4-Bromo-N-(4-bromophenyl)aniline

Abstract

Key indicators: single-crystal X-ray study; T = 125 K; mean (C-C) = 0.003 Å; R factor = 0.026; wR factor = 0.064; data-to-parameter ratio = 24.3.In the title compound, C 12 H 9 Br 2 N, the dihedral angle between the benzene rings is 47.32 (5) , whereas the pitch angles, or the angles between the mean plane of each aryl group 'propeller blade' and the plane defined by the aryl bridging C-N-C angle, are 18.1 (2) and 31.7 (2) . No intermolecular N-H hydrogen bonding is present in the crystal; however, there is a short intermolecular BrÁ Á ÁBr contact of 3.568 (1) Å . Related literatureThe title compound is an amine analogue of brominated diphenyl ether flame retardant materials commonly used in household items. For information on environmental and health concerns related to brominated flame retardants, see:

4-Bromo-N-phenylaniline

“…For a related structure and information on C-HÁ Á Á and N-HÁ Á Á interactions, see: Krzymiń ski et al (2009). For a description of the pitch angle in similar diphenyl structures, see: Duong & Tanski (2011); Lim & Tanski (2007). Table 1 C-HÁ Á Á and N-HÁ Á Á interactions (Å , ).…”

“…The dihedral angle is found to be 52.5 (1)°, whereas the pitch angles are 19.6 (2)° and 36.2 (3)°. The pitch angles are the angles between the mean plane of each aryl group "propeller blade" and the plane defined by the three atoms C4-N1-C7 (Lim & Tanski, 2007;Duong & Tanski, 2011). In 4-methoxy-N-phenylaniline, the dihedral angle is somewhat larger, 59.9 (2)° (Krzymiński et al, 2009), whereas the pitch angles, 7.2° and 53.8°, are very different, exemplifying how analogous structures with similar dihedral angles may have dramatically different dispostions of the aryl groups about the bridging atom.…”