[Journal logo]

Volume 69 
Part 5 
Page o712  
May 2013  

Received 3 March 2013
Accepted 7 April 2013
Online 13 April 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.044
wR = 0.124
Data-to-parameter ratio = 15.0
Details
Open access

Methyl 3-(pyridin-4-ylmethylidene)dithiocarbazate

aDeparment of Chemistry, Anhui University, Hefei 230039, People's Republic of China, and bKey Laboratory of Functional Inorganic Materials, Chemistry, Hefei 230039, People's Republic of China
Correspondence e-mail: yptian@ahu.edu.cn

There are two independent molecules in the asymmetric unit of the title molecule, C8H9N3S2, both of which exhibit an E conformation with the pyridine ring and dithiocarbazate fragment located on opposite sides of the C=N bond. The pyridine ring and dithiocarbazate group are approximately coplanar, with dihedral angles of 4.74 (1) and 8.77 (1)° between their planes in the two molecules. In the crystal, molecules are linked to each other via N-H...N hydrogen bonds, forming zigzag chains parallel to [10-1].

Related literature

For related structures, see: Shan et al. (2006[Shan, S., Zhang, Y.-L. & Xu, D.-J. (2006). Acta Cryst. E62, o1567-o1569.]); Chen et al. (2007[Chen, Z.-Y., Wu, G.-Q., Jiang, F.-X., Tian, Y.-L. & Shan, S. (2007). Acta Cryst. E63, o1919-o1920.]). Derivatives of the title compound are often used as coordinating ligands in the metal complexes, see for example: Wu et al. (2001[Wu, J.-Y., Chantrapromma, S., Chen, D.-W., Tian, Y.-P., Yang, P. & Fun, H.-K. (2001). Acta Cryst. C57, 523-525.]); Fun et al. (2001[Fun, H.-K., Chantrapromma, S., Razak, I. A., Usman, A., Tang, Y. W., Ma, W., Wu, J. Y. & Tian, Y. P. (2001). Acta Cryst. E57, m519-m521.]).

[Scheme 1]

Experimental

Crystal data
  • C8H9N3S2

  • Mr = 211.30

  • Monoclinic, P 21 /c

  • a = 7.547 (5) Å

  • b = 20.216 (5) Å

  • c = 13.415 (5) Å

  • [beta] = 96.070 (5)°

  • V = 2035.3 (16) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.48 mm-1

  • T = 296 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.870, Tmax = 0.910

  • 14118 measured reflections

  • 3565 independent reflections

  • 2379 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.124

  • S = 1.02

  • 3565 reflections

  • 237 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.40 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3B-H3B...N1Ai 0.86 2.04 2.904 (3) 179
N3A-H3A...N1Bii 0.86 2.07 2.909 (3) 166
Symmetry codes: (i) [x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (ii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: GG2112 ).


Acknowledgements

This work was supported by the National Natural Science Foundation of China (21071001, 21271004) and grants from the Postdoctoral Foundation of Anhui Province.

References

Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, Z.-Y., Wu, G.-Q., Jiang, F.-X., Tian, Y.-L. & Shan, S. (2007). Acta Cryst. E63, o1919-o1920.  [CSD] [CrossRef] [ChemPort] [details]
Fun, H.-K., Chantrapromma, S., Razak, I. A., Usman, A., Tang, Y. W., Ma, W., Wu, J. Y. & Tian, Y. P. (2001). Acta Cryst. E57, m519-m521.  [CSD] [CrossRef] [ChemPort] [details]
Shan, S., Zhang, Y.-L. & Xu, D.-J. (2006). Acta Cryst. E62, o1567-o1569.  [CSD] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Wu, J.-Y., Chantrapromma, S., Chen, D.-W., Tian, Y.-P., Yang, P. & Fun, H.-K. (2001). Acta Cryst. C57, 523-525.  [CSD] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o712  [ doi:10.1107/S1600536813009409 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.