Abundant polymorphism in a system with multiple hydrogen-bonding opportunities: Oxalyl dihydrazide

Journal of the American Chemical Society

Volumn 128, Issue 26, 2006, Pages 8441-8452

  Ahn, Shinbyoung ^a   Guo, Fang ^b   Kariuki, Benson M ^a   Harris, Kenneth D M ^b  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONS; CRYSTAL STRUCTURE; CRYSTALLIZATION; HYDROGEN BONDS; MOLECULAR STRUCTURE;

GEOMETRIC PERMUTATIONS; OXALYL DIHYDRAZIDE; POLYMORPHISM; TRANS-TRANS-TRANS CONFORMATION;

HYDROGEN INORGANIC COMPOUNDS;

CARBON; HYDRAZIDE DERIVATIVE; HYDROGEN; NITROGEN; OXALIC ACID DERIVATIVE; OXALYL DIHYDRAZIDE; OXYGEN; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; CRYSTALLIZATION; HYDROGEN BOND; MOLECULE; SOLID STATE;

EID: 33745685955     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0573155     Document Type: Article

References (35)

1. Dunitz, J. D. Pure Appl. Chem. 1991, 63, 177.
2. Bernstein, J. J. Phys. D: Appl. Phys. 1993, 26, B66.
3. Dunitz, J. D.; Bernstein, J. Acc. Chem. Res. 1995, 28, 193.
4. Dunitz, J. D. Acta Crystallogr., Sect. B 1995, 51, 619.
5. Bernstein, J.; Davey, R. J.; Henck, J.-O. Angew. Chem., Int. Ed. 1999, 38, 3441.
6. Bernstein, J. Polymorphism in Molecular Crystals; Oxford University Press: Oxford, 2002.
7. Davey, R. J. Chem. Commun. 2003, 1463.
8. Bernstein, J. Chem. Commun. 2005, 5007.
9. Throughout this paper, we adhere strictly to the requirement that polymorphic forms have identical chemical composition: in the case of molecular crystals, they must contain the same type(s) of molecule(s) with the same stoichiometry. A given type of molecule may exist in different crystalline phases, such as (i) "pure" crystals containing only the given type of molecule or (ii) cocrystals containing the given type of molecule and one or more other types of molecule (which encompasses also solvate phases in which the "other molecule" is the solvent used in crystal growth). Crystalline phases within a given category, provided they have the same chemical composition, may be classified as polymorphic forms. Crystalline phases in different categories cannot be classified as polymorphic forms. We note that the present paper considers only crystalline phases of the type covered by category (i).
10. 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.
11. Price, C. P.; Grzesiak, A. L.; Matzger, A. J. J. Am. Chem. Soc. 2005, 127, 5512.
12. Price, S. L. In Computer Modelling in Inorganic Crystallography; Catlow, C. R. A., Ed.; Academic Press: San Diego, 1997; pp 269-293.
13. Gavezzotti, A. Crystallogr. Rev. 1998, 7, 5.
14. Verwer, P.; Leusen, F. J. J. Rev. Comput. Chem. 1998, 12, 327.
15. Dunitz, J. D. Chem. Commun. 2003, 545.
16. Price, S. L. Adv. Drug Delivery Rev. 2004, 56, 301.
17. Yu, L.; Stephenson, G. A.; Mitchell, C. A.; Bunnell, C. A.; Snorek, S. V.; Bowyer, J. J.; Borchardt, T. B.; Stowell, J. G.; Byrn, S. R. J. Am. Chem. Soc. 2000, 122, 585.
18. Mitchell, C. A.; Yu, L.; Ward, M. D. J. Am. Chem. Soc. 2001, 123, 10830.
19. Chen, S.; Guzei, I.; Yu, L. J. Am. Chem. Soc. 2005, 127, 9881.
20. Quaeyhaegens, F.; Desseyn, H. O.; Bracke, B.; Lenstra, A. T. H. J. Mol. Struct. 1990, 238, 139.
21. From a survey of the Cambridge Structural Database (Version 5.26, update August 2005).
22. Harris, K. D. M.; Stainton, N. M.; Callan, A. M.; Howie, R. A. J. Mater. Chem. 1993, 3, 947.
23. Sheldrick, G. M. SHELX97, Programs for Crystal Structure Analysis (Release 97-2); Institut für Anorganische Chemie der Universität: Göttingen, Germany, 1998.
24. Harris, K. D. M.; Patterson, I. L. J. J. Chem. Soc., Perkin Trans. 2 1994, 1201.
25. Etter, M. C. Acc. Chem. Res. 1990, 23, 120.
26. Etter, M. C.; MacDonald, J. C.; Bernstein, J. Acta Crystallogr., Sect. B 1990, 46, 256.
27. Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1555.
28. Tripathi, G. N. R.; Katon, J. E. J. Mol. Struct. 1979, 54, 19.
29. Burger, A.; Ramberger, R. Mikrochim. Acta 1979, 2, 259.
30. Burger, A.; Ramberger, R. Mikrochim. Acta 1979, 2, 273.
31. Giron, D. Thermochim. Acta 1995, 248, 1.
32. Yu, L.; Huang, J.; Jones, K. J. J. Phys. Chem. B 2005, 109, 19915.
33. Guo, F.; Ahn, S.; Kariuki, B. M.; Harris, K. D. M. Manuscript to be submitted.
34. -1).
35. These experiments have so far been carried out for the α and γ polymorphs, as these polymorphic forms are generally easier to prepare as monophasic samples in large quantities.