Crystal structure and Hirshfeld surface analysis of a Schiff base: (Z)-6-[(5-chloro-2-methoxyanilino)-methylidene]-2-hydroxycyclohexa-2,4-dien-1-one.

The title compound, C14H12ClNO3, is a Schiff base that exists in the keto–enamine tautomeric form and adopts a Z configuration. In the crystal, the dihedral angle between the planes of the benzene rings is 5.34 (15)°. The roughly planar geometry of the mol­ecule is stabilized by a strong intra­molecular N—HO hydrogen bond. In the crystal, pairs of centrosymmetrically related mol­ecules are linked by O—H···O hydrogen bonds, forming R2²(10) rings. Besides this, the mol­ecules form stacks along the [001] direction with C—H···π and C—H···Cl contacts between the stacks. The inter­molecular inter­actions in the crystal were analysed using Hirshfeld surfaces. The most significant contribution to the crystal packing is from H···H contacts (30.8%). [ABSTRACT FROM AUTHOR]