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Volume 69 
Part 2 
Page o199  
February 2013  

Received 13 December 2012
Accepted 30 December 2012
Online 9 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.009 Å
R = 0.052
wR = 0.113
Data-to-parameter ratio = 15.0
Details
Open access

(E)-4-Bromo-N-{(E)-3-[(4-bromo-2-methylphenyl)imino]butan-2-ylidene}-2-methylaniline

aKey Laboratory of Environmental Materials and Engineering of Jiangsu Province, Yangzhou University, Yangzhou 225009, People's Republic of China
Correspondence e-mail: zhangxu@yzu.edu.cn

The title compound, C18H18Br2N2, is centrosymmetric with the mid-point of the central C-C bond of the butyl group located on an inversion center. The terminal benzene ring is approximately perpendicular to the central butyl plane [dihedral angle = 71.9 (8)°]. No hydrogen bonding or aromatic stacking is observed in the crystal.

Related literature

For applications of diimine-metal catalysts, see: Johnson et al. (1995[Johnson, L. K., Killian, C. M. & Brookhart, M. (1995). J. Am. Chem. Soc. 117, 6414-6415.]); Killian et al. (1996[Killian, C. M., Tempel, D. J., Johnson, L. K. & Brookhart, M. (1996). J. Am. Chem. Soc. 118, 11664-11665.]); Popeney & Guan (2010[Popeney, C. S. & Guan, Z. B. (2010). Macromolecules, 43, 4091-4097.]); Popeney et al. (2011[Popeney, C. S., Levins, C. M. & Guan, Z. B. (2011). Organometallics, 30, 2432-2452.]); Yuan et al. (2005[Yuan, J.-C., Silva, L. C., Gomes, P. T., Valerga, P., Campos, J. M., Ribeiro, M. R., Chien, J. C. W. & Marques, M. M. (2005). Polymer, 46, 2122-2132.]). For a related structure, see: Zhang et al. (2013[Zhang, C., Wu, G.-F., Huang, B.-M. & Lu, X.-Q. (2013). Acta Cryst. E69, o216.]).

[Scheme 1]

Experimental

Crystal data
  • C18H18Br2N2

  • Mr = 422.16

  • Orthorhombic, P b c a

  • a = 13.625 (13) Å

  • b = 7.495 (7) Å

  • c = 17.029 (17) Å

  • V = 1739 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 4.66 mm-1

  • T = 293 K

  • 0.21 × 0.20 × 0.15 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.441, Tmax = 0.542

  • 6368 measured reflections

  • 1541 independent reflections

  • 847 reflections with I > 2[sigma](I)

  • Rint = 0.104

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.113

  • S = 1.05

  • 1541 reflections

  • 103 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.70 e Å-3

  • [Delta][rho]min = -0.85 e Å-3

Data collection: APEX2 (Bruker, 2007[Bruker (2007). SAINT and APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SAINT and APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5666 ).


References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). SAINT and APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Johnson, L. K., Killian, C. M. & Brookhart, M. (1995). J. Am. Chem. Soc. 117, 6414-6415.  [CrossRef] [ChemPort] [ISI]
Killian, C. M., Tempel, D. J., Johnson, L. K. & Brookhart, M. (1996). J. Am. Chem. Soc. 118, 11664-11665.  [CrossRef] [ChemPort] [ISI]
Popeney, C. S. & Guan, Z. B. (2010). Macromolecules, 43, 4091-4097.  [ISI] [CrossRef] [ChemPort]
Popeney, C. S., Levins, C. M. & Guan, Z. B. (2011). Organometallics, 30, 2432-2452.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Yuan, J.-C., Silva, L. C., Gomes, P. T., Valerga, P., Campos, J. M., Ribeiro, M. R., Chien, J. C. W. & Marques, M. M. (2005). Polymer, 46, 2122-2132.  [CSD] [CrossRef] [ChemPort]
Zhang, C., Wu, G.-F., Huang, B.-M. & Lu, X.-Q. (2013). Acta Cryst. E69, o216.  [CrossRef] [details]


Acta Cryst (2013). E69, o199  [ doi:10.1107/S1600536812052087 ]

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