Crystal structure and spectroscopic properties of (E)-1,3-di­methyl-2-[3-(4-nitro­phen­yl)triaz-2-enyl­­idene]-2,3-di­hydro-1H-imidazole

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.