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 R 44 (18) and R 22 (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.
Original language | English |
---|---|
Pages (from-to) | 54-59 |
Number of pages | 6 |
Journal | Acta Crystallographica Section E: Crystallographic Communications |
Volume | 79 |
DOIs | |
State | Published - Jan 19 2023 |
Bibliographical note
Funding Information:Funding for this research was provided by: NSF (MRI CHE1625732) and the University of Kentucky (Bruker D8 Venture diffractometer) to SP.
Funding Information:
One of the authors (V) is grateful to the DST–PURSE Project, Vijnana Bhavana, UOM for providing research facilities. HSY thanks UGC for a BSR Faculty fellowship for three years.
Publisher Copyright:
© 2023 International Union of Crystallography. All rights reserved.
Keywords
- configurational disorder
- crystal structure
- ethiprole
- instructional tool
- phenylpyrazole insecticide
- refinement strategy
- whole-molecule disorder
ASJC Scopus subject areas
- Chemistry (all)
- Materials Science (all)
- Condensed Matter Physics