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In the title compound, C12H10N8O2S·H2O, the thione-substituted triazole ring is coplanar with the benzene ring; it forms a dihedral angle of 86.42 (6)° with the other triazole ring. Inter­molecular O—H...N and N—H...O hydrogen bonds link the mol­ecules into sheets parallel to (010).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807000037/ci2263sup1.cif
Contains datablocks 50128B, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807000037/ci2263Isup2.hkl
Contains datablock I

CCDC reference: 636205

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.043
  • wR factor = 0.125
  • Data-to-parameter ratio = 15.7

checkCIF/PLATON results

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Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.68 mm PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N8 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2001); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXL97.

(I) top
Crystal data top
C12H10N8O2S·H2OF(000) = 720
Mr = 348.37Dx = 1.496 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 14545 reflections
a = 8.1883 (16) Åθ = 1.6–27.5°
b = 24.938 (5) ŵ = 0.24 mm1
c = 7.5896 (15) ÅT = 293 K
β = 93.56 (3)°Plate, colourless
V = 1546.8 (5) Å30.68 × 0.68 × 0.07 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID IP area-detector
diffractometer
3525 independent reflections
Radiation source: Rotating Anode2454 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1010
Tmin = 0.853, Tmax = 0.984k = 3232
14545 measured reflectionsl = 99
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0672P)2]
where P = (Fo2 + 2Fc2)/3
3525 reflections(Δ/σ)max = 0.001
225 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.23 e Å3
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
S10.50498 (8)0.57348 (2)0.48086 (7)0.05184 (18)
O11.0814 (4)0.35604 (11)1.2682 (4)0.1302 (11)
O21.0145 (3)0.40299 (12)1.4878 (4)0.1152 (9)
N10.6462 (2)0.69082 (6)1.1192 (2)0.0430 (4)
N20.6988 (3)0.73357 (8)1.0295 (3)0.0699 (6)
N30.9021 (3)0.69839 (8)1.2036 (2)0.0559 (5)
N40.3596 (2)0.68576 (7)0.7878 (2)0.0436 (4)
N50.3697 (2)0.65906 (6)0.6313 (2)0.0422 (4)
H5A0.32010.66950.53420.051*
N60.51264 (18)0.61385 (6)0.82115 (19)0.0356 (3)
N70.60291 (19)0.57820 (6)0.9267 (2)0.0392 (4)
N81.0113 (3)0.39316 (11)1.3304 (4)0.0803 (8)
C10.8518 (4)0.73615 (11)1.0843 (3)0.0706 (8)
H1A0.92200.76221.04430.085*
C20.7675 (3)0.67101 (8)1.2218 (3)0.0474 (5)
H2A0.75870.64171.29660.057*
C30.4801 (2)0.67234 (9)1.0890 (3)0.0452 (5)
H3B0.40520.70031.12110.054*
H3C0.46260.64131.16240.054*
C40.4470 (2)0.65796 (8)0.9009 (2)0.0376 (4)
C50.4635 (2)0.61532 (7)0.6431 (2)0.0359 (4)
C60.6567 (2)0.53524 (8)0.8636 (3)0.0413 (4)
H6A0.63960.52720.74420.050*
C70.7474 (2)0.49836 (8)0.9851 (3)0.0399 (4)
C80.8153 (3)0.45192 (8)0.9197 (3)0.0502 (5)
H8A0.80270.44420.79980.060*
C90.9019 (3)0.41706 (9)1.0333 (4)0.0571 (6)
H9A0.94880.38610.99080.069*
C100.9167 (3)0.42927 (9)1.2087 (3)0.0533 (6)
C110.8487 (3)0.47425 (10)1.2777 (3)0.0560 (6)
H11A0.85930.48121.39830.067*
C120.7646 (3)0.50880 (9)1.1642 (3)0.0496 (5)
H12A0.71850.53971.20850.060*
O1W0.2087 (2)0.71050 (7)0.3670 (2)0.0602 (5)
H2WA0.245 (4)0.7429 (15)0.339 (5)0.105 (12)*
H1WA0.107 (5)0.7072 (13)0.325 (4)0.099 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0768 (4)0.0433 (3)0.0351 (3)0.0035 (3)0.0006 (2)0.0033 (2)
O10.144 (2)0.0882 (17)0.156 (3)0.0619 (17)0.0104 (19)0.0415 (17)
O20.1151 (19)0.128 (2)0.0976 (18)0.0230 (16)0.0294 (15)0.0543 (16)
N10.0582 (10)0.0370 (8)0.0323 (8)0.0003 (8)0.0085 (7)0.0004 (7)
N20.0873 (16)0.0593 (13)0.0598 (13)0.0186 (11)0.0218 (11)0.0202 (10)
N30.0600 (11)0.0580 (11)0.0477 (10)0.0092 (10)0.0121 (9)0.0000 (9)
N40.0474 (10)0.0412 (9)0.0412 (9)0.0057 (7)0.0058 (7)0.0013 (7)
N50.0509 (9)0.0388 (8)0.0354 (8)0.0034 (8)0.0085 (7)0.0001 (7)
N60.0389 (8)0.0348 (8)0.0328 (8)0.0025 (7)0.0019 (6)0.0011 (6)
N70.0412 (9)0.0388 (9)0.0372 (8)0.0031 (7)0.0020 (7)0.0071 (7)
N80.0632 (14)0.0731 (16)0.102 (2)0.0003 (12)0.0112 (14)0.0459 (15)
C10.0870 (19)0.0697 (17)0.0526 (14)0.0288 (15)0.0163 (13)0.0144 (13)
C20.0583 (13)0.0424 (11)0.0400 (10)0.0014 (10)0.0094 (9)0.0029 (9)
C30.0483 (11)0.0494 (12)0.0375 (10)0.0071 (9)0.0006 (9)0.0045 (9)
C40.0371 (9)0.0367 (10)0.0383 (10)0.0026 (8)0.0017 (8)0.0011 (8)
C50.0394 (10)0.0348 (9)0.0329 (9)0.0056 (8)0.0015 (7)0.0040 (8)
C60.0443 (11)0.0419 (10)0.0375 (10)0.0026 (9)0.0010 (8)0.0028 (8)
C70.0363 (9)0.0384 (10)0.0451 (11)0.0003 (8)0.0020 (8)0.0073 (8)
C80.0542 (12)0.0429 (11)0.0536 (12)0.0070 (10)0.0042 (10)0.0008 (10)
C90.0510 (13)0.0416 (12)0.0791 (17)0.0096 (10)0.0061 (12)0.0094 (11)
C100.0394 (11)0.0495 (12)0.0703 (15)0.0021 (10)0.0018 (10)0.0268 (12)
C110.0554 (13)0.0653 (15)0.0468 (12)0.0015 (11)0.0011 (10)0.0164 (11)
C120.0544 (12)0.0501 (12)0.0443 (11)0.0074 (10)0.0023 (10)0.0063 (10)
O1W0.0513 (10)0.0583 (10)0.0688 (11)0.0041 (8)0.0144 (8)0.0223 (9)
Geometric parameters (Å, º) top
S1—C51.6647 (19)C2—H2A0.93
O1—N81.201 (4)C3—C41.481 (3)
O2—N81.218 (4)C3—H3B0.97
N1—C21.320 (3)C3—H3C0.97
N1—N21.350 (2)C6—C71.471 (3)
N1—C31.440 (3)C6—H6A0.93
N2—C11.297 (3)C7—C121.383 (3)
N3—C21.312 (3)C7—C81.389 (3)
N3—C11.353 (3)C8—C91.388 (3)
N4—C41.286 (2)C8—H8A0.93
N4—N51.369 (2)C9—C101.364 (4)
N5—C51.334 (2)C9—H9A0.93
N5—H5A0.86C10—C111.370 (3)
N6—N71.380 (2)C11—C121.373 (3)
N6—C41.380 (2)C11—H11A0.93
N6—C51.387 (2)C12—H12A0.93
N7—C61.264 (2)O1W—H2WA0.89 (4)
N8—C101.475 (3)O1W—H1WA0.88 (4)
C1—H1A0.93
C2—N1—N2109.95 (18)N4—C4—N6110.67 (17)
C2—N1—C3129.99 (18)N4—C4—C3125.02 (18)
N2—N1—C3120.00 (17)N6—C4—C3124.25 (17)
C1—N2—N1102.11 (19)N5—C5—N6102.56 (15)
C2—N3—C1102.1 (2)N5—C5—S1127.34 (14)
C4—N4—N5104.81 (16)N6—C5—S1130.10 (14)
C5—N5—N4113.94 (15)N7—C6—C7117.83 (18)
C5—N5—H5A123.0N7—C6—H6A121.1
N4—N5—H5A123.0C7—C6—H6A121.1
N7—N6—C4117.91 (15)C12—C7—C8119.30 (19)
N7—N6—C5134.04 (16)C12—C7—C6121.03 (18)
C4—N6—C5108.00 (15)C8—C7—C6119.66 (19)
C6—N7—N6120.86 (16)C9—C8—C7120.0 (2)
O1—N8—O2124.0 (3)C9—C8—H8A120.0
O1—N8—C10118.0 (3)C7—C8—H8A120.0
O2—N8—C10118.0 (3)C10—C9—C8118.5 (2)
N2—C1—N3115.3 (2)C10—C9—H9A120.7
N2—C1—H1A122.3C8—C9—H9A120.7
N3—C1—H1A122.3C9—C10—C11122.8 (2)
N3—C2—N1110.45 (19)C9—C10—N8119.1 (2)
N3—C2—H2A124.8C11—C10—N8118.1 (2)
N1—C2—H2A124.8C10—C11—C12118.3 (2)
N1—C3—C4110.20 (16)C10—C11—H11A120.9
N1—C3—H3B109.6C12—C11—H11A120.9
C4—C3—H3B109.6C11—C12—C7121.0 (2)
N1—C3—H3C109.6C11—C12—H12A119.5
C4—C3—H3C109.6C7—C12—H12A119.5
H3B—C3—H3C108.1H2WA—O1W—H1WA109 (3)
C2—N1—N2—C10.7 (3)N7—N6—C5—N5175.77 (18)
C3—N1—N2—C1177.0 (2)C4—N6—C5—N51.52 (19)
C4—N4—N5—C50.8 (2)N7—N6—C5—S13.2 (3)
C4—N6—N7—C6175.17 (18)C4—N6—C5—S1179.46 (15)
C5—N6—N7—C61.9 (3)N6—N7—C6—C7178.06 (16)
N1—N2—C1—N30.3 (3)N7—C6—C7—C123.8 (3)
C2—N3—C1—N20.1 (3)N7—C6—C7—C8176.96 (19)
C1—N3—C2—N10.6 (2)C12—C7—C8—C91.2 (3)
N2—N1—C2—N30.8 (2)C6—C7—C8—C9179.61 (19)
C3—N1—C2—N3176.50 (19)C7—C8—C9—C100.7 (3)
C2—N1—C3—C4118.5 (2)C8—C9—C10—C110.5 (3)
N2—N1—C3—C458.7 (2)C8—C9—C10—N8178.7 (2)
N5—N4—C4—N60.3 (2)O1—N8—C10—C95.0 (4)
N5—N4—C4—C3176.97 (18)O2—N8—C10—C9175.5 (3)
N7—N6—C4—N4176.63 (16)O1—N8—C10—C11174.3 (3)
C5—N6—C4—N41.2 (2)O2—N8—C10—C115.2 (4)
N7—N6—C4—C36.1 (3)C9—C10—C11—C121.1 (3)
C5—N6—C4—C3176.09 (17)N8—C10—C11—C12178.1 (2)
N1—C3—C4—N4106.4 (2)C10—C11—C12—C70.6 (3)
N1—C3—C4—N670.5 (2)C8—C7—C12—C110.6 (3)
N4—N5—C5—N61.4 (2)C6—C7—C12—C11179.8 (2)
N4—N5—C5—S1179.50 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H2WA···N4i0.89 (4)2.06 (4)2.945 (3)172 (3)
O1W—H1WA···N3ii0.88 (4)1.88 (4)2.747 (3)172 (3)
N5—H5A···O1W0.861.832.661 (2)162
Symmetry codes: (i) x, y+3/2, z1/2; (ii) x1, y, z1.
 

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