Influence of O-H⋯O=P hydrogen bonding on the supramolecular architectures of phosphorus-based hydrazones: Alternate right- and left-handed fused helical chains based on O-H⋯O=P hydrogen bonds in the crystal structure of C6H5P(O)[N(CH3)N=CHC 6H4-p-OH]2

Crystal Growth and Design

Volumn 6, Issue 4, 2006, Pages 910-914

  Chandrasekhar, Vadapalli ^a   Azhakar, Ramachandran ^a   Bickley, Jamie F ^b   Steiner, Alexander ^b  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

^b UNIVERSITY OF LIVERPOOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33646360199     PISSN: 15287483     EISSN: None     Source Type: Journal    
DOI: 10.1021/cg050426v     Document Type: Article

References (52)

1. (a) Schmidt, E. W. Hydrazine and its Derivatives: Preparation, Properties, Applications, 2nd ed.; Wiley-Interscience: New York, 2001; Vols. 1 and 2.
2. (b) Hydrazine and its derivatives, in Kirk-Othmer Encyclopedia of Chemical Technology, 4th ed.; Wiley & Sons: New York, 1995; Vol. 13.
3. (a) Katritzky, A. R.; Pozharskii, A. F. Handbook of Heterocyclic Chemistry, 2nd ed.; Pergamon: Oxford, 2000, p 591.
4. (b) Paquette, L. A. Encyclopedia of Reagents for Organic Synthesis; Wiley: Chichester, 1995.
5. (a) Hsu, H.-F.; Chu, W.-C.; Hung, C.-H.; Liao, J.-H. Inorg. Chem. 2003, 42, 7369.
6. (b) Rath, S. P.; Olmstead, M. M.; Balch, A. L. Inorg. Chem. 2004, 43, 6357.
7. (c) Mitzi, D. B. Inorg. Chem. 2005, 44, 3755.
8. (d) Fischer, G.; Herler, S.; Mayer, P., Schulz, A.; Villinger, A.; Weigand, J. J. Inorg. Chem. 2005, 44, 1740.
9. (e) Chandrasekhar, V.; Azhakar, R.; Bickley, J.; Steiner, A. Chem. Commun. 2005, 459.
10. (f) Chandrasekhar, V.; Azhakar, R.; Zacchini, S.; Bickley, J.; Steiner, A. Inorg. Chem. 2005, 44, 4608.
11. (g) Chandrasekhar, V.; Azhakar, R.; Andavan, G. T. S.; Krishnan, V.; Zacchini, S.; Bickley, J.; Steiner, A.; Butcher, R. J.; Kögerler, P. Inorg. Chem. 2003, 42, 5989.
12. (h) Sreerama, S. G.; Pal, S. Inorg. Chem. 2005, 44, 6299.
13. (a) Katti, K. V.; Reddy, V. S.; Singh, P. R. Chem. Soc. Rev. 1995, 24, 97
14. (b) Wang, M.; Volkert, E. W.; Singh, P. R.; Katti, K. K.; Lusiak, P.; Katti, K. V.; Barnes, C. L. Inorg. Chem. 1994, 33, 1184.
15. (c) Reddy, V. S.; Katti, K. V.; Barnes C. L. Organometallics 1994, 13, 2391.
16. (d) Singh P. R.; Jimenez, H.; Katti, K. V.; Volkert, W. A.; Barnes, C. L. Inorg. Chem. 1994, 33, 736.
17. (e) Katti, K. V.; Ge, Y. W.; Singh, P. R.; Date, S. V.; Barnes, C. L. Organometallics 1994, 13, 541.
18. (f). Katti, K. V.; Singh, P. R.; Barnes, C. L. Inorg. Chem. 1992, 31, 4588.
19. (a) Chandrasekhar, V.; Krishnan, V.; Steiner, A.; Bickley, J. F. Inorg. Chem. 2004, 43, 166.
20. (b) Chandrasekhar, V.; Krishnan, V.; Azhakar, R.; Madhavaiah, C.; Verma, S. J. Chem. Sci. 2005, 43, 175.
21. (c) Albertin, G.; Antoniutti, S.; Bortoluzzi, M.; Castro-Fojo, J.; Garcia-Fonton, S. Inorg. Chem. 2004, 43, 4511.
22. (a) Chandrasekhar, V.; Azhakar, R. CtystEngComm 2005, 7, 346.
23. (b) Chandrasekhar, V.; Krishnan, V.; Andavan, G. T. S.; Steiner, A.; Zacchini, S. CrystEngComm 2003, 5, 245.
24. (c) Majoral, J. P.; Kraemer, R.; Navech, J.; Matins, F. Tetrahedron 1976, 32, 2633.
25. Chandrasekhar, V.; Andavan, G. T. S.; Nagendran, S.; Krishnan, V.; Azhakar, R.; Butcher, R. J. Organometallics 2003, 22, 976.
26. (a) Forristal, I.; Lowman, J.; Afarinkia, K.; Steed, J. W. CrystEngComm 2001, 54.
27. (b) Mehring, M.; Schürmann, M.; Ludwig, R. Chem. Eur. J. 2003, 9, 838.
28. (c) Mehring, M. Eur. J. Inorg. Chem. 2004, 3240.
29. (d) Henn, M.; Jurkschat, K.; Mansfeld, D.; Mehring, M.; Schürmann, M. J. Mol. Struct. 2004, 697, 213.
30. (e) Kumara Swamy, K. C.; Kumaraswamy, S.; Kommana, P. J. Am. Chem. Soc. 2001, 123, 12642.
31. (f) Frantz, R.; Durand, J.; Carré, F.; Lanneau, G. F.; Bideau, J. L.; Alonso, B.; Massiot, D. Chem. Eur. J. 2003, 9, 770.
32. (g) Plazuk, D.; Rybarczyk-Pirek, A.; Zakrzewski, J. J. Organomet. Chem. 2004, 689, 1165.
33. (h) Santos, J. S. O.; Montouilliout, V.; Fayon, F.; Delain-Bioton, L.; Villemin, D.; Jaffrès, P. New. J. Chem. 2004, 28, 1244.
34. (i) Kong, D.; Clearfield, A.; Zon, J. Cryst. Growth Des. 2005, 5, 1767.
35. (a) Desiraju, G. R.; Steiner, T. The Weak Hydrogen Bond in Structural Chemistry and Biology; Oxford University Press: Oxford, 1999.
36. (b) Steiner, T. Angew. Chem., Int. Ed. 2002, 41, 48.
37. Vogel, A. I. Vogel's Textbook of Practical Organic Chemistry, 5th ed.; Longman: London, 1989.
38. Sheldrick, G. M. SHELXL-97, Program for crystal structure analysis (release 97-2); University of Göttingen, Germany, 1998.
39. Sheldrick, G. M. SHELXTL v. 6.14; Bruker AXS Inc., Madison, WI, 2003.
40. (a) Wang, H. K. Acta Chem. Scand. 1965, 19, 879.
41. (b) Bottle, S. E.; Bott, R. C; Smith, G.; Wermuth, U. D.; Kernard, C. H. L. Acta Crystallogr. 1995, C51, 2633.
42. Muthu, S.; Vittal, J. J. Cryst. Growth Des. 2004, 4, 1181.
43. (a) Nishio, M.; Hiroto, M.; Umezawa, Y. The CH/π Interaction (Evidence, Nature and Consequences); Wiley-VCH: New York, 1998.
44. (b) Nishio, M. CrystEngComm 2004, 6, 130.
45. (c) Venkatramanan, B.; Saifudin, M.-A.; Vittal, J. J.; Valiyavettil, S. CrystEngComm 2004, 6, 284.
46. (d) Mehta, G.; Sen, S.; Ramesh, S. S. CrystEngComm 2005, 7, 563.
47. (e) Pickering, A. L.; Seeber, G.; Long, D.-L.; Cronin, L. 2005, 7, 504.
48. (f) Munshi, P.; Venugopala, K. N.; Jayashree, B. S.; Row: T. N. G. Cryst. Growth Des. 2004, 4, 1105.
49. (a) Desiraju, G. R. Acc. Chem. Res. 2002, 55, 565.
50. (b) Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2311.
51. (c) Basavoju, S.; Aitipamula, S.; Desiraju, G. R. CrystEngComm 2004, 6, 120.
52. (d) Venkatramanan, B.; Ning, Z.; Vittal, J. J.; Valiyavettil, S. CrystEngComm 2005, 7, 108.