3-[2-Cyclo­propyl-1-(2-fluoro­phen­yl)-2-oxoeth­yl]-5-(4-methyl­sulfanyl­benzyl­idene)-1,3-thia­zolidine-2,4-dione

Suresh, J.; Venkateshan, M.; Ponnuchamy, S.; Kumar, R.R.; Lakshman, P.L.N.

doi:10.1107/S1600536812051987

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o188

doi:10.1107/S1600536812051987

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3-[2-Cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-5-(4-methylsulfanylbenzylidene)-1,3-thiazolidine-2,4-dione

J. Suresh,^a M. Venkateshan,^a S. Ponnuchamy,^b R. Ranjith Kumar ^c and P. L. Nilantha Lakshman ^d ^*

^aDepartment of Physics, The Madura College, Madurai 625 011, India, ^bOrchid Chemicals & Pharmaceuticals Ltd, R&D Center, Chennai 600 119, India, ^cDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, and ^dDepartment of Food Science and Technology, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
^*Correspondence e-mail: plakshmannilantha@ymail.com

(Received 26 December 2012; accepted 28 December 2012; online 4 January 2013)

In the title compound, C₂₂H₁₈FNO₃S₂, the five-membered thiazolidine 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 cyclopropane, fluorobenzene and methylthiobenzene rings, respectively. The sum of the bond angles around the thiazolidine ring N atom (359.6°) indicates sp² hybridization. The molecular structure features intramolecular C—H⋯S, C—H⋯F and C—H⋯O interactions. In the crystal, no significant intermolecular 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

C₂₂H₁₈FNO₃S₂
M_r = 427.49
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.149
S = 1.02
3838 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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

Data collection: 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 (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812051987/tk5185sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812051987/tk5185Isup3.cml

checkCIF report

Comment top

Thiazolidines are an important class of heteroaromatic compounds and have widespread applications from ranging from pharmaceuticals (Barreca et al., 2002) to materials (Botti et al., 1996). Thiazolidinediones (TZDs), which are known to sensitize tissues to insulin, have been developed and clinically used as anti-diabetic agents. They have been shown to reduce plasma glucose, lipid, and insulin levels, and are used for the treatment of type 2 diabetes (Day, 1999; Spiegelman, 1998). In view of this we have synthesized the title compound to study its crystal structure.

In the title compound, Fig. 1, the five-membered thiazolidine is nearly planar with a r.m.s. deviation of 0.003 Å. The 4-methyl sulfonyl benzylidine ring is nearly coplanar with the central thiazolidine ring as indicated by the dihedral angle of 8.35 (1)°. The 2-fluorobenzene and cyclopropyl rings make dihedral angles of 73.16 (17) and 70.2 (3)° with the thiazolidine ring, respectively. The sum of bond angles around N is 359.6° which confirms sp²hybridization. In the cyclopropyl ring the mean C—C bond length is 1.504 (3) Å and the mean C—C—C bond angle is 60.0 (2)°; these are unexceptional. The molecular structure features intramolecular C—H···S, C—H···F C—H···O interactions (Table 1).

Related literature top

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

Experimental top

A mixture of 5-(4-methylsulfanyl-benzylidenethiazolidine-2,4-dione (1 mmol), 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone (1 mmol) and sodium bicarbonate (3 mmol) were taken in DMF and stirred for 6 h at 25–35 °C. After completion of the reaction as evident by TLC, (eluent: 7:3 / hexane:ethyl acetate) the mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine (20 ml) twice and then with water. The solvent was distilled off to obtain a viscous paste to which diisopropyl ether (5 volumes) was added. The resultant solid was filtered and washed with diisopropyl ether. The product was recrystallized from its methanol solution. Melting point: 414.5–415.9 Yield: 83.5%

Computing details top

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

Figures top

Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.

3-[2-Cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-5-(4- methylsulfanylbenzylidene)-1,3-thiazolidine-2,4-dione top

Crystal data top

C₂₂H₁₈FNO₃S₂	F(000) = 888
M_r = 427.49	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0683P)² + 0.8976P] where P = (F_o² + 2F_c²)/3
3838 reflections	(Δ/σ)_max < 0.001
262 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₂H₁₈FNO₃S₂	V = 2097.7 (13) Å³
M_r = 427.49	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.657 (3) Å	µ = 0.29 mm⁻¹
b = 15.799 (5) Å	T = 293 K
c = 17.425 (6) Å	0.23 × 0.21 × 0.19 mm
β = 95.641 (5)°

Data collection top

Bruker Kappa APEXII diffractometer	3838 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2429 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.974	R_int = 0.033
19651 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 1.02	Δρ_max = 0.32 e Å⁻³
3838 reflections	Δρ_min = −0.26 e Å⁻³
262 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₂₂H₁₈FNO₃S₂
M_r	427.49
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.657 (3), 15.799 (5), 17.425 (6)
β (°)	95.641 (5)
V (Å³)	2097.7 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.23 × 0.21 × 0.19

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.967, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	19651, 3838, 2429
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.604

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.149, 1.02
No. of reflections	3838
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.26

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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

Acknowledgements

SP thanks the management, Orchid Chemicals & Pharmaceuticals Ltd, Chennai, for providing laboratory facilities. JS thanks the UGC for the FIST support. JS and MV thank the management of The Madura College for their encouragement and support. RRK thanks the DST, New Delhi, for funds under the fast-track scheme (No·SR/FT/CS-073/2009).

References

Barreca, M. L., Balzarini, J., Chimirri, A., De Clercq, E., De Luca, L., Holtje, H. D., Holtje, M., Monforte, A. M., Monforte, P., Pannecouque, C., Rao, A. & Zappala, M. (2002). J. Med. Chem. 45, 5410–5413. Web of Science CrossRef PubMed CAS Google Scholar
Botti, P., Pallin, T. D. & Tam, J. P. (1996). J. Am. Chem. Soc. 118, 10018–10024. CrossRef CAS Web of Science Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Day, C. (1999). Diabet. Med. 16, 179–192. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spiegelman, B. M. (1998). Diabetes, 47, 507–514. Web of Science CrossRef CAS PubMed Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-[2-Cyclo­propyl-1-(2-fluoro­phen­yl)-2-oxoeth­yl]-5-(4-methyl­sulfanyl­benzyl­­idene)-1,3-thia­zolidine-2,4-dione

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Experimental

Crystal data

Data collection

Refinement

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References

organic compounds

3-[2-Cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-5-(4-methylsulfanylbenzylidene)-1,3-thiazolidine-2,4-dione