R-free factor and experimental charge-density analysis of 1-(2′-aminophenyl)-2-methyl-4-nitroimidazole: A crystal structure with Z′ = 2

Acta Crystallographica Section B: Structural Science

Volumn 67, Issue 4, 2011, Pages 365-378

  Paul, Agnieszka ^a,b   Kubicki, MacIej ^a   Jelsch, Christian ^b   Durand, Pierrick ^b   Lecomte, Claude ^b  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

^b Nancy University CNRS   (France)

Author keywords

anharmonic model; experimental charge density; free R factor; hydrogen bonds; hydrogen hydrogen interactions; multipole Hansen Coppens model; nitroimidazole derivative

Indexed keywords

ANHARMONIC MODEL; EXPERIMENTAL CHARGE DENSITY; HYDROGEN-HYDROGEN INTERACTIONS; MULTIPOLE HANSEN-COPPENS MODEL; NITROIMIDAZOLE DERIVATIVE; R FACTOR;

CARRIER CONCENTRATION; DIMERS; FUNCTIONAL GROUPS; HYDROGEN; HYDROGEN BONDS; VAN DER WAALS FORCES;

CRYSTAL STRUCTURE;

EID: 79960681213     PISSN: 01087681     EISSN: None     Source Type: Journal    
DOI: 10.1107/S0108768111022683     Document Type: Article

References (67)

1. Abramov, Yu. A. (1997). Acta Cryst. A53, 264-272.
2. Allen, F. H., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (2006). International Tables for Crystallography, Vol. C, 1st online ed., ch. 9.5, pp. 790-811. Chester: International Union of Crystallography.
3. Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.
4. Bader, R. F. W. (1990). Atoms in Molecules: A Quantum Theory. Oxford: Clarendon Press.
5. Bendeif, E.-E., Lecomte, C. & Dahaoui, S. (2009). Acta Cryst. B65, 59-67.
6. Blessing, R. H. (1987). Cryst. Rev. 1, 3-58.
7. Bondi, A. (1964). J. Phys. Chem. 68, 441-451.
8. Bouhmaida, N., Bonhomme, F., Guillot, B., Jelsch, C. & Ghermani, N. E. (2009). Acta Cryst. B65, 363-374.
9. Brünger, A. T. (1992). Nature, 355, 472-475.
10. Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.
11. Clementi, E. & Roetti, C. (1974). At. Data Nucl. Data Tables, 14, 177-478.
12. Coppens, P., Abramov, Y., Carducci, M., Korjov, B., Novozhilova, I., Alhambra, C. & Pressprich, M. R. (1999). J. Am. Chem. Soc. 121, 2585-2593.
13. De Bondt, H. L., Blaton, N. M., Peeters, O. M., De Ranter, C. J. & Kjøller-Larsen, I. (1991). The Application of Charge Density Research to Chemistry and Drug Design, edited by G. A. Jeffrey & J. F. Piniella, NATO ASI Series (Series B: Physics), Vol. 250, pp. 341-349. New York: Plenum Press.
14. Domagala, S. & Jelsch, C. (2008). J. Appl. Cryst. 41, 1140-1149.
15. Edwards, D. I. (1981). Prog. Med. Chem. 18, 87-116.
16. Epstein, J., Ruble, J. R. & Craven, B. M. (1982). Acta Cryst. B38, 140-149.
17. Espinosa, E., Souhassou, M., Lachekar, H. & Lecomte, C. (1999). Acta Cryst. B55, 563-572.
18. Fournier, B., Bendeif, E.-E., Guillot, B., Podjarny, A., Lecomte, C. & Jelsch, C. (2009). J. Am. Chem. Soc. 131, 10929-10941.
19. Grabowski, S. (2006). Editor. Hydrogen Bonding - New Insights, pp. 337-375. New York: Springer.
20. Guillot, B. (2010). MoProViewer: a Molecular Viewer Dedicated to Charge Density Analysis, Poster No. P19 presented at the French Cryst. Ass. AFC2010 (Strasbourg). 7-10 July 2010, http://www.crm2.uhp-nancy.fr/crm2/fr/labo/equipes/ emqc/.
21. Guillot, B., Jelsch, C., Podjarny, A. & Lecomte, C. (2008). Acta Cryst. D64, 567-588.
22. Guillot, R., Muzet, N., Dahaoui, S., Lecomte, C. & Jelsch, C. (2001). Acta Cryst. B57, 567-578.
23. Guillot, B., Viry, L., Guillot, R., Lecomte, C. & Jelsch, C. (2001). J. Appl. Cryst. 34, 214-223.
24. Hansen, N. K. & Coppens, P. (1978). Acta Cryst. A34, 909-921.
25. Herbst-Irmer, R., Henn, J. & Meindl, K. (2010). ECM, poster MS37-P04. Darmstadt, Germany.
26. Hernández-Trujillo, J. & Matta, C. F. (2007). Struct. Chem. 18, 849-857.
27. Hirshfeld, F. L. (1976). Acta Cryst. A32, 239-244.
28. Hoser, A. A., Dominiak, P. M. & Woźniak, K. (2009). Acta Cryst. A65, 300-311.
29. Jelsch, C., Guillot, B., Lagoutte, A. & Lecomte, C. (2005). J. Appl. Cryst. 38, 38-54.
30. Koch, U. & Popelier, P. L. A. (1995). J. Chem. Phys. 99, 9747-9754.
31. Koritsanszky, T. (2006). Hydrogen Bonding - New Insights, edited by S. J. Grabowski, pp. 441-470. Berlin: Springer.
32. Koritsanszky, T. S. & Coppens, P. (2001). Chem. Rev. 101, 1583-1627.
33. Kubicki, M. (2004a). Acta Cryst. C60, o255-o257.
34. Kubicki, M. (2004b). J. Mol. Struct. 698, 67-73.
35. Kubicki, M. (2005). J. Mol. Struct. 743, 209-215.
36. Kubicki, M., Borowiak, T., Dutkiewicz, G., Souhassou, M., Jelsch, C. & Lecomte, C. (2002). J. Phys. Chem. B, 106, 3706-3714.
37. Kubicki, M., Borowiak, T., Suwiński, J. & Wagner, P. (2001). Acta Cryst. C57, 106-108.
38. Kubicki, M. & Wagner, P. (2007). Acta Cryst. C63, o454-o457.
39. Kubicki, M. & Wagner, P. (2008). J. Mol. Struct. 876, 134-139.
40. Kuhs, W. F. (1992). Acta Cryst. A48, 80-98.
41. Kulda, J. & Hrdý, I. (2008). Microbiol. Monogr. 9, 179-199.
42. Larson, A. C. & Von Dreele, R. B. (1994). GSAS. Los Alamos National Laboratory Report. Los Alamos National Laboratory, Los Alamos, USA.
43. Liebschner, D., Elias, M., Moniot, S., Fournier, B., Scott, K., Jelsch, C., Guillot, B., Lecomte, C. & Chabriere, E. (2009). J. Am. Chem. Soc. 13, 7879-7886.
44. 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. (2008). J. Appl. Cryst. 41, 466-470.
45. Madhavi, N. N. L., Katz, A. K., Carrell, H. L., Nangia, A. & Desiraju, G. R. (1997). J. Chem. Soc. Chem. Commun. pp. 1953-1954.
46. Madsen, A. Ø. (2006). J. Appl. Cryst. 39, 757-758.
47. Mantina, M., Chamberlin, A. C., Valero, R., Cramer, C. J. & Truhla, D. G. (2009). J. Phys. Chem. A, 113, 5806-5812.
48. Matta, C. F., Hernández-Trujillo, J., Tang, T. H. & Bader, R. F. W. (2003). Chem. Eur. J. 9, 1940-1951.
49. Meindl, K., Herbst-Irmer, R. & Henn, J. (2010). Acta Cryst. A66, 362-371.
50. Munshi, P. & Row, T. N. G. (2005a). J. Phys. Chem. A, 109, 659-672.
51. Munshi, P. & Row, T. N. G. (2005b). Cryst. Rev. 11, 199-241.
52. Munshi, P. & Row, T. N. G. (2006). Acta Cryst. B62, 612-626.
53. Muzet, N., Guillot, B., Jelsch, C., Howard, E. & Lecomte, C. (2003). Proc. Natl. Acad. Sci. 100, 8742-8747.
54. Oxford Diffraction (2009). CrysAlis PRO, Version 1.171.33.36d. Oxford Diffraction Ltd, Yarnton, England.
55. Paul, A. (2011). J. Phys. Chem. A. Submitted for publication.
56. Ranganathan, A., Kulkarni, G. U. & Rao, C. N. R. (2003). J. Mol. Struct. 656, 249-263.
57. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
58. Sørensen, H. O., Stewart, R. F., McIntyre, G. J. & Larsen, S. (2003). Acta Cryst. A59, 540-550.
59. Stash, A. & Tsirelson, V. (2002). J. Appl. Cryst. 35, 371-373.
60. Stewart, R. F. (1991). The Application of Charge Density Research to Chemistry and Drug Design, edited by G. A. Jeffrey & J. F. Piniella, NATO ASI Series (Series B: Physics), Vol. 250, pp. 63-101. New York: Plenum Press.
61. Toby, B. H. (2001). J. Appl. Cryst. 34, 210-213.
62. Volkov, A., Macchi, P., Farrugia, L. J., Gatti, C., Mallinson, P., Richter, T. & Koritsánszky, T. (2006). XD2006, Revision 5.34. University of New York at Buffalo, NY, USA.
63. Wagner, P. & Kubicki, M. (2007). Acta Cryst. E63, o3083.
64. Wagner, P., Świerczek, K. & Kubicki, M. (2007). Acta Cryst. C63, o445-o447.
65. Wilson, A. J. C. (1992). Editor. International Tables for Crystallography, Vol. C, pp. 219-222. Dordrecht: Kluwer Academic Publishers.
66. Zhurova, E. A. & Pinkerton, A. A. (2001). Acta Cryst. B57, 359-365.
67. Zhurov, V. V., Zhurova, E. A., Stash, A. I. & Pinkerton, A. A. (2011). Acta Cryst. A67, 160-173.