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Open Access The crystal structures of six (2E)-3-aryl-1-(5-halogenothiophen-2-yl)prop-2-en-1-ones

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The structures of six chalcones containing 5-halogenothiophen-2-yl substituents are reported: (2E)-1-(5-chlorothiophen-2-yl)-3-(4-ethylphenyl)prop-2-en-1-one, C15H13ClOS, (I), and (2E)-1-(5-bromothiophen-2-yl)-3-(4-ethylphenyl)prop-2-en-1-one, C15H13BrOS, (II), are isostructural in space group P-1, while (2E)-1-(5-chlorothiophen-2-yl)-3-(4-ethoxyphenyl)prop-2-en-1-one, C15H13ClO2S, (III), and (2E)-1-(5-bromothiophen-2-yl)-3-(4-ethoxyphenyl)prop-2-en-1-one C15H13BrO2S, (IV), are isostructural in space group P21/c. There are no hydrogen bonds of any kind in the structures of compounds (I) and (II), but in the structures of compounds (III) and (IV), the molecules are linked into C(7) chains by means of C—H...O hydrogen bonds. In the structure of (2E)-3-(4-bromophenyl)-1-(5-chlorothiophen-2-yl)prop-2-en-1-one, C13H8BrClOS, (V), there are again no hydrogen bonds nor π–π stacking interactions but in that of (2E)-1-(5-bromothiophen-2-yl)-3-(3-methoxyphenyl)prop-2-en-1-one, C14H11BrO2S, (VI), the molecules are linked into C(5) chains by C—H...O hydrogen bonds. In each of compounds (I)–(VI), the molecular skeletons are close to planarity, and there are short halogen...halogen contacts in the structures of compounds (II) and (V) and a short Br...O contact in the structure of compound (VI). Comparisons are made with the structures of some similar compounds.
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Document Type: Research Article

Affiliations: 1: Department of Physics, Government First Grade College, Kumta 581 343, India, Research and Development Centre, Bharathiar University, Coimbatore 641 046, India 2: Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India 3: Department of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA 4: School of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, Scotland

Publication date: January 1, 2015

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