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

Acta Crystallographica Section E: Crystallographic Communications

Schwarzer, A.¹  Weber, E.²  Heckel, R.²  Hulliger, J.³ 

[1] Department of Chemistry and Biochemistry, University of Berne, Freiestrasse 3, CH-3012 Berne, Switzerland;Institut für Organische Chemie, TU Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, Germany

关键词: CRYSTAL STRUCTURE;    BIPHENYL;    TETRAFLUORO SUBSTITUTION;    BROMO-CYANO SUBSTITUTION;    [PI]-[PI]F STACKING;    HALOGEN INTERACTIONS;   

DOI  :  10.1107/S2056989015007847

学科分类：数学（综合）

来源: International Union of Crystallography

【 摘 要 】

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.

【 授权许可】

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