3-(2H-1,3-Benzodioxol-5-ylmeth-yl)-2-(2-meth-oxy-phen-yl)-1,3-thia-zolidin-4-one.

The title mol-ecule, C(18)H(17)NO(4)S, features a 1,3-thia-zolidine ring that is twisted about the S-C(methyl-ene) bond. With reference to this ring, the 1,3-benzodioxole and benzene rings lie to either side and form dihedral angles of 69.72 (16) and 83.60 (14)°, respectively, with the central ring. Significant twisting in the mol-ecule is confirmed by the dihedral angle of 79.91 (13)° formed between the outer rings. Linear supra-molecular chains along the a-axis direction mediated by C-H⋯O inter-actions feature in the crystal packing.

Related literature

For background to the biological activity of thia­zolidinones, see: Cunico et al. (2008a ▶); Solomon et al. (2007 ▶); Kavitha et al. (2006 ▶); Sharma et al. (2006 ▶); Ravichandran et al. (2009 ▶); Rao et al. (2004 ▶). For background to the synthesis, see: Cunico et al. (2008b ▶); Rawal et al. (2008 ▶), Gomes et al. (2010 ▶), Neuenfeldt et al. (2011 ▶). For related studies on the synthesis and biological evaluation of thia­zolidinones, see: Cunico et al. (2006 ▶, 2007 ▶). For a thia­zolidinone structure, see: Neuenfeldt et al. (2009 ▶).

Experimental

Crystal data

C18H17NO4S

M = 343.39

Monoclinic,

a = 6.8137 (3) Å

b = 12.5753 (7) Å

c = 18.5071 (9) Å

β = 91.825 (3)°

V = 1584.96 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 120 K

0.16 × 0.06 × 0.05 mm

Data collection

Bruker–Nonius APEXII CCD camera on κ-goniostat diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.553, T max = 0.746

21683 measured reflections

3625 independent reflections

1935 reflections with I > 2σ(I)

R int = 0.159

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.180

S = 1.02

3625 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.43 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811041262/hb6438sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041262/hb6438Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811041262/hb6438Isup3.cml

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

C18H17NO4S	F(000) = 720
Mr = 343.39	Dx = 1.439 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7149 reflections
a = 6.8137 (3) Å	θ = 2.9–27.5°
b = 12.5753 (7) Å	µ = 0.23 mm−1
c = 18.5071 (9) Å	T = 120 K
β = 91.825 (3)°	Block, colourless
V = 1584.96 (14) Å3	0.16 × 0.06 × 0.05 mm
Z = 4

Bruker–Nonius APEXII CCD camera on κ-goniostat diffractometer	3625 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	1935 reflections with I > 2σ(I)
10cm confocal mirrors	Rint = 0.159
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 3.2°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −15→16
Tmin = 0.553, Tmax = 0.746	l = −23→24
21683 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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0754P)2] where P = (Fo2 + 2Fc2)/3
3625 reflections	(Δ/σ)max < 0.001
218 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
S1	0.48794 (13)	0.72256 (9)	0.17227 (5)	0.0365 (3)
O1	0.3856 (3)	0.60647 (19)	−0.01787 (12)	0.0321 (6)
O2	0.9136 (3)	0.76552 (19)	0.24212 (12)	0.0291 (6)
O3	1.2380 (3)	0.9163 (2)	−0.11437 (14)	0.0358 (6)
O4	1.0102 (3)	1.05303 (19)	−0.11655 (13)	0.0328 (6)
N1	0.6500 (4)	0.6556 (2)	0.05355 (13)	0.0231 (6)
C1	0.7138 (4)	0.6948 (3)	0.12420 (17)	0.0246 (8)
H1	0.7849	0.7635	0.1174	0.029*
C2	0.4558 (5)	0.6343 (3)	0.04091 (18)	0.0260 (8)
C3	0.3391 (5)	0.6492 (3)	0.10759 (19)	0.0358 (9)
H3A	0.3034	0.5792	0.1279	0.043*
H3B	0.2167	0.6888	0.0957	0.043*
C4	0.8488 (4)	0.6199 (3)	0.16581 (17)	0.0239 (8)
C5	0.9521 (4)	0.6609 (3)	0.22695 (17)	0.0236 (8)
C6	1.0804 (5)	0.5969 (3)	0.26668 (18)	0.0278 (8)
H6	1.1525	0.6253	0.3070	0.033*
C7	1.1036 (5)	0.4905 (3)	0.24740 (18)	0.0300 (9)
H7	1.1917	0.4465	0.2747	0.036*
C8	0.9991 (5)	0.4487 (3)	0.18869 (18)	0.0289 (8)
H8	1.0127	0.3757	0.1765	0.035*
C9	0.8740 (5)	0.5139 (3)	0.14744 (17)	0.0260 (8)
H9	0.8053	0.4856	0.1063	0.031*
C10	0.9967 (5)	0.8064 (3)	0.30861 (18)	0.0321 (9)
H10A	0.9499	0.7642	0.3491	0.048*
H10B	0.9568	0.8807	0.3145	0.048*
H10C	1.1402	0.8022	0.3077	0.048*
C11	0.7881 (5)	0.6555 (3)	−0.00479 (17)	0.0281 (8)
H11A	0.7309	0.6146	−0.0460	0.034*
H11B	0.9099	0.6188	0.0119	0.034*
C12	0.8399 (5)	0.7660 (3)	−0.03050 (16)	0.0254 (8)
C13	1.0282 (5)	0.7820 (3)	−0.05777 (17)	0.0245 (8)
H13	1.1244	0.7273	−0.0570	0.029*
C14	1.0652 (4)	0.8808 (3)	−0.08553 (18)	0.0264 (8)
C15	1.1839 (5)	1.0137 (3)	−0.1505 (2)	0.0372 (9)
H15A	1.1562	1.0004	−0.2026	0.045*
H15B	1.2917	1.0662	−0.1456	0.045*
C16	0.9303 (5)	0.9626 (3)	−0.08612 (18)	0.0285 (8)
C17	0.7480 (5)	0.9499 (3)	−0.05749 (17)	0.0280 (8)
H17	0.6563	1.0068	−0.0562	0.034*
C18	0.7038 (5)	0.8489 (3)	−0.03018 (17)	0.0260 (8)
H18	0.5781	0.8366	−0.0110	0.031*

	U11	U22	U33	U12	U13	U23
S1	0.0270 (5)	0.0496 (7)	0.0329 (5)	0.0028 (4)	0.0009 (4)	−0.0113 (5)
O1	0.0314 (13)	0.0343 (16)	0.0300 (14)	0.0017 (11)	−0.0083 (11)	−0.0041 (12)
O2	0.0332 (13)	0.0292 (15)	0.0245 (13)	0.0021 (11)	−0.0070 (10)	−0.0028 (11)
O3	0.0291 (13)	0.0316 (16)	0.0472 (16)	0.0008 (11)	0.0082 (11)	0.0041 (12)
O4	0.0329 (14)	0.0290 (15)	0.0367 (14)	−0.0010 (11)	0.0049 (11)	0.0016 (12)
N1	0.0231 (14)	0.0276 (17)	0.0183 (13)	−0.0027 (12)	−0.0017 (11)	−0.0009 (12)
C1	0.0246 (17)	0.026 (2)	0.0232 (17)	−0.0041 (14)	−0.0026 (14)	−0.0039 (15)
C2	0.0269 (17)	0.023 (2)	0.0279 (19)	−0.0020 (14)	−0.0041 (15)	0.0032 (16)
C3	0.0270 (18)	0.050 (3)	0.0305 (19)	−0.0054 (17)	0.0024 (15)	−0.0001 (18)
C4	0.0199 (16)	0.030 (2)	0.0223 (17)	−0.0005 (14)	0.0019 (13)	0.0035 (15)
C5	0.0213 (16)	0.028 (2)	0.0218 (17)	−0.0039 (14)	0.0000 (13)	−0.0007 (15)
C6	0.0255 (17)	0.035 (2)	0.0225 (18)	−0.0062 (16)	−0.0016 (14)	0.0015 (16)
C7	0.0307 (19)	0.029 (2)	0.030 (2)	0.0074 (16)	0.0020 (16)	0.0040 (17)
C8	0.0306 (19)	0.027 (2)	0.0294 (19)	−0.0010 (15)	0.0006 (15)	−0.0041 (16)
C9	0.0280 (18)	0.029 (2)	0.0207 (17)	−0.0037 (15)	−0.0012 (14)	0.0010 (15)
C10	0.037 (2)	0.031 (2)	0.0284 (19)	−0.0037 (17)	−0.0062 (15)	−0.0091 (17)
C11	0.0308 (18)	0.031 (2)	0.0220 (17)	0.0019 (16)	0.0018 (14)	−0.0015 (16)
C12	0.0283 (18)	0.031 (2)	0.0164 (17)	−0.0006 (15)	−0.0049 (14)	−0.0026 (15)
C13	0.0251 (17)	0.024 (2)	0.0239 (17)	0.0047 (14)	−0.0016 (14)	0.0000 (15)
C14	0.0231 (17)	0.031 (2)	0.0250 (18)	−0.0010 (15)	−0.0005 (14)	−0.0027 (16)
C15	0.036 (2)	0.032 (2)	0.044 (2)	0.0046 (17)	0.0117 (18)	0.0017 (18)
C16	0.0322 (19)	0.029 (2)	0.0240 (18)	−0.0043 (16)	−0.0032 (15)	0.0000 (16)
C17	0.0296 (19)	0.030 (2)	0.0239 (18)	0.0047 (15)	−0.0020 (15)	−0.0021 (16)
C18	0.0225 (16)	0.030 (2)	0.0256 (17)	−0.0013 (15)	−0.0020 (14)	0.0000 (16)

S1—C3	1.799 (4)	C7—C8	1.384 (5)
S1—C1	1.836 (3)	C7—H7	0.9500
O1—C2	1.225 (4)	C8—C9	1.393 (5)
O2—C5	1.372 (4)	C8—H8	0.9500
O2—C10	1.433 (4)	C9—H9	0.9500
O3—C14	1.382 (4)	C10—H10A	0.9800
O3—C15	1.437 (4)	C10—H10B	0.9800
O4—C16	1.388 (4)	C10—H10C	0.9800
O4—C15	1.445 (4)	C11—C12	1.514 (5)
N1—C2	1.363 (4)	C11—H11A	0.9900
N1—C1	1.451 (4)	C11—H11B	0.9900
N1—C11	1.455 (4)	C12—C18	1.395 (5)
C1—C4	1.510 (5)	C12—C13	1.408 (5)
C1—H1	1.0000	C13—C14	1.372 (5)
C2—C3	1.501 (5)	C13—H13	0.9500
C3—H3A	0.9900	C14—C16	1.379 (5)
C3—H3B	0.9900	C15—H15A	0.9900
C4—C9	1.387 (5)	C15—H15B	0.9900
C4—C5	1.411 (4)	C16—C17	1.375 (5)
C5—C6	1.382 (5)	C17—C18	1.404 (5)
C6—C7	1.395 (5)	C17—H17	0.9500
C6—H6	0.9500	C18—H18	0.9500
C3—S1—C1	92.50 (15)	C4—C9—H9	119.7
C5—O2—C10	116.5 (3)	C8—C9—H9	119.7
C14—O3—C15	104.2 (2)	O2—C10—H10A	109.5
C16—O4—C15	103.5 (3)	O2—C10—H10B	109.5
C2—N1—C1	118.9 (3)	H10A—C10—H10B	109.5
C2—N1—C11	121.3 (3)	O2—C10—H10C	109.5
C1—N1—C11	119.1 (3)	H10A—C10—H10C	109.5
N1—C1—C4	114.1 (3)	H10B—C10—H10C	109.5
N1—C1—S1	105.6 (2)	N1—C11—C12	113.3 (3)
C4—C1—S1	112.2 (2)	N1—C11—H11A	108.9
N1—C1—H1	108.2	C12—C11—H11A	108.9
C4—C1—H1	108.2	N1—C11—H11B	108.9
S1—C1—H1	108.2	C12—C11—H11B	108.9
O1—C2—N1	123.9 (3)	H11A—C11—H11B	107.7
O1—C2—C3	124.3 (3)	C18—C12—C13	120.5 (3)
N1—C2—C3	111.8 (3)	C18—C12—C11	121.5 (3)
C2—C3—S1	108.0 (2)	C13—C12—C11	117.9 (3)
C2—C3—H3A	110.1	C14—C13—C12	116.4 (3)
S1—C3—H3A	110.1	C14—C13—H13	121.8
C2—C3—H3B	110.1	C12—C13—H13	121.8
S1—C3—H3B	110.1	C13—C14—C16	123.2 (3)
H3A—C3—H3B	108.4	C13—C14—O3	127.3 (3)
C9—C4—C5	119.0 (3)	C16—C14—O3	109.4 (3)
C9—C4—C1	123.5 (3)	O3—C15—O4	106.9 (3)
C5—C4—C1	117.5 (3)	O3—C15—H15A	110.3
O2—C5—C6	124.8 (3)	O4—C15—H15A	110.3
O2—C5—C4	114.9 (3)	O3—C15—H15B	110.3
C6—C5—C4	120.3 (3)	O4—C15—H15B	110.3
C5—C6—C7	119.8 (3)	H15A—C15—H15B	108.6
C5—C6—H6	120.1	C17—C16—C14	121.4 (3)
C7—C6—H6	120.1	C17—C16—O4	128.5 (3)
C8—C7—C6	120.4 (3)	C14—C16—O4	110.1 (3)
C8—C7—H7	119.8	C16—C17—C18	116.8 (3)
C6—C7—H7	119.8	C16—C17—H17	121.6
C7—C8—C9	119.8 (3)	C18—C17—H17	121.6
C7—C8—H8	120.1	C12—C18—C17	121.7 (3)
C9—C8—H8	120.1	C12—C18—H18	119.2
C4—C9—C8	120.7 (3)	C17—C18—H18	119.2
C2—N1—C1—C4	115.2 (3)	C5—C4—C9—C8	0.1 (5)
C11—N1—C1—C4	−74.1 (4)	C1—C4—C9—C8	−179.2 (3)
C2—N1—C1—S1	−8.5 (4)	C7—C8—C9—C4	−1.8 (5)
C11—N1—C1—S1	162.2 (2)	C2—N1—C11—C12	101.4 (4)
C3—S1—C1—N1	14.3 (2)	C1—N1—C11—C12	−69.0 (4)
C3—S1—C1—C4	−110.5 (3)	N1—C11—C12—C18	−33.1 (4)
C1—N1—C2—O1	175.9 (3)	N1—C11—C12—C13	149.5 (3)
C11—N1—C2—O1	5.4 (5)	C18—C12—C13—C14	−2.1 (5)
C1—N1—C2—C3	−4.0 (4)	C11—C12—C13—C14	175.3 (3)
C11—N1—C2—C3	−174.5 (3)	C12—C13—C14—C16	1.4 (5)
O1—C2—C3—S1	−165.0 (3)	C12—C13—C14—O3	179.1 (3)
N1—C2—C3—S1	14.9 (4)	C15—O3—C14—C13	166.6 (3)
C1—S1—C3—C2	−16.7 (3)	C15—O3—C14—C16	−15.4 (4)
N1—C1—C4—C9	−14.6 (4)	C14—O3—C15—O4	23.8 (4)
S1—C1—C4—C9	105.4 (3)	C16—O4—C15—O3	−23.0 (3)
N1—C1—C4—C5	166.0 (3)	C13—C14—C16—C17	0.9 (5)
S1—C1—C4—C5	−73.9 (3)	O3—C14—C16—C17	−177.2 (3)
C10—O2—C5—C6	−7.3 (4)	C13—C14—C16—O4	179.2 (3)
C10—O2—C5—C4	172.6 (3)	O3—C14—C16—O4	1.1 (4)
C9—C4—C5—O2	−178.2 (3)	C15—O4—C16—C17	−168.2 (3)
C1—C4—C5—O2	1.2 (4)	C15—O4—C16—C14	13.7 (4)
C9—C4—C5—C6	1.7 (4)	C14—C16—C17—C18	−2.3 (5)
C1—C4—C5—C6	−179.0 (3)	O4—C16—C17—C18	179.8 (3)
O2—C5—C6—C7	178.1 (3)	C13—C12—C18—C17	0.8 (5)
C4—C5—C6—C7	−1.8 (5)	C11—C12—C18—C17	−176.6 (3)
C5—C6—C7—C8	0.0 (5)	C16—C17—C18—C12	1.5 (5)
C6—C7—C8—C9	1.7 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1i	0.95	2.36	3.302 (4)	170
C13—H13···O1ii	0.95	2.43	3.352 (4)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O1i	0.95	2.36	3.302 (4)	170
C13—H13⋯O1ii	0.95	2.43	3.352 (4)	163

Symmetry codes: (i) ; (ii) .