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organic compounds
The structure of the title compound, C3H3NO2S, comprises flat molecules that associate via a single N—H
O interaction and a C—HO close contact to the second O atom. Furthermore, 10% of the molecules have S and CH2 interchanged, generating disorder.
O interaction and a C—HO close contact to the second O atom. Furthermore, 10% of the molecules have S and CH2 interchanged, generating disorder.Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800020717/cf6032sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S1600536800020717/cf6032Isup2.hkl |
CCDC reference: 155898
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean
![[sigma]](https://journals.iucr.org/logos/entities/sigma_rmgif.gif)
( ) = 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 symmetryAlert 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
S3. 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]](https://journals.iucr.org/e/issues/2001/01/00/cf6032/cf6032fig1thm.gif)
| Fig. 1. The molecular configuration and atom numbering scheme for (I), showing 50% probability displacement ellipsoids. |
Thiazolidine-2,4-dione top
Crystal data top
| C3H3NO2S | Dx = 1.736 Mg m−3 |
| Mr = 117.12 | Mo Kα radiation, λ = 0.71073 Å |
| Orthorhombic, Pbca | Cell parameters from 3675 reflections |
| a = 7.2926 (2) Å | θ = 1.0–27.5° |
| b = 9.3642 (3) Å | µ = 0.58 mm−1 |
| c = 13.1208 (5) Å | T = 150 K |
| V = 896.01 (5) Å3 | Plate, colourless |
| Z = 8 | 0.50 × 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 anode | 919 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.057 |
| Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.9° |
| ϕ and ω scans | h = −9→9 |
| Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −12→12 |
| Tmin = 0.759, Tmax = 0.960 | l = −16→17 |
| 5895 measured reflections |
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)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.083 | H-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 parameters | Δρmax = 0.37 e Å−3 |
| 6 restraints | Δρmin = −0.29 e Å−3 |
Crystal data top
| C3H3NO2S | V = 896.01 (5) Å3 |
| Mr = 117.12 | Z = 8 |
| Orthorhombic, Pbca | Mo Kα radiation |
| a = 7.2926 (2) Å | µ = 0.58 mm−1 |
| b = 9.3642 (3) Å | T = 150 K |
| c = 13.1208 (5) Å | 0.50 × 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 = 0.960 | Rint = 0.057 |
| 5895 measured reflections |
Refinement top
| R[F2 > 2σ(F2)] = 0.031 | 6 restraints |
| wR(F2) = 0.083 | H-atom parameters constrained |
| S = 1.09 | Δρmax = 0.37 e Å−3 |
| 1018 reflections | Δρmin = −0.29 e Å−3 |
| 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
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| S1A | 0.11671 (13) | 0.12963 (6) | 0.40807 (5) | 0.01904 (17) | 0.90 |
| C2A | 0.07455 (19) | 0.29840 (15) | 0.46006 (10) | 0.0170 (3) | 0.90 |
| O21A | 0.13631 (15) | 0.33939 (12) | 0.54147 (8) | 0.0241 (3) | 0.90 |
| N3A | −0.03733 (17) | 0.37873 (12) | 0.39882 (9) | 0.0162 (3) | 0.90 |
| H3A | −0.0701 | 0.4658 | 0.4163 | 0.019* | 0.90 |
| C4A | −0.09631 (18) | 0.31872 (15) | 0.30949 (11) | 0.0174 (3) | 0.90 |
| O41A | −0.19474 (17) | 0.37952 (10) | 0.24901 (9) | 0.0254 (3) | 0.90 |
| C5A | −0.0243 (6) | 0.1692 (2) | 0.2950 (3) | 0.0165 (4) | 0.90 |
| H51A | 0.0507 | 0.1632 | 0.2323 | 0.020* | 0.90 |
| H52A | −0.1269 | 0.1004 | 0.2895 | 0.020* | 0.90 |
| S1B | −0.0163 (17) | 0.1465 (7) | 0.2928 (7) | 0.01904 (17) | 0.10 |
| C2B | 0.07455 (19) | 0.29840 (15) | 0.46006 (10) | 0.0170 (3) | 0.10 |
| O21B | 0.13631 (15) | 0.33939 (12) | 0.54147 (8) | 0.0241 (3) | 0.10 |
| N3B | −0.03733 (17) | 0.37873 (12) | 0.39882 (9) | 0.0162 (3) | 0.10 |
| H3B | −0.0701 | 0.4658 | 0.4163 | 0.019* | 0.10 |
| C4B | −0.09631 (18) | 0.31872 (15) | 0.30949 (11) | 0.0174 (3) | 0.10 |
| O41B | −0.19474 (17) | 0.37952 (10) | 0.24901 (9) | 0.0254 (3) | 0.10 |
| C5B | 0.108 (5) | 0.1525 (18) | 0.4151 (18) | 0.0165 (4) | 0.10 |
| H51B | 0.0624 | 0.0773 | 0.4617 | 0.020* | 0.10 |
| H52B | 0.2411 | 0.1373 | 0.4040 | 0.020* | 0.10 |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1A | 0.0213 (3) | 0.0135 (3) | 0.0223 (3) | 0.0033 (2) | −0.00173 (18) | −0.00065 (16) |
| C2A | 0.0158 (6) | 0.0150 (6) | 0.0204 (7) | 0.0008 (5) | 0.0019 (5) | 0.0005 (5) |
| O21A | 0.0283 (6) | 0.0211 (5) | 0.0229 (6) | 0.0063 (5) | −0.0061 (4) | −0.0029 (4) |
| N3A | 0.0161 (6) | 0.0120 (6) | 0.0206 (6) | 0.0013 (4) | −0.0010 (5) | −0.0015 (4) |
| C4A | 0.0142 (7) | 0.0154 (7) | 0.0226 (7) | −0.0031 (5) | −0.0002 (5) | 0.0000 (5) |
| O41A | 0.0272 (6) | 0.0193 (5) | 0.0298 (6) | 0.0001 (4) | −0.0112 (5) | 0.0001 (4) |
| C5A | 0.0141 (9) | 0.0088 (12) | 0.0266 (8) | 0.0017 (10) | −0.0012 (7) | 0.0026 (9) |
| S1B | 0.0213 (3) | 0.0135 (3) | 0.0223 (3) | 0.0033 (2) | −0.00173 (18) | −0.00065 (16) |
| C2B | 0.0158 (6) | 0.0150 (6) | 0.0204 (7) | 0.0008 (5) | 0.0019 (5) | 0.0005 (5) |
| O21B | 0.0283 (6) | 0.0211 (5) | 0.0229 (6) | 0.0063 (5) | −0.0061 (4) | −0.0029 (4) |
| N3B | 0.0161 (6) | 0.0120 (6) | 0.0206 (6) | 0.0013 (4) | −0.0010 (5) | −0.0015 (4) |
| C4B | 0.0142 (7) | 0.0154 (7) | 0.0226 (7) | −0.0031 (5) | −0.0002 (5) | 0.0000 (5) |
| O41B | 0.0272 (6) | 0.0193 (5) | 0.0298 (6) | 0.0001 (4) | −0.0112 (5) | 0.0001 (4) |
| C5B | 0.0141 (9) | 0.0088 (12) | 0.0266 (8) | 0.0017 (10) | −0.0012 (7) | 0.0026 (9) |
Geometric parameters (Å, º) top
| S1A—C2A | 1.7485 (15) | C5A—S1A | 1.842 (3) |
| O21A—C2A | 1.2212 (18) | C5A—H51A | 0.99 |
| N3A—C2A | 1.3701 (18) | C5A—H52A | 0.99 |
| N3A—C4A | 1.3691 (18) | C5B—S1B | 1.846 (5) |
| N3A—H3A | 0.88 | C5B—H51B | 0.99 |
| C4A—C5A | 1.508 (2) | C5B—H52B | 0.99 |
| O41A—C4A | 1.2120 (18) | ||
| C4A—N3A—C2A | 117.63 (12) | S1A—C5A—H52A | 110.5 |
| C4A—N3A—H3A | 121.2 | H51A—C5A—H52A | 108.7 |
| C2A—N3A—H3A | 121.2 | C2A—S1A—C5A | 91.96 (8) |
| O41A—C4A—N3A | 123.62 (13) | O21A—C2A—N3A | 124.06 (13) |
| O41A—C4A—C5A | 124.08 (17) | O21A—C2A—S1A | 124.09 (11) |
| N3A—C4A—C5A | 112.29 (17) | N3A—C2A—S1A | 111.85 (10) |
| C4A—C5A—S1A | 106.27 (17) | S1B—C5B—H51B | 110.4 |
| C4A—C5A—H51A | 110.5 | S1B—C5B—H52B | 110.4 |
| S1A—C5A—H51A | 110.5 | H51B—C5B—H52B | 108.6 |
| C4A—C5A—H52A | 110.5 | ||
| C2A—N3A—C4A—O41A | −179.62 (14) | C4A—N3A—C2A—O21A | −179.98 (13) |
| C2A—N3A—C4A—C5A | 0.2 (3) | C4A—N3A—C2A—S1A | −0.46 (16) |
| O41A—C4A—C5A—S1A | 179.97 (17) | C5A—S1A—C2A—O21A | 180.0 (2) |
| N3A—C4A—C5A—S1A | 0.2 (3) | C5A—S1A—C2A—N3A | 0.5 (2) |
| C4A—C5A—S1A—C2A | −0.4 (3) |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| N3A—H3A···O21Ai | 0.88 | 1.97 | 2.8465 (16) | 178 |
| C5A—H52A···O41Aii | 0.99 | 2.50 | 3.453 (3) | 161 |
| Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x−1/2, y−1/2, z. |
Experimental details
| Crystal data | |
| Chemical formula | C3H3NO2S |
| Mr | 117.12 |
| Crystal system, space group | Orthorhombic, Pbca |
| Temperature (K) | 150 |
| a, b, c (Å) | 7.2926 (2), 9.3642 (3), 13.1208 (5) |
| V (Å3) | 896.01 (5) |
| Z | 8 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.58 |
| Crystal size (mm) | 0.50 × 0.30 × 0.07 |
| Data collection | |
| Diffractometer | Enraf Nonius KappaCCD area-detector diffractometer |
| Absorption correction | Multi-scan (SORTAV; Blessing, 1995) |
| Tmin, Tmax | 0.759, 0.960 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 5895, 1018, 919 |
| Rint | 0.057 |
| (sin θ/λ)max (Å−1) | 0.650 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.083, 1.09 |
| No. of reflections | 1018 |
| No. of parameters | 70 |
| No. of restraints | 6 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 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···A | D—H | H···A | D···A | D—H···A |
| N3A—H3A···O21Ai | 0.88 | 1.97 | 2.8465 (16) | 178 |
| C5A—H52A···O41Aii | 0.99 | 2.50 | 3.453 (3) | 161 |
| Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x−1/2, y−1/2, z. |
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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 O═C—NH—C═O 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.