Crystal structure and Hirshfeld surface analysis of 6,6'-((1 E,1' E)-{[1,4-phenyl-enebis(methyl-ene)]bis(aza-nylyl-idene)}bis-(methane-ylyl-idene))bis-(2-meth-oxy-phenol)

Abstract

The Schiff base compound, C₂₄H₂₄N₂O₄, was synthesized by the inter-action of 2-hy-droxy-3-meth-oxy benzaldehyde and 1,4-benzene dimethanamine in ethanol, and crystallizes in the monoclinic space group P2₁/n with Z' = 0.5. The mol-ecule is not planar, the 1,4-di-ethyl-benzene and the phenol rings are twisted with respect to each other, making a dihedral angle of 74.27 (5)°. The mol-ecular structure is stabilized by an O-H⋯N hydrogen bond, forming an S(6) ring motif. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, resulting in the formation of sheets parallel to the bc plane. A Hirshfeld surface analysis was undertaken to investigate the various inter-molecular contacts controlling the supra-molecular topology, suggesting the H⋯O (18%) contacts to be the most significant inter-actions, whereas the H⋯H (50.5%) and C⋯H (24.3%) inter-actions are less significant.

Keywords: Hirshfeld surface analysis; Schiff base; crystal structure; phenol–imine tautomer; tetra­dentate salen-type.