Research Article: 4-Bromo-N-phenyl­aniline

Date Published: April 01, 2011

Publisher: International Union of Crystallography

Author(s): Emily J. Hefter, Joseph M. Tanski.


In the title compound, C12H10BrN, the dihedral angle between the benzene rings is 52.5 (1)°, 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 19.6 (2) and 36.2 (3)°. While the N—H group is not involved in hydrogen-bonding inter­actions, the structure exhibits a network of inter­molecular C—H⋯π and N—H⋯π inter­actions.

Partial Text

The 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: de Wit (2002 ▶); Lunder et al. (2010 ▶). For the synthesis, see: He et al. (2008 ▶); Sus (1947 ▶). For a related structure and information on C—H⋯π and N—H⋯π inter­actions, see: Krzymiński et al. (2009 ▶). For a description of the pitch angle in similar diphenyl structures, see: Duong & Tanski (2011 ▶); Lim & Tanski (2007 ▶).




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