see réf. 25(a) for more details.
68. A. J. Bondi, J. Cltcin. Pliys., 1964, 68,441.
69. S. Valiyaveetil, V. Enkelmann and K. Müllen, J. Client. Soc., Client. Commun., 1994, 2097.
70. F. H. Herbstein and R. E. Marsh, Acta Crystallogr., Sect. B, 1977, 33,2358;
71. S. V. Kolotuchin, E. E. Fenlon, S. R. Wilson, C. J. Loweth and S. C. Zimmcrman, Angen: Chem., Im. Ed. Eng!., 1995, 34, 2654.
72. G. R. Desiraju and T. Steiner, The Weak Hydrogen Bond, Oxford University Press, London, 1999.