TY - JOUR
T1 - 4-[(1-Benzyl-1H-1,2,3-triazol-4-yl)methoxy]benzene-1,2-dicarbonitrile
T2 - Crystal structure, Hirshfeld surface analysis and energy-minimization calculations
AU - Shamsudin, Norzianah
AU - Tan, Ai Ling
AU - Young, David J.
AU - Jotani, Mukesh M.
AU - Otero-De-La-Rozad, A.
AU - Tiekink, Edward R.T.
PY - 2016/4/1
Y1 - 2016/4/1
N2 - 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.
AB - 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.
KW - Conformation
KW - Crystal structure
KW - DFT
KW - Triazolyl
UR - http://www.scopus.com/inward/record.url?scp=84964034110&partnerID=8YFLogxK
U2 - 10.1107/S2056989016004722
DO - 10.1107/S2056989016004722
M3 - Article
AN - SCOPUS:84964034110
VL - E72
SP - 563
EP - 569
JO - Acta Crystallographica Section E: Crystallographic Communications
JF - Acta Crystallographica Section E: Crystallographic Communications
SN - 1600-5368
IS - Part 4
ER -