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International Union of Crystallography, Acta Crystallographica Section E: Structure Reports Online, 5(67), p. o1056-o1057, 2011

DOI: 10.1107/s1600536811011706

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3β,5α,6β-Trihy­droxy­androstan-17-one

This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

The title compound, C19H30O4, is an androstan-17-one derivative synthesized from the dehydro­epiandrosterone through a sequential addition of an oxidant, followed by a trans-diaxial opening of the epoxide generated, with Bi(OTf)3 (OTf is trifluoro­methane­sulfonate). The six-membered rings have a slightly flattened chair conformation, while the five-membered ring adopts a 14-α envelope conformation. All rings are trans fused. In the crystal, the mol­ecules are connected by O—H⋯O hydrogen bonds involving the hydroxyl and carbonyl groups, forming a three-dimensional network. A quantum mechanical ab initio Roothan Hartree–Fock calculation of the free mol­ecule gives bond lengths, valency angles and ring torsion angles of the free molecule at equilibrium geometry (energy minimum) close to the experimental values.