4,4′-Bipyridine–3,3′-disulfanediyl­bis­(1H-1,2,4-triazole-5-amine) (1/1)

Yang, W.; Qiu, Q.-M.; Jin, Q.-H.; Zhang, C.-L.

doi:10.1107/S1600536812042742

Volume 68
Part 11
Page o3194
November 2012

Received 15 August 2012
Accepted 12 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R = 0.043
wR = 0.106
Data-to-parameter ratio = 12.6
Details

4,4'-Bipyridine-3,3'-disulfanediylbis(1H-1,2,4-triazole-5-amine) (1/1)

Wei Yang,^a Qi-Ming Qiu,^a Qiong-Hua Jin ^a ^* and Cun-Lin Zhang ^b

^aDepartment of Chemistry, Capital Normal University, Beijing 100048, People's Republic of China, and ^bKey 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 1:1 adduct, C₁₀H₈N₂·C₄H₆N₈S₂·, the components are connected through N-HN hydrogen bonds, leading to a two-dimensional structure. The C-S-S-C torsion angle is -83.6 (1)°. The dihedral angle between pyridine rings is 1.86 (15)°.

Related literature

For structures containing 1H-1,2,4-triazole-5-amine-3-thiolate, see: Aldoshin et al. (2003); Hao et al. (2010); Rakova et al. (2003). For related structures, see: Brito et al. (2007); Deng et al. (2005).

Experimental

Crystal data

C₁₀H₈N₂·C₄H₆N₈S₂
M_r = 386.47
Triclinic, $[P \overline 1]$
a = 9.324 (1) Å
b = 9.4540 (11) Å
c = 11.3840 (13) Å
= 109.560 (2)°
= 104.089 (1)°
= 105.627 (1)°
V = 846.86 (17) Å³
Z = 2
Mo K radiation
= 0.34 mm^-1
T = 298 K
0.35 × 0.30 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007) T_min = 0.891, T_max = 0.933
4439 measured reflections
2952 independent reflections
2121 reflections with I > 2(I)
R_int = 0.019

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.106
S = 1.04
2952 reflections
235 parameters
H-atom parameters constrained
_max = 0.26 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	2.22	2.850 (3)	131
N4-H4AN5ⁱ	0.86	2.29	3.058 (3)	149
N4-H4BN10ⁱⁱ	0.86	2.18	2.977 (3)	154
N6-H6N9ⁱⁱⁱ	0.86	2.04	2.867 (3)	162
N8-H8AN3^iv	0.86	2.33	3.137 (3)	156
N8-H8BN7^v	0.86	2.22	3.068 (3)	167
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y+2, -z+1; (iii) -x+1, -y, -z; (iv) x, y-1, z; (v) -x+2, -y+1, -z+1.

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: QM2081 ).

Acknowledgements

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

References

Aldoshin, S. M., Sanina, N. A., Rakova, O. A., Shilov, G. V., Kulikov, A. V., Shulga, Yu. M. & Ovanesyan, N. S. (2003). Russ. Chem. Bull. Int. Ed. 52, 1702-1708.
Brito, I., Cárdenas, A., Mundaca, A., Villalobos, H. & López-Rodríguez, M. (2007). Acta Cryst. E63, o2581-o2583.
Bruker (2007). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Wisconsin, USA.
Deng, Q.-J., Yao, M.-X. & Zeng, M.-H. (2005). Acta Cryst. E61, o2239-o2240.
Hao, Z. M., Guo, C. H., Wu, H. S. & Zhang, X. M. (2010). CrystEngComm, 12, 55-58.
Rakova, O. A., Sanina, N. A., Aldoshin, S. M., Goncharova, N. V., Shilov, G. V., Shulga, Y. M. & Ovanesyan, N. S. (2003). Inorg. Chem. Commun. 6, 145-148.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds