Methyl 3-[(1-benzyl-4-phenyl-1H-1,2,3-triazol-5-yl)formamido]propanoate: crystal structure, Hirshfeld surface analysis and computational chemistry

Abstract

The title compound, C20H20N4O3, is constructed about a tri-substituted 1,2,3-triazole ring, with the substituent at one C atom flanked by the C and N atoms being a substituted amide group, and with the adjacent C and N atoms bearing phenyl and benzyl groups, respectively; the dihedral angle between the pendant phenyl rings is 81.17 (12)°, indicative of an almost orthogonal disposition. In the crystal, pairwise amide-N—H...O(carbonyl) hydrogen bonds lead to a centrosymmetric dimer incorporating methylene-C—H...π(benzene) interactions. The dimers are linked into a supramolecular layer in the ab plane via methylene-C—H...N(azo) and benzene-C—H...O(amide) interactions; the layers stack along the c-axis direction without directional interactions between them. The above-mentioned intermolecular contacts are apparent in the analysis of the calculated Hirshfeld surface, which also provides evidence for short inter-layer H...C contacts with a significant dispersion energy contribution.

Keywords

• crystal structure
• 1,2,3-triazole
• hirshfeld surface analysis
• computational chemistry