Crystal structure of the insecticide ethiprole (C13H9Cl2F3N4OS): a case study of whole-mol­ecule configurational disorder

Vinaya and Basavaraju, Y. B. and Srinivasa, G. R. and Shreenivasa, M. T. and Yathirajan, H. S. and Parkin, Sean (2023) Crystal structure of the insecticide ethiprole (C13H9Cl2F3N4OS): a case study of whole-mol­ecule configurational disorder. Acta Crystallographica Section E, 79 (2). pp. 54-59. ISSN 2056-9890

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Official URL: https://doi.org/10.1107/S205698902300035X

Abstract

The crystal structure of ethiprole {systematic name: 5-amino-1-[2,6-di­chloro-4-(tri­fluoro­meth­yl)phen­yl]-4-ethane­sulfinyl-1H-imidazole-3-carbo­nitrile}, C13H9Cl2F3N4OS, a phenyl­pyrazole-based insecticide, is presented. The pyrazole ring carries four substituents: an N-bound 2,6-di­chloro-4-tri­fluoro­methyl­phenyl ring and C-bound amine, ethane­sulfinyl, and cyano groups. The sulfur atom of the ethane­sulfinyl group is trigonal–pyramidal and stereogenic. The structure exhibits whole-mol­ecule configurational disorder due to superposition of enanti­omers. The crystal packing is dominated by strong N—H⋯O and N—H⋯N hydrogen bonds, which form R44(18) and R22(12) ring motifs. Since the ethiprole mol­ecule is quite small, and structure solution and refinement were straightforward, the structure presents a convenient instructional example for modelling whole-body disorder of a non-rigid mol­ecule. To this end, a step-by-step overview of the model-building and refinement process is also given. The structure could form the basis of a useful classroom, practical, or workshop-style example.

Item Type: Article
Uncontrolled Keywords: ethiprole, phenylpyrazole insecticide, whole-molecule disorder, configurational disorder, refinement strategy, instructional tool, crystal structure
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: C Swapna Library Assistant
Date Deposited: 01 Feb 2023 05:29
Last Modified: 01 Feb 2023 05:29
URI: http://eprints.uni-mysore.ac.in/id/eprint/17432

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