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

Abstract

The title compound, C 14 H 12 ClNO 3 , 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-H···O hydrogen bond. In the crystal, pairs of centrosymmetrically related molecules are linked by O-H···O hydrogen bonds, forming R 22 (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%).