Structural analysis and multipole modelling of quercetin monohydrate - A quantitative and comparative study

Acta Crystallographica Section B: Structural Science

Volumn 67, Issue 1, 2011, Pages 63-78

  Domagała, Sawomir ^a   Munshi, Parthapratim ^a   Ahmed, Maqsood ^a   Guillot, Benot ^a   Jelsch, Christian ^a  

^a Nancy University CNRS   (France)

Author keywords

database; electron density; flavonoid; theoretical calculations; X ray diffraction

Indexed keywords

A PLANTS; ATOMIC DISPLACEMENT PARAMETERS; ATOMIC POSITIONS; COMPARATIVE STUDIES; DATABASE; DATABASE TRANSFER; DIFFRACTION DATA; ELECTRON DENSITIES; ELECTRON DENSITY; ELECTROSTATIC INTERACTION ENERGY; EXPERIMENTAL DATABASE; FIGURES OF MERITS; FLAVONOIDS; HIGH RESOLUTION; MODEL APPROACH; MULTIPOLES; QUANTUM-MECHANICAL CALCULATION; RESIDUAL ELECTRON DENSITIES; THEORETICAL CALCULATIONS; TOPOLOGICAL ANALYSIS;

ATOMS; CARRIER CONCENTRATION; DATABASE SYSTEMS; DENSITY FUNCTIONAL THEORY; DIFFRACTION; ELECTRON DENSITY MEASUREMENT; ELECTRONS; FATTY ACIDS; ISOMERS; PHENOLS; QUANTUM THEORY; STRUCTURAL ANALYSIS; TOPOLOGY; X RAY DIFFRACTION; X RAYS;

CRYSTAL ATOMIC STRUCTURE;

QUERCETIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; QUERCETIN; X-RAY DIFFRACTION;

EID: 79251489104     PISSN: 01087681     EISSN: 01087681     Source Type: Journal    
DOI: 10.1107/S0108768110041996     Document Type: Article

References (89)

1. Abramov, Yu. A. (1997). Acta Cryst. A53, 264-272.
2. Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-S19.
3. Allen, F. H., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (2006). International Tables for Crystallography, Vol. C, ch. 9.5, pp. 790-811. Berlin: Springer.
4. Bader, R. F. W. (1990). Atoms in Molecules: A Quantum Theory, Oxford University Press.
5. Bader, R. F. W. (1998). J. Phys. Chem. A, 102, 7314-7323.
6. Bak, J. M., Domagała, S., Hübschle, C., Jelsch, C., Dittrich, B. & Dominiak, P. M. (2011). Acta Cryst. A67. In the press.
7. Bak, J. M., Dominiak, P. M.,Wilson, C. C. & Woźniak, K. (2009). Acta Cryst. A65, 490-500.
8. Becke, A. D. (1988). J. Chem. Phys. 88, 2547-2553.
9. Becke, A. D. (1993). J. Chem. Phys. 98, 5648-5652.
10. Brock, C. P., Dunitz, J. D. & Hirshfeld, F. L. (1991). Acta Cryst. B47, 789-797.
11. Coppens, P. (1997). X-ray Charge Densities and Chemical Bonding. New York: Oxford University Press.
12. Cruickshank, D. W. J. (1956). Acta Cryst. 9, 747-753.
13. DeLano, W. L. (2002). The PyMOL Molecular Graphics System, http://www.pymol.org.
14. Destro, R., Soave, R., Barzaghi, M. & Presti, L. L. (2005). Chem. Eur. J. 11, 4621-4634.
15. Dittrich, B., Hübschle, C. B., Holstein, J. J. & Fabbiani, F. P. A. (2009). J. Appl. Cryst. 42, 1110-1121.
16. Dittrich, B., Hübschle, C. B., Luger, P. & Spackman, M. A. (2006). Acta Cryst. D62, 1325-1335.
17. Dittrich, B., Hübschle, C. B., Messerschmidt, M., Kalinowski, R., Girnt, D. & Luger, P. (2005). Acta Cryst. A61, 314-320.
18. Dittrich, B., Koritsánszky, T. & Luger, P. (2004). Angew. Chem. Int. Ed. 43, 2718-2721.
19. Dittrich, B., McKinnon, J. J. & Warren, J. E. (2008). Acta Cryst. B64, 750-759.
20. Dittrich, B., Munshi, P. & Spackman, M. A. (2007). Acta Cryst. B63, 505-509.
21. Dittrich, B., Strumpel, M., Schä fer, M., Spackman, M. A. & Koritsánszky, T. (2006). Acta Cryst. A62, 217-223.
22. Dittrich, B., Weber, M., Kalinowski, R., Grabowsky, S., Hübschle, C. B. & Luger, P. (2009). Acta Cryst. B65, 749-756.
23. Domagała, S. & Jelsch, C. (2008). J. Appl. Cryst. 41, 1140-1149.
24. Dominiak, P. M., Makal, A., Mallinson, P. R., Trzciń ska, K., Eilmes, J., Grech, E., Chruszcz, M., Minor, W. & Woźniak, K. (2006). Chem. Eur. J. 12, 1941-1949.
25. Dominiak, P. M., Volkov, A., Dominiak, A. P., Jarzembska, K. N. & Coppens, P. (2009). Acta Cryst. D65, 485-499.
26. Dominiak, P. M., Volkov, A., Li, X., Messerschmidt, M. & Coppens, P. (2007). J. Chem. Theory Comput. 3, 232-247.
27. Dovesi, R., Saunders, V. R., Roetti, C., Orlandol, R., Zicovich-Wilson, C. M., Pascale, F., Civalleri, B., Doll, K., Harrison, N. M., Bush, I. J., D'Arco, Ph. & Llunell, M. (2008). CRYSTAL06 1.0, Version 1-0-2. University of Turin, Italy.
28. ElAttar, T. M. A. & Virji, A. S. (1999). Anticancer Drugs, 10, 187-194.
29. Espinosa, E., Alkorta, I., Elguero, J. & Molins, E. (2002). J. Chem. Phys. 117, 5529-5542.
30. Faerman, C. H. & Price, S. L. (1990). J. Am. Chem. Soc. 112, 4915-4926.
31. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
32. Farrugia, L. J., Kočovský, P., Senn, H. M. & Vyskočil, S ̌ . (2009). Acta Cryst. B65, 757-769.
33. Formica, J. V. & Regelson, W. (1995). Food Chem. Toxicol. 33, 1061-1080.
34. Fournier, B., Bendeif, E.-E., Guillot, B., Podjarny, A., Lecomte, C. & Jelsch, C. (2009). J. Am. Chem. Soc. 131, 10929-10941.
35. Gatto, M. T., Falcocchio, S., Grippa, E., Mazzanti, G., Battinelli, L., Nicolosi, G., Lambusta, D. & Saso, L. (2002). Bioorg. Med. Chem. 10, 269-272.
36. Gryglewski, R. J., Korbut, R., Robak, J. & Swies, J. (1987). Biochem. Pharmacol. 36, 317-322.
37. Guillot, B., Viry, L., Guillot, R., Lecomte, C. & Jelsch, C. (2001). J. Appl. Cryst. 34, 214-223.
38. Hansen, N. K. & Coppens, P. (1978). Acta Cryst. A34, 909-921.
39. Hariharan, P. C. & Pople, J. A. (1973). Theor. Chim. Acta, 28, 213-222.
40. Hirshfeld, F. L. (1971). Acta Cryst. B27, 769-781.
41. Hirshfeld, F. L. (1976). Acta Cryst. A32, 239-244.
42. Hohenberg, P. & Kohn, W. (1964). Phys. Rev. B, 136, 864-871.
43. Hummel, W., Hauser, J. & Bürgi, H. B. (1990). J. Mol. Graphics, 8, 214-218.
44. Jelsch, C., Guillot, B., Lagoutte, A. & Lecomte, C. (2005). J. Appl. Cryst. 38, 38-54.
45. Jelsch, C., Pichon-Pesme, V., Lecomte, C. & Aubry, A. (1998). Acta Cryst. D54, 1306-1318.
46. Jin, G.-Z., Yamagata, Y. & Tomita, K. (1990). Acta Cryst. C46, 310-313.
47. Johnson, C. K. & Burnett, M. N. (1996). ORTEPIII. Report ORNL- 6895. Oak Ridge National Laboratory, Tennessee, USA.
48. Koch, U. & Popelier, P. L. A. (1995). J. Phys. Chem. 99, 9747-9754.
49. Koritsánszky, T. & Coppens, P. (2001). Chem. Rev. 101, 1583-1628.
50. Lamson, D. W. & Brignall, M. S. (2000). Altern. Med. Rev. 5, 196-208.
51. Le Page, Y. & Gabe, E. J. (1979). J. Appl. Cryst. 12, 464-466.
52. Lebedev, V. I. & Laikov, D. N. (1999). Dokl. Math. 59, 477-481.
53. Lee, C., Yang, W. & Parr, R. G. (1988). Phys. Rev. B, 37, 785-789.
54. Leopoldini, M., Marino, T., Russo, N. & Toscano, M. (2004). Theor. Chem. Acc. 111, 210-216.
55. Mallinson, P. R., Smith, G. T., Wilson, C. C., Grech, E. & Woźniak, K. (2003). J. Am. Chem. Soc. 125, 4259-4270.
56. Mata, I., Alkorta, I., Molins, E. & Espinosa, E. (2010). Chem. Eur. J. 16, 2442-2452.
57. McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). Chem. Commun. pp. 3814-3816.
58. McKinnon, J. J., Spackman, M. A. & Mitchell, A. S. (2004). Acta Cryst. B60, 627-668.
59. Munshi, P. & Guru Row, T. N. (2005a). Crystallogr. Rev. 11, 199-241.
60. Munshi, P. & Guru Row, T. N. (2005b). CrystEngComm, 7, 608-611.
61. Munshi, P., Jelsch, C., Hathwar, V. R. & Guru Row, T. N. (2010). Cryst. Growth Des. 10, 1516-1526.
62. Munshi, P., Madsen, A. ø., Spackman, M. A., Larsen, S. & Destro, R. (2008). Acta Cryst. A64, 465-475.
63. Munshi, P., Skelton, W., McKinnon, J. J. & Spackman, M. A. (2008). CrystEngComm, 10, 197-206.
64. Murray, J. S., Peralta-Inga, Z. & Politzer, P. (2000). Int. J. Quantum Chem. 80, 1216-1223.
65. Murray, J. S. & Politzer, P. (1998). J. Mol. Struct. Theochem, 425, 107-114.
66. Nöthlings, U., Murphy, S. P., Wilkens, L. R., Henderson, B. E. & Kolonel, L. N. (2007). Am. J. Epidemiol. 166, 924-931.
67. Olejniczak, S. & Potrzebowski, M. (2004). J. Org. Biomol. Chem. 2, 2315-2322.
68. Overgaard, J., Schiøtt, B., Larsen, F. K. & Iversen, B. B. (2001). Chem. Eur. J. 7, 3756-3767.
69. Oxford Diffraction (2009). CrysAlisPro. Oxford Diffraction Ltd, Yarnton, England.
70. Pichon-Pesme, V., Jelsch, C., Guillot, B. & Lecomte, C. (2004). Acta Cryst. A60, 204-208.
71. Pichon-Pesme, V., Lecomte, C. & Lachekar, H. (1995). J. Phys. Chem. 99, 6242-6250.
72. Popelier, P. (2000). Atoms in Molecules. An Introduction. Harlow: Prentice Hall.
73. Rossi, M., Rickles, L. F. & Halpin, W. A. (1986). Bioorg. Chem. 14, 55-69.
74. Roversi, P. & Destro, R. (2004). Chem. Phys. Lett. 386, 472-478.
75. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
76. Shoskes, D. A., Zeitlin, S. I., Shahed, A. & Rajfer, J. (1999). Urology, 54, 960-963.
77. Spackman, M. A. (1992). Chem. Rev. 92, 1769-1797.
78. Spackman, M. A. (1997). Annu. Rep. Prog. Chem. Sect. C Phys. Chem. 94, 177-207.
79. Spackman, M. A. & Jayatilaka, D. (2009). CrystEngComm, 11, 19-32.
80. Spackman, M. A. & McKinnon, J. J. (2002). CrystEngComm, 4, 378-392.
81. Spackman, M. A., Munshi, P. & Dittrich, B. (2007). ChemPhysChem, 8, 2051-2063.
82. Treutler, O. & Ahlrichs, R. (1995). J. Chem. Phys. 102, 346-354.
83. Tsirelson, V. G. & Ozerov, R. P. (1996). Electron Density and Bonding in Crystals. Bristol: Institute of Physics Publishing.
84. Volkov, A., Li, X., Koritsánszky, T. S. & Coppens, P. (2004). J. Phys. Chem. A, 108, 4283-4300.
85. Volkov, A., Messerschmidt, M. & Coppens, P. (2007). Acta Cryst. D63, 160-170.
86. Whitten, A. E. & Spackman, M. A. (2006). Acta Cryst. B62, 875-888.
87. Williams, T. et al. (2009). gnuplot4.2, http://www.gnuplot.info/.
88. Wolff, S. K., Grimwood, D. J., McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). CrystalExplorer2.0. University ofWestern Australia, Perth, http://hirshfeldsurface.net/.
89. Zarychta, B., Pichon-Pesme, V., Guillot, B., Lecomte, C. & Jelsch, C. (2007). Acta Cryst. A63, 108-125.