Crystal structure of flufenoxuron: a benzoyl-urea pesticide

Abstract

The title compound, C21H11ClF6N2O3 (systematic name: 1-{4-[2-chloro-4-(trifluoromethyl)phenoxy]-2-fluorophenyl}-3-(2,6-di-fluoro-benzo-yl)urea), is a benzoyl-urea pesticide. The dihedral angles between the central fluoro-benzene ring and the terminal di-fluoro-phenyl ring and chloro-phenyl ring system are 62.15 (5) and 88.03 (5)°, respectively. In the crystal, N-H⋯O hydrogen bonds link adjacent mol-ecules, forming R 2 (2)(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 inter-actions [inter-centroid distances = 3.661 (2) and 3.535 (12) Å], resulting in a three-dimensional architecture.

Keywords: C—H⋯π inter­actions; N—H⋯O hydrogen bonds; benzoyl­urea; crystal structure; pesticide; π–π inter­actions.

Fig. 1.

The molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Fig. 2.

Crystal packing of the title compound viewed along the b axis. The N—H···O hydrogen bonds, weak π···π interactions, and short F···F contacts are shown as dashed lines (see Table 1 for details).