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The crystal structure of the title compound, C3H3NOS2, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807007374/lh2312sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807007374/lh2312Isup2.hkl
Contains datablock I

CCDC reference: 640418

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](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

Computing details top

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).

Rhodanine top
Crystal data top
C3H3NOS2F(000) = 272
Mr = 133.18Dx = 1.687 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5868 reflections
a = 7.1876 (1) Åθ = 2.7–34.8°
b = 7.5574 (1) ŵ = 0.88 mm1
c = 9.9110 (2) ÅT = 173 K
β = 103.031 (1)°Plate, colorless
V = 524.50 (2) Å30.75 × 0.38 × 0.10 mm
Z = 4
Data collection top
Bruker APEX-II
diffractometer
1202 independent reflections
Radiation source: medium-focus sealed tube1143 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
φ and ω scansθmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.678, Tmax = 0.916k = 99
5865 measured reflectionsl = 1212
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)] = 0.020Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.058All 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 parametersΔρmax = 0.39 e Å3
3 restraintsΔρmin = 0.18 e Å3
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
xyzUiso*/Ueq
S10.52483 (4)0.03297 (4)0.75315 (3)0.01603 (11)
S20.82783 (4)0.03632 (4)0.59006 (3)0.01717 (11)
O10.3128 (1)0.4720 (1)0.5899 (1)0.01596 (19)
N10.5580 (1)0.2808 (1)0.5831 (1)0.0132 (2)
C10.6416 (2)0.1251 (2)0.6347 (1)0.0131 (2)
C20.3490 (2)0.2075 (2)0.7302 (1)0.0142 (2)
C30.4004 (2)0.3361 (2)0.6284 (1)0.0126 (2)
H10.602 (2)0.344 (2)0.525 (1)0.023 (4)*
H20.221 (2)0.159 (2)0.693 (2)0.023 (4)*
H30.352 (2)0.268 (2)0.818 (1)0.023 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0164 (2)0.0155 (2)0.0170 (2)0.0014 (1)0.0054 (1)0.0054 (1)
S20.0139 (2)0.0191 (2)0.0189 (2)0.0044 (1)0.0046 (1)0.0007 (1)
O10.0180 (4)0.0151 (4)0.0166 (4)0.0028 (3)0.0077 (3)0.0019 (3)
N10.0149 (4)0.0129 (4)0.0135 (4)0.0005 (4)0.0067 (4)0.0018 (3)
C10.0128 (5)0.0143 (5)0.0119 (5)0.0011 (4)0.0021 (4)0.0012 (4)
C20.0148 (5)0.0140 (5)0.0152 (5)0.0000 (4)0.0063 (4)0.0017 (4)
C30.0133 (5)0.0136 (5)0.0112 (5)0.0015 (4)0.0032 (4)0.0011 (4)
Geometric parameters (Å, º) top
S1—C11.735 (1)N1—C31.375 (1)
S1—C21.805 (1)C2—C31.505 (2)
S2—C11.645 (1)N1—H10.86 (1)
O1—C31.220 (1)C2—H20.98 (1)
N1—C11.367 (1)C2—H30.98 (1)
C1—S1—C293.1 (1)N1—C3—C2111.6 (1)
C1—N1—C3117.7 (1)C1—N1—H1122 (1)
N1—C1—S2124.5 (1)C3—N1—H1120 (1)
N1—C1—S1111.1 (1)C3—C2—H2110 (1)
S2—C1—S1124.4 (1)S1—C2—H2110 (1)
C3—C2—S1106.6 (1)C3—C2—H3110 (1)
O1—C3—N1124.0 (1)S1—C2—H3111 (1)
O1—C3—C2124.5 (1)H2—C2—H3110 (1)
C3—N1—C1—S2178.6 (1)C1—N1—C3—O1179.8 (1)
C3—N1—C1—S11.1 (1)C1—N1—C3—C20.2 (1)
C2—S1—C1—N11.63 (9)S1—C2—C3—O11791 (1)
C2—S1—C1—S2178.1 (1)S1—C2—C3—N11.4 (1)
C1—S1—C2—C31.7 (1)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.86 (1)1.98 (1)2.831 (1)169 (2)
Symmetry code: (i) x+1, y+1, z+1.
 

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