Crystal structure and Hirshfeld surface analysis of (Z)-6-(2-hy­droxy-5-nitro­anilino)methyl­idene-4-methyl­cyclo­hexa-24-dien-1-one

摘要

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 [20] 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.