Crystal structure and Hirshfeld surface analysis of (E)-2-{[(2-iodophenyl)imino]methyl}-6-methylphenol

Abstract

The title compound, C14H12INO, was synthesized by condensation of 2-hydroxy-3-methylbenzaldehyde and 2-iodoaniline, and crystallizes in the orthorhombic space group P212121. The 2-iodophenyl and benzene rings are twisted with respect to each other, making a dihedral angle of 31.38 (2)°. The molecular structure is stabilized by an O—H...N hydrogen bond, forming an S(6) ring motif. In the crystal, molecules are linked by C—H...π interactions, resulting in the formation of sheets along the a-axis direction. Within the sheets, very weak π–π stacking interactions 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 interactions are the dominant interactions in the crystal packing. The crystal studied was refined as a two-component inversion twin.