1,4,5,8-Tetra­isopropyl­anthracene

Kitamura, C.; Tsukuda, H.; Kawase, T.; Kobayashi, T.; Naito, H.

doi:10.1107/S1600536810030837

Volume 66
Part 9
Page o2222
September 2010

Received 28 July 2010
Accepted 2 August 2010
Online 11 August 2010

Key indicators
Single-crystal X-ray study
T = 223 K
Mean (C-C) = 0.002 Å
R = 0.063
wR = 0.180
Data-to-parameter ratio = 23.1
Details

1,4,5,8-Tetraisopropylanthracene

Chitoshi Kitamura,^a ^* Hideki Tsukuda,^a Takeshi Kawase,^a Takashi Kobayashi ^b and Hiroyoshi Naito ^b

^aDepartment of Materials Science and Chemistry, Graduate School of Engineering, University of Hyogo, 2167 Shosha, Himeji, Hyogo 671-2280, Japan, and ^bDepartment of Physics and Electronics, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuencho, Naka-ku, Sakai, Osaka 599-8531, Japan
Correspondence e-mail: kitamura@eng.u-hyogo.ac.jp

The molecules of the title compound, C₂₆H₃₄, possess crystallographically imposed inversion symmetry. The anthracene ring system is planar within 0.038 (1) Å. The two methyl groups in each independent isopropyl group are oriented on either side of the anthracene plane. In the crystal structure, the molecules adopt a herringbone-like arrangement without [pi] - [pi] stacking.

Related literature

For the preparation and solid-state fluorescence studies of 1,4,5,8- tetraalkylanthracenes, see: Kitamura et al. (2007). For a related structure, see: Kitamura et al. (2010). For related herringbone structures, see: Curtis et al. (2004).

Experimental

Crystal data

C₂₆H₃₄
M_r = 346.53
Monoclinic, P 2₁ /c
a = 6.546 (3) Å
b = 10.357 (5) Å
c = 15.808 (8) Å
= 98.289 (8)°
V = 1060.5 (9) Å³
Z = 2
Mo K radiation
= 0.06 mm^-1
T = 223 K
0.50 × 0.07 × 0.05 mm

Data collection

Rigaku/MSC Mercury CCD area-detector diffractometer
Absorption correction: numerical (NUMABS; Higashi, 2000) T_min = 0.991, T_max = 0.996
9107 measured reflections
2817 independent reflections
1921 reflections with I > 2(I)
R_int = 0.043

Refinement

R[F² > 2(F²)] = 0.063
wR(F²) = 0.180
S = 1.07
2817 reflections
122 parameters
H-atom parameters constrained
_max = 0.28 e Å^-3
_min = -0.24 e Å^-3

Data collection: CrystalClear (Rigaku/MSC, 2006); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5142 ).

Acknowledgements

The authors thank the Instrument Center of the Institute for Molecular Science for the X-ray structural analysis. This work was supported by a Grant-in-Aid for Scientific Research (No. 20550128) from the Ministry of Education, Culture, Sports, Science and Technology, Japan.

References

Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.
Curtis, M. D., Cao, J. & Kampf, J. W. (2004). J. Am. Chem. Soc. 126, 4318-4328.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Higashi, T. (2000). NUMABS. Rigaku Corporation, Tokyo, Japan.
Kitamura, C., Abe, Y., Kawatsuki, N., Yoneda, A., Asada, K., Kobayashi, A. & Naito, H. (2007). Mol. Cryst. Liq. Cryst. 474, 119-135.
Kitamura, C., Tsukuda, H., Yoneda, A., Kawase, T., Kobayashi, A., Naito, H. & Komatsu, T. (2010). Eur. J. Org. Chem. pp. 3033-3040.
Rigaku/MSC (2006). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds