Title of article :
Synthesis and crystal structures of 3-hydroxy-2,4-dimethyl-2H-thiophen-5-one and 3-hydroxy-4-methyl-2H-thiophen-5-one
Author/Authors :
Nashawi, Asma Strathclyde Institute for Pharmacy and Biomedical Sciences - University of Strathclyde, Scotland , Lawson, Christopher P. Strathclyde Institute for Pharmacy and Biomedical Sciences - University of Strathclyde, Scotland , Abdel-Sattar, M. Omar Department of Pharmaceutical Chemistry - King Abdul Aziz University, Saudi Arabia , ter Horst, Joop H. EPSRC Future Manufacturing Research Hub for Continuous Manufacture and Advanced Crystallisation (CMAC) - Technology and Innovation Centre - University of Strathclyde, Scotland , Coxon, Geoffrey D. Strathclyde Institute for Pharmacy and Biomedical Sciences - University of Strathclyde, Scotland , Kennedy, Alan R. Westchem - Department of Pure & Applied Chemistry - University of Strathclyde, Scotland
Abstract :
The structures of two hydroxy-thiophenone derivatives related to the antibiotic thiolactomycin are presented. These are the racemic 3-hydroxy-2,4-dimethyl2H-thiophen-5-one, C6H8O2S, and 3-hydroxy-4-methyl-2H-thiophen-5-one, C5H6O2S. The main structural feature of both compounds is C(6) hydrogenbonded 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 chainspropagate through a x + 3
2, y + 12, z operation, giving chains lying parallel to thecrystallographic b-axis direction that are composed of alternate R and S enantiomers. 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).
Keywords :
crystal structure , hydrogen bonding , hydroxy-thiophenone
Journal title :
Acta Crystallographica Section E: Crystallographic Communications
