[Journal logo]

Volume 68 
Part 1 
Page o128  
January 2012  

Received 9 November 2011
Accepted 8 December 2011
Online 14 December 2011

Key indicators
Single-crystal X-ray study
T = 185 K
Mean [sigma](C-C) = 0.003 Å
R = 0.053
wR = 0.151
Data-to-parameter ratio = 16.2
Details
Open access

N,N'-Bis(2,6-diethylphenyl)acenaphthylene-1,2-diimine

aState Key Laboratory of Supramolecular Structure and Materials, School of Chemistry, Jilin University, Changchun 130012, People's Republic of China, and bSchool of Chemistry, Jilin University, Changchun 130012, People's Republic of China
Correspondence e-mail: wuql@jlu.edu.cn, ymu@jlu.edu.cn

The title compound, C32H32N2, has crystallographic twofold rotation symmetry, with two C atoms lying on the rotation axis. The dihedral angle between the substituted benzene ring and the naphthalene ring system is 79.8 (1)°. The crystal structure is stabilized by C-H...N interactions, which form a chain motif along the b-axis direction.

Related literature

For details and applications of acenaphthenquinone-based Schiff bases and corresponding metal complexes, see: Li et al. (2011[Li, L.-D., Gomes, C. S. B., Gomes, P. T., Duarte, M. T. & Fan, Z. Q. (2011). Dalton Trans. 40, 3365-3380.]); Hagar et al. (2010[Hagar, M., Ragaini, F., Monticelli, E., Caselli, A., Macchi, P. & Casati, N. (2010). Chem. Commun. 46, 6153-6155.]); Kovach et al. (2011[Kovach, J., Peralta, M., Brennessel, W. W. & Jones, W. D. (2011). J. Mol. Struct. 992, 33-38.]); Oleinik et al. (2005[Oleinik, I. I., Oleinik, I. V., Ivanchev, S. S. & Tolstikov, G. A. (2005). Russ. J. Org. Chem. 41, 1354-1357.]); Ragaini et al. (2006[Ragaini, F., Gasperini, M., Parma, P., Gallo, E., Casati, N. & Macchi, P. (2006). New J. Chem. 30, 1046-1057.]); Rosa et al. (2008[Rosa, V., Aviles, T., Aullon, G., Covelo, B. & Lodeiro, C. (2008). Inorg. Chem. 47, 7734-7744.]); Small et al. (2007[Small, B. L., Rios, R., Fernandez, E. R. & Carney, M. J. (2007). Organometallics, 26, 1744-1749.]); Zhou et al. (2008[Zhou, J., Sun, H.-J., Harms, K. & Sundermeyer, J. (2008). Z. Anorg. Allg. Chem. 634, 1517-1521.]).

[Scheme 1]

Experimental

Crystal data
  • C32H32N2

  • Mr = 444.60

  • Monoclinic, C 2/c

  • a = 13.5134 (12) Å

  • b = 8.6952 (8) Å

  • c = 22.3532 (19) Å

  • [beta] = 99.413 (1)°

  • V = 2591.2 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 185 K

  • 0.25 × 0.24 × 0.21 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.984, Tmax = 0.986

  • 7599 measured reflections

  • 2538 independent reflections

  • 1842 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.151

  • S = 1.02

  • 2538 reflections

  • 157 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C4-H4...N1i 0.95 2.43 3.379 (2) 179
Symmetry code: (i) x, y+1, z.

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART and SAINT. 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: FY2033 ).


Acknowledgements

We thank the National Natural Science Foundation of China (grant Nos. 21004026 and 21074043).

References

Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Hagar, M., Ragaini, F., Monticelli, E., Caselli, A., Macchi, P. & Casati, N. (2010). Chem. Commun. 46, 6153-6155.  [CSD] [CrossRef] [ChemPort]
Kovach, J., Peralta, M., Brennessel, W. W. & Jones, W. D. (2011). J. Mol. Struct. 992, 33-38.  [ISI] [CSD] [CrossRef] [ChemPort]
Li, L.-D., Gomes, C. S. B., Gomes, P. T., Duarte, M. T. & Fan, Z. Q. (2011). Dalton Trans. 40, 3365-3380.  [CSD] [CrossRef] [ChemPort] [PubMed]
Oleinik, I. I., Oleinik, I. V., Ivanchev, S. S. & Tolstikov, G. A. (2005). Russ. J. Org. Chem. 41, 1354-1357.  [ISI] [CrossRef]
Ragaini, F., Gasperini, M., Parma, P., Gallo, E., Casati, N. & Macchi, P. (2006). New J. Chem. 30, 1046-1057.  [ISI] [CSD] [CrossRef] [ChemPort]
Rosa, V., Aviles, T., Aullon, G., Covelo, B. & Lodeiro, C. (2008). Inorg. Chem. 47, 7734-7744.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Small, B. L., Rios, R., Fernandez, E. R. & Carney, M. J. (2007). Organometallics, 26, 1744-1749.  [CrossRef] [ChemPort]
Zhou, J., Sun, H.-J., Harms, K. & Sundermeyer, J. (2008). Z. Anorg. Allg. Chem. 634, 1517-1521.  [CSD] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o128  [ doi:10.1107/S1600536811052901 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.