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Volume 65 
Part 9 
Page o2138  
September 2009  

Received 21 July 2009
Accepted 31 July 2009
Online 12 August 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.029
wR = 0.078
Data-to-parameter ratio = 13.0
Details
Open access

N-(5-Methylsulfanyl-1,3,4-thiadiazol-2-yl)acetamide

aCollege of Chemistry and Life Science, Tianjin Normal University, Tianjin 300074, People's Republic of China
Correspondence e-mail: hsxyzgy@mail.tjnu.edu.cn

In the title compound, C5H7N3OS2, inversion dimers linked by pairs of N-H...N hydrogen bonds occur, forming R22(8) ring motifs. These dimers are arranged into chains via intermolecular C-H...O hydrogen bonds between the methylsulfanyl groups and the O atoms of the carbonyl groups. The acetamido-1,3,4-thiodiazole unit is essentially planar [r.m.s. deviation 0.045 (8) Å].

Related literature

For the applications of 1,3,4-thiodiazole and its derivatives in antimicrobial drugs and in the construction of metal-organic frameworks, see: Gardinier et al. (2007[Gardinier, J. R., Silva, R. M., Gwengo, C. & Lindeman, S. V. (2007). Chem. Commun. pp. 1524-1526.]); Mrozek et al. (2000[Mrozek, A., Karolak-Wojciechowska, J., Amiel, P. & Barbe, J. (2000). J. Mol. Struct. 524, 159-167.]); Xue et al. (2008[Xue, D.-X., Zhang, W.-X., Chen, X.-M. & Wang, H.-Z. (2008). Chem. Commun. pp. 1551-1553.]). For the synthesis, see: Clerici & Pocar (2001[Clerici, F. & Pocar, D. (2001). J. Med. Chem. 44, 931-936.]).

[Scheme 1]

Experimental

Crystal data
  • C5H7N3OS2

  • Mr = 189.26

  • Triclinic, [P \overline 1]

  • a = 5.0797 (10) Å

  • b = 7.9894 (16) Å

  • c = 10.081 (2) Å

  • [alpha] = 91.96 (3)°

  • [beta] = 90.94 (3)°

  • [gamma] = 105.27 (3)°

  • V = 394.32 (14) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.62 mm-1

  • T = 293 K

  • 0.30 × 0.30 × 0.10 mm

Data collection
  • Rigaku R-AXIS RAPID-S diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1998[Bruker (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.836, Tmax = 0.941

  • 3437 measured reflections

  • 1382 independent reflections

  • 1259 reflections with I > 2[sigma](I)

  • Rint = 0.016

Refinement
  • R[F2 > 2[sigma](F2)] = 0.029

  • wR(F2) = 0.078

  • S = 1.07

  • 1382 reflections

  • 106 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3...N2i 0.77 (2) 2.12 (2) 2.881 (2) 173 (2)
C1-H1B...O1ii 0.96 2.58 3.289 (3) 131 (2)
Symmetry codes: (i) -x+2, -y+2, -z+2; (ii) -x+1, -y+1, -z+1.

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: BQ2155 ).


Acknowledgements

We are grateful for financial support from the Program for Excellent Introduced Talents of Tianjin Normal University in China (No. 5RL052).

References

Bruker (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Clerici, F. & Pocar, D. (2001). J. Med. Chem. 44, 931-936.  [ISI] [CrossRef] [PubMed] [ChemPort]
Gardinier, J. R., Silva, R. M., Gwengo, C. & Lindeman, S. V. (2007). Chem. Commun. pp. 1524-1526.  [CSD] [CrossRef]
Mrozek, A., Karolak-Wojciechowska, J., Amiel, P. & Barbe, J. (2000). J. Mol. Struct. 524, 159-167.  [ISI] [CrossRef] [ChemPort]
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Xue, D.-X., Zhang, W.-X., Chen, X.-M. & Wang, H.-Z. (2008). Chem. Commun. pp. 1551-1553.  [CSD] [CrossRef]


Acta Cryst (2009). E65, o2138  [ doi:10.1107/S1600536809030554 ]

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