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Volume 68 
Part 1 
Page o62  
January 2012  

Received 14 November 2011
Accepted 2 December 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.039
wR = 0.115
Data-to-parameter ratio = 15.6
Details
Open access

(Z)-3-Chloro-N-[(Z)-3-(3-chloro-2-methylphenylimino)butan-2-ylidene]-2-methylaniline

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: jianchaoyuan@nwnu.edu.cn

In the title compound, C18H18Cl2N2, the complete molecule is generated by the application of C2 symmetry. The C=N bond has an E configuration. The dihedral angle between the benzene ring and the 1,4-diazabutadiene plane is 66.81 (9)°.

Related literature

For background to the applications of the olefin polymerization Ni(II)-[alpha]-diimine 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.]). For the effect of the ligand structure on the activity of the catalyst and properties of the products, see: 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., SiIva, 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 related structures, see: Kose & McKee (2011[Kose, M. & McKee, V. (2011). Acta Cryst. E67, o3193.]); Wei et al. (2011[Wei, T.-B., Lu, Y.-Y., Cao, C., Yao, H. & Zhang, Y.-M. (2011). Acta Cryst. E67, o1833.]).

[Scheme 1]

Experimental

Crystal data
  • C18H18Cl2N2

  • Mr = 333.24

  • Monoclinic, P 21 /n

  • a = 8.032 (6) Å

  • b = 7.372 (5) Å

  • c = 14.475 (10) Å

  • [beta] = 93.533 (7)°

  • V = 855.5 (11) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.38 mm-1

  • T = 296 K

  • 0.23 × 0.21 × 0.19 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SAINT, APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.918, Tmax = 0.932

  • 5279 measured reflections

  • 1588 independent reflections

  • 1199 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.115

  • S = 1.06

  • 1588 reflections

  • 102 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Data collection: APEX2 (Bruker, 2008[Bruker (2008). SAINT, APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). SAINT, APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2319 ).


Acknowledgements

We thank the National Natural Science Foundation of China (20964003) for funding. We also thank the Key Laboratory of Eco Environment-Related Polymer Materials of Ministry of Education, Key Laboratory of Polymer Materials of Gansu Province (Northwest Normal University), for financial support

References

Bruker (2008). SAINT, APEX2 and SADABS. 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]
Kose, M. & McKee, V. (2011). Acta Cryst. E67, o3193.  [CrossRef] [details]
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]
Wei, T.-B., Lu, Y.-Y., Cao, C., Yao, H. & Zhang, Y.-M. (2011). Acta Cryst. E67, o1833.  [CSD] [CrossRef] [details]
Yuan, J. C., SiIva, 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]


Acta Cryst (2012). E68, o62  [ doi:10.1107/S1600536811052044 ]

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