In the title compound, C
12H
10N
8O
2S·H
2O, 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
CCDC reference: 636205
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.043
- wR factor = 0.125
- Data-to-parameter ratio = 15.7
checkCIF/PLATON results
No syntax errors found
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
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.
Crystal data top
C12H10N8O2S·H2O | F(000) = 720 |
Mr = 348.37 | Dx = 1.496 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 14545 reflections |
a = 8.1883 (16) Å | θ = 1.6–27.5° |
b = 24.938 (5) Å | µ = 0.24 mm−1 |
c = 7.5896 (15) Å | T = 293 K |
β = 93.56 (3)° | Plate, colourless |
V = 1546.8 (5) Å3 | 0.68 × 0.68 × 0.07 mm |
Z = 4 | |
Data collection top
Rigaku R-AXIS RAPID IP area-detector diffractometer | 3525 independent reflections |
Radiation source: Rotating Anode | 2454 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
ω scans | θmax = 27.5°, θmin = 1.6° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −10→10 |
Tmin = 0.853, Tmax = 0.984 | k = −32→32 |
14545 measured reflections | l = −9→9 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.125 | H 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 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
S1 | 0.50498 (8) | 0.57348 (2) | 0.48086 (7) | 0.05184 (18) | |
O1 | 1.0814 (4) | 0.35604 (11) | 1.2682 (4) | 0.1302 (11) | |
O2 | 1.0145 (3) | 0.40299 (12) | 1.4878 (4) | 0.1152 (9) | |
N1 | 0.6462 (2) | 0.69082 (6) | 1.1192 (2) | 0.0430 (4) | |
N2 | 0.6988 (3) | 0.73357 (8) | 1.0295 (3) | 0.0699 (6) | |
N3 | 0.9021 (3) | 0.69839 (8) | 1.2036 (2) | 0.0559 (5) | |
N4 | 0.3596 (2) | 0.68576 (7) | 0.7878 (2) | 0.0436 (4) | |
N5 | 0.3697 (2) | 0.65906 (6) | 0.6313 (2) | 0.0422 (4) | |
H5A | 0.3201 | 0.6695 | 0.5342 | 0.051* | |
N6 | 0.51264 (18) | 0.61385 (6) | 0.82115 (19) | 0.0356 (3) | |
N7 | 0.60291 (19) | 0.57820 (6) | 0.9267 (2) | 0.0392 (4) | |
N8 | 1.0113 (3) | 0.39316 (11) | 1.3304 (4) | 0.0803 (8) | |
C1 | 0.8518 (4) | 0.73615 (11) | 1.0843 (3) | 0.0706 (8) | |
H1A | 0.9220 | 0.7622 | 1.0443 | 0.085* | |
C2 | 0.7675 (3) | 0.67101 (8) | 1.2218 (3) | 0.0474 (5) | |
H2A | 0.7587 | 0.6417 | 1.2966 | 0.057* | |
C3 | 0.4801 (2) | 0.67234 (9) | 1.0890 (3) | 0.0452 (5) | |
H3B | 0.4052 | 0.7003 | 1.1211 | 0.054* | |
H3C | 0.4626 | 0.6413 | 1.1624 | 0.054* | |
C4 | 0.4470 (2) | 0.65796 (8) | 0.9009 (2) | 0.0376 (4) | |
C5 | 0.4635 (2) | 0.61532 (7) | 0.6431 (2) | 0.0359 (4) | |
C6 | 0.6567 (2) | 0.53524 (8) | 0.8636 (3) | 0.0413 (4) | |
H6A | 0.6396 | 0.5272 | 0.7442 | 0.050* | |
C7 | 0.7474 (2) | 0.49836 (8) | 0.9851 (3) | 0.0399 (4) | |
C8 | 0.8153 (3) | 0.45192 (8) | 0.9197 (3) | 0.0502 (5) | |
H8A | 0.8027 | 0.4442 | 0.7998 | 0.060* | |
C9 | 0.9019 (3) | 0.41706 (9) | 1.0333 (4) | 0.0571 (6) | |
H9A | 0.9488 | 0.3861 | 0.9908 | 0.069* | |
C10 | 0.9167 (3) | 0.42927 (9) | 1.2087 (3) | 0.0533 (6) | |
C11 | 0.8487 (3) | 0.47425 (10) | 1.2777 (3) | 0.0560 (6) | |
H11A | 0.8593 | 0.4812 | 1.3983 | 0.067* | |
C12 | 0.7646 (3) | 0.50880 (9) | 1.1642 (3) | 0.0496 (5) | |
H12A | 0.7185 | 0.5397 | 1.2085 | 0.060* | |
O1W | 0.2087 (2) | 0.71050 (7) | 0.3670 (2) | 0.0602 (5) | |
H2WA | 0.245 (4) | 0.7429 (15) | 0.339 (5) | 0.105 (12)* | |
H1WA | 0.107 (5) | 0.7072 (13) | 0.325 (4) | 0.099 (11)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0768 (4) | 0.0433 (3) | 0.0351 (3) | 0.0035 (3) | 0.0006 (2) | −0.0033 (2) |
O1 | 0.144 (2) | 0.0882 (17) | 0.156 (3) | 0.0619 (17) | −0.0104 (19) | 0.0415 (17) |
O2 | 0.1151 (19) | 0.128 (2) | 0.0976 (18) | 0.0230 (16) | −0.0294 (15) | 0.0543 (16) |
N1 | 0.0582 (10) | 0.0370 (8) | 0.0323 (8) | 0.0003 (8) | −0.0085 (7) | −0.0004 (7) |
N2 | 0.0873 (16) | 0.0593 (13) | 0.0598 (13) | −0.0186 (11) | −0.0218 (11) | 0.0202 (10) |
N3 | 0.0600 (11) | 0.0580 (11) | 0.0477 (10) | −0.0092 (10) | −0.0121 (9) | 0.0000 (9) |
N4 | 0.0474 (10) | 0.0412 (9) | 0.0412 (9) | 0.0057 (7) | −0.0058 (7) | −0.0013 (7) |
N5 | 0.0509 (9) | 0.0388 (8) | 0.0354 (8) | 0.0034 (8) | −0.0085 (7) | 0.0001 (7) |
N6 | 0.0389 (8) | 0.0348 (8) | 0.0328 (8) | 0.0025 (7) | −0.0019 (6) | 0.0011 (6) |
N7 | 0.0412 (9) | 0.0388 (9) | 0.0372 (8) | 0.0031 (7) | −0.0020 (7) | 0.0071 (7) |
N8 | 0.0632 (14) | 0.0731 (16) | 0.102 (2) | 0.0003 (12) | −0.0112 (14) | 0.0459 (15) |
C1 | 0.0870 (19) | 0.0697 (17) | 0.0526 (14) | −0.0288 (15) | −0.0163 (13) | 0.0144 (13) |
C2 | 0.0583 (13) | 0.0424 (11) | 0.0400 (10) | −0.0014 (10) | −0.0094 (9) | 0.0029 (9) |
C3 | 0.0483 (11) | 0.0494 (12) | 0.0375 (10) | 0.0071 (9) | 0.0006 (9) | −0.0045 (9) |
C4 | 0.0371 (9) | 0.0367 (10) | 0.0383 (10) | 0.0026 (8) | −0.0017 (8) | −0.0011 (8) |
C5 | 0.0394 (10) | 0.0348 (9) | 0.0329 (9) | −0.0056 (8) | −0.0015 (7) | 0.0040 (8) |
C6 | 0.0443 (11) | 0.0419 (10) | 0.0375 (10) | 0.0026 (9) | 0.0010 (8) | 0.0028 (8) |
C7 | 0.0363 (9) | 0.0384 (10) | 0.0451 (11) | 0.0003 (8) | 0.0020 (8) | 0.0073 (8) |
C8 | 0.0542 (12) | 0.0429 (11) | 0.0536 (12) | 0.0070 (10) | 0.0042 (10) | 0.0008 (10) |
C9 | 0.0510 (13) | 0.0416 (12) | 0.0791 (17) | 0.0096 (10) | 0.0061 (12) | 0.0094 (11) |
C10 | 0.0394 (11) | 0.0495 (12) | 0.0703 (15) | −0.0021 (10) | −0.0018 (10) | 0.0268 (12) |
C11 | 0.0554 (13) | 0.0653 (15) | 0.0468 (12) | −0.0015 (11) | −0.0011 (10) | 0.0164 (11) |
C12 | 0.0544 (12) | 0.0501 (12) | 0.0443 (11) | 0.0074 (10) | 0.0023 (10) | 0.0063 (10) |
O1W | 0.0513 (10) | 0.0583 (10) | 0.0688 (11) | −0.0041 (8) | −0.0144 (8) | 0.0223 (9) |
Geometric parameters (Å, º) top
S1—C5 | 1.6647 (19) | C2—H2A | 0.93 |
O1—N8 | 1.201 (4) | C3—C4 | 1.481 (3) |
O2—N8 | 1.218 (4) | C3—H3B | 0.97 |
N1—C2 | 1.320 (3) | C3—H3C | 0.97 |
N1—N2 | 1.350 (2) | C6—C7 | 1.471 (3) |
N1—C3 | 1.440 (3) | C6—H6A | 0.93 |
N2—C1 | 1.297 (3) | C7—C12 | 1.383 (3) |
N3—C2 | 1.312 (3) | C7—C8 | 1.389 (3) |
N3—C1 | 1.353 (3) | C8—C9 | 1.388 (3) |
N4—C4 | 1.286 (2) | C8—H8A | 0.93 |
N4—N5 | 1.369 (2) | C9—C10 | 1.364 (4) |
N5—C5 | 1.334 (2) | C9—H9A | 0.93 |
N5—H5A | 0.86 | C10—C11 | 1.370 (3) |
N6—N7 | 1.380 (2) | C11—C12 | 1.373 (3) |
N6—C4 | 1.380 (2) | C11—H11A | 0.93 |
N6—C5 | 1.387 (2) | C12—H12A | 0.93 |
N7—C6 | 1.264 (2) | O1W—H2WA | 0.89 (4) |
N8—C10 | 1.475 (3) | O1W—H1WA | 0.88 (4) |
C1—H1A | 0.93 | | |
| | | |
C2—N1—N2 | 109.95 (18) | N4—C4—N6 | 110.67 (17) |
C2—N1—C3 | 129.99 (18) | N4—C4—C3 | 125.02 (18) |
N2—N1—C3 | 120.00 (17) | N6—C4—C3 | 124.25 (17) |
C1—N2—N1 | 102.11 (19) | N5—C5—N6 | 102.56 (15) |
C2—N3—C1 | 102.1 (2) | N5—C5—S1 | 127.34 (14) |
C4—N4—N5 | 104.81 (16) | N6—C5—S1 | 130.10 (14) |
C5—N5—N4 | 113.94 (15) | N7—C6—C7 | 117.83 (18) |
C5—N5—H5A | 123.0 | N7—C6—H6A | 121.1 |
N4—N5—H5A | 123.0 | C7—C6—H6A | 121.1 |
N7—N6—C4 | 117.91 (15) | C12—C7—C8 | 119.30 (19) |
N7—N6—C5 | 134.04 (16) | C12—C7—C6 | 121.03 (18) |
C4—N6—C5 | 108.00 (15) | C8—C7—C6 | 119.66 (19) |
C6—N7—N6 | 120.86 (16) | C9—C8—C7 | 120.0 (2) |
O1—N8—O2 | 124.0 (3) | C9—C8—H8A | 120.0 |
O1—N8—C10 | 118.0 (3) | C7—C8—H8A | 120.0 |
O2—N8—C10 | 118.0 (3) | C10—C9—C8 | 118.5 (2) |
N2—C1—N3 | 115.3 (2) | C10—C9—H9A | 120.7 |
N2—C1—H1A | 122.3 | C8—C9—H9A | 120.7 |
N3—C1—H1A | 122.3 | C9—C10—C11 | 122.8 (2) |
N3—C2—N1 | 110.45 (19) | C9—C10—N8 | 119.1 (2) |
N3—C2—H2A | 124.8 | C11—C10—N8 | 118.1 (2) |
N1—C2—H2A | 124.8 | C10—C11—C12 | 118.3 (2) |
N1—C3—C4 | 110.20 (16) | C10—C11—H11A | 120.9 |
N1—C3—H3B | 109.6 | C12—C11—H11A | 120.9 |
C4—C3—H3B | 109.6 | C11—C12—C7 | 121.0 (2) |
N1—C3—H3C | 109.6 | C11—C12—H12A | 119.5 |
C4—C3—H3C | 109.6 | C7—C12—H12A | 119.5 |
H3B—C3—H3C | 108.1 | H2WA—O1W—H1WA | 109 (3) |
| | | |
C2—N1—N2—C1 | 0.7 (3) | N7—N6—C5—N5 | 175.77 (18) |
C3—N1—N2—C1 | −177.0 (2) | C4—N6—C5—N5 | −1.52 (19) |
C4—N4—N5—C5 | −0.8 (2) | N7—N6—C5—S1 | −3.2 (3) |
C4—N6—N7—C6 | 175.17 (18) | C4—N6—C5—S1 | 179.46 (15) |
C5—N6—N7—C6 | −1.9 (3) | N6—N7—C6—C7 | −178.06 (16) |
N1—N2—C1—N3 | −0.3 (3) | N7—C6—C7—C12 | 3.8 (3) |
C2—N3—C1—N2 | −0.1 (3) | N7—C6—C7—C8 | −176.96 (19) |
C1—N3—C2—N1 | 0.6 (2) | C12—C7—C8—C9 | −1.2 (3) |
N2—N1—C2—N3 | −0.8 (2) | C6—C7—C8—C9 | 179.61 (19) |
C3—N1—C2—N3 | 176.50 (19) | C7—C8—C9—C10 | 0.7 (3) |
C2—N1—C3—C4 | −118.5 (2) | C8—C9—C10—C11 | 0.5 (3) |
N2—N1—C3—C4 | 58.7 (2) | C8—C9—C10—N8 | −178.7 (2) |
N5—N4—C4—N6 | −0.3 (2) | O1—N8—C10—C9 | 5.0 (4) |
N5—N4—C4—C3 | 176.97 (18) | O2—N8—C10—C9 | −175.5 (3) |
N7—N6—C4—N4 | −176.63 (16) | O1—N8—C10—C11 | −174.3 (3) |
C5—N6—C4—N4 | 1.2 (2) | O2—N8—C10—C11 | 5.2 (4) |
N7—N6—C4—C3 | 6.1 (3) | C9—C10—C11—C12 | −1.1 (3) |
C5—N6—C4—C3 | −176.09 (17) | N8—C10—C11—C12 | 178.1 (2) |
N1—C3—C4—N4 | −106.4 (2) | C10—C11—C12—C7 | 0.6 (3) |
N1—C3—C4—N6 | 70.5 (2) | C8—C7—C12—C11 | 0.6 (3) |
N4—N5—C5—N6 | 1.4 (2) | C6—C7—C12—C11 | 179.8 (2) |
N4—N5—C5—S1 | −179.50 (14) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H2WA···N4i | 0.89 (4) | 2.06 (4) | 2.945 (3) | 172 (3) |
O1W—H1WA···N3ii | 0.88 (4) | 1.88 (4) | 2.747 (3) | 172 (3) |
N5—H5A···O1W | 0.86 | 1.83 | 2.661 (2) | 162 |
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x−1, y, z−1. |