2-(4-Chloro­phen­yl)-3-phenyl-1,3-thia­zolidin-4-one

In the title compound, C₁₅H₁₂ClNOS, the thia­zolidine ring adopts a twist conformation, with the S and adjacent C (bearing chlorophenyl) atom deviating by −0.140 (1) and 0.158 (2) Å, respectively, from the plane through the other three ring atoms.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.110
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: XPRESS (MacScience, 2002); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and ORTEPII (Johnson, 1976); software used to prepare material for publication: PLATON (Spek, 2003).

2-(4-chlorophenyl)-3-phenyl-1,3-thiazolidin-4-one

Crystal data

C15H12ClNOS	F(000) = 600
Mr = 289.77	Dx = 1.397 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4233 reflections
a = 9.726 (1) Å	θ = 7.6–25.0°
b = 13.752 (2) Å	µ = 0.42 mm^−1
c = 10.397 (1) Å	T = 295 K
β = 97.887 (5)°	Block, pale yellow
V = 1377.5 (3) Å^3	0.25 × 0.20 × 0.20 mm
Z = 4

Data collection

MacScience DIPLabo 32001 diffractometer	1958 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 25.0°, θmin = 7.6°
Detector resolution: 10.0 pixels mm^-1	h = −11→11
ω scans	k = −16→16
4233 measured reflections	l = −12→12
2343 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.110	H-atom parameters constrained
S = 1.13	w = 1/[σ^2(Fo^2) + (0.0521P)^2 + 0.3029P] where P = (Fo^2 + 2Fc^2)/3
2343 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.40 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F^2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2, conventional R-factors R are based on F, with F set to zero for negative F^2. The observed criterion of F^2 > σ(F^2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	−0.38261 (6)	0.31302 (7)	−0.05064 (6)	0.0821 (3)
S9	0.11206 (6)	0.55504 (4)	0.35074 (5)	0.0537 (2)
O12	0.46751 (15)	0.43415 (12)	0.34431 (17)	0.0619 (6)
N13	0.23861 (15)	0.39106 (12)	0.31672 (16)	0.0422 (5)
C2	−0.2399 (2)	0.34102 (16)	0.0637 (2)	0.0496 (7)
C3	−0.1170 (2)	0.36945 (17)	0.0219 (2)	0.0513 (7)
C4	−0.0056 (2)	0.39407 (15)	0.11321 (18)	0.0456 (6)
C5	−0.01590 (19)	0.38965 (14)	0.24505 (18)	0.0398 (6)
C6	−0.1393 (2)	0.35901 (16)	0.28391 (19)	0.0466 (6)
C7	−0.2528 (2)	0.33548 (17)	0.1934 (2)	0.0520 (7)
C8	0.10251 (19)	0.42152 (15)	0.34554 (18)	0.0421 (6)
C10	0.2983 (2)	0.55375 (17)	0.3826 (2)	0.0568 (8)
C11	0.3468 (2)	0.45475 (15)	0.34583 (19)	0.0468 (7)
C14	0.26210 (19)	0.29157 (14)	0.28464 (19)	0.0416 (6)
C15	0.2069 (2)	0.21667 (16)	0.3495 (2)	0.0508 (7)
C16	0.2305 (3)	0.12135 (17)	0.3163 (3)	0.0625 (8)
C17	0.3096 (3)	0.10125 (19)	0.2195 (3)	0.0650 (8)
C18	0.3630 (2)	0.17534 (19)	0.1541 (2)	0.0600 (8)
C19	0.3394 (2)	0.27156 (17)	0.1853 (2)	0.0498 (7)
H3	−0.10950	0.37190	−0.06630	0.0620*
H4	0.07730	0.41380	0.08610	0.0550*
H6	−0.14620	0.35410	0.37200	0.0560*
H7	−0.33610	0.31630	0.22000	0.0620*
H8	0.08790	0.39670	0.43100	0.0510*
H10A	0.33650	0.60360	0.33180	0.0680*
H10B	0.32890	0.56630	0.47380	0.0680*
H15	0.15390	0.23020	0.41530	0.0610*
H16	0.19290	0.07070	0.35950	0.0750*
H17	0.32670	0.03700	0.19850	0.0780*
H18	0.41550	0.16120	0.08820	0.0720*
H19	0.37500	0.32190	0.14010	0.0600*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0527 (4)	0.1293 (7)	0.0596 (4)	−0.0165 (4)	−0.0086 (3)	−0.0163 (4)
S9	0.0522 (3)	0.0502 (3)	0.0569 (4)	0.0020 (2)	0.0011 (2)	−0.0126 (2)
O12	0.0372 (8)	0.0692 (10)	0.0784 (11)	−0.0093 (7)	0.0044 (7)	−0.0007 (8)
N13	0.0345 (8)	0.0451 (9)	0.0468 (9)	−0.0017 (7)	0.0048 (7)	−0.0029 (7)
C2	0.0412 (11)	0.0574 (12)	0.0479 (11)	−0.0010 (9)	−0.0025 (9)	−0.0064 (10)
C3	0.0514 (12)	0.0641 (13)	0.0381 (10)	0.0000 (10)	0.0047 (9)	−0.0039 (10)
C4	0.0399 (10)	0.0559 (12)	0.0420 (10)	−0.0022 (9)	0.0095 (8)	−0.0021 (9)
C5	0.0374 (10)	0.0409 (10)	0.0410 (9)	0.0012 (8)	0.0048 (8)	−0.0018 (8)
C6	0.0430 (11)	0.0578 (12)	0.0399 (10)	−0.0035 (9)	0.0086 (8)	−0.0015 (9)
C7	0.0405 (11)	0.0633 (13)	0.0528 (12)	−0.0089 (9)	0.0085 (9)	−0.0031 (10)
C8	0.0374 (10)	0.0510 (11)	0.0381 (10)	−0.0001 (8)	0.0058 (8)	−0.0024 (8)
C10	0.0537 (13)	0.0530 (13)	0.0609 (13)	−0.0098 (10)	−0.0025 (10)	−0.0054 (10)
C11	0.0409 (11)	0.0541 (12)	0.0442 (11)	−0.0082 (9)	0.0013 (8)	0.0016 (9)
C14	0.0318 (9)	0.0485 (11)	0.0428 (10)	0.0002 (8)	−0.0014 (7)	−0.0035 (9)
C15	0.0482 (11)	0.0504 (12)	0.0545 (12)	−0.0044 (9)	0.0093 (9)	−0.0019 (10)
C16	0.0623 (14)	0.0484 (12)	0.0760 (16)	−0.0048 (11)	0.0069 (12)	0.0001 (12)
C17	0.0559 (13)	0.0520 (13)	0.0847 (17)	0.0059 (11)	0.0012 (12)	−0.0127 (12)
C18	0.0463 (12)	0.0726 (16)	0.0599 (13)	0.0116 (11)	0.0035 (10)	−0.0175 (12)
C19	0.0408 (10)	0.0601 (13)	0.0482 (11)	0.0020 (9)	0.0052 (8)	−0.0010 (10)

Geometric parameters (Å, º)

Cl1—C2	1.742 (2)	C15—C16	1.383 (3)
S9—C8	1.839 (2)	C16—C17	1.376 (4)
S9—C10	1.796 (2)	C17—C18	1.366 (4)
O12—C11	1.210 (2)	C18—C19	1.389 (3)
N13—C8	1.458 (2)	C3—H3	0.9304
N13—C11	1.371 (3)	C4—H4	0.9303
N13—C14	1.434 (3)	C6—H6	0.9299
C2—C3	1.383 (3)	C7—H7	0.9295
C2—C7	1.373 (3)	C8—H8	0.9802
C3—C4	1.381 (3)	C10—H10A	0.9700
C4—C5	1.389 (3)	C10—H10B	0.9695
C5—C6	1.384 (3)	C15—H15	0.9301
C5—C8	1.510 (3)	C16—H16	0.9304
C6—C7	1.387 (3)	C17—H17	0.9306
C10—C11	1.507 (3)	C18—H18	0.9295
C14—C15	1.380 (3)	C19—H19	0.9299
C14—C19	1.386 (3)
Cl1···H7^i	3.0578	C11···H18^vii	2.9794
S9···C16^ii	3.655 (3)	C14···H4	3.0494
S9···H3^iii	3.1202	C15···H8	2.9079
S9···H6^iv	3.1175	C18···H10A^ix	3.0691
O12···C19	2.953 (3)	H3···S9^iii	3.1202
O12···C10^v	3.392 (3)	H4···N13	2.6974
O12···C17^vi	3.289 (3)	H4···C14	3.0494
O12···H17^vi	2.5395	H6···H8	2.3495
O12···H19	2.6788	H6···S9^iv	3.1175
O12···H10B^v	2.5435	H7···Cl1^vii	3.0578
N13···H4	2.6974	H8···C15	2.9079
C4···C14	3.266 (3)	H8···H6	2.3495
C5···C15	3.300 (3)	H8···H15	2.3896
C10···O12^v	3.392 (3)	H10A···C18^vi	3.0691
C14···C4	3.266 (3)	H10A···H18^vi	2.5664
C15···C5	3.300 (3)	H10B···O12^v	2.5435
C15···C19^vii	3.555 (3)	H15···C8	2.7566
C16···S9^viii	3.655 (3)	H15···H8	2.3896
C17···O12^ix	3.289 (3)	H16···C4^viii	3.0726
C19···C15^i	3.555 (3)	H17···O12^ix	2.5395
C19···O12	2.953 (3)	H17···C6^viii	3.0722
C4···H16^ii	3.0726	H18···H10A^ix	2.5664
C6···H17^ii	3.0722	H18···C11^i	2.9794
C8···H15	2.7566	H19···O12	2.6788
C11···H19	2.8547	H19···C11	2.8547
C8—S9—C10	92.36 (10)	C14—C19—C18	119.2 (2)
C8—N13—C11	117.52 (16)	C2—C3—H3	120.52
C8—N13—C14	120.00 (15)	C4—C3—H3	120.56
C11—N13—C14	121.27 (16)	C3—C4—H4	119.60
Cl1—C2—C3	119.34 (16)	C5—C4—H4	119.64
Cl1—C2—C7	119.09 (15)	C5—C6—H6	119.50
C3—C2—C7	121.57 (19)	C7—C6—H6	119.54
C2—C3—C4	118.92 (19)	C2—C7—H7	120.57
C3—C4—C5	120.76 (18)	C6—C7—H7	120.62
C4—C5—C6	118.97 (18)	S9—C8—H8	109.52
C4—C5—C8	121.24 (17)	N13—C8—H8	109.56
C6—C5—C8	119.75 (17)	C5—C8—H8	109.54
C5—C6—C7	120.96 (18)	S9—C10—H10A	110.15
C2—C7—C6	118.80 (18)	S9—C10—H10B	110.18
S9—C8—N13	104.43 (13)	C11—C10—H10A	110.10
S9—C8—C5	109.93 (13)	C11—C10—H10B	110.13
N13—C8—C5	113.71 (16)	H10A—C10—H10B	108.52
S9—C10—C11	107.75 (15)	C14—C15—H15	120.15
O12—C11—N13	124.36 (19)	C16—C15—H15	120.07
O12—C11—C10	123.56 (19)	C15—C16—H16	119.97
N13—C11—C10	112.07 (16)	C17—C16—H16	119.93
N13—C14—C15	120.90 (17)	C16—C17—H17	119.88
N13—C14—C19	118.87 (18)	C18—C17—H17	119.92
C15—C14—C19	120.22 (19)	C17—C18—H18	119.71
C14—C15—C16	119.8 (2)	C19—C18—H18	119.77
C15—C16—C17	120.1 (2)	C14—C19—H19	120.43
C16—C17—C18	120.2 (2)	C18—C19—H19	120.42
C17—C18—C19	120.5 (2)
C10—S9—C8—C5	−144.51 (14)	C3—C4—C5—C6	0.8 (3)
C10—S9—C8—N13	−22.17 (13)	C3—C4—C5—C8	−176.66 (19)
C8—S9—C10—C11	17.88 (15)	C4—C5—C6—C7	−1.8 (3)
C11—N13—C8—S9	22.4 (2)	C6—C5—C8—N13	141.40 (19)
C14—N13—C8—C5	−50.1 (2)	C4—C5—C8—S9	75.5 (2)
C8—N13—C11—O12	169.14 (19)	C6—C5—C8—S9	−101.93 (19)
C11—N13—C8—C5	142.25 (18)	C4—C5—C8—N13	−41.2 (3)
C8—N13—C11—C10	−9.8 (2)	C8—C5—C6—C7	175.7 (2)
C14—N13—C11—C10	−177.28 (17)	C5—C6—C7—C2	1.4 (3)
C14—N13—C8—S9	−169.97 (14)	S9—C10—C11—O12	172.65 (18)
C11—N13—C14—C15	127.0 (2)	S9—C10—C11—N13	−8.4 (2)
C8—N13—C14—C15	−40.2 (3)	C19—C14—C15—C16	0.9 (3)
C11—N13—C14—C19	−54.2 (3)	N13—C14—C15—C16	179.7 (2)
C8—N13—C14—C19	138.65 (19)	C15—C14—C19—C18	−1.4 (3)
C14—N13—C11—O12	1.7 (3)	N13—C14—C19—C18	179.74 (17)
Cl1—C2—C7—C6	−179.22 (17)	C14—C15—C16—C17	0.5 (4)
C7—C2—C3—C4	−0.9 (3)	C15—C16—C17—C18	−1.2 (4)
Cl1—C2—C3—C4	178.24 (17)	C16—C17—C18—C19	0.7 (4)
C3—C2—C7—C6	−0.1 (3)	C17—C18—C19—C14	0.7 (3)
C2—C3—C4—C5	0.6 (3)

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x, y+1/2, −z+1/2; (iii) −x, −y+1, −z; (iv) −x, −y+1, −z+1; (v) −x+1, −y+1, −z+1; (vi) −x+1, y+1/2, −z+1/2; (vii) x, −y+1/2, z+1/2; (viii) −x, y−1/2, −z+1/2; (ix) −x+1, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O12^v	0.97	2.54	3.392 (3)	146
C17—H17···O12^ix	0.93	2.54	3.289 (3)	138

Symmetry codes: (v) −x+1, −y+1, −z+1; (ix) −x+1, y−1/2, −z+1/2.