Structure of 1 alpha,3 alpha-trimethylene-2',5-epoxyandrostane-3 beta, 17 beta-diol 17-propionate methanol solvate (1/0.5).

W. L. Duax*, P. D. Strong, Z. Wawrzak, Z. Gałdecki, P. Grochulski

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    Abstract

    C25H38O4.0.5CH4O, Mr = 418.6, monoclinic, P2(1), a = 19.8504 (20), b = 7.3909 (4), c = 15.7998 (18) A, beta = 93.09 (2) degrees, V = 2314.7 (8) A3, Z = 4, D chi = 1.201 Mg m-3, lambda(Cu K alpha) = 1.54184 A, mu = 0.604 mm-1, F(000) = 916, T = 295 K, R = 0.056 for 4946 unique observed reflections. The crystallographic asymmetric unit contains two steroid molecules and a molecule of methanol. All six-membered rings for both molecules have chair conformations. The D ring has a 13 beta-envelope conformation in molecule 1 and a 13 beta, 14 alpha-half-chair conformation in molecule 2. The most significant differences between the crystallographically independent steroids are in the orientation of the H atoms of the C(3) hydroxyl groups and the conformations of the propionate side chains. When the crystallographically observed molecules are subjected to energy minimization their respective hydroxyl H-atom orientations are retained, but the D rings of both molecules refine to a common 13 beta,14 alpha-half-chair conformation and a significantly different orientation of the C(17) propionate side chain is generated. A comparison with other C(17)-ester-bearing steroids suggests that the energy minimization fails to simulate fully all intramolecular interactions.

    Original languageEnglish (US)
    Pages (from-to)1430-1433
    Number of pages4
    JournalActa crystallographica. Section C, Crystal structure communications
    Volume44 ( Pt 8)
    DOIs
    StatePublished - Aug 15 1988

    ASJC Scopus subject areas

    • Biochemistry, Genetics and Molecular Biology(all)

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