Supramolecular assembly of protonated xanthine alkaloids in their perchlorate salts

Crystal Growth and Design

Volumn 10, Issue 2, 2010, Pages 937-942

  Biradha, Kumar ^a   Samai, Suman ^a   Maity, Annada C ^b   Goswami, Shyamaprosad ^b  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

^b INDIAN INSTITUTE OF ENGINEERING SCIENCE AND TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 76349108072     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg9012685     Document Type: Article

References (46)

1. (a) Carlucci, L.; Gavezzotti, A. Chem. Eur. J. 2005, 11, 271.
2. (b) Lehmann, C, W.; Stowasser, F. Chem.-Eur. J. 2007, 13, 2908.
3. (c) Derollez, P.; Correia, N. T.; Danéde, F.; Capet, F.; Affouard, F.; Lefebvre, J.; Descamps, M. Acta Crystallogr. 2005, B61, 329.
4. (d) Enright, G. D.; Terskikh, V. V.; Brouwer, D. H.; Ripmeester, J. A. Cyst. Growth Des. 2007, 7, 1406.
5. (e) Matsuo, K.; Matsuoka, M. Cyst. Growth Des. 2007, 7, 411.
6. (f) Egawa, T.; Kamiya, A.; Takeuchi, H.; Konaka, S. J. Mol. Struct. 2006, 825,151.
7. (g) Balbuena, P. B.; Blocker, W.; Dudek, R. M.; Cabrales-Navarro, F. A.; Hirunsit, P. J. Phys. Chem. A 2008, 112, 10210.
8. (h) Ford, K. A.; Ebisuzaki, Y.; Boyle, P. D. Acta Crystallogr. 1998, C54, 1980.
9. (i) Smith, E. D. L.; Hammond, R. B.; Jones, M. J.; Roberts, K. J.; Mitchell, J. B. O.; Price, S. L.; Harris, R. K.; Apperley, D. C.; Cherryman, J C.; Docherty, R. J. Phys. Chem. B 2001, 105, 5818.
10. (j) Descamps, M.; Correia, N. T.; Derollez, P.; Danede, F.; Capet, F. J. Phys. Chem. B 2005, 109, 16092.
11. (k) Ebisuzaki, Y.; Boyle, P. D.; Smith, J. A. Acta Crystallogr. 1997, C53, 777.
12. (l) Edwards, H. G. M.; Lawson, E.; Matas, M.; Shields, L.; York, P. J. Chem. Soc., Perkin Trans. 2 1997, 1985.
13. (m) Sun, C.; Zhou, D.; Grant, D. J. W.; Young, V. G., Jr Acta Crystallogr. 2002, E58, 368.
14. Trask, A. V. Mol. Pharmaceutics 2007, 4, 301.
15. (a) Good, D. J.; Rodriguez-Hornedo, N. Cryst. Growth Des. 2009, 9, 2252.
16. (b) Rodriguez-Hornedo, N. Mol. Pharmaceutics 2007, 4, 299.
17. Reddy, L. S.; Babu, N. J.; Nangia, A. Chem. Commun. 2006, 1369.
18. Vishweshwar, P.; McMahon, J. A.; Peterson, M. L.; Hickey, M. B.; Shattock, T. R.; Zaworotko, M. J. Chem. Commun. 2005, 4601.
19. Bhatt, P. M.; Ravindra, N. V.; Banerjee, R.; Desiraju, G. R. Chem. Commun. 2005, 1073.
20. Remenar, J. F.; Morissette, S. L.; Peterson, M. L.; Moulton, B.; MacPhee, J. M.; Guzmán, H. R.; Almarsson, Ö. J. Am. Chem. Soc. 2003, 125, 8456.
21. Oswald, I. D. H.; Allan, D. R.; McGregor, P. A.; Motherwell, W. D. S.; Parsons, S.; Pulham, C. R. Acta Crystallogr. 2002, B58, 1057.
22. McNamara, D. P.; Childs, S. L.; Giordano, J.; Iarriccio, A.; Cassidy, J.; Shet, M. S.; Mannion, R.; O'Donnell, E.; Park, A. Pharm. Res. 2006, 23, 1888.
23. Chen, A. M.; Ellison, M. E.; Peresypkin, A.; Wenslow, R. M.; Variankaval, N.; Savarin, C G.; Natishan, T. K.; Mathre, D. J.; Dormer, P. G.; Euler, D. H.; Ball, R. G.; Ye, Z.; Wang, Y.; Santos, I. Chem. Commun. 2007, 419.
24. Childs, S. L.; Chyall, L. J.; Dunlap, J. T.; Smolenskaya, V. N.; Stahly, B. C.; Stahly, G. P. J. Am. Chem. Soc. 2004, 126, 13335.
25. (a) Karki, S.; Fábián, L.; Friščić, T.; Jones, W. Org. Lett. 2007, 9, 3133.
26. (b) Karki, S.; Friščió, T.; Fábián, L.; Laity, P. R.; Day, G. M.; Jones, W. Adv. Mater. 2009, 21, 1.
27. (c) Friščić, T.; Fábián, L.; Burley, J. C.; Reid, D. G.; Duerd, M. J.; Jones, W. Chem. Commun. 2008, 1644.
28. Chandramohan, A.; Bharathikannan, R.; Chandrasekaran, J.; Maadeswaran, P.; Renganathan, R.; Kandavelu, V. J. Cryst. Growth. 2008, 310, 5409.
29. Trask, A. V.; Motherwell, W. D. S.; Jones, W. Cryst. Growth Des. 2005, 5, 1013.
30. (a) Bučar, D -K.; Henry, R. F.; Lou, X.; Borchardtd, T. B.; Zhang, G. G. Z. Chem. Commun. 2007, 525.
31. (b) Bučar, D -K.; Henry, R F.; Lou, X.; Duerst, R.; MacGillivray, L. R.; Zhang, G. Z. Cyst. Growth Des. 2009, 9, 1932.
32. (a) Bán, M.; Bombiez, P.; Madarász, J. J. Therm. Anal Calorim. 2009, 95, 895.
33. (b) Trask, A. V.; Motherwell, W. D. S.; Jones, W. Int. J. Pharm. 2006, 320, 114.
34. Lu, J.; Rohani, S. Org. Process Res. Dev. DOI: 10.1021/op900047r.
35. Aitipamula, S.; Chow, P. S.; Tan, R. B. H. Acta Crystallogr. 2009, E65, 2126.
36. Mahapatra, A. K.; Sahoo, P.; Goswami, S.; Chantrapromma, S.; Fun, H -K. Tetrahedron Lett. 2009, 50, 89.
37. Cassidy, A. M. C.; Gardner, C. E.; Jones, W. Int. J. Pharm. 2009, 379, 59.
38. (a) Biradha, K.; Mahata, G. Cryst. Growth Des. 2005, 5, 49.
39. (b) Santra, R.; Biradha, K Cryst. Growth Des. 2009, 9, 4969.
40. (c) Santra, R.; Ghosh, N.; Biradha, K New. J. Chem. 2008, 1673.
41. Goswami, S.; Maity, A. C.; Fun, H.-K. Eur. J. Org. Chem. 2007, 4056.
42. Samai, S.; Biradha, K., unpublished results, Space group = P1̄, a = 5.044(1) Å,b = 7.454(2) Å, c = 12.158(3) Å, α = 80.297(7)°, β = 80.815(7)°, γ = 75.700(7)°; C8-N9 = 1.343(3) Å, N7-C8 = 1.319 Å.
43. Mizuno, H.; Fujiwara, T.; Tomita, K. Bull. Chem. Soc. Jpn. 1969, 42, 3099.
44. CSD version 5.30 (November-2008 update) was used. Allen, F. H.; Kennard, O. Chem. Des. Automat. News 1993, 8, 31.
45. Wang, W.-D.; Wang, H.; Feng, W.-J.; Jin, Z.-M.; Hu, M.-L. Z. Kristallogr,-New Cryst. Struct. 2006, 221, 375.
46. Sheldrick, G. M. SHELX-97, Program for the Solution and Refinement of Crystal Structures; University of Göttingen: Germany, 1997.