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The title compound, C10H10N2O2S, was prepared from a condensation reaction of phenyl isocyanate and thia­zolidin-2-one. There are two independent mol­ecules in the asymmetric unit, showing similar conformations. The C-N single bonds linked to the phenyl ring have lengths 1.408 (3) and 1.414 (3) Å, and are longer than the C-N bonds to the carbonyl groups [1.342 (3)-1.370 (3) Å].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804008621/ob6361sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804008621/ob6361Isup2.hkl
Contains datablock I

CCDC reference: 239265

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.041
  • wR factor = 0.108
  • Data-to-parameter ratio = 8.9

checkCIF/PLATON results

No syntax errors found



Alert level C REFNR01_ALERT_3_C Ratio of reflections to parameters is < 10 for a centrosymmetric structure sine(theta)/lambda 0.6493 Proportion of unique data used 0.5462 Ratio reflections to parameters 8.8900 PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.90 PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 8.89
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1993); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: Please provide missing details; software used to prepare material for publication: CrystalStructure.

2-Oxo-N-phenylthiazolidine-3-carboxamide top
Crystal data top
C10H10N2O2SF(000) = 928.00
Mr = 222.27Dx = 1.428 Mg m3
Monoclinic, P21/cMelting point = 396–397 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.7107 Å
a = 22.201 (1) ÅCell parameters from 10002 reflections
b = 8.1176 (3) Åθ = 2.3–27.5°
c = 11.8485 (5) ŵ = 0.29 mm1
β = 104.480 (1)°T = 293 K
V = 2067.49 (15) Å3Chunk, colourless
Z = 80.29 × 0.25 × 0.24 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2564 reflections with F2 > 2.0σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.029
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 2828
Tmin = 0.826, Tmax = 0.932k = 109
16794 measured reflectionsl = 1515
4736 independent reflections
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.041 w = 4Fo2/[0.0017Fo2 + σ(Fo2)]
wR(F2) = 0.108(Δ/σ)max < 0.001
S = 1.00Δρmax = 0.15 e Å3
4736 reflectionsΔρmin = 0.25 e Å3
291 parameters
Special details top

Refinement. Refinement using reflections with F2 > 2.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.18192 (3)0.7286 (1)0.19217 (7)0.0775 (2)
S20.69149 (3)0.7316 (1)0.86963 (7)0.0820 (3)
O10.10065 (8)0.8016 (2)0.3876 (2)0.0726 (6)
O20.02193 (8)0.4844 (3)0.2874 (2)0.0838 (7)
O30.60790 (8)0.8055 (2)0.9827 (2)0.0738 (6)
O40.48736 (8)0.4900 (2)0.7611 (2)0.0824 (6)
N10.07064 (8)0.6124 (2)0.2677 (2)0.0543 (6)
N20.01223 (9)0.6679 (2)0.4274 (2)0.0572 (6)
N30.57952 (9)0.6161 (2)0.8339 (2)0.0566 (6)
N40.49563 (8)0.6676 (2)0.9129 (2)0.0564 (6)
C10.1109 (1)0.7205 (3)0.2993 (2)0.0575 (7)
C20.1598 (1)0.5655 (5)0.1093 (3)0.094 (1)
C30.0930 (1)0.5342 (4)0.1541 (2)0.081 (1)
C40.0081 (1)0.5826 (3)0.3278 (2)0.0560 (7)
C50.0733 (1)0.6728 (3)0.5000 (2)0.0543 (7)
C60.0845 (1)0.7852 (3)0.5901 (2)0.0680 (8)
C70.1434 (1)0.8011 (4)0.6626 (3)0.084 (1)
C80.1910 (1)0.7059 (4)0.6462 (3)0.086 (1)
C90.1796 (1)0.5922 (4)0.5578 (3)0.082 (1)
C100.1212 (1)0.5742 (3)0.4831 (2)0.0676 (8)
C110.6193 (1)0.7235 (3)0.9048 (2)0.0605 (7)
C120.6708 (1)0.5706 (5)0.7638 (3)0.096 (1)
C130.6042 (1)0.5361 (4)0.7439 (2)0.083 (1)
C140.5169 (1)0.5853 (3)0.8326 (2)0.0559 (7)
C150.4345 (1)0.6682 (3)0.9275 (2)0.0534 (6)
C160.4215 (1)0.7793 (3)1.0074 (2)0.0638 (8)
C170.3630 (1)0.7890 (4)1.0248 (3)0.0777 (9)
C180.3160 (1)0.6891 (4)0.9636 (3)0.0770 (9)
C190.3291 (1)0.5783 (4)0.8862 (2)0.0740 (9)
C200.3873 (1)0.5659 (3)0.8664 (2)0.0611 (7)
H10.01840.73220.45220.070*
H20.52560.73310.96690.066*
H30.16800.59830.02910.112*
H40.18320.46800.11570.112*
H50.08610.41770.16270.098*
H60.07050.57740.10130.098*
H70.05100.85210.60240.081*
H80.15120.87930.72530.097*
H90.23220.71810.69590.099*
H100.21300.52370.54730.098*
H110.11380.49530.42090.082*
H120.69420.47310.79200.116*
H130.68000.60520.69230.115*
H140.58260.57840.66910.101*
H150.59760.41940.74610.101*
H160.45420.84851.05070.075*
H170.35430.86631.07990.094*
H180.27480.69670.97520.093*
H190.29660.50710.84430.086*
H200.39580.48840.81120.071*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0636 (4)0.0850 (5)0.0829 (5)0.0031 (4)0.0166 (4)0.0094 (4)
S20.0728 (5)0.0899 (6)0.0831 (5)0.0154 (4)0.0194 (4)0.0048 (4)
O10.079 (1)0.065 (1)0.077 (1)0.0143 (9)0.0246 (9)0.011 (1)
O20.073 (1)0.101 (2)0.081 (1)0.015 (1)0.026 (1)0.031 (1)
O30.079 (1)0.065 (1)0.074 (1)0.0171 (9)0.0135 (9)0.018 (1)
O40.077 (1)0.095 (1)0.070 (1)0.017 (1)0.0089 (9)0.034 (1)
N10.060 (1)0.055 (1)0.053 (1)0.0021 (9)0.0218 (9)0.0023 (9)
N20.062 (1)0.052 (1)0.060 (1)0.0034 (9)0.0199 (9)0.0047 (9)
N30.067 (1)0.052 (1)0.048 (1)0.0025 (9)0.0086 (9)0.0020 (9)
N40.061 (1)0.051 (1)0.053 (1)0.0081 (9)0.0057 (9)0.0065 (9)
C10.062 (1)0.052 (1)0.063 (1)0.000 (1)0.024 (1)0.008 (1)
C20.070 (2)0.130 (3)0.079 (2)0.009 (2)0.016 (2)0.020 (2)
C30.086 (2)0.102 (2)0.057 (1)0.001 (2)0.018 (1)0.017 (2)
C40.064 (1)0.053 (1)0.056 (1)0.001 (1)0.025 (1)0.001 (1)
C50.063 (2)0.045 (1)0.057 (1)0.001 (1)0.018 (1)0.009 (1)
C60.079 (2)0.060 (2)0.063 (2)0.001 (1)0.014 (1)0.000 (1)
C70.099 (2)0.074 (2)0.070 (2)0.009 (2)0.003 (2)0.001 (1)
C80.073 (2)0.081 (2)0.092 (2)0.010 (2)0.001 (2)0.022 (2)
C90.069 (2)0.076 (2)0.101 (2)0.012 (1)0.020 (2)0.021 (2)
C100.067 (2)0.059 (2)0.079 (2)0.005 (1)0.021 (1)0.008 (1)
C110.069 (2)0.052 (1)0.055 (1)0.008 (1)0.006 (1)0.008 (1)
C120.080 (2)0.117 (3)0.091 (2)0.006 (2)0.022 (2)0.016 (2)
C130.089 (2)0.101 (2)0.062 (2)0.013 (2)0.024 (1)0.014 (2)
C140.063 (1)0.052 (1)0.047 (1)0.002 (1)0.002 (1)0.001 (1)
C150.062 (1)0.042 (1)0.051 (1)0.000 (1)0.004 (1)0.010 (1)
C160.075 (2)0.053 (1)0.061 (1)0.005 (1)0.013 (1)0.005 (1)
C170.087 (2)0.069 (2)0.079 (2)0.004 (2)0.025 (2)0.004 (1)
C180.069 (2)0.074 (2)0.090 (2)0.003 (1)0.024 (1)0.003 (2)
C190.063 (2)0.073 (2)0.079 (2)0.007 (1)0.004 (1)0.004 (1)
C200.067 (2)0.053 (1)0.057 (1)0.005 (1)0.005 (1)0.001 (1)
Geometric parameters (Å, º) top
S1—C11.761 (2)C15—C161.389 (4)
S1—C21.789 (4)C15—C201.390 (3)
S2—C111.754 (3)C16—C171.367 (4)
S2—C121.789 (4)C17—C181.376 (4)
O1—C11.209 (3)C18—C191.367 (4)
O2—C41.212 (3)C19—C201.374 (4)
O3—C111.216 (3)N2—H10.9600
O4—C141.212 (3)N4—H20.9600
N1—C11.370 (3)C2—H30.9600
N1—C31.458 (3)C2—H40.9600
N1—C41.414 (3)C3—H50.9600
N2—C41.344 (3)C3—H60.9600
N2—C51.413 (3)C6—H70.9600
N3—C111.369 (3)C7—H80.9600
N3—C131.468 (4)C8—H90.9600
N3—C141.408 (3)C9—H100.9600
N4—C141.342 (3)C10—H110.9600
N4—C151.411 (3)C12—H120.9600
C2—C31.465 (4)C12—H130.9600
C5—C61.379 (3)C13—H140.9600
C5—C101.385 (4)C13—H150.9600
C6—C71.380 (4)C16—H160.9600
C7—C81.361 (5)C17—H170.9600
C8—C91.372 (5)C18—H180.9600
C9—C101.383 (4)C19—H190.9600
C12—C131.465 (4)C20—H200.9600
S1—C1—O1123.0 (2)S1—C2—H4109.7599
S1—C1—N1110.8 (2)S2—C12—H12109.6820
C2—S1—C192.8 (1)S2—C12—H13109.3420
S1—C2—C3108.7 (2)N1—C3—H5108.7972
S2—C11—O3122.4 (2)N1—C3—H6109.2078
S2—C11—N3111.5 (2)H1—N2—C4116.1558
C12—S2—C1192.9 (1)H1—N2—C5116.2988
S2—C12—C13108.9 (2)N3—C13—H14108.6980
O1—C1—N1126.2 (2)N3—C13—H15109.1674
O2—C4—N1118.8 (2)H2—N4—C14116.1698
O2—C4—N2126.0 (2)H2—N4—C15116.2744
O3—C11—N3126.1 (2)H3—C2—C3109.4407
O4—C14—N3118.8 (2)H4—C2—C3110.3275
O4—C14—N4126.0 (2)C2—C3—H5109.2839
C3—N1—C1115.8 (2)C2—C3—H6110.2092
C4—N1—C1126.7 (2)H4—C2—H3109.4578
N1—C3—C2109.9 (3)H6—C3—H5109.4608
C4—N1—C3117.1 (2)C5—C6—H7119.6217
N1—C4—N2115.2 (2)C5—C10—H11120.4704
C5—N2—C4127.5 (2)H7—C6—C7120.1655
N2—C5—C10123.4 (2)C6—C7—H8120.1386
N2—C5—C6116.8 (2)H8—C7—C8119.3369
C13—N3—C11115.2 (2)C7—C8—H9120.5530
C14—N3—C11127.1 (2)C8—C9—H10119.1233
N3—C13—C12110.1 (2)H9—C8—C9120.2390
C14—N3—C13117.4 (2)C9—C10—H11120.9982
N3—C14—N4115.2 (2)H10—C9—C10119.2089
C15—N4—C14127.6 (2)H12—C12—C13109.4934
N4—C15—C20123.8 (2)H13—C12—C13109.9542
N4—C15—C16117.2 (2)C12—C13—H14109.4145
C10—C5—C6119.8 (2)C12—C13—H15109.9301
C5—C6—C7120.2 (3)H13—C12—H12109.4636
C5—C10—C9118.5 (2)H15—C13—H14109.4643
C6—C7—C8120.5 (3)C15—C16—H16119.0037
C7—C8—C9119.2 (3)C15—C20—H20119.7256
C8—C9—C10121.7 (3)H16—C16—C17120.4878
C20—C15—C16119.0 (2)C16—C17—H17120.0549
C15—C16—C17120.5 (2)H17—C17—C18119.2338
C15—C20—C19119.1 (2)C17—C18—H18120.7348
C16—C17—C18120.7 (3)C18—C19—H19118.9775
C17—C18—C19118.7 (3)H18—C18—C19120.5273
C18—C19—C20122.0 (2)C19—C20—H20121.1692
S1—C2—H3109.0976H19—C19—C20119.0665
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H1···O10.961.882.663 (3)137
N4—H2···O30.961.892.668 (2)137
 

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