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

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)°. The molecular structure is stabilized by an intramolecular N—H...O hydrogen bond forming an S(6) ring motif. In the crystal, inversion-related molecules are linked by pairs of O—H...O hydrogen bonds, forming dimers with an R 2 2(18) ring motif. The dimers are linked by pairs of C—H...O contacts with an R 2 2(10) ring motif, forming ribbons extended along the [2\overline{1}0] 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...H (33.9%), O...H/H...O (29.8%) and C...H/H...C (17.3%) interactions.