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 A˚ ) and the peripheral hydroxybenzene and chlorobenzene ring...
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International Union of Crystallography
2019
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my.sunway.eprints.11002020-10-07T08:31:28Z http://eprints.sunway.edu.my/1100/ 2-{(1E)-[(E)-2-(2,6-Dichlorobenzylidene)hydrazin-1-ylidene]methyl}phenol: crystal structure, Hirshfeld surface analysis and computational study Manawar, Rohit B. Gondaliya, Mitesh B. Shah, Manish K. Jotani, Mukesh M. Tiekink, Edward R. T. * QD Chemistry 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. International Union of Crystallography 2019-09-04 Article PeerReviewed text en cc_by_nc_4 http://eprints.sunway.edu.my/1100/1/Tiekink%202%201E%20E%202%2026%20Dichlorobenzylidene%20Acta%20Cryst%202019%20E75%201423.pdf 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) http://doi.org/10.1107/S2056989019012349 doi:10.1107/S2056989019012349 |
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QD Chemistry Manawar, Rohit B. Gondaliya, Mitesh B. Shah, Manish K. Jotani, Mukesh M. Tiekink, Edward R. T. * 2-{(1E)-[(E)-2-(2,6-Dichlorobenzylidene)hydrazin-1-ylidene]methyl}phenol: crystal structure, Hirshfeld surface analysis and computational study |
| description |
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. |
| format |
Article |
| author |
Manawar, Rohit B. Gondaliya, Mitesh B. Shah, Manish K. Jotani, Mukesh M. Tiekink, Edward R. T. * |
| author_facet |
Manawar, Rohit B. Gondaliya, Mitesh B. Shah, Manish K. Jotani, Mukesh M. Tiekink, Edward R. T. * |
| author_sort |
Manawar, Rohit B. |
| title |
2-{(1E)-[(E)-2-(2,6-Dichlorobenzylidene)hydrazin-1-ylidene]methyl}phenol: crystal structure, Hirshfeld surface analysis and computational study |
| title_short |
2-{(1E)-[(E)-2-(2,6-Dichlorobenzylidene)hydrazin-1-ylidene]methyl}phenol: crystal structure, Hirshfeld surface analysis and computational study |
| title_full |
2-{(1E)-[(E)-2-(2,6-Dichlorobenzylidene)hydrazin-1-ylidene]methyl}phenol: crystal structure, Hirshfeld surface analysis and computational study |
| title_fullStr |
2-{(1E)-[(E)-2-(2,6-Dichlorobenzylidene)hydrazin-1-ylidene]methyl}phenol: crystal structure, Hirshfeld surface analysis and computational study |
| title_full_unstemmed |
2-{(1E)-[(E)-2-(2,6-Dichlorobenzylidene)hydrazin-1-ylidene]methyl}phenol: crystal structure, Hirshfeld surface analysis and computational study |
| title_sort |
2-{(1e)-[(e)-2-(2,6-dichlorobenzylidene)hydrazin-1-ylidene]methyl}phenol: crystal structure, hirshfeld surface analysis and computational study |
| publisher |
International Union of Crystallography |
| publishDate |
2019 |
| url |
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 |
| _version_ |
1680323411120750592 |
| score |
13.211869 |