Pointers toward the occurrence of C-F⋯F-C interaction: Experimental charge density analysis of 1-(4-fluorophenyl)-3,6,6-trimethyl-2-phenyl-1,5,6,7- tetrahydro-4H-indol-4-one and l-(4-fluorophenyl)-6-methoxy-2-phenyl-1,2,3,4- tetrahydroisoquinoline

Journal of Physical Chemistry A

Volumn 110, Issue 35, 2006, Pages 10465-10477

  Chopra, Deepak ^a   Cameron, T S ^b   Ferrara, Joseph D ^c   Guru Row, Tayur N ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

^b DALHOUSIE UNIVERSITY   (Canada)

^c Rigaku/MSC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BADER'S THEORY; CHARGE DENSITY; INTERMOLECULAR INTERACTIONS;

CARRIER CONCENTRATION; CRYSTALLINE MATERIALS; ELECTRONIC PROPERTIES; MOLECULAR DYNAMICS; X RAY DIFFRACTION ANALYSIS;

ORGANIC COMPOUNDS;

EID: 33748762987     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0625309     Document Type: Article

References (64)

1. (a) Munshi, P.; Guru Row, T. N. J. Phys. Chem. A 2005, 109, 659-672.
2. (b) Munshi, P.; Guru Row, T. N. CrystEngComm 2005, 7, 608-611.
3. Bader, R. F. W. Atoms in Molecules: A Quantum Theory; Oxford University Press: Oxford, U.K., 1990.
4. Bader, R. F. W. J. Phys. Chem. A 1998, 102, 7314-7323.
5. (a) Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290-296.
6. (b) Aakeroy, C. B.; Sneddon, K. R. Chem. Soc. Rev. 1993, 22, 397-407.
7. (c) Desiraju, G.; Kashino, S.: Coombs, M. M.: Glusker, J. Acta Crystallogr. 1993, B49, 880-892.
8. Steiner, T. Crystallogr. Rev. 2003, 9 (2-3), 177-228.
9. (a) Umezawa, Y.; Tsuboyama, S.; Honda, K.; Uzawa, J.; Nishio, M. Bull. Chem. Soc. Jpn. 1998, 71, 1207-1213.
10. (b) Umezawa, Y.; Tsuboyama, S.; Takahashi, H.; Uzawa, J.; Nishio, M. Tetrahedron 1999, 55, 10047-10056.
11. Nishio, M.; Hirota, M.; Umezawa, Y. The CH/pi Interaction. Evidence, Nature, and Consequences; Wiley-VCH: New York, 1998.
12. Nishio, M. CrystEngComm 2004, 6 (27), 130-158.
13. Mallinson, P. R.; Woz'niak, K.; Wilson, C. C.; McCormac, K. L. Yufit, D. S. J. Am. Chem. Soc. 1999, 121, 4640-4646.
14. Ellena, J.; Goeat, A. E.; Howard, J. A. K.; Punte, G. J. Phys. Chem. A 2001, 105, 8696-8708 and references therein.
15. Oddershede, J.; Larsen, S. J. Phys. Chem. A 2004, 108, 1057-1063.
16. Murray-Rust, P.; Stallings, W. C.; Monti, C. T.; Preston, R. K.; Glusker, J. P. J. Am. Chem. Soc. 1983, 105, 3206-3214.
17. Sarma, J. A. R. P.; Desiraju, G. R. Acc. Chem. Res. 1986, 19, 222-228.
18. Price, S. L.; Stone, A. J.; Rowland, R. S.; Thornley, A. E. J. Am. Chem. Soc. 1994, 116, 4910-4918.
19. Ramasubbu, N.; Parthasarathy, R.; Murray-Rust, P. J. Am. Chem. Soc. 1986, 108, 4308-4314.
20. Desiraju, G.; Parthasarathy, R. J. Am. Chem. Soc. 1989, 111, 8725-8726.
21. Shimoni, L.; Carell, H. L.; Glusker, J. P.; Coombs, M. M. J. Am. Chem. Soc. 1994, 116, 8162-8168.
22. Pauling, L. The Nature of the Chemical Bond, 3rd ed.; Cornell University Press: Ithaca, NY, 1960.
23. Tsirelson, V.; Zou, P. F.; Tang, T.-H.; Bader, R. F. W. Acta Crystallogr., Sect. A 1995, 51, 143-153.
24. (a) Shimoni, L.; Glusker, J. P. Struct. Chem. 1994, 5, 383-397.
25. (b) Howard, J. A. K.; Hoy, V. J.; O'Hagan D.; Smith, G. Tetrahedron 1996, 52, 12613-12622.
26. (c) Duntiz, J. D.; Taylor, R. Chem.-Eur. J. 1997, 3, 89-98.
27. (d) Haufe, G.; Rossen, T. C.; Meyer, O. G. J.; Fröhlich, R., Rissanen, K. J. Fluor. Chem. 2002, 114, 4253-4264.
28. (d) Dunitz, J. D. ChemBioChem 2004, 5, 614-621.
29. Buschmann, J.; Koritsanszky, T.; Kuschel, R.; Luger, P.; Seppelt, K. J. Am. Chem. Soc. 1991, 113, 233-238.
30. Kuboto, M.; Ohba, S. Acta Crystallogr., Sect. B 1992, 48, 849-854.
31. Irngartinger, H.; Shack, S. J. Am. Chem. Soc. 1998, 120, 5818-5819.
32. Mallinson, P. R.; Barr, G.; Coles, S. J.; Guru Row, T. N.; MacNicol, D. D.; Teat, S. J.; Wozniak, K. J. Synchrotron Radiat. 2000, 7, 160-166.
33. Larsen, S.; Flensburg, C.; Bengacted, H. S.; Sorenson, H. O. Acta Crystallogr., AS55, 1999, 38.
34. Buschmann, J.; Koritsanszky, T.; Lentz, D.; Luger, P.; Nickelt, N.; Willemsen, S. Z. Kristallogr. 2000, 215, 487.
35. Bach, A.; Lentz, D.: Luger, P J. Phys. Chem. A 2001, 105, 7405-7412.
36. Bianchi, R.; Forni, A.; Pilati, T. Chem.-Eur. J. 2003, 9, 1631-1638.
37. (a) Choudhury A. R.; Guru Row, T. N. Cryst. Growth Des. 2004, 4, 47-52.
38. (b) Choudhury A. R.; Guru Row, T. N. CrystEngComm 2006, 8, 265-274.
39. Hibbs, D. E.; Overgaard, J.; Platts, J. A.; Waller, M. P.; Hursthouse, M. B. J. Phys. Chem. B 2004, 108, 3663-3672.
40. Coppens, P. Acta Crystallogr. 1998, A54, 779-788.
41. Coppens, P. X-ray Charge Densities and Chemical Bonding; Oxford University Press: Oxford, U.K., 1997.
42. Koritsanszky, T. S.; Coppens, P. Chem. Rev. 2001, 101 (6), 1583-1621.
43. Hansen, N. K., Coppens, P. Acta Crystallogr. 1978, A34, 909-921.
44. Koch, U.; Popelier, P. L A. J. Phys. Chem. 1995, 99, 9747-9754.
45. Popelier, P. Atoms in Molecules. An Introduction; Prentice Hall: Harlow, U.K., 2000; pp 150-153.
46. Abramov, Yu. A. Acta Crystallogr. 1997, A53, 264-272.
47. Espinosa, E.; Molins, E.; Lecomte, C. Chem. Phys. Lett. 1998, 85, 170-173.
48. (a) Bondi, A. J. Phys. Chem. 1964, 68, 441-451.
49. (b) Nyburg, S. C.; Faerman, C. H. Acta Crystallogr. 1985, B41, 274-279.
50. Nagarajan, K.; Tawalker, P. K.; Shah, R. K., Mehta, S. R.; Nayak, G. V. Ind. J. Chem. 1985, 24b, 98-111.
51. Chopra, D.; Guru Row, T. N. J. Mol. Struct. 2005, 733, 133-141.
52. Chopra, D.; Nagarajan K.; Guru Row, T. N. Cryst. Growth Des. 2005, 5, 1035-1039.
53. Otwinowski, Z.; Minor, W. Processing of X-ray Diffraction Data Collected in Oscillation Mode. In Macromolecular Crystallography. Part A; Carter, C. W., Jr., Sweet, R. M., Eds.; Methods in Enzymology, Vol. 276; Academic Press: San Diego, CA, 1997; pp 307-326.
54. Blessing, R. H. Crystallogr. Rev. 1987, 1, 3-58.
55. Sheldrick, G. M. SHELXS97 and SHELXL97; University of Göttingen: Göttingen, Germany, 1997.
56. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837-838 (WinGX, version 1.64.05).
57. Farragia, L. J. J. Appl. Crystallogr. 1997, 30, 565 (ORTEP-3).
58. 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, A computer program package for multipole refinement and analysis of electron densities from diffraction data, version 4.10, July; Free University of Berlin, Germany; University of Wales, Cardiff, U.K.; Università di Milano, U.K.; CNR-ISTM, Milano, U.K.; University of Glasgow, U.K.; State University of New York, Buffalo, NY; University of Nancy, France, 2003.
59. Clementi, E.; Roetti, C. At. Data Nucl. Data Tables 1974, 14, 177.
60. Allen, F. H.; Acta Crystallogr. 1986, B42, 515-522.
61. Hirshfeld, F. L. Acta Crystallogr. 1976, A32, 239-244.
62. Matta, C. F. In Hydrogen Bonding-New Insight; Grabowski, S., Ed.; Challenges and Advances in Computational Chemistry and Physics Series; Kluwer: New York, 2006.
63. Matta, C. F.; Hernandez-Trujillo, J.; Tang, T. H.; Bader, R. F. W. Chem.-Eur. J. 2003, 9, 1940-1951.
64. Matta, C. F.; Castillo, N.; Boyd, R. J. J. Phys. Chem. A 2005, 109, 3669-3681.