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In the title compound, CH6N3S+·C6H2N3O7·H2O, the components are linked by a number of N—H...O and O—H...O hydrogen bonds into a complex three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024002/cs2034sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024002/cs2034Isup2.hkl
Contains datablock I

CCDC reference: 651476

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.044
  • wR factor = 0.137
  • Data-to-parameter ratio = 10.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 4 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N3 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.19
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Thiosemicarbazidium picrate monohydrate top
Crystal data top
CH6N3S+·C6H2N3O7·H2OZ = 2
Mr = 338.27F(000) = 348
Triclinic, P1Dx = 1.729 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.1686 (5) ÅCell parameters from 2882 reflections
b = 9.7720 (6) Åθ = 2.3–28.2°
c = 10.3293 (7) ŵ = 0.31 mm1
α = 94.904 (1)°T = 298 K
β = 104.613 (1)°Block, yellow
γ = 109.257 (1)°0.26 × 0.20 × 0.18 mm
V = 649.63 (7) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2377 independent reflections
Radiation source: fine focus sealed Siemens Mo tube2198 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
0.3° wide ω exposures scansθmax = 25.5°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 88
Tmin = 0.925, Tmax = 0.941k = 1111
3394 measured reflectionsl = 1212
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)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.137 w = 1/[σ2(Fo2) + (0.0815P)2 + 0.303P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
2377 reflectionsΔρmax = 0.50 e Å3
224 parametersΔρmin = 0.34 e Å3
2 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.023 (6)
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 > σ(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
C10.7217 (3)1.0036 (2)0.9487 (2)0.0310 (4)
C20.6338 (3)0.8454 (2)0.9004 (2)0.0309 (5)
C30.4940 (3)0.7776 (2)0.7758 (2)0.0306 (4)
H30.44300.67550.75040.037*
C40.4295 (3)0.8635 (2)0.6879 (2)0.0290 (4)
C50.5022 (3)1.0161 (2)0.7239 (2)0.0294 (4)
H50.45661.07230.66410.035*
C60.6425 (3)1.0824 (2)0.8494 (2)0.0297 (4)
C70.1282 (3)0.2038 (2)0.3676 (2)0.0314 (5)
N10.6970 (3)0.7500 (2)0.98778 (19)0.0377 (4)
N20.2821 (3)0.79158 (19)0.55577 (17)0.0329 (4)
N30.7130 (3)1.24264 (19)0.88155 (18)0.0360 (4)
N40.0429 (3)0.0590 (2)0.3301 (2)0.0414 (5)
H4A0.076 (4)0.003 (3)0.380 (3)0.050*
H4B0.046 (5)0.017 (3)0.243 (3)0.050*
N50.0602 (3)0.2791 (2)0.2747 (2)0.0387 (5)
H5A0.012 (4)0.236 (3)0.201 (3)0.046*
N60.1520 (4)0.4336 (2)0.2989 (2)0.0425 (5)
H6A0.054 (5)0.472 (4)0.283 (3)0.064*
H6B0.226 (5)0.459 (3)0.388 (3)0.051*
H6C0.225 (5)0.464 (3)0.246 (3)0.051*
O10.8552 (3)1.06350 (18)1.06062 (17)0.0507 (5)
O20.7553 (4)0.7902 (2)1.11078 (18)0.0688 (7)
O30.6863 (3)0.62910 (18)0.93507 (19)0.0516 (5)
O40.2037 (3)0.65628 (17)0.53171 (17)0.0463 (4)
O50.2423 (3)0.86815 (19)0.47271 (16)0.0470 (5)
O60.8105 (4)1.3081 (2)0.9962 (2)0.0800 (8)
O70.6669 (4)1.30720 (19)0.7905 (2)0.0677 (7)
O80.1514 (3)0.4540 (2)0.7612 (2)0.0579 (5)
H8A0.152 (6)0.384 (3)0.712 (3)0.087*
H8B0.164 (6)0.435 (4)0.8373 (19)0.087*
S10.30307 (9)0.28907 (7)0.51999 (6)0.0434 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0349 (11)0.0295 (10)0.0264 (10)0.0123 (8)0.0052 (8)0.0032 (8)
C20.0348 (11)0.0282 (10)0.0315 (10)0.0140 (8)0.0086 (8)0.0093 (8)
C30.0337 (11)0.0241 (9)0.0325 (10)0.0098 (8)0.0089 (8)0.0040 (8)
C40.0291 (10)0.0282 (10)0.0275 (10)0.0099 (8)0.0058 (8)0.0035 (8)
C50.0315 (10)0.0292 (10)0.0287 (10)0.0120 (8)0.0086 (8)0.0092 (8)
C60.0339 (10)0.0236 (10)0.0303 (10)0.0088 (8)0.0096 (8)0.0051 (8)
C70.0318 (10)0.0349 (11)0.0304 (10)0.0163 (9)0.0084 (8)0.0064 (8)
N10.0465 (11)0.0301 (9)0.0352 (10)0.0153 (8)0.0068 (8)0.0103 (8)
N20.0327 (9)0.0339 (9)0.0294 (9)0.0129 (7)0.0050 (7)0.0022 (7)
N30.0412 (10)0.0261 (9)0.0354 (10)0.0101 (8)0.0058 (8)0.0054 (8)
N40.0506 (12)0.0317 (10)0.0361 (11)0.0153 (9)0.0017 (9)0.0089 (8)
N50.0529 (12)0.0256 (9)0.0287 (9)0.0141 (8)0.0015 (8)0.0017 (7)
N60.0552 (13)0.0279 (10)0.0392 (11)0.0147 (9)0.0063 (10)0.0051 (8)
O10.0647 (12)0.0334 (9)0.0356 (9)0.0142 (8)0.0098 (8)0.0005 (7)
O20.1191 (19)0.0460 (10)0.0338 (10)0.0346 (11)0.0024 (10)0.0129 (8)
O30.0739 (13)0.0356 (9)0.0514 (10)0.0303 (9)0.0137 (9)0.0124 (8)
O40.0525 (10)0.0314 (8)0.0395 (9)0.0077 (7)0.0012 (7)0.0037 (7)
O50.0566 (11)0.0464 (10)0.0328 (8)0.0223 (8)0.0006 (7)0.0087 (7)
O60.125 (2)0.0314 (9)0.0478 (11)0.0219 (11)0.0211 (12)0.0062 (8)
O70.0979 (17)0.0291 (9)0.0525 (11)0.0129 (9)0.0057 (11)0.0138 (8)
O80.0734 (13)0.0447 (10)0.0546 (12)0.0277 (10)0.0073 (10)0.0144 (9)
S10.0446 (4)0.0451 (4)0.0327 (3)0.0186 (3)0.0026 (2)0.0009 (2)
Geometric parameters (Å, º) top
C1—O11.246 (3)N1—O21.217 (3)
C1—C61.448 (3)N1—O31.228 (3)
C1—C21.450 (3)N2—O51.226 (2)
C2—C31.366 (3)N2—O41.228 (2)
C2—N11.451 (3)N3—O61.207 (3)
C3—C41.385 (3)N3—O71.214 (2)
C3—H30.9300N4—H4A0.83 (3)
C4—C51.388 (3)N4—H4B0.92 (3)
C4—N21.446 (3)N5—N61.404 (3)
C5—C61.371 (3)N5—H5A0.79 (3)
C5—H50.9300N6—H6A0.89 (4)
C6—N31.457 (3)N6—H6B0.90 (3)
C7—N41.319 (3)N6—H6C0.85 (3)
C7—N51.349 (3)O8—H8A0.82 (3)
C7—S11.684 (2)O8—H8B0.82 (3)
O1—C1—C6124.59 (19)O2—N1—C2119.50 (19)
O1—C1—C2123.32 (19)O3—N1—C2118.72 (18)
C6—C1—C2112.04 (18)O5—N2—O4123.07 (18)
C3—C2—C1124.41 (18)O5—N2—C4118.61 (17)
C3—C2—N1116.46 (18)O4—N2—C4118.31 (17)
C1—C2—N1119.12 (18)O6—N3—O7121.47 (19)
C2—C3—C4118.88 (18)O6—N3—C6120.55 (18)
C2—C3—H3120.6O7—N3—C6117.96 (18)
C4—C3—H3120.6C7—N4—H4A122 (2)
C3—C4—C5121.60 (18)C7—N4—H4B120.2 (17)
C3—C4—N2118.80 (18)H4A—N4—H4B118 (3)
C5—C4—N2119.60 (18)C7—N5—N6119.43 (19)
C6—C5—C4118.78 (18)C7—N5—H5A119 (2)
C6—C5—H5120.6N6—N5—H5A120 (2)
C4—C5—H5120.6N5—N6—H6A109 (2)
C5—C6—C1124.27 (18)N5—N6—H6B104.7 (18)
C5—C6—N3116.31 (17)H6A—N6—H6B111 (3)
C1—C6—N3119.42 (18)N5—N6—H6C112 (2)
N4—C7—N5114.47 (19)H6A—N6—H6C106 (3)
N4—C7—S1123.27 (17)H6B—N6—H6C113 (3)
N5—C7—S1122.24 (16)H8A—O8—H8B108 (4)
O2—N1—O3121.76 (19)
O1—C1—C2—C3177.1 (2)C2—C1—C6—N3179.47 (17)
C6—C1—C2—C30.5 (3)C3—C2—N1—O2153.2 (2)
O1—C1—C2—N12.4 (3)C1—C2—N1—O227.3 (3)
C6—C1—C2—N1179.97 (18)C3—C2—N1—O325.4 (3)
C1—C2—C3—C40.0 (3)C1—C2—N1—O3154.1 (2)
N1—C2—C3—C4179.54 (18)C3—C4—N2—O5172.19 (18)
C2—C3—C4—C50.5 (3)C5—C4—N2—O58.0 (3)
C2—C3—C4—N2179.74 (18)C3—C4—N2—O47.3 (3)
C3—C4—C5—C60.5 (3)C5—C4—N2—O4172.49 (19)
N2—C4—C5—C6179.73 (17)C5—C6—N3—O6168.4 (2)
C4—C5—C6—C10.0 (3)C1—C6—N3—O611.5 (3)
C4—C5—C6—N3179.92 (18)C5—C6—N3—O710.0 (3)
O1—C1—C6—C5177.0 (2)C1—C6—N3—O7170.1 (2)
C2—C1—C6—C50.5 (3)N4—C7—N5—N6175.0 (2)
O1—C1—C6—N33.0 (3)S1—C7—N5—N66.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O80.932.503.266 (3)140
O8—H8A···S10.82 (3)2.72 (2)3.439 (2)148 (4)
N6—H6B···O40.90 (3)2.41 (3)2.963 (3)120 (2)
N6—H6B···S10.90 (3)2.35 (3)2.948 (2)124 (2)
O8—H8B···O2i0.82 (3)2.52 (3)3.006 (3)120 (3)
O8—H8B···O3i0.82 (3)2.55 (2)3.328 (3)161 (4)
N6—H6C···O7ii0.85 (3)2.21 (3)2.791 (3)125 (2)
N6—H6C···O3iii0.85 (3)2.33 (3)3.031 (3)140 (3)
N6—H6A···O8iv0.89 (4)1.82 (4)2.708 (3)176 (3)
N5—H5A···O6v0.79 (3)2.46 (3)3.072 (3)134 (3)
N5—H5A···O1v0.79 (3)1.92 (3)2.647 (2)153 (3)
N4—H4B···O2v0.92 (3)2.29 (3)3.056 (3)140 (2)
N4—H4B···O1v0.92 (3)1.99 (3)2.781 (3)143 (2)
N4—H4A···O5vi0.83 (3)2.18 (3)2.976 (3)160 (3)
Symmetry codes: (i) x+1, y+1, z+2; (ii) x+1, y+2, z+1; (iii) x+1, y+1, z+1; (iv) x, y+1, z+1; (v) x1, y1, z1; (vi) x, y1, z.
 

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