R. Heckel, J. Hulliger, A. Schwarzer
Apr 25, 2015
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Journal
Acta Crystallographica Section E: Crystallographic Communications
Abstract
The title compound, C13H4BrF4N, synthesized from 1,4′-bromoiodobenzene and 4-bromo-2,3,5,6-tetrafluorobenzonitrile in a coupling reaction was found to crystallize in the orthorhombic space group P212121. The two phenyl rings are rotated with respect to each other by 40.6 (6)°. The molecules interact via aryl–perfluoroaryl stacking [3.796 (2) and 3.773 (2) Å], resulting in intermolecular chains along the a-axis direction. C—H⋯F contacts of about 2.45 Å connect these chains. In contrast to the structure of the parent compound 4′-bromobiphenyl-4-carbonitrile, CN⋯Br contacts that could have given rise to a linear arrangement of the biphenyl molecules desirable for non-linear optical (NLO) materials are not observed in the packing. Instead, several Br⋯F [3.2405 (17) and 3.2777 (18) Å] and F⋯F [2.894 (2) Å] contacts of side-on type II form an intermolecular network of zigzag chains. The crystal studied was refined as an inversion twin.