N-(2,5-Dichlorophenyl)methanesulfonamide

The conformation of the N - H bond in the structure of the title compound, C7H7Cl2NO2S, is nearly syn to the ortho-chloro group and anti to the meta-chloro group, similar to that in N-(2,5-dimethylphenyl)methanesulfonamide determined under identical conditions. This is in contrast to the syn conformations observed with respect to both ortho- and meta-chloro substituents in N-(2,3-dichlorophenyl)methanesulfonamide and the conformation lying between syn and anti to the chloro substituents at ortho or meta positions in N-(2-chlorophenyl) methanesulfonamide and N-(3-chlorophenyl)-methanesulfonamide. The geometric parameters are similar to those in other methanesulfonanilides except for some differences in the bond and torsion angles. The amide H atom is available to a receptor molecule during its biological activity as it lies on one side of the plane of the benzene ring, while the methanesulfonyl group is on the opposite side of the plane, similar to that in other methanesulfonanilides. The molecules in the title compound are packed into chains through N - H...O and N - H...Cl hydrogen bonding.