Crystal structure of the insecticide ethiprole (C(13)H(9)Cl(2)F(3)N(4)OS): a case study of whole-mol­ecule configurational disorder

The crystal structure of ethiprole {systematic name: 5-amino-1-[2,6-di­chloro-4-(tri­fluoro­meth­yl)phen­yl]-4-ethane­sulfinyl-1H-imidazole-3-carbo­nitrile}, C(13)H(9)Cl(2)F(3)N(4)OS, 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 (4) (4)(18) and R (2) (2)(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.