A whole output strategy for polymorph screening: Combining crystal structure prediction, graph set analysis, and targeted crystallization experiments in the case of diflunisal

Crystal Growth and Design

Volumn 3, Issue 2, 2003, Pages 151-158

  Cross, Wendy I ^a   Blagden, Nicholas ^a   Davey, Roger J ^a   Pritchard, Robin G ^a   Neumann, Marcus A ^b   Roberts, Ronald J ^c   Rowe, Raymond C ^c  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b Accelrys Limited UK   (United Kingdom)

^c ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID; DIFLUNISAL;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CRYSTALLIZATION; EXPERIMENT; FLUORINATION; HYDROGEN BOND; PREDICTION; SCREENING;

EID: 0037262232     PISSN: 15287483     EISSN: None     Source Type: Journal    
DOI: 10.1021/cg025589n     Document Type: Article

References (33)

1. Bernstein, J. Polymorphism in Molecular Crystals; IUCR Monographs on Crystallography 14; Oxford Science Publications: OUP, Oxford, U.K., 2002.
2. Byrne, S. R.; Pfeiffer, R. R.; Stowell, J. G. Solid State Chemistry of Drugs, 2nd ed.; SSCI Inc.: West Lafayette, IN, 1999; pp 489-498.
3. Peterson, M. L.; Morissette, S. L.; McNulty, C.; Goldsweig, A.; Shaw, P. ; LeQuesne, M.; Monagle, J.; Encina, N.; Marchionna, J.; Johnson, A.; Gonzalez-Zugasti, J.; Lemmo, A. V.; Ellis, S. J.; Cima, M. J.; Almarsson, O. J. Am. Chem. Soc. 2002, 124, 10958-10959.
4. Fillipini, G.; Gavezotti, A. J. Am. Chem. Soc. 1995, 117, 12299-12302.
5. Beyer, T.; Day, G. M.; Price, S. L. J. Am. Chem. Soc. 2001, 123, 5086-5094.
6. Verwer, P.; Leusen, F. J. J. In Reviews in Computational Chemistry; Lipowitz, K. B., Boyd, D. B., Eds.; Wiley/VCH: New York, 1998; Vol. 12, Chapter 7, p 327.
7. Payne, R. S.; Roberts, R. J.; Rowe, R. C.; Docherty, R. J. Comput. Chem. 1998, 19, 1-20.
8. Blagden, N.; Cross, W. I.; Davey, R. J.; Broderick, M.; Pritchard, R. G. ; Roberts, R. J.; Rowe, R. C. Phys. Chem. Chem. Phys. 2001, 3, 3819-3825.
9. Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N.-L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1555-73.
10. Kim, Y. B.; Park, I. Y. J. Korean Pharm. Sci. 1996, 26, 55-59.
11. Cotton, M. L.; Hux, R. A. Anal. Profiles Drug Subst. 1985, 14, 491-526.
12. Martinez-Oharriz, M. C.; Martin, C.; Goni, M. M.; Rodriguez-Espinosa, C. ; Tros De Ilarduya-Apaolaza, M. C.; Sanchez, M. J. Pharm. Sci. 1994, 83, 174-177.
13. Hansen, L. Kr.; Perlovich, G. L.; Bauer-Brandl, A. Acta Crystallogr. 2001, E57, 477-479.
14. Hansen, L. Kr.; Perlovich, G. L.; Bauer-Brandl, A. Acta Crystallogr. 2001, E57, 604-606.
15. Perlovich, G. L.; Hansen, L. Kr.; Bauer-Brandl, A. J. Pharm. Sci. 2001, 91, 1036-1045.
16. Cambridge Crystallographic Data Centre: Allen, F. A.; Kennard, O. Chem. Des. Autom. News 1993, 8, 1 and 31-37.
17. Stewart, J. J. P. J. Comput.-Aided Mol. Des. 1990, 4, 1-45.
18. 3, Compass and Materials Studio; Accelrys Inc.: San Diego, CA 92121-3752.
19. Mayo, S. L.; Olafson, B. D.; Goddard, W. A. J. Phys. Chem. 1990, 94, 8897-8909.
20. Desiraju, G. R. Crystal Engineering - The Design of Organic Solids; Materials Science Monographs, Vol. 54; Elsevier: Amsterdam, The Netherlands, 1989; p 229.
21. Lommerse, J. P. M.; Motherwell, W. D. S.; Ammon, H. L.; Dunitz, J. D.; Gavezzotti, A.; Hofmann, D. W. M.; Leusen, F. J. J.; Mooij, W. T. M.; Price, S. L.; Schweizer, B.; Schmidt, M. U.; van Eijck, B. P.; Verwer, P.; Williams, D. E. Acta Crystallogr. 2000, B56, 697-714.
22. Dunitz, J. D.; Taylor, R. Chem. Eur. J. 1997, 3, 89-98.
23. Blagden, N.; Davey, R. J.; Lieberman, H. F.; Williams, L.; Payne, P.; Roberts, R. J.; Rowe, R. C.; Docherty, R. J. Chem. Soc., Faraday Trans. 1998, 94, 1035-1044.
24. Davey, R. J.; Blagden, N.; Righini, S.; Alison, H.; Quayle, M. J.; Fuller, S. Cryst. Growth Des. 2001, 1, 59-65.
25. Davey, R. J.; Allen, K.; Blagden, N.; Cross, W. I.; Lieberman, H. F.; Quayle, M. J.; Righini, S.; Seton, L.; Tiddy, G. J. T. Cryst. Eng. Commun. 2002, 4, 257-264.
26. Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467-473.
27. Neumann, M. J. Appl. Crystallogr. Submitted for publication.
28. Engel, G. E.; Wilke, S.; König, O.; Harris, K. D. M.; Leusen, F. J. J. J. Appl. Crystallogr. 1999, 32, 1169-1179.
29. Neumann, M. A.; Leusen, F. J. J.; Engel, G. E.; Wilke, S.; Conesa-Moratilla, C. Int. J. Mod. Phys. 2002, B16 (1,2), 407-414.
30. Delley, B. J. Chem. Phys. 1990, 92, 508-517.
31. Delley, B. J. Chem. Phys. 2000, 113, 7756-7764.
32. Solid State NMR spectrometry was performed in the Department of Chemistry, University of Durham, U.K. The authors acknowledge useful discussions with Prof. R. Harris and Dr. Phuong Ghi.
33. Vanderhoff, P. A.; Lalancette, R. A.; Thompson, H. W. J. Org. Chem. 1990, 55, 1696-1698.