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.
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References
T. Laird, in Comprehensive Medicinal Chemistry, Ed. by P. D. Kennewell (Pergamon Press, Oxford, 1990), Vol. 1, p. 321.
J. K. Haleblian, J. Pharm. Sci. 64, 1269 (1975).
S. R. Byrn, Solid-State Chemistry of Drugs (Academic, New York, 1982).
K. Sato, J. Phys. D 26, B77 (1993).
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.
D. Giron, Thermochim. Acta 248, 1 (1995).
W. H. Ojala and M. C. Etter, J. Am. Chem. Soc. 114, 10288 (1992).
R. J. Daley, S. J. Maginn, S. J. Andrews, et al., J. Chem. Soc., Faraday Trans. 90, 1003 (1994).
H. G. Gallagher and J. N. Sherwood, J. Chem. Soc., Faraday Trans. 92(12), 2107 (1996).
M. Kitamura, S. Ueno, and K. Sato, in Crystallization Processes, Ed. by H. Othaki (Wiley, Chichester, 1998), Vol. 3, p. 99.
A. L. Markman and V. P. Rzhekhin, Gossypol and Its Deriviatives (Pishchevaya Promyshlennost', Moscow, 1965).
E. P. Clark, J. Biol. Chem. 75, 725 (1927).
K. N. Campbell, R. C. Morris, and R. Adams, J. Am. Chem. Soc. 59, 1723 (1937).
L. Marchlewski, J. Prakt. Chem. 60(9), 84 (1899).
R. Adams, T. A. Geismann, and J. D. Edwards, Chem. Rev. 60, 555 (1960).
J. D. Edwards, J. Am. Chem. Soc. 47, 441 (1957).
Ch. H. Boathner, in Cottonseed and Cottonseed Products. Their Chemistry and Chemical Technology, Ed. by A. E. Bailey (Interscience, New York, 1948), p. 213.
K. Chander and T. R. Seshardi, J. Sci. Ind. Res., Sect. B 17, 279 (1958).
L. E. Castillion, C. M. Hall, and Ch. H. Boathner, J. Am. Chem. Soc. 25, 233 (1948).
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.
B. T. Ibragimov and S. A. Talipov, J. Inclusion Phenom. Mol. Recognit. Chem. 17, 325 (1994).
K. M. Beketov, B. T. Ibragimov, and S. A. Talipov, Khim. Farmats. 1, 16 (1996).
B. T. Ibragimov, K. M. Beketov, S. A. Talipov, and T. F. Aripov, J. Inclusion Phenom. Mol. Recognit. Chem. 29, 23 (1997).
K. M. Beketov, B. T. Ibragimov, and S. A. Talipov, Khim. Prir. Soedin. 30, 58 (1994).
K. M. Beketov, B. T. Ibragimov, S. A. Talipov, and T. F. Aripov, J. Inclusion Phenom. Mol. Recognit. Chem. 28, 141 (1997).
K. M. Beketov, B. T. Ibragimov, S. A. Talipov, et al., J. Inclusion Phenom. Mol. Recognit. Chem. 27, 105 (1997).
G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr. 46, 467 (1990).
G. M. Sheldrick, SHELXL93: Program for the Refinement of Crystal Structures (Univ. of Göttingen, Germany, 1993).
Siemens XP: Molecular Graphics Program, Version 5.03 (Siemens Analytical X-ray Instruments Inst., Madison, Wisconsin, 1994).
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Translated from Kristallografiya, Vol. 48, No. 4, 2003, pp. 691–698.
Original Russian Text Copyright © 2003 by Beketov, Talipov, Ibragimov, Praliev, Aripov.
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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
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DOI: https://doi.org/10.1134/1.1595193