Crystal structure of fipronil

The title compound, C12H4Cl2F6N4OS {systematic name: 5-amino-1-[2,6-di-chloro-4-(tri-fluoro-meth-yl)phen-yl]-4-[(tri-fluoro-methane)sulfinyl]-1H-pyrazole-3-carbo-nitrile}, is a member of the phenyl-pyrazole group of acaricides, and one of the phenyl-pyrazole group of insecticides. The dihedral angle between the planes of the pyrazole and benzene rings is 89.03 (9)°. The fluorine atoms of the tri-fluoro-methyl 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 inter-actions [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[Formula: see text]]. Finally, N-H⋯O hydrogen bonds and C-Cl⋯π inter-actions [Cl⋯ring centroid = 3.5159 (16) Å] generate a three-dimensional structure. Additionally, there are a short inter-molecular F⋯ F contacts present.