3-Benzoyl­thia­zolidin-2-one

The title compound, C₁₀H₉NO₂S, was prepared from a condensation reaction of benzoyl chloride and thia­zolidin-2-one. The average C-N bond length to carbonyl groups is 1.393 (2) Å, which is longer then the C-N bond length of a typical acylamine group.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.035
• wR factor = 0.093
• Data-to-parameter ratio = 10.6

checkCIF/PLATON results

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Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2003); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: CrystalStructure; software used to prepare material for publication: CrystalStructure.

(I)

Crystal data

C10H9NO2S	F(000) = 864.00
Mr = 207.25	Dx = 1.414 Mg m^−3
Monoclinic, P21/n	Melting point: 394-395K K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.7107 Å
a = 11.2818 (5) Å	Cell parameters from 12657 reflections
b = 12.4987 (6) Å	θ = 1.5–27.4°
c = 13.8074 (5) Å	µ = 0.30 mm^−1
β = 91.209 (1)°	T = 297 K
V = 1946.52 (15) Å^3	Chunk, colorless
Z = 8	0.38 × 0.35 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	2873 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.026
ω scans	θmax = 27.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −14→12
Tmin = 0.857, Tmax = 0.941	k = −16→16
37290 measured reflections	l = −17→17
4451 independent reflections

Refinement

Refinement on F^2	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.035	w = 1/[0.0013Fo^2 + 1.05σ(Fo^2)]/(4Fo^2)
wR(F^2) = 0.093	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.22 e Å^−3
2879 reflections	Δρmin = −0.26 e Å^−3
271 parameters

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

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	0.16564 (6)	0.14848 (4)	0.48525 (4)	0.0630 (2)
S2	0.76691 (6)	0.17154 (5)	0.49559 (4)	0.0681 (2)
O1	0.1891 (1)	0.2422 (1)	0.65576 (8)	0.0560 (4)
O2	0.1513 (1)	0.5279 (1)	0.5279 (1)	0.0653 (4)
O3	0.6925 (1)	0.2476 (1)	0.66073 (9)	0.0660 (5)
O4	0.4092 (1)	0.3656 (2)	0.5168 (1)	0.0809 (5)
N1	0.1328 (1)	0.3484 (1)	0.5251 (1)	0.0424 (4)
N2	0.5981 (1)	0.3085 (1)	0.52116 (9)	0.0438 (4)
C1	0.1050 (2)	0.2332 (2)	0.3908 (1)	0.0581 (6)
C2	0.1442 (2)	0.3442 (1)	0.4194 (1)	0.0495 (5)
C3	0.1644 (1)	0.2530 (1)	0.5713 (1)	0.0432 (5)
C4	0.1256 (1)	0.4470 (1)	0.5713 (1)	0.0454 (5)
C5	0.0736 (1)	0.4511 (1)	0.6698 (1)	0.0446 (5)
C6	−0.0242 (2)	0.3899 (2)	0.6921 (1)	0.0521 (5)
C7	−0.0813 (2)	0.4067 (2)	0.7784 (2)	0.0645 (7)
C8	−0.0404 (2)	0.4825 (2)	0.8425 (2)	0.0733 (8)
C9	0.0578 (2)	0.5424 (2)	0.8220 (2)	0.0708 (7)
C10	0.1140 (2)	0.5283 (2)	0.7350 (1)	0.0563 (6)
C11	0.7048 (2)	0.2350 (2)	0.3895 (1)	0.0707 (7)
C12	0.5877 (2)	0.2803 (2)	0.4188 (1)	0.0707 (7)
C13	0.6808 (2)	0.2498 (1)	0.5742 (1)	0.0453 (5)
C14	0.5022 (2)	0.3623 (1)	0.5619 (1)	0.0470 (5)
C15	0.5187 (1)	0.4197 (1)	0.6549 (1)	0.0392 (4)
C16	0.4225 (2)	0.4274 (2)	0.7155 (1)	0.0499 (5)
C17	0.4311 (2)	0.4887 (2)	0.7980 (1)	0.0559 (6)
C18	0.5338 (2)	0.5438 (2)	0.8192 (1)	0.0566 (6)
C19	0.6294 (2)	0.5368 (2)	0.7592 (1)	0.0533 (6)
C20	0.6226 (1)	0.4740 (1)	0.6771 (1)	0.0445 (5)
H(1)	0.0200	0.2289	0.3892	0.070*
H(2)	0.1347	0.2132	0.3287	0.070*
H(3)	0.2251	0.3552	0.4016	0.059*
H(4)	0.0949	0.3976	0.3891	0.059*
H(5)	−0.0518	0.3361	0.6474	0.063*
H(6)	−0.1501	0.3653	0.7936	0.078*
H(7)	−0.0805	0.4940	0.9023	0.088*
H(8)	0.0874	0.5943	0.8677	0.085*
H(9)	0.1816	0.5710	0.7191	0.067*
H(10)	0.6949	0.1838	0.3382	0.085*
H(11)	0.7558	0.2917	0.3688	0.086*
H(12)	0.5683	0.3427	0.3811	0.085*
H(13)	0.5268	0.2274	0.4094	0.085*
H(14)	0.3504	0.3901	0.6992	0.060*
H(15)	0.3653	0.4927	0.8408	0.067*
H(16)	0.5389	0.5873	0.8764	0.068*
H(17)	0.7007	0.5758	0.7743	0.064*
H(18)	0.6893	0.4672	0.6356	0.053*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0979 (5)	0.0438 (3)	0.0478 (3)	−0.0011 (3)	0.0112 (3)	−0.0013 (2)
S2	0.0903 (4)	0.0635 (4)	0.0507 (3)	0.0269 (3)	0.0068 (3)	−0.0040 (2)
O1	0.0767 (9)	0.0486 (8)	0.0423 (7)	0.0067 (7)	−0.0068 (6)	0.0066 (5)
O2	0.087 (1)	0.0439 (8)	0.0648 (8)	−0.0070 (7)	0.0023 (7)	0.0104 (7)
O3	0.091 (1)	0.068 (1)	0.0385 (7)	0.0307 (8)	−0.0081 (6)	−0.0007 (6)
O4	0.0508 (9)	0.126 (2)	0.0652 (9)	0.0059 (9)	−0.0222 (7)	−0.0171 (9)
N1	0.0452 (8)	0.0410 (8)	0.0408 (7)	0.0015 (6)	−0.0037 (6)	0.0049 (6)
N2	0.0528 (9)	0.0439 (9)	0.0346 (7)	0.0025 (7)	−0.0064 (6)	−0.0018 (6)
C1	0.066 (1)	0.067 (1)	0.0411 (9)	−0.009 (1)	0.0020 (8)	−0.0026 (9)
C2	0.054 (1)	0.055 (1)	0.0400 (9)	0.0004 (9)	−0.0020 (8)	0.0091 (8)
C3	0.046 (1)	0.041 (1)	0.0429 (9)	−0.0013 (8)	0.0017 (7)	0.0045 (7)
C4	0.043 (1)	0.042 (1)	0.0498 (9)	0.0018 (8)	−0.0068 (7)	0.0053 (8)
C5	0.0422 (9)	0.041 (1)	0.051 (1)	0.0068 (8)	−0.0063 (7)	0.0036 (8)
C6	0.043 (1)	0.055 (1)	0.059 (1)	0.0052 (9)	−0.0044 (8)	0.0012 (9)
C7	0.046 (1)	0.078 (2)	0.069 (1)	0.011 (1)	0.006 (1)	0.008 (1)
C8	0.073 (2)	0.086 (2)	0.061 (1)	0.028 (1)	0.009 (1)	−0.005 (1)
C9	0.084 (2)	0.067 (2)	0.062 (1)	0.014 (1)	−0.007 (1)	−0.016 (1)
C10	0.059 (1)	0.047 (1)	0.062 (1)	0.0028 (9)	−0.0071 (9)	−0.0024 (9)
C11	0.107 (2)	0.065 (1)	0.040 (1)	0.007 (1)	0.011 (1)	0.0002 (9)
C12	0.101 (2)	0.072 (1)	0.039 (1)	0.017 (1)	−0.016 (1)	−0.010 (1)
C13	0.058 (1)	0.040 (1)	0.0384 (9)	0.0013 (8)	−0.0016 (8)	0.0004 (7)
C14	0.043 (1)	0.052 (1)	0.0453 (9)	−0.0032 (8)	−0.0076 (8)	0.0024 (8)
C15	0.0375 (9)	0.0357 (9)	0.0442 (9)	0.0022 (7)	−0.0029 (7)	0.0032 (7)
C16	0.0382 (9)	0.056 (1)	0.055 (1)	−0.0005 (8)	−0.0006 (8)	−0.0004 (9)
C17	0.049 (1)	0.065 (1)	0.055 (1)	0.008 (1)	0.0089 (9)	−0.0065 (9)
C18	0.060 (1)	0.053 (1)	0.057 (1)	0.008 (1)	−0.0001 (9)	−0.0153 (9)
C19	0.048 (1)	0.046 (1)	0.065 (1)	−0.0053 (9)	−0.0048 (9)	−0.0108 (9)
C20	0.0418 (9)	0.040 (1)	0.0512 (9)	−0.0012 (8)	0.0029 (7)	0.0002 (8)

Geometric parameters (Å, º)

S1—C1	1.803 (2)	C7—C8	1.371 (3)
S1—C3	1.766 (2)	C7—H(6)	0.960
S2—C11	1.795 (2)	C8—C9	1.372 (4)
S2—C13	1.767 (2)	C8—H(7)	0.960
O1—C3	1.202 (2)	C9—C10	1.382 (3)
O2—C4	1.213 (2)	C9—H(8)	0.960
O3—C13	1.200 (2)	C10—H(9)	0.960
O4—C14	1.209 (2)	C11—C12	1.501 (4)
N1—C2	1.468 (2)	C11—H(10)	0.960
N1—C3	1.395 (2)	C11—H(11)	0.960
N1—C4	1.391 (2)	C12—H(12)	0.960
N2—C12	1.459 (2)	C12—H(13)	0.960
N2—C13	1.385 (2)	C14—C15	1.480 (2)
N2—C14	1.401 (2)	C15—C16	1.388 (2)
C1—C2	1.507 (3)	C15—C20	1.383 (2)
C1—H(1)	0.960	C16—C17	1.374 (3)
C1—H(2)	0.960	C16—H(14)	0.960
C2—H(3)	0.960	C17—C18	1.373 (3)
C2—H(4)	0.960	C17—H(15)	0.960
C4—C5	1.494 (2)	C18—C19	1.376 (3)
C5—C6	1.384 (3)	C18—H(16)	0.960
C5—C10	1.388 (3)	C19—C20	1.380 (3)
C6—C7	1.382 (3)	C19—H(17)	0.960
C6—H(5)	0.960	C20—H(18)	0.960
C1—S1—C3	92.52 (9)	H(8)—C9—C8	120.3
C11—S2—C13	92.6 (1)	H(9)—C10—C5	119.3
C2—N1—C3	113.4 (1)	H(9)—C10—C9	120.5
C2—N1—C4	119.6 (1)	C5—C10—C9	120.2 (2)
C3—N1—C4	124.3 (1)	C12—C11—H(10)	111.1
C12—N2—C13	115.1 (2)	C12—C11—H(11)	109.8
C12—N2—C14	117.2 (2)	C12—C11—S2	106.2 (1)
C13—N2—C14	124.0 (1)	H(10)—C11—H(11)	109.5
C2—C1—H(1)	110.1	H(10)—C11—S2	110.2
C2—C1—H(2)	111.6	H(11)—C11—S2	110.1
C2—C1—S1	104.2 (1)	H(12)—C12—H(13)	109.5
H(1)—C1—H(2)	109.5	H(12)—C12—N2	109.9
H(1)—C1—S1	110.3	H(12)—C12—C11	110.6
H(2)—C1—S1	111.0	H(13)—C12—N2	109.9
H(3)—C2—H(4)	109.5	H(13)—C12—C11	109.5
H(3)—C2—N1	110.7	N2—C12—C11	107.4 (2)
H(3)—C2—C1	109.9	S2—C13—O3	123.3 (1)
H(4)—C2—N1	110.3	S2—C13—N2	110.0 (1)
H(4)—C2—C1	111.2	O3—C13—N2	126.7 (2)
N1—C2—C1	105.2 (1)	C15—C14—O4	121.5 (2)
S1—C3—O1	124.4 (1)	C15—C14—N2	119.8 (1)
S1—C3—N1	109.3 (1)	O4—C14—N2	118.6 (2)
O1—C3—N1	126.3 (2)	C16—C15—C20	120.1 (2)
C5—C4—O2	121.5 (2)	C16—C15—C14	118.1 (2)
C5—C4—N1	118.4 (2)	C20—C15—C14	121.4 (2)
O2—C4—N1	119.7 (2)	C17—C16—H(14)	120.7
C6—C5—C10	119.5 (2)	C17—C16—C15	119.7 (2)
C6—C5—C4	120.9 (2)	H(14)—C16—C15	119.6
C10—C5—C4	119.0 (2)	C18—C17—H(15)	120.1
C7—C6—H(5)	120.7	C18—C17—C16	120.1 (2)
C7—C6—C5	119.7 (2)	H(15)—C17—C16	119.8
H(5)—C6—C5	119.6	C19—C18—H(16)	119.8
C8—C7—H(6)	119.6	C19—C18—C17	120.5 (2)
C8—C7—C6	120.4 (2)	H(16)—C18—C17	119.7
H(6)—C7—C6	120.0	C20—C19—H(17)	120.0
C9—C8—H(7)	119.6	C20—C19—C18	120.0 (2)
C9—C8—C7	120.4 (2)	H(17)—C19—C18	120.1
H(7)—C8—C7	120.0	H(18)—C20—C15	119.8
C10—C9—H(8)	119.9	H(18)—C20—C19	120.7
C10—C9—C8	119.8 (2)	C15—C20—C19	119.6 (2)