Crystal structure of phenyl N-(3,5-dimethylphenyl)carbamate

Abstract

The asymmetric unit of the title compound, C15H15NO2, contains two independent molecules (A and B). The dimethylphenyl ring, the phenyl ring and the central carbamate N—C(=O)—O group are not coplanar. In molecule A, the dimethylphenyl and phenyl rings are inclined to the carbamate group mean plane by 27.71 (13) and 71.70 (4)°, respectively, and to one another by 84.53 (13)°. The corresponding dihedral angles in molecule B are 34.33 (11), 66.32 (13) and 85.48 (12)°, respectively. In the crystal, the A and B molecules are arranged alternately linked through N—H...O(carbonyl) hydrogen bonds, forming –A–B–A–B– chains, which extend along [100]. Within the chains and linking neighbouring chains there are C—H...π interactions present, forming columns along the a-axis direction. The columns are linked by offset π–π stacking interactions, forming a three-dimensional network [shortest centroid–centroid distance = 3.606 (1) Å].

Keywords

• crystal structure
• carbamate
• ester
• (dimethylphenyl)carbamate
• N—H...O hydrogen bonding
• C—H...π interactions
• π–π interactions