Do polymorphic compounds make good cocrystallizing agents? A structural case study that demonstrates the importance of synthon flexibility

Crystal Growth and Design

Volumn 3, Issue 2, 2003, Pages 159-165

  Aakeröy, Christer B ^a   Beatty, Alicia M ^b   Helfrich, Brian A ^a   Nieuwenhuyzen, Mark ^c  

^a KANSAS STATE UNIVERSITY   (United States)

^b UNIVERSITY OF NOTRE DAME   (United States)

^c QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 3 NITROPYRIDINE; 4 CHLOROBENZAMIDE; ALIPHATIC COMPOUND; AROMATIC COMPOUND; BENZAMIDE DERIVATIVE; CHEMICAL COMPOUND; ISONICOTINAMIDE; MALEIC HYDRAZIDE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CRYSTALLIZATION; HYDROGEN BOND; MOLECULAR DYNAMICS; MOLECULAR INTERACTION;

EID: 0037266029     PISSN: 15287483     EISSN: None     Source Type: Journal    
DOI: 10.1021/cg025593z     Document Type: Article

References (27)

1. Solid State Chemistry of Drugs; Byrn, S. E., Pfeiffer, R. R., Stowell, J. G., Eds.; SSCI Inc.: West Lafayette, 1999.
2. Aakeröy, C. B. Acta Crystallogr. Sect. B 1997.
3. A few examples of successful cocrystallization experiments. (b) Sarma, J. A. R. P.; Desiraju, G. R. J. Chem. Soc., Perkin Trans. 2 1985, 1905. (c) Huang, C.; Leiserowitz, L.; Schmidt, G. M. J. Chem. Soc., Perkin Trans. 2 1973, 503. (d) Tamura, C.; Sakurai, N.; Sato, S. Bull. Chem. Soc. Jpn. 1971, 44, 1473. (e) Pan, F.; Wong, M. S.; Gramlich, V.; Bosshard, C.; Gunter, P. Chem. Commun. 1996, 2. (f) LeFur, Y.; Bagieu-Beucher, M.; Masse, R.; Nicoud, J. F.; Levy, J. P. Chem. Mater. 1996, 8, 8. (g) Zerkowski, J. A.; MacDonald, J. C.; Whitesides, G. M. Chem. Mater. 1997, 9, 9. (h) Liao, R.-F.; Lauher, J. W.; Fowler, F. W. Tetrahedron 1996, 52, 3153. (i) Shan, N.; Bond, A. D.; Jones, W. Cryst. Eng. 2002, 5, 9. (j) Pedireddi, V. R.; Jones, W.; Chorlton, A. P.; Docherty, R. Chem. Commun. 1996, 997. (k) Vishweshwar, P.; Nangia, A.; Lynch, V. M. J. Org. Chem. 2002, 67, 556.
4. A few examples of successful cocrystallization experiments. (b) Sarma, J. A. R. P.; Desiraju, G. R. J. Chem. Soc., Perkin Trans. 2 1985, 1905. (c) Huang, C.; Leiserowitz, L.; Schmidt, G. M. J. Chem. Soc., Perkin Trans. 2 1973, 503. (d) Tamura, C.; Sakurai, N.; Sato, S. Bull. Chem. Soc. Jpn. 1971, 44, 1473. (e) Pan, F.; Wong, M. S.; Gramlich, V.; Bosshard, C.; Gunter, P. Chem. Commun. 1996, 2. (f) LeFur, Y.; Bagieu-Beucher, M.; Masse, R.; Nicoud, J. F.; Levy, J. P. Chem. Mater. 1996, 8, 8. (g) Zerkowski, J. A.; MacDonald, J. C.; Whitesides, G. M. Chem. Mater. 1997, 9, 9. (h) Liao, R.-F.; Lauher, J. W.; Fowler, F. W. Tetrahedron 1996, 52, 3153. (i) Shan, N.; Bond, A. D.; Jones, W. Cryst. Eng. 2002, 5, 9. (j) Pedireddi, V. R.; Jones, W.; Chorlton, A. P.; Docherty, R. Chem. Commun. 1996, 997. (k) Vishweshwar, P.; Nangia, A.; Lynch, V. M. J. Org. Chem. 2002, 67, 556.
5. A few examples of successful cocrystallization experiments. (b) Sarma, J. A. R. P.; Desiraju, G. R. J. Chem. Soc., Perkin Trans. 2 1985, 1905. (c) Huang, C.; Leiserowitz, L.; Schmidt, G. M. J. Chem. Soc., Perkin Trans. 2 1973, 503. (d) Tamura, C.; Sakurai, N.; Sato, S. Bull. Chem. Soc. Jpn. 1971, 44, 1473. (e) Pan, F.; Wong, M. S.; Gramlich, V.; Bosshard, C.; Gunter, P. Chem. Commun. 1996, 2. (f) LeFur, Y.; Bagieu-Beucher, M.; Masse, R.; Nicoud, J. F.; Levy, J. P. Chem. Mater. 1996, 8, 8. (g) Zerkowski, J. A.; MacDonald, J. C.; Whitesides, G. M. Chem. Mater. 1997, 9, 9. (h) Liao, R.-F.; Lauher, J. W.; Fowler, F. W. Tetrahedron 1996, 52, 3153. (i) Shan, N.; Bond, A. D.; Jones, W. Cryst. Eng. 2002, 5, 9. (j) Pedireddi, V. R.; Jones, W.; Chorlton, A. P.; Docherty, R. Chem. Commun. 1996, 997. (k) Vishweshwar, P.; Nangia, A.; Lynch, V. M. J. Org. Chem. 2002, 67, 556.
6. A few examples of successful cocrystallization experiments. (b) Sarma, J. A. R. P.; Desiraju, G. R. J. Chem. Soc., Perkin Trans. 2 1985, 1905. (c) Huang, C.; Leiserowitz, L.; Schmidt, G. M. J. Chem. Soc., Perkin Trans. 2 1973, 503. (d) Tamura, C.; Sakurai, N.; Sato, S. Bull. Chem. Soc. Jpn. 1971, 44, 1473. (e) Pan, F.; Wong, M. S.; Gramlich, V.; Bosshard, C.; Gunter, P. Chem. Commun. 1996, 2. (f) LeFur, Y.; Bagieu-Beucher, M.; Masse, R.; Nicoud, J. F.; Levy, J. P. Chem. Mater. 1996, 8, 8. (g) Zerkowski, J. A.; MacDonald, J. C.; Whitesides, G. M. Chem. Mater. 1997, 9, 9. (h) Liao, R.-F.; Lauher, J. W.; Fowler, F. W. Tetrahedron 1996, 52, 3153. (i) Shan, N.; Bond, A. D.; Jones, W. Cryst. Eng. 2002, 5, 9. (j) Pedireddi, V. R.; Jones, W.; Chorlton, A. P.; Docherty, R. Chem. Commun. 1996, 997. (k) Vishweshwar, P.; Nangia, A.; Lynch, V. M. J. Org. Chem. 2002, 67, 556.
7. A few examples of successful cocrystallization experiments. (b) Sarma, J. A. R. P.; Desiraju, G. R. J. Chem. Soc., Perkin Trans. 2 1985, 1905. (c) Huang, C.; Leiserowitz, L.; Schmidt, G. M. J. Chem. Soc., Perkin Trans. 2 1973, 503. (d) Tamura, C.; Sakurai, N.; Sato, S. Bull. Chem. Soc. Jpn. 1971, 44, 1473. (e) Pan, F.; Wong, M. S.; Gramlich, V.; Bosshard, C.; Gunter, P. Chem. Commun. 1996, 2. (f) LeFur, Y.; Bagieu-Beucher, M.; Masse, R.; Nicoud, J. F.; Levy, J. P. Chem. Mater. 1996, 8, 8. (g) Zerkowski, J. A.; MacDonald, J. C.; Whitesides, G. M. Chem. Mater. 1997, 9, 9. (h) Liao, R.-F.; Lauher, J. W.; Fowler, F. W. Tetrahedron 1996, 52, 3153. (i) Shan, N.; Bond, A. D.; Jones, W. Cryst. Eng. 2002, 5, 9. (j) Pedireddi, V. R.; Jones, W.; Chorlton, A. P.; Docherty, R. Chem. Commun. 1996, 997. (k) Vishweshwar, P.; Nangia, A.; Lynch, V. M. J. Org. Chem. 2002, 67, 556.
8. A few examples of successful cocrystallization experiments. (b) Sarma, J. A. R. P.; Desiraju, G. R. J. Chem. Soc., Perkin Trans. 2 1985, 1905. (c) Huang, C.; Leiserowitz, L.; Schmidt, G. M. J. Chem. Soc., Perkin Trans. 2 1973, 503. (d) Tamura, C.; Sakurai, N.; Sato, S. Bull. Chem. Soc. Jpn. 1971, 44, 1473. (e) Pan, F.; Wong, M. S.; Gramlich, V.; Bosshard, C.; Gunter, P. Chem. Commun. 1996, 2. (f) LeFur, Y.; Bagieu-Beucher, M.; Masse, R.; Nicoud, J. F.; Levy, J. P. Chem. Mater. 1996, 8, 8. (g) Zerkowski, J. A.; MacDonald, J. C.; Whitesides, G. M. Chem. Mater. 1997, 9, 9. (h) Liao, R.-F.; Lauher, J. W.; Fowler, F. W. Tetrahedron 1996, 52, 3153. (i) Shan, N.; Bond, A. D.; Jones, W. Cryst. Eng. 2002, 5, 9. (j) Pedireddi, V. R.; Jones, W.; Chorlton, A. P.; Docherty, R. Chem. Commun. 1996, 997. (k) Vishweshwar, P.; Nangia, A.; Lynch, V. M. J. Org. Chem. 2002, 67, 556.
9. A few examples of successful cocrystallization experiments. (b) Sarma, J. A. R. P.; Desiraju, G. R. J. Chem. Soc., Perkin Trans. 2 1985, 1905. (c) Huang, C.; Leiserowitz, L.; Schmidt, G. M. J. Chem. Soc., Perkin Trans. 2 1973, 503. (d) Tamura, C.; Sakurai, N.; Sato, S. Bull. Chem. Soc. Jpn. 1971, 44, 1473. (e) Pan, F.; Wong, M. S.; Gramlich, V.; Bosshard, C.; Gunter, P. Chem. Commun. 1996, 2. (f) LeFur, Y.; Bagieu-Beucher, M.; Masse, R.; Nicoud, J. F.; Levy, J. P. Chem. Mater. 1996, 8, 8. (g) Zerkowski, J. A.; MacDonald, J. C.; Whitesides, G. M. Chem. Mater. 1997, 9, 9. (h) Liao, R.-F.; Lauher, J. W.; Fowler, F. W. Tetrahedron 1996, 52, 3153. (i) Shan, N.; Bond, A. D.; Jones, W. Cryst. Eng. 2002, 5, 9. (j) Pedireddi, V. R.; Jones, W.; Chorlton, A. P.; Docherty, R. Chem. Commun. 1996, 997. (k) Vishweshwar, P.; Nangia, A.; Lynch, V. M. J. Org. Chem. 2002, 67, 556.
10. A few examples of successful cocrystallization experiments. (b) Sarma, J. A. R. P.; Desiraju, G. R. J. Chem. Soc., Perkin Trans. 2 1985, 1905. (c) Huang, C.; Leiserowitz, L.; Schmidt, G. M. J. Chem. Soc., Perkin Trans. 2 1973, 503. (d) Tamura, C.; Sakurai, N.; Sato, S. Bull. Chem. Soc. Jpn. 1971, 44, 1473. (e) Pan, F.; Wong, M. S.; Gramlich, V.; Bosshard, C.; Gunter, P. Chem. Commun. 1996, 2. (f) LeFur, Y.; Bagieu-Beucher, M.; Masse, R.; Nicoud, J. F.; Levy, J. P. Chem. Mater. 1996, 8, 8. (g) Zerkowski, J. A.; MacDonald, J. C.; Whitesides, G. M. Chem. Mater. 1997, 9, 9. (h) Liao, R.-F.; Lauher, J. W.; Fowler, F. W. Tetrahedron 1996, 52, 3153. (i) Shan, N.; Bond, A. D.; Jones, W. Cryst. Eng. 2002, 5, 9. (j) Pedireddi, V. R.; Jones, W.; Chorlton, A. P.; Docherty, R. Chem. Commun. 1996, 997. (k) Vishweshwar, P.; Nangia, A.; Lynch, V. M. J. Org. Chem. 2002, 67, 556.
11. A few examples of successful cocrystallization experiments. (b) Sarma, J. A. R. P.; Desiraju, G. R. J. Chem. Soc., Perkin Trans. 2 1985, 1905. (c) Huang, C.; Leiserowitz, L.; Schmidt, G. M. J. Chem. Soc., Perkin Trans. 2 1973, 503. (d) Tamura, C.; Sakurai, N.; Sato, S. Bull. Chem. Soc. Jpn. 1971, 44, 1473. (e) Pan, F.; Wong, M. S.; Gramlich, V.; Bosshard, C.; Gunter, P. Chem. Commun. 1996, 2. (f) LeFur, Y.; Bagieu-Beucher, M.; Masse, R.; Nicoud, J. F.; Levy, J. P. Chem. Mater. 1996, 8, 8. (g) Zerkowski, J. A.; MacDonald, J. C.; Whitesides, G. M. Chem. Mater. 1997, 9, 9. (h) Liao, R.-F.; Lauher, J. W.; Fowler, F. W. Tetrahedron 1996, 52, 3153. (i) Shan, N.; Bond, A. D.; Jones, W. Cryst. Eng. 2002, 5, 9. (j) Pedireddi, V. R.; Jones, W.; Chorlton, A. P.; Docherty, R. Chem. Commun. 1996, 997. (k) Vishweshwar, P.; Nangia, A.; Lynch, V. M. J. Org. Chem. 2002, 67, 556.
12. A few examples of successful cocrystallization experiments. (b) Sarma, J. A. R. P.; Desiraju, G. R. J. Chem. Soc., Perkin Trans. 2 1985, 1905. (c) Huang, C.; Leiserowitz, L.; Schmidt, G. M. J. Chem. Soc., Perkin Trans. 2 1973, 503. (d) Tamura, C.; Sakurai, N.; Sato, S. Bull. Chem. Soc. Jpn. 1971, 44, 1473. (e) Pan, F.; Wong, M. S.; Gramlich, V.; Bosshard, C.; Gunter, P. Chem. Commun. 1996, 2. (f) LeFur, Y.; Bagieu-Beucher, M.; Masse, R.; Nicoud, J. F.; Levy, J. P. Chem. Mater. 1996, 8, 8. (g) Zerkowski, J. A.; MacDonald, J. C.; Whitesides, G. M. Chem. Mater. 1997, 9, 9. (h) Liao, R.-F.; Lauher, J. W.; Fowler, F. W. Tetrahedron 1996, 52, 3153. (i) Shan, N.; Bond, A. D.; Jones, W. Cryst. Eng. 2002, 5, 9. (j) Pedireddi, V. R.; Jones, W.; Chorlton, A. P.; Docherty, R. Chem. Commun. 1996, 997. (k) Vishweshwar, P.; Nangia, A.; Lynch, V. M. J. Org. Chem. 2002, 67, 556.
13. Aakeröy, C. B.; Beatty, A. B.; Helfrich, B. H. J. Am. Chem. Soc. 2002, 124, 14425-14432.
14. There are, of course, other aspects that need to be considered (e.g., solubility differences between drug and CA (if the cocrystals are to be prepared via solution-based methods-))before embarking upon a series of cocrystallizations.
15. Bernstein, J. Polymorphism in Molecular Crystals; Oxford University Press: New York, 2002.
16. After the initial submission of this manuscript, one reviewer pointed out that 3 (a compound that was not originally part of the study) is also known to be polymorphic (with different hydrogen bond motifs); yet, there are no reported cocrystals or solvates. Because we suggest in this paper that a polymorphic compound displaying synthon flexibility should be a good CA, it seemed that 3 would provide a perfect, independently selected, "test case" for our hypothesis, and it was subsequently included in our study.
17. Forms I and III of 3: (a) Taniguch, T.; Nakata, K.; Takaki, Y.; Sakurai, K. Acta Crystallogr. Sect. B 1978, 34, 2574. Form II: (b) Hayashi, T.; Nakata, K.; Takaki, Y.; Sakurai, K. Bull. Chem. Soc. Jpn. 1980, 53, 801.
18. Forms I and III of 3: (a) Taniguch, T.; Nakata, K.; Takaki, Y.; Sakurai, K. Acta Crystallogr. Sect. B 1978, 34, 2574. Form II: (b) Hayashi, T.; Nakata, K.; Takaki, Y.; Sakurai, K. Bull. Chem. Soc. Jpn. 1980, 53, 801.
19. Destro, R.; Pilati, T.; Simonetta, M. Acta Crystallogr. Sect. B 1975, 31, 2883.
20. Aakeröy, C. B.; Beatty, A. M.; Nieuwenhuyzen, M.; Zou, M. J. Mater. Chem. 1998, 8, 1385.
21. Cradwick, P. D. Nature 1975, 258, 774.
22. Katrusiak, A. Acta Crystallogr. Sect. C 1993, 49, 36.
23. Katrusiak, A. Acta Crystallogr. Sect. B 2001, 57, 697.
24. The three cocrystals 11-13 can also be obtained by manually grinding equimolar mixtures of the relevant components together. The experimental XRD patterns for all solids obtained from grinding match well with the simulated X-ray powder patterns based upon experimental single-crystal data obtained from the corresponding cocrystals prepared from solution.
25. Kortüm, G., Vogel, W., Andrussov, K. Dissociation Constants of Organic Acids in Aqueous Solution; Butterworth: London, 1961.
26. Aakeröy, C. B.; Beatty, A. M.; Helfrich, B. A. Angew. Chem., Int. Ed. 2001, 40, 3240.
27. Etter, M. C.; MacDonald, J. C.; Bernstein, J. Acta Crystallogr. Sect. B 1990, 46, 256.