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

Vinaya, Yeriyur B. Basavaraju, Gejjelegere R. Srinivasa, Mellekatte T. Shreenivas, Hemmige S. Yathirajan, Sean Parkin

Research output: Contribution to journalArticlepeer-review

4 Scopus citations


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 languageEnglish
Pages (from-to)54-59
Number of pages6
JournalActa Crystallographica Section E: Crystallographic Communications
StatePublished - 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.


  • 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


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