Crystal structure of flufenoxuron: a benzoylurea pesticide

Abstract

The title compound, C21H11ClF6N2O3 (systematic name: 1-{4-[2-chloro-4-(trifluoromethyl)phenoxy]-2-fluorophenyl}-3-(2,6-difluorobenzoyl)urea), is a benzoylurea pesticide. The dihedral angles between the central fluorobenzene ring and the terminal difluorophenyl ring and chlorophenyl ring system are 62.15 (5) and 88.03 (5)°, respectively. In the crystal, N—H...O hydrogen bonds link adjacent molecules, forming R22(8) inversion dimers that pack into loop chains along the a-axis direction by short F...F contacts [2.729 (2) Å]. In addition, the chains are linked by weak C—H...π and π–π interactions [inter-centroid distances = 3.661 (2) and 3.535 (12) Å], resulting in a three-dimensional architecture.

Keywords

• crystal structure
• benzoylurea
• pesticide
• N—H...O hydrogen bonds
• C—H...π interactions
• π–π interactions