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

• Main Authors: Manawar, Rohit B., Gondaliya, Mitesh B., Shah, Manish K., Jotani, Mukesh M., Tiekink, Edward R. T. *
• Format: Article
• Language: English
• Published: International Union of Crystallography 2019
• Subjects: QD Chemistry
• Online Access: http://eprints.sunway.edu.my/1100/1/Tiekink%202%201E%20E%202%2026%20Dichlorobenzylidene%20Acta%20Cryst%202019%20E75%201423.pdf; http://eprints.sunway.edu.my/1100/; http://doi.org/10.1107/S2056989019012349
• Institution: Sunway University

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 A˚ ) 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, – stacking interactions between hydroxy- and chlorobenzene rings [inter-centroid separation = 3.6939 (13) A˚ ] 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 – 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.