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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 [sigma](C-C) = 0.005 Å
R = 0.043
wR = 0.106
Data-to-parameter ratio = 12.6
Details
Open access

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

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-H...N 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[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.]); Hao et al. (2010[Hao, Z. M., Guo, C. H., Wu, H. S. & Zhang, X. M. (2010). CrystEngComm, 12, 55-58.]); Rakova et al. (2003[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.]). For related structures, see: Brito et al. (2007[Brito, I., Cárdenas, A., Mundaca, A., Villalobos, H. & López-Rodríguez, M. (2007). Acta Cryst. E63, o2581-o2583.]); Deng et al. (2005[Deng, Q.-J., Yao, M.-X. & Zeng, M.-H. (2005). Acta Cryst. E61, o2239-o2240.]).

[Scheme 1]

Experimental

Crystal data
  • C10H8N2·C4H6N8S2

  • Mr = 386.47

  • Triclinic, [P \overline 1]

  • a = 9.324 (1) Å

  • b = 9.4540 (11) Å

  • c = 11.3840 (13) Å

  • [alpha] = 109.560 (2)°

  • [beta] = 104.089 (1)°

  • [gamma] = 105.627 (1)°

  • V = 846.86 (17) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2007). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Wisconsin, USA.]) Tmin = 0.891, Tmax = 0.933

  • 4439 measured reflections

  • 2952 independent reflections

  • 2121 reflections with I > 2[sigma](I)

  • Rint = 0.019

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.106

  • S = 1.04

  • 2952 reflections

  • 235 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2...N1i 0.86 2.22 2.850 (3) 131
N4-H4A...N5i 0.86 2.29 3.058 (3) 149
N4-H4B...N10ii 0.86 2.18 2.977 (3) 154
N6-H6...N9iii 0.86 2.04 2.867 (3) 162
N8-H8A...N3iv 0.86 2.33 3.137 (3) 156
N8-H8B...N7v 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[Bruker (2007). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2007[Bruker (2007). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [CrossRef] [ChemPort]
Brito, I., Cárdenas, A., Mundaca, A., Villalobos, H. & López-Rodríguez, M. (2007). Acta Cryst. E63, o2581-o2583.  [CSD] [CrossRef] [details]
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.  [CSD] [CrossRef] [details]
Hao, Z. M., Guo, C. H., Wu, H. S. & Zhang, X. M. (2010). CrystEngComm, 12, 55-58.  [ISI] [CSD] [CrossRef] [ChemPort]
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.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3194  [ doi:10.1107/S1600536812042742 ]

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