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(carbon-yl) hydrogen bonds lead to a centrosymmetric dimer incorporating methyl-ene-C-H⋯π(benzene) inter-actions. The dimers are linked into a supra-molecular layer in the ab plane via methyl-ene-C-H⋯N(azo) and benzene-C-H⋯O(amide) inter-actions; the layers stack along the c-axis direction without directional inter-actions between them. The above-mentioned inter-molecular 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.
Highlights
The title compound, C20H20N4O3, is constructed about a tri-substituted 1,2,3triazole 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
Pairwise amide-N—HÁ Á ÁO(carbonyl) hydrogen bonds lead to a centrosymmetric dimer incorporating methylene-C—HÁ Á Á(benzene) interactions
The dimers are linked into a supramolecular layer in the ab plane via methylene-C—HÁ Á ÁN(azo) and benzene-C—HÁ Á ÁO(amide) interactions; the layers stack along the c-axis direction without directional interactions between them
Summary
The title 1,2,3-triazole-5-carboxamide derivative, (I), was recently prepared and characterized from a palladium-catalysed aminocarbonylation reaction with the use of dimethyl carbonate as a sustainable solvent (de Albuquerque et al, 2019). There is a twist in the amide residue as seen in the value of the N4—C17—C18—C19 torsion angle of 73.6 (4), indicating a (+)syn-clinal relationship. This results in a dihedral angle close to orthogonal for the amide (C16,N4,O1) and carboxylate (C19,O2,O3) residues, i.e. 73.6 (4). The dimeric aggregates are connected into a supramolecular layer propagating in the ab plane via methylene-C3—HÁ Á ÁN2(azo) and benzene-C15— HÁ Á ÁO1(amide) interactions, Fig. 2(b). A more detailed analysis of the interactions occurring in the inter-layer region is provided by an analysis of the calculated Hirshfeld surfaces
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