Abstract
An alkaloid, C20H35N3, mp 113–114 ° C, isolated fromHovea linearis R. Br., was shown to be an optically active 16-epiormosanine, [α]D = 0.0 ° in ethanol. It crystallizes in the orthorhombic space groupP212121, with unit cell dimensionsa = 11.939(1),b = 14.143(1),c = 22.310(2) Å,Z = 8, and the two molecules in the asymmetric unit are of the same chirality. The x-ray crystal structure was solved by direct methods and refined, using difference and least-squares procedures, with 2516 intensities (I > 3σ I ) measured with CuKα radiation on a single-crystal diffractometer. The final refinement of the fractional coordinates and isotropic thermal parameters of the nonhydrogen atoms, with all the hydrogens included, yielded anR index of 0.082. The molecule of 16-epiormosanine resembles the related alkaloid podopetaline in the conformation of the fused ring system.
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References
Busing, W. R. and Levy, H. A. (1959)Acta Crystallogr. 10, 180.
Cannon, J. R., Williams, J. R., Blount, J. F., and Brossi, A. (1974)Tetrahedron Letters, 1683.
Cromer, D. T. and Mann, J. B. (1968)Acta Crystallogr. A24, 321.
Deslongchamps, P., Valenta, Z. and Wilson, J. S. (1966)Can. J. Chem. 44, 2539.
Hart, N. K., Johns, S. R., Lamberton, J. A., Mackay, M. F., Mathieson, A. McL. and Satzke, L. (1972)Tetrahedron Letters, 5333.
Hassall, C. H. and Wilson, E. M. (1961)Chem. Ind. (London), 1358.
Johnson, C. K. (1965) Fortran Thermal-ellipsoid Plot Program (ORTEP). (Oak Ridge National Laboratory, Oak Ridge, Tennessee).
Karle, I. L. and Karle, J. (1963)Tetrahedron Letters, 2065.
Karle, I. L. and Karle, J. (1964)Acta Crystallogr. 17, 1356.
Karle, I. L. and Karle, J. (1966)Acta Crystallogr. 21, 849.
Konovalova, R. A., Diskina, B. S. and Rabinovitch, M. S. (1951)Zh. Obshch. Khim. 21, 773;Chem. Abstr. (1951)45, 9548e.
Lamberton, J. A., Mackay, M. F., McCall, M. J., Poppleton, B. J. and Suares, H, (1975)Tetrahedron Letters, 3875.
Lloyd, H. A. and Horning, E. C. (1958)J. Amer. Chem. Soc. 80, 1506.
Mackay, M. F., Satzke, L. and Mathieson, A. McL. (1975)Tetrahedron 31, 1295.
McLean, S., Roy, M. L., Liu, H. J. and Chu, D. T. (1972)Can. J. Chem. 50, 1639.
McLean, S. and Misra, R. (1974)Can. J. Chem. 52, 1907.
Molecular Structures and Dimensions (1972) Vol. A1, p. XV (Utrecht: Oostoek).
Naegeli, P., Wildman, W. C. and Lloyd, H. A. (1963)Tetrahedron Letters, 2069.
Stewart, R. F., Davidson, E. R. and Simpson, W. T. (1965)J. Chem. Phys. 42, 3175.
Stewart, J. M., Kruger, C. J., Ammon, H. L., Dickerson, C. and Hall, S. R. (1972) X-ray-72, A System of Computer Codes for Crystallography, Technical Report TR-192 (University of Maryland).
Tables of Interatomic Distances and Configurations in Molecules and Ions (1965) (Supplement 1956–1959), Special Publication No. 18 (The Chemical Society, London).
White, E. P. (1951)New Zealand J. Sci. Technol. 33B, 54.
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Mackay, M.F., McCall, M.J. & Poppleton, B.J. Crystal and molecular structure of an optically active 16-epiormosanine. Journal of Crystal and Molecular Structure 6, 125–137 (1976). https://doi.org/10.1007/BF01200580
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DOI: https://doi.org/10.1007/BF01200580