Analysis of weak interactions involving organic fluorine: Insights from packing features in substituted 4-keto-tetrahydroindoles

Journal of Molecular Structure

Volumn 888, Issue 1-3, 2008, Pages 70-83

  Chopra, Deepak ^a   Nagarajan, K ^b   Guru Row, T N ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

^b Hikal Ltd   (India)

Author keywords

Hydrogen bonds; Molecular conformation; Organic fluorine; Weak interactions

Indexed keywords

ARSENIC COMPOUNDS; FLOW INTERACTIONS; FLUORINE; HYDROGEN; KETONES; NONMETALS; ORGANIC POLYMERS; POWDERS;

ADDITIONAL STABILITY; CONFORMATIONAL CHANGES; HYDROGEN BONDS; HYDROGEN-BONDED NETWORKS; INTER-MOLECULAR INTERACTIONS; MOLECULAR CONFORMATION; ORGANIC FLUORINE; PACKING MOTIFS; PHENYL RINGS; SINGLE BONDS; WEAK INTERACTIONS;

CHLORINE COMPOUNDS;

EID: 52049089173     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2007.11.040     Document Type: Article

References (52)

1. Desiraju G.R., and Steiner T. The Weak Hydrogen Bond in Structural Chemistry and Biology (1999), Oxford University Press, Oxford
2. Bohm H.J., and Klebe G. Angewandte Chemie, Intl. Ed. Eng. 35 (1996) 2588
3. D.B. Boyd, Computer Aided Molecular Design, in: Encyclopedia of Computer Science and Technology, vol. 33, Suppl.18, New York, 1995, pp. 41-71.
4. Engh R.A., Brandstetter H., Sucher G., Eichinger A., Baumann I., and Bode W. Structure 4 (1996) 1353
5. Jeffrey G.A. An Introduction to Hydrogen Bonding (1997), Oxford University Press Inc, New York
6. Desiraju G.R. Acc. Chem. Res. 67 (2002) 565
7. Guru Row T.N. Coord. Chem. Rev. 183 (1999) 81
8. Desiraju G.R. Curr. Opin. Solid State Mater. Sci. 2 (1997) 451
9. Aakeroy C.B. Acta Crystallogr. B 53 (1997) 569
10. Subramanian S., and Zaworotko M.J. Coord. Chem. Rev. 137 (1994) 357
11. Umezawa Y., Tsuboyama S., Honda K., Uzawa J., and Nishio M. Bull. Chem. Soc. Jpn. 71 (1998) 207
12. Nishio M., Umezawa Y., Hirota M., and Takeuchi Y. Tetrahedron 51 (1995) 8665
13. Desiraju G.R., and Gavezzotti A. J. Chem. Soc. Chem. Commun. 621 (1989)
14. Bohm H.J., Banner D., Bendels S., Kansy M., Kuhn B., Muller K., Sander U.O., and Stahl M. ChemBioChem 5 (2004) 637
15. Jeschke P. ChemBioChem 5 (2004) 570
16. Leroux F. ChemBioChem 5 (2004) 644
17. Shimoni L., and Glusker J.P. Struct. Chem. 5 (1994) 383
18. Howard J.A.K., Hoy V.J., O'Hagan D., and Smith G.T. Tetrahedron 52 (1996) 12613
19. Dunitz J.D., and Taylor R. Chem. Eur. J. 3 (1997) 89
20. Desiraju G.R., and Partasarathy R. J. Am. Chem. Soc. 111 (1989) 8725
21. Choudhury A.R., Urs U.K., Guru Row T.N., and Nagarajan K. J. Mol. Struct. 605 (2002) 71
22. Prasanna M.D., and Guru Row T.N. Cryst. Eng. 3 (2000) 135
23. Prasanna M.D., and Guru Row T.N. J. Mol. Struct. 562 (2001) 55
24. Prasanna M.D., and Guru Row T.N. J. Mol. Struct. 559 (2001) 255
25. Chopra D., Nagarajan K., and Guru Row T.N. Cryst. Growth Des. 5 (2005) 1035
26. Reichenbacher K., Suss H.I., and Hulliger J. Chem. Soc. Rev. 34 (2005) 22
27. Chopra D., and Guru Row T.N. CrystEngComm 10 (2008) 54
28. Choudhury A.R., and Guru Row T.N. Cryst. Growth Des. 4 (2004) 47
29. Haufe G., Rosen T.C., Meyer O.G.J., Frohlich R., and Rissanen K. J. Fluor. Chem. 114 (2002) 189
30. Frohlich R., Rosen T.C., Meyer O.G.J., Rissanen K., and Haufe G. J. Mol. Struct. 787 (2006) 50
31. Hyla-Krypsin I., Haufe G., and Grimme S. Chem. Eur. J. 10 (2004) 3411 and references therein
32. Chopra D., and Guru Row T.N. Cryst. Growth Des. 5 (2005) 1679
33. Chopra D., and Guru Row T.N. Cryst. Growth Des. 6 (2006) 1267
34. Chopra D., and Guru Row T.N. J. Mol. Sruct. 733 (2005) 133
35. Chopra D., Thiruvenkatam V., and Guru Row T.N. Cryst. Growth Des. 6 (2006) 843
36. Chopra D., Thiruvenkatam V., Manjunath S.G., and Guru Row T.N. Cryst. Growth Des. 7 (2007) 868
37. Chopra D., Cameron T.S., Ferrera J.D., and Guru Row T.N. J. Phys. Chem. A 110 (2006) 10465
38. M Josien L., and Sourisseau G. In: Hadzi D. (Ed). Hydrogen Bonding (1959), Pergamon Press, London
39. Nishio M. CrystEngComm 6 (2004) 130
40. Nishio M., Hirota M., and Umezawa Y. The CH/π Interaction. Evidence, Nature and Consequences (1998), Wiley-VCH, New York
41. Nagarajan K., Tawalker P.K., Shah R.K., Mehta S.R., and Nayak G.V. Indian J. Chem. 24B (1985) 98
42. Nagarajan K., Tawalker P.K., Kulkarni C.L., Venkateswarlu A., Prabhu S.S., and Nayak G.V. Indian J. Chem. 23B (1984) 1243
43. Bruker (1998). SMART, SAINT, SADABS, XPREP, SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.
44. Altomare A., Cascarano G., and Giacovazzo C. A program for crystal structure solution. J. Appl. Crystallogr. 26 (1993) 343
45. G.M. Sheldrick, SHELXL97, Program for Crystal Structure Refinement, University of Gottingen, Germany, 1997.
46. Farrugia L.J. WINGX J. Appl. Cryst 32 (1999) 837
47. Farrugia L.J. J. Appl. Cryst. 30 (1997) 565
48. D.M. Watkin, L. Pearce, C.K. Prout, CAMERON - A Molecular Graphics Package, Chemical Crystallography Laboratory, University Of Oxford, Oxford, 1993.
49. Nardelli M. J. Appl. Cryst. 28 (1995) 569
50. Spek A.L. Acta Crystallogr. A 46 (1990) C34
51. Gaussian 98, Revision A.11.3, M.J. Frisch, G.W. Trucks, H.B.Schlegel, G.E. Scuseria, M.A.Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A Montgomery, Jr. R.E.Stratmann, J.C.Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C.Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, N. Rega, P. Salvador, J.J. Dannenberg, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, J.A. Pople, Gaussian, Inc., Pittsburgh PA, 2002.
52. Bernstein J., Davis R.E., Shimoni L., and Chang N.L. Angew. Chem. Int. Engl. 34 (1995) 1555