Crystal structure of ethyl N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)carbamate

Abstract

In the title compound, C14H17N3O3, the dihedral angle between the benzene ring and the five-membered dihydropyrazole ring is 52.26 (9)°. The ethyl ester group is approximately planar (r.m.s. deviation 0.0568 Å) and subtends an angle 67.73 (8)° to the pyrazole ring. In the crystal, molecules are linked by pairs of N—H...O hydrogen bonds, forming inversion dimers with an R22(10) ring motif. Weaker C—H...O contacts link these dimers into a three-dimensional network of molecules stacked along the a-axis direction. Offset π–π stacking interactions between the benzene rings [centroid-to-centroid distance = 3.8832 (12) Å] further stabilize the crystal packing.

Keywords

• crystal structure
• dihydropyrazole
• ethyl ester
• carbamate
• hydrogen bonding
• π–π stacking interactions