Synthesis and crystal structures of 3-hy-droxy-2,4-dimethyl-2 H -thio-phen-5-one and 3-hy-droxy-4-methyl-2 H -thio-phen-5-one.

Autor: Nashawi A; Strathclyde Institute for Pharmacy and Biomedical Sciences, University of Strathclyde, 161 Cathedral Street, Glasgow G4 0RE, Scotland.; Department of Pharmaceutical Chemistry, King Abdul Aziz University, Jeddah, 21589, Saudi Arabia., Lawson CP; Strathclyde Institute for Pharmacy and Biomedical Sciences, University of Strathclyde, 161 Cathedral Street, Glasgow G4 0RE, Scotland., Abdel-Sattar MO; Department of Pharmaceutical Chemistry, King Abdul Aziz University, Jeddah, 21589, Saudi Arabia.; Department of Chemistry, Al-Azhar University, Cairo, 11884, Egypt., Ter Horst JH; EPSRC Future Manufacturing Research Hub for Continuous Manufacture and Advanced Crystallisation (CMAC), Technology and Innovation Centre, University of Strathclyde, 99 George Street, Glasgow G1 1RD, Scotland., Coxon GD; Strathclyde Institute for Pharmacy and Biomedical Sciences, University of Strathclyde, 161 Cathedral Street, Glasgow G4 0RE, Scotland., Kennedy AR; Westchem, Department of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland.
Jazyk: angličtina
Zdroj: Acta crystallographica. Section E, Crystallographic communications [Acta Crystallogr E Crystallogr Commun] 2020 Jun 30; Vol. 76 (Pt 7), pp. 1158-1162. Date of Electronic Publication: 2020 Jun 30 (Print Publication: 2020).
DOI: 10.1107/S2056989020008269
Abstrakt: 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-2 H -thio-phen-5-one, C 6 H 8 O 2 S, and 3-hy-droxy-4-methyl-2 H -thio-phen-5-one, C 5 H 6 O 2 S. The main structural feature of both compounds is C (6) hydrogen-bonded chains formed between the OH and C=O groups. In achiral C 5 H 6 O 2 S, these chains propagate only by translation, corresponding to x  + 1, y , z  + 1. However, in contrast, for racemic C 6 H 8 O 2 S 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).
(© Nashawi et al. 2020.)
Databáze: MEDLINE
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