Crystal structure, Hirshfeld surface analysis and DFT study of N-(2-amino-5-methylphenyl)-2-(5-methyl-1H-pyrazol-3-yl)acetamide

Abstract

The title molecule, C13H16N4O, adopts an angular conformation. In the crystal a layer structure is generated by N—H...O and N—H...N hydrogen bonds together with C—H...π(ring) interactions. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H...H (53.8%), H...C/C...H (21.7%), H...N/N...H (13.6%), and H...O/O...H (10.8%) interactions. The optimized structure calculated using density functional theory (DFT) at the B3LYP/ 6–311 G(d,p) level is compared with the experimentally determined structure in the solid state. The calculated HOMO–LUMO energy gap is 5.0452 eV.

Coordination complexes constructed from pyrazole–acetamide and pyrazole–quinoxaline: effect of hydrogen bonding on the self-assembly process and antibacterial activity

“…In order to search for new ligand candidates for assemblies of metal complexes, we considered the case of pyrazole acetamide ligands with O and N donor atoms. 38–40 These molecules are particularly interesting as ligands for the construction of polynuclear complexes as models for bioinorganic systems. 41,42 As a continuation of our research along this line, 43,44 we have successfully synthesized three new Cd( ii ), Cu( ii ) and Fe( ii ) coordination complexes derived from the ligands, namely N -(2-aminophenyl)-2-(5-methyl-1 H -pyrazol-3-yl)acetamide (L 1 ) and 3-(5-methyl-1 H -pyrazol-3-yl)quinoxalin-2(1 H )-one (L 2 ) ( Fig.…”