Hierarchy of supramolecular synthons: Persistent hydroxyl⋯pyridine hydrogen bonds in cocrystals that contain a cyano acceptor

Molecular Pharmaceutics

Volumn 4, Issue 3, 2007, Pages 401-416

  Bis, Joanna A ^a   Vishweshwar, Peddy ^a   Weyna, David ^a   Zaworotko, Michael J ^a  

^a UNIVERSITY OF SOUTH FLORIDA   (United States)

Author keywords

Cambridge Structural Database; Cocrystal; Pharmaceutical cocrystal; Polymorphism in cocrystals; Supramolecular heterosynthon

Indexed keywords

4,4' BIPYRIDINE; BICALUTAMIDE; HEXADECANOL; HYDROXYL GROUP; NITRILE; PHLOROGLUCINOL; PYRIDINE; RESORCINOL;

ARTICLE; BINDING SITE; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; HYDROGEN BOND; PRIORITY JOURNAL;

CHEMISTRY, PHARMACEUTICAL; CRYSTALLIZATION; CRYSTALLOGRAPHY, X-RAY; CYANIDES; HYDROGEN BONDING; HYDROXIDES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHARMACEUTICAL PREPARATIONS; PYRIDINES;

EID: 34250891895     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp070012s     Document Type: Article

References (84)

1. (A) Desiraju, G. R. Crystal Engineering: the Design of Organic Solids; Elsevier: Amsterdam, 1989.
2. (B) Braga, D. Chem. Commun. 2003, No. 22, 2751-2754.
3. (C) Moulton, B.; Zaworotko, M. J. Chem. Rev. 2001, 101 (6), 1629-1658.
4. Pepinsky, R. Phys. Rev. 1955, 100 (3), 97.
5. Schmidt, G. M. J. Pure Appl. Chem. 1971, 27, 647-678.
6. Lehn, J. M. Supramolecular Chemistry: Concepts and Perspectives; VCH: Weinheim, 1995.
7. MacGillivray, L. R.; Atwood, J. L. J. Am. Chem. Soc. 1997, 119 (29), 6931-6932.
8. Huang, K. S.; Britton, D.; Etter, M. C.; Byrn, S. R. J. Mater. Chem. 1997, 7 (5), 713-720.
9. Anthony, J. E.; Brooks, J. S.; Eaton, D. L.; Parkin, S. R. J. Am. Chem. Soc. 2001, 123 (38), 9482-9483.
10. Foxman, B. M.; Guarrera, D. J.; Taylor, L.D.; VanEngen, D.; Warner, J. C. Mater. Res. Bull. 1998, 109-118.
11. Almarsson, O.; Zaworotko, M. J. Chem. Commun. 2004, No. 17, 1889-1896.
12. Vishweshwar, P.; McMahon, J.; Bis, J.; Zaworotko, M. J. J. Pharm. Sci. 2006, 95, 1-18.
13. McMahon, J.; Bis, J. A.; Vishweshwar, P.; Shattock, T. R.; McLaughlin, O. L.; Zaworotko, M. J. Z. Kristallogr. 2005, 220 (4), 340-350.
14. Trask, A. V.; Motherwell, S. W.D.; Jones, W. Int. J. Pharm. 2006, 320, 114-123.
15. Li, Z. J.; Abramov, Li, Z. J.; Abramov, Y.; Bordner, J.; Leonard, J.; Medek, A.; Trask, A. V. J. Am. Chem. Soc. 2006, 128, 8199-8210.
16. Childs, S. L.; Chyall, L. J.; Dunlap, J. T.; Smolenskaya, V. N.; Stahly, B. C.; Stahly, G. P. J. Am. Chem. Soc. 2004, 126 (41), 13335-13342.
17. Peterson, Matthew L.; Hickey, Magali B.; Zaworotko, Michael J.; Almarsson, O. J. Pharm. Pharm. Sci. 2006, 9 (3), 317-326.
18. Vishweshwar, P.; McMahon, J.; Peterson, Matthew L.; Hickey, Magali B.; Shattock, T. R.; Zaworotko, M. J. Chem. Comm. 2005, 4601-4603.
19. Zaworotko, M. J. Cryst. Growth Des. 2007, 7, 4-9.
20. (A) MacGillivray, L. R.; Reid, J. L.; Ripmeester, J. A. J. Am. Chem. Soc. 2000, 122, 7817-7818.
21. (B) Fowler, F. W.; Lauher, J. W. J. Phys. Org. Chem. 2000, 13, 850.
22. (C) Etter, M. C.; Frankenbach, G. M.; Bernstein, J. Tetrahedron Lett. 1989, 30, 3617.
23. Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34 (21), 2311-2327.
24. Steiner, T. Angew. Chem., Int. Ed. 2002, 41 (1), 48-76.
25. Etter, M. C. J. Phys. Chem. 1991, 95 (12), 4601-4610.
26. Etter, M. C. Acc. Chem. Res. 1990, 23 (4), 120-126.
27. Aakeroy, C. B.; Beatty, A. M. Aust. J. Chem. 2001, 54, 409-421.
28. Thalladi, V. R.; Goud, B. S.; Hoy, V. J.; Allen, F. H.; Howard, J. A. K.; Desiraju, G. R. Chem. Commun. 1996, (3), 401-402.
29. Walsh, R. D. B.; Bradner, M. W.; Fleischman, S.; Morales, L. A.; Moulton, B.; Rodriguez-Hornedo, N.; Zaworotko, M. J. Chem. Commun. 2003, No. 2, 186-187.
30. Bis, J. A.; Zaworotko, M. J. Cryst. Growth Des. 2005, 5 (3), 1169-1179.
31. Steiner, T. Acta Crystallogr., Sect. B: Struct. Sci. 2001, 57, 103-106.
32. Vishweshwar, P.; Nangia, A.; Lynch, V. M. Cryst. Growth Des. 2003, 3 (5), 783-790.
33. Vishweshwar, P.; Nangia, A.; Lynch, V. M. J. Org. Chem. 2002, 67 (2), 556-565.
34. Etter, M. C.; Adsmond, D. A. J. Chem. Soc., Chem. Commun. 1990, (8), 589-591.
35. Aakeroy, C. B.; Beatty, A. M.; Helfrich, B. A. J. Am. Chem. Soc. 2002, 124 (48), 14425-14432.
36. Bhogala, B. R.; Vishweshwar, P.; Nangia, A. Cryst. Growth Des. 2002, 2 (5), 325-328.
37. Fleischman, S. G.; Kuduva, S. S.; Mcmahon, J. A.; Moulton, B.; Walsh, R. D. B.; Rodriguez-Hornedo, N.; Zaworotko, M. J. Cryst. Growth Des. 2003, 3 (6), 909-919.
38. Reddy, L. S.; Nangia, A.; Lynch, V. M. Cryst. Growth Des. 2004, 4 (1), 89-94.
39. Videnovaadrabinska, V.; Etter, M. C. J. Chem. Crystallogr. 1995, 25 (12), 823-829.
40. Leiserowitz, L.; Nader, F. Acta Crystallogr., Sect. B: Struct. Sci. 1977, 33 (SEP15), 2719-2733.
41. Vangala, V. R.; Mondal, R.; Broder, C. K.; Howard, J. A. K.; Desiraju, G. R. Cryst. Growth Des. 2005, 5 (1), 99-104.
42. Vishweshwar, P.; Nangia, A.; Lynch, V. M. CrystEngComm 2003, 5, 164-168.
43. Papaefstathiou, G. S.; Macgillivray, L. R. Org. Lett. 2001, 3 (24), 3835-3838.
44. Allen, F. H. Acta Crystallogr. 2002, B58, 380-388.
45. Goud, B. S.; Reddy, P. K.; Panneerselvam, K.; Desiraju, G. R. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1995, 51, 683-685.
46. Sharma, C. V. K.; Panneerselvam, K.; Pilati, T.; Desiraju, G. R. J. Chem. Soc., Perkin Trans. 2 1993, No. 11, 2209-2216.
47. Desiraju, G. R.; Sarma, J. A. R. P. J. Chem. Soc., Chem. Commun. 1983, No. 1, 45-46.
48. Aakeroy, C. B.; Desper, J.; Helfrich, B. A. CrystEngComm 2004, 6, 19-24.
49. Schmidt, J.; Snipes, W. Int. J. Radiat. Biol. 1967, 13, 101-109.
50. Desiraju, G. R. CrystEngComm 2003, 5, 466-467.
51. Dunitz, J. D. CrystEngComm 2003, 5, 506.
52. Aakeroy, C. B.; Salmon, D. J. CrystEngComm 2005, 7, 439-448.
53. Ling, A. R.; Baker, J. L. J. Chem. Soc. 1893, 63, 1314.
54. Anderson, J. S. Nature 1937, 140, 583-584.
55. Buck, J. S.; Ide, W. S. J. Am. Chem. Soc. 1931, 53, 2784-2787.
56. Vanniekerk, J. N.; Saunder, D. H. Acta Crystallogr. 1948, 1 (1-6), 44.
57. Hall, B.; Devlin, J. P. J. Phys. Chem. 1967, 71 (2), 465-466.
58. Pekker, S.; Kováts, É.; Oszlányi, G.; Bényei, G.; Klupp, G.; Bortel, G.; Jalsovszky, I.; Jakab, E.; Borondics, F.; Kamarás, K.; Bokor, M.; Kriza, G.; Tompa K.; Faigel, G. Nat. Mater. 2005, 4, 764.
59. Wöhler F. Justus Liebigs Ann. Chem. 1844, 51, 153.
60. The CSD search consisted of narrowing down lists of H-bonded structures to 2 or more components whose melting points are above 25°C, have 3D coordinates, organics only, and was accompanied by manual verification so to not include any hydrates, solvates, or salts.
61. Remenar, J. F.; Morissette, S. L.; Peterson, M. L.; Moulton, B.; Macphee, J. M.; Guzman, H. R.; Almarsson, O. J. Am. Chem. Soc. 2003, 125 (28), 8456-8457.
62. Trask, A. V.; Motherwell, W. D. S.; Jones, W. Cryst. Growth Des. 2005, 5 (3), 1013-1021.
63. (A) Bernstein, J. Polymorphism in Molecular Crystals; Clarendon Press: Oxford, U.K., 2002.
64. (B) Haleblian, J. K. J. Pharm. Sci. 1975, 64, 1269-1288.
65. Trask, A. V.; Jones, W. Top. Curr. Chem. 2005, 254, 41-70.
66. Kolvenbag Gjcm; Blackledge, G. R. P.; Gotting-Smith, K. Prostate 1998, 34, 61.
67. Shan, N.; Toda, F.; Jones, W. Chem. Commun. 2002, No. 20, 2372-2373.
68. Trask, A. V.; Motherwell, W. D. S.; Jones, W. Chem. Commun. 2004, No. 7, 890-891.
69. SADABS [Area-Detector Absorption Correction]; Siemens Industrial Automation, Inc.: Madison, WI, 1996.
70. Sheldrick, G. M. SHELXTL; University of Göttingen: Göttingen, Germany, 1997.
71. CSD, August 2006 release. Search parameters: organics only, 3D coordinates determined, R < 7.5%. All statistics presented in this section relate to OH Narom and CN moieties and their engagament in forming synthons I, II, and III in the absence of other functional groups.
72. Biradha, K.; Zaworotko, M. J. J. Am. Chem. Soc. 1998, 120 (25), 6431-6432.
73. There are 197 crystal structures that contain only OH and Narom moieties and no other hydrogen-bonding groups. After manual elimination of structures sustained by intramolecular OH⋯Narom hydrogen bonds, the set was reduced to 136 structures. In 135 (99%) entries the supramolecular heterosynthon I was observed. In one entry, REPPEH, I is absent due to a steric hindrance of the Narom moiety. The 27% (37 entries) of OH⋯OH homosynthon occurrence is due to the presence of multiple OH moieties.
74. Boenigk, D.; Mootz, D. J. Am. Chem. Soc. 1988, 110 (7), 2135-2139.
75. - bond, the charge of the oxygen was set to -1 and the number of bonded atoms was set to 1.
76. Etter, M. C.; MacDonald, J. C.; Bernstein, J. Acta Crystallogr., Sect. B: Struct. Sci. 1990, B46, 256-262.
77. MacGillivray, L. R.; Reid, J. L.; Ripmeester, J. A. J. Am. Chem. Soc. 2000, 122 (32), 7817-7818.
78. CSD search for the distance distribution of the NH⋯Narom interaction (organics, 3D coordinates determined, and R < 7.5%) afforded 420 entries that occur within a range of 2.75-3.30 Å, with the average of 3.0(1) Å.
79. Bernstein, J.; Davey, R. J.; Henck, J. O. Angew. Chem., Int. Ed. 1999, 38 (23), 3441-3461.
80. Bis, J. A.; Vishweshar, P.; Middleton, R.; Zaworotko, M. J. Cryst. Growth Des. 2006, 6 (4), 1048-1053.
81. Bis, J. A. Ph.D. Thesis, University of South Florida, Tampa, FL, 2006.
82. Trask, A. V.; Shan, N.; Motherwell, W. D. Samuel; Jones, W.; Feng, S.; Tan, R. B. H.; Carpenter, J. Chem Commun. 2005, No. 7, 880-882.
83. 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., Ed.; Wiley: Chichester, U.K., 2006.
84. McCrone, W. C. Phys. Chem. Org. Solid State 1965, 2, 725-767.