2-{(1E)-[(E)-2-(2,6-Di­chloro­benzyl­­idene)hydrazin-1-yl­­idene]meth­yl}phenol: crystal structure, Hirshfeld surface analysis and computational study

The title Schiff base compound, C14H10Cl2N2O, features an E configuration about each of the C=N imine bonds. Overall, the mol­ecule is approximately planar with the dihedral angle between the central C2N2 residue (r.m.s. deviation = 0.0371 Å) and the peripheral hy­droxy­benzene and chloro­benzene 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 intra­molecular hy­droxy-O—H⋯N(imine) hydrogen bond closes an S(6) loop. In the crystal, π–π stacking inter­actions between hy­droxy- and chloro­benzene rings [inter-centroid separation = 3.6939 (13) Å] lead to a helical supra­molecular chain propagating along the b-axis direction; the chains pack without directional inter­actions 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 inter­actions contribute 12.0% to the overall surface contacts. The calculation of the inter­action energies in the crystal indicates significant contributions from the dispersion term.