Crystallization of Pseudopolymorphs of Some Gamboge Pigments. Pyridine, Dimethylformamide and Dimethylsulfoxide Solvates of Morellic Acid, Gambogic Acid and Guttiferic Acid

Supramolecular Chemistry

Volumn 13, Issue 1, 2001, Pages 11-23

  Anthony, Addlagatta ^a   Desiraju, Gautam R ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

Crystallization; Entropy; Hydrogen bond; Solvation

Indexed keywords

EID: 0035562458     PISSN: 10610278     EISSN: None     Source Type: Journal    
DOI: 10.1080/10610270108034878     Document Type: Article

References (33)

1. (a) Crystal Growth of Organic Materials, Myerson, A. S., Green, D. A. and Meenan, P. (Eds.), ACS Conference Proceedings Series, American Chemical Society, Washington, D.C., 1996;
2. (b) Desiraju, G. R. (1997). Science, 278, 404.
3. Papers that deal with the relationship between organic crystal quality and chemical (structural) factors are not common. A selected list of papers that mention methods of improving crystal quality are given here with the method proposed in each case. Some of these methods are specific to the systems studied: (a) Addadi, L., Berkovitch-Yellin, Z., Weissbuch, I., van Mil, J., Shimon, L. J. W., Lahav, M. and Leiserowitz, L. (1985). Angew. Chem. Int. Ed. Engl., 24, 466. Tailor-made impurities; (b) Etter, M. C. and Baures, P. W. (1988). J. Am. Chem. Soc., 110, 639. Triphenylphosphine oxide as a complexing agent; (c) Dance, I. G., In: The Crystal as a Supramolecular Entity (Ed. Desiraju, G. R.) Perspectives in Supramolecular Chemistry, 2, Wiley, Chichester, 1996, 137-233. The 'phenyl factor' that derives from the presence of triphenyl residues in the molecule; (d) Pedireddi, V. R., Jones, W., Chorlton, A. P. and Docherty, R. (1996). Chem. Commun., p. 997. Molecular complexation; (e) Madhavi, N. N. L., Katz, A. K., Carrell, H. L., Nangia, A. and Desiraju, G. R. (1997). Chem. Commun., p. 1953. Use of specific solvents; (f) Görbitz, C. H. and Torgersen, E. (1999). Acta Crystallogr., B55, 104. Relationship between type of hydrogen bond network and crystal quality.
4. Papers that deal with the relationship between organic crystal quality and chemical (structural) factors are not common. A selected list of papers that mention methods of improving crystal quality are given here with the method proposed in each case. Some of these methods are specific to the systems studied: (a) Addadi, L., Berkovitch-Yellin, Z., Weissbuch, I., van Mil, J., Shimon, L. J. W., Lahav, M. and Leiserowitz, L. (1985). Angew. Chem. Int. Ed. Engl., 24, 466. Tailor-made impurities; (b) Etter, M. C. and Baures, P. W. (1988). J. Am. Chem. Soc., 110, 639. Triphenylphosphine oxide as a complexing agent; (c) Dance, I. G., In: The Crystal as a Supramolecular Entity (Ed. Desiraju, G. R.) Perspectives in Supramolecular Chemistry, 2, Wiley, Chichester, 1996, 137-233. The 'phenyl factor' that derives from the presence of triphenyl residues in the molecule; (d) Pedireddi, V. R., Jones, W., Chorlton, A. P. and Docherty, R. (1996). Chem. Commun., p. 997. Molecular complexation; (e) Madhavi, N. N. L., Katz, A. K., Carrell, H. L., Nangia, A. and Desiraju, G. R. (1997). Chem. Commun., p. 1953. Use of specific solvents; (f) Görbitz, C. H. and Torgersen, E. (1999). Acta Crystallogr., B55, 104. Relationship between type of hydrogen bond network and crystal quality.
5. Papers that deal with the relationship between organic crystal quality and chemical (structural) factors are not common. A selected list of papers that mention methods of improving crystal quality are given here with the method proposed in each case. Some of these methods are specific to the systems studied: (a) Addadi, L., Berkovitch-Yellin, Z., Weissbuch, I., van Mil, J., Shimon, L. J. W., Lahav, M. and Leiserowitz, L. (1985). Angew. Chem. Int. Ed. Engl., 24, 466. Tailor-made impurities; (b) Etter, M. C. and Baures, P. W. (1988). J. Am. Chem. Soc., 110, 639. Triphenylphosphine oxide as a complexing agent; (c) Dance, I. G., In: The Crystal as a Supramolecular Entity (Ed. Desiraju, G. R.) Perspectives in Supramolecular Chemistry, 2, Wiley, Chichester, 1996, 137-233. The 'phenyl factor' that derives from the presence of triphenyl residues in the molecule; (d) Pedireddi, V. R., Jones, W., Chorlton, A. P. and Docherty, R. (1996). Chem. Commun., p. 997. Molecular complexation; (e) Madhavi, N. N. L., Katz, A. K., Carrell, H. L., Nangia, A. and Desiraju, G. R. (1997). Chem. Commun., p. 1953. Use of specific solvents; (f) Görbitz, C. H. and Torgersen, E. (1999). Acta Crystallogr., B55, 104. Relationship between type of hydrogen bond network and crystal quality.
6. Papers that deal with the relationship between organic crystal quality and chemical (structural) factors are not common. A selected list of papers that mention methods of improving crystal quality are given here with the method proposed in each case. Some of these methods are specific to the systems studied: (a) Addadi, L., Berkovitch-Yellin, Z., Weissbuch, I., van Mil, J., Shimon, L. J. W., Lahav, M. and Leiserowitz, L. (1985). Angew. Chem. Int. Ed. Engl., 24, 466. Tailor-made impurities; (b) Etter, M. C. and Baures, P. W. (1988). J. Am. Chem. Soc., 110, 639. Triphenylphosphine oxide as a complexing agent; (c) Dance, I. G., In: The Crystal as a Supramolecular Entity (Ed. Desiraju, G. R.) Perspectives in Supramolecular Chemistry, 2, Wiley, Chichester, 1996, 137-233. The 'phenyl factor' that derives from the presence of triphenyl residues in the molecule; (d) Pedireddi, V. R., Jones, W., Chorlton, A. P. and Docherty, R. (1996). Chem. Commun., p. 997. Molecular complexation; (e) Madhavi, N. N. L., Katz, A. K., Carrell, H. L., Nangia, A. and Desiraju, G. R. (1997). Chem. Commun., p. 1953. Use of specific solvents; (f) Görbitz, C. H. and Torgersen, E. (1999). Acta Crystallogr., B55, 104. Relationship between type of hydrogen bond network and crystal quality.
7. Papers that deal with the relationship between organic crystal quality and chemical (structural) factors are not common. A selected list of papers that mention methods of improving crystal quality are given here with the method proposed in each case. Some of these methods are specific to the systems studied: (a) Addadi, L., Berkovitch-Yellin, Z., Weissbuch, I., van Mil, J., Shimon, L. J. W., Lahav, M. and Leiserowitz, L. (1985). Angew. Chem. Int. Ed. Engl., 24, 466. Tailor-made impurities; (b) Etter, M. C. and Baures, P. W. (1988). J. Am. Chem. Soc., 110, 639. Triphenylphosphine oxide as a complexing agent; (c) Dance, I. G., In: The Crystal as a Supramolecular Entity (Ed. Desiraju, G. R.) Perspectives in Supramolecular Chemistry, 2, Wiley, Chichester, 1996, 137-233. The 'phenyl factor' that derives from the presence of triphenyl residues in the molecule; (d) Pedireddi, V. R., Jones, W., Chorlton, A. P. and Docherty, R. (1996). Chem. Commun., p. 997. Molecular complexation; (e) Madhavi, N. N. L., Katz, A. K., Carrell, H. L., Nangia, A. and Desiraju, G. R. (1997). Chem. Commun., p. 1953. Use of specific solvents; (f) Görbitz, C. H. and Torgersen, E. (1999). Acta Crystallogr., B55, 104. Relationship between type of hydrogen bond network and crystal quality.
8. Papers that deal with the relationship between organic crystal quality and chemical (structural) factors are not common. A selected list of papers that mention methods of improving crystal quality are given here with the method proposed in each case. Some of these methods are specific to the systems studied: (a) Addadi, L., Berkovitch-Yellin, Z., Weissbuch, I., van Mil, J., Shimon, L. J. W., Lahav, M. and Leiserowitz, L. (1985). Angew. Chem. Int. Ed. Engl., 24, 466. Tailor-made impurities; (b) Etter, M. C. and Baures, P. W. (1988). J. Am. Chem. Soc., 110, 639. Triphenylphosphine oxide as a complexing agent; (c) Dance, I. G., In: The Crystal as a Supramolecular Entity (Ed. Desiraju, G. R.) Perspectives in Supramolecular Chemistry, 2, Wiley, Chichester, 1996, 137-233. The 'phenyl factor' that derives from the presence of triphenyl residues in the molecule; (d) Pedireddi, V. R., Jones, W., Chorlton, A. P. and Docherty, R. (1996). Chem. Commun., p. 997. Molecular complexation; (e) Madhavi, N. N. L., Katz, A. K., Carrell, H. L., Nangia, A. and Desiraju, G. R. (1997). Chem. Commun., p. 1953. Use of specific solvents; (f) Görbitz, C. H. and Torgersen, E. (1999). Acta Crystallogr., B55, 104. Relationship between type of hydrogen bond network and crystal quality.
9. Venkataraman, K., Pigments of Garcinia species, Indian National Science Academy, New Delhi, 1973.
10. Kartha, G., Ramachandran, G. N., Bhat, H. B., Nair, P. M., Raghavan, V. K. V. and Venkataraman, K. (1963). Tetrahedron Lett., 7, 459.
11. Rao, K. V. N. and Rao, P. L. N. (1961). Experientia, 17, 213.
12. Gupta, V. S., Rao, P. L. N., Vaidya, S. N. and Ramaseshan, S. (1962). Chem. and Ind., p. 1469.
13. Rao, D. R. (1955). A.I.I. Sci. Thesis, Indian Institute of Science, Bangalore.
14. Santhanam, K. (1967). Ph.D. Thesis, Indian Institute of Science, Bangalore.
15. By 'pseudopolymorphism', we refer to the phenomenon wherein a compound is obtained in crystalline forms that differ in the nature or stoichiometry of included solvent molecules. See (a) Threlfall, T. L. (1995). Analyst, 120, 2435 and (b) Bernstein, J., In: Organic Solid State Chemistry (Ed. Desiraju, G. R.), Studies in Organic Chemistry, 32, Elsevier, Amsterdam, 471-518.
16. By 'pseudopolymorphism', we refer to the phenomenon wherein a compound is obtained in crystalline forms that differ in the nature or stoichiometry of included solvent molecules. See (a) Threlfall, T. L. (1995). Analyst, 120, 2435 and (b) Bernstein, J., In: Organic Solid State Chemistry (Ed. Desiraju, G. R.), Studies in Organic Chemistry, 32, Elsevier, Amsterdam, 471-518.
17. Sheldrick, G. M., SHELX-97, Program for crystal structure solution and refinement, University of Göttingen, Germany, 1997.
18. These and other hydrogen bond geometries are neutron-normalized.
19. Takasuka, M., Nakai, H. and Shiro, M. (1982). J. Chem. Soc., Perkin Trans., 2, 1061.
20. (a) Weber, E. J. (1989). Mol. Graphics, 7, 12;
21. (b) Desiraju, G. R. (1991). Acc. Chem. Res., 24, 270.
22. Chaney, J. D., Goss, C. R., Folting, K., Santarsiero, B. D. and Hollingsworth, M. D. (1996). J. Am. Chem. Soc., 118, 9432.
23. Desiraju, G. R. and Steiner, T., The Weak Hydrogen Bond in Structural Chemistry and Biology, Oxford University Press, Oxford, 1999.
24. (a) Desiraju, G. R. (1996). Acc. Chem. Res., 29, 441;
25. (b) Steiner, T. (1996). Oysf. Rev., 6, 1.
26. (a) Csöregh, I., Gallardo, O., Weber, E., Pollex, R. and Dörpinghaus, N. (1995). J. Incl. Phen. Mol. Recog. Chem., 20, 253;
27. (b) However, for the crystal structure of a very unusual dmso solvate see, Kaduk, J. A., Cahill, P. J. and Venkateshwaran, L. N. (1999). J. Appl. Cryst., 32, 15.
28. Nangia, A. and Desiraju, G. R. (1999). Chem. Commun., 605. This study shows that dmso is included about five times more often than might have been expected on the basis of its usage as a recrystallizing solvent, and that in most of the cases wherein the solute contains O/N-H groups, the solvent forms C-H⋯O hydrogen bonds in addition to stronger O/N-H⋯O bonds.
29. Leiserowitz, L. (1976). Acta Crystallogr., B32, 775.
30. (a) Payne, R. S., Roberts, R. J., Rowe, R. C. and Docherty, R. (1998). J. Comput. Chem., 19, 1;
31. (b) Mooij, W. T. M., van Eijck, B. P., Price, S. L., Verwer, P. and Kroon, J. (1998). J. Comput. Chem., 19, 459.
32. Kuduva, S. S., Craig, D. C., Nangia, A. and Desiraju, G. R. (1999). J. Am. Chem. Soc., 121, 1936.
33. Luger, P. (1998). Angew. Chem. Int. Ed. Engl., 37, 3353.