Abstract
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 hy-droxy-phenyl 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 intra-molecular O-H⋯N and inter-molecular C-H⋯O hydrogen bonds, while in (II), intra-molecular O-H⋯N, C-H⋯N hydrogen bonds and weak inter-molecular C-H⋯π inter-actions are observed. Compound (I) was refined as an inversion twin.
Highlights
Salen-type Schiff bases possessing an unsymmetrical vicinal diamine backbone are promising candidates in synthetic and material science research. Salen ligands and their complexes are widely studied for their extensive applications in various fields, for their luminescent property (Chakraborty et al, 2015; Chen et al, 2013), photophysical properties (Cheng et al, 2013), NLO activity (Nayar & Ravikumar, 2014; Zeyrek, 2013)
In compounds (I) and (II), the molecular structure maybe influenced by two intramolecular O—H N hydrogen bonds (Tables 1 and 2)
The synthesis of the salen ligand 2-[(1E)-({1-(3-chlorophenyl)2-[(E)-(2-hydroxybenzylidene)amino]propyl}imino)methyl]phenol was achieved by the condensation of salicylaldehyde
Summary
Salen-type Schiff bases possessing an unsymmetrical vicinal diamine backbone are promising candidates in synthetic and material science research. Salen ligands and their complexes are widely studied for their extensive applications in various fields, for their luminescent property (Chakraborty et al, 2015; Chen et al, 2013), photophysical properties (Cheng et al., 2013), NLO activity (Nayar & Ravikumar, 2014; Zeyrek, 2013). In view of the importance of the title compounds, we have undertaken a single-crystal X-ray diffraction study and the results are presented here. Dashed lines represent intramolecular O—H N hydrogen bonds (Table 1).
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