2-(4-Chloro­phenyl)-3-cyclo­hexyl­thia­zolidin-4-one

The thia­zolidine ring of the title mol­ecule, C₁₅H₁₈ClNOS, is planar within 0.042 (3) Å and the cyclo­hexane ring adopts a chair conformation. The molecular structure is stabilized by weak C—H...O and C—H...π interactions. In the crystal structure, bifurcated C—H...O interactions link symmetry-related mol­ecules to form dimers.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.048
• wR factor = 0.119
• Data-to-parameter ratio = 16.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2-(4-Chlorophenyl)-3-cyclohexylthiazolidin-4-one

Crystal data

C15H18ClNOS	F(000) = 1248
Mr = 295.81	Dx = 1.348 Mg m^−3
Monoclinic, C2/c	Melting point: 386 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 17.600 (1) Å	Cell parameters from 40 reflections
b = 9.775 (1) Å	θ = 5.1–12.5°
c = 17.089 (1) Å	µ = 0.40 mm^−1
β = 97.33 (1)°	T = 293 K
V = 2916.0 (4) Å^3	Block, colourless
Z = 8	0.25 × 0.20 × 0.18 mm

Data collection

Bruker P4 diffractometer	Rint = 0.023
Radiation source: fine-focus sealed tube	θmax = 26.0°, θmin = 2.3°
Graphite monochromator	h = −1→21
θ–2θ scans	k = −1→12
3556 measured reflections	l = −21→20
2866 independent reflections	3 standard reflections every 97 reflections
1731 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.119	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0439P)^2 + 1.3546P] where P = (Fo^2 + 2Fc^2)/3
2866 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² 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
S1	0.16274 (4)	0.17650 (9)	0.16189 (5)	0.0718 (3)
C2	0.25050 (13)	0.0747 (3)	0.17898 (14)	0.0494 (6)
H2	0.2387	−0.0131	0.2023	0.059*
N3	0.27374 (11)	0.0497 (2)	0.10103 (11)	0.0494 (5)
C4	0.22676 (15)	0.0926 (3)	0.03705 (17)	0.0580 (7)
C5	0.15605 (16)	0.1634 (3)	0.05776 (18)	0.0741 (9)
H5A	0.1108	0.1116	0.0375	0.089*
H5B	0.1520	0.2539	0.0343	0.089*
C6	0.30938 (13)	0.1485 (2)	0.23539 (14)	0.0441 (6)
C7	0.34244 (14)	0.2689 (3)	0.21354 (14)	0.0493 (6)
H7	0.3277	0.3052	0.1636	0.059*
C8	0.39709 (14)	0.3356 (3)	0.26506 (15)	0.0544 (7)
H8	0.4196	0.4160	0.2501	0.065*
C9	0.41754 (15)	0.2808 (3)	0.33901 (15)	0.0559 (7)
C10	0.38527 (16)	0.1633 (3)	0.36243 (15)	0.0617 (8)
H10	0.3996	0.1283	0.4128	0.074*
C11	0.33070 (14)	0.0965 (3)	0.31017 (15)	0.0538 (7)
H11	0.3084	0.0163	0.3256	0.065*
C12	0.33388 (14)	−0.0514 (3)	0.09054 (15)	0.0522 (7)
H12	0.3367	−0.0545	0.0337	0.063*
C13	0.41300 (15)	−0.0137 (3)	0.1280 (2)	0.0753 (9)
H13A	0.4133	−0.0056	0.1846	0.090*
H13B	0.4270	0.0745	0.1080	0.090*
C14	0.47162 (16)	−0.1202 (3)	0.1107 (2)	0.0775 (10)
H14A	0.4767	−0.1184	0.0548	0.093*
H14B	0.5210	−0.0973	0.1396	0.093*
C15	0.44928 (19)	−0.2616 (3)	0.1332 (2)	0.0840 (10)
H15A	0.4857	−0.3269	0.1169	0.101*
H15B	0.4517	−0.2670	0.1901	0.101*
C16	0.37058 (18)	−0.2992 (3)	0.0964 (2)	0.0823 (10)
H16A	0.3568	−0.3872	0.1168	0.099*
H16B	0.3703	−0.3082	0.0398	0.099*
C17	0.31159 (16)	−0.1934 (3)	0.11276 (18)	0.0668 (8)
H17A	0.2625	−0.2167	0.0832	0.080*
H17B	0.3058	−0.1953	0.1684	0.080*
O18	0.23859 (12)	0.0749 (2)	−0.03095 (12)	0.0776 (6)
Cl19	0.48668 (5)	0.36355 (10)	0.40489 (5)	0.0857 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0430 (4)	0.0896 (6)	0.0808 (5)	0.0129 (4)	0.0002 (3)	−0.0059 (5)
C2	0.0405 (13)	0.0515 (16)	0.0565 (15)	0.0016 (12)	0.0073 (11)	0.0039 (13)
N3	0.0439 (11)	0.0568 (13)	0.0463 (12)	0.0012 (11)	0.0015 (9)	−0.0004 (10)
C4	0.0549 (17)	0.0598 (18)	0.0556 (18)	−0.0145 (14)	−0.0069 (14)	0.0023 (14)
C5	0.0517 (17)	0.084 (2)	0.082 (2)	0.0014 (17)	−0.0110 (15)	0.0130 (18)
C6	0.0395 (13)	0.0483 (16)	0.0451 (14)	0.0090 (12)	0.0069 (10)	0.0009 (12)
C7	0.0498 (15)	0.0530 (16)	0.0441 (14)	0.0053 (13)	0.0023 (11)	0.0040 (13)
C8	0.0463 (15)	0.0547 (16)	0.0620 (17)	0.0044 (13)	0.0059 (13)	−0.0004 (14)
C9	0.0461 (15)	0.066 (2)	0.0532 (17)	0.0068 (14)	−0.0016 (12)	−0.0103 (14)
C10	0.0615 (17)	0.077 (2)	0.0438 (15)	0.0167 (17)	−0.0028 (13)	0.0042 (15)
C11	0.0530 (16)	0.0578 (17)	0.0517 (15)	0.0088 (14)	0.0111 (13)	0.0047 (13)
C12	0.0485 (15)	0.0537 (16)	0.0547 (15)	−0.0035 (14)	0.0079 (12)	−0.0071 (13)
C13	0.0467 (16)	0.063 (2)	0.116 (3)	−0.0045 (15)	0.0127 (16)	−0.0204 (18)
C14	0.0474 (17)	0.070 (2)	0.115 (3)	−0.0027 (16)	0.0103 (17)	−0.0280 (19)
C15	0.065 (2)	0.076 (2)	0.109 (3)	0.0181 (19)	0.0023 (18)	−0.007 (2)
C16	0.071 (2)	0.0542 (19)	0.124 (3)	−0.0016 (17)	0.019 (2)	−0.0078 (19)
C17	0.0544 (17)	0.0560 (18)	0.089 (2)	−0.0083 (15)	0.0069 (15)	0.0014 (16)
O18	0.0921 (15)	0.0864 (16)	0.0500 (12)	−0.0093 (12)	−0.0077 (10)	0.0022 (11)
Cl19	0.0716 (5)	0.0996 (7)	0.0783 (5)	0.0010 (5)	−0.0200 (4)	−0.0226 (5)

Geometric parameters (Å, º)

S1—C5	1.773 (3)	C10—H10	0.93
S1—C2	1.829 (2)	C11—H11	0.93
C2—N3	1.463 (3)	C12—C13	1.502 (4)
C2—C6	1.506 (3)	C12—C17	1.504 (4)
C2—H2	0.98	C12—H12	0.98
N3—C4	1.351 (3)	C13—C14	1.521 (4)
N3—C12	1.475 (3)	C13—H13A	0.97
C4—O18	1.219 (3)	C13—H13B	0.97
C4—C5	1.505 (4)	C14—C15	1.500 (4)
C5—H5A	0.97	C14—H14A	0.97
C5—H5B	0.97	C14—H14B	0.97
C6—C11	1.382 (3)	C15—C16	1.492 (4)
C6—C7	1.385 (3)	C15—H15A	0.97
C7—C8	1.382 (3)	C15—H15B	0.97
C7—H7	0.93	C16—C17	1.517 (4)
C8—C9	1.378 (4)	C16—H16A	0.97
C8—H8	0.93	C16—H16B	0.97
C9—C10	1.364 (4)	C17—H17A	0.97
C9—Cl19	1.747 (3)	C17—H17B	0.97
C10—C11	1.388 (4)
C5—S1—C2	93.88 (13)	N3—C12—C13	115.1 (2)
N3—C2—C6	114.42 (19)	N3—C12—C17	111.9 (2)
N3—C2—S1	105.91 (16)	C13—C12—C17	112.1 (2)
C6—C2—S1	109.88 (17)	N3—C12—H12	105.6
N3—C2—H2	108.8	C13—C12—H12	105.6
C6—C2—H2	108.8	C17—C12—H12	105.6
S1—C2—H2	108.8	C12—C13—C14	111.3 (2)
C4—N3—C2	118.1 (2)	C12—C13—H13A	109.4
C4—N3—C12	118.9 (2)	C14—C13—H13A	109.4
C2—N3—C12	120.72 (19)	C12—C13—H13B	109.4
O18—C4—N3	124.5 (3)	C14—C13—H13B	109.4
O18—C4—C5	122.4 (3)	H13A—C13—H13B	108.0
N3—C4—C5	113.0 (2)	C15—C14—C13	112.0 (3)
C4—C5—S1	108.55 (19)	C15—C14—H14A	109.2
C4—C5—H5A	110.0	C13—C14—H14A	109.2
S1—C5—H5A	110.0	C15—C14—H14B	109.2
C4—C5—H5B	110.0	C13—C14—H14B	109.2
S1—C5—H5B	110.0	H14A—C14—H14B	107.9
H5A—C5—H5B	108.4	C16—C15—C14	112.2 (3)
C11—C6—C7	119.2 (2)	C16—C15—H15A	109.2
C11—C6—C2	120.0 (2)	C14—C15—H15A	109.2
C7—C6—C2	120.8 (2)	C16—C15—H15B	109.2
C8—C7—C6	120.8 (2)	C14—C15—H15B	109.2
C8—C7—H7	119.6	H15A—C15—H15B	107.9
C6—C7—H7	119.6	C15—C16—C17	112.0 (3)
C9—C8—C7	118.7 (3)	C15—C16—H16A	109.2
C9—C8—H8	120.7	C17—C16—H16A	109.2
C7—C8—H8	120.7	C15—C16—H16B	109.2
C10—C9—C8	121.8 (2)	C17—C16—H16B	109.2
C10—C9—Cl19	118.9 (2)	H16A—C16—H16B	107.9
C8—C9—Cl19	119.3 (2)	C12—C17—C16	112.1 (2)
C9—C10—C11	119.2 (2)	C12—C17—H17A	109.2
C9—C10—H10	120.4	C16—C17—H17A	109.2
C11—C10—H10	120.4	C12—C17—H17B	109.2
C6—C11—C10	120.4 (3)	C16—C17—H17B	109.2
C6—C11—H11	119.8	H17A—C17—H17B	107.9
C10—C11—H11	119.8
C5—S1—C2—N3	6.17 (19)	C7—C8—C9—C10	−0.1 (4)
C5—S1—C2—C6	130.24 (19)	C7—C8—C9—Cl19	179.87 (19)
C6—C2—N3—C4	−126.3 (2)	C8—C9—C10—C11	0.5 (4)
S1—C2—N3—C4	−5.1 (3)	Cl19—C9—C10—C11	−179.54 (19)
C6—C2—N3—C12	70.7 (3)	C7—C6—C11—C10	−0.8 (4)
S1—C2—N3—C12	−168.12 (17)	C2—C6—C11—C10	179.6 (2)
C2—N3—C4—O18	−178.0 (3)	C9—C10—C11—C6	0.0 (4)
C12—N3—C4—O18	−14.7 (4)	C4—N3—C12—C13	129.3 (3)
C2—N3—C4—C5	0.8 (3)	C2—N3—C12—C13	−67.8 (3)
C12—N3—C4—C5	164.1 (2)	C4—N3—C12—C17	−101.2 (3)
O18—C4—C5—S1	−177.0 (2)	C2—N3—C12—C17	61.7 (3)
N3—C4—C5—S1	4.1 (3)	N3—C12—C13—C14	−177.2 (2)
C2—S1—C5—C4	−5.9 (2)	C17—C12—C13—C14	53.4 (3)
N3—C2—C6—C11	−129.3 (2)	C12—C13—C14—C15	−53.6 (4)
S1—C2—C6—C11	111.8 (2)	C13—C14—C15—C16	53.8 (4)
N3—C2—C6—C7	51.1 (3)	C14—C15—C16—C17	−53.1 (4)
S1—C2—C6—C7	−67.9 (3)	N3—C12—C17—C16	175.8 (2)
C11—C6—C7—C8	1.1 (4)	C13—C12—C17—C16	−53.2 (3)
C2—C6—C7—C8	−179.3 (2)	C15—C16—C17—C12	52.8 (4)
C6—C7—C8—C9	−0.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···O18^i	0.97	2.56	3.226 (4)	126
C7—H7···O18^i	0.93	2.68	3.601 (3)	169
C12—H12···O18	0.98	2.31	2.785 (3)	109
C13—H13A···Cg1	0.97	2.99	3.717 (3)	133

Symmetry code: (i) −x+1/2, −y+1/2, −z.