Androstane-3β,5α,6β,17β-tetrol tri-hydrate

Abstract

The title hydrated tetrol, C(19)H(32)O(4)·3H(2)O, was synthesized by stereoselective reduction of the compound 3β,5α,6β-trihy-droxy-androstan-17-one. All rings are fused trans. The organic mol-ecules are connected head-to-tail along the c axis via O-H⋯O hydrogen bonds. Layers of water mol-ecules in the ab plane inter-connect these chains. A quantum chemical ab initio Roothan Hartree-Fock calculation of the isolated mol-ecule gives values for the mol-ecular geometry close to experimentally determined ones, apart from the C-O bond lengths, whose calculated values are significantly smaller than the measured ones, probably a consequence of the involvement of the C-OH groups in the hydrogen-bonding network.