4,4′-Bipyridine-1,1′-diium bis­(1,3-benzo­thia­zole-2-thiol­ate)

Jiang, Y.-H.; Qiu, Q.-M.; Liu, M.; Jin, Q.-H.; Zhang, C.-L.

doi:10.1107/S1600536812047058

Volume 68
Part 12
Page o3450
December 2012

Received 2 September 2012
Accepted 15 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.008 Å
R = 0.060
wR = 0.203
Data-to-parameter ratio = 14.6
Details

4,4'-Bipyridine-1,1'-diium bis(1,3-benzothiazole-2-thiolate)

Yu-Han Jiang,^a Qi-Ming Qiu,^a Min Liu,^b Qiong-Hua Jin ^a ^* and Cun-Lin Zhang ^c

^aDepartment of Chemistry, Capital Normal University, Beijing 100048, People's Republic of China,^bThe College of Materials Science and Engineering, Beijing University of Technology, Beijing 100022, People's Republic of China, and ^cKey Laboratory of Terahertz Optoelectronics, Ministry of Education, Department of Physics, Capital Normal University, Beijing 100048, People's Republic of China
Correspondence e-mail: jinqh204@163.com

In the title salt, C₁₀H₁₀N₂²⁺·2C₇H₄NS₂^-, the complete 4,4'-bipyridine-1,1'-diium dication is generated by a center of symmetry. In the crystal, N-HN hydrogen bonds are observed between the cations and anions.

Related literature

For ligands based on 2-mercaptobenzothiazole in coordination chemistry, see: Chen et al. (2010) and for ligands based on 4,4'- bipyridine, see: Biradha et al. (1999); Ren et al. (2004); Tao et al. (2000); Tong et al. (2000); Xu et al. (2012). For a related structure, see: Deng et al. (2005).

Experimental

Crystal data

C₁₀H₁₀N₂²⁺·2C₇H₄NS₂^-
M_r = 490.66
Monoclinic, P 2₁ /c
a = 14.3909 (13) Å
b = 5.6670 (4) Å
c = 15.5471 (14) Å
= 109.023 (2)°
V = 1198.67 (17) Å³
Z = 2
Mo K radiation
= 0.42 mm^-1
T = 298 K
0.32 × 0.30 × 0.26 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007) T_min = 0.878, T_max = 0.900
5663 measured reflections
2116 independent reflections
990 reflections with I > 2(I)
R_int = 0.055

Refinement

R[F² > 2(F²)] = 0.060
wR(F²) = 0.203
S = 1.04
2116 reflections
145 parameters
H-atom parameters constrained
_max = 0.29 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2N1ⁱ	0.86	1.93	2.790 (6)	178
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus; 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: JJ2151 ).

Acknowledgements

This work was supported by National Natural Science Foundation of China (No.21171119), the National High Technology Research and Development Program 863 of China (No. 2012 A A063201), Beijing Personnel Bureau, the National Keystone Basic Research Program (973 Program) under grant Nos. 2007CB310408 and 2006CB302901 and the Committee of Education of the Beijing Foundation of China (grant No. KM201210028020).

References

Biradha, K., Domasevitch, K. V., Moulton, B., Seward, C. & Zaworotko, M. J. (1999). Chem. Commun. pp. 1327-1328.
Bruker (2007). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, S. C., Yu, R. M., Zhao, Z. G., Chen, S. M., Zhang, Q. S., Wu, X. Y., Wang, F. & Lu, C. Z. (2010). Cryst. Growth Des. 10, 1155-1160.
Deng, Q.-J., Yao, M.-X. & Zeng, M.-H. (2005). Acta Cryst. E61, o2239-o2240.
Ren, C.-X., Cheng, L., Chen, X.-M. & Ng, S. W. (2004). Acta Cryst. E60, m364-m366.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tao, J., Tong, M. L., Shi, J. X., Chen, X. M. & Ng, S. W. (2000). Chem. Commun. pp. 2043-2044.
Tong, M. L., Zheng, S. L. & Chen, X. M. (2000). Polyhedron, 19, 1809-1814.
Xu, S., Dai, Y.-C., Qiu, Q.-M., Jin, Q.-H. & Zhang, C.-L. (2012). Acta Cryst. E68, m1222-m1223.

organic compounds