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

Manawar, Rohit B. and Gondaliya, Mitesh B. and Shah, Manish K. and Jotani, Mukesh M. and Tiekink, Edward R. T. * (2019) 2-{(1E)-[(E)-2-(2,6-Dichlorobenzylidene)hydrazin-1-ylidene]methyl}phenol: crystal structure, Hirshfeld surface analysis and computational study. Acta Crystallographica Section E Crystallographic Communications, 75 (10). pp. 1423-1428. ISSN 2056-9890 (In Press)

Tiekink 2 1E E 2 26 Dichlorobenzylidene Acta Cryst 2019 E75 1423.pdf - Accepted Version
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Official URL: http://doi.org/10.1107/S2056989019012349


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.

Item Type: Article
Uncontrolled Keywords: crystal structure; Schiff base; Hirshfeld surface analysis; computational chemistry.
Subjects: Q Science > QD Chemistry
Divisions: Others > Non Sunway Academics
Sunway University > School of Engineering and Technology [formerly School of Science and Technology until 2020] > Research Centre for Crystalline Materials moved to SMLS wef 2021
Depositing User: Dr Janaki Sinnasamy
Related URLs:
Date Deposited: 12 Sep 2019 09:32
Last Modified: 07 Oct 2020 08:31
URI: http://eprints.sunway.edu.my/id/eprint/1100

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