[Journal logo]

Volume 69 
Part 10 
Page o1496  
October 2013  

Received 11 July 2013
Accepted 26 August 2013
Online 4 September 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.007 Å
R = 0.044
wR = 0.135
Data-to-parameter ratio = 15.9
Details
Open access

4,6-Dibromo-N-{3-[(4,6-dibromo-2,3-dimethylphenyl)imino]butan-2-ylidene}-2,3-dimethylaniline

aKey Laboratory of Eco-Environment-Related Polymer Materials of the Ministry of Education, Key Laboratory of Polymer Materials of Gansu Province, College of Chemistry & Chemical Engineering, Northwest Normal University, Lanzhou 730070, People's Republic of China
Correspondence e-mail: clinton_du@126.com

The title compound, C20H20Br4N2, is a product of the condensation reaction of 4,6-dibromo-2,3-dimethylaniline and butane-2,3-dione. The molecule has a center of symmetry at the mid-point of the central C-C bond. The dihedral angle between the benzene ring and the 1,4-diazabutadiene plane is 78.3 (2)°. Niether hydrogen bonding nor aromatic stacking is observed in the crystal structure.

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.]). For related structures, see: Gao et al. (2012[Gao, H., Hu, H., Zhu, F. & Wu, Q. (2012). Chem. Commun. 48, 3312-3314.]); Sun et al. (2012[Sun, G. B., Hentschel, J. & Guan, Z. B. (2012). ACS Macro. Lett. 1, 585-588.]); Popeney et al. (2012[Popeney, C. S., Lukowiak, M. C., Böttcher, C., Schade, B., Welker, P., Mangoldt, D., Gunkel, G., Guan, Z. B. & Haag, R. (2012). ACS Macro. Lett. 1, 564-567.]); Shi et al. (2012[Shi, X., Zhao, Y., Gao, H., Zhang, L., Zhu, F. & Wu, Q. (2012). Macromol. Rapid Commun. 33, 374-379.]); Zhang & Ye (2012[Zhang, Z. & Ye, Z. (2012). Chem. Commun. 48, 7940-7942.]); Killian et al. (1996[Killian, C. M., Tempel, D., Johnson, L. K. & Brookhart, M. (1996). J. Am. Chem. Soc. 118, 11664-11665.]); Yuan et al. (2005[Yuan, J. C., Silva, L. C., Gomes, P. T., Campos, J. M., Riberio, M. R., Valerga, P. S., Chien, J. C. W. & Marques, M. M. (2005). Polymer, 46, 2122-2132.], 2011[Yuan, J. C., Mei, T. J., Gomes, P. T., Marques, M. M., Wang, X. H., Liu, Y. F., Miao, C. P. & Xie, X. L. (2011). J. Organomet. Chem. 696, 3251-3256.]).

[Scheme 1]

Experimental

Crystal data
  • C20H20Br4N2

  • Mr = 607.98

  • Monoclinic, P 21 /n

  • a = 5.5582 (6) Å

  • b = 12.8881 (15) Å

  • c = 14.8377 (11) Å

  • [beta] = 98.782 (8)°

  • V = 1050.43 (19) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 9.40 mm-1

  • T = 150 K

  • 0.29 × 0.17 × 0.16 mm

Data collection
  • Agilent SuperNova (Dual, Cu at zero, Eos) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013[Agilent (2013). CrysAlis PRO and CrysAlis RED. Agilent Technologies. Yarnton, England.]) Tmin = 0.688, Tmax = 1.000

  • 4675 measured reflections

  • 1921 independent reflections

  • 1777 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.135

  • S = 1.11

  • 1921 reflections

  • 121 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.70 e Å-3

  • [Delta][rho]min = -1.04 e Å-3

Data collection: CrysAlis PRO (Agilent, 2013[Agilent (2013). CrysAlis PRO and CrysAlis RED. Agilent Technologies. Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2013[Agilent (2013). CrysAlis PRO and CrysAlis RED. Agilent Technologies. Yarnton, England.]); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); program(s) used to refine structure: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); molecular graphics: OLEX2; software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2409 ).


Acknowledgements

We gratefully acknowledge the Natural Science Foundation of China (20702042, 21262028), the Program for Changjiang Scholars and Innovative Research Teams in Universities of the Ministry of Education of China (IRT1177), the Natural Science Foundation of Gansu Province (1208RJZA140) and the NWNU Young Teachers Reseach Improving Program (NWNU-LKQN-10-11) for financial support.

References

Agilent (2013). CrysAlis PRO and CrysAlis RED. Agilent Technologies. Yarnton, England.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Gao, H., Hu, H., Zhu, F. & Wu, Q. (2012). Chem. Commun. 48, 3312-3314.  [CSD] [CrossRef] [ChemPort]
Johnson, L. K., Killian, C. M. & Brookhart, M. (1995). J. Am. Chem. Soc. 117, 6414-6415.  [CrossRef] [ChemPort] [Web of Science]
Killian, C. M., Tempel, D., Johnson, L. K. & Brookhart, M. (1996). J. Am. Chem. Soc. 118, 11664-11665.  [CrossRef] [ChemPort] [Web of Science]
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Popeney, C. S., Lukowiak, M. C., Böttcher, C., Schade, B., Welker, P., Mangoldt, D., Gunkel, G., Guan, Z. B. & Haag, R. (2012). ACS Macro. Lett. 1, 564-567.  [CrossRef] [ChemPort]
Shi, X., Zhao, Y., Gao, H., Zhang, L., Zhu, F. & Wu, Q. (2012). Macromol. Rapid Commun. 33, 374-379.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Sun, G. B., Hentschel, J. & Guan, Z. B. (2012). ACS Macro. Lett. 1, 585-588.  [CrossRef] [ChemPort]
Yuan, J. C., Mei, T. J., Gomes, P. T., Marques, M. M., Wang, X. H., Liu, Y. F., Miao, C. P. & Xie, X. L. (2011). J. Organomet. Chem. 696, 3251-3256.  [CSD] [CrossRef] [ChemPort]
Yuan, J. C., Silva, L. C., Gomes, P. T., Campos, J. M., Riberio, M. R., Valerga, P. S., Chien, J. C. W. & Marques, M. M. (2005). Polymer, 46, 2122-2132.  [CSD] [CrossRef] [ChemPort]
Zhang, Z. & Ye, Z. (2012). Chem. Commun. 48, 7940-7942.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1496  [ doi:10.1107/S1600536813023921 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.