Abstract
The title Schiff base compound, C14H10Cl2N2O, features an E configuration about each of the C=N imine bonds. Overall, the mol-ecule is approximately planar with the dihedral angle between the central C2N2 residue (r.m.s. deviation = 0.0371 Å) and the peripheral hy-droxy-benzene and chloro-benzene rings being 4.9 (3) and 7.5 (3)°, respectively. Nevertheless, a small twist is evident about the central N-N bond [the C-N-N-C torsion angle = -172.7 (2)°]. An intra-molecular hy-droxy-O-H⋯N(imine) hydrogen bond closes an S(6) loop. In the crystal, π-π stacking inter-actions between hy-droxy- and chloro-benzene rings [inter-centroid separation = 3.6939 (13) Å] lead to a helical supra-molecular chain propagating along the b-axis direction; the chains pack without directional inter-actions between them. The calculated Hirshfeld surfaces point to the importance of H⋯H and Cl⋯H/H⋯Cl contacts to the overall surface, each contributing approximately 29% of all contacts. However, of these only Cl⋯H contacts occur at separations less than the sum of the van der Waals radii. The aforementioned π-π stacking inter-actions contribute 12.0% to the overall surface contacts. The calculation of the inter-action energies in the crystal indicates significant contributions from the dispersion term.
Highlights
Being deprotonable and readily substituted with various residues, Schiff base molecules are prominent as multidentate ligands for the generation of a wide variety of metal complexes
A key motivation for studies in this area arises from our interest in the Schiff bases themselves and of their metal complexes, which are well-known to possess a wide spectrum of biological activity against disease-causing microorganisms (Tian et al, 2009; 2011)
The most prominent supramolecular association in the crystal of (I) are – stacking interactions. These occur between the hydroxy- and chlorobenzene rings with an inter-centroid separation = 3.6939 (13) Aand angle of inclination =
Summary
Being deprotonable and readily substituted with various residues, Schiff base molecules are prominent as multidentate ligands for the generation of a wide variety of metal complexes. A key motivation for studies in this area arises from our interest in the Schiff bases themselves and of their metal complexes, which are well-known to possess a wide spectrum of biological activity against disease-causing microorganisms (Tian et al, 2009; 2011). Over and beyond biological considerations, Schiff bases are suitable for the development of non-linear optical materials because of their solvato-chromaticity (Labidi, 2013). As a part of complementary structural studies on these molecules, the crystal and molecular structures of (I) are described together with a detailed analysis of the calculated Hirshfeld surfaces
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