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

Yuan, J.; Xu, W.; Mei, T.; Liu, Y.; Wang, X.

doi:10.1107/S1600536811052044

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 (C-C) = 0.003 Å
R = 0.039
wR = 0.115
Data-to-parameter ratio = 15.6
Details

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

Jianchao Yuan,^a ^* Weibing Xu,^a Tongjian Mei,^a Yufeng Liu ^a and Xuehu Wang ^a

^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); Killian et al. (1996). For the effect of the ligand structure on the activity of the catalyst and properties of the products, see: Popeney & Guan (2010); Popeney et al. (2011); Yuan et al. (2005). For related structures, see: Kose & McKee (2011); Wei et al. (2011).

Experimental

Crystal data

C₁₈H₁₈Cl₂N₂
M_r = 333.24
Monoclinic, P 2₁ /n
a = 8.032 (6) Å
b = 7.372 (5) Å
c = 14.475 (10) Å
= 93.533 (7)°
V = 855.5 (11) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.918, T_max = 0.932
5279 measured reflections
1588 independent reflections
1199 reflections with I > 2(I)
R_int = 0.034

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.115
S = 1.06
1588 reflections
102 parameters
H-atom parameters constrained
_max = 0.22 e Å^-3
_min = -0.28 e Å^-3

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); 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.

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.
Killian, C. M., Tempel, D. J., Johnson, L. K. & Brookhart, M. (1996). J. Am. Chem. Soc. 118, 11664-11665.
Kose, M. & McKee, V. (2011). Acta Cryst. E67, o3193.
Popeney, C. S. & Guan, Z. B. (2010). Macromolecules, 43, 4091-4097.
Popeney, C. S., Levins, C. M. & Guan, Z. B. (2011). Organometallics, 30, 2432-2452.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wei, T.-B., Lu, Y.-Y., Cao, C., Yao, H. & Zhang, Y.-M. (2011). Acta Cryst. E67, o1833.
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.

organic compounds