Topological analysis of charge density distribution in concomitant polymorphs of 3-acetylcoumarin, a case of packing polymorphism

Crystal Growth and Design

Volumn 6, Issue 3, 2006, Pages 708-718

  Munshi, Parthapratim ^a   Row, Tayur N Guru ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33645287015     PISSN: 15287483     EISSN: None     Source Type: Journal    
DOI: 10.1021/cg050484g     Document Type: Article

References (69)

1. Bernstein, J. Prog. Clin. Biol. Res. 1989, 289, 203-215.
2. Brittain, H. G. Polymorphism in Pharmaceutical Solids; Marcel Dekker: New York, 1999; Vol. 95.
3. Bernstein, J. Polymorphism in Molecular Crystals; Oxford University Press: Oxford, Great Britain, 2002.
4. Allen, F. H. Acta Crystallogr. B 2002, 58, 380-388.
5. Allen, F. H.; Motherwell, W. D. S. Acta Crystallogr. B 2002, 58, 407-422.
6. 1/n (Z = 4, Z′ = 1). It is of interest to note that there is only one reported example (CSD Refcode: HAZFAP, 4, 4′-bipyridinium salt of squaric acid; Reetz, M.T.; Höger, S.; Harms, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 181-183.), which is concomitant.
7. Vrcelj, R. M.; Gallagher, G. H.; Sherwood, J. N. J. Am. Chem. Soc. 2001, 123, 2291-2295.
8. Davey, R. J.; Blagden, N.; Righini, S.; Alison, H.; Quayle, M. J.; Fuller, S. Cryst. Growth Des. 2001, 1, 59-65 and references therein.
9. Bernstein, J.; Davey, R. J.; Henck, J.-O. Angew. Chem., Int. Ed. Engl. 1999, 38, 3440-3461.
10. Reed, S. M.; Weakley, T. J. R.; Hutchison, J. E. Cryst. Eng. 2000, 3, 85-99.
11. Coppens, P. X-ray Charge Densities and Chemical Bonding; Oxford University Press: Oxford, 1997.
12. Hohenberg, P.; Kohn, W. Phys. Rev. B 1964, 136, 864-871.
13. Overgaard, J.; Hibbs, D. E. Acta Crystallogr. A 2004, 60, 480-487.
14. Kulkarni, G. U.; Kumaradhas, P.; Rao, C. N. R. Chem. Mater. 1998, 10, 3498-3505.
15. Gopalan, R. S.; Kulkarni, G. U.; Rao, C. N. R. ChemPhysChem 2000, 1, 127-135.
16. Whitten, A. E.; Dittrich, B.; Spademan, M. A.; Turner, P.; Brown, T. C. Dalton Trans. 2004, 23-29.
17. Munshi, P.; Venugopala, K. N.; Jayashree, B. S.; Guru Row, T. N. Cryst. Growth Des. 2004, 4, 1105-1107.
18. Pichon-Pesme, V.; Lecomte, C. Acta Crystallogr. Sect. B 1998, 54, 485-493.
19. Overgaard, J.; Schiøtt, B.; Larsen, F. K.; Iversen, B. B. Chem. Eur. J. 2001, 7, 3756-3767.
20. Hambley, T. W.; Hibbs, D. E.; Turner, P.; Howard, S. T.; Hursthouse, M. B. J. Chem. Soc., Perkin Trans. 2 2002, 235-239.
21. Gatti, C.; May, E.; Destro, R.; Cargnoni, F. J. Phys. Chem. A 2002, 106, 2707-2720.
22. Overgaard, J.; Waller, M. P.; Platts, J. A.; Hibbs, D. E. J. Phys. Chem. A 2003, 107, 11201-11208.
23. Munshi, P.; Guru Row, T. N. J. Phys. Chem. A 2005, 109, 659-672.
24. Coppens, P. Acta Crystallogr. A 1998, 54, 779-788.
25. Hansen, N. K.; Coppens, P. Acta Crystallogr. A 1978, 34, 909-921.
26. Bader, R. F. W. Atoms in Molecules: A Quantum Theory; Oxford University Press: Oxford, U.K. 1990.
27. Bader, R. F. W. J. Phys. Chem. A 1998, 102, 7314-7323.
28. Koch, U.; Popelier, P. L. A. J. Phys. Chem. 1995, 99, 9747-9754.
29. Popelier, P. Atoms in Molecules. An Introduction; Prentice Hall, UK, 2000; pp 150-153.
30. (a) Bondi, A. J. Phys. Chem. 1964, 68, 441-451.
31. (b) Nyburg, S. C.; Faerman, C. H. Acta Crystallogr. B 1985, 41, 274-279.
32. Knoevenagel, F. Ber. Dtsch. Chem. Ges. 1898, 31, 732.
33. Munshi, P.; Guru Row, T. N. Acta Crystallogr. B 2002, 58, 1011-1017.
34. Munshi, P.; Guru Row, T. N. Acta Crystallogr. B 2003, 59, 159.
35. Bruker. SMART (V5.628), SAINT (V6.45a), Bruker AXS Inc., Madison, WI, 2004.
36. Blessing, R. H. Crystallogr. Rev. 1987, 1, 3-58.
37. Sheldrick, G. M. SHELXS97 and SHELXL97, program for crystal structure refinement; University of Göttingen, Germany, 1997.
38. Farrugia, L. J. WinGX, Version 1.64.05. J. Appl. Crystallogr. 1999, 32, 837-838.
39. Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565.
40. Nardelli, M. J. Appl Crystallogr. 1995, 28, 569.
41. Koritsanszky, T. S.; Howard, S.; Macchi, P.; Gatti, C.; Farrugia, L. J.; Mallinson, P. R.; Volkov, A.; Su, Z.; Richter, T.; Hansen, N. K. XD (version 4.10, July), a computer program package for multipole refinement and analysis of electron densities from diffraction data; Free University of Berlin, Germany; University of Wales, Cardiff, UK.; Università di Milano, U.K.; CNR-ISTM, Milano, U.K.; University of Glasgow, U.K.; State University of New York, Buffalo, USA.; University of Nancy, France, 2003.
42. Clementi, E.; Roetti, C. At. Data Nucl. Data Tables 1974, 14, 177-478.
43. Allen, F. H. Acta Crystallogr. B 1986, 42, 515-522.
44. (a) Abramov, Y. A.; Volkov, A.; Wu, G.; Coppens, P. Acta Crystallogr. A 2000, 56, 585-591.
45. (b) Kisiel, Z. PROSPE, Programs for ROtational SPEctroscopy, http://info.ifpan.edu.pl/~kisiel/ prospe.htm.
46. Spackman, M. A. J. Chem. Phys. 1986, 38, 6587-6601.
47. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. GAUSSIAN 98; Gaussian, Inc.: Pittsburgh, PA, 1998.
48. Abramov, Y. A.; Volkov, A.; Wu, G.; Coppens, P. J. Phys. Chem. B 2000, 104, 2183-2188.
49. Saunders, V. R.; Dovesi, R.; Roetti, C.; Causa, M.; Harrison, N. M.; Orlando, R.; Zicovich-Wilson, C. M. CRYSTAL03 1.0 User's Manual; University of Torino and CCLRC, 2003.
50. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
51. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
52. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213-222.
53. Oddershede, J.; Larsen, S. J. Phys. Chem. A 2004, 108, 1057-1063.
54. Spackman, M. A.; Mitchell, A. M. Phys. Chem. Chem. Phys. 2001, 3, 1518-1523.
55. Boys, S. R; Bernardi, F. Mol. Phys. 1970, 19, 553-566.
56. Hirshfeld, F. L. Acta Crystallogr. A 1976, 32, 239-244.
57. Mallinson, P. R.; Smith, G. T.; Wilson, C. C.; Grech, E.; Woz'niak, K. J. Am. Chem. Soc. 2003, 125, 4259-4270.
58. Hibbs, D. E.; Overgaard, J.; Piltz, R. O. Org. Biomol. Chem. 2003, 1, 1191-1198.
59. May, E.; Destro, R.; Gatti, C. J. Am. Chem. Soc. 2001, 123, 12248-12254 and the references therein.
60. Abramov, Y. A. Ada Crystallogr. A 1997, 53, 264-272.
61. Espinosa, E.; Molins, E.; Lecomte, C. Chem. Phys. Lett. 1998, 285, 170-173.
62. Moorthy, J. N.; Samant, S. D.; Venkatesan, K. J. Chem. Soc., Perkin Trans. 2 1994, 1223-1228.
63. Yang, X.; Wu, D.; Ranford, J. D.; Vittal, J. J. Cryst. Growth Des. 2005, 5, 41-43 and the references therein.
64. Abramov, Y. A.; Volkov, A.; Coppens, P. Chem. Phys. Lett. 1999, 311, 81-86.
65. Abramov, Y. A.; Volkov, A.; Coppens, P. J. Mol. Struct. (THEO-CHEM) 2000, 529, 27-35.
66. Stone, A. J.; Tsuzuki, S. J. Phys. Chem. B 1997, 101, 10178-10183.
67. Cárdenas-Jirón, G. I.; Masunov, A.; Dannenberg, J. J. J. Phys. Chem. A 1999, 103, 7042-7046.
68. McKinnon, J. J.; Spademan, M. A.; Mitchell, A. S. Acta Crystallogr. B 2004, 60, 627-668.
69. Politzer, P.; Murray, J. S. Theo. Chem. Acc. 188, 134-142.