Dimethyl 2,5-bis­(5-hexyl­thio­phen-2-yl)benzene-1,4-dioate

Song, C.-L.; Liu, K.; Zhang, A.-J.; Xu, Z.-G.; Zhang, H.-L.

doi:10.1107/S1600536811011718

Volume 67
Part 5
Page o1059
May 2011

Received 26 March 2011
Accepted 29 March 2011
Online 7 April 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.041
wR = 0.104
Data-to-parameter ratio = 15.1
Details

Dimethyl 2,5-bis(5-hexylthiophen-2-yl)benzene-1,4-dioate

Cheng-Li Song,^a Ke Liu,^a Ai-Jiang Zhang,^a Zhu-Guo Xu ^a ^* and Hao-Li Zhang ^a

^aState Key Laboratory of Applied Organic Chemistry (SKLAOC), College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, People's Republic of China
Correspondence e-mail: xuzhg@lzu.edu.cn

In the title compound, C₃₀H₃₈O₄S₂, the centroid of the benzene ring lies on a center of inversion. The thiophene ring is aligned at 49.8 (1)° with respect to the benzene ring. The alkyl chain adopts an extended zigzag conformation.

Related literature

The title compound and its derivatives are used in the preparation of organic semiconductors. For applications of these materials, see: Tian et al. (2010); Zhang et al. (2010). For the synthesis of related compounds, see: Fraind & Tovar (2010); Gurthrie & Tovar (2008), Hotta (2001); Kang et al. (1997); Lois et al. (2007); Shao & Zhao (2009); Zhao et al. (2007).

Experimental

Crystal data

C₃₀H₃₈O₄S₂
M_r = 526.72
Monoclinic, P 2/c
a = 15.617 (6) Å
b = 8.083 (3) Å
c = 11.585 (4) Å
= 104.470 (4)°
V = 1416.0 (9) Å³
Z = 2
Mo K radiation
= 0.22 mm^-1
T = 293 K
0.35 × 0.32 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.927, T_max = 0.959
6083 measured reflections
2490 independent reflections
1865 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.104
S = 1.04
2490 reflections
165 parameters
H-atom parameters constrained
_max = 0.16 e Å^-3
_min = -0.23 e Å^-3

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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: NG5141 ).

Acknowledgements

The authors are grateful for financial support from the National Natural Science Foundation of China (NSFC; 20872055, 21073079, J0730425) and the 111 project.

References

Bruker (2005). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Fraind, A. M. & Tovar, J. D. (2010). J. Phys. Chem. B, 114, 3104-3116.
Gurthrie, D. A. & Tovar, J. D. (2008). Org. Lett. 10, 4323-4326.
Hotta, S. (2001). J. Heterocycl. Chem. 38, 923-927.
Kang, S.-K., Kim, J.-S. & Choi, S.-C. (1997). J. Org. Chem. 62, 4208-4209.
Lois, S., Florès, J.-C., Lère-Porte, J.-P., Serein-Spirau, F., Moreau, J. J. E., Miqueu, K., Sotiropoulos, J.-M., Baylère, P., Tillard, M. & Belin, C. (2007). Eur. J. Org. Chem. 4019-4031.
Shao, M. & Zhao, Y. (2009). Tetrahedron Lett. 50, 6897-6900.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tian, H., Deng, Y., Pan, F., Huang, L., Yan, D., Geng, Y. & Wang, F. (2010). J. Mater. Chem. 20, 7998-8004.
Zhang, W., Smith, J., Watkins, S. E., Gysel, R., McGehee, M., Salleo, A., Kirkpatrick, J., Ashraf, S., Anthopoulos, T., Heeney, M. & McCulloch, I. (2010). J. Am. Chem. Soc. 132, 11437-11439.
Zhao, C., Zhang, Y. & Ng, M.-K. (2007). J. Org. Chem. 72, 6364-6371.

organic compounds