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Crystal structure and conformational analysis of N-formyl and N-nitroso derivatives of piperidinone

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Abstract

Single crystal X-ray studies for N-formyl-2,6-diortho chlorophenyl-3,5-dimethyl piperidin-4-one (FOCDMPO) and N-nitroso-2,6-di(3′,4′,5′-trimethoxyphenyl)-3,5-dimethyl piperidin-4-one (NTMPO) are reported. Crystals of FOCDMPO and NTMPO belong to the monoclinic space groups P21/n and C2/c, respectively. FOCDMPO: a = 9.147(2), b = 14.586(3), c = 13.665(5) Å and β = 101.68(2)° NTMPO: a = 38.52(2), b = 13.727(5), c = 9.564(3) Å and β = 98.60(1)°. In both the structures, the piperidine ring adopts a boat conformation with slight distortion. In FOCDMPO, one of the phenyl and methyl groups are in axial positions while the other phenyl and methyl groups are in equatorial orientations. In NTMPO, the situation is reversed. The molecules are stabilized by weak intermolecular C—H ··· O interactions in addition to van der Waals forces.

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References

  1. Casy, A.F.; Ison, R.R. J. Pharm. Pharmacol. 1970, 22, 270.

    Google Scholar 

  2. McElvain, S.M. J. Am. Chem. Soc. 1972, 49, 2835.

    Google Scholar 

  3. Lu, Z.Y.; Zaho, S.Y.; Yuaw, X.M.; Yang, Y.L. Chem. Abstr. 1991, 114, 815135.

    Google Scholar 

  4. Hermons, B.; Van Dacle, P.; van de Westeringh, C.; van der Eycken, C.; Boey, J.; Dockx, J.; Janssen, P.A.J. J. Med. Chem. 1968, 11, 797.

    Google Scholar 

  5. Bochringer, C.F.; Soehne, G.M.B.H. Chem. Abstr. 1961, 55, 24796.

    Google Scholar 

  6. Severs, W.B.; Kinnard, W.J.; Buckley, J.P. Chem. Abstr. 1965, 63, 10538.

    Google Scholar 

  7. Ganellin, C.R.; Spickett, R.G.W. J. Med. Chem. 1965, 8, 619.

    Google Scholar 

  8. Mobio, I.G.; Soldatenkov, A.T.; Fedorov, V.O.; Ageev, E.A.; Sargeeva, N.D.; Lin, S.; Stashenko, E.E.; Prostakov, N.S.; Andreeva, E.I. Chem. Abstr. 1990, 112, 7331y.

    Google Scholar 

  9. Ferguson, L.N. Chem. Soc. Rev. 1975, 4, 289.

    Google Scholar 

  10. Magee, P.N.; Montesano, R.; Preussmann, R. Chemical Carcinogens, American Chemical Society: Washington DC, 1976; p 491.

    Google Scholar 

  11. Lijinsky, W.; Taylor, H.W. Int. J. Cancer 1975, 16, 318.

    Google Scholar 

  12. Schmelt, I.; Hoffmann, D. Chem. Rev. 1971, 77, 295.

    Google Scholar 

  13. Tricher, A.R.; Siddiqi, M.A.; Preussmann, R. In N-Nitroso Compounds: Biology and Chemistry;Bhide, S.V.; Rao, K.V.K. Eds.; Omega Scientific Publisher: New Delhi, 1990.

    Google Scholar 

  14. Sheldrick, G.M. SHELXS86 Program for the Solution of Crystal Structures; University of Go¨ ttingen, Germany, 1993.

  15. Sheldrick, G.M. SHELXL93 Program for Crystal Structure Determination, University of Go¨ ttingen, Germany, 1993.

  16. Nardelli, M. Comput. Chem. 1983, 7, 95; J. Appl. Cryst. 1995, 28, 659.

    Google Scholar 

  17. Zsolnai, L.; Pritzkow, H. ZORTEP. Interactive Graphics Program; University of Heidelberg, Germany, 1993.

  18. Zsolnai, L. ZORTEP. Interactive Graphics Program; University of Heidelberg: Germany. 1997.

  19. Sheldrick, G.M. SHELXTL/PC: Complete Software Package for Single Crystal Structure Determination; Siemens Analytical X-ray Instruments Inc: Madison WI, 1990.

    Google Scholar 

  20. Biosym Inc. Insight II; Biosym Inc., San Diego, CA, 1993.

    Google Scholar 

  21. Allen, F.H.; Kennard, O.; Watson, D.G.; Brummer, L.; Orpen, A.G.; Taylor, R. J. Chem. Soc. Perkin Trans. II. 1987, S1–S19.

  22. Roques, R.; Declercq, J.P.; Germain, G.; Graffin, P.; Kamenka, J.M.; Geneste, P. Acta Crystallogr. 1981, B37, 712.

    Google Scholar 

  23. Ress, B.; Weiss, R. Acta Crystallogr. 1971, B27, 932.

    Google Scholar 

  24. Hofer. O. Topics in Stereochemistry; Allinger N.L. Eliel E.L. Eds.; John Wiley & Sons: New York, New York 1976; p9.

    Google Scholar 

  25. Potapov, V.M. Stereochemistry Mir Publishers: Moscow, 1979.

    Google Scholar 

  26. Ramalingam, K.; Berlin, K.D.; Sathyamurthy, N.; Sivakumar, R. J. Org. Chem. 1979, 44, 471.

    Google Scholar 

  27. Mulekar, S.V.; Berlin, K.D. J. Org. Chem. 1989, 54, 4758.

    Google Scholar 

  28. Pandiarajan, K.; Sekar, R.; Anantharaman, R.; Ramalingam, U.; Marko, D. Indian J. Chem. 1991, 30B, 490.

    Google Scholar 

  29. Robins, P.A.; Walker, J. J. Chem. Soc. 1955, 1789.

  30. Klyne, W. Experientia 1956, 12, 119.

    Google Scholar 

  31. Ravindran, T.; Jeyaraman, R.; Murray, R.W.; Singh, M. J. Org. Chem. 1991, 56, 4833.

    Google Scholar 

  32. Rogers, M.J.; Woodbrey, J.C. J. Phys. Chem. 1962, 66, 540.

    Google Scholar 

  33. Looney, C.E.; Phillips, W.D.; Reilly, E.L. J. Am. Chem. Soc. 1957, 79, 6163.

    Google Scholar 

  34. Lunazzi, L.; Macciantelli, D. J. Chem. Soc. Perkin Trans. II, 1981, 406.

  35. Lunazzi, L.; Cerioni, G.; Ingold, K.U. J. Am. Chem. Soc. 1976, 98, 7484.

    Google Scholar 

  36. Lunazzi, L., Cerioni, G.; Foresti, E.; Macciantelli, D. J. Chem. Soc. Perkin Trans II, 1978, 689.

  37. Sukumar N.; Ponnuswamy, M.N.; Thenmozhiyal, J. C.; Jeyaraman, R. J. Cryst. Spec. Res. 1993, 23, 871.

    Google Scholar 

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Authors and Affiliations

  1. Department of Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai, 600 025, India

    D. Kumaran, M.N. Ponnuswamy & G. Shanmugam

  2. Department of Chemistry, Bharathidasan University, Tiruchirapalli, 620 024, India

    J.C. Thenmozhiyal & R. Jeyaraman

  3. Insituto de Quimica, Circuito Exterior, Cuidad Universitania, Delegacion Coyoacan, Mexico DF, 04510, México

    K. Panneerselvam & M. Soriano-Garcia

Authors
  1. D. Kumaran
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  2. M.N. Ponnuswamy
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  3. G. Shanmugam
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  4. J.C. Thenmozhiyal
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  5. R. Jeyaraman
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  6. K. Panneerselvam
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  7. M. Soriano-Garcia
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Kumaran, D., Ponnuswamy, M., Shanmugam, G. et al. Crystal structure and conformational analysis of N-formyl and N-nitroso derivatives of piperidinone. Journal of Chemical Crystallography 29, 769–775 (1999). https://doi.org/10.1023/A:1009587518299

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