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

Wang, L.; Luo, X.; Gao, B.; Wu, Q.; Mu, Y.

doi:10.1107/S1600536811052901

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 (C-C) = 0.003 Å
R = 0.053
wR = 0.151
Data-to-parameter ratio = 16.2
Details

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

Li Wang,^a Xuyang Luo,^b Bo Gao,^a Qiaolin Wu ^a ^* and Ying Mu ^a ^*

^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-HN 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); Hagar et al. (2010); Kovach et al. (2011); Oleinik et al. (2005); Ragaini et al. (2006); Rosa et al. (2008); Small et al. (2007); Zhou et al. (2008).

Experimental

Crystal data

C₃₂H₃₂N₂
M_r = 444.60
Monoclinic, C 2/c
a = 13.5134 (12) Å
b = 8.6952 (8) Å
c = 22.3532 (19) Å
= 99.413 (1)°
V = 2591.2 (4) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.984, T_max = 0.986
7599 measured reflections
2538 independent reflections
1842 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.053
wR(F²) = 0.151
S = 1.02
2538 reflections
157 parameters
H-atom parameters constrained
_max = 0.42 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C4-H4N1ⁱ	0.95	2.43	3.379 (2)	179
Symmetry code: (i) x, y+1, z.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); 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: 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.
Kovach, J., Peralta, M., Brennessel, W. W. & Jones, W. D. (2011). J. Mol. Struct. 992, 33-38.
Li, L.-D., Gomes, C. S. B., Gomes, P. T., Duarte, M. T. & Fan, Z. Q. (2011). Dalton Trans. 40, 3365-3380.
Oleinik, I. I., Oleinik, I. V., Ivanchev, S. S. & Tolstikov, G. A. (2005). Russ. J. Org. Chem. 41, 1354-1357.
Ragaini, F., Gasperini, M., Parma, P., Gallo, E., Casati, N. & Macchi, P. (2006). New J. Chem. 30, 1046-1057.
Rosa, V., Aviles, T., Aullon, G., Covelo, B. & Lodeiro, C. (2008). Inorg. Chem. 47, 7734-7744.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Small, B. L., Rios, R., Fernandez, E. R. & Carney, M. J. (2007). Organometallics, 26, 1744-1749.
Zhou, J., Sun, H.-J., Harms, K. & Sundermeyer, J. (2008). Z. Anorg. Allg. Chem. 634, 1517-1521.

organic compounds