Crystal structure of chlorfluazuron

Abstract

The title compound (systematic name: 1-{3,5-dichloro-4-[3-chloro-5-(trifluoromethyl)pyridin-2-yloxy]phenyl}-3-(2,6-difluorobenzoyl)urea), C20H9Cl3F5N3O3, is a benzoylphenylurea insecticide. The dihedral angles between the planes of the central dichlorophenyl and the terminal difluorophenyl and chloropyridyl rings are 79.51 (6) and 78.84 6)°, respectively. In the crystal, pairs of N—H...O hydrogen bonds link adjacent molecules, formingR22(8) inversion dimers. In addition, the dimers are linked by short F...Cl [3.1060 (16) Å] and Cl...Cl [3.2837 (7) Å] contacts, as well as weak intermolecular π–π interactions [ring centroid separation = 3.6100 (11) and 3.7764 (13) Å], resulting in a two-dimensional architecture parallel to (111).