Chemistry of Heterocyclic Compounds

, Volume 43, Issue 11, pp 1374–1378 | Cite as

Molecular and crystal structure of 4,6,6-trimethyl-2-oxo-5,6-dihydro-2H-pyran-3-carbonitrile and 4,6,6-trimethyl-2-oxo-1,2,5,6-tetrahydropyridine-3-carbonitrile

  • D. Jansone
  • S. Belyakov
  • M. FleisherEmail author
  • L. Leite
  • E. Lukevics


Single crystals of 4,6,6-trimethyl-2-oxo-5,6-dihydro-2H-pyran-3-carbonitrile and 4,6,6-trimethyl-2-oxo-1,2,5,6-tetrahydropyridine-3-carbonitrile were prepared and submitted to X-ray diffraction analysis. Both compounds have a molecular structure belonging to the C1 symmetry group. The heterocyclic rings are in a distorted envelope conformation. The crystals belong to the monoclinic system and each contain four molecules in the unit cell. In the crystal the pyridine derivative exists in the form of centrosymmetric dimers stabilized by intermolecular hydrogen bonds between the oxygen atoms of the carbonyl group and the hydrogen atom at the nitrogen atom of the ring.


4,6,6-trimethyl-2-oxo-5,6-dihydro-2H-pyran-3-carbonitrile 4,6,6-trimethyl-2-oxo-1,2,5,6-tetrahydropyridine-3-carbonitrile AM1 method X-ray crystallographic analysis 


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  1. 1.
    L. Leite, D. Jansone, M. Veveris, H. Cirule, Y. Popelis, G. Melikyan, A. Avetisyan, and E. Lukevics, Eur. J. Med. Chem., 34, 859 (1999).CrossRefGoogle Scholar
  2. 2.
    D. Jansone, L. Leite, M. Fleisher, J. Popelis, I. Mazheika, E. Lukevics, G. Melikyan, and A. Avetisyan, Khim. Geterotsikl. Soedin., 298 (1998). [Chem. Heterocycl. Comp., 34, 267 (1998)].Google Scholar
  3. 3.
    L. Leite, D. Yansone, M. Fleisher, H. Kazhoka, J. Popelis, N. Veretennikova, I. Shestakova, I. Domracheva, and E. Lukevics, Khim. Geterotsikl. Soedin., 839 (2004). [Chem. Heterocycl Comp., 40, 715 (2004)].Google Scholar
  4. 4.
    D. Jansone, M. Fleisher, G. Andreeva, L. Leite, and E. Lukevics, Khim. Geterotsikl. Soedin., 1863 (2005). [Chem. Heterocycl. Comp., 41, 1537 (2005)].Google Scholar
  5. 5.
    M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, and J. J. P. Stewart, J. Am. Chem. Soc., 107, 3902 (1985).CrossRefGoogle Scholar
  6. 6.
    L. N. Kuleshova and P. M. Zorkii, Acta Cryst, B37, 1363 (1981).Google Scholar
  7. 7.
    J. J. P. Stewart, Program Package MOPAC2007.
  8. 8.
    A. F. Mishnev and S. V. Belyakov, Kristallografiya, 33, 835 (1988).Google Scholar
  9. 9.
    S. Maskay, C. J. Gilmore, C. Edwards, N. Stewart, and K. Shankland, maXus. Computer Program for the Solution and Refinement of Crystal Structures, Bruker Nonius, 1999, Netherlands, MacScience, Japan, The University of Glasgow.Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  • D. Jansone
    • 1
  • S. Belyakov
    • 1
  • M. Fleisher
    • 1
    Email author
  • L. Leite
    • 1
  • E. Lukevics
    • 1
  1. 1.Latvian Institute of Organic SynthesisRiga

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