Crystal structure of pencycuron

Abstract

In the title compound [systematic name: 1-(4-chlorobenzyl)-1-cyclopentyl-3-phenylurea], C19H21ClN2O, which is a urea fungicide, the cyclopentyl ring adopts an envelope conformation, with one of the methylene C atoms adjacent to the C atom bonding to the N atom as the flap. The dihedral angles between the mean planes of the central cyclopentyl ring (all atoms) and the chlorobenzyl and phenyl rings are 77.96 (6) and 57.77 (7)°, respectively. In the crystal, N—H...O hydrogen bonds link adjacent molecules, forming C(4) chains propagating along the b-axis direction. The chains are linked by weak π–π interactions between the chlorobenzene rings [centroid–centroid separation = 3.9942 (9) Å], resulting in two-dimensional networks extending parellel to the (110) plane.

Keywords

• crystal structure
• pencycuron
• urea
• fungicide
• hydrogen bonding
• π–π interactions