3-[2-Cyclo-propyl-1-(2-fluoro-phen-yl)-2-oxoeth-yl]-5-(4-methyl-sulfanyl-benzyl-idene)-1,3-thia-zolidine-2,4-dione.

In the title compound, C(22)H(18)FNO(3)S(2), the five-membered thia-zolidine ring is planar (r.m.s. deviation = 0.003 Å) and forms dihedral angles of 70.2 (3), 73.16 (17) and 10.32 (14)° with the cyclo-propane, fluoro-benzene and methyl-thio-benzene rings, respectively. The sum of the bond angles around the thia-zolidine ring N atom (359.6°) indicates sp(2) hybridization. The mol-ecular structure features intra-molecular C-H⋯S, C-H⋯F and C-H⋯O inter-actions. In the crystal, no significant inter-molecular contacts were apparent.

Related literature

For general properties of thia­zolidines, see: Botti et al. (1996 ▶); Spiegelman (1998 ▶); Day (1999 ▶); Barreca et al. (2002 ▶).

Experimental

Crystal data

<span class="Chemical">C22H18FNO3S2

M = 427.49

Monoclinic,

a = 7.657 (3) Å

b = 15.799 (5) Å

c = 17.425 (6) Å

β = 95.641 (5)°

V = 2097.7 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 293 K

0.23 × 0.21 × 0.19 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.967, T max = 0.974

19651 measured reflections

3838 independent reflections

2429 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.149

S = 1.02

3838 reflections

262 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.26 e Å−3

Data collection: <span class="Gene">APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (<span class="Chemical">Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812051987/tk5185sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812051987/tk5185Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812051987/tk5185Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H18FNO3S2	F(000) = 888
Mr = 427.49	Dx = 1.354 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2000 reflections
a = 7.657 (3) Å	θ = 2–25°
b = 15.799 (5) Å	µ = 0.29 mm−1
c = 17.425 (6) Å	T = 293 K
β = 95.641 (5)°	Block, colourless
V = 2097.7 (13) Å3	0.23 × 0.21 × 0.19 mm
Z = 4

Bruker Kappa APEXII diffractometer	3838 independent reflections
Radiation source: fine-focus sealed tube	2429 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: 0 pixels mm-1	θmax = 25.4°, θmin = 2.4°
ω and φ scans	h = −5→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −18→19
Tmin = 0.967, Tmax = 0.974	l = −21→20
19651 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0683P)2 + 0.8976P] where P = (Fo2 + 2Fc2)/3
3838 reflections	(Δ/σ)max < 0.001
262 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	−0.0768 (4)	0.07851 (19)	0.35525 (16)	0.0603 (7)
C2	0.2318 (3)	0.02818 (18)	0.34213 (15)	0.0539 (7)
C3	0.1614 (4)	0.08537 (18)	0.28013 (16)	0.0589 (7)
C4	−0.1107 (4)	0.16162 (18)	0.23261 (15)	0.0575 (7)
H4	−0.0273	0.1811	0.1972	0.069*
C5	−0.2414 (4)	0.1066 (2)	0.18456 (17)	0.0648 (8)
C6	−0.3427 (4)	0.1473 (2)	0.11919 (18)	0.0769 (9)
H6	−0.3314	0.2089	0.1151	0.092*
C7	−0.5155 (5)	0.1103 (3)	0.0911 (2)	0.1003 (13)
H7A	−0.5547	0.0611	0.1181	0.120*
H7B	−0.6082	0.1489	0.0719	0.120*
C8	−0.3702 (6)	0.0993 (3)	0.0454 (2)	0.1102 (14)
H8A	−0.3720	0.1311	−0.0023	0.132*
H8B	−0.3185	0.0433	0.0439	0.132*
C9	−0.1842 (4)	0.24062 (19)	0.26535 (16)	0.0640 (8)
C10	−0.3536 (5)	0.2472 (2)	0.28457 (19)	0.0892 (11)
H10	−0.4307	0.2019	0.2766	0.107*
C11	−0.4098 (8)	0.3236 (4)	0.3166 (2)	0.1203 (18)
H11	−0.5241	0.3296	0.3295	0.144*
C12	−0.2909 (11)	0.3889 (3)	0.3283 (3)	0.137 (3)
H12	−0.3257	0.4385	0.3511	0.164*
C13	−0.1253 (10)	0.3835 (3)	0.3079 (3)	0.131 (2)
H13	−0.0495	0.4295	0.3144	0.157*
C14	−0.0726 (6)	0.3109 (2)	0.27810 (19)	0.0832 (10)
C15	0.3898 (3)	−0.00777 (18)	0.34052 (16)	0.0566 (7)
H15	0.4507	0.0093	0.2996	0.068*
C16	0.4815 (3)	−0.06842 (17)	0.39142 (15)	0.0523 (6)
C17	0.4287 (4)	−0.09486 (18)	0.46215 (16)	0.0589 (7)
H17	0.3247	−0.0741	0.4782	0.071*
C18	0.5269 (4)	−0.15058 (19)	0.50819 (16)	0.0605 (7)
H18	0.4890	−0.1671	0.5550	0.073*
C19	0.6831 (4)	−0.18290 (19)	0.48574 (16)	0.0611 (7)
C20	0.7347 (4)	−0.1587 (2)	0.41522 (17)	0.0677 (8)
H20	0.8375	−0.1804	0.3987	0.081*
C21	0.6358 (3)	−0.10303 (19)	0.36966 (16)	0.0609 (7)
H21	0.6730	−0.0877	0.3224	0.073*
C22	0.9974 (6)	−0.2703 (4)	0.5069 (3)	0.142 (2)
H22A	1.0729	−0.3067	0.5394	0.212*
H22B	1.0571	−0.2180	0.4990	0.212*
H22C	0.9670	−0.2974	0.4581	0.212*
N	−0.0076 (3)	0.11071 (14)	0.29086 (12)	0.0543 (6)
O1	−0.2202 (3)	0.09354 (14)	0.37424 (13)	0.0807 (7)
O2	0.2345 (3)	0.10769 (15)	0.22512 (13)	0.0868 (7)
O3	−0.2558 (4)	0.03221 (15)	0.19915 (15)	0.0952 (8)
F	0.0895 (4)	0.30462 (16)	0.25692 (14)	0.1184 (8)
S1	0.07690 (9)	0.01156 (5)	0.40749 (4)	0.0652 (3)
S2	0.80371 (12)	−0.24929 (6)	0.55177 (5)	0.0834 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0589 (16)	0.0646 (18)	0.0587 (18)	0.0013 (14)	0.0130 (14)	0.0060 (15)
C2	0.0573 (15)	0.0623 (17)	0.0433 (15)	−0.0036 (13)	0.0116 (12)	−0.0021 (13)
C3	0.0620 (16)	0.0637 (18)	0.0523 (17)	0.0018 (14)	0.0132 (14)	0.0010 (14)
C4	0.0649 (16)	0.0608 (18)	0.0476 (16)	0.0013 (14)	0.0102 (13)	0.0069 (14)
C5	0.0770 (19)	0.062 (2)	0.0559 (18)	0.0030 (16)	0.0072 (15)	0.0013 (15)
C6	0.094 (2)	0.079 (2)	0.0565 (19)	−0.0150 (18)	−0.0036 (17)	0.0109 (17)
C7	0.086 (2)	0.123 (3)	0.089 (3)	−0.018 (2)	−0.004 (2)	0.033 (2)
C8	0.122 (3)	0.153 (4)	0.054 (2)	−0.023 (3)	0.002 (2)	−0.007 (2)
C9	0.091 (2)	0.0552 (19)	0.0455 (16)	0.0119 (17)	0.0063 (15)	0.0055 (14)
C10	0.113 (3)	0.092 (3)	0.065 (2)	0.044 (2)	0.022 (2)	0.0144 (19)
C11	0.163 (4)	0.132 (4)	0.071 (3)	0.078 (4)	0.034 (3)	0.033 (3)
C12	0.263 (8)	0.078 (3)	0.070 (3)	0.063 (5)	0.022 (4)	0.011 (3)
C13	0.257 (7)	0.064 (3)	0.068 (3)	−0.001 (4)	−0.005 (4)	0.008 (2)
C14	0.134 (3)	0.063 (2)	0.0523 (19)	0.007 (2)	0.007 (2)	0.0114 (17)
C15	0.0565 (15)	0.0679 (18)	0.0470 (16)	−0.0024 (14)	0.0129 (12)	−0.0016 (14)
C16	0.0510 (14)	0.0604 (17)	0.0456 (15)	−0.0017 (13)	0.0055 (12)	−0.0055 (13)
C17	0.0545 (15)	0.0688 (19)	0.0547 (17)	0.0030 (14)	0.0121 (13)	−0.0046 (14)
C18	0.0659 (17)	0.0689 (19)	0.0475 (16)	0.0000 (15)	0.0087 (14)	−0.0011 (14)
C19	0.0616 (16)	0.0678 (19)	0.0524 (18)	0.0053 (14)	−0.0018 (14)	−0.0051 (14)
C20	0.0572 (16)	0.088 (2)	0.0592 (18)	0.0125 (16)	0.0126 (14)	−0.0009 (17)
C21	0.0596 (16)	0.077 (2)	0.0477 (16)	0.0033 (15)	0.0133 (13)	0.0007 (15)
C22	0.106 (3)	0.218 (6)	0.103 (3)	0.088 (3)	0.020 (3)	0.042 (3)
N	0.0560 (12)	0.0618 (14)	0.0459 (13)	0.0031 (11)	0.0089 (10)	0.0055 (11)
O1	0.0627 (12)	0.0963 (17)	0.0874 (16)	0.0178 (11)	0.0300 (11)	0.0260 (13)
O2	0.0850 (14)	0.1093 (18)	0.0723 (14)	0.0220 (13)	0.0382 (12)	0.0331 (13)
O3	0.127 (2)	0.0603 (15)	0.0921 (18)	−0.0026 (14)	−0.0193 (15)	0.0020 (13)
F	0.134 (2)	0.1123 (19)	0.1068 (18)	−0.0420 (16)	0.0020 (15)	0.0186 (14)
S1	0.0581 (4)	0.0814 (6)	0.0582 (5)	0.0072 (4)	0.0169 (3)	0.0164 (4)
S2	0.0848 (6)	0.1018 (7)	0.0621 (5)	0.0229 (5)	−0.0005 (4)	0.0087 (5)

C1—O1	1.201 (3)	C10—H10	0.9300
C1—N	1.384 (3)	C11—C12	1.378 (8)
C1—S1	1.767 (3)	C11—H11	0.9300
C2—C15	1.340 (4)	C12—C13	1.353 (8)
C2—C3	1.470 (4)	C12—H12	0.9300
C2—S1	1.743 (3)	C13—C14	1.337 (6)
C3—O2	1.209 (3)	C13—H13	0.9300
C3—N	1.385 (3)	C14—F	1.333 (4)
C4—N	1.464 (3)	C15—C16	1.441 (4)
C4—C9	1.504 (4)	C15—H15	0.9300
C4—C5	1.515 (4)	C16—C21	1.388 (4)
C4—H4	0.9800	C16—C17	1.398 (4)
C5—O3	1.209 (4)	C17—C18	1.366 (4)
C5—C6	1.463 (4)	C17—H17	0.9300
C6—C7	1.486 (5)	C18—C19	1.391 (4)
C6—C8	1.490 (5)	C18—H18	0.9300
C6—H6	0.9800	C19—C20	1.381 (4)
C7—C8	1.441 (5)	C19—S2	1.752 (3)
C7—H7A	0.9700	C20—C21	1.363 (4)
C7—H7B	0.9700	C20—H20	0.9300
C8—H8A	0.9700	C21—H21	0.9300
C8—H8B	0.9700	C22—S2	1.774 (4)
C9—C10	1.375 (5)	C22—H22A	0.9600
C9—C14	1.406 (5)	C22—H22B	0.9600
C10—C11	1.413 (6)	C22—H22C	0.9600
O1—C1—N	125.7 (3)	C12—C11—H11	120.8
O1—C1—S1	123.8 (2)	C10—C11—H11	120.8
N—C1—S1	110.43 (19)	C13—C12—C11	122.5 (5)
C15—C2—C3	120.8 (2)	C13—C12—H12	118.8
C15—C2—S1	128.6 (2)	C11—C12—H12	118.8
C3—C2—S1	110.44 (19)	C14—C13—C12	118.9 (6)
O2—C3—N	122.3 (3)	C14—C13—H13	120.6
O2—C3—C2	126.7 (3)	C12—C13—H13	120.6
N—C3—C2	111.0 (2)	F—C14—C13	119.7 (5)
N—C4—C9	112.9 (2)	F—C14—C9	117.8 (3)
N—C4—C5	110.5 (2)	C13—C14—C9	122.5 (5)
C9—C4—C5	115.8 (2)	C2—C15—C16	131.0 (3)
N—C4—H4	105.6	C2—C15—H15	114.5
C9—C4—H4	105.6	C16—C15—H15	114.5
C5—C4—H4	105.6	C21—C16—C17	116.8 (3)
O3—C5—C6	122.6 (3)	C21—C16—C15	118.1 (2)
O3—C5—C4	120.7 (3)	C17—C16—C15	125.2 (2)
C6—C5—C4	116.6 (3)	C18—C17—C16	121.4 (3)
C5—C6—C7	118.0 (3)	C18—C17—H17	119.3
C5—C6—C8	117.8 (3)	C16—C17—H17	119.3
C7—C6—C8	57.9 (2)	C17—C18—C19	120.7 (3)
C5—C6—H6	116.7	C17—C18—H18	119.7
C7—C6—H6	116.7	C19—C18—H18	119.7
C8—C6—H6	116.7	C20—C19—C18	118.5 (3)
C8—C7—C6	61.2 (2)	C20—C19—S2	124.9 (2)
C8—C7—H7A	117.6	C18—C19—S2	116.6 (2)
C6—C7—H7A	117.6	C21—C20—C19	120.4 (3)
C8—C7—H7B	117.6	C21—C20—H20	119.8
C6—C7—H7B	117.6	C19—C20—H20	119.8
H7A—C7—H7B	114.8	C20—C21—C16	122.3 (3)
C7—C8—C6	60.9 (2)	C20—C21—H21	118.9
C7—C8—H8A	117.7	C16—C21—H21	118.9
C6—C8—H8A	117.7	S2—C22—H22A	109.5
C7—C8—H8B	117.7	S2—C22—H22B	109.5
C6—C8—H8B	117.7	H22A—C22—H22B	109.5
H8A—C8—H8B	114.8	S2—C22—H22C	109.5
C10—C9—C14	118.4 (3)	H22A—C22—H22C	109.5
C10—C9—C4	123.5 (3)	H22B—C22—H22C	109.5
C14—C9—C4	118.1 (3)	C1—N—C3	116.1 (2)
C9—C10—C11	119.5 (4)	C1—N—C4	122.7 (2)
C9—C10—H10	120.3	C3—N—C4	120.8 (2)
C11—C10—H10	120.3	C2—S1—C1	91.99 (13)
C12—C11—C10	118.4 (5)	C19—S2—C22	103.42 (18)
C15—C2—C3—O2	−2.4 (5)	C2—C15—C16—C21	171.7 (3)
S1—C2—C3—O2	−178.1 (3)	C2—C15—C16—C17	−9.2 (5)
C15—C2—C3—N	176.1 (2)	C21—C16—C17—C18	1.5 (4)
S1—C2—C3—N	0.4 (3)	C15—C16—C17—C18	−177.7 (3)
N—C4—C5—O3	3.6 (4)	C16—C17—C18—C19	−0.1 (4)
C9—C4—C5—O3	−126.4 (3)	C17—C18—C19—C20	−1.2 (4)
N—C4—C5—C6	−174.5 (2)	C17—C18—C19—S2	176.6 (2)
C9—C4—C5—C6	55.6 (4)	C18—C19—C20—C21	1.2 (5)
O3—C5—C6—C7	26.8 (5)	S2—C19—C20—C21	−176.4 (2)
C4—C5—C6—C7	−155.3 (3)	C19—C20—C21—C16	0.2 (5)
O3—C5—C6—C8	−39.7 (5)	C17—C16—C21—C20	−1.5 (4)
C4—C5—C6—C8	138.3 (3)	C15—C16—C21—C20	177.7 (3)
C5—C6—C7—C8	−106.9 (4)	O1—C1—N—C3	179.6 (3)
C5—C6—C8—C7	107.2 (4)	S1—C1—N—C3	0.0 (3)
N—C4—C9—C10	−98.6 (3)	O1—C1—N—C4	−6.4 (5)
C5—C4—C9—C10	30.1 (4)	S1—C1—N—C4	174.0 (2)
N—C4—C9—C14	80.3 (3)	O2—C3—N—C1	178.3 (3)
C5—C4—C9—C14	−151.0 (3)	C2—C3—N—C1	−0.3 (3)
C14—C9—C10—C11	−0.3 (5)	O2—C3—N—C4	4.2 (4)
C4—C9—C10—C11	178.6 (3)	C2—C3—N—C4	−174.3 (2)
C9—C10—C11—C12	−0.7 (6)	C9—C4—N—C1	58.9 (3)
C10—C11—C12—C13	2.3 (7)	C5—C4—N—C1	−72.5 (3)
C11—C12—C13—C14	−2.8 (8)	C9—C4—N—C3	−127.4 (3)
C12—C13—C14—F	179.3 (4)	C5—C4—N—C3	101.1 (3)
C12—C13—C14—C9	1.7 (6)	C15—C2—S1—C1	−175.6 (3)
C10—C9—C14—F	−177.9 (3)	C3—C2—S1—C1	−0.3 (2)
C4—C9—C14—F	3.1 (4)	O1—C1—S1—C2	−179.4 (3)
C10—C9—C14—C13	−0.2 (5)	N—C1—S1—C2	0.2 (2)
C4—C9—C14—C13	−179.2 (3)	C20—C19—S2—C22	2.2 (4)
C3—C2—C15—C16	−176.3 (3)	C18—C19—S2—C22	−175.6 (3)
S1—C2—C15—C16	−1.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···F	0.98	2.35	2.740 (4)	103
C4—H4···O2	0.98	2.33	2.792 (4)	108
C15—H15···O2	0.93	2.53	2.884 (4)	103
C17—H17···S1	0.93	2.55	3.238 (3)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯F	0.98	2.35	2.740 (4)	103
C4—H4⋯O2	0.98	2.33	2.792 (4)	108
C15—H15⋯O2	0.93	2.53	2.884 (4)	103
C17—H17⋯S1	0.93	2.55	3.238 (3)	131