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, Ai Ling Tan, David J. Young, Mukesh M. Jotani, A. Otero-De-La-Rozad, Edward R.T. Tiekink

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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)º. 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 π- π interactions. In the crystal, methylene-C-H···N(triazolyl) and carbonitrile- N···π(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.

Original languageEnglish
Pages (from-to)563-569
Number of pages7
JournalActa Crystallographica Section E: Crystallographic Communications
Issue numberPart 4
Publication statusPublished - 1 Apr 2016
Externally publishedYes


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