The molecule of the Schiff base in the crystal structure of the title compound, C8H9N3O2S·0.5H2O, interacts with symmetry-equivalent molecules and with the water molecule, which lies on a twofold rotation axis, to give a three-dimensional hydrogen-bonded network structure.
Supporting information
CCDC reference: 629438
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.057
- wR factor = 0.129
- Data-to-parameter ratio = 11.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.04
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
PLAT731_ALERT_1_C Bond Calc 0.84(3), Rep 0.840(10) ...... 3.00 su-Ra
O1 -H1O 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra
O2 -H2O 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra
O1W -H1W 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra
N1 -H1N1 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra
N1 -H1N2 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.84(3), Rep 0.840(10) ...... 3.00 su-Ra
O1 -H1O 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra
O2 -H2O 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra
N1 -H1# 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra
N1 -H2# 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.850(10) ...... 3.00 su-Ra
O1W -H1W 1.555 1.555
PLAT736_ALERT_1_C H...A Calc 1.94(3), Rep 1.950(10) ...... 3.00 su-Ra
H2O -O1W 1.555 1.555
PLAT736_ALERT_1_C H...A Calc 2.56(3), Rep 2.560(10) ...... 3.00 su-Ra
H1# -S1 1.555 5.565
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
H2 O
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
18 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
16 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
0 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.
2,3-Dihydroxybenzaldehyde thiosemicarbazone hemihydrate
top
Crystal data top
C8H9N3O2S·0.5H2O | F(000) = 920 |
Mr = 220.25 | Dx = 1.479 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 870 reflections |
a = 21.546 (2) Å | θ = 3.0–26.5° |
b = 11.658 (1) Å | µ = 0.31 mm−1 |
c = 8.190 (1) Å | T = 293 K |
β = 105.923 (1)° | Needle, yellow |
V = 1978.3 (3) Å3 | 0.50 × 0.20 × 0.10 mm |
Z = 8 | |
Data collection top
Bruker APEX CCD area-detector diffractometer | 1510 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.028 |
Graphite monochromator | θmax = 25.0°, θmin = 2.0° |
ω and φ scans | h = −20→25 |
5025 measured reflections | k = −11→13 |
1740 independent 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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.129 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.19 | w = 1/[σ2(Fo2) + (0.0539P)2 + 2.2284P] where P = (Fo2 + 2Fc2)/3 |
1740 reflections | (Δ/σ)max = 0.001 |
150 parameters | Δρmax = 0.24 e Å−3 |
7 restraints | Δρmin = −0.20 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.05404 (4) | 0.66980 (7) | 0.05330 (10) | 0.0400 (3) | |
O1 | 0.33493 (11) | 0.65271 (18) | 0.7870 (3) | 0.0437 (6) | |
H1O | 0.3647 (12) | 0.673 (3) | 0.872 (3) | 0.052* | |
O2 | 0.42287 (11) | 0.52486 (19) | 1.0011 (3) | 0.0447 (6) | |
H2O | 0.4441 (15) | 0.477 (2) | 1.074 (3) | 0.054* | |
O1W | 0.5000 | 0.3835 (3) | 1.2500 | 0.0460 (8) | |
H1W | 0.5190 (15) | 0.3410 (15) | 1.194 (4) | 0.055* | |
N1 | 0.07603 (14) | 0.4660 (2) | 0.2009 (4) | 0.0468 (8) | |
H1N1 | 0.0429 (11) | 0.442 (3) | 0.127 (3) | 0.056* | |
H1N2 | 0.0936 (16) | 0.425 (3) | 0.287 (3) | 0.056* | |
N2 | 0.14665 (12) | 0.6054 (2) | 0.3211 (3) | 0.0365 (6) | |
H2N | 0.1620 (16) | 0.6719 (14) | 0.317 (4) | 0.044* | |
N3 | 0.18247 (12) | 0.5253 (2) | 0.4308 (3) | 0.0334 (6) | |
C1 | 0.09380 (14) | 0.5736 (3) | 0.1997 (4) | 0.0316 (7) | |
C2 | 0.23371 (14) | 0.5627 (3) | 0.5353 (3) | 0.0312 (7) | |
H2 | 0.2428 | 0.6407 | 0.5357 | 0.037* | |
C3 | 0.27822 (14) | 0.4890 (2) | 0.6533 (4) | 0.0291 (7) | |
C4 | 0.32941 (14) | 0.5363 (2) | 0.7768 (4) | 0.0290 (7) | |
C5 | 0.37463 (14) | 0.4673 (3) | 0.8885 (4) | 0.0338 (7) | |
C6 | 0.36873 (15) | 0.3497 (3) | 0.8757 (4) | 0.0391 (8) | |
H6 | 0.3990 | 0.3029 | 0.9484 | 0.047* | |
C7 | 0.31737 (17) | 0.3014 (3) | 0.7537 (4) | 0.0436 (8) | |
H7 | 0.3133 | 0.2220 | 0.7456 | 0.052* | |
C8 | 0.27283 (15) | 0.3693 (3) | 0.6458 (4) | 0.0370 (7) | |
H8 | 0.2384 | 0.3355 | 0.5661 | 0.044* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0375 (5) | 0.0327 (5) | 0.0385 (5) | −0.0004 (3) | −0.0088 (3) | −0.0010 (4) |
O1 | 0.0407 (13) | 0.0297 (12) | 0.0457 (14) | −0.0065 (9) | −0.0135 (10) | 0.0013 (10) |
O2 | 0.0384 (13) | 0.0425 (14) | 0.0393 (13) | −0.0032 (10) | −0.0126 (10) | 0.0057 (10) |
O1W | 0.043 (2) | 0.051 (2) | 0.041 (2) | 0.000 | 0.0071 (15) | 0.000 |
N1 | 0.0411 (16) | 0.0375 (17) | 0.0461 (18) | −0.0126 (13) | −0.0148 (13) | 0.0064 (13) |
N2 | 0.0321 (14) | 0.0292 (14) | 0.0380 (14) | −0.0060 (11) | −0.0078 (11) | 0.0025 (12) |
N3 | 0.0314 (14) | 0.0310 (14) | 0.0311 (14) | −0.0033 (11) | −0.0025 (11) | 0.0013 (11) |
C1 | 0.0282 (15) | 0.0343 (17) | 0.0288 (15) | −0.0033 (13) | 0.0022 (12) | −0.0052 (13) |
C2 | 0.0318 (16) | 0.0276 (16) | 0.0310 (16) | −0.0051 (13) | 0.0030 (13) | −0.0018 (13) |
C3 | 0.0290 (15) | 0.0307 (16) | 0.0262 (15) | −0.0031 (12) | 0.0053 (12) | 0.0010 (12) |
C4 | 0.0307 (16) | 0.0278 (16) | 0.0279 (16) | −0.0026 (12) | 0.0069 (12) | −0.0003 (12) |
C5 | 0.0303 (16) | 0.0385 (18) | 0.0294 (16) | −0.0013 (13) | 0.0026 (13) | 0.0022 (14) |
C6 | 0.0391 (18) | 0.0360 (19) | 0.0367 (18) | 0.0090 (14) | 0.0014 (14) | 0.0085 (14) |
C7 | 0.053 (2) | 0.0288 (17) | 0.045 (2) | 0.0000 (15) | 0.0053 (16) | 0.0011 (15) |
C8 | 0.0386 (17) | 0.0336 (17) | 0.0335 (17) | −0.0055 (14) | 0.0008 (14) | −0.0049 (14) |
Geometric parameters (Å, º) top
S1—C1 | 1.693 (3) | N3—C2 | 1.274 (4) |
O1—C4 | 1.363 (4) | C2—C3 | 1.443 (4) |
O1—H1O | 0.84 (1) | C2—H2 | 0.930 |
O2—C5 | 1.362 (3) | C3—C4 | 1.390 (4) |
O2—H2O | 0.85 (1) | C3—C8 | 1.400 (4) |
O1W—H1W | 0.85 (1) | C4—C5 | 1.394 (4) |
N1—C1 | 1.313 (4) | C5—C6 | 1.378 (4) |
N1—H1N1 | 0.85 (1) | C6—C7 | 1.390 (4) |
N1—H1N2 | 0.85 (1) | C6—H6 | 0.930 |
N2—C1 | 1.342 (4) | C7—C8 | 1.365 (4) |
N2—N3 | 1.376 (3) | C7—H7 | 0.930 |
N2—H2N | 0.85 (1) | C8—H8 | 0.930 |
| | | |
C4—O1—H1O | 111 (2) | C8—C3—C2 | 122.2 (3) |
C5—O2—H2O | 109 (2) | O1—C4—C3 | 118.6 (3) |
C1—N1—H1N1 | 120 (2) | O1—C4—C5 | 120.0 (3) |
C1—N1—H1N2 | 119 (2) | C3—C4—C5 | 121.4 (3) |
H1N1—N1—H1N2 | 120 (3) | O2—C5—C6 | 125.4 (3) |
C1—N2—N3 | 120.4 (2) | O2—C5—C4 | 115.3 (3) |
C1—N2—H2N | 119 (2) | C6—C5—C4 | 119.4 (3) |
N3—N2—H2N | 119 (2) | C5—C6—C7 | 119.8 (3) |
C2—N3—N2 | 115.7 (2) | C5—C6—H6 | 120.1 |
N1—C1—N2 | 116.6 (3) | C7—C6—H6 | 120.1 |
N1—C1—S1 | 123.1 (2) | C8—C7—C6 | 120.7 (3) |
N2—C1—S1 | 120.2 (2) | C8—C7—H7 | 119.7 |
N3—C2—C3 | 122.7 (3) | C6—C7—H7 | 119.7 |
N3—C2—H2 | 118.6 | C7—C8—C3 | 121.0 (3) |
C3—C2—H2 | 118.6 | C7—C8—H8 | 119.5 |
C4—C3—C8 | 117.8 (3) | C3—C8—H8 | 119.5 |
C4—C3—C2 | 120.0 (3) | | |
| | | |
C1—N2—N3—C2 | 176.2 (3) | O1—C4—C5—O2 | −0.9 (4) |
N3—N2—C1—N1 | 5.2 (4) | C3—C4—C5—O2 | 178.9 (3) |
N3—N2—C1—S1 | −174.0 (2) | O1—C4—C5—C6 | −179.4 (3) |
N2—N3—C2—C3 | −177.0 (3) | C3—C4—C5—C6 | 0.4 (5) |
N3—C2—C3—C4 | −172.8 (3) | O2—C5—C6—C7 | −179.4 (3) |
N3—C2—C3—C8 | 8.8 (5) | C4—C5—C6—C7 | −1.0 (5) |
C8—C3—C4—O1 | −179.3 (3) | C5—C6—C7—C8 | 0.3 (5) |
C2—C3—C4—O1 | 2.3 (4) | C6—C7—C8—C3 | 1.0 (5) |
C8—C3—C4—C5 | 0.9 (4) | C4—C3—C8—C7 | −1.6 (5) |
C2—C3—C4—C5 | −177.6 (3) | C2—C3—C8—C7 | 176.8 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···S1i | 0.84 (1) | 2.50 (2) | 3.162 (2) | 137 (3) |
O2—H2O···O1W | 0.85 (1) | 1.95 (1) | 2.788 (3) | 173 (4) |
N1—H1N1···S1ii | 0.85 (1) | 2.56 (1) | 3.390 (3) | 167 (3) |
N1—H1N2···N3 | 0.85 (1) | 2.28 (4) | 2.629 (3) | 105 (3) |
N2—H2N···O1i | 0.85 (1) | 2.22 (2) | 3.014 (3) | 155 (3) |
O1W—H1W···S1iii | 0.85 (1) | 2.52 (1) | 3.345 (3) | 163 (2) |
Symmetry codes: (i) −x+1/2, −y+3/2, −z+1; (ii) −x, −y+1, −z; (iii) x+1/2, y−1/2, z+1. |