Sodium 5-amino-1,3,4-thia­diazole-2-thiol­ate dihydrate

Wu, J.; Wang, Y.; Yi, G.; Luo, S.

doi:10.1107/S1600536809051897

Volume 66
Part 1
Page m20
January 2010

Received 5 November 2009
Accepted 2 December 2009
Online 4 December 2009

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (N-C) = 0.002 Å
R = 0.026
wR = 0.059
Data-to-parameter ratio = 18.5
Details

Sodium 5-amino-1,3,4-thiadiazole-2-thiolate dihydrate

Jiayi Wu,^a Yifeng Wang,^a Guo Yi ^a and Shuping Luo ^a ^*

^aState Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou, 310014, People's Republic of China
Correspondence e-mail: jiayiwu1984@163.com

There are two 5-amino-1,3,4-thiadiazole-2(3H)-thiolate anions in the asymmetric unit of the title compound, Na⁺·C₂H₂N₃S₂^-·2H₂O, which are almost perpendicular to each other [dihedral angle = 84.64 (6)°]. The two Na⁺ cations are in distorted fourfold coordinations by O atoms of the water molecules. The crystal structure is stabilized by N-HS, O-HN and O-HS hydrogen bonds.

Related literature

For use of 5-amino-1,3,4-thiadiazole-2(3<i>H</i>)-thione derivatives as intermediates for pharmaceuticals, see: John & Gilmer (1960); John (1962); For related structures, see: Downie et al. (1971); Deng et al. (2005); Ma et al. (2007).

Experimental

Crystal data

Na⁺·C₂H₂N₃S₂^-·2H₂O
M_r = 191.21
Monoclinic, P 2₁ /c
a = 8.7810 (3) Å
b = 20.0593 (5) Å
c = 8.4351 (3) Å
= 91.026 (1)°
V = 1485.53 (8) Å³
Z = 8
Mo K radiation
= 0.72 mm^-1
T = 296 K
0.38 × 0.28 × 0.17 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) T_min = 0.758, T_max = 0.885
14264 measured reflections
3376 independent reflections
2974 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.026
wR(F²) = 0.059
S = 1.00
3376 reflections
182 parameters
H-atom parameters constrained
_max = 0.30 e Å^-3
_min = -0.32 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2A-H104N3B	0.85	1.99	2.8113 (18)	161
O1A-H102S1B	0.87	2.39	3.2563 (14)	172
O2B-H201S1Bⁱ	0.86	2.45	3.2962 (12)	169
O2B-H202N2Bⁱⁱ	0.86	1.95	2.8024 (18)	170
N1A-H1A2S1Bⁱⁱⁱ	0.86	2.57	3.4081 (16)	165
N1B-H1B2S1A^iv	0.86	2.43	3.2589 (17)	161
Symmetry codes: (i) x, y, z+1; (ii) -x+1, -y+1, -z+1; (iii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: PROCESS-AUTO (Rigaku/MSC, 2006); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2208 ).

References

Deng, Q.-J., Yao, M.-X. & Zeng, M.-H. (2005). Acta Cryst. E61, o2239-o2240.
Downie, T. C., Harrison, W., Raper, E. S. & Hepworth, M. A. (1971). Acta Cryst. B61, 1584-1590.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
John, S. (1962). US Patent 3033901.
John, S. & Gilmer, T. W. (1960). US Patent 2966495.
Ma, C., Sun, J., Zheng, R. & Wang, D. (2007). Organomet. Chem. 692, 4029-4042.
Rigaku/MSC (2006). PROCESS-AUTO. Rigaku/MSC, The Woodlands, Texas, USA.
Rigaku/MSC. (2007). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

metal-organic compounds