Crystal Structure and Hirshfeld Surface Analysis of (E)-2

Abstract

The title compound, C14H12INO, was synthesized by condensation of 2-hydroxy-3-methylbenzaldehyde and 2-iodoaniline, and crystallizes in the orthorhombic space group P2(1)2(1)2(1). The 2-iodophenyl and benzene rings are twisted with respect to each other, making a dihedral angle of 31.38 (2)degrees. The molecular structure is stabilized by an O-H center dot center dot center dot N hydrogen bond, forming an S(6) ring motif. In the crystal, molecules are linked by C-H center dot center dot center dot pi interactions, resulting in the formation of sheets along the a-axis direction. Within the sheets, very weak pi-pi stacking interactions lead to additional stabilization. The Hirshfeld surface analysis and fingerprint plots reveal that the crystal structure is dominated by H center dot center dot center dot H (37.1%) and C center dot center dot center dot 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.