Abstract
The asymmetric unit of the title compound, C16H14Cl2N2O, comprises two similar mol-ecules, A and B, in which the dihedral angles between the two aromatic rings are 70.1 (3) and 73.2 (2)°, respectively. The crystal structure features short C-H⋯Cl and C-H⋯O contacts and C-H⋯π and van der Waals inter-actions. The title compound was refined as a two-component non-merohedral twin, BASF 0.1076 (5). The Hirshfeld surface analysis and two-dimensional fingerprint plots show that H⋯H (38.2% for mol-ecule A; 36.0% for mol-ecule B), Cl⋯H/H⋯Cl (24.6% for mol-ecule A; 26.7% for mol-ecule B) and C⋯H/H⋯C (20.0% for mol-ecule A; 20.2% for mol-ecule B) inter-actions are the most important contributors to the crystal packing.
Highlights
The Hirshfeld surface analysis and twodimensional fingerprint plots show that HÁ Á ÁH (38.2% for molecule A; 36.0% for molecule B), ClÁ Á ÁH/HÁ Á ÁCl (24.6% for molecule A; 26.7% for molecule B) and CÁ Á ÁH/HÁ Á ÁC (20.0% for molecule A; 20.2% for molecule B) interactions are the most important contributors to the crystal packing
In molecule B, the N4/N3/C18/C17/Cl3/Cl4 moiety is approximately planar with a maximum deviation of 0.046 (6) A, and makes dihedral angles of 9.57 (18) and 75.94 (19), respectively, with the C19–C24 and C26–C31 rings
Cg2, Cg3 and Cg4 are the centroids of the benzene rings C10–C15 and C19–C24 and C26–C31, respectively
Summary
Azo dyes have found a wide range of applications, including as ligands, sensors, optical data storage, liquid crystals, non-linear optical materials, color-changing materials, molecular switches, and dye-sensitized solar cells (Maharramov et al, 2018; Mahmudov et al, 2016; Viswanathan et al, 2019). The functional properties of azo dyes are strongly dependent on the groups attached to the –N N– synthon. Noncovalent bond donors or acceptors attached to N-donor azo/ hydrazone ligands are of interest because of their high solubility in polar solvents, functional properties, photoactivity in the solid state, coordination ability, and high thermal and oxidative stability (Gurbanov et al, 2020a,b; Kopylovich et al, 2011; Mac Leod et al, 2012; Mahmoudi et al, 2017a,b, 2018a,b). The functionalization of N-donor ligands with –COOH or –SO3H groups can improve the catalytic activity of the corresponding metal complexes in oxidation and C—C coupling reactions (Gurbanov et al, 2018; Ma et al, 2017a,b, 2020, 2021; Mahmudov et al, 2013; Mizar et al, 2012; Shixaliyev et al, 2014). In the current work we have synthesized a new azo dye, (E)-1-[2,2-dichloro-1-(4-methylphenyl)ethenyl]-2-(4-methoxyphenyl)diazene, which displays multiple intermolecular non-covalent interactions
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