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Volume 68 
Part 1 
Page o210  
January 2012  

Received 14 November 2011
Accepted 15 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.006 Å
R = 0.059
wR = 0.211
Data-to-parameter ratio = 14.8
Details
Open access

(E)-N-{(E)-2-[(3,5-Dimethylbiphenyl-4-yl)imino]acenaphthen-1-ylidene}-2,6-dimethyl-4-phenylaniline

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 title compound, C40H32N2, has crystallographic twofold rotation symmetry, with two C atoms lying on the axis. The dihedral angle between the two benzene rings of the 4-phenyl-2,6-dimethylphenyl group is 35.74 (17)°. The acenaphthene ring makes an angle of 76.93 (11)° with the benzene ring bonded to the N atom and an angle of 41.53 (13)° with the other benzene ring.

Related literature

The title compound was synthesized as an [alpha]-diimine ligand for use in NiII-[alpha]-diimine olefin polymerization catalysts. For applications of metal-organic polymerization 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.]); Popeney et al. (2005[Popeney, C. & Guan, Z. B. (2005). Organometallics, 24, 1145-1155.], 2010[Popeney, C. S. & Guan, Z. B. (2010). Macromolecules, 43, 4091-4097.], 2011[Popeney, C. S., Levins, C. M. & Guan, Z. B. (2011). Organometallics, 30, 2432-2452.]). For a related structure, see: Lohr et al. (2011[Lohr, T. L., Piers, W. E. & Parvez, M. (2011). Acta Cryst. E67, o2280.]).

[Scheme 1]

Experimental

Crystal data
  • C40H32N2

  • Mr = 540.68

  • Monoclinic, C 2/c

  • a = 22.994 (14) Å

  • b = 8.676 (5) Å

  • c = 18.652 (18) Å

  • [beta] = 124.084 (4)°

  • V = 3082 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 296 K

  • 0.23 × 0.21 × 0.19 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008a[Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.]) Tmin = 0.985, Tmax = 0.987

  • 10667 measured reflections

  • 2857 independent reflections

  • 1596 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.059

  • wR(F2) = 0.211

  • S = 1.16

  • 2857 reflections

  • 193 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Data collection: APEX2 (Bruker, 2008[Bruker (2008). SAINT and APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). SAINT and APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008b[Sheldrick, G. M. (2008b). 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: FY2034 ).


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 the Ministry of Education, Key Laboratory of Polymer Materials of Gansu Province (Northwest Normal University), for financial support.

References

Bruker (2008). SAINT and APEX2. 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]
Lohr, T. L., Piers, W. E. & Parvez, M. (2011). Acta Cryst. E67, o2280.  [CSD] [CrossRef] [details]
Popeney, C. & 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. (2008a). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o210  [ doi:10.1107/S1600536811054092 ]

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