Supramolecular synthons in crystal engineering. 4. Structure simplification and synthon interchangeability in some organic diamondoid solids

Journal of the American Chemical Society

Volumn 118, Issue 17, 1996, Pages 4090-4093

  Shekhar Reddy, D ^a   Craig, Donald C ^b   Desiraju, Gautam R ^a  

^a UNIVERSITY OF HYDERABAD   (India)

^b UNIVERSITY OF NEW SOUTH WALES   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOBROMINE DERIVATIVE;

ARTICLE; CRYSTALLIZATION; CRYSTALLOGRAPHY; DRUG STRUCTURE;

EID: 0029920165     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953373m     Document Type: Article

References (28)

1. For Part 3 of this series, see: Reddy, D. S.; Ovchinnikov, Y. E ; Shishkin, O. V.; Struchkov, Y. T., Desiraju, G. R. J. Am Chem. Soc. 1996, 118, 4085.
2. Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2311.
3. Desiraju, G. R. Crystal Engineering: The Design of Organic Solids, Elsevier: Amsterdam, 1989.
4. (a) Ermer, O. J. Am. Chem. Soc. 1988, 110, 3747.
5. (b) Ermer, O.; Eling, A. Angew. Chem., Int. Ed. Engl. 1988, 27, 829.
6. (c) Ermer, O.; Lindenberg, L. Helv. Chem. Acta. 1988, 71, 1084.
7. (d) Ermer, O.; Lindenberg, L. Helv. Chim. Acta. 1991, 74, 825.
8. Wuest, J. D. In Mesomolecules. From Molecules to Materials; Mendenhall, G. D., Greenberg, A., Liebman, J. R. Eds.; SEARCH Series Volume 1: Chapman and Hall: New York, 1995; pp 107-131.
9. Zaworotko, M. Chem. Soc. Rev. 1994, 23, 283 and the references cited therein.
10. Abrahams, B. F.; Hoskins, B F.; Micaile, D. M.; Robson, R. Nature 1994, 369, 727.
11. Reddy, D. S.; Cratg, D. C.; Rae, A. D.; Desiraju, G. R. J. Chem. Soc. Chem. Commun. 1993, 1737.
12. Reddy, D. S.; Craig, D. C.; Desiraju, G. R. J. Chem. Soc., Chem. Commun. 1994, 1457.
13. Main, P.; Fiske, S. J.; Hull, S. E.; Lessinger, L.; Germain, G.; Declercq, J. P.; Woolfson, M. M. MULTAN80. A system of Computer Programs for the Automatic Solution of Crystal Structures from X-Ray Diffraction Data, University of York, England, and Louvain, Belgium, 1980.
14. Rae, A. D. RAELS89: A Comprehensive Constrained Least Squares Refinement Program, University of New South Wales, Kensington, 1989
15. For all crystal structure data for 6 and 8, see the supporting information. 6: 14. a = 12.713(2) Å, c = 7.114(2) Å, 8: 14̄, a = 12.638(2) Å, c = 7.298(2) Å.
16. Jones, W.; Theochans, C R.; Thomas, J. M.; Desiraju, G. R. J. Chem. Soc., Chem. Commun. 1983, 1443.
17. Robbins, A.; Jeffrey, G. A.; Chesick, J. P.; Donohue, J.; Cotton, F. A.; Frenz, B. A.; Murillo, C. A. Acta. Crystallogr. 1975, B31, 2395.
18. The presence of synthon VI in all the systems here could well be the reason for their facile crystallization from solution. For a description of this so-called "phenyl factor", see: Dance, I. G. In Perspectives in Supramolecular Chemistry: The Crystal as a Supramolecular Entity; Desiraju, G. R., Ed.; Wiley: Chichester, 1996: Vol. 2. See also: Dance, I. G.; Scudder, M. J. Chem. Soc., Chem. Commun. 1995, 1039.
19. The presence of synthon VI in all the systems here could well be the reason for their facile crystallization from solution. For a description of this so-called "phenyl factor", see: Dance, I. G. In Perspectives in Supramolecular Chemistry: The Crystal as a Supramolecular Entity; Desiraju, G. R., Ed.; Wiley: Chichester, 1996: Vol. 2. See also: Dance, I. G.; Scudder, M. J. Chem. Soc., Chem. Commun. 1995, 1039.
20. Desiraju, G. R. J. Mol. Struct. 1996, 374, 191
21. Kitaigorodskii, A. I. Molecular Crystals and Molecules: Academic: New York, 1973.
22. However, inherent in Kitaigorodskii's work is an aufbau principle which can be thought of as a staging process for the assembly of molecules in the crystal. See: Perlstein, J.V. Am. Chem. Soc. 1994, 116, 11420. For a recent elegant description of the topological approach to molecular crystals, see: Belsky, V. K.; Zorkaya, O. N.; Zorky, P. M. Acta Crystallogr. 1995, A51, 473.
23. However, inherent in Kitaigorodskii's work is an aufbau principle which can be thought of as a staging process for the assembly of molecules in the crystal. See: Perlstein, J.V. Am. Chem. Soc. 1994, 116, 11420. For a recent elegant description of the topological approach to molecular crystals, see: Belsky, V. K.; Zorkaya, O. N.; Zorky, P. M. Acta Crystallogr. 1995, A51, 473.
24. Lehn, J.-M. In Perspectives in Supramolecular Chemistry: The Lock and Key Principle: Behr, J.-P., Ed.; Wiley: Chichester. 1995. Vol. 1, p 307.
25. (a) Wells, A. F. Structural Inorganic Chemistry: Oxford University Press: Oxford, 1975.
26. (b) Reddy, D S.; Craig, D. C.; Desiraju, G. R. J. Chem. Soc., Chem. Commun. 1995, 339.
27. (c) Ermer, O.; Robke, C. Angew. Chem., Int. Ed. Engl. 1994, 33, 1755.
28. (d) Gardner, G. B.; Venkataraman, D.; Moore, J. S.; Lee, S. Nature 1995, 374, 792.