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

ABSTRACT: The crystal and mol-ecular structures of C14H12Cl2, (I), and C14H12Br2, (II), are described. The asymmetric unit of (I) comprises two independent mol-ecules, A and B, each disposed about a centre of inversion. Each mol-ecule approximates mirror symmetry [the Cb-Cb-Ce-Ce torsion angles = -83.46?(19) and 95.17?(17)° for A, and -83.7?(2) and 94.75?(19)° for B; 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 cf. 0° in (I). The mol-ecular packing of (I) features benzene-C-H??(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??(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??(benzene) and X?X contacts on the mol-ecular packing and show that, to a first approximation, H?H, C?H/H?C and C?X/X?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 A and B mol-ecules of (I).

SUBMITTER: Jotani MM 

PROVIDER: S-EPMC6505616 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature