




Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809051897/pk2208sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536809051897/pk2208Isup2.hkl |
CCDC reference: 766649
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(N-C) = 0.002 Å
- R factor = 0.026
- wR factor = 0.059
- Data-to-parameter ratio = 18.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT420_ALERT_2_B D-H Without Acceptor O1B - H203 ... ? PLAT420_ALERT_2_B D-H Without Acceptor O1B - H204 ... ?
Alert level C PLAT420_ALERT_2_C D-H Without Acceptor N1A - H1A1 ... ? PLAT420_ALERT_2_C D-H Without Acceptor N1B - H1B1 ... ? PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 4 PLAT041_ALERT_1_C Calc. and Reported SumFormula Strings Differ ? PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 3
Alert level G PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 4 PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) . 1.12 Ratio PLAT793_ALERT_4_G The Model has Chirality at N2A (Verify) .... S
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
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.
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).
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).
![]() | Fig. 1. The asymmetric unit of the title compound with the atomic labeling scheme. Displacement ellipsoids are drawn at the 40% probability level. |
![]() | Fig. 2. A partial packing diagram of title compound. |
Na+·C2H2N3S2−·2H2O | F(000) = 784 |
Mr = 191.21 | Dx = 1.710 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 11555 reflections |
a = 8.7810 (3) Å | θ = 3.0–27.4° |
b = 20.0593 (5) Å | µ = 0.72 mm−1 |
c = 8.4351 (3) Å | T = 296 K |
β = 91.026 (1)° | Block, colorless |
V = 1485.53 (8) Å3 | 0.38 × 0.28 × 0.17 mm |
Z = 8 |
Rigaku R-AXIS RAPID diffractometer | 3376 independent reflections |
Radiation source: rolling anode | 2974 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
Detector resolution: 10.00 pixels mm-1 | θmax = 27.4°, θmin = 3.1° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −25→25 |
Tmin = 0.758, Tmax = 0.885 | l = −10→10 |
14264 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.026 | H-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 reflections | Δρmax = 0.30 e Å−3 |
182 parameters | Δρmin = −0.32 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0516 (12) |
Na+·C2H2N3S2−·2H2O | V = 1485.53 (8) Å3 |
Mr = 191.21 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.7810 (3) Å | µ = 0.72 mm−1 |
b = 20.0593 (5) Å | T = 296 K |
c = 8.4351 (3) Å | 0.38 × 0.28 × 0.17 mm |
β = 91.026 (1)° |
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 = 0.885 | Rint = 0.026 |
14264 measured reflections |
R[F2 > 2σ(F2)] = 0.026 | 0 restraints |
wR(F2) = 0.059 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.30 e Å−3 |
3376 reflections | Δρmin = −0.32 e Å−3 |
182 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S2B | 0.46866 (5) | 0.720405 (18) | 0.04494 (5) | 0.03114 (11) | |
S2A | 0.97675 (5) | 0.708164 (18) | 0.53837 (5) | 0.03013 (10) | |
S1B | 0.71560 (5) | 0.66512 (2) | −0.16488 (6) | 0.03952 (12) | |
S1A | 1.23359 (5) | 0.65778 (2) | 0.75020 (5) | 0.03794 (12) | |
Na1B | 0.71086 (8) | 0.49937 (4) | 0.47238 (8) | 0.04359 (19) | |
Na1A | 0.98033 (7) | 0.50450 (3) | 0.20940 (8) | 0.03560 (16) | |
O2A | 0.70915 (13) | 0.49947 (6) | 0.18979 (14) | 0.0359 (3) | |
H104 | 0.6554 | 0.5221 | 0.1237 | 0.054* | |
H103 | 0.6897 | 0.4585 | 0.1699 | 0.054* | |
O1A | 0.99706 (15) | 0.58368 (6) | 0.00068 (15) | 0.0446 (3) | |
H101 | 1.0720 | 0.6080 | −0.0267 | 0.067* | |
H102 | 0.9227 | 0.6081 | −0.0358 | 0.067* | |
O2B | 0.75550 (13) | 0.50610 (6) | 0.74664 (14) | 0.0347 (3) | |
H204 | 0.5182 | 0.6062 | 0.4294 | 0.052* | |
H203 | 0.5156 | 0.6066 | 0.5812 | 0.052* | |
N2B | 0.41175 (17) | 0.60144 (7) | 0.13535 (18) | 0.0379 (3) | |
N2A | 0.93910 (16) | 0.58939 (6) | 0.43221 (16) | 0.0320 (3) | |
N3B | 0.53241 (16) | 0.59605 (7) | 0.03004 (17) | 0.0356 (3) | |
O1B | 0.50110 (17) | 0.57964 (7) | 0.50136 (16) | 0.0540 (4) | |
H201 | 0.7328 | 0.5460 | 0.7754 | 0.081* | |
H202 | 0.6964 | 0.4767 | 0.7880 | 0.081* | |
N3A | 1.05908 (15) | 0.58553 (6) | 0.54520 (15) | 0.0307 (3) | |
C2A | 0.88628 (18) | 0.65001 (7) | 0.41696 (18) | 0.0278 (3) | |
N1A | 0.76956 (18) | 0.66682 (7) | 0.31696 (18) | 0.0426 (4) | |
H1A1 | 0.7261 | 0.6368 | 0.2592 | 0.051* | |
H1A2 | 0.7391 | 0.7075 | 0.3114 | 0.051* | |
C1B | 0.57417 (17) | 0.65311 (7) | −0.02914 (18) | 0.0277 (3) | |
C2B | 0.36620 (18) | 0.66293 (8) | 0.15350 (18) | 0.0304 (3) | |
N1B | 0.24845 (18) | 0.67989 (8) | 0.2467 (2) | 0.0479 (4) | |
H1B1 | 0.2000 | 0.6496 | 0.2972 | 0.057* | |
H1B2 | 0.2221 | 0.7210 | 0.2554 | 0.057* | |
C1A | 1.09218 (17) | 0.64295 (7) | 0.61080 (17) | 0.0262 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S2B | 0.0345 (2) | 0.02059 (18) | 0.0384 (2) | −0.00051 (15) | 0.00191 (16) | 0.00096 (15) |
S2A | 0.0354 (2) | 0.02064 (18) | 0.0342 (2) | 0.00192 (15) | −0.00284 (16) | −0.00291 (15) |
S1B | 0.0396 (2) | 0.0309 (2) | 0.0485 (3) | 0.00355 (17) | 0.01226 (19) | 0.00579 (18) |
S1A | 0.0416 (2) | 0.0306 (2) | 0.0411 (2) | −0.00624 (17) | −0.01399 (18) | 0.00242 (17) |
Na1B | 0.0385 (4) | 0.0584 (5) | 0.0339 (4) | 0.0037 (3) | 0.0013 (3) | 0.0044 (3) |
Na1A | 0.0322 (3) | 0.0395 (4) | 0.0351 (3) | 0.0030 (3) | 0.0002 (3) | −0.0019 (3) |
O2A | 0.0390 (6) | 0.0304 (6) | 0.0380 (6) | 0.0020 (5) | −0.0086 (5) | −0.0004 (5) |
O1A | 0.0437 (7) | 0.0404 (7) | 0.0497 (7) | −0.0024 (6) | 0.0003 (6) | 0.0079 (6) |
O2B | 0.0352 (6) | 0.0321 (6) | 0.0370 (6) | −0.0011 (5) | 0.0036 (5) | 0.0002 (5) |
N2B | 0.0408 (8) | 0.0264 (7) | 0.0467 (8) | 0.0025 (6) | 0.0098 (6) | 0.0080 (6) |
N2A | 0.0395 (7) | 0.0238 (6) | 0.0323 (7) | 0.0009 (6) | −0.0083 (6) | −0.0022 (5) |
N3B | 0.0383 (8) | 0.0251 (7) | 0.0437 (8) | 0.0045 (6) | 0.0069 (6) | 0.0060 (6) |
O1B | 0.0642 (9) | 0.0502 (8) | 0.0478 (8) | 0.0032 (7) | 0.0073 (7) | 0.0103 (6) |
N3A | 0.0358 (7) | 0.0230 (6) | 0.0330 (7) | 0.0014 (5) | −0.0071 (6) | −0.0008 (5) |
C2A | 0.0318 (8) | 0.0251 (7) | 0.0266 (7) | −0.0002 (6) | −0.0001 (6) | −0.0010 (6) |
N1A | 0.0486 (9) | 0.0313 (7) | 0.0473 (9) | 0.0050 (6) | −0.0182 (7) | −0.0007 (6) |
C1B | 0.0284 (7) | 0.0240 (7) | 0.0304 (7) | 0.0020 (6) | −0.0050 (6) | 0.0014 (6) |
C2B | 0.0325 (8) | 0.0278 (8) | 0.0308 (8) | −0.0020 (6) | −0.0017 (6) | 0.0029 (6) |
N1B | 0.0521 (10) | 0.0336 (8) | 0.0588 (10) | 0.0017 (7) | 0.0236 (8) | 0.0014 (7) |
C1A | 0.0296 (7) | 0.0233 (7) | 0.0257 (7) | −0.0010 (6) | 0.0020 (6) | 0.0029 (6) |
S2B—C2B | 1.7340 (16) | O2B—Na1Aii | 2.3521 (13) |
S2B—C1B | 1.7583 (15) | O2B—H201 | 0.8609 |
S2A—C2A | 1.7354 (15) | O2B—H202 | 0.8632 |
S2A—C1A | 1.7578 (15) | N2B—C2B | 1.306 (2) |
S1B—C1B | 1.7211 (16) | N2B—N3B | 1.3989 (19) |
S1A—C1A | 1.7207 (16) | N2A—C2A | 1.3071 (19) |
Na1B—O2B | 2.3433 (13) | N2A—N3A | 1.4100 (18) |
Na1B—O2A | 2.3835 (13) | N3B—C1B | 1.304 (2) |
Na1B—O1Bi | 2.4576 (17) | O1B—Na1Bi | 2.4576 (17) |
Na1B—O1B | 2.4619 (16) | O1B—H204 | 0.8227 |
Na1B—Na1A | 3.2739 (10) | O1B—H203 | 0.8710 |
Na1A—O2Bii | 2.3521 (13) | N3A—C1A | 1.3082 (19) |
Na1A—O1A | 2.3776 (14) | N3A—Na1Bii | 2.6485 (15) |
Na1A—O2A | 2.3862 (14) | N3A—Na1Aii | 2.7735 (15) |
Na1A—O1Aiii | 2.5141 (15) | C2A—N1A | 1.358 (2) |
O2A—H104 | 0.8538 | N1A—H1A1 | 0.8600 |
O2A—H103 | 0.8559 | N1A—H1A2 | 0.8600 |
O1A—Na1Aiii | 2.5141 (15) | C2B—N1B | 1.354 (2) |
O1A—H101 | 0.8545 | N1B—H1B1 | 0.8600 |
O1A—H102 | 0.8684 | N1B—H1B2 | 0.8600 |
C2B—S2B—C1B | 87.65 (8) | Na1B—Na1A—Na1Aiii | 139.01 (3) |
C2A—S2A—C1A | 87.70 (7) | O2Bii—Na1A—Na1Bii | 36.27 (3) |
O2B—Na1B—O2A | 170.14 (5) | O1A—Na1A—Na1Bii | 119.10 (4) |
O2B—Na1B—O1Bi | 93.54 (5) | O2A—Na1A—Na1Bii | 138.61 (4) |
O2A—Na1B—O1Bi | 95.71 (5) | O1Aiii—Na1A—Na1Bii | 114.91 (4) |
O2B—Na1B—O1B | 88.66 (5) | N2A—Na1A—Na1Bii | 66.59 (3) |
O2A—Na1B—O1B | 96.17 (5) | N3Aii—Na1A—Na1Bii | 63.54 (3) |
O1Bi—Na1B—O1B | 81.01 (6) | Na1B—Na1A—Na1Bii | 92.07 (2) |
O2B—Na1B—N3Aii | 88.74 (5) | Na1Aiii—Na1A—Na1Bii | 128.47 (3) |
O2A—Na1B—N3Aii | 86.31 (5) | Na1B—O2A—Na1A | 86.69 (4) |
O1Bi—Na1B—N3Aii | 99.79 (5) | Na1B—O2A—H104 | 130.3 |
O1B—Na1B—N3Aii | 177.32 (5) | Na1A—O2A—H104 | 124.2 |
O2B—Na1B—N2A | 88.52 (5) | Na1B—O2A—H103 | 101.1 |
O2A—Na1B—N2A | 82.33 (4) | Na1A—O2A—H103 | 104.4 |
O1Bi—Na1B—N2A | 177.48 (5) | H104—O2A—H103 | 106.1 |
O1B—Na1B—N2A | 97.60 (5) | Na1A—O1A—Na1Aiii | 93.36 (5) |
N3Aii—Na1B—N2A | 81.70 (5) | Na1A—O1A—H101 | 129.8 |
O2B—Na1B—Na1A | 123.85 (4) | Na1Aiii—O1A—H101 | 98.1 |
O2A—Na1B—Na1A | 46.69 (3) | Na1A—O1A—H102 | 125.7 |
O1Bi—Na1B—Na1A | 129.72 (5) | Na1Aiii—O1A—H102 | 102.5 |
O1B—Na1B—Na1A | 126.71 (4) | H101—O1A—H102 | 99.2 |
N3Aii—Na1B—Na1A | 54.62 (3) | Na1B—O2B—Na1Aii | 107.31 (5) |
N2A—Na1B—Na1A | 49.64 (3) | Na1B—O2B—H201 | 107.3 |
O2B—Na1B—Na1Bi | 91.44 (4) | Na1Aii—O2B—H201 | 105.8 |
O2A—Na1B—Na1Bi | 97.82 (4) | Na1B—O2B—H202 | 105.6 |
O1Bi—Na1B—Na1Bi | 40.55 (4) | Na1Aii—O2B—H202 | 118.2 |
O1B—Na1B—Na1Bi | 40.46 (4) | H201—O2B—H202 | 112.2 |
N3Aii—Na1B—Na1Bi | 140.27 (5) | C2B—N2B—N3B | 112.60 (13) |
N2A—Na1B—Na1Bi | 138.02 (5) | C2A—N2A—N3A | 112.15 (12) |
Na1A—Na1B—Na1Bi | 144.42 (3) | C2A—N2A—Na1A | 126.84 (10) |
O2B—Na1B—Na1Aii | 36.43 (3) | N3A—N2A—Na1A | 110.19 (9) |
O2A—Na1B—Na1Aii | 134.54 (4) | C2A—N2A—Na1B | 111.62 (10) |
O1Bi—Na1B—Na1Aii | 117.21 (4) | N3A—N2A—Na1B | 114.97 (9) |
O1B—Na1B—Na1Aii | 118.11 (4) | Na1A—N2A—Na1B | 76.41 (4) |
N3Aii—Na1B—Na1Aii | 59.24 (3) | C1B—N3B—N2B | 113.37 (13) |
N2A—Na1B—Na1Aii | 65.29 (3) | Na1Bi—O1B—Na1B | 98.99 (6) |
Na1A—Na1B—Na1Aii | 87.93 (2) | Na1Bi—O1B—H204 | 129.2 |
Na1Bi—Na1B—Na1Aii | 127.63 (3) | Na1B—O1B—H204 | 101.7 |
O2Bii—Na1A—O1A | 95.93 (5) | Na1Bi—O1B—H203 | 115.5 |
O2Bii—Na1A—O2A | 170.82 (5) | Na1B—O1B—H203 | 112.5 |
O1A—Na1A—O2A | 92.97 (5) | H204—O1B—H203 | 98.3 |
O2Bii—Na1A—O1Aiii | 87.56 (5) | C1A—N3A—N2A | 113.29 (12) |
O1A—Na1A—O1Aiii | 86.64 (5) | C1A—N3A—Na1Bii | 115.21 (10) |
O2A—Na1A—O1Aiii | 90.73 (5) | N2A—N3A—Na1Bii | 123.97 (9) |
O2Bii—Na1A—N2A | 95.52 (5) | C1A—N3A—Na1Aii | 106.70 (10) |
O1A—Na1A—N2A | 96.34 (5) | N2A—N3A—Na1Aii | 116.01 (9) |
O2A—Na1A—N2A | 85.71 (5) | Na1Bii—N3A—Na1Aii | 74.25 (4) |
O1Aiii—Na1A—N2A | 175.46 (5) | N2A—C2A—N1A | 123.68 (14) |
O2Bii—Na1A—N3Aii | 87.67 (4) | N2A—C2A—S2A | 114.17 (11) |
O1A—Na1A—N3Aii | 176.24 (5) | N1A—C2A—S2A | 122.15 (12) |
O2A—Na1A—N3Aii | 83.48 (4) | C2A—N1A—H1A1 | 120.0 |
O1Aiii—Na1A—N3Aii | 94.61 (4) | C2A—N1A—H1A2 | 120.0 |
N2A—Na1A—N3Aii | 82.20 (4) | H1A1—N1A—H1A2 | 120.0 |
O2Bii—Na1A—Na1B | 127.81 (4) | N3B—C1B—S1B | 126.07 (12) |
O1A—Na1A—Na1B | 125.29 (4) | N3B—C1B—S2B | 112.60 (12) |
O2A—Na1A—Na1B | 46.62 (3) | S1B—C1B—S2B | 121.34 (9) |
O1Aiii—Na1A—Na1B | 121.51 (4) | N2B—C2B—N1B | 122.96 (15) |
N2A—Na1A—Na1B | 53.95 (4) | N2B—C2B—S2B | 113.76 (12) |
N3Aii—Na1A—Na1B | 51.13 (3) | N1B—C2B—S2B | 123.27 (13) |
O2Bii—Na1A—Na1Aiii | 92.23 (4) | C2B—N1B—H1B1 | 120.0 |
O1A—Na1A—Na1Aiii | 44.83 (4) | C2B—N1B—H1B2 | 120.0 |
O2A—Na1A—Na1Aiii | 92.49 (4) | H1B1—N1B—H1B2 | 120.0 |
O1Aiii—Na1A—Na1Aiii | 41.81 (3) | N3A—C1A—S1A | 126.40 (12) |
N2A—Na1A—Na1Aiii | 141.05 (5) | N3A—C1A—S2A | 112.69 (11) |
N3Aii—Na1A—Na1Aiii | 136.32 (4) | S1A—C1A—S2A | 120.89 (9) |
O2B—Na1B—Na1A—O2Bii | 13.17 (9) | Na1A—Na1B—O2B—Na1Aii | −10.87 (7) |
O2A—Na1B—Na1A—O2Bii | −170.38 (7) | Na1Bi—Na1B—O2B—Na1Aii | 173.99 (4) |
O1Bi—Na1B—Na1A—O2Bii | −117.66 (7) | O2Bii—Na1A—N2A—C2A | 119.25 (13) |
O1B—Na1B—Na1A—O2Bii | 130.87 (7) | O1A—Na1A—N2A—C2A | 22.63 (14) |
N3Aii—Na1B—Na1A—O2Bii | −46.25 (6) | O2A—Na1A—N2A—C2A | −69.88 (14) |
N2A—Na1B—Na1A—O2Bii | 65.53 (6) | N3Aii—Na1A—N2A—C2A | −153.88 (14) |
Na1Bi—Na1B—Na1A—O2Bii | −175.20 (6) | Na1B—Na1A—N2A—C2A | −107.01 (14) |
Na1Aii—Na1B—Na1A—O2Bii | 6.74 (5) | Na1Aiii—Na1A—N2A—C2A | 18.77 (17) |
O2B—Na1B—Na1A—O1A | −122.01 (6) | Na1Bii—Na1A—N2A—C2A | 141.65 (14) |
O2A—Na1B—Na1A—O1A | 54.43 (6) | O2Bii—Na1A—N2A—N3A | −21.79 (10) |
O1Bi—Na1B—Na1A—O1A | 107.16 (7) | O1A—Na1A—N2A—N3A | −118.40 (10) |
O1B—Na1B—Na1A—O1A | −4.31 (8) | O2A—Na1A—N2A—N3A | 149.09 (10) |
N3Aii—Na1B—Na1A—O1A | 178.56 (6) | N3Aii—Na1A—N2A—N3A | 65.09 (10) |
N2A—Na1B—Na1A—O1A | −69.65 (6) | Na1B—Na1A—N2A—N3A | 111.96 (10) |
Na1Bi—Na1B—Na1A—O1A | 49.61 (9) | Na1Aiii—Na1A—N2A—N3A | −122.26 (9) |
Na1Aii—Na1B—Na1A—O1A | −128.44 (5) | Na1Bii—Na1A—N2A—N3A | 0.61 (8) |
O2B—Na1B—Na1A—O2A | −176.45 (7) | O2Bii—Na1A—N2A—Na1B | −133.74 (4) |
O1Bi—Na1B—Na1A—O2A | 52.73 (7) | O1A—Na1A—N2A—Na1B | 129.64 (4) |
O1B—Na1B—Na1A—O2A | −58.74 (7) | O2A—Na1A—N2A—Na1B | 37.13 (4) |
N3Aii—Na1B—Na1A—O2A | 124.13 (6) | N3Aii—Na1A—N2A—Na1B | −46.86 (4) |
N2A—Na1B—Na1A—O2A | −124.09 (6) | Na1Aiii—Na1A—N2A—Na1B | 125.78 (6) |
Na1Bi—Na1B—Na1A—O2A | −4.82 (7) | Na1Bii—Na1A—N2A—Na1B | −111.34 (3) |
Na1Aii—Na1B—Na1A—O2A | 177.12 (5) | O2B—Na1B—N2A—C2A | −96.54 (11) |
O2B—Na1B—Na1A—O1Aiii | 127.53 (6) | O2A—Na1B—N2A—C2A | 87.15 (11) |
O2A—Na1B—Na1A—O1Aiii | −56.03 (6) | O1B—Na1B—N2A—C2A | −8.10 (11) |
O1Bi—Na1B—Na1A—O1Aiii | −3.30 (8) | N3Aii—Na1B—N2A—C2A | 174.51 (11) |
O1B—Na1B—Na1A—O1Aiii | −114.77 (7) | Na1A—Na1B—N2A—C2A | 124.59 (11) |
N3Aii—Na1B—Na1A—O1Aiii | 68.10 (6) | Na1Bi—Na1B—N2A—C2A | −6.04 (14) |
N2A—Na1B—Na1A—O1Aiii | 179.89 (6) | Na1Aii—Na1B—N2A—C2A | −125.60 (11) |
Na1Bi—Na1B—Na1A—O1Aiii | −60.85 (8) | O2B—Na1B—N2A—N3A | 32.66 (10) |
Na1Aii—Na1B—Na1A—O1Aiii | 121.10 (5) | O2A—Na1B—N2A—N3A | −143.65 (10) |
O2B—Na1B—Na1A—N2A | −52.36 (6) | O1B—Na1B—N2A—N3A | 121.10 (10) |
O2A—Na1B—Na1A—N2A | 124.09 (6) | N3Aii—Na1B—N2A—N3A | −56.29 (11) |
O1Bi—Na1B—Na1A—N2A | 176.81 (7) | Na1A—Na1B—N2A—N3A | −106.21 (10) |
O1B—Na1B—Na1A—N2A | 65.34 (7) | Na1Bi—Na1B—N2A—N3A | 123.16 (10) |
N3Aii—Na1B—Na1A—N2A | −111.79 (5) | Na1Aii—Na1B—N2A—N3A | 3.60 (9) |
Na1Bi—Na1B—Na1A—N2A | 119.27 (8) | O2B—Na1B—N2A—Na1A | 138.86 (4) |
Na1Aii—Na1B—Na1A—N2A | −58.79 (4) | O2A—Na1B—N2A—Na1A | −37.45 (4) |
O2B—Na1B—Na1A—N3Aii | 59.43 (6) | O1B—Na1B—N2A—Na1A | −132.69 (5) |
O2A—Na1B—Na1A—N3Aii | −124.13 (6) | N3Aii—Na1B—N2A—Na1A | 49.92 (4) |
O1Bi—Na1B—Na1A—N3Aii | −71.40 (6) | Na1Bi—Na1B—N2A—Na1A | −130.63 (6) |
O1B—Na1B—Na1A—N3Aii | 177.13 (7) | Na1Aii—Na1B—N2A—Na1A | 109.80 (3) |
N2A—Na1B—Na1A—N3Aii | 111.79 (5) | C2B—N2B—N3B—C1B | −0.4 (2) |
Na1Bi—Na1B—Na1A—N3Aii | −128.95 (8) | O2B—Na1B—O1B—Na1Bi | −93.80 (5) |
Na1Aii—Na1B—Na1A—N3Aii | 52.99 (4) | O2A—Na1B—O1B—Na1Bi | 94.83 (5) |
O2B—Na1B—Na1A—Na1Aiii | 178.67 (5) | O1Bi—Na1B—O1B—Na1Bi | 0.0 |
O2A—Na1B—Na1A—Na1Aiii | −4.89 (6) | N2A—Na1B—O1B—Na1Bi | 177.88 (5) |
O1Bi—Na1B—Na1A—Na1Aiii | 47.84 (8) | Na1A—Na1B—O1B—Na1Bi | 133.56 (5) |
O1B—Na1B—Na1A—Na1Aiii | −63.63 (8) | Na1Aii—Na1B—O1B—Na1Bi | −116.13 (5) |
N3Aii—Na1B—Na1A—Na1Aiii | 119.24 (6) | C2A—N2A—N3A—C1A | 0.06 (19) |
N2A—Na1B—Na1A—Na1Aiii | −128.97 (7) | Na1A—N2A—N3A—C1A | 147.14 (11) |
Na1Bi—Na1B—Na1A—Na1Aiii | −9.71 (10) | Na1B—N2A—N3A—C1A | −128.88 (11) |
Na1Aii—Na1B—Na1A—Na1Aiii | 172.24 (6) | C2A—N2A—N3A—Na1Bii | −148.06 (11) |
O2B—Na1B—Na1A—Na1Bii | 6.43 (4) | Na1A—N2A—N3A—Na1Bii | −0.97 (13) |
O2A—Na1B—Na1A—Na1Bii | −177.12 (5) | Na1B—N2A—N3A—Na1Bii | 83.01 (11) |
O1Bi—Na1B—Na1A—Na1Bii | −124.39 (6) | C2A—N2A—N3A—Na1Aii | 123.98 (12) |
O1B—Na1B—Na1A—Na1Bii | 124.14 (6) | Na1A—N2A—N3A—Na1Aii | −88.94 (9) |
N3Aii—Na1B—Na1A—Na1Bii | −52.99 (4) | Na1B—N2A—N3A—Na1Aii | −4.96 (12) |
N2A—Na1B—Na1A—Na1Bii | 58.79 (4) | N3A—N2A—C2A—N1A | −179.29 (15) |
Na1Bi—Na1B—Na1A—Na1Bii | 178.06 (7) | Na1A—N2A—C2A—N1A | 40.3 (2) |
Na1Aii—Na1B—Na1A—Na1Bii | 0.0 | Na1B—N2A—C2A—N1A | −48.62 (19) |
O1Bi—Na1B—O2A—Na1A | −142.04 (5) | N3A—N2A—C2A—S2A | −0.11 (17) |
O1B—Na1B—O2A—Na1A | 136.43 (5) | Na1A—N2A—C2A—S2A | −140.52 (9) |
N3Aii—Na1B—O2A—Na1A | −42.56 (4) | Na1B—N2A—C2A—S2A | 130.56 (8) |
N2A—Na1B—O2A—Na1A | 39.55 (4) | C1A—S2A—C2A—N2A | 0.09 (13) |
Na1Bi—Na1B—O2A—Na1A | 177.17 (4) | C1A—S2A—C2A—N1A | 179.29 (15) |
Na1Aii—Na1B—O2A—Na1A | −4.04 (7) | N2B—N3B—C1B—S1B | −178.64 (12) |
O1A—Na1A—O2A—Na1B | −138.33 (5) | N2B—N3B—C1B—S2B | 1.37 (18) |
O1Aiii—Na1A—O2A—Na1B | 135.00 (4) | C2B—S2B—C1B—N3B | −1.48 (13) |
N2A—Na1A—O2A—Na1B | −42.18 (4) | C2B—S2B—C1B—S1B | 178.53 (10) |
N3Aii—Na1A—O2A—Na1B | 40.44 (4) | N3B—N2B—C2B—N1B | 178.31 (16) |
Na1Aiii—Na1A—O2A—Na1B | 176.79 (4) | N3B—N2B—C2B—S2B | −0.78 (19) |
Na1Bii—Na1A—O2A—Na1B | 4.35 (7) | C1B—S2B—C2B—N2B | 1.26 (13) |
O2Bii—Na1A—O1A—Na1Aiii | 87.19 (5) | C1B—S2B—C2B—N1B | −177.82 (16) |
O2A—Na1A—O1A—Na1Aiii | −90.55 (5) | N2A—N3A—C1A—S1A | −178.68 (11) |
O1Aiii—Na1A—O1A—Na1Aiii | 0.0 | Na1Bii—N3A—C1A—S1A | −27.64 (17) |
N2A—Na1A—O1A—Na1Aiii | −176.56 (5) | Na1Aii—N3A—C1A—S1A | 52.46 (15) |
Na1B—Na1A—O1A—Na1Aiii | −126.85 (5) | N2A—N3A—C1A—S2A | 0.01 (17) |
Na1Bii—Na1A—O1A—Na1Aiii | 116.75 (4) | Na1Bii—N3A—C1A—S2A | 151.06 (7) |
O1Bi—Na1B—O2B—Na1Aii | 133.46 (6) | Na1Aii—N3A—C1A—S2A | −128.85 (8) |
O1B—Na1B—O2B—Na1Aii | −145.64 (5) | C2A—S2A—C1A—N3A | −0.06 (12) |
N3Aii—Na1B—O2B—Na1Aii | 33.73 (5) | C2A—S2A—C1A—S1A | 178.72 (10) |
N2A—Na1B—O2B—Na1Aii | −48.00 (5) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+1; (iii) −x+2, −y+1, −z. |
D—H···A | D—H | H···A | D···A | 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···S1Biv | 0.86 | 2.45 | 3.2962 (12) | 169 |
O2B—H202···N2Bi | 0.86 | 1.95 | 2.8024 (18) | 170 |
N1A—H1A2···S1Bv | 0.86 | 2.57 | 3.4081 (16) | 165 |
N1B—H1B2···S1Avi | 0.86 | 2.43 | 3.2589 (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) x−1, −y+3/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | Na+·C2H2N3S2−·2H2O |
Mr | 191.21 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 8.7810 (3), 20.0593 (5), 8.4351 (3) |
β (°) | 91.026 (1) |
V (Å3) | 1485.53 (8) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.72 |
Crystal size (mm) | 0.38 × 0.28 × 0.17 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.758, 0.885 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14264, 3376, 2974 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.648 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.026, 0.059, 1.00 |
No. of reflections | 3376 |
No. of parameters | 182 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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).
D—H···A | D—H | H···A | D···A | D—H···A |
O2A—H104···N3B | 0.85 | 1.99 | 2.8113 (18) | 160.8 |
O1A—H102···S1B | 0.87 | 2.39 | 3.2563 (14) | 172.4 |
O2B—H201···S1Bi | 0.86 | 2.45 | 3.2962 (12) | 168.9 |
O2B—H202···N2Bii | 0.86 | 1.95 | 2.8024 (18) | 169.5 |
N1A—H1A2···S1Biii | 0.86 | 2.57 | 3.4081 (16) | 164.6 |
N1B—H1B2···S1Aiv | 0.86 | 2.43 | 3.2589 (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) x−1, −y+3/2, z−1/2. |
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.