Crystal structure of tolyl-fluanid

Acta Crystallogr Sect E Struct Rep Online. 2014 Sep 20;70(Pt 10):o1114-5. doi: 10.1107/S1600536814020741. eCollection 2014 Oct 1.

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.