(Z)-N-[(Z)-3-(2,4-Dimethyl­phenyl­imino)­butan-2-yl­idene]-2,4-dimethyl­aniline

Yuan, J.; Miao, C.; Xu, W.; Yuan, B.

doi:10.1107/S1600536811053244

Volume 68
Part 1
Page o164
January 2012

Received 15 November 2011
Accepted 10 December 2011
Online 17 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.052
wR = 0.175
Data-to-parameter ratio = 15.3
Details

(Z)-N-[(Z)-3-(2,4-Dimethylphenylimino)butan-2-ylidene]-2,4-dimethylaniline

Jianchao Yuan,^a ^* Chengping Miao,^a Weibing Xu ^a and Bingnian Yuan ^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

The asymmetric unit of the title compound, C₂₀H₂₄N₂, contains one half -molecule which exhibits a crystallographically imposed center of symmetry. The benzene rings are inclined to the 1,4-diazabutadiene mean plane by 78.3 (2)°.

Related literature

The title compound was synthesized as a [alpha] -diimine ligand for Ni^II- [alpha] -diimine olefin polymerization catalysts. For applications of [alpha] -diimine ligands, see: Johnson et al. (1995); Killian et al. (1996). For the design and synthesis of new [alpha] -diimine derivatives, see: Yuan et al. (2005); Popeney & Guan (2005, 2010); Popeney et al. (2011). The crystal structures of Re and Ni complexes with the title ligand were reported by Kia et al. (2005) and Yuan et al. (2011), respectively.

Experimental

Crystal data

C₂₀H₂₄N₂
M_r = 292.41
Orthorhombic, P b c a
a = 13.50 (1) Å
b = 7.571 (6) Å
c = 16.738 (12) Å
V = 1711 (2) Å³
Z = 4
Mo K radiation
= 0.07 mm^-1
T = 296 K
0.23 × 0.20 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.985, T_max = 0.991
5143 measured reflections
1592 independent reflections
1043 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.175
S = 1.05
1592 reflections
104 parameters
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.15 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: CV5204 ).

Acknowledgements

We thank the National Natural Science Foundation of China (grant No. 20964003) for funding. We also thank the Key Laboratory of Eco Environment-Related Polymer Materials of the Ministry of Education and Key Laboratory of Polymer Materials of Gansu Province (Northwest Normal University) for financial support.

References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Johnson, L. K., Killian, C. M. & Brookhart, M. (1995). J. Am. Chem. Soc. 117, 6414-6415.
Kia, R., Mirkhani, V., Deák, A. & Kálmán, A. (2005). Acta Cryst. E61, m566-m567.
Killian, C. M., Tempel, D. J., Johnson, L. K. & Brookhart, M. (1996). J. Am. Chem. Soc. 118, 11664-11665.
Popeney, C. S. & Guan, Z. B. (2005). Organometallics, 24, 1145-1155.
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.
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.
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