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

Norzianah Shamsudin, and Tan, Ai Ling and Young, David J. and Jotani, Mukesh M. and Otero-de-la-Roza, Alberto and Tiekink, Edward R. T. * (2016) 4-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methoxy]benzene-1,2-dicarbonitrile: crystal structure, Hirshfeld surface analysis and energy-minimization calculations. Acta Crystallographica Section E Crystallographic Communications, 72 (4). pp. 563-569. ISSN 2056-9890

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Official URL: http://dx.doi.org/10.1107/S2056989016004722


In the solid state, the title compound, C18H13N5O, adopts a conformation whereby the phenyl ring and meth­oxy-benzene-1,2-dicarbo­nitrile residue (r.m.s. deviation of the 12 non-H atoms = 0.041 Å) 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 intra­molecular [pi]-[pi] inter­actions. In the crystal, methyl­ene-C-H...N(triazol­yl) and carbo­nitrile-N...[pi](benzene) inter­actions lead to supra­molecular chains along the a axis. Supra­molecular layers in the ab plane arise as the chains are connected by benzene-C-H...N(carbo­nitrile) inter­actions; layers stack with no directional inter­actions between them. The specified inter­molecular contacts along with other, weaker contributions to the supra­molecular stabilization are analysed in a Hirshfeld surface analysis.

Item Type: Article
Additional Information: First and 2nd authors are with Faculty of Science, Universiti Brunei Darussalam; 3rd author is Faculty of Science, Health, Education and Engineering, University of the Sunshine Coast; 4th author is with Department of Physics, Bhavan’s Sheth R. A. College of Science, Ahmedabad; 5th author is with National Institute for Nanotechnology, National Research Council of Canada, and Department of Chemistry, University of British Columbia; 6th author is with fResearch Centre for Crystalline Materials, Faculty of Science and Technology, Sunway University
Uncontrolled Keywords: crystal structure; triazolyl; conformation; DFT; Hirshfeld surface
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: Ms. Molly Chuah
Related URLs:
Date Deposited: 31 Oct 2017 03:41
Last Modified: 07 Oct 2020 09:55
URI: http://eprints.sunway.edu.my/id/eprint/642

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