4-(4-Acetyl-5-methyl-1H-1,2,3-triazol-1-yl)benzonitrile: crystal structure and Hirshfeld surface analysis

Abstract

The title compound, C12H10N4O, comprises a central 1,2,3-triazole ring (r.m.s. deviation = 0.0030 Å) flanked by N-bound 4-cyanophenyl and C-bound acetyl groups, which make dihedral angles of 54.64 (5) and 6.8 (3)° with the five-membered ring, indicating a twisted molecule. In the crystal, the three-dimensional architecture is sustained by carbonyl-C=O...π(triazoyl), cyano-C[triple-bond]N...π(triazoyl) (these interactions are shown to be attractive based on non-covalent interaction plots) and π–π stacking interactions [intercentroid separation = 3.9242 (9) Å]. An analysis of the Hirshfeld surface shows the important contributions made by H...H (35.9%) and N...H (26.2%) contacts to the overall surface, as well as notable contributions by O...H (9.9%), C...H (8.7%), C...C (7.3%) and C...N (7.2%) contacts.

Keywords

• crystal structure
• 1,2,3-triazol-1-yl
• nitrile
• Hirshfeld surface analysis
• NCI plots