N-H...N and C-H...π Interactions in 4-Amino-3-methyl-5-(p-Tolyl)-4H-1,2,4-Triazole and 4-Amino-3-methyl-5-Phenyl-4H-1,2,4-Triazole

Abstract

The title compounds, C<inf>10</inf>H<inf>12</inf>N<inf>4</inf>, (I), and C<inf>9</inf>H<inf>10</inf>N<inf>4</inf>, (II), have been synthesized and characterized both spectroscopically and structurally. The dihedral angles between the triazole and benzene ring planes are 26.59 (9) and 42.34 (2)°, respectively. In (I), molecules are linked principally by N-H⋯N hydrogen bonds involving the amino NH<inf>2</inf> group and a triazole N atom, forming R<inf>44</inf>(20) and R<inf>2</inf>4(10) rings which link to give a three-dimensional network of molecules. The hydrogen bonding is supported by two different C-H⋯π interactions from the tolyl ring to either a triazole ring or a tolyl ring in neighboring molecules. In (II), intermolecular hydrogen bonds and C-H⋯π interactions produce R <inf>3</inf>4(15) and R<inf>4</inf>4(21) rings. © 2006 International Union of Crystallography.