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Journal of Chemical Crystallography

, Volume 35, Issue 8, pp 577–582 | Cite as

Crystallographic and conformational analysis of 2-methyl-3-(2-nitro-phenyl)-4-phenyl-[1,2,4]oxadiazolidin-5-one

  • Hasan Karabıyık
  • Muhittin Aygün
  • Necdet Coşkun
  • Canan Kazak
Article

Abstract

Molecular and crystal structure of 2-methyl-3-(2-nitro-phenyl)-4-phenyl-[1,2,4]oxadiazolidin-5-one, C15H13N3O4, have been determined by single crystal X-ray diffraction study. The title compound is monoclinic, with a = 10.0313(8) Å, b = 9.0372(5) Å, c = 15.5964(14) Å, β = 96.926(7), Z = 4, D x = 1.42 g/cm3, μ (Mo-Kα) = 0.105 mm−1, and space group is P 21/c. The structure was solved by direct methods and refined to a final R = 0.036 for 1894 reflections with I > 4σ (I). The crystal structure is stabilized by C–H⋅sO type inter-molecular, C–H⋅sN and C–H⋅sO type intra-molecular, π–π stacking and edge to face (C–H⋅s π-ring) interactions. To enlighten conformational flexibility of the title molecule, selected two torsion angles are varied from −180 to +180 in every 10 separetely and then molecular energy profile is calculated and construed.

Keywords

Crystal structure nitrones AM1 conformational analysis 

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References

  1. 1.
    Black, D. St. C.; Crozier, R.F.; Davis, V.C. Synthesis 1975,205.Google Scholar
  2. 2.
    Padwa, A. Angew. Chem. Int. Ed. Engl. 1976, 15, 123.CrossRefGoogle Scholar
  3. 2.
    Oppolzer, W. Angew. Chem. Int. Ed. Engl. 1977, 16, 10.CrossRefGoogle Scholar
  4. 4.
    Dell, C.P. J. Chem. Soc. Perkin Trans. I 1998, 3873.Google Scholar
  5. 5.
    Coşkun, N.; Sámengen, D. Synth. Commun. 1993, 23, 1699.Google Scholar
  6. 6.
    Coşkun, N.; Asutay, O. Chim. Acta Turc. 1997, 25, 69.Google Scholar
  7. 7.
    Coşkun, N.; Asutay, O. Chim. Acta Turc. 1999, 27, 17.Google Scholar
  8. 8.
    Coşkun, N. Tetrahedron Lett. 1997, 38, 2299.CrossRefGoogle Scholar
  9. 9.
    Coşkun, N. Tetrahedron 1997, 53, 13873.CrossRefGoogle Scholar
  10. 10.
    Coşkun, N.; Ay, M. Heterocycles 1998, 48, 537Google Scholar
  11. 11.
    Coşkun, N.; Tat, F.T.; Güven, Ö.Ö., Ülkü, D.; Arici, C. Tetrahedron Lett. 2000, 41, 5407.CrossRefGoogle Scholar
  12. 12.
    Coşkun, N.; Tat, F.T.; Güven, Ö.Ö. Tetrahedron 2001, 41, 5407.Google Scholar
  13. 13.
    Coşkun, N.; Tat, F.T.; Güven, Ö.Ö. Tetrahedron: Assym. 2001, 12, 1463.CrossRefGoogle Scholar
  14. 14.
    Coşkun, N. Turk. J. Chem. 2001, 25, 267.Google Scholar
  15. 15.
    Coşkun, N.; Tat, F.T. Phosphorus Sulfur 2003, 178, 881.CrossRefGoogle Scholar
  16. 16.
    Sheldrick, G.M. SHELXS 97 and SHELXL 97, Program for Crystal Structure Solution and Refinement; University of Göttingen: Germany, 1997.Google Scholar
  17. 17.
    Dewar, M.J.S.; Zoebsch, E.G.; Healy, E.F.; Stewart, J.J.P. J. Am. Chem. Soc. 1985, 107, 3902.CrossRefGoogle Scholar
  18. 18.
    Roothaan, C.C. J. Rev. Mod. Phys. 1951, 23, 69.CrossRefGoogle Scholar
  19. 19.
    Farrugia, L.J. ORTEP-III for Windows; Department of Chemistry, University of Glasgow: UK, 1998.Google Scholar
  20. 20.
    Clegg, W.; Elsegood, M.R.J. Acta Crystallogr. 2002, E58, o758.Google Scholar
  21. 21.
    Clegg, W.; Elsegood, M.R.J. Acta Crystallogr. 2002, E58, o760.Google Scholar
  22. 22.
    Clegg, W.; Elsegood, M.R.J. Acta Crystallogr. 2002, E58, o763.Google Scholar
  23. 23.
    Sato, S.; Yamzaki, T.; Shinohara, N.; Kitazume, T. Acta Crystallogr. 2000, C56, e592.Google Scholar

Copyright information

© Springer Science + Business Media, Inc. 2005

Authors and Affiliations

  • Hasan Karabıyık
    • 1
  • Muhittin Aygün
    • 1
  • Necdet Coşkun
    • 2
  • Canan Kazak
    • 3
  1. 1.Department of Physics, Faculty of Arts and SciencesDokuz Eylül UniversityBucaTurkey
  2. 2.Department of Chemistry, Faculty of Arts and SciencesUludağ UniversityGörükleTurkey
  3. 3.Department of Physics, Faculty of Arts and SciencesOndokuz Mayıs UniversityKurupelitTurkey

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