1-Chloro-4-[2-(4-chloro-phen-yl)eth-yl]benzene and its bromo analogue: crystal structure, Hirshfeld surface analysis and computational chemistry.

The crystal and mol-ecular structures of CHCl, (I), and CHBr, (II), are described. The asymmetric unit of (I) comprises two independent mol-ecules, and , each disposed about a centre of inversion. Each mol-ecule approximates mirror symmetry [the C-C-C-C torsion angles = -83.46 (19) and 95.17 (17)° for , and -83.7 (2) and 94.75 (19)° for ; b = benzene and e = ethyl-ene]. By contrast, the mol-ecule in (II) is twisted, as seen in the dihedral angle of 59.29 (11)° between the benzene rings . 0° in (I). The mol-ecular packing of (I) features benzene-C-H⋯π(benzene) and Cl⋯Cl contacts that lead to an open three-dimensional (3D) architecture that enables twofold 3D-3D inter-penetration. The presence of benzene-C-H⋯π(benzene) and Br⋯Br contacts in the crystal of (II) consolidate the 3D architecture. The analysis of the calculated Hirshfeld surfaces confirm the influence of the benzene-C-H⋯π(benzene) and ⋯ contacts on the mol-ecular packing and show that, to a first approximation, H⋯H, C⋯H/H⋯C and C⋯/⋯C contacts dominate the packing, each contributing about 30% to the overall surface in each of (I) and (II). The analysis also clearly differentiates between the and mol-ecules of (I).