Characterization of complicated new polymorphs of chlorothalonil by X-ray diffraction and computer crystal structure prediction

Journal of the American Chemical Society

Volumn 126, Issue 22, 2004, Pages 7071-7081

  Tremayne, Maryjane ^a   Grice, Leanne ^a   Pyatt, James C ^a   Seaton, Colin C ^a   Kariuki, Benson M ^a   Tsui, Helen H Y ^b   Price, Sarah L ^b   Cherryman, Julian C ^c  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b UNIVERSITY COLLEGE LONDON   (United Kingdom)

^c Avecia Biologics Limited   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

APPROXIMATION THEORY; COMPUTATIONAL METHODS; CRYSTAL LATTICES; X RAY DIFFRACTION;

LATTICE ENERGY; POLYMORPHS;

CRYSTAL STRUCTURE;

CHLOROTHALONIL;

ANISOTROPY; ARTICLE; ATOM; CHEMICAL STRUCTURE; COMPUTER PREDICTION; CRYSTAL STRUCTURE; ENERGY; MATHEMATICAL ANALYSIS; POWDER DIFFRACTION; X RAY DIFFRACTION;

COMPUTER SIMULATION; CRYSTALLIZATION; FUNGICIDES, INDUSTRIAL; MOLECULAR STRUCTURE; NITRILES; X-RAY DIFFRACTION;

EID: 3042771961     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0498235     Document Type: Article

References (41)

1. Bernstein, J. Polymorphism in Molecular Crystals; IUCr Monographs on Crystallography 14; Oxford University Press: New York, 2002.
2. Farm Chemicals Handbook 2002: Global Guide to Crop Protection; Meister Publishing: Willoughby, OH, 2002.
3. Britton, D. Cryst. Struct. Commun. 1981, 10, 1501.
4. Querzola, G.; Epis, G. Production Process of Chlorothalonil. Patent WO 86/06066, 1986.
5. Beyer, T.; Lewis, T.; Price, S. L. CrystEngComm 2001, 44, 178. http:// www.rsc.org/CrystEngComm.
6. (a) 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., Sect. B 2000, 56, 697.
7. (b) Motherwell, W. D. S.; Ammon, H. L.; Dunitz, J. D.; Dzyabchenko, A.; Erk, P.; Gavezzotti, A.; Hofmann, D. W. M.; Leusen, F. J. J.; Lommerse, J. P. M.; Mooij, W. T. M.; Price, S. L.; Scheraga, H.; Schweizer, B.; Schmidt, M. U.; van Eijck, B. P.; Verwer, P.; Williams, D. E. Acta Crystallogr., Sect. B 2002, 58, 348.
8. van Eijck, B. P. J. Comput. Chem. 2001, 22, 816.
9. Beyer, T.; Day, G. M.; Price, S. L. J. Am. Chem. Soc. 2001, 123, 5086.
10. Lommerse, J. P. M.; Stone, A. J.; Taylor, R.; Allen, F. H. J. Am. Chem. Soc. 1996, 118, 3108.
11. Mitchell, J. B. O.; Price, S. L.; Leslie, M.; Buttar, D.; Roberts, R. J. J. Phys. Chem. A 2001, 105, 9961.
12. Day, G. M.; Price, S. L. J. Am. Chem. Soc. 2003, 125, 16343.
13. (a) Karfunkel, H. R.; Wu, Z. J.; Burkhard, A.; Rihs, G.; Sinnreich, D.; Buerger, H. M.; Stanek, J. Acta Crystallogr., Sect. B 1996, 52, 555.
14. (b) Payne, R. S.; Roberts, R. J.; Rowe, R. C.; Docherty, R. J. Comput. Chem. 1998, 19, 1.
15. (a) Harris, K. D. M.; Tremayne, M.; Kariuki, B. M. Angew. Chem., Int. Ed. 2001, 40, 1626.
16. (b) David, W. I. F.; Shankland, K.; McCusker, L. B.; Baerlocher, C. Structure Determination from Powder Diffraction Data; IUCr Monographs on Crystallography 13; Oxford University Press: New York, 2002.
17. Sheldrick, G. M. SHELXS-86: Program for Crystal Structure Solution; University of Göttingen, Germany: Göttingen, Germany, 1986.
18. Sheldrick, G. M. SHELXL-93: Program for Crystal Structure Refinement; University of Göttingen, Germany: Göttingen, Germany, 1993.
19. Shirley, R. A. CRYSFIRE Suite of Programs for Indexing Powder Diffraction Patterns; University of Surrey: Surrey, U.K., 2000.
20. DeWolff, P. M. J. Appl. Cryst. 1968, 1, 108.
21. Seaton, C. C.; Tremayne, M. POSSUM: Programs for Direct-Space Structure Solution from Powder Diffraction Data; University of Birmingham: Birmingham, U.K., 2002.
22. Preferred orientation arises when crystallites have a tendency to align along a certain direction, resulting in a nonrandom distribution of crystallite orientations in the sample, affecting the relative intensities of given peaks. This is often most severe when the morphology is strongly anisotropic (e.g., flat plates or long needles), and the effects are often seen by comparison of the relative intensities of peaks in data collected in both disc and capillary geometries. The preferred orientation effects of platelike crystallites can be minimized by collection in capillary mode.
23. Aakeroy, C. B.; Beatty, A. M.; Rowe, D. M.; Seaton C. C.; Tremayne, M. Cryst. Growth Des. 2001, 1, 377.
24. Larson, A. C.; Von Dreele, R. B. Report No. LAUR-86-748; Los Alamos National Laboratory: Los Alamos, NM, 1987.
25. Amos, R. D.; with contributions from Alberts, I. L.; Andrews, J. S.; Colwell, S. M.; Handy, N. C.; Jayatilaka, D.; Knowles, P. J.; Kobayashi, R.; Koga, N.; Laidig, K. E.; Laming, G.; Lee, A.; Maslen, P. E.; Murray, C. W.; Rice, J. E.; Simandiras, E. D.; Stone, A. J.; Su, M. D.; Tozer, D. J. CADPAC6: The Cambridge Analytical Derivatives Package, 6.0th ed.; Cambridge University, U.K., 1995.
26. Stone, A. J.; Alderton, M. Mol. Phys. 1985, 56, 1047.
27. Williams, D. E.; Cox, S. R. Acta Crystallogr., Sect. B 1984, 40, 404.
28. Hsu, L.-Y.; Williams, D. E. Acta Crystallogr., Sect. A 1980, 36, 277.
29. Slater, J. C.; Kirkwood, J. G. Phys. Rev. 1931, 37, 682.
30. Miller, K. J. J. Am. Chem. Soc. 1990, 112, 8533.
31. Wheatley, R. J. GMUL 3s, An extension to the GMUL program (version 3) that calculates an analytical form for the overlap of distributed charge densities; University of Nottingham: Nottingham, U.K., 1997.
32. Holden, J. R.; Du, Z. Y.; Ammon, H. L. J. Comput. Chem. 1993, 14, 422.
33. Willock, D. J.; Price, S. L.; Leslie, M.; Catlow, C. R. A. J. Comput. Chem. 1995, 16, 628.
34. Day, G. M.; Price, S. L.; Leslie, M. Cryst. Growth Des. 2001, 1, 13.
35. Berkovitch-Yellin, Z. J. Am. Chem. Soc. 1985, 107, 8239.
36. Hartman, P.; Bennema, P. J. Cryst. Growth 1980, 49, 145.
37. Cerius2; Molecular Simulations Inc.: San Diego, CA, 1997.
38. Beyer, T.; Price, S. L. CrystEngComm 2000, 34, 183. http://www.rsc.org/ CrystEngComm.
39. Chickos, J. S. Heat of Sublimation Data. In NIST Chemistry WebBook, NIST Standard Reference Database; Mallard, W. G., Linstrom, P. J., Eds.; National Institute of Standards and Technology: Gaithersburg, MD, 1998; Vol. 69. http://webbook.nist.gov.
40. Gavezzotti, A. Crystal Symmetry and Molecular Recognition. In Theoretical Aspects and Computer Modeling of the Molecular Solid State; Gavezzotti, A., Ed.; John Wiley & Sons: Chichester, U.K. 1997; Vol. 1, p 97.
41. Day, G. M.; Price, S. L. Properties of Crystalline Organic Molecules; In Handbook of Elastic Properties of Solids, Liquids and Gases; Levy, M., Bass, H. E., Stern, R. R., Eds.; Academic Press: San Diego, CA, 2001; Vol. III, p 3.