Crystal structure and Hirshfeld surface analysis of 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-N-(pyridin-2-ylmethyl)benzamide

Abstract

The title compound, C18H18F2N2O3, crystallizes with two independent molecules (A and B) in the asymmetric unit. They differ essentially in the orientation of the pyridine ring with respect to the benzene ring; these two rings are inclined to each other by 53.3 (2)° in molecule A and by 72.9 (2)° in molecule B. The 3-(cyclopropylmethoxy) side chain has an extended conformation in both molecules. The two molecules are linked by a pair of C—H...O hydrogen bonds and two C—H...π interactions, forming an A–B unit. In the crystal, this unit is linked by N—H...O hydrogen bonds, forming a zigzag –A–B–A–B– chain along [001]. The chains are linked by C—H...N and C—H...F hydrogen bonds to form layers parallel to the ac plane. Finally, the layers are linked by a third C—H...π interaction, forming a three-dimensional structure. The major contributions to the Hirshfeld surface are those due to H...H contacts (39.7%), followed by F...H/H...F contacts (19.2%).