title: 4-[(1-Benzyl-1H-1,2,3-triazol-4-yl)meth-oxy]benzene-1,2-dicarbo-nitrile: crystal structure, Hirshfeld surface analysis and energy-minimization calculations.
abstract: In the solid state, the title compound, C18H13N5O, adopts a conformation whereby the phenyl ring and meth-oxy-benzene-1,2-dicarbo-nitrile 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 intra-molecular π-π inter-actions. In the crystal, methyl-ene-C-H⋯N(triazol-yl) and carbo-nitrile-N⋯π(benzene) inter-actions lead to supra-molecular chains along the a axis. Supra-molecular layers in the ab plane arise as the chains are connected by benzene-C-H⋯N(carbo-nitrile) inter-actions; layers stack with no directional inter-actions between them. The specified inter-molecular contacts along with other, weaker contributions to the supra-molecular stabilization are analysed in a Hirshfeld surface analysis.
authors.affiliation: Faculty of Science, Universiti Brunei Darussalam, Jalan Tungku Link BE 1410, Negara Brunei Darussalam.
authors.forename: Norzianah
authors.initials: N
authors.lastname: Shamsudin
authors.affiliation: Faculty of Science, Universiti Brunei Darussalam, Jalan Tungku Link BE 1410, Negara Brunei Darussalam.
authors.forename: Ai Ling
authors.initials: AL
authors.lastname: Tan
authors.affiliation: Faculty of Science, Health, Education and Engineering, University of the Sunshine Coast, Maroochydore DC, Queensland 4558, Australia.
authors.forename: David J
authors.initials: DJ
authors.lastname: Young
authors.affiliation: Department of Physics, Bhavan's Sheth R. A. College of Science, Ahmedabad, Gujarat 380 001, India.
authors.forename: Mukesh M
authors.initials: MM
authors.lastname: Jotani
authors.affiliation: National Institute for Nanotechnology, National Research Council of Canada, 11421 Saskatchewan Drive, Edmonton, Alberta, T6G 2M9, Canada; Department of Chemistry, University of British Columbia, Okanagan, 3247 University Way, Kelowna, British Columbia, V1V 1V7, Canada.
authors.forename: A
authors.initials: A
authors.lastname: Otero-de-la-Roza
authors.affiliation: Research Centre for Crystalline Materials, Faculty of Science and Technology, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia.
authors.forename: Edward R T
authors.initials: ER
authors.lastname: Tiekink
keywords: DFT; Hirshfeld surface; conformation; crystal structure; triazol­yl