Crystal structure and Hirshfeld surface analysis of (E)-1-(4-chlorophenyl)-2-(2,2-dibromo-1-(3-nitrophenyl)vinyl)diazene

Abstract

The molecule of the title compound, C14H8Br2ClN3O2, consists of three almost planar groups: the central dibromoethenyldiazene fragment and two attached aromatic rings. The mean planes of these rings form dihedral angles with the plane of the central fragment of 17.00 (13) and 60.91 (13)0 for chlorine- and nitro-substituted rings, respectively. In the crystal, face-to-face π-π stacking interactions connect molecules in zig-zag chains along the a-axis. With halogen⋅⋅⋅halogen, halogen⋅⋅⋅hydrogen, Br⋅⋅⋅H, O⋅⋅⋅H, N⋅⋅⋅H and van der Waals interactions between these chains, molecular packing becomes stable. The most substantial contributions to crystal packing, according to a Hirshfeld surface analysis, are from Br⋅⋅⋅H/H⋅⋅⋅Br (19.6%), H⋅⋅⋅H (12.2%), C⋅⋅⋅H/H⋅⋅⋅C (11.9%) and O⋅⋅⋅H/H⋅⋅⋅O (11.0%) contacts.