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Molecular and crystal structure of bis-quinolizidine immonium salts: I. Δ1(6)-dehydro-17-oxosparteinium perchlorate

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Abstract

Δ1(6)-Dehydro-17-oxosparteinium perchlorate, [C15H23N2O]+·C10 4 , is monoclinic:P21,a=8.620(1),b=14.406(2),c=6.825(1) Å, β=101.97(1)°,Z=2,V c=829.1(1)Å3,D x=1.52g cm−3, μ (Cukα)=21.7cm−1. The finalR was 0.051 for 1159 observed counterreflections. Carbon atoms C(3) and C(4) are highly disordered. This is probably due to conformational properties of the ringA, which are caused by the

group situated between ringsA andB. RingsB,C, andD have sofa, sofa, and chair conformations, respectively. The bond distances and valency angles of the quinolizidone moiety (ringsC andD) are in good agreement with those obtained previously for 17-oxosparteine (free base) and its perchlorate salt. The title compound was obtained from Δ5-dehydro-17-oxosparteine, the product of mercuric acetate dehydrogenation of 17-oxosparteine. From IR spectra in the condensed phase and13C-NMR measurements in DMSO-2H6 solution, it is evident that, in the crystalline state as well as in solution, the immoniumlactam molecular structure is present in the compound studied.

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References

  • Bohlmann, F., and Zeisberg, R. (1975)Chem. Ber. 108, 1043.

    Google Scholar 

  • Boucourt, R. (1974) InTopics in Stereochemistry, Vol. 8, E. L. Eliel and N. L. Allinger, eds. (Wiley, New York).

    Google Scholar 

  • Cook, A. G. (1969)Enamines: Synthesis, Structure, and Reactions (Marcel Dekker, New York and London).

    Google Scholar 

  • Dashevsky, V. G. (1974)Conformations of Organic Molecules [Russian], (Khimiya, Moscow), p. 188.

    Google Scholar 

  • Duax, W. L., and Norton, D. A. (1975)Atlas of Steroid Structure (Plenum Press, New York and London)

    Google Scholar 

  • Hirshfeld, F. L. (1976)Acta Cryst. A 32, 239.

    Google Scholar 

  • Kaluski, Z., Skolik, J., and Wiewiórowski, M. (1978) Proc. Precongress Symposium on Organic Chemistry, Dymaczewo, Poland.

  • Katrusiak, A., Hoser, A., Grzesiak, E., and Kaluski, Z. (1980)Acta Cryst. B 36, 2442.

    Google Scholar 

  • Katrusiak, A., Hoser, A., and Kaluski, Z. (1982). in preparation.

  • Lehmann, M. S., and Larsen, F. K. (1974)Acta Cryst. A 30, 580.

    Google Scholar 

  • Robinson, T. (1968)The Biochemistry of Alkaloids in Molecular Biology, Biochemistry, and Biophysics (Springer-Verlag, Berlin, Heidelberg, and New York).

    Google Scholar 

  • Schweicer, W. B., Procter, G., Kaftory, M., and Dunitz, J. D. (1978)Helv. Chim. Acta 61, 2783.

    Google Scholar 

  • Sheldrick, G. (1976) Program for Crystal Structure DeterminationShelx-76, Cambridge, England.

  • Skolik, J. (1974).Zesz. Nauk. Wyzsza Szk. Ekon. Poznaniu, Ser. I, No. 53, 165.

    Google Scholar 

  • Skolik, J., and Pokdowińska, H. (1981) First International Conference on Chemistry and Biotechnology of Biologically Active Natural Products, Varna, Bulgaria (Proceedings, late papers).

  • Trefonas, L. M., Flurry, R. L., Jr., Majeste, R., Mayers, E. A., and Copeland, R. F. (1966)J. Am. Chem. Soc. 88, 2145.

    Google Scholar 

  • Wiewiórowski, and Skolik, J. (1963).

Download references

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Katrusiak, A., Kałuski, Z., Pietrzak, P. et al. Molecular and crystal structure of bis-quinolizidine immonium salts: I. Δ1(6)-dehydro-17-oxosparteinium perchlorate. Journal of Crystallographic and Spectroscopic Research 13, 151–163 (1983). https://doi.org/10.1007/BF01246584

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