Crystal structure of fipronil

The title compound, C(12)H(4)Cl(2)F(6)N(4)OS {systematic name: 5-amino-1-[2,6-di­chloro-4-(tri­fluoro­meth­yl)phen­yl]-4-[(tri­fluoro­methane)sulfinyl]-1H-pyrazole-3-carbo­nitrile}, is a member of the phenyl­pyrazole group of acaricides, and one of the phenyl­pyrazole group of insecticides. The dihedral angle between the planes of the pyrazole and benzene rings is 89.03 (9)°. The fluorine atoms of the tri­fluoro­methyl substituent on the benzene ring are disordered over two sets of sites, with occupancy ratios 0.620 (15):0.380 (15). In the crystal, C—N⋯π inter­actions [N⋯ring centroid = 3.607 (4) Å] together with N—H⋯N and C—H⋯F hydrogen bonds form a looped chain structure along [10[Image: see text]]. Finally, N—H⋯O hydrogen bonds and C—Cl⋯π inter­actions [Cl⋯ring centroid = 3.5159 (16) Å] generate a three-dimensional structure. Additionally, there are a short inter­molecular F⋯ F contacts present.