Skip to main content
Log in

Polymorphism of dianilinegossypol

  • Structure of Organic Compounds
  • Published:
Crystallography Reports Aims and scope Submit manuscript

Abstract

Polymorphs of dianilinegossypol are obtained by selecting the precipitation medium and the crystallization temperature. Four dianilinegossypol polymorphs are found. Two solvate forms and three polymorphic modifications of dianilinegossypol are prepared from an acetone solution by varying the crystallization temperature from room temperature to 6°C. The crystal structures of the P1, P2, and P4 polymorphs are determined. The P1 and P2 polymorphs are characterized by the same hydrogen-bond system, but their crystal structures differ in the mode of packing of layers formed by dimers of dianilinegossypol molecules. In the P4 polymorph, homochiral hydrogen-bonded dianilinegossypol molecules form trimers. This mode of H-agglomeraton of dianilinegossypol molecules is characteristic only of the P4 polymorph.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. T. Laird, in Comprehensive Medicinal Chemistry, Ed. by P. D. Kennewell (Pergamon Press, Oxford, 1990), Vol. 1, p. 321.

    Google Scholar 

  2. J. K. Haleblian, J. Pharm. Sci. 64, 1269 (1975).

    Google Scholar 

  3. S. R. Byrn, Solid-State Chemistry of Drugs (Academic, New York, 1982).

    Google Scholar 

  4. K. Sato, J. Phys. D 26, B77 (1993).

    Article  ADS  Google Scholar 

  5. W. C. McCrone, in Physics and Chemistry of the Organic Solid State, Ed. by D. Fox, M. M. Labes, and A. Weissberger (Interscience, New York, 1965), p. 726.

    Google Scholar 

  6. D. Giron, Thermochim. Acta 248, 1 (1995).

    Article  Google Scholar 

  7. W. H. Ojala and M. C. Etter, J. Am. Chem. Soc. 114, 10288 (1992).

    Article  Google Scholar 

  8. R. J. Daley, S. J. Maginn, S. J. Andrews, et al., J. Chem. Soc., Faraday Trans. 90, 1003 (1994).

    Google Scholar 

  9. H. G. Gallagher and J. N. Sherwood, J. Chem. Soc., Faraday Trans. 92(12), 2107 (1996).

    Article  Google Scholar 

  10. M. Kitamura, S. Ueno, and K. Sato, in Crystallization Processes, Ed. by H. Othaki (Wiley, Chichester, 1998), Vol. 3, p. 99.

    Google Scholar 

  11. A. L. Markman and V. P. Rzhekhin, Gossypol and Its Deriviatives (Pishchevaya Promyshlennost', Moscow, 1965).

    Google Scholar 

  12. E. P. Clark, J. Biol. Chem. 75, 725 (1927).

    Google Scholar 

  13. K. N. Campbell, R. C. Morris, and R. Adams, J. Am. Chem. Soc. 59, 1723 (1937).

    Google Scholar 

  14. L. Marchlewski, J. Prakt. Chem. 60(9), 84 (1899).

    Google Scholar 

  15. R. Adams, T. A. Geismann, and J. D. Edwards, Chem. Rev. 60, 555 (1960).

    Article  Google Scholar 

  16. J. D. Edwards, J. Am. Chem. Soc. 47, 441 (1957).

    Google Scholar 

  17. Ch. H. Boathner, in Cottonseed and Cottonseed Products. Their Chemistry and Chemical Technology, Ed. by A. E. Bailey (Interscience, New York, 1948), p. 213.

    Google Scholar 

  18. K. Chander and T. R. Seshardi, J. Sci. Ind. Res., Sect. B 17, 279 (1958).

    Google Scholar 

  19. L. E. Castillion, C. M. Hall, and Ch. H. Boathner, J. Am. Chem. Soc. 25, 233 (1948).

    Google Scholar 

  20. M. Gdaniec, B. T. Ibragimov, and S. A. Talipov, in Comprahensive Supramolecular Chemistry, Vol. 6: Solid State. Supramolecular Chemistry: Crystal Engineering, Ed. by D. D. MacNicol, E. Toda, and R. Bishop (Pergamon, Oxford, 1996), p. 117.

    Google Scholar 

  21. B. T. Ibragimov and S. A. Talipov, J. Inclusion Phenom. Mol. Recognit. Chem. 17, 325 (1994).

    Google Scholar 

  22. K. M. Beketov, B. T. Ibragimov, and S. A. Talipov, Khim. Farmats. 1, 16 (1996).

    Google Scholar 

  23. B. T. Ibragimov, K. M. Beketov, S. A. Talipov, and T. F. Aripov, J. Inclusion Phenom. Mol. Recognit. Chem. 29, 23 (1997).

    Article  Google Scholar 

  24. K. M. Beketov, B. T. Ibragimov, and S. A. Talipov, Khim. Prir. Soedin. 30, 58 (1994).

    Google Scholar 

  25. K. M. Beketov, B. T. Ibragimov, S. A. Talipov, and T. F. Aripov, J. Inclusion Phenom. Mol. Recognit. Chem. 28, 141 (1997).

    Article  Google Scholar 

  26. K. M. Beketov, B. T. Ibragimov, S. A. Talipov, et al., J. Inclusion Phenom. Mol. Recognit. Chem. 27, 105 (1997).

    Article  Google Scholar 

  27. G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr. 46, 467 (1990).

    Article  Google Scholar 

  28. G. M. Sheldrick, SHELXL93: Program for the Refinement of Crystal Structures (Univ. of Göttingen, Germany, 1993).

    Google Scholar 

  29. Siemens XP: Molecular Graphics Program, Version 5.03 (Siemens Analytical X-ray Instruments Inst., Madison, Wisconsin, 1994).

Download references

Author information

Authors and Affiliations

Authors

Additional information

__________

Translated from Kristallografiya, Vol. 48, No. 4, 2003, pp. 691–698.

Original Russian Text Copyright © 2003 by Beketov, Talipov, Ibragimov, Praliev, Aripov.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Beketov, K.M., Talipov, S.A., Ibragimov, B.T. et al. Polymorphism of dianilinegossypol. Crystallogr. Rep. 48, 641–648 (2003). https://doi.org/10.1134/1.1595193

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1134/1.1595193

Keywords

Navigation