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

Naik, V. S. and Yathirajan, H. S. and Jasinski, J. P. and Smolenski, V. A. and Glidewell, C. (2015) The crystal structures of six (2E)-3-aryl-1-(5-halogenothiophen-2-yl) prop-2-en-1-ones. ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 71 (9). 1093+. ISSN 2056-9890

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Official URL: http://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) prop2- en-1-one, C15H13BrOS, (II), are isostructural in space group P1, 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 center dot center dot center dot O hydrogen bonds. In the structure of (2E)-3-(4bromophenyl)- 1-(5-chlorothiophen-2-yl) prop-2-en-1-one, C13H8BrClOS, (V), there are again no hydrogen bonds nor pi-pi 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 center dot center dot center dot O hydrogen bonds. In each of compounds (I)-(VI), the molecular skeletons are close to planarity, and there are short halogen center dot center dot center dot halogen contacts in the structures of compounds (II) and (V) and a short Br center dot center dot center dot 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 center dot center dot center dot halogen interactions
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: Shrirekha N
Date Deposited: 30 May 2019 11:31
Last Modified: 30 May 2019 11:31
URI: http://eprints.uni-mysore.ac.in/id/eprint/708

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