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

Naik, Vasant S. and Yathirajan, H. S. and Jasinski, Jerry P. and Smolenski, Victoria A. and Glidewell, Christopher (2015) The crystal structures of six (2E)-3-aryl-1-(5-halogeno­thio­phen-2-yl)prop-2-en-1-ones. Acta Crystallographica Section E, 71 (9). pp. 1093-1099. ISSN 2056-9890

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Official URL: https://doi.org/10.1107/S2056989015015534

Abstract

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.

Item Type: Article
Uncontrolled Keywords: crystal structure, chalcones, halogenothiophens, hydrogen bonding, halogen...halogen interactions
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: MUL SWAPNA user
Date Deposited: 30 Oct 2019 09:22
Last Modified: 30 Oct 2019 09:22
URI: http://eprints.uni-mysore.ac.in/id/eprint/9708

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