Received 10 March 2011
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 and N-H interactions.
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 and N-H interactions, see: Krzyminski et al. (2009). For a description of the pitch angle in similar diphenyl structures, see: Duong & Tanski (2011); Lim & Tanski (2007).
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and Mercury (Macrae et al., 2006).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: OM2415 ).
This work was supported by Vassar College. X-ray facilities were provided by the US National Science Foundation (grant No. 0521237 to JMT).
Bruker (2007). APEX2, SADABS and SAINT. BrukerAXS Inc., Madison, Wisconsin, USA.
Duong, M. M. & Tanski, J. M. (2011). Acta Cryst. E67, o755.
He, C., Chen, C., Cheng, J., Liu, C., Liu, W., Li, Q. & Lei, A. (2008). Angew. Chem. Int. Ed. 47, 6414-6417.
Krzyminski, K., Wera, M., Sikorski, A. & Blazejowski, J. (2009). Acta Cryst. E65, o152.
Lim, C. F. & Tanski, J. M. (2007). J. Chem. Crystallogr. 37, 587-595.
Lunder, S., Hovander, L., Athanassiadis, I. & Bergman, A. (2010). Environ. Sci. Technol. 44, 5256-5262.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sus, O. (1947). Annalen der Chemie 557, 237-242.
Wit, C. A. de (2002). Chemosphere, 46, 583-624.