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The crystal structure of the title compound, C
3H
3NOS
2, has been redetermined at 173 K. The geometric parameters show a significant improvement in precision from the orginal determination [Van der Helm, Lessor & Merritt (1962).
Acta Cryst.
15, 1227–1232], where the data were measured using photographic film. In the crystal structure, molecules form planar N—H
S hydrogen-bonded dimers.
Supporting information
CCDC reference: 640418
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C)= 0.002 Å
- R factor = 0.020
- wR factor = 0.058
- Data-to-parameter ratio = 15.8
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
Data collection: APEXII (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); 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: publCIF (Westrip, 2007).
Crystal data top
C3H3NOS2 | F(000) = 272 |
Mr = 133.18 | Dx = 1.687 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 5868 reflections |
a = 7.1876 (1) Å | θ = 2.7–34.8° |
b = 7.5574 (1) Å | µ = 0.88 mm−1 |
c = 9.9110 (2) Å | T = 173 K |
β = 103.031 (1)° | Plate, colorless |
V = 524.50 (2) Å3 | 0.75 × 0.38 × 0.10 mm |
Z = 4 | |
Data collection top
Bruker APEX-II diffractometer | 1202 independent reflections |
Radiation source: medium-focus sealed tube | 1143 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
φ and ω scans | θmax = 27.5°, θmin = 3.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.678, Tmax = 0.916 | k = −9→9 |
5865 measured reflections | l = −12→12 |
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)] = 0.020 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.058 | All H-atom parameters refined |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0302P)2 + 0.2928P] where P = (Fo2 + 2Fc2)/3 |
1202 reflections | (Δ/σ)max = 0.001 |
76 parameters | Δρmax = 0.39 e Å−3 |
3 restraints | Δρmin = −0.18 e Å−3 |
Special details top
Experimental. The diameter of the X-ray beam is 0.8 mm. A somewhat long platelet was used in
the measurements. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.52483 (4) | 0.03297 (4) | 0.75315 (3) | 0.01603 (11) | |
S2 | 0.82783 (4) | 0.03632 (4) | 0.59006 (3) | 0.01717 (11) | |
O1 | 0.3128 (1) | 0.4720 (1) | 0.5899 (1) | 0.01596 (19) | |
N1 | 0.5580 (1) | 0.2808 (1) | 0.5831 (1) | 0.0132 (2) | |
C1 | 0.6416 (2) | 0.1251 (2) | 0.6347 (1) | 0.0131 (2) | |
C2 | 0.3490 (2) | 0.2075 (2) | 0.7302 (1) | 0.0142 (2) | |
C3 | 0.4004 (2) | 0.3361 (2) | 0.6284 (1) | 0.0126 (2) | |
H1 | 0.602 (2) | 0.344 (2) | 0.525 (1) | 0.023 (4)* | |
H2 | 0.221 (2) | 0.159 (2) | 0.693 (2) | 0.023 (4)* | |
H3 | 0.352 (2) | 0.268 (2) | 0.818 (1) | 0.023 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0164 (2) | 0.0155 (2) | 0.0170 (2) | 0.0014 (1) | 0.0054 (1) | 0.0054 (1) |
S2 | 0.0139 (2) | 0.0191 (2) | 0.0189 (2) | 0.0044 (1) | 0.0046 (1) | 0.0007 (1) |
O1 | 0.0180 (4) | 0.0151 (4) | 0.0166 (4) | 0.0028 (3) | 0.0077 (3) | 0.0019 (3) |
N1 | 0.0149 (4) | 0.0129 (4) | 0.0135 (4) | 0.0005 (4) | 0.0067 (4) | 0.0018 (3) |
C1 | 0.0128 (5) | 0.0143 (5) | 0.0119 (5) | −0.0011 (4) | 0.0021 (4) | −0.0012 (4) |
C2 | 0.0148 (5) | 0.0140 (5) | 0.0152 (5) | 0.0000 (4) | 0.0063 (4) | 0.0017 (4) |
C3 | 0.0133 (5) | 0.0136 (5) | 0.0112 (5) | −0.0015 (4) | 0.0032 (4) | −0.0011 (4) |
Geometric parameters (Å, º) top
S1—C1 | 1.735 (1) | N1—C3 | 1.375 (1) |
S1—C2 | 1.805 (1) | C2—C3 | 1.505 (2) |
S2—C1 | 1.645 (1) | N1—H1 | 0.86 (1) |
O1—C3 | 1.220 (1) | C2—H2 | 0.98 (1) |
N1—C1 | 1.367 (1) | C2—H3 | 0.98 (1) |
| | | |
C1—S1—C2 | 93.1 (1) | N1—C3—C2 | 111.6 (1) |
C1—N1—C3 | 117.7 (1) | C1—N1—H1 | 122 (1) |
N1—C1—S2 | 124.5 (1) | C3—N1—H1 | 120 (1) |
N1—C1—S1 | 111.1 (1) | C3—C2—H2 | 110 (1) |
S2—C1—S1 | 124.4 (1) | S1—C2—H2 | 110 (1) |
C3—C2—S1 | 106.6 (1) | C3—C2—H3 | 110 (1) |
O1—C3—N1 | 124.0 (1) | S1—C2—H3 | 111 (1) |
O1—C3—C2 | 124.5 (1) | H2—C2—H3 | 110 (1) |
| | | |
C3—N1—C1—S2 | 178.6 (1) | C1—N1—C3—O1 | −179.8 (1) |
C3—N1—C1—S1 | −1.1 (1) | C1—N1—C3—C2 | −0.2 (1) |
C2—S1—C1—N1 | 1.63 (9) | S1—C2—C3—O1 | −1791 (1) |
C2—S1—C1—S2 | −178.1 (1) | S1—C2—C3—N1 | 1.4 (1) |
C1—S1—C2—C3 | −1.7 (1) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 (1) | 1.98 (1) | 2.831 (1) | 169 (2) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
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