2-Oxo-N-phenyl­thia­zolidine-3-carbox­amide

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].

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

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Computing details

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

Crystal data

C10H10N2O2S	F(000) = 928.00
Mr = 222.27	Dx = 1.428 Mg m^−3
Monoclinic, P21/c	Melting point = 396–397 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.7107 Å
a = 22.201 (1) Å	Cell parameters from 10002 reflections
b = 8.1176 (3) Å	θ = 2.3–27.5°
c = 11.8485 (5) Å	µ = 0.29 mm^−1
β = 104.480 (1)°	T = 293 K
V = 2067.49 (15) Å^3	Chunk, colourless
Z = 8	0.29 × 0.25 × 0.24 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	2564 reflections with F^2 > 2.0σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.029
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −28→28
Tmin = 0.826, Tmax = 0.932	k = −10→9
16794 measured reflections	l = −15→15
4736 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.041	w = 4Fo^2/[0.0017Fo^2 + σ(Fo^2)]
wR(F^2) = 0.108	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.15 e Å^−3
4736 reflections	Δρmin = −0.25 e Å^−3
291 parameters

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	−0.18192 (3)	0.7286 (1)	0.19217 (7)	0.0775 (2)
S2	0.69149 (3)	0.7316 (1)	0.86963 (7)	0.0820 (3)
O1	−0.10065 (8)	0.8016 (2)	0.3876 (2)	0.0726 (6)
O2	0.02193 (8)	0.4844 (3)	0.2874 (2)	0.0838 (7)
O3	0.60790 (8)	0.8055 (2)	0.9827 (2)	0.0738 (6)
O4	0.48736 (8)	0.4900 (2)	0.7611 (2)	0.0824 (6)
N1	−0.07064 (8)	0.6124 (2)	0.2677 (2)	0.0543 (6)
N2	0.01223 (9)	0.6679 (2)	0.4274 (2)	0.0572 (6)
N3	0.57952 (9)	0.6161 (2)	0.8339 (2)	0.0566 (6)
N4	0.49563 (8)	0.6676 (2)	0.9129 (2)	0.0564 (6)
C1	−0.1109 (1)	0.7205 (3)	0.2993 (2)	0.0575 (7)
C2	−0.1598 (1)	0.5655 (5)	0.1093 (3)	0.094 (1)
C3	−0.0930 (1)	0.5342 (4)	0.1541 (2)	0.081 (1)
C4	−0.0081 (1)	0.5826 (3)	0.3278 (2)	0.0560 (7)
C5	0.0733 (1)	0.6728 (3)	0.5000 (2)	0.0543 (7)
C6	0.0845 (1)	0.7852 (3)	0.5901 (2)	0.0680 (8)
C7	0.1434 (1)	0.8011 (4)	0.6626 (3)	0.084 (1)
C8	0.1910 (1)	0.7059 (4)	0.6462 (3)	0.086 (1)
C9	0.1796 (1)	0.5922 (4)	0.5578 (3)	0.082 (1)
C10	0.1212 (1)	0.5742 (3)	0.4831 (2)	0.0676 (8)
C11	0.6193 (1)	0.7235 (3)	0.9048 (2)	0.0605 (7)
C12	0.6708 (1)	0.5706 (5)	0.7638 (3)	0.096 (1)
C13	0.6042 (1)	0.5361 (4)	0.7439 (2)	0.083 (1)
C14	0.5169 (1)	0.5853 (3)	0.8326 (2)	0.0559 (7)
C15	0.4345 (1)	0.6682 (3)	0.9275 (2)	0.0534 (6)
C16	0.4215 (1)	0.7793 (3)	1.0074 (2)	0.0638 (8)
C17	0.3630 (1)	0.7890 (4)	1.0248 (3)	0.0777 (9)
C18	0.3160 (1)	0.6891 (4)	0.9636 (3)	0.0770 (9)
C19	0.3291 (1)	0.5783 (4)	0.8862 (2)	0.0740 (9)
C20	0.3873 (1)	0.5659 (3)	0.8664 (2)	0.0611 (7)
H1	−0.0184	0.7322	0.4522	0.070*
H2	0.5256	0.7331	0.9669	0.066*
H3	−0.1680	0.5983	0.0291	0.112*
H4	−0.1832	0.4680	0.1157	0.112*
H5	−0.0861	0.4177	0.1627	0.098*
H6	−0.0705	0.5774	0.1013	0.098*
H7	0.0510	0.8521	0.6024	0.081*
H8	0.1512	0.8793	0.7253	0.097*
H9	0.2322	0.7181	0.6959	0.099*
H10	0.2130	0.5237	0.5473	0.098*
H11	0.1138	0.4953	0.4209	0.082*
H12	0.6942	0.4731	0.7920	0.116*
H13	0.6800	0.6052	0.6923	0.115*
H14	0.5826	0.5784	0.6691	0.101*
H15	0.5976	0.4194	0.7461	0.101*
H16	0.4542	0.8485	1.0507	0.075*
H17	0.3543	0.8663	1.0799	0.094*
H18	0.2748	0.6967	0.9752	0.093*
H19	0.2966	0.5071	0.8443	0.086*
H20	0.3958	0.4884	0.8112	0.071*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0636 (4)	0.0850 (5)	0.0829 (5)	0.0031 (4)	0.0166 (4)	0.0094 (4)
S2	0.0728 (5)	0.0899 (6)	0.0831 (5)	−0.0154 (4)	0.0194 (4)	0.0048 (4)
O1	0.079 (1)	0.065 (1)	0.077 (1)	0.0143 (9)	0.0246 (9)	−0.011 (1)
O2	0.073 (1)	0.101 (2)	0.081 (1)	0.015 (1)	0.026 (1)	−0.031 (1)
O3	0.079 (1)	0.065 (1)	0.074 (1)	−0.0171 (9)	0.0135 (9)	−0.018 (1)
O4	0.077 (1)	0.095 (1)	0.070 (1)	−0.017 (1)	0.0089 (9)	−0.034 (1)
N1	0.060 (1)	0.055 (1)	0.053 (1)	−0.0021 (9)	0.0218 (9)	−0.0023 (9)
N2	0.062 (1)	0.052 (1)	0.060 (1)	0.0034 (9)	0.0199 (9)	−0.0047 (9)
N3	0.067 (1)	0.052 (1)	0.048 (1)	−0.0025 (9)	0.0086 (9)	−0.0020 (9)
N4	0.061 (1)	0.051 (1)	0.053 (1)	−0.0081 (9)	0.0057 (9)	−0.0065 (9)
C1	0.062 (1)	0.052 (1)	0.063 (1)	−0.000 (1)	0.024 (1)	0.008 (1)
C2	0.070 (2)	0.130 (3)	0.079 (2)	−0.009 (2)	0.016 (2)	−0.020 (2)
C3	0.086 (2)	0.102 (2)	0.057 (1)	−0.001 (2)	0.018 (1)	−0.017 (2)
C4	0.064 (1)	0.053 (1)	0.056 (1)	−0.001 (1)	0.025 (1)	0.001 (1)
C5	0.063 (2)	0.045 (1)	0.057 (1)	−0.001 (1)	0.018 (1)	0.009 (1)
C6	0.079 (2)	0.060 (2)	0.063 (2)	0.001 (1)	0.014 (1)	0.000 (1)
C7	0.099 (2)	0.074 (2)	0.070 (2)	−0.009 (2)	0.003 (2)	0.001 (1)
C8	0.073 (2)	0.081 (2)	0.092 (2)	−0.010 (2)	−0.001 (2)	0.022 (2)
C9	0.069 (2)	0.076 (2)	0.101 (2)	0.012 (1)	0.020 (2)	0.021 (2)
C10	0.067 (2)	0.059 (2)	0.079 (2)	0.005 (1)	0.021 (1)	0.008 (1)
C11	0.069 (2)	0.052 (1)	0.055 (1)	−0.008 (1)	0.006 (1)	0.008 (1)
C12	0.080 (2)	0.117 (3)	0.091 (2)	0.006 (2)	0.022 (2)	−0.016 (2)
C13	0.089 (2)	0.101 (2)	0.062 (2)	−0.013 (2)	0.024 (1)	−0.014 (2)
C14	0.063 (1)	0.052 (1)	0.047 (1)	−0.002 (1)	0.002 (1)	0.001 (1)
C15	0.062 (1)	0.042 (1)	0.051 (1)	0.000 (1)	0.004 (1)	0.010 (1)
C16	0.075 (2)	0.053 (1)	0.061 (1)	−0.005 (1)	0.013 (1)	−0.005 (1)
C17	0.087 (2)	0.069 (2)	0.079 (2)	0.004 (2)	0.025 (2)	−0.004 (1)
C18	0.069 (2)	0.074 (2)	0.090 (2)	0.003 (1)	0.024 (1)	0.003 (2)
C19	0.063 (2)	0.073 (2)	0.079 (2)	−0.007 (1)	0.004 (1)	0.004 (1)
C20	0.067 (2)	0.053 (1)	0.057 (1)	−0.005 (1)	0.005 (1)	−0.001 (1)

Geometric parameters (Å, º)

S1—C1	1.761 (2)	C15—C16	1.389 (4)
S1—C2	1.789 (4)	C15—C20	1.390 (3)
S2—C11	1.754 (3)	C16—C17	1.367 (4)
S2—C12	1.789 (4)	C17—C18	1.376 (4)
O1—C1	1.209 (3)	C18—C19	1.367 (4)
O2—C4	1.212 (3)	C19—C20	1.374 (4)
O3—C11	1.216 (3)	N2—H1	0.9600
O4—C14	1.212 (3)	N4—H2	0.9600
N1—C1	1.370 (3)	C2—H3	0.9600
N1—C3	1.458 (3)	C2—H4	0.9600
N1—C4	1.414 (3)	C3—H5	0.9600
N2—C4	1.344 (3)	C3—H6	0.9600
N2—C5	1.413 (3)	C6—H7	0.9600
N3—C11	1.369 (3)	C7—H8	0.9600
N3—C13	1.468 (4)	C8—H9	0.9600
N3—C14	1.408 (3)	C9—H10	0.9600
N4—C14	1.342 (3)	C10—H11	0.9600
N4—C15	1.411 (3)	C12—H12	0.9600
C2—C3	1.465 (4)	C12—H13	0.9600
C5—C6	1.379 (3)	C13—H14	0.9600
C5—C10	1.385 (4)	C13—H15	0.9600
C6—C7	1.380 (4)	C16—H16	0.9600
C7—C8	1.361 (5)	C17—H17	0.9600
C8—C9	1.372 (5)	C18—H18	0.9600
C9—C10	1.383 (4)	C19—H19	0.9600
C12—C13	1.465 (4)	C20—H20	0.9600
S1—C1—O1	123.0 (2)	S1—C2—H4	109.7599
S1—C1—N1	110.8 (2)	S2—C12—H12	109.6820
C2—S1—C1	92.8 (1)	S2—C12—H13	109.3420
S1—C2—C3	108.7 (2)	N1—C3—H5	108.7972
S2—C11—O3	122.4 (2)	N1—C3—H6	109.2078
S2—C11—N3	111.5 (2)	H1—N2—C4	116.1558
C12—S2—C11	92.9 (1)	H1—N2—C5	116.2988
S2—C12—C13	108.9 (2)	N3—C13—H14	108.6980
O1—C1—N1	126.2 (2)	N3—C13—H15	109.1674
O2—C4—N1	118.8 (2)	H2—N4—C14	116.1698
O2—C4—N2	126.0 (2)	H2—N4—C15	116.2744
O3—C11—N3	126.1 (2)	H3—C2—C3	109.4407
O4—C14—N3	118.8 (2)	H4—C2—C3	110.3275
O4—C14—N4	126.0 (2)	C2—C3—H5	109.2839
C3—N1—C1	115.8 (2)	C2—C3—H6	110.2092
C4—N1—C1	126.7 (2)	H4—C2—H3	109.4578
N1—C3—C2	109.9 (3)	H6—C3—H5	109.4608
C4—N1—C3	117.1 (2)	C5—C6—H7	119.6217
N1—C4—N2	115.2 (2)	C5—C10—H11	120.4704
C5—N2—C4	127.5 (2)	H7—C6—C7	120.1655
N2—C5—C10	123.4 (2)	C6—C7—H8	120.1386
N2—C5—C6	116.8 (2)	H8—C7—C8	119.3369
C13—N3—C11	115.2 (2)	C7—C8—H9	120.5530
C14—N3—C11	127.1 (2)	C8—C9—H10	119.1233
N3—C13—C12	110.1 (2)	H9—C8—C9	120.2390
C14—N3—C13	117.4 (2)	C9—C10—H11	120.9982
N3—C14—N4	115.2 (2)	H10—C9—C10	119.2089
C15—N4—C14	127.6 (2)	H12—C12—C13	109.4934
N4—C15—C20	123.8 (2)	H13—C12—C13	109.9542
N4—C15—C16	117.2 (2)	C12—C13—H14	109.4145
C10—C5—C6	119.8 (2)	C12—C13—H15	109.9301
C5—C6—C7	120.2 (3)	H13—C12—H12	109.4636
C5—C10—C9	118.5 (2)	H15—C13—H14	109.4643
C6—C7—C8	120.5 (3)	C15—C16—H16	119.0037
C7—C8—C9	119.2 (3)	C15—C20—H20	119.7256
C8—C9—C10	121.7 (3)	H16—C16—C17	120.4878
C20—C15—C16	119.0 (2)	C16—C17—H17	120.0549
C15—C16—C17	120.5 (2)	H17—C17—C18	119.2338
C15—C20—C19	119.1 (2)	C17—C18—H18	120.7348
C16—C17—C18	120.7 (3)	C18—C19—H19	118.9775
C17—C18—C19	118.7 (3)	H18—C18—C19	120.5273
C18—C19—C20	122.0 (2)	C19—C20—H20	121.1692
S1—C2—H3	109.0976	H19—C19—C20	119.0665

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···O1	0.96	1.88	2.663 (3)	137
N4—H2···O3	0.96	1.89	2.668 (2)	137