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ISSN: 2056-9890

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

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

(Received 5 November 2009; accepted 2 December 2009; online 4 December 2009)

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—H⋯S, O—H⋯N and O—H⋯S 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, S. & Gilmer, T. W. (1960). US Patent 2966495.]); John (1962[John, S. (1962). US Patent 3033901.]); For related structures, see: Downie et al. (1971[Downie, T. C., Harrison, W., Raper, E. S. & Hepworth, M. A. (1971). Acta Cryst. B61, 1584-1590.]); Deng et al. (2005[Deng, Q.-J., Yao, M.-X. & Zeng, M.-H. (2005). Acta Cryst. E61, o2239-o2240.]); Ma et al. (2007[Ma, C., Sun, J., Zheng, R. & Wang, D. (2007). Organomet. Chem. 692, 4029-4042.]).

[Scheme 1]

Experimental

Crystal data
  • Na+·C2H2N3S2·2H2O

  • Mr = 191.21

  • Monoclinic, P 21 /c

  • a = 8.7810 (3) Å

  • b = 20.0593 (5) Å

  • c = 8.4351 (3) Å

  • β = 91.026 (1)°

  • V = 1485.53 (8) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 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[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.758, Tmax = 0.885

  • 14264 measured reflections

  • 3376 independent reflections

  • 2974 reflections with I > 2σ(I)

  • Rint = 0.026

Refinement
  • R[F2 > 2σ(F2)] = 0.026

  • wR(F2) = 0.059

  • S = 1.00

  • 3376 reflections

  • 182 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.32 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2A—H104⋯N3B 0.85 1.99 2.8113 (18) 161
O1A—H102⋯S1B 0.87 2.39 3.2563 (14) 172
O2B—H201⋯S1Bi 0.86 2.45 3.2962 (12) 169
O2B—H202⋯N2Bii 0.86 1.95 2.8024 (18) 170
N1A—H1A2⋯S1Biii 0.86 2.57 3.4081 (16) 165
N1B—H1B2⋯S1Aiv 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[Rigaku/MSC (2006). PROCESS-AUTO. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2007[Rigaku/MSC. (2007). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

Interest in the study of 5-amino-1,3,4-thiadiazole-2(3H)-thione derivatives stems from their use as intermediates of pharmaceuticals (John et al., 1960; John, 1962). Nonetheless, there are few articles that describe this kind of crystal structure (Downie et al., 1972; Deng et al., 2005; Ma et al., 2007). As part of our studies of agrochemicals, the title compound 5-amino-2-thione-1,3,4-thiadiazole sodium dihydrate has been synthesized, and its crystal structure is reported in this article. The complex is located across an inversion centre, and is bridged by two symmetry equivalent water molecules Na—O (bridge) distances of 2.3776 (14) Å and 2.5141 (15) Å and an Na—O—Na bond angle of 98.99 (3)°. It has two 5-amino-1,3,4-thiadiazole-2(3H)-thione molecules in the asymmetric unit that are almost perpendicular to each other [dihedral angle = 84.64 (6)°]. The structure is stabilized by N—H···S, O—H···N and O—H···S hydrogen bonds.

Related literature top

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

Experimental top

5-amino-1,3,4-thiadiazole-2(3H)-thione(0.1 mmol) and sodium hydroxide (0.1 mmol) were dissolved in water (10 ml) and stirred for 3 h. The water was then removed under reduced pressure. Single crystals were obtained by slow evaporation of a methanol solution at room temperature.

Refinement top

All H atoms were initially located in a difference Fourier map. N-bound H atoms were located in a difference map and refined with an N—H distance restraint of 0.86 (1) Å. The water H atoms were refined using a riding model, with Uiso(H)=1.5eq(O).

Computing details top

Data collection: PROCESS-AUTO (Rigaku/MSC, 2006); cell refinement: PROCESS-AUTO (Rigaku/MSC, 2006); 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).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound with the atomic labeling scheme. Displacement ellipsoids are drawn at the 40% probability level.
[Figure 2] Fig. 2. A partial packing diagram of title compound.
Sodium 5-amino-1,3,4-thiadiazole-2-thiolate dihydrate top
Crystal data top
Na+·C2H2N3S2·2H2OF(000) = 784
Mr = 191.21Dx = 1.710 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 11555 reflections
a = 8.7810 (3) Åθ = 3.0–27.4°
b = 20.0593 (5) ŵ = 0.72 mm1
c = 8.4351 (3) ÅT = 296 K
β = 91.026 (1)°Block, colorless
V = 1485.53 (8) Å30.38 × 0.28 × 0.17 mm
Z = 8
Data collection top
Rigaku R-AXIS RAPID
diffractometer
3376 independent reflections
Radiation source: rolling anode2974 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
Detector resolution: 10.00 pixels mm-1θmax = 27.4°, θmin = 3.1°
ω scansh = 1111
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 2525
Tmin = 0.758, Tmax = 0.885l = 1010
14264 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.026H-atom parameters constrained
wR(F2) = 0.059 w = 1/[σ2(Fo2) + (0.014P)2 + 1.P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
3376 reflectionsΔρmax = 0.30 e Å3
182 parametersΔρmin = 0.32 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0516 (12)
Crystal data top
Na+·C2H2N3S2·2H2OV = 1485.53 (8) Å3
Mr = 191.21Z = 8
Monoclinic, P21/cMo Kα radiation
a = 8.7810 (3) ŵ = 0.72 mm1
b = 20.0593 (5) ÅT = 296 K
c = 8.4351 (3) Å0.38 × 0.28 × 0.17 mm
β = 91.026 (1)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
3376 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
2974 reflections with I > 2σ(I)
Tmin = 0.758, Tmax = 0.885Rint = 0.026
14264 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0260 restraints
wR(F2) = 0.059H-atom parameters constrained
S = 1.00Δρmax = 0.30 e Å3
3376 reflectionsΔρmin = 0.32 e Å3
182 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S2B0.46866 (5)0.720405 (18)0.04494 (5)0.03114 (11)
S2A0.97675 (5)0.708164 (18)0.53837 (5)0.03013 (10)
S1B0.71560 (5)0.66512 (2)0.16488 (6)0.03952 (12)
S1A1.23359 (5)0.65778 (2)0.75020 (5)0.03794 (12)
Na1B0.71086 (8)0.49937 (4)0.47238 (8)0.04359 (19)
Na1A0.98033 (7)0.50450 (3)0.20940 (8)0.03560 (16)
O2A0.70915 (13)0.49947 (6)0.18979 (14)0.0359 (3)
H1040.65540.52210.12370.054*
H1030.68970.45850.16990.054*
O1A0.99706 (15)0.58368 (6)0.00068 (15)0.0446 (3)
H1011.07200.60800.02670.067*
H1020.92270.60810.03580.067*
O2B0.75550 (13)0.50610 (6)0.74664 (14)0.0347 (3)
H2040.51820.60620.42940.052*
H2030.51560.60660.58120.052*
N2B0.41175 (17)0.60144 (7)0.13535 (18)0.0379 (3)
N2A0.93910 (16)0.58939 (6)0.43221 (16)0.0320 (3)
N3B0.53241 (16)0.59605 (7)0.03004 (17)0.0356 (3)
O1B0.50110 (17)0.57964 (7)0.50136 (16)0.0540 (4)
H2010.73280.54600.77540.081*
H2020.69640.47670.78800.081*
N3A1.05908 (15)0.58553 (6)0.54520 (15)0.0307 (3)
C2A0.88628 (18)0.65001 (7)0.41696 (18)0.0278 (3)
N1A0.76956 (18)0.66682 (7)0.31696 (18)0.0426 (4)
H1A10.72610.63680.25920.051*
H1A20.73910.70750.31140.051*
C1B0.57417 (17)0.65311 (7)0.02914 (18)0.0277 (3)
C2B0.36620 (18)0.66293 (8)0.15350 (18)0.0304 (3)
N1B0.24845 (18)0.67989 (8)0.2467 (2)0.0479 (4)
H1B10.20000.64960.29720.057*
H1B20.22210.72100.25540.057*
C1A1.09218 (17)0.64295 (7)0.61080 (17)0.0262 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S2B0.0345 (2)0.02059 (18)0.0384 (2)0.00051 (15)0.00191 (16)0.00096 (15)
S2A0.0354 (2)0.02064 (18)0.0342 (2)0.00192 (15)0.00284 (16)0.00291 (15)
S1B0.0396 (2)0.0309 (2)0.0485 (3)0.00355 (17)0.01226 (19)0.00579 (18)
S1A0.0416 (2)0.0306 (2)0.0411 (2)0.00624 (17)0.01399 (18)0.00242 (17)
Na1B0.0385 (4)0.0584 (5)0.0339 (4)0.0037 (3)0.0013 (3)0.0044 (3)
Na1A0.0322 (3)0.0395 (4)0.0351 (3)0.0030 (3)0.0002 (3)0.0019 (3)
O2A0.0390 (6)0.0304 (6)0.0380 (6)0.0020 (5)0.0086 (5)0.0004 (5)
O1A0.0437 (7)0.0404 (7)0.0497 (7)0.0024 (6)0.0003 (6)0.0079 (6)
O2B0.0352 (6)0.0321 (6)0.0370 (6)0.0011 (5)0.0036 (5)0.0002 (5)
N2B0.0408 (8)0.0264 (7)0.0467 (8)0.0025 (6)0.0098 (6)0.0080 (6)
N2A0.0395 (7)0.0238 (6)0.0323 (7)0.0009 (6)0.0083 (6)0.0022 (5)
N3B0.0383 (8)0.0251 (7)0.0437 (8)0.0045 (6)0.0069 (6)0.0060 (6)
O1B0.0642 (9)0.0502 (8)0.0478 (8)0.0032 (7)0.0073 (7)0.0103 (6)
N3A0.0358 (7)0.0230 (6)0.0330 (7)0.0014 (5)0.0071 (6)0.0008 (5)
C2A0.0318 (8)0.0251 (7)0.0266 (7)0.0002 (6)0.0001 (6)0.0010 (6)
N1A0.0486 (9)0.0313 (7)0.0473 (9)0.0050 (6)0.0182 (7)0.0007 (6)
C1B0.0284 (7)0.0240 (7)0.0304 (7)0.0020 (6)0.0050 (6)0.0014 (6)
C2B0.0325 (8)0.0278 (8)0.0308 (8)0.0020 (6)0.0017 (6)0.0029 (6)
N1B0.0521 (10)0.0336 (8)0.0588 (10)0.0017 (7)0.0236 (8)0.0014 (7)
C1A0.0296 (7)0.0233 (7)0.0257 (7)0.0010 (6)0.0020 (6)0.0029 (6)
Geometric parameters (Å, º) top
S2B—C2B1.7340 (16)O2B—Na1Aii2.3521 (13)
S2B—C1B1.7583 (15)O2B—H2010.8609
S2A—C2A1.7354 (15)O2B—H2020.8632
S2A—C1A1.7578 (15)N2B—C2B1.306 (2)
S1B—C1B1.7211 (16)N2B—N3B1.3989 (19)
S1A—C1A1.7207 (16)N2A—C2A1.3071 (19)
Na1B—O2B2.3433 (13)N2A—N3A1.4100 (18)
Na1B—O2A2.3835 (13)N3B—C1B1.304 (2)
Na1B—O1Bi2.4576 (17)O1B—Na1Bi2.4576 (17)
Na1B—O1B2.4619 (16)O1B—H2040.8227
Na1B—Na1A3.2739 (10)O1B—H2030.8710
Na1A—O2Bii2.3521 (13)N3A—C1A1.3082 (19)
Na1A—O1A2.3776 (14)N3A—Na1Bii2.6485 (15)
Na1A—O2A2.3862 (14)N3A—Na1Aii2.7735 (15)
Na1A—O1Aiii2.5141 (15)C2A—N1A1.358 (2)
O2A—H1040.8538N1A—H1A10.8600
O2A—H1030.8559N1A—H1A20.8600
O1A—Na1Aiii2.5141 (15)C2B—N1B1.354 (2)
O1A—H1010.8545N1B—H1B10.8600
O1A—H1020.8684N1B—H1B20.8600
C2B—S2B—C1B87.65 (8)Na1B—Na1A—Na1Aiii139.01 (3)
C2A—S2A—C1A87.70 (7)O2Bii—Na1A—Na1Bii36.27 (3)
O2B—Na1B—O2A170.14 (5)O1A—Na1A—Na1Bii119.10 (4)
O2B—Na1B—O1Bi93.54 (5)O2A—Na1A—Na1Bii138.61 (4)
O2A—Na1B—O1Bi95.71 (5)O1Aiii—Na1A—Na1Bii114.91 (4)
O2B—Na1B—O1B88.66 (5)N2A—Na1A—Na1Bii66.59 (3)
O2A—Na1B—O1B96.17 (5)N3Aii—Na1A—Na1Bii63.54 (3)
O1Bi—Na1B—O1B81.01 (6)Na1B—Na1A—Na1Bii92.07 (2)
O2B—Na1B—N3Aii88.74 (5)Na1Aiii—Na1A—Na1Bii128.47 (3)
O2A—Na1B—N3Aii86.31 (5)Na1B—O2A—Na1A86.69 (4)
O1Bi—Na1B—N3Aii99.79 (5)Na1B—O2A—H104130.3
O1B—Na1B—N3Aii177.32 (5)Na1A—O2A—H104124.2
O2B—Na1B—N2A88.52 (5)Na1B—O2A—H103101.1
O2A—Na1B—N2A82.33 (4)Na1A—O2A—H103104.4
O1Bi—Na1B—N2A177.48 (5)H104—O2A—H103106.1
O1B—Na1B—N2A97.60 (5)Na1A—O1A—Na1Aiii93.36 (5)
N3Aii—Na1B—N2A81.70 (5)Na1A—O1A—H101129.8
O2B—Na1B—Na1A123.85 (4)Na1Aiii—O1A—H10198.1
O2A—Na1B—Na1A46.69 (3)Na1A—O1A—H102125.7
O1Bi—Na1B—Na1A129.72 (5)Na1Aiii—O1A—H102102.5
O1B—Na1B—Na1A126.71 (4)H101—O1A—H10299.2
N3Aii—Na1B—Na1A54.62 (3)Na1B—O2B—Na1Aii107.31 (5)
N2A—Na1B—Na1A49.64 (3)Na1B—O2B—H201107.3
O2B—Na1B—Na1Bi91.44 (4)Na1Aii—O2B—H201105.8
O2A—Na1B—Na1Bi97.82 (4)Na1B—O2B—H202105.6
O1Bi—Na1B—Na1Bi40.55 (4)Na1Aii—O2B—H202118.2
O1B—Na1B—Na1Bi40.46 (4)H201—O2B—H202112.2
N3Aii—Na1B—Na1Bi140.27 (5)C2B—N2B—N3B112.60 (13)
N2A—Na1B—Na1Bi138.02 (5)C2A—N2A—N3A112.15 (12)
Na1A—Na1B—Na1Bi144.42 (3)C2A—N2A—Na1A126.84 (10)
O2B—Na1B—Na1Aii36.43 (3)N3A—N2A—Na1A110.19 (9)
O2A—Na1B—Na1Aii134.54 (4)C2A—N2A—Na1B111.62 (10)
O1Bi—Na1B—Na1Aii117.21 (4)N3A—N2A—Na1B114.97 (9)
O1B—Na1B—Na1Aii118.11 (4)Na1A—N2A—Na1B76.41 (4)
N3Aii—Na1B—Na1Aii59.24 (3)C1B—N3B—N2B113.37 (13)
N2A—Na1B—Na1Aii65.29 (3)Na1Bi—O1B—Na1B98.99 (6)
Na1A—Na1B—Na1Aii87.93 (2)Na1Bi—O1B—H204129.2
Na1Bi—Na1B—Na1Aii127.63 (3)Na1B—O1B—H204101.7
O2Bii—Na1A—O1A95.93 (5)Na1Bi—O1B—H203115.5
O2Bii—Na1A—O2A170.82 (5)Na1B—O1B—H203112.5
O1A—Na1A—O2A92.97 (5)H204—O1B—H20398.3
O2Bii—Na1A—O1Aiii87.56 (5)C1A—N3A—N2A113.29 (12)
O1A—Na1A—O1Aiii86.64 (5)C1A—N3A—Na1Bii115.21 (10)
O2A—Na1A—O1Aiii90.73 (5)N2A—N3A—Na1Bii123.97 (9)
O2Bii—Na1A—N2A95.52 (5)C1A—N3A—Na1Aii106.70 (10)
O1A—Na1A—N2A96.34 (5)N2A—N3A—Na1Aii116.01 (9)
O2A—Na1A—N2A85.71 (5)Na1Bii—N3A—Na1Aii74.25 (4)
O1Aiii—Na1A—N2A175.46 (5)N2A—C2A—N1A123.68 (14)
O2Bii—Na1A—N3Aii87.67 (4)N2A—C2A—S2A114.17 (11)
O1A—Na1A—N3Aii176.24 (5)N1A—C2A—S2A122.15 (12)
O2A—Na1A—N3Aii83.48 (4)C2A—N1A—H1A1120.0
O1Aiii—Na1A—N3Aii94.61 (4)C2A—N1A—H1A2120.0
N2A—Na1A—N3Aii82.20 (4)H1A1—N1A—H1A2120.0
O2Bii—Na1A—Na1B127.81 (4)N3B—C1B—S1B126.07 (12)
O1A—Na1A—Na1B125.29 (4)N3B—C1B—S2B112.60 (12)
O2A—Na1A—Na1B46.62 (3)S1B—C1B—S2B121.34 (9)
O1Aiii—Na1A—Na1B121.51 (4)N2B—C2B—N1B122.96 (15)
N2A—Na1A—Na1B53.95 (4)N2B—C2B—S2B113.76 (12)
N3Aii—Na1A—Na1B51.13 (3)N1B—C2B—S2B123.27 (13)
O2Bii—Na1A—Na1Aiii92.23 (4)C2B—N1B—H1B1120.0
O1A—Na1A—Na1Aiii44.83 (4)C2B—N1B—H1B2120.0
O2A—Na1A—Na1Aiii92.49 (4)H1B1—N1B—H1B2120.0
O1Aiii—Na1A—Na1Aiii41.81 (3)N3A—C1A—S1A126.40 (12)
N2A—Na1A—Na1Aiii141.05 (5)N3A—C1A—S2A112.69 (11)
N3Aii—Na1A—Na1Aiii136.32 (4)S1A—C1A—S2A120.89 (9)
O2B—Na1B—Na1A—O2Bii13.17 (9)Na1A—Na1B—O2B—Na1Aii10.87 (7)
O2A—Na1B—Na1A—O2Bii170.38 (7)Na1Bi—Na1B—O2B—Na1Aii173.99 (4)
O1Bi—Na1B—Na1A—O2Bii117.66 (7)O2Bii—Na1A—N2A—C2A119.25 (13)
O1B—Na1B—Na1A—O2Bii130.87 (7)O1A—Na1A—N2A—C2A22.63 (14)
N3Aii—Na1B—Na1A—O2Bii46.25 (6)O2A—Na1A—N2A—C2A69.88 (14)
N2A—Na1B—Na1A—O2Bii65.53 (6)N3Aii—Na1A—N2A—C2A153.88 (14)
Na1Bi—Na1B—Na1A—O2Bii175.20 (6)Na1B—Na1A—N2A—C2A107.01 (14)
Na1Aii—Na1B—Na1A—O2Bii6.74 (5)Na1Aiii—Na1A—N2A—C2A18.77 (17)
O2B—Na1B—Na1A—O1A122.01 (6)Na1Bii—Na1A—N2A—C2A141.65 (14)
O2A—Na1B—Na1A—O1A54.43 (6)O2Bii—Na1A—N2A—N3A21.79 (10)
O1Bi—Na1B—Na1A—O1A107.16 (7)O1A—Na1A—N2A—N3A118.40 (10)
O1B—Na1B—Na1A—O1A4.31 (8)O2A—Na1A—N2A—N3A149.09 (10)
N3Aii—Na1B—Na1A—O1A178.56 (6)N3Aii—Na1A—N2A—N3A65.09 (10)
N2A—Na1B—Na1A—O1A69.65 (6)Na1B—Na1A—N2A—N3A111.96 (10)
Na1Bi—Na1B—Na1A—O1A49.61 (9)Na1Aiii—Na1A—N2A—N3A122.26 (9)
Na1Aii—Na1B—Na1A—O1A128.44 (5)Na1Bii—Na1A—N2A—N3A0.61 (8)
O2B—Na1B—Na1A—O2A176.45 (7)O2Bii—Na1A—N2A—Na1B133.74 (4)
O1Bi—Na1B—Na1A—O2A52.73 (7)O1A—Na1A—N2A—Na1B129.64 (4)
O1B—Na1B—Na1A—O2A58.74 (7)O2A—Na1A—N2A—Na1B37.13 (4)
N3Aii—Na1B—Na1A—O2A124.13 (6)N3Aii—Na1A—N2A—Na1B46.86 (4)
N2A—Na1B—Na1A—O2A124.09 (6)Na1Aiii—Na1A—N2A—Na1B125.78 (6)
Na1Bi—Na1B—Na1A—O2A4.82 (7)Na1Bii—Na1A—N2A—Na1B111.34 (3)
Na1Aii—Na1B—Na1A—O2A177.12 (5)O2B—Na1B—N2A—C2A96.54 (11)
O2B—Na1B—Na1A—O1Aiii127.53 (6)O2A—Na1B—N2A—C2A87.15 (11)
O2A—Na1B—Na1A—O1Aiii56.03 (6)O1B—Na1B—N2A—C2A8.10 (11)
O1Bi—Na1B—Na1A—O1Aiii3.30 (8)N3Aii—Na1B—N2A—C2A174.51 (11)
O1B—Na1B—Na1A—O1Aiii114.77 (7)Na1A—Na1B—N2A—C2A124.59 (11)
N3Aii—Na1B—Na1A—O1Aiii68.10 (6)Na1Bi—Na1B—N2A—C2A6.04 (14)
N2A—Na1B—Na1A—O1Aiii179.89 (6)Na1Aii—Na1B—N2A—C2A125.60 (11)
Na1Bi—Na1B—Na1A—O1Aiii60.85 (8)O2B—Na1B—N2A—N3A32.66 (10)
Na1Aii—Na1B—Na1A—O1Aiii121.10 (5)O2A—Na1B—N2A—N3A143.65 (10)
O2B—Na1B—Na1A—N2A52.36 (6)O1B—Na1B—N2A—N3A121.10 (10)
O2A—Na1B—Na1A—N2A124.09 (6)N3Aii—Na1B—N2A—N3A56.29 (11)
O1Bi—Na1B—Na1A—N2A176.81 (7)Na1A—Na1B—N2A—N3A106.21 (10)
O1B—Na1B—Na1A—N2A65.34 (7)Na1Bi—Na1B—N2A—N3A123.16 (10)
N3Aii—Na1B—Na1A—N2A111.79 (5)Na1Aii—Na1B—N2A—N3A3.60 (9)
Na1Bi—Na1B—Na1A—N2A119.27 (8)O2B—Na1B—N2A—Na1A138.86 (4)
Na1Aii—Na1B—Na1A—N2A58.79 (4)O2A—Na1B—N2A—Na1A37.45 (4)
O2B—Na1B—Na1A—N3Aii59.43 (6)O1B—Na1B—N2A—Na1A132.69 (5)
O2A—Na1B—Na1A—N3Aii124.13 (6)N3Aii—Na1B—N2A—Na1A49.92 (4)
O1Bi—Na1B—Na1A—N3Aii71.40 (6)Na1Bi—Na1B—N2A—Na1A130.63 (6)
O1B—Na1B—Na1A—N3Aii177.13 (7)Na1Aii—Na1B—N2A—Na1A109.80 (3)
N2A—Na1B—Na1A—N3Aii111.79 (5)C2B—N2B—N3B—C1B0.4 (2)
Na1Bi—Na1B—Na1A—N3Aii128.95 (8)O2B—Na1B—O1B—Na1Bi93.80 (5)
Na1Aii—Na1B—Na1A—N3Aii52.99 (4)O2A—Na1B—O1B—Na1Bi94.83 (5)
O2B—Na1B—Na1A—Na1Aiii178.67 (5)O1Bi—Na1B—O1B—Na1Bi0.0
O2A—Na1B—Na1A—Na1Aiii4.89 (6)N2A—Na1B—O1B—Na1Bi177.88 (5)
O1Bi—Na1B—Na1A—Na1Aiii47.84 (8)Na1A—Na1B—O1B—Na1Bi133.56 (5)
O1B—Na1B—Na1A—Na1Aiii63.63 (8)Na1Aii—Na1B—O1B—Na1Bi116.13 (5)
N3Aii—Na1B—Na1A—Na1Aiii119.24 (6)C2A—N2A—N3A—C1A0.06 (19)
N2A—Na1B—Na1A—Na1Aiii128.97 (7)Na1A—N2A—N3A—C1A147.14 (11)
Na1Bi—Na1B—Na1A—Na1Aiii9.71 (10)Na1B—N2A—N3A—C1A128.88 (11)
Na1Aii—Na1B—Na1A—Na1Aiii172.24 (6)C2A—N2A—N3A—Na1Bii148.06 (11)
O2B—Na1B—Na1A—Na1Bii6.43 (4)Na1A—N2A—N3A—Na1Bii0.97 (13)
O2A—Na1B—Na1A—Na1Bii177.12 (5)Na1B—N2A—N3A—Na1Bii83.01 (11)
O1Bi—Na1B—Na1A—Na1Bii124.39 (6)C2A—N2A—N3A—Na1Aii123.98 (12)
O1B—Na1B—Na1A—Na1Bii124.14 (6)Na1A—N2A—N3A—Na1Aii88.94 (9)
N3Aii—Na1B—Na1A—Na1Bii52.99 (4)Na1B—N2A—N3A—Na1Aii4.96 (12)
N2A—Na1B—Na1A—Na1Bii58.79 (4)N3A—N2A—C2A—N1A179.29 (15)
Na1Bi—Na1B—Na1A—Na1Bii178.06 (7)Na1A—N2A—C2A—N1A40.3 (2)
Na1Aii—Na1B—Na1A—Na1Bii0.0Na1B—N2A—C2A—N1A48.62 (19)
O1Bi—Na1B—O2A—Na1A142.04 (5)N3A—N2A—C2A—S2A0.11 (17)
O1B—Na1B—O2A—Na1A136.43 (5)Na1A—N2A—C2A—S2A140.52 (9)
N3Aii—Na1B—O2A—Na1A42.56 (4)Na1B—N2A—C2A—S2A130.56 (8)
N2A—Na1B—O2A—Na1A39.55 (4)C1A—S2A—C2A—N2A0.09 (13)
Na1Bi—Na1B—O2A—Na1A177.17 (4)C1A—S2A—C2A—N1A179.29 (15)
Na1Aii—Na1B—O2A—Na1A4.04 (7)N2B—N3B—C1B—S1B178.64 (12)
O1A—Na1A—O2A—Na1B138.33 (5)N2B—N3B—C1B—S2B1.37 (18)
O1Aiii—Na1A—O2A—Na1B135.00 (4)C2B—S2B—C1B—N3B1.48 (13)
N2A—Na1A—O2A—Na1B42.18 (4)C2B—S2B—C1B—S1B178.53 (10)
N3Aii—Na1A—O2A—Na1B40.44 (4)N3B—N2B—C2B—N1B178.31 (16)
Na1Aiii—Na1A—O2A—Na1B176.79 (4)N3B—N2B—C2B—S2B0.78 (19)
Na1Bii—Na1A—O2A—Na1B4.35 (7)C1B—S2B—C2B—N2B1.26 (13)
O2Bii—Na1A—O1A—Na1Aiii87.19 (5)C1B—S2B—C2B—N1B177.82 (16)
O2A—Na1A—O1A—Na1Aiii90.55 (5)N2A—N3A—C1A—S1A178.68 (11)
O1Aiii—Na1A—O1A—Na1Aiii0.0Na1Bii—N3A—C1A—S1A27.64 (17)
N2A—Na1A—O1A—Na1Aiii176.56 (5)Na1Aii—N3A—C1A—S1A52.46 (15)
Na1B—Na1A—O1A—Na1Aiii126.85 (5)N2A—N3A—C1A—S2A0.01 (17)
Na1Bii—Na1A—O1A—Na1Aiii116.75 (4)Na1Bii—N3A—C1A—S2A151.06 (7)
O1Bi—Na1B—O2B—Na1Aii133.46 (6)Na1Aii—N3A—C1A—S2A128.85 (8)
O1B—Na1B—O2B—Na1Aii145.64 (5)C2A—S2A—C1A—N3A0.06 (12)
N3Aii—Na1B—O2B—Na1Aii33.73 (5)C2A—S2A—C1A—S1A178.72 (10)
N2A—Na1B—O2B—Na1Aii48.00 (5)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+2, y+1, z+1; (iii) x+2, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2A—H104···N3B0.851.992.8113 (18)161
O1A—H102···S1B0.872.393.2563 (14)172
O2B—H201···S1Biv0.862.453.2962 (12)169
O2B—H202···N2Bi0.861.952.8024 (18)170
N1A—H1A2···S1Bv0.862.573.4081 (16)165
N1B—H1B2···S1Avi0.862.433.2589 (17)161
Symmetry codes: (i) x+1, y+1, z+1; (iv) x, y, z+1; (v) x, y+3/2, z+1/2; (vi) x1, y+3/2, z1/2.

Experimental details

Crystal data
Chemical formulaNa+·C2H2N3S2·2H2O
Mr191.21
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)8.7810 (3), 20.0593 (5), 8.4351 (3)
β (°) 91.026 (1)
V3)1485.53 (8)
Z8
Radiation typeMo Kα
µ (mm1)0.72
Crystal size (mm)0.38 × 0.28 × 0.17
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.758, 0.885
No. of measured, independent and
observed [I > 2σ(I)] reflections
14264, 3376, 2974
Rint0.026
(sin θ/λ)max1)0.648
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.026, 0.059, 1.00
No. of reflections3376
No. of parameters182
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.32

Computer programs: PROCESS-AUTO (Rigaku/MSC, 2006), CrystalStructure (Rigaku/MSC, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2A—H104···N3B0.851.992.8113 (18)160.8
O1A—H102···S1B0.872.393.2563 (14)172.4
O2B—H201···S1Bi0.862.453.2962 (12)168.9
O2B—H202···N2Bii0.861.952.8024 (18)169.5
N1A—H1A2···S1Biii0.862.573.4081 (16)164.6
N1B—H1B2···S1Aiv0.862.433.2589 (17)160.9
Symmetry codes: (i) x, y, z+1; (ii) x+1, y+1, z+1; (iii) x, y+3/2, z+1/2; (iv) x1, y+3/2, z1/2.
 

References

First citationDeng, Q.-J., Yao, M.-X. & Zeng, M.-H. (2005). Acta Cryst. E61, o2239–o2240.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationDownie, T. C., Harrison, W., Raper, E. S. & Hepworth, M. A. (1971). Acta Cryst. B61, 1584–1590.  Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationJohn, S. (1962). US Patent 3033901.  Google Scholar
First citationJohn, S. & Gilmer, T. W. (1960). US Patent 2966495.  Google Scholar
First citationMa, C., Sun, J., Zheng, R. & Wang, D. (2007). Organomet. Chem. 692, 4029–4042.  CrossRef CAS Google Scholar
First citationRigaku/MSC (2006). PROCESS-AUTO. Rigaku/MSC, The Woodlands, Texas, USA.  Google Scholar
First citationRigaku/MSC. (2007). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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