Crystal structure and Hirshfeld surface analysis of 4-azido-2-(3,5-dimethylphenyl)-5-(4-nitrophenyl)-2H-1,2,3-triazole

Abstract

In the title compound, C16H13N7O2, the 3,5-dimethylphenyl and 4-nitrophenyl rings are inclined to the central 2H-1,2,3-triazole ring by 1.80 (7) and 1.79 (7)°, respectively, and to one another by 2.16 (7)°. In the crystal, the molecules are linked by C—H...N hydrogen bonds and π–π stacking interactions [centroid-to-centroid distances = 3.7295 (9) and 3.7971 (9) Å], forming ribbons along the b-axis direction. These ribbons are connected to each other by weak van der Waals interactions and the stability of the crystal structure is ensured. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H...H (31.5%), N...H/H...N (19.2%), O...H/H...O (14.5%), N...C/C...C (10.9%) and C...H/H...C (10.2%) contacts.

Synthesis of new 2,5-diaryl 4-azido-derivatives of 2H-1,2,3-triazoles

“…The title compound was synthesized according to a literature protocol [4]. A 20 ml screw-neck vial was charged with DMSO (20 ml), dichlorodiazadiene (350 mg, 1 mmol) and sodium azide (NaN3; 390 mq; 3 mmol).…”

“…In our previous research, 4-azido 1,2,3-triazoles were synthesized by the reaction of dichlorodiazadienes with sodium azide (scheme 1). During these reactions, 4-azido-2H-1,2,3 was obtained as a result of intramolecular cyclization of (E)-1-(2,2-diazido-1-arylvinyl)-2aryldiazene, which was first obtained as an intermediate via nucleophilic substitution of chlorine atoms by azide groups [1][2][3][4]. The fact that the azide group is easily involved in substitution reactions in organic synthesis leads to their wide range of applications.…”