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Crystallography Reports

, Volume 63, Issue 6, pp 937–941 | Cite as

Synthesis and Single Crystal X-Ray Structure of 3,5-Diphenyl-1-(phenylacetyl)-4,5-dihydro-1H-pyrazol

  • S. Kansız
  • F. Tınmaz
  • İ. Ö. İlhan
  • E. Sarıpınar
  • N. Dege
STRUCTURE OF ORGANIC COMPOUNDS

Abstract

The molecule of the title pyrazole derivative, 3,5-diphenyl-1-(phenylacetyl)-4,5-dihydro-1H-pyrazol, C23H20N2O, is twisted. The compound crystallizes in the monoclinic sp. gr. I2/a with a = 15.3502(13) Å, b = 12.7576(8) Å, c = 19.625(2) Å, β = 106.639(7)°, and Z = 8. In the compound, the phenyl rings form dihedral angles of 12.01(13)°, 80.36(8)°, and 86.95(9)° with the mean plane of the pyrazole ring (r.m.s. deviation = 0.030 Å). The central pyrazole ring, which approximates an envelope conformation, is almost coplanar with one of the phenyl rings. The crystal packing is stabilized by weak intermolecular C–H···O hydrogen bonds.

REFERENCES

  1. 1.
    Y. B. Vibhute and M. A. Basser, Ind. J. Chem. 42B, 202 (2003).Google Scholar
  2. 2.
    B. A. Bhat, K. L. Dhar, and A. K. Saxena, Bioorgan. Med. Chem. 15 (3), 177 (2005).CrossRefGoogle Scholar
  3. 3.
    L. Michael, D. Edwards, M. Stemerick, et al., J. Med. Chem. 33, 1948 (1990).CrossRefGoogle Scholar
  4. 4.
    R. Kalirajan, M. Palanivelu, V. Rajamanickam, et al., Int. J. Chem. Sci. 5 (1), 73 (2007).Google Scholar
  5. 5.
    R. H. Udupi, R. Bhat, and K. Krishna, Indian J. Heterocycl. Chem. 8, 143 (1998).Google Scholar
  6. 6.
    A. Pande and V. K. Saxena, Ind. J. Chem. 26B, 390 (1987).Google Scholar
  7. 7.
    U. Gupta, V. Sareen, V. Khatri, et al., Indian J. Heterocycl. Chem. 14, 265 (2005).Google Scholar
  8. 8.
    V. K. Pande, V. D. Gupta, and D. N. Tiwari, Indian J. Heterocycl. Chem. 13, 399 (2004).Google Scholar
  9. 9.
    R. M. Mishra and A. Wahab, Indian J. Heterocycl. Chem. 13, 29 (2003).Google Scholar
  10. 10.
    Stoe & Cie, X-AREA and X-RED32 (Stoe & Cie, Darmstadt, Germany, 2002).Google Scholar
  11. 11.
    O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, et al., J. Appl. Crystallogr. 42, 339 (2009).CrossRefGoogle Scholar
  12. 12.
    G. M. Sheldrick, Acta Crystallogr. A 71, 3 (2015).CrossRefGoogle Scholar
  13. 13.
    L. J. Farrugia, J. Appl. Crystallogr. 45, 849 (2012).CrossRefGoogle Scholar
  14. 14.
    L. J. Farrugia, J. Appl. Crystallogr. 32, 837 (1999).CrossRefGoogle Scholar
  15. 15.
    A. L. Spek, J. Appl. Crystallogr. 36, 7 (2003).CrossRefGoogle Scholar
  16. 16.
    S. P. Westrip, J. Appl. Crystallogr. 43, 920 (2010).CrossRefGoogle Scholar
  17. 17.
    S. Fustero, A. S. Fuentes, and J. F. Sanz-Cervera, Org. Prep. Proc. Int. 41, 253 (2009).CrossRefGoogle Scholar
  18. 18.
    J. H. Safaei-Ghomi, A. Bamoniri, and M. Soltanian-Telkabadi, Chem. Heterocycl. Compd. 42, 892 (2006).CrossRefGoogle Scholar
  19. 19.
    Y. Rajendra Prasad, A. Lakshmana Rao, L. Prasoona, et al., Bioorg. Med. Chem. Lett. 15, 5030 (2005).CrossRefGoogle Scholar
  20. 20.
    S. Samshuddin, B. Narayana, B. K. Sarojini, et al., Med. Chem. Res. 21, 2012 (2012).CrossRefGoogle Scholar
  21. 21.
    Y.-S. Xie, X.-H. Pan, B.-X. Zhao, et al., J. Organomet. Chem. 693, 1367 (2008).CrossRefGoogle Scholar
  22. 22.
    X. Bai, K. Chen, Y. Zhang, et al., Acta Crystallogr. E 65, o2873 (2009).CrossRefGoogle Scholar
  23. 23.
    H.-K. Fun, T. Suwunwong, and S. Chantrapromma, Acta Crystallogr. E 67, o701 (2011).CrossRefGoogle Scholar
  24. 24.
    Z. Baktir, M. Akkurt, S. Samshuddin, et al., Acta Crystallogr. E 67, o328 (2011).CrossRefGoogle Scholar
  25. 25.
    E. I. Klimova, M. Marcos, T. B. Klimova, et al., J. Organomet. Chem. 585, 106 (1999).CrossRefGoogle Scholar
  26. 26.
    D. Bhaskarreddy, B. N. Chandrasekhar, V. Padmavathi, et al., Synthesis 3, 491 (1997).Google Scholar
  27. 27.
    R. V. Hes, K. Wellinga, and A. C. Grosscurt, J. Agric. Food Chem. 26, 915 (1978).CrossRefGoogle Scholar
  28. 28.
    F. Manna, F. Chimenti, R. Fioravanti, et al., Bioorg. Med. Chem. Lett. 15, 4632 (2005).CrossRefGoogle Scholar
  29. 29.
    M. Amir, H. Kumar, and S. A. Khan, Bioorg. Med. Chem. Lett. 18, 918 (2008).CrossRefGoogle Scholar
  30. 30.
    B. K. Sarojini, M. Vidyagayatri, C. G. Darshanraj, et al., Lett. Drug Des. Discov. 7, 214 (2010).CrossRefGoogle Scholar
  31. 31.
    H. A. Regaila, A. K. El-Bayonk, and M. Hammad, Egypt. J. Chem. 20, 197 (1979).Google Scholar
  32. 32.
    Z. Baktir, M. Akkurt, S. Samshuddin, et al., Acta Crystallogr. E 67, o1292 (2011).CrossRefGoogle Scholar
  33. 33.
    S. Samshuddin, B. Narayana, H. S. Yathirajan, et al., Acta Crystallogr. E 66, o1279 (2010).CrossRefGoogle Scholar
  34. 34.
    H.-K. Fun, C. K. Quah, S. Priya, et al., Acta Crystallogr. E 68, o818 (2012).CrossRefGoogle Scholar
  35. 35.
    J. P. Jasinski, C. J. Guild, S. Samshuddin, et al., Acta Crystallogr. E 66, o1948 (2010).CrossRefGoogle Scholar
  36. 36.
    J. P. Jasinski, A. E. Pek, S. Samshuddin, et al., Acta Crystallogr. E 66, o1950 (2010).CrossRefGoogle Scholar
  37. 37.
    H.-K. Fun, M. Hemamalini, S. Samshuddin, et al., Acta Crystallogr. E 66, o582 (2010).CrossRefGoogle Scholar
  38. 38.
    D. Cremer and J. A. Pople, J. Am. Chem. Soc. 97, 1354 (1975).CrossRefGoogle Scholar
  39. 39.
    F. H. Allen, O. Kennard, D. G. Watson, et al., J. Chem. Soc. Perkin Trans. 2, S1 (1987).CrossRefGoogle Scholar
  40. 40.
    V. Kettmann, J. Svetlik, and J. Kubista, Acta Crystallogr. C 60, o431 (2004).CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Inc. 2018

Authors and Affiliations

  • S. Kansız
    • 1
  • F. Tınmaz
    • 2
  • İ. Ö. İlhan
    • 2
  • E. Sarıpınar
    • 2
  • N. Dege
    • 1
  1. 1.Ondokuz Mayıs University, Faculty of Arts and Sciences, Department of PhysicsSamsunTurkey
  2. 2.Erciyes University, Department of Chemistry, Faculty of SciencesKayseriTurkey

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