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 ?-? inter-actions. In the crystal, methyl-ene-C-H?N(triazol-yl) and carbo-nitrile-N??(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.

SUBMITTER: Shamsudin N 

PROVIDER: S-EPMC4910342 | biostudies-literature | 2016 Apr

REPOSITORIES: biostudies-literature