Crystal structure of tolyl-fluanid

Abstract

The title compound, C10H13Cl2FN2O2S2 {systematic name: N-[(di-chloro-fluoro-methyl)-sulfanyl]-N',N'-dimethyl-N-p-tolyl-sulfamide}, is a well known fungicide. The dihedral angle between the mean plane of the di-methyl-amino group and that of the benzene ring is 32.3 (3)°. One Cl atom and one F atom of the di-chloro-fluoro-methyl-thio group are disordered over two sets of sites with an occupancy ratio of 0.605 (9):0.395 (9). In the crystal structure, two C-H⋯Cl hydrogen bonds link adjacent mol-ecules, forming dimers with R 2 (2)(14) loops. C-H⋯O hydrogen bonds link pairs of dimers into chains along the b-axis direction. These chains are joined by an additional C-H⋯O contact, generating a sheet in the ab plane.

Keywords: crystal structure; fungicide; hydrogen bonds; tolyl­fluanid.

Fig. 1.

The asymmetric unit of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius. Only atoms of the major disorder components are shown.

Fig. 2.

Crystal packing of the title compound with C–H···Cl and C–H···O hydrogen bonds are shown as dashed lines. H atoms bonded to C atoms have been omitted for clarity, except H atoms of hydrogen bonds. Only atoms of the major disorder components are shown.