Title of article :
Crystal structure and spectroscopic properties of (E)-1,3-dimethyl-2-[3-(4-nitrophenyl)triaz-2-enylidene]-2,3-dihydro-1H-imidazole
Author/Authors :
Martinez, Hector Mario Heras Department of Chemistry & Physics - Florida Gulf Coast University, USA , Flores, David Chavez Facultad de Ciencias Químicas - Universidad Autónoma de Chihuahua - Nuevo Campus Universitario - Circuito Universitario, Mexico , Hillesheim, Patrick C. Department of Chemistry and Physics, USA , Patil, Siddappa Centre for Nano and Material Sciences - Jain University, Jain Global Campus, India , Bugarin, Alejandro Department of Chemistry & Physics - Florida Gulf Coast University, USA
Abstract :
The title compound (E)-1,3-dimethyl-2-[3-(4-nitrophenyl)triaz-2-enylidene]-2,3-dihydro-1H-imidazole, C11H12N6O2, has monoclinic (C2/c) symmetry at 100 K. This triazene derivative was synthesized by the coupling reaction of 1,3-dimethylimidazolium iodide with 1-azido-4-nitro benzene in the presence of sodium hydride (60% in mineral oil) and characterized by 1H NMR, 13C NMR, IR, mass spectrometry, and single-crystal X-ray diffraction. The molecule consists of six-membered and five-membered rings, which are connected by a triazene moiety (–N=N—N–). In the solid-state, the molecule is found to be planar due to conjugation throughout the molecule. The extended structure shows two layers of molecules, which present weak intermolecular interactions that facilitate the stacked arrangement of the molecules forming the extended structure. Furthermore, there are several weak pseudo-cyclical interactions between the nitro oxygen atoms and symmetry-adjacent H atoms, which help to arrange the molecules.
Keywords :
crystal structure , azides , π-conjugated triazenes , N-heterocyclic carbene
Journal title :
Acta Crystallographica Section E: Crystallographic Communications
