Crystal structure of penoxsulam

Abstract

The title compound, C16H14F5N5O5S [systematic name: 2-(2,2-difluoroethoxy)-N-(5,8-dimethoxy-1,2,4-triazolo[1,5-c]pyrimidin-2-yl)-6-(trifluoromethyl)benzenesulfonamide], is used as a herbicide. The asymmetric unit of this structure comprises two independent molecules, A and B. The dihedral angles between the ring planes of the triazolopyrimidine ring systems and the benzene rings are 68.84 (7)° for A and 68.05 (6)° for B. In the crystal, weak intermolecular π–π interactions, with centroid–centroid separations of 3.4456 (17) and 3.5289 (15) Å and C—F...π [3.5335 (17) Å and 107.92 (13)°] contacts link adjacent molecules into chains along [001]. C—H...O and C—H...F hydrogen bonds link type B molecules into chains parallel to (100). Additional C—H...F hydrogen bonds together with short F...F contacts further aggregate the structure into a three-dimensional network.

Keywords

• crystal structure
• sulfonamide herbicides
• triazolopyrimidine herbicides
• penoxsulam