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Synthesis and crystal structures of 3-hy-droxy-2,4-dimethyl-2H-thio-phen-5-one and
Asma Nashawi1,2, Christopher P Lawson1, M Omar Abdel-Sattar2,3
1Strathclyde Institute for Pharmacy and Biomedical Sciences, University of Strathclyde, 161 Cathedral Street, Glasgow G4 0RE, Scotland.
Abstract:
The structures of two hy-droxy-thio-phenone derivatives related to the anti-biotic thiol-actomycin are presented. These are the racemic 3-hy-droxy-2,4-dimethyl-2H-thio-phen-5-one, C6H8O2S, and 3-hy-droxy-4-methyl-2H-thio-phen-5-one, C5H6O2S. The main structural feature of both compounds is C(6) hydrogen-bonded chains formed between the OH and C=O groups. In achiral C5H6O2S, these chains propagate only by translation, corresponding to x + 1, y, z + 1. However, in contrast, for racemic C6H8O2S the hydrogen-bonded chains propagate through a -x + , y + , z operation, giving chains lying parallel to the crystallographic b-axis direction that are composed of alternate R and S enanti-omers. The crystals of 3-hydroxy-4-methyl-2H-thiophen-5-one were found to be twinned by a 180° rotation about the reciprocal 001 direction. In the final refinement the twin ratio refined to 0.568 (2):0.432 (2).
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