Crystal and molecular structures of three modifications of the androgen dehydroepiandrosterone (DHEA) |
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Authors: | Mino R Caira J Keith Guillory Luh-Chian Chang |
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Institution: | (1) Department of Chemistry, University of Cape Town, 7700 Rondebosch, South Africa;(2) College of Pharmacy, The University of Iowa, 52242 Iowa City, Iowa |
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Abstract: | The crystal and molecular structures of three forms of the androgen DHEA (dehydroepiandrosterone) have been determined by single crystal X-ray diffraction. They are: Form I, a polymorph crystallizing in space group P21 withZ=4; Form S1, a hydrate with composition DHEA. (1/4)H2O, space group C2,Z=8; and Form S4, a methanol half-solvate, DHEA. (1/2)CH3OH, space group C2221,Z=8. The A, B, and C steroid ring conformations adopted in the five crystallographically independent DHEA molecules are invariably: chair, 8 , 9 -half-chair, and chair, respectively, while the D ring conformation ranges from a 14 -envelope to a 13 , 14 -half-chair. In Forms I and S1, intermolecular hydrogen bonding is of the head-to-tail type with water molecules participating as donors in Form S1. In Form S4, DHEA molecules pack in head-to-head fashion, their hydroxyl groups being linked by hydrogen bonding to the solvent hydroxyl group. The hydroxyl H atoms of both DHEA and the included methanol are disordered, giving rise to an unusual linearly-propagating flip-flop hydrogen bonding scheme. |
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Keywords: | DHEA drug polymorphism |
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