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

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

Format: Article
Diterbitkan: International Union of Crystallography 2023-02-01

Deskripsi

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.