Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hydroxy-4-methylanilino)methylidene]-4-methylcyclohexa-2,4-dien-1-one

Abstract

The title compound, C15H15NO2, is a Schiff base that exists in the keto-enamine tautomeric form and adopts a Z configuration. The molecule is almost planar, with the two phenyl rings twisted relative to each other by 9.60 (18)degrees. There is an intramolecular N-H center dot center dot center dot O hydrogen bond present forming an S(6) ring motif. In the crystal, pairs of O-H center dot center dot center dot O hydrogen bonds link adjacent molecules into inversion dimers with an R-2(2)(18) ring motif. The dimers are linked by very weak pi-pi interactions, forming layers parallel to ((2) over bar 01). Hirshfeld surface analysis, two-dimensional fingerprint plots and the molecular electrostatic potential surfaces were used to analyse the intermolecular interactions, indicating that the most important contributions for the crystal packing are from H center dot center dot center dot H (55.2%), C center dot center dot center dot H/H center dot center dot center dot C (22.3%) and O center dot center dot center dot H/H center dot center dot center dot O (13.6%) interactions.