Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hydroxy-5-nitroanilino)methylidene]-4-methylcyclohexa-2,4-dien-1-one

Abstract

The title compound, C14H12N2O4, is a Schiff base that exists in the keto-enamine tautomeric form and adopts a Z configuration. The molecule is almost planar, the rings making a dihedral angle of 4.99 (7)degrees. The molecular structure is stabilized by an intramolecular N-H center dot center dot center dot O hydrogen bond forming an S(6) ring motif. In the crystal, inversion-related molecules are linked by pairs of O-H center dot center dot center dot O hydrogen bonds, forming dimers with an R-2(2)(18) ring motif. The dimers are linked by pairs of C-H center dot center dot center dot O contacts with an R-2(2)(10) ring motif, forming ribbons extended along the [2 (1) over bar0] direction. Hirshfeld surface analysis, two-dimensional fingerprint plots and the molecular electrostatic potential surfaces were used to analyse the intermolecular interactions present in the crystal, indicating that the most important contributions for the crystal packing are from H center dot center dot center dot H (33.9%), O center dot center dot center dot H/H center dot center dot center dot O (29.8%) and C center dot center dot center dot H/H center dot center dot center dot C (17.3%) interactions.