The crystal structure of 2′,6′-dichloro-4-dimethylaminoazobenzene

A monoazo dye, 2′,6′-dichloro-4-dimethylaminoazobenzene (C14H13Cl2N3) was synthesized and characterized by X-ray diffraction, IR, 1H NMR, and elemental analysis. The title molecule crystallizes in the monoclinic system space group P21/c (#14), a = 10.782(1), b = 8.9610(9), c = 15.108(2) Å, β = 103.008(5)°, V = 1422.2(3) Å3, Z = 4. The title molecule is not planar and takes trans-geometry and the two phenyl rings are twisted around the central linkage in opposite directions. In the crystal, molecules are interacted through π⋯π interaction, forming ‘double chains’ along [1 −1 0]. The ‘double chains’ are extended along [001] through H-Bond C11–H6⋯Cl2, C5–H3⋯Cl1 forming double layers (110), which are in turn interacted by C3–H1⋯Cl1 H-Bond [010], forming crystals. The molecular geometry has been calculated using the ab initio restricted Hartree–Fock and density functional method (B3LYP) with 6-311G** basis set. The optimized geometric parameters obtained by two methods are similar and in good agreement with the experimental values.