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The structure of the title compound, C3H3NO2S, comprises flat mol­ecules that associate via a single N—H...O interaction and a C—H...O close contact to the second O atom. Furthermore, 10% of the mol­ecules have S and CH2 interchanged, generating disorder.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800020717/cf6032sup1.cif
Contains datablocks I, default

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536800020717/cf6032Isup2.hkl
Contains datablock I

CCDC reference: 155898

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma]() = 0.000 Å
  • Disorder in solvent or counterion
  • R factor = 0.031
  • wR factor = 0.083
  • Data-to-parameter ratio = 14.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_302 Alert C Anion/Solvent disorder ....................... 50.00 Perc.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

The structure of the title compound, (I), is known with the room-temperature structure being refined to R = 0.069 (Form et al., 1975). Refinement on data collected at 150 K yielded R = 0.066 but left C5 as non-positive-definite, with significant electron density close to this atom. Further refinement of the disorder revealed that 10% of the molecules have S and CH2 interchanged, with the OC—NH—CO sites being in common. The molecule was consequently split into two separate partial-occupancy fragments and refined in both configurations with bond distances (for the major fragment) allowed to vary while the displacement parameters and ring geometry were restrained to be equal in each portion.

Experimental top

The title compound, (I), was prepared by Spa Contract Synthesis.

Refinement top

All H atoms were included in the refinement at calculated positions as riding models, with C—H set to 0.88 (N—H) and 0.99 Å (CH2).

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular configuration and atom numbering scheme for (I), showing 50% probability displacement ellipsoids.
Thiazolidine-2,4-dione top
Crystal data top
C3H3NO2SDx = 1.736 Mg m3
Mr = 117.12Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 3675 reflections
a = 7.2926 (2) Åθ = 1.0–27.5°
b = 9.3642 (3) ŵ = 0.58 mm1
c = 13.1208 (5) ÅT = 150 K
V = 896.01 (5) Å3Plate, colourless
Z = 80.50 × 0.30 × 0.07 mm
F(000) = 480
Data collection top
Enraf Nonius KappaCCD area-detector
diffractometer
1018 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode919 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.9°
ϕ and ω scansh = 99
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
k = 1212
Tmin = 0.759, Tmax = 0.960l = 1617
5895 measured reflections
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0403P)2 + 0.44P]
where P = (Fo2 + 2Fc2)/3
1018 reflections(Δ/σ)max < 0.001
70 parametersΔρmax = 0.37 e Å3
6 restraintsΔρmin = 0.29 e Å3
Crystal data top
C3H3NO2SV = 896.01 (5) Å3
Mr = 117.12Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 7.2926 (2) ŵ = 0.58 mm1
b = 9.3642 (3) ÅT = 150 K
c = 13.1208 (5) Å0.50 × 0.30 × 0.07 mm
Data collection top
Enraf Nonius KappaCCD area-detector
diffractometer
1018 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
919 reflections with I > 2σ(I)
Tmin = 0.759, Tmax = 0.960Rint = 0.057
5895 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0316 restraints
wR(F2) = 0.083H-atom parameters constrained
S = 1.09Δρmax = 0.37 e Å3
1018 reflectionsΔρmin = 0.29 e Å3
70 parameters
Special details top

Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S1A0.11671 (13)0.12963 (6)0.40807 (5)0.01904 (17)0.90
C2A0.07455 (19)0.29840 (15)0.46006 (10)0.0170 (3)0.90
O21A0.13631 (15)0.33939 (12)0.54147 (8)0.0241 (3)0.90
N3A0.03733 (17)0.37873 (12)0.39882 (9)0.0162 (3)0.90
H3A0.07010.46580.41630.019*0.90
C4A0.09631 (18)0.31872 (15)0.30949 (11)0.0174 (3)0.90
O41A0.19474 (17)0.37952 (10)0.24901 (9)0.0254 (3)0.90
C5A0.0243 (6)0.1692 (2)0.2950 (3)0.0165 (4)0.90
H51A0.05070.16320.23230.020*0.90
H52A0.12690.10040.28950.020*0.90
S1B0.0163 (17)0.1465 (7)0.2928 (7)0.01904 (17)0.10
C2B0.07455 (19)0.29840 (15)0.46006 (10)0.0170 (3)0.10
O21B0.13631 (15)0.33939 (12)0.54147 (8)0.0241 (3)0.10
N3B0.03733 (17)0.37873 (12)0.39882 (9)0.0162 (3)0.10
H3B0.07010.46580.41630.019*0.10
C4B0.09631 (18)0.31872 (15)0.30949 (11)0.0174 (3)0.10
O41B0.19474 (17)0.37952 (10)0.24901 (9)0.0254 (3)0.10
C5B0.108 (5)0.1525 (18)0.4151 (18)0.0165 (4)0.10
H51B0.06240.07730.46170.020*0.10
H52B0.24110.13730.40400.020*0.10
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0213 (3)0.0135 (3)0.0223 (3)0.0033 (2)0.00173 (18)0.00065 (16)
C2A0.0158 (6)0.0150 (6)0.0204 (7)0.0008 (5)0.0019 (5)0.0005 (5)
O21A0.0283 (6)0.0211 (5)0.0229 (6)0.0063 (5)0.0061 (4)0.0029 (4)
N3A0.0161 (6)0.0120 (6)0.0206 (6)0.0013 (4)0.0010 (5)0.0015 (4)
C4A0.0142 (7)0.0154 (7)0.0226 (7)0.0031 (5)0.0002 (5)0.0000 (5)
O41A0.0272 (6)0.0193 (5)0.0298 (6)0.0001 (4)0.0112 (5)0.0001 (4)
C5A0.0141 (9)0.0088 (12)0.0266 (8)0.0017 (10)0.0012 (7)0.0026 (9)
S1B0.0213 (3)0.0135 (3)0.0223 (3)0.0033 (2)0.00173 (18)0.00065 (16)
C2B0.0158 (6)0.0150 (6)0.0204 (7)0.0008 (5)0.0019 (5)0.0005 (5)
O21B0.0283 (6)0.0211 (5)0.0229 (6)0.0063 (5)0.0061 (4)0.0029 (4)
N3B0.0161 (6)0.0120 (6)0.0206 (6)0.0013 (4)0.0010 (5)0.0015 (4)
C4B0.0142 (7)0.0154 (7)0.0226 (7)0.0031 (5)0.0002 (5)0.0000 (5)
O41B0.0272 (6)0.0193 (5)0.0298 (6)0.0001 (4)0.0112 (5)0.0001 (4)
C5B0.0141 (9)0.0088 (12)0.0266 (8)0.0017 (10)0.0012 (7)0.0026 (9)
Geometric parameters (Å, º) top
S1A—C2A1.7485 (15)C5A—S1A1.842 (3)
O21A—C2A1.2212 (18)C5A—H51A0.99
N3A—C2A1.3701 (18)C5A—H52A0.99
N3A—C4A1.3691 (18)C5B—S1B1.846 (5)
N3A—H3A0.88C5B—H51B0.99
C4A—C5A1.508 (2)C5B—H52B0.99
O41A—C4A1.2120 (18)
C4A—N3A—C2A117.63 (12)S1A—C5A—H52A110.5
C4A—N3A—H3A121.2H51A—C5A—H52A108.7
C2A—N3A—H3A121.2C2A—S1A—C5A91.96 (8)
O41A—C4A—N3A123.62 (13)O21A—C2A—N3A124.06 (13)
O41A—C4A—C5A124.08 (17)O21A—C2A—S1A124.09 (11)
N3A—C4A—C5A112.29 (17)N3A—C2A—S1A111.85 (10)
C4A—C5A—S1A106.27 (17)S1B—C5B—H51B110.4
C4A—C5A—H51A110.5S1B—C5B—H52B110.4
S1A—C5A—H51A110.5H51B—C5B—H52B108.6
C4A—C5A—H52A110.5
C2A—N3A—C4A—O41A179.62 (14)C4A—N3A—C2A—O21A179.98 (13)
C2A—N3A—C4A—C5A0.2 (3)C4A—N3A—C2A—S1A0.46 (16)
O41A—C4A—C5A—S1A179.97 (17)C5A—S1A—C2A—O21A180.0 (2)
N3A—C4A—C5A—S1A0.2 (3)C5A—S1A—C2A—N3A0.5 (2)
C4A—C5A—S1A—C2A0.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3A—H3A···O21Ai0.881.972.8465 (16)178
C5A—H52A···O41Aii0.992.503.453 (3)161
Symmetry codes: (i) x, y+1, z+1; (ii) x1/2, y1/2, z.

Experimental details

Crystal data
Chemical formulaC3H3NO2S
Mr117.12
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)150
a, b, c (Å)7.2926 (2), 9.3642 (3), 13.1208 (5)
V3)896.01 (5)
Z8
Radiation typeMo Kα
µ (mm1)0.58
Crystal size (mm)0.50 × 0.30 × 0.07
Data collection
DiffractometerEnraf Nonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1995)
Tmin, Tmax0.759, 0.960
No. of measured, independent and
observed [I > 2σ(I)] reflections
5895, 1018, 919
Rint0.057
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.083, 1.09
No. of reflections1018
No. of parameters70
No. of restraints6
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.29

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3A—H3A···O21Ai0.881.972.8465 (16)178
C5A—H52A···O41Aii0.992.503.453 (3)161
Symmetry codes: (i) x, y+1, z+1; (ii) x1/2, y1/2, z.
 

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