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Volume 69 
Part 2 
Page o171  
February 2013  

Received 20 November 2012
Accepted 4 December 2012
Online 4 January 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.006 Å
R = 0.063
wR = 0.165
Data-to-parameter ratio = 12.1
Details
Open access

6-Nitro-1,3-benzothiazole-2(3H)-thione

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 molecule, C7H4N2O2S2, the nitro group is twisted by 5.5 (1)° from the plane of the attached benzene ring. In the crystal, N-H...S hydrogen bonds link pairs of molecules into inversion dimers, which are linked by weak C-H...O interactions into sheets parallel to (101). The crystal packing exhibits short intermolecular S...O contacts of 3.054 (4) Å and [pi]-[pi] interactions of 3.588 (5) Å between the centroids of the five- and six-membered rings of neighbouring molecules.

Related literature

For coordination compounds based on 2-mercapto-6-nitrobenzothiazole ligands, see: Ma et al. (2003a[Ma, C. L., Jiang, Q. & Zhang, R. F. (2003a). Can. J. Chem. 81, 825-831.],b[Ma, C. L., Jiang, Q. & Zhang, R. F. (2003b). Appl. Organomet. Chem. 17, 623-630.], 2004[Ma, C. L., Jiang, Q. & Zhang, R. F. (2004). Polyhedron, 23, 779-786.]). For the structure of the related compound 2-mercapto-benzothiazole, see: Chesick & Donohue (1971[Chesick, J. P. & Donohue, J. (1971). Acta Cryst. B27, 1441-1444.]).

[Scheme 1]

Experimental

Crystal data
  • C7H4N2O2S2

  • Mr = 212.24

  • Monoclinic, P 21 /n

  • a = 3.8645 (2) Å

  • b = 26.345 (2) Å

  • c = 7.8961 (4) Å

  • [beta] = 92.509 (1)°

  • V = 803.14 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.62 mm-1

  • T = 298 K

  • 0.40 × 0.35 × 0.27 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 = 0.789, Tmax = 0.850

  • 4092 measured reflections

  • 1425 independent reflections

  • 1104 reflections with I > 2[sigma](I)

  • Rint = 0.109

Refinement
  • R[F2 > 2[sigma](F2)] = 0.063

  • wR(F2) = 0.165

  • S = 1.04

  • 1425 reflections

  • 118 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.45 e Å-3

  • [Delta][rho]min = -0.42 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...S2i 0.86 2.45 3.271 (3) 160
C4-H4...O1ii 0.93 2.60 3.285 (6) 131
Symmetry codes: (i) -x, -y, -z+1; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

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: CV5367 ).


Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant No. 21171119), the National High Technology Research and Development Program 863 of China (grant 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

Bruker (2007). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Wisconsin, USA.
Chesick, J. P. & Donohue, J. (1971). Acta Cryst. B27, 1441-1444.  [CrossRef] [ChemPort] [details] [ISI]
Ma, C. L., Jiang, Q. & Zhang, R. F. (2003a). Can. J. Chem. 81, 825-831.  [ISI] [CSD] [CrossRef] [ChemPort]
Ma, C. L., Jiang, Q. & Zhang, R. F. (2003b). Appl. Organomet. Chem. 17, 623-630.  [ISI] [CSD] [CrossRef] [ChemPort]
Ma, C. L., Jiang, Q. & Zhang, R. F. (2004). Polyhedron, 23, 779-786.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o171  [ doi:10.1107/S1600536812049719 ]

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