Crystal structure of 4,4′-dibromo-2′,5′-dimethoxy-[1,1′-biphenyl]-2,5-dione (BrHBQBr)

Abstract

In the title compound, C14H10Br2O4, the dihedral angle between the aromatic rings is 67.29 (19)°. Both methoxy-group C atoms lie close to the plane of their attached ring [deviations = −0.130 (4) and 0.005 (5) Å]. In the crystal, molecules pack in a centrosymmetric fashion and interact via a mixture of weak π–π stacking interactions [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

• crystal structure
• molecular rectifier
• hemibiquinone
• π–π stacking interactions
• hydrogen bonding
• Br...Br halogen bonding