Polymorphic crystals formed by an achiral diol under ambient conditions

Crystal Growth and Design

Volumn 12, Issue 11, 2012, Pages 5746-5756

  Gao, Jiabin ^a   Bhadbhade, Mohan M ^a   Bishop, Roger ^a  

^a UNIVERSITY OF NEW SOUTH WALES   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ACHIRAL MOLECULE; AMBIENT CONDITIONS; CLATHRATE STRUCTURE; CRYSTAL FORMS; CRYSTALLIZATION BEHAVIOR; POLYMORPHIC CRYSTALS; PYRIDYL; ROOM TEMPERATURE; SOLVENT FREE; STRUCTURAL FEATURE; X-RAY STRUCTURE;

BENZENE; CRYSTALLIZATION;

HYDRATES;

EID: 84868687169     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg301259f     Document Type: Article

References (78)

1. Resolutions and Polymorphs. Part 8. Gao, J.; Bhadbhade, M. M.; Bishop, R. Different crystal forms of a rich hydrogen bond acceptor compound resulting from alternative CH⋯O and orthogonal C= O⋯C=O molecular interaction patterns. CrystEngComm 2012, 14, 138-146.
2. Vega, A.; Donoso-Tauda, O.; Ibañez, A.; Escobar, C. A. Acta Crystallogr., Sect. C 2008, 64, o199.
3. Chan, I. Y. H.; Nguyen, V. T.; Bishop, R.; Craig, D. C.; Scudder, M. L. Cryst. Growth Des. 2010, 10, 4582-4589.
4. (a) Chan, I. Y. H.; Bhadbhade, M. M.; Bishop, R. CrystEngComm 2011, 13, 3162-3169.
5. (b) Chan, I. Y. H. Ph.D. Thesis, The University of New South Wales, Australia, 2010.
6. Kitaigorodsky, A. I. Molecular Crystals and Molecules, Academic Press, New York, 1973.
7. (a) Powell, H. M. J. Chem. Soc. 1948, 61-73.
8. (b) Powell, H. M.; Wetters, B. D. P. Chem. Ind. (London) 1955, 256-257.
9. (c) Desiraju, G. R. in Comprehensive Supramolecular Chemistry; MacNicol, D. D.; Toda, F.; Bishop, R., Eds.; Pergamon Press: Oxford, 1996; Vol. 6, Chapter 1, pp 1-22.
10. (d) Rahman, A. N. M. M.; Bishop, R.; Craig, D. C.; Scudder, M. L. Chem. Commun. 1999, 2389-2390.
11. (e) Dunitz, J. D.; Filippini, G.; Gavezzotti, A. Tetrahedron 2000, 56, 6595-6601.
12. (f) Bishop., R. New Aspects of aromatic π ⋯π and CH⋯π interactions in crystal engineering. In The Importance of Pi-Interactions in Crystal Engineering: Frontiers in Crystal Engineering; Tiekink, E. R. T., Zukerman-Schpector, J., Eds.; Wiley: Chichester, 2012; Chapter 2, pp 41-77.
13. (a) MacNicol, D. D.; Downing, G. R. Symmetry in the evolution of host design. In Comprehensive Supramolecular Chemistry, Vol. 6 Solidstate Supramolecular Chemistry: Crystal Engineering; MacNicol, D. D.; Toda, F.; Bishop, R., Eds.; Pergamon Press: Oxford, 1996; Chapter 14, pp 421-464.
14. (b) Goldberg, I. in Inclusion Compounds; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Eds.; Oxford University Press: Oxford, 1991; Vol. 4, Chapter 10, pp 406-447.
15. (c) Weber, E. Shape and symmetry in the design of new hosts. In Comprehensive Supramolecular Chemistry, Vol. 6 Solid-state Supramolecular Chemistry: Crystal Engineering; MacNicol, D. D., Toda, F., Bishop, R., Eds.; Pergamon Press: Oxford, 1996; Chapter 17, pp 535-592.
16. (d) Bishop, R. Synlett 1999, 1351-1358.
17. (e) Pigge, F. C. CrystEngComm 2011, 13, 1733-1748.
18. (f) Bishop, R. Aust. J. Chem. 2012, 65, 1361-1370.
19. (a) Inclusion Compounds; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Eds.; Academic Press: London, 1984; Vols. 1-3.
20. (b) Comprehensive Supramolecular Chemistry, MacNicol, D. D.; Toda, F.; Bishop, R., Eds.; Pergamon Press: Oxford, 1996, Vol. 6.
21. (c) Herbstein, F. H. Crystalline Molecular Complexes and Compounds: Structures and Principles, Oxford University Press: Oxford, 2005.
22. (d) Bishop, R. Synthetic clathrate systems. In Supramolecular Chemistry: From Molecules to Nanomaterials; Gale, P. A., Steed, J. W., Eds.; Wiley, Chichester, 2012; pp 3033-3056.
23. (a) Bishop, R.; Dance, I. J. Chem. Soc., Chem. Commun. 1979, 992-993.
24. (b) Bishop, R.; Choudhury, S.; Dance, I. J. Chem. Soc., Perkin Trans 2 1982, 1159-1168.
25. (c) Bishop, R.; Dance, I. G.; Hawkins, S. C. J. Chem. Soc., Chem. Commun. 1983, 889-891.
26. (d) Bishop, R.; Dance, I. G.; In Inclusion Compounds, Atwood, J. L.; Davies, J. E. D.; MacNicol, D. D., Eds.; Oxford University Press: Oxford, 1991; Vol. 4, Chapter 1, pp 1-26.
27. (e) Hawkins, S. C.; Bishop, R.; Dance, I. G.; Lipari, T.; Craig, D. C.; Scudder, M. L. J. Chem. Soc., Perkin Trans. 2 1993, 1729-1735.
28. (f) Kim, S.; Bishop, R.; Craig, D. C.; Dance, I. G.; Scudder, M. L. J. Org. Chem. 2002, 67, 3221-3230.
29. (a) Hawkins, S. C.; Scudder, M. L.; Craig, D. C.; Rae, A. D.; Abdul Raof, R. B.; Bishop, R.; Dance, I. G. J. Chem. Soc., Perkin Trans. 2 1990, 855-870.
30. (b) Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2311-2327.
31. (a) Desiraju, G. R. Polymorphism - the nemesis of crystal design? In Crystal Engineering: The Design of Organic Solids; Elsevier: Amsterdam, 1989; Chapter 10, pp 285-301.
32. (b) Bernstein, J.; Henck, J.-O. Cryst. Eng. 1998, 1, 119-128.
33. (c) Bernstein, J.; Davey, R. J.; Hencke, J.-O. Angew. Chem., Int. Ed. 1999, 38, 3440.
34. (d) Bernstein, J. Polymorphism in Molecular Crystals; Oxford Science Publications: Oxford, 2002.
35. (e) Braga, D; Brammer, L.; Champness, N. R. CrystEngComm 2005, 7, 1-5.
36. (f) Nangia, A. Acc. Chem. Res. 2008, 41, 595-604.
37. (g) Caira, M. R. Polymorphism. In Handbook of Thermal Analysis and Calorimetry, Vol. 5: Recent Advances, Techniques and Applications; Brown, M. E.; Gallagher, P. K., Eds.; Elsevier: Amsterdam, 2008; Chapter 16, pp 597-629.
38. (h) Fucke, K.; Qureshi, N.; Yufit, D. S.; Howard, J. A. K.; Steed, J. W. Cryst. Growth Des. 2010, 10, 880-886.
39. (a) Hatt, H. H. Rev. Pure Appl. Chem. 1956, 6, 153-190.
40. (b) Jeffrey, G. A. Acc. Chem. Res. 1969, 2, 344-352.
41. (c) Desiraju, G. R. J. Chem. Soc., Chem. Commun. 1991, 426-428.
42. (d) Custelcean, R.; Afloroaei, C.; Vlassa, M.; Polverejan, M. Angew. Chem., Int. Ed. 2000, 39, 3094-3096.
43. (e) Mascal, M.; Infantes, L.; Chisholm, J. Angew. Chem., Int. Ed. 2006, 45, 32-36.
44. (f) Van de Streek, J. CrystEngComm 2007, 9, 350-352.
45. (g) Sansam, B. C. R.; Anderson, K. M.; Steed, J. W. Cryst. Growth Des. 2007, 7, 2649-2653.
46. (h) Infantes, L.; Fabian, L.; Motherwell, W. D. S. CrystEngComm 2007, 9, 65-71.
47. (a) Ung, A. T.; Bishop, R.; Craig, D. C.; Dance, I. G.; Scudder, M. L. J. Chem. Soc., Chem. Commun. 1993, 322-323.
48. (b) Vishweshwar, P.; McMahon., J. A.; Zaworotko, M. J. Crystal Engineering of Pharmaceutical Co-Crystals. In Frontiers in Crystal Engineering; Tiekink, E. R. T., Vittal, J. J., Eds.; Wiley: Chichester, 2006; Chapter 2, pp 25-49.
49. (c) Lara-Ochoa, F.; Espinosa-Pérez, G. Supramol. Chem. 2007, 19, 553-557.
50. (d) Zaworotko, M. J. Cryst. Growth Des. 2007, 7, 4-9.
51. (e) Shan, N.; Zaworotko, M. J. Drug Discovery Today 2008, 13, 440-446.
52. (f) Friscic, T.; Jones, W. Cryst. Growth Des. 2009, 9, 1621- 1637.
53. (g) Ter Horst, J. H.; Deij, M. A.; Cains, P. W. Cryst. Growth Des. 2009, 9, 1531-1537.
54. (h) Anderson, K. M.; Probert, M. R.; Whiteley, C. N.; Rowland, A. M.; Goeta, A. E.; Steed, J. W. Cryst. Growth Des. 2009, 9, 1082-1087.
55. (a) McCrone, W. C. Polymorphism. In Physics and Chemistry of the Organic Solid State; Fox, D.; Labes, M. M.; Weissberger, A., Eds.; Wiley: New York, 1965; Vol. 2, p 725.
56. (b) Pidcock, E.; Motherwell, W. D. S. Cryst. Growth Des. 2004, 4, 611-620.
57. (c) Aldridge, S. The Shape Shif ters. In Chem. World, April 2007, 64-70.
58. (d) Threlfall, T. L. Analyst 1995, 120, 2435-2460.
59. (a) Ung, A. T.; Bishop, R.; Craig, D. C.; Dance, I. G.; Scudder, M. L. Tetrahedron 1993, 49, 639-648.
60. (b) Vippagunta, S. R.; Brittain, H. G.; Grant, D. J. W. Adv. Drug Delivery Rev. 2001, 48, 3-26.
61. (c) Braga, D.; Curzi, M.; Giaffreda, S. L.; Grepioni, F.; Maini, L.; Pettersen, A.; Polito, M. Nanoporous Crystals, Co-Crystals, Isomers and Polymorphs from Crystals. In Organic Nanostructures; Atwood, J. L.; Steed, J. W., Eds., Wiley-VCH Verlag: Weinheim, 2008; pp 155- 177.
62. (d) Nangia, A. Cryst. Growth Des. 2008, 8, 1079-1081.
63. (e) Nassimbeni., L.; Su, H.; Weber, E. New J. Chem. 2008, 32, 1702-1709.
64. (f) Nguyen, V. T.; Bishop, R.; Craig, D. C.; Scudder, M. L. CrystEngComm 2009, 11, 1275-1280.
65. (a) Almarsson, Ö.; Zaworotko, M. J. Chem. Commun. 2004, 1889-1896.
66. (b) Lara-Ochoa, F.; Espinosa-Pérez, G. Cryst. Growth Des. 2007, 7, 1213-1215.
67. Bertz, S. H.; Cook, J. M.; Gawish, A.; Weiss, U. Org. Synth. 1990, Coll. Vol. VII, 50-56.
68. (a) Brock, C. P. Acta Crystallogr., Sect. B 2002, 58, 1025-1031.
69. (b) Brock, C. P.; Duncan, L. L. Chem. Mater. 1994, 6, 1307-1312.
70. (c) Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Systems; Springer: Berlin, 1994.
71. (a) Gillon, A. L.; Feeder, N.; Davey, R. J.; Storey, R. Cryst. Growth. Des. 2003, 3, 663-673.
72. (b) Mascal, M.; Infantes, L.; Chisholm, J. Angew. Chem., Int. Ed. 2006, 45, 32-36.
73. (c) Sansam, B. C. R.; Anderson, K. M.; Steed, J. W. Cryst. Growth Des. 2007, 7, 2649- 2653.
74. (d) Infantes., L.; Fabian, L.; Motherwell, W. D. S. CrystEngComm 2007, 9, 65-71.
75. SADABS,; Bruker AXS Inc.: Madison, Wisconsin, USA, 2001.
76. APEX2 and SAINT,; Bruker AXS Inc.: Madison, Wisconsin, USA, 2001.
77. Sheldrick, G. M. Acta Crystallogr., Sect. A 2008, 64, 112-122.
78. Macrae, C. F.; Bruno, I. J.; Chisholm, J. A.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Rodriguez-Monge, L.; Taylor, R.; van de Streek, J.; Wood, P. A. Mercury CSD 2.0 - New features for the visualization and investigation of crystal structures. J. Appl. Crystallogr. 2008, 41, 466-470.