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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.

SUBMITTER: Andrade LC

PROVIDER: S-EPMC3151997 | biostudies-literature | 2011 Jul

REPOSITORIES: biostudies-literature

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

Andrade L C R LC de Almeida M J B M MJ Paixão J A JA Carvalho J F S JF Sá E Melo M L ML

Acta crystallographica. Section E, Structure reports online 20110611 Pt 7

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 determ ...[more]

PMID: 21837048

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