Crystal engineering and correspondence between molecular and crystal structures. Are 2- and 3-aminophenols anomalous?

Journal of the American Chemical Society

Volumn 119, Issue 15, 1997, Pages 3477-3480

  Allen, Frank H ^a   Hoy, Vanessa J ^b   Howard, Judith A K ^b   Thalladi, Venkat R ^c   Desiraju, Gautam R ^c   Wilson, Chick C ^d   McIntyre, Garry J ^e  

^a CAMBRIDGE CRYSTALLOGRAPHIC DATA CENTRE   (United Kingdom)

^b DURHAM UNIVERSITY   (United Kingdom)

^c UNIVERSITY OF HYDERABAD   (India)

^d RUTHERFORD APPLETON LABORATORY   (United Kingdom)

^e INSTITUT LAUE LANGEVIN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINOPHENOL; 3 AMINOPHENOL;

ARTICLE; CRYSTAL STRUCTURE; CRYSTALLIZATION; IN VITRO STUDY; X RAY DIFFRACTION;

EID: 0030925337     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja964254p     Document Type: Article

References (32)

1. (a) Aakeröy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 397.
2. (b) Fan, E.; Vicent, C.; Geib, S. J.; Hamilton, A. D. Chem. Mater. 1994, 6, 1113.
3. (c) MacDonald. J. C; Whitesides, G. M. Chem. Rev. 1994, 94, 2383.
4. (d) Ball, P. New Sci. 1995 (Aug 5 issue), 40.
5. (a) Ermer, O.; Eling, A. J. Chem. Soc., Perkin Trans. 2, 1994, 925.
6. (b) Hanessian, S.; Gomtsyan, A.; Simard, M.; Roelens, S. J. Am. Chem. Soc. 1994, 116, 4495.
7. (c) Hanessian, S.; Simard, M.; Roelens, S. J. Am. Chem. Soc. 1995, 117, 7630.
8. (a) Desiraju, G. R. Crystal Engineering: The Design of Organic Solids; Elsevier: Amsterdam, 1989.
9. (b) Desiraju, G. R.; Gavezzotti, A. J. Chem. Soc., Chem. Commun. 1989, 621.
10. Borman, S. Chem. Eng. News 1995 (Dec 11 issue), 33.
11. (a) Korp, J. D.; Bernal, I.; Aven, L.; Mills, J. L. J. Cryst. Mol. Struct. 1981, 11, 117.
12. (b) de Rango, C.; Brunie, S.; Tsoucaris, G.; Declercq, J. P.; Germain, G. Cryst. Struct. Commun. 1974, 3, 485.
13. Viswamitra, M. A.; Radhakrishnan, R.; Bandekar, J.; Desiraju, G. R. J. Am. Chem. Soc. 1993, 115, 4868.
14. (a) Wilson, C. C. J. Mol. Struct., in press.
15. (b) Allen, F. H.; Howard, J. A. K.; Hoy, V. J.; Desiraju, G. R.; Reddy, D. S.; Wilson, C. C. J. Am. Chem. Soc. 1996, 118, 4081.
16. Sheldrick, G. M. SHELXL-93, A program for the refinement of single crystal diffraction data. University of Göttingen, Germany, 1993.
17. 2 = 0.0654, Gof = 1.477, all atoms anisotropic.
18. Wilkinson, C.; Khamis, H. W.; Stansfield, R. F. D.; McIntyre, G. J. J. Appl. Cryst. 1988, 21, 471.
19. Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer: Berlin, 1991.
20. Allen, F. H.; Davies, J. E.; Galloy, J. J.; Johnson, O.; Kennard, O.; Macrae, C. F.; Watson, D. G. J. Chem. Inf. Comput. Sci. 1991, 31, 204.
21. Zorkii, P. M.; Zorkaya, O. N. J. Struct. Chem. 1995, 36, 704.
22. Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2311.
23. (a) Robertson, J. M. Proc. R. Soc. London, 1951, A207, 101.
24. (b) Kitaigorodskii, A. I. Molecular Crystal and Molecules; Academic Press: New York, 1973.
25. (c) Williams, D. E. J. Chem. Phys. 1965, 45, 3770.
26. (d) Burley, S. K.; Petsko, G. A. J. Am. Chem. Soc. 1986, 108, 7995.
27. (e) Gavezzotti, A.; Desiraju, G. R. Acta Crystallogr. 1988, B44, 427.
28. Gavezzotti, A. Chem. Phys. Lett. 1988, 161, 67.
29. Hanton, L. R.; Hunter, C. A.; Purvis, D. H. J. Chem. Soc., Chem. Commun. 1992, 1134.
30. Kashino, S.; Tomita, M.; Haisa, M. Acta Crystallogr. 1988, C44, 730.
31. The crystal structure of 4-chloro-2-aminophenol has been determined to a low accuracy (Ashfaquzzaman, S.; Pant, A. K. Acta Crystallogr. 1979, B35, 1394) and so is not discussed in any further detail here.
32. Note that two of the cell edges of 2 and 4 are nearly identical. Cell parameters of 4: a = 7.7803 Å, b = 22.901 Å, c = 7.5962 Å, α = β= γ = 90°.