Crystal structure of 4,4'-di-bromo-2',5'-dimeth-oxy-[1,1'-biphen-yl]-2,5-dione (BrHBQBr)

Joseph E Meany; Steven P Kelley; Robert M Metzger; Robin D Rogers; Stephen A Woski

doi:10.1107/S2056989015020472

Crystal structure of 4,4'-di-bromo-2',5'-dimeth-oxy-[1,1'-biphen-yl]-2,5-dione (BrHBQBr)

Acta Crystallogr E Crystallogr Commun. 2015 Nov 4;71(Pt 12):1454-6. doi: 10.1107/S2056989015020472. eCollection 2015 Dec 1.

Authors

Joseph E Meany¹, Steven P Kelley¹, Robert M Metzger¹, Robin D Rogers², Stephen A Woski¹

Affiliations

¹ Department of Chemistry, The University of Alabama, Box 870336, Tuscaloosa, AL 35487-0336, USA.
² Department of Chemistry, McGill University, 801 Sherbrooke St. West, Montreal, Quebec, Canada, H3A 0B8.

Abstract

In the title compound, C14H10Br2O4, the dihedral angle between the aromatic rings is 67.29 (19)°. Both meth-oxy-group C atoms lie close to the plane of their attached ring [deviations = -0.130 (4) and 0.005 (5) Å]. In the crystal, mol-ecules pack in a centrosymmetric fashion and inter-act via a mixture of weak π-π stacking inter-actions [centroid-centoid separations = 4.044 (2) and 4.063 (3) Å], weak C-H⋯O hydrogen bonding, and Br⋯Br halogen bonding. This induces a geometry quite different than that predicted by theory.

Keywords: Br⋯Br halogen bonding; crystal structure; hemibiquinone; hydrogen bonding; molecular rectifier; π–π stacking interactions.