4-Bromo-N-phenyl­aniline

Hefter, E.J.; Tanski, J.M.

doi:10.1107/S160053681101052X

Volume 67
Part 4
Page o976
April 2011

Received 10 March 2011
Accepted 21 March 2011
Online 26 March 2011

Key indicators
Single-crystal X-ray study
T = 125 K
Mean (C-C) = 0.004 Å
R = 0.043
wR = 0.118
Data-to-parameter ratio = 24.1
Details

4-Bromo-N-phenylaniline

Emily J. Hefter ^a and Joseph M. Tanski ^a ^*

^aDepartment of Chemistry, Vassar College, Poughkeepsie, NY 12604, USA
Correspondence e-mail: jotanski@vassar.edu

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 [pi] and N-H [pi] interactions.

Related literature

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 [pi] and N-H [pi] interactions, see: Krzyminski et al. (2009). For a description of the pitch angle in similar diphenyl structures, see: Duong & Tanski (2011); Lim & Tanski (2007).

Experimental

Crystal data

C₁₂H₁₀BrN
M_r = 248.12
Orthorhombic, P c c n
a = 15.6741 (6) Å
b = 17.7531 (7) Å
c = 7.3608 (3) Å
V = 2048.24 (14) Å³
Z = 8
Mo K radiation
= 3.97 mm^-1
T = 125 K
0.31 × 0.21 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker 2007) T_min = 0.373, T_max = 0.857
31081 measured reflections
3137 independent reflections
2552 reflections with I > 2(I)
R_int = 0.038

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.118
S = 1.07
3137 reflections
130 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 1.72 e Å^-3
_min = -0.77 e Å^-3

Table 1
C-H [pi] and N-H [pi] interactions (Å, °)

Cg1 and Cg2 are the centroids of the C1-C6 and C7-C12 rings, respectively.

D-HA	D-H	HA	DA	D-HA
C6-H6Cg2ⁱ	0.95	2.69	3.404 (3)	132
N1-H1Cg1ⁱⁱ	0.85 (2)	2.65	3.501 (2)	175
C9-H9Cg1ⁱⁱⁱ	0.95	2.96	3.651 (3)	131
Symmetry codes: (i) x, y, z-1; (ii) $[x-{\script{1\over 2}}, y+{\script{3\over 2}}, -z]$ ; (iii) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+2]$ .

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 ).

Acknowledgements

This work was supported by Vassar College. X-ray facilities were provided by the US National Science Foundation (grant No. 0521237 to JMT).

References

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.

organic compounds