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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 [sigma](C-C) = 0.003 Å
R = 0.052
wR = 0.175
Data-to-parameter ratio = 15.3
Details
Open access

(Z)-N-[(Z)-3-(2,4-Dimethylphenylimino)butan-2-ylidene]-2,4-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: 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 NiII-[alpha]-diimine olefin polymerization catalysts. For applications of [alpha]-diimine ligands, 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 design and synthesis of new [alpha]-diimine derivatives, see: 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.]); Popeney & Guan (2005[Popeney, C. S. & Guan, Z. B. (2005). Organometallics, 24, 1145-1155.], 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.]). The crystal structures of Re and Ni complexes with the title ligand were reported by Kia et al. (2005[Kia, R., Mirkhani, V., Deák, A. & Kálmán, A. (2005). Acta Cryst. E61, m566-m567.]) and Yuan et al. (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.]), respectively.

[Scheme 1]

Experimental

Crystal data
  • C20H24N2

  • Mr = 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[alpha] radiation

  • [mu] = 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[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.985, Tmax = 0.991

  • 5143 measured reflections

  • 1592 independent reflections

  • 1043 reflections with I > 2[sigma](I)

  • Rint = 0.031

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

  • wR(F2) = 0.175

  • S = 1.05

  • 1592 reflections

  • 104 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT 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: 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.  [CrossRef] [ChemPort] [ISI]
Kia, R., Mirkhani, V., Deák, A. & Kálmán, A. (2005). Acta Cryst. E61, m566-m567.  [CSD] [CrossRef] [details]
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. (2005). Organometallics, 24, 1145-1155.  [CrossRef] [ChemPort]
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., 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., 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, o164  [ doi:10.1107/S1600536811053244 ]

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