Sulfonamide-pyridine-N-oxide cocrystals

Crystal Growth and Design

Volumn 11, Issue 5, 2011, Pages 1930-1939

  Rajesh Goud, N ^a   Jagadeesh Babu, N ^a   Nangia, Ashwini ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CO-CRYSTALS; COCRYSTAL STRUCTURE; EXACT GEOMETRY; FUROSEMIDES; INFINITE CHAINS; MODEL STUDY; PYRIDINE-N-OXIDES; SUPRAMOLECULAR SYNTHESIS; TWO-POINT;

AMIDES; HYDROGEN; HYDROGEN BONDS; PYRIDINE; SYNTHESIS (CHEMICAL);

SULFUR COMPOUNDS;

EID: 79957940681     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg200094x     Document Type: Article

References (63)

1. Desiraju, G. R. Angew. Chem., Int. Ed. 1995, 34, 2311.
2. Walsh, R. D. B.; Bradner, M. W.; Fleischman, S. G.; Morales, L. A; Moulton, B.; Rodriguez-Hornedo, N.; Zaworotko, M. J. Chem. Commun. 2003, 186.
3. Allen, F. H.; Motherwell, W. D. S.; Raithby, P. R.; Shields, G. P.; Taylor, R. New. J. Chem. 1999, 23, 25.
4. Cambridge Crystallographic Data Center, Cambridge, U. K., www.ccdc.cam.ac.uk.
5. (a) Nangia, A.; Desiraju, G. R Top. Curr. Chem. 1998, 198, 57.
6. (b) Nangia, A; Desiraju, G. R Acta Crystallogr., Sect. A 1998, 54, 934.
7. (a) Etter, M. C; Macdonald, J. C; Bernstein, J. Acta Crystallogr., Sect. B 1990, 46, 256.
8. (b) Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N. L. Angew. Chem., Int. Ed. 1995, 34, 1555.
9. (a) Etter, M. C J. Phys. Chem. 1991, 95, 4601.
10. (b) Etter, M. C. Acc. Chem. Res. 1990, 23, 120.
11. (a) 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, 909.
12. (b) Vishweshwar, P.; McMahon, J. A.; Bis, J. A; Zaworotko, M. J. J. Pharm. Sci. 2006, 95, 499.
13. (a) Bhogala, B. R; Vishweshwar, P.; Nangia, A Cryst. Growth Des. 2002, 2, 325.
14. (b) Almarsson, Ö.; Zaworotko, M. J. Chem. Commun. 2004, 1889.
15. (c) Aakeröy, C. B.; Salmon, D. J. CrystEngComm 2005, 7, 439.
16. (d) Bhogala, B. R.; Nangia, A New J. Chem. 2008, 32, 800.
17. (e) Aakeröy, C. B.; Beatty, A. M.; Helfrich, B. A. Angew. Chem., Int. Ed. 2001, 40, 3240.
18. (a) Reddy, L. S.; Babu, N. J.; Nangia, A Chem. Commun. 2006, 1369.
19. (b) Babu, N. J.; Reddy, L. S.; Nangia, A. Mol. Pharmaceutics 2007, 4, 417.
20. (c) Babu, N. J.; Reddy, L. S.; Aitipamula, S.; Nangia, A. Chem. - An Asian J. 2008, 3, 1122.
21. Nangia, A. J. Chem. Sci. 2010, 122, 295.
22. (a) Yang, S. S.; Guillory, J. K. J. Pharm. Sci. 1972, 61, 26.
23. (b) Ko, S.-K.; Jin, H. J.; Jung, D.-W.; Tian, X.; Shin, I. Angew. Chem., Int. Ed. 2009, 48, 7809.
24. (c) Caira, M. R Mol. Pharmaceutics 2007, 4, 310.
25. (d) Byrn, S. R.; Pfeiffer, R. R; Stowell, J. G Solid-State Chemistry of Drugs; SSCI, Inc.: West Lafayette, IN, 1999; p 160.
26. (a) Ishida, T.; In, Y.; Doi, M.; Inoue, M.; Yanagisawa, I. Acta Crystallogr., Sect. B 1989, 45, 505.
27. (b) Leger, J. M.; Alberola, S.; Carpy, A. Acta Crystallogr. 1977, B33, 1455.
28. (c) Alberola, S.; Sabon, F.; Jaud et, J.; Galy, J. Acta Crystallogr. 1977, B33, 3337.
29. (d) Caira, M. R J. Chem. Crystallogr. 1994, 24, 695.
30. (e) Caira, M. R; Nassimbeni, L. R; Wilderwanck, A. F. J. Chem. Soc, Perkin Trans. 1995, 2, 2213.
31. (f) Caira, M. R. J. Crystallogr. Spectrosc. Res. 1992, 22, 193.
32. Eccles, K. S.; Elcoate, C. J.; Stokes, S. P.; Maguire, A. R.; Lawrence, S. E. Cryst. Growth Des. 2010, 10, 4243.
33. (a) Reddy, L. S.; Basavoju, S.; Vangala, V. R; Nangia, A. Cryst. Growth Des. 2006, 6, 161.
34. (b) Videnova-Adrabińska, V.; Janeczko, E. Chem. Commun. 1999, 1527.
35. (c) Custelcean, R.; Moyer, B. A.; Bryantsev, V. S.; Hay, B. P. Cryst. Growth Des. 2006, 6, 555.
36. (d) Custelcean, R. Chem. Commun. 2008, 295.
37. (e) Custelcean, R.; Sellin, B.; Moyer, B. A. Chem. Commun. 2007, 1541.
38. (a) Shan, N.; Toda, F.; Jones, W. Chem. Commun. 2002, 2372.
39. (b) Trask, A. V.; Jones, W. Top. Curr. Chem. 2005, 254, 131.
40. (a) Trask, A. V.; Motherwell, W. D. S.; Jones, W. Chem. Commun. 2004, 890.
41. (b) Friščić, T.; Trask, A. V.; Jones, W.; Motherwell, W. D. S. Angew. Chem., Int. Ed. 2006, 45, 7546.
42. Reddy, L. S.; Bhatt, P.; Banerjee, R.; Nangia, A.; Kruger, G. J. Chem. Asian J. 2007, 2, 505.
43. (a) Berry, D. J.; Seaton, C. C.; Clegg, W.; Harrington, R. W.; Coles, S. J.; Horton, P. N.; Hursthouse, M. B.; Storey, R; Jones, W.; Frišč ić, T.; Blagden, N. Cryst. Growth Des. 2008, 8, 1697.
44. (b) Bettinetti, G.; Caira, M. R.; Callegari, A.; Merli, M.; Sorrenti, M.; Tadini, C. J. Pharm. Sci. 2000, 89, 478.
45. (a) Saha, B. K.; Nangia, A.; Jaskólski, M. CrystEngComm 2005, 7, 355.
46. (b) Thaimattam, R.; Sharma, C. V. K.; Clearfield, A; Desiraju, G. R. Cryst. Growth Des. 2001, 1, 103.
47. International Union of Crystallography, Chester, U. K., checkcif. iucr.org.
48. Sanphui, P.; Sarma, B.; Nangia, A. Cryst. Growth Des. 2010, 10, 4550.
49. (a) Friedman, P. A.; Berndt, W. O. In Modern Pharmacology with Clinical Applications, 5th ed.; Craig, C. R., Stitzel, R. E., Eds.; Little Brown & Company: Boston, 1997; pp 239-255.
50. (b) Khan, M. G Encyclopedia of Heart Diseases; Elsevier: New York, 2006.
51. Babu, N. J.; Cherukuvada, S.; Thakuria, R.; Nangia, A Cryst. Growth Des. 2010, 10, 1979.
52. (a) Feng, S.; Yang, M.; Zhang, Z.; Wang, Z.; Hong, D.; Richter, H; Benson, G. M.; Bleicher, B.; Grether, U.; Martin, R. E; Plancher, J.-M.; Kuhn, B.; Rudolph, M. G; Chen, L. Biorg. Med. Chem. Lett. 2009, 19, 2595.
53. (b) McKeown, S. R.; Hejmadi, M. V.; McIntyre, I. A.; McAleer, J. J.; Patterson, L. H. Br. J. Cancer 1995, 72, 76.
54. (c) Nishida, C. R; Lee, M.; Ortiz de Montellano, P. R. Mol. Pharm. 2010, 78, 497.
55. SAINT-Plus, version 6.45; Bruker AXS: Madison, WI, 2003.
56. Sheldrick, G. M. SADABS, Program for Empirical Absorption Correction of Area Detector Data; University of Göttingen: Göttingen, Germany, 1997.
57. (a) RLATT, Reciprocal Lattice Viewer, version 3.0; Bruker AXS: Madison, WI, 2000.
58. (b) Sheldrick, G. M. CELL-NOW; University of Göttingen: Göttingen, Germany, 2004.
59. (a) SMART (Version 5.625) and SHELX-TL (Version 6.12); Bruker-AXS: Madison, WI, 2000.
60. (b) Sheldrick, G. M. SHELXS-97and SHELXL-97; University of Göttingen:, Göttingen, Germany, 1997.
61. Spek, A. L. PLATON: A Multipurpose Crystallographic Tool; Utrecht University: Utrecht, The Netherlands, 2002.
62. Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7.
63. Barbour, L. J. X-Seed, Graphical Interface to SHELX-97 and POV-Ray; University of Missouri-Columbia: Columbus, MO, 1999.