Crystal structure and Hirshfeld-surface analysis of an etoxazole metabolite designated R13

Thaluru M. Mohan, Kumar and Besagarahally L., Bhaskar and Prabhakar, Priyanka and Thayamma R., Divakara and Hemmige S., Yathirajan and Sean, Parkin (2024) Crystal structure and Hirshfeld-surface analysis of an etoxazole metabolite designated R13. Acta Crystallographica Section E: Crystallographic Communications, 80 (12). pp. 1270-1273. ISSN 20569890

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Abstract

The etoxazole metabolite R13, systematic name 4-(4-tert-butyl-2-ethoxyphenyl)-2-(2,6-difluorophenyl)oxazole (C21H21F2NO2), results from the oxidation of etoxazole, a chitin synthesis inhibitor belonging to the oxazoline class, widely used as an insecticide/acaricide since 1998. The structure of R13 features a central oxazole ring with attached 2,6-difluorophenyl and 4-t-butyl-2-ethoxy-phenyl moieties. The overall conformation gives dihedral angles between these rings and the oxazole of 24.91 (5)◦ (with difluorophenyl) and 15.30 (6)◦ (with tbutyl-ethoxyphenyl), indicating an overall deviation from planarity. Additionally, torsion angles of the ethoxy and t-butyl groups define the orientation of these substituents relative to their benzene ring. In the crystal packing, no significant hydrogen bonds are present, but a Hirshfeld surface analysis highlights weak intermolecular contacts leading to π–π-stacked dimers linked by weak C—H· · ·N contacts. The packing analysis confirms that most intermolecular interactions involve hydrogen atoms. © 2024 International Union of Crystallography. All rights reserved.

Item Type:	Article
Uncontrolled Keywords:	acaricide; crystal structure; etoxazole metabolite R13; Hirshfeld surface analysis; insecticide
Subjects:	C Chemical Science > Chemistry
Divisions:	Department of > Chemistry
Depositing User:	Mr Eranna Library
Date Deposited:	04 Dec 2025 13:42
Last Modified:	04 Dec 2025 13:42
URI:	http://eprints.uni-mysore.ac.in/id/eprint/18205

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