Crystal Structure of 3-Oxo-4-Aza-5-Alpha-Androstone-17 β-Tert-Butyl Carboxamide with an O···H–(C, N) Acceptor Four-Center Hydrogen Bond

    December 2008 in “ Journal of Chemical Crystallography ”
    Jerry P. Jasinski, Ray J. Butcher, L. Mallesha, K. N. Mohana, H. S. Yathirajan, B. Narayana
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    TLDR The research shows that hydrogen bonds greatly affect the crystal structure of a Finasteride derivative.
    The document analyzed the crystal structure of a saturated form of Finasteride, a drug used for treating enlarged prostate glands and male pattern hair loss. The compound, with the molecular formula C23H38N2O2, crystallizes in the monoclinic space group C2 and features an O...H-(C, N) four-center hydrogen bond interaction. The study found that intermolecular hydrogen bonds significantly influence the crystal packing, while intramolecular hydrogen bonds have little effect. Comparisons with solvated analogs of Finasteride showed notable differences in dihedral angles and bond lengths, indicating the importance of solvent presence and hydrogen bonding in determining the geometric structure of the molecule. The C(1)-C(2) bond length was shorter than a typical C-C single bond, highlighting the impact of the four-center hydrogen bond. The research provides insights into the structural characteristics of Finasteride derivatives, which is crucial for understanding their function and efficacy.
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