Crystal structure and Hirshfeld surface analysis of 3-[2-(3,5-dimethylphenyl)hydrazinylidene]benzofuran-2(3H)-one

Abstract

In the title compound, C16H14N2O2, the 2,3-dihydro-1-benzofuran ring system is essentially planar and makes a dihedral angle of 3.69 (7)° with the dimethylphenyl ring. The molecular conformation is stabilized by an intramolecular N—H...O hydrogen bond with an S(6) ring motif. In the crystal, molecules are connected by C—H...π and π–π stacking interactions, forming a layer lying parallel to the (11\overline{1}) plane. One methyl group is disordered over two orientations, with occupancies of 0.67 (4) and 0.33 (4). Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H...H (51.2%), O...H/H...O (17.9%), C...H/H...C (15.2%) and C...C (8.1%) contacts.