4-[(1-Benzyl-1H-1,2,3-triazol-4-yl)meth­oxy]benzene-1,2-dicarbo­nitrile: crystal structure, Hirshfeld surface analysis and energy-minimization calculations

N Shamsudin; A L Tan; David James Young; Mukesh M Jotani; A Otero-de-la-Roza; Edward R T Tiekink

doi:10.1107/S2056989016004722

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4-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methoxy]benzene-1,2-dicarbonitrile: crystal structure, Hirshfeld surface analysis and energy-minimization calculations

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4-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methoxy]benzene-1,2-dicarbonitrile: crystal structure, Hirshfeld surface analysis and energy-minimization calculations

N Shamsudin, A L Tan, David James Young, Mukesh M Jotani, A Otero-de-la-Roza and Edward R T Tiekink

Acta Crystallographica Section E: Crystallographic Communications, Vol.72, pp.563-569

2016

DOI: https://doi.org/10.1107/S2056989016004722

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Abstract

crystal structure

triazolyl

conformation

DFT

Hirshfeld surface

In the solid state, the title compound, C18H13N5O, adopts a conformation whereby the phenyl ring and methÂoxy-benzene-1,2-dicarboÂnitrile residue (r.m.s. deviation of the 12 non-H atoms = 0.041 Ã…) lie to opposite sides of the central triazolyl ring, forming dihedral angles of 79.30 (13) and 64.59 (10)°, respectively; the dihedral angle between the outer rings is 14.88 (9)°. This conformation is nearly 7 kcal mol-1 higher in energy than the energy-minimized structure which has a syn disposition of the outer rings, enabling intraÂmolecular [pi]-[pi] interÂactions. In the crystal, methylÂene-C-H...N(triazolÂyl) and carboÂnitrile-N...[pi](benzene) interÂactions lead to supraÂmolecular chains along the a axis. SupraÂmolecular layers in the ab plane arise as the chains are connected by benzene-C-H...N(carboÂnitrile) interÂactions; layers stack with no directional interÂactions between them. The specified interÂmolecular contacts along with other, weaker contributions to the supraÂmolecular stabilization are analysed in a Hirshfeld surface analysis.

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Title: 4-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methoxy]benzene-1,2-dicarbonitrile: crystal structure, Hirshfeld surface analysis and energy-minimization calculations
Authors: N Shamsudin (Author) - Universiti Brunei Darussalam, Brunei Darussalam
A L Tan (Author) - Universiti Brunei Darussalam, Brunei Darussalam
David James Young (Author) - University of the Sunshine Coast - Faculty of Science, Health, Education and Engineering
Mukesh M Jotani (Author) - Bhavan's Sheth R A College of Science, India
A Otero-de-la-Roza (Author) - National Research Council of Canada, Canada
Edward R T Tiekink (Author) - Sunway University, Malaysia
Publication details: Acta Crystallographica Section E: Crystallographic Communications, Vol.72, pp.563-569
Publisher: Wiley-Blackwell Publishing Inc.
Date published: 2016
DOI: 10.1107/S2056989016004722
ISSN: 2056-9890
Copyright note: Copyright © 2016 The Authors. For information about this journal please refer to the journal's website. All articles published in Acta Crystallographica Section E are open access and distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. See http://creativecommons.org/licenses/by/2.0/uk/legalcode
Organisation Unit: University of the Sunshine Coast, Queensland
Language: English
Record Identifier: 99449138302621
Output Type: Journal article

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