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

The title compounds, C23H21ClN2O2, differ from each other only by the position of the Cl atom on the corresponding benzene ring: meta relative to the central sp3 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. [ABSTRACT FROM AUTHOR]