Crystal structure of 4′-bromo-2,3,5,6-tetra­fluoro­biphenyl-4-carbo­nitrile

The title compound, C(13)H(4)BrF(4)N, 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 P2(1)2(1)2(1). 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.