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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.
Highlights
Imines derived from o-hydroxy aromatic carbonyls are of interest because of their ability to form an asymmetric intramolecular hydrogen bond between the oxygen atom of the hydroxyl group and the nitrogen atom of the imine moiety (Dominiak et al, 2003)
Two types of intramolecular hydrogen bonds are observed in Schiff bases: O—HÁ Á ÁN in enol–imine and N—HÁ Á ÁO in keto–amine tautomers
The title compound, (I), is a Schiff base derivative from 2-hydroxy-3-methylbenzaldehyde, which crystallizes in the phenol–imine tautomeric form with an E configurationfor the imine functionality
Summary
Imines derived from o-hydroxy aromatic carbonyls are of interest because of their ability to form an asymmetric intramolecular hydrogen bond between the oxygen atom of the hydroxyl group and the nitrogen atom of the imine moiety (Dominiak et al, 2003). This ability has a decisive impact on the biological and thermo- or photochromic properties of ohydroxy aromatic Schiff bases and makes them very useful compounds in chemistry, biochemistry, medicine, and technology (Vlad et al, 2018; Bouhidel et al, 2018; Faizi et al, 2020a,b). The crystal and molecular structures of the title compound, along with the results of a Hirshfeld surface analysis
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Schedule a callMore From: Acta crystallographica. Section E, Crystallographic communications
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