Crystallography Reports

, Volume 52, Issue 2, pp 243–252 | Cite as

Molecular and crystal structures of some novel derivatives of 3-aryl-7-arylidene-3,3a,4,5,6,7-hexahydroindazoles

  • V. V. Abakumov
  • S. V. Shishkina
  • R. I. Zubatyuk
  • I. M. Gella
  • N. S. Pivnenko
  • L. A. Kutulya
  • O. V. Shishkin
Structure of Organic Compounds
  • 27 Downloads

Abstract

The stereochemical aspects of the interaction of 2,6-bis(arylidene)-cyclohexanone and 2,6-bis(arylidene)-3-methylcyclohexanone with arylhydrazine (aryl is phenyl or 4-nitrophenyl) and methylhydrazine are investigated using X-ray diffraction analysis. The molecular structure of the 3-aryl-7-arylidene-3,3a,4,5,6,7-hexahydroindazoles synthesized is determined by X-ray diffraction analysis for the first time. It is established that the stereochemistry of the products of the interaction between the cyclohexanone derivatives and arylhydrazines depends on the electronic nature of the substituent in the aryl group. Two regioisomeric products with different positions of the methyl group in the cyclohexane ring with respect to the arylidene fragment are synthesized by the reaction of 2,6-bis(4-methoxybenzylidene)-3-methylcyclohexanone with methylhydrazine. The influence of the substituents at the nitrogen atom of the pyrazoline ring on the intramolecular electronic interactions and the geometry of the heterocycle in the compounds under investigation is discussed.

PACS numbers

61.10.Nz 61.66.Hq 

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References

  1. 1.
    J. Krapcho and C. F. Turk, J. Med. Chem. 22, 207 (1979).CrossRefGoogle Scholar
  2. 2.
    M. S. Puar, G. C. Rovnyak, A. I. Cohen, and B. Toeplitz, J. Org. Chem. 44, 2513 (1979).CrossRefGoogle Scholar
  3. 3.
    A. A. Khalaf, A. K. El-Shafei, and A. M. El-Sayed, J. Heterocycl. Chem. 19, 609 (1982).CrossRefGoogle Scholar
  4. 4.
    T. Lorand, D. Szabo, A. Foldesi, et al., J. Chem. Soc., Perkin Trans. 1, 481 (1985).CrossRefGoogle Scholar
  5. 5.
    Amadu Razak Yaya, Candidate’s Dissertation in Chemistry (Kharkov National University, Kharkov, Ukraine, 2003) [in Russian].Google Scholar
  6. 6.
    M. Karplus, J. Chem. Phys. 30, 11 (1969).CrossRefMathSciNetADSGoogle Scholar
  7. 7.
    I. M. Gella, Amadu Razak Yaya, G. V. Cherkaev, et al., Khim. Geterotsikl. Soedin., No. 12, 1650 (1997).Google Scholar
  8. 8.
    V. G. Mitina, L. A. Kutulya, and A. A. Sukhorukov, Problems of Physical Chemistry: Structure, Spectral, Luminescence, and Photochemical Properties of Unsaturated Ketones and 2-Pyrazolines (Kharkov University, Kharkov, 1989) [in Russian].Google Scholar
  9. 9.
    A. I. Krivoshey, L. A. Kutulya, V. V. Vashchenko, et al., Proceedings of the Ninth International Conference on Nonlinear Optics of Liquid and Photorefractive Crystals, Crimea, Ukraine, 2002 (Proc. SPIE-Int. Soc. Opt. Eng. 5257, 2002), p. 13.Google Scholar
  10. 10.
    A. I. Krivoshey, Candidate’s Dissertation in Chemistry (Institute for Single Crystals, National Academy of Sciences of Ukraine, Kharkov, Ukraine, 2004) [in Russian].Google Scholar
  11. 11.
    G. M. Sheldrick, SHELXT PLUS, PC Version, Version 4.2: A System of Computer Programs for the Determination of Crystal Structures from X-ray Diffraction Data (University of Göttingen, Göttingen, Germany, 1992).Google Scholar
  12. 12.
    N. S. Zefirov, V. A. Palyulin, and E. E. Dashevskaya, J. Phys. Org. Chem. 3, 147 (1990).CrossRefGoogle Scholar
  13. 13.
    B. Duffin, Acta Crystallogr. 15(3), 214 (1962).CrossRefGoogle Scholar
  14. 14.
    L. A. Kutulya, A. S. Tolochko, V. I. Kulishov, and G. P. Semenkova, Abstracts of Papers of the International Conference on Chemistry of Nitrogen Containing Heterocycles “CNH-2003,” Kharkov, Ukraine, 2003 (Kharkov, 2003), p. 179.Google Scholar
  15. 15.
    C. J. Fahri, L. Yang, and D. van der Veer, J. Am. Chem. Soc. 125(13), 3799 (2003).CrossRefGoogle Scholar
  16. 16.
    Z. Jia, J. W. Quail, and J. R. Dimmock, Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 46, 2467 (1990).CrossRefGoogle Scholar
  17. 17.
    L. A. Kutulya, V. V. Vashchenko, V. P. Kuznetsov, et al., Kristallografiya 40(6), 1015 (1995) [Crystallogr. Rep. 40 (6), 941 (1995)].Google Scholar
  18. 18.
    L. A. Kutulya, V. P. Kuznetsov, L. D. Patsenker, et al., Kristallografiya 39(5), 860 (1994) [Crystallogr. Rep. 39 (5), 782 (1994)].Google Scholar
  19. 19.
    V. P. Kuznetsov, V. I. Kulishov, L. A. Kutulya, et al., Kristallografiya 44(2), 229 (1999) [Crystallogr. Rep. 44 (2), 196 (1999)].ADSGoogle Scholar
  20. 20.
    L. A. Kutulya, V. P. Kuznetsov, V. I. Kulishov, and V. V. Vashchenko, Kristallografiya 44(3), 475 (1999) [Crystallogr. Rep. 44 (3), 435 (1999)].ADSGoogle Scholar
  21. 21.
    Yu. V. Zefirov, Kristallografiya 42(5), 936 (1997) [Crystallogr. Rep. 42 (5), 865 (1999)].MathSciNetGoogle Scholar

Copyright information

© Pleiades Publishing, Inc. 2007

Authors and Affiliations

  • V. V. Abakumov
    • 1
  • S. V. Shishkina
    • 1
  • R. I. Zubatyuk
    • 1
  • I. M. Gella
    • 1
  • N. S. Pivnenko
    • 1
  • L. A. Kutulya
    • 1
  • O. V. Shishkin
    • 1
  1. 1.Scientific and Technological Corporation “Institute for Single Crystals”National Academy of Sciences of UkraineKharkovUkraine

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