Crystal structure and Hirshfeld surface analysis of (E)-2-{[(2-iodo-phen-yl)imino]-meth-yl}-6-methyl-phenol

Abstract

The title compound, C₁₄H₁₂INO, was synthesized by condensation of 2-hy-droxy-3-methyl-benzaldehyde and 2-iodo-aniline, and crystallizes in the ortho-rhom-bic space group P2₁2₁2₁. The 2-iodo-phenyl and benzene rings are twisted with respect to each other, making a dihedral angle of 31.38 (2)°. 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⋯π inter-actions, resulting in the formation of sheets along the a-axis direction. Within the sheets, very weak π-π stacking inter-actions lead to additional stabilization. The Hirshfeld surface analysis and fingerprint plots reveal that the crystal structure is dominated by H⋯H (37.1%) and C⋯H (30.1%) contacts. Hydrogen bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. The crystal studied was refined as a two-component inversion twin.

Keywords: 2-iodo­phen­yl; Hirshfeld surface analysis; Schiff base; crystal structure.