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The geometry of the title compound, C
5H
7NOS
2·0.5H
2O, is characterized by a planar
N,
S-heterocyclic core that is distorted from a regular pentagon. Solvent water participates in non-chelated hydrogen bonds and acts as a twofold donor (O—H
S=C) and a twofold acceptor [O
H—O(—N)].
Supporting information
CCDC reference: 274373
Key indicators
- Single-crystal X-ray study
- T = 300 K
- Mean (C-C) = 0.003 Å
- R factor = 0.043
- wR factor = 0.119
- Data-to-parameter ratio = 16.7
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
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C6
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C7
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C5 H7 N O S2
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
H2 O
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 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
5 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2002); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and ORTEP-3 (Farrugia, 1997, 2005); software used to prepare material for publication: SHELXL97.
N-Hydroxy-4,5-dimethylthiazole-2(3
H)-thione hemihydrate
top
Crystal data top
C5H7NOS2·0.5H2O | Dx = 1.462 Mg m−3 |
Mr = 170.24 | Melting point: 361 K |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 25.564 (1) Å | Cell parameters from 1854 reflections |
b = 4.141 (2) Å | θ = 2.9–18.6° |
c = 15.000 (2) Å | µ = 0.62 mm−1 |
β = 103.08 (2)° | T = 300 K |
V = 1546.7 (8) Å3 | Prism, pale yellow |
Z = 8 | 0.60 × 0.48 × 0.36 mm |
F(000) = 712 | |
Data collection top
Oxford Diffraction Xcalibur with Sapphire CCD area-detector diffractometer | 1553 independent reflections |
Radiation source: fine-focus sealed tube | 1405 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
Rotation method data acquisition using ω scans | θmax = 26.4°, θmin = 4.8° |
Absorption correction: analytical CrysAlisRED (Oxford Diffraction, 2002) | h = −31→31 |
Tmin = 0.708, Tmax = 0.808 | k = −3→5 |
4701 measured reflections | l = −18→18 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.119 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.066P)2 + 1.7712P] where P = (Fo2 + 2Fc2)/3 |
1553 reflections | (Δ/σ)max = 0.012 |
93 parameters | Δρmax = 0.34 e Å−3 |
1 restraint | Δρmin = −0.27 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 | |
C2 | 0.87502 (9) | 0.3732 (5) | −0.23171 (14) | 0.0329 (5) | |
C4 | 0.88961 (9) | 0.1224 (5) | −0.08652 (14) | 0.0342 (5) | |
C5 | 0.83604 (9) | 0.0921 (6) | −0.11154 (16) | 0.0396 (5) | |
C6 | 0.92764 (11) | 0.0117 (7) | −0.00164 (16) | 0.0468 (6) | |
H6A | 0.9471 | 0.1938 | 0.0289 | 0.056* | |
H6B | 0.9524 | −0.1406 | −0.0172 | 0.056* | |
H6C | 0.9079 | −0.0894 | 0.0382 | 0.056* | |
C7 | 0.79860 (11) | −0.0493 (7) | −0.0580 (2) | 0.0558 (7) | |
H7A | 0.7792 | −0.2263 | −0.0915 | 0.067* | |
H7B | 0.7737 | 0.1131 | −0.0482 | 0.067* | |
H7C | 0.8189 | −0.1253 | 0.0000 | 0.067* | |
O1 | 0.96375 (6) | 0.3586 (4) | −0.13833 (11) | 0.0403 (4) | |
H1 | 0.9769 (11) | 0.231 (6) | −0.1728 (19) | 0.048* | |
O2 | 1.0000 | 0.9535 (6) | −0.2500 | 0.0414 (5) | |
H2 | 0.9731 (8) | 0.835 (6) | −0.2692 (19) | 0.050* | |
N3 | 0.91002 (7) | 0.2788 (4) | −0.15462 (12) | 0.0317 (4) | |
S1 | 0.81192 (2) | 0.25397 (15) | −0.22096 (4) | 0.0439 (2) | |
S2 | 0.88807 (3) | 0.56562 (15) | −0.32230 (4) | 0.0441 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C2 | 0.0339 (10) | 0.0332 (10) | 0.0327 (10) | 0.0009 (8) | 0.0096 (8) | −0.0033 (8) |
C4 | 0.0410 (12) | 0.0364 (11) | 0.0290 (10) | 0.0023 (9) | 0.0161 (9) | −0.0019 (8) |
C5 | 0.0401 (12) | 0.0437 (13) | 0.0393 (12) | −0.0008 (10) | 0.0179 (9) | −0.0027 (10) |
C6 | 0.0535 (14) | 0.0566 (14) | 0.0313 (11) | 0.0031 (12) | 0.0116 (10) | 0.0064 (11) |
C7 | 0.0524 (15) | 0.0645 (17) | 0.0606 (16) | −0.0093 (13) | 0.0341 (13) | −0.0033 (14) |
O1 | 0.0300 (8) | 0.0554 (10) | 0.0365 (8) | −0.0038 (7) | 0.0098 (6) | −0.0054 (7) |
O2 | 0.0337 (12) | 0.0449 (13) | 0.0486 (13) | 0.000 | 0.0158 (10) | 0.000 |
N3 | 0.0292 (9) | 0.0383 (10) | 0.0296 (9) | −0.0005 (7) | 0.0108 (7) | −0.0018 (7) |
S1 | 0.0308 (3) | 0.0542 (4) | 0.0462 (4) | −0.0002 (2) | 0.0076 (2) | 0.0020 (3) |
S2 | 0.0521 (4) | 0.0487 (4) | 0.0314 (3) | −0.0051 (3) | 0.0090 (3) | 0.0052 (2) |
Geometric parameters (Å, º) top
C2—N3 | 1.350 (3) | C6—H6B | 0.9600 |
C2—S2 | 1.673 (2) | C6—H6C | 0.9600 |
C2—S1 | 1.729 (2) | C7—H7A | 0.9600 |
C4—C5 | 1.341 (3) | C7—H7B | 0.9600 |
C4—N3 | 1.406 (3) | C7—H7C | 0.9600 |
C4—C6 | 1.489 (3) | O1—N3 | 1.380 (2) |
C5—C7 | 1.501 (3) | O1—H1 | 0.86 (3) |
C5—S1 | 1.751 (2) | O2—H2 | 0.841 (10) |
C6—H6A | 0.9600 | | |
| | | |
N3—C2—S2 | 128.21 (16) | H6A—C6—H6C | 109.5 |
N3—C2—S1 | 106.80 (15) | H6B—C6—H6C | 109.5 |
S2—C2—S1 | 124.99 (13) | C5—C7—H7A | 109.5 |
C5—C4—N3 | 111.29 (19) | C5—C7—H7B | 109.5 |
C5—C4—C6 | 129.7 (2) | H7A—C7—H7B | 109.5 |
N3—C4—C6 | 119.0 (2) | C5—C7—H7C | 109.5 |
C4—C5—C7 | 128.4 (2) | H7A—C7—H7C | 109.5 |
C4—C5—S1 | 110.31 (16) | H7B—C7—H7C | 109.5 |
C7—C5—S1 | 121.3 (2) | N3—O1—H1 | 104.9 (19) |
C4—C6—H6A | 109.5 | C2—N3—O1 | 121.50 (17) |
C4—C6—H6B | 109.5 | C2—N3—C4 | 118.22 (18) |
H6A—C6—H6B | 109.5 | O1—N3—C4 | 120.00 (17) |
C4—C6—H6C | 109.5 | C2—S1—C5 | 93.36 (11) |
| | | |
N3—C4—C5—C7 | −177.8 (2) | C5—C4—N3—C2 | 0.2 (3) |
C6—C4—C5—C7 | 3.5 (4) | C6—C4—N3—C2 | 179.0 (2) |
N3—C4—C5—S1 | 1.0 (2) | C5—C4—N3—O1 | 174.21 (18) |
C6—C4—C5—S1 | −177.8 (2) | C6—C4—N3—O1 | −6.9 (3) |
S2—C2—N3—O1 | 5.3 (3) | N3—C2—S1—C5 | 1.41 (16) |
S1—C2—N3—O1 | −175.14 (15) | S2—C2—S1—C5 | −179.03 (15) |
S2—C2—N3—C4 | 179.29 (16) | C4—C5—S1—C2 | −1.40 (18) |
S1—C2—N3—C4 | −1.2 (2) | C7—C5—S1—C2 | 177.5 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.86 (3) | 1.82 (3) | 2.680 (2) | 176 (3) |
O2—H2···S2 | 0.84 (1) | 2.41 (1) | 3.2463 (15) | 171 (3) |
Symmetry code: (i) x, y−1, z. |
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