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

Zhang, G.-Y.

doi:10.1107/S1600536809030554

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 (C-C) = 0.003 Å
R = 0.029
wR = 0.078
Data-to-parameter ratio = 13.0
Details

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

Guo-Ying Zhang ^a ^*

^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-HN hydrogen bonds occur, forming R₂²(8) ring motifs. These dimers are arranged into chains via intermolecular C-HO 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); Mrozek et al. (2000); Xue et al. (2008). For the synthesis, see: Clerici & Pocar (2001).

Experimental

Crystal data

C₅H₇N₃OS₂
M_r = 189.26
Triclinic, $[P \overline 1]$
a = 5.0797 (10) Å
b = 7.9894 (16) Å
c = 10.081 (2) Å
= 91.96 (3)°
= 90.94 (3)°
= 105.27 (3)°
V = 394.32 (14) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.836, T_max = 0.941
3437 measured reflections
1382 independent reflections
1259 reflections with I > 2(I)
R_int = 0.016

Refinement

R[F² > 2(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
_max = 0.25 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3N2ⁱ	0.77 (2)	2.12 (2)	2.881 (2)	173 (2)
C1-H1BO1ⁱⁱ	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); cell refinement: CrystalClear; data reduction: CrystalClear; 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: 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.
Gardinier, J. R., Silva, R. M., Gwengo, C. & Lindeman, S. V. (2007). Chem. Commun. pp. 1524-1526.
Mrozek, A., Karolak-Wojciechowska, J., Amiel, P. & Barbe, J. (2000). J. Mol. Struct. 524, 159-167.
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Xue, D.-X., Zhang, W.-X., Chen, X.-M. & Wang, H.-Z. (2008). Chem. Commun. pp. 1551-1553.

organic compounds