Crystal structures of salen-type ligands 2-[(1 E )-({1-(3-chlorophenyl)-2-[( E )-(2-hydroxybenzylidene)amino]propyl}imino)methyl]phenol and 2-[(1 E )-({1-(4-chlorophenyl)-2-[( E )-(2-hydroxybenzylidene)amino]propyl}imino)methyl]phenol

The title compounds, C 23 H 21 ClN 2 O 2 , differ from each other only by the position of the Cl atom on the corresponding benzene ring: meta relative to the central sp 3 C atom for (I) and para for (II). In (I), the hydroxyphenyl rings are almost parallel, the dihedral angle between the mean planes being 9.2 (2)°, but in (II), the relative position of the ring is different, characterized by a dihedral angle of 48.5 (1)°. Compound (I) features intramolecular O—H...N and intermolecular C—H...O hydrogen bonds, while in (II), intramolecular O—H...N, C—H...N hydrogen bonds and weak intermolecular C—H...π interactions are observed. Compound (I) was refined as an inversion twin.