Crystal structure and Hirshfeld surface analysis of (E)-1-(4-chloro-phen-yl)-2-[2,2-di-chloro-1-(4-fluoro-phen-yl)ethen-yl]diazene

Abstract

In the title compound, C₁₄H₈Cl₃FN₂, the planes of the 4-fluoro-phenyl ring and the 4-chloro-phenyl ring make a dihedral angle of 56.13 (13)°. In the crystal, mol-ecules are stacked in a column along the a axis via a weak C-H⋯Cl hydrogen bond and face-to-face π-π stacking inter-actions [centroid-centroid distances = 3.8615 (18) and 3.8619 (18) Å]. The crystal packing is further stabilized by short Cl⋯Cl contacts. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from Cl⋯H/H⋯Cl (31.2%), H⋯H (14.8%), C⋯H/H⋯C (14.0%), F⋯H/H⋯F (12.8%), C⋯C (9.0%) and Cl⋯Cl (6.7%) inter-actions.

Keywords: 4-chloro­phen­yl; 4-fluoro­phen­yl; Hirshfeld surface analysis; crystal structure; face-to-face π-π stacking inter­action.