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

• Main Authors: Norzianah Shamsudin, Tan, Ai Ling, Young, David J., Jotani, Mukesh M., Otero-de-la-Roza, Alberto, Tiekink, Edward R. T. *
• Format: Article
• Language: English
• Published: International Union of Crystallography 2016
• Subjects: QD Chemistry
• Online Access: http://eprints.sunway.edu.my/642/1/Acta%20E_RC%202016%2072%20563.pdf; http://eprints.sunway.edu.my/642/; http://dx.doi.org/10.1107/S2056989016004722
• Institution: Sunway University

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.