Crystal structure of (±)-3-[(benzo[d][1,3]dioxol-5-yl)meth-yl]-2-(3,4,5-tri-meth-oxy-phen-yl)-1,3-thia-zolidin-4-one.

In the title thia-zolidine-4-one derivative, C20H21NO6S, the central thia-zolidine ring is essentially planar (r.m.s. deviation for all non-H atoms = 0.0287 Å) and forms a dihedral angle of 88.25 (5)° with the meth-oxy-substituted benzene ring and 74.21 (4)° with the 1,3-benzodioxole ring. The heterocyclic ring (with two O atoms) fused to benzene ring adopts an envelope conformation with the non-ring-junction C atom as the flap. In the crystal, the mol-ecules are linked into chains along [001] through weak C-H⋯O inter-actions, forming R (4) 4(28) edge-fused rings.

Related literature

For biological and pharmacological properties of thia­zolidin-4-one systems, see: Rojas et al. (2011 ▶); Jackson et al. (2007 ▶); Gududuru et al. (2004 ▶); Kunzler et al. (2013 ▶); Rawal et al. (2008 ▶); Barreca et al. (2002 ▶); Rawal et al. (2007 ▶); Cunico et al. (2007 ▶). For similar structures, see: Fun et al. (2011 ▶); Cunico et al. (2007 ▶). For the synthesis of heterocycles of synthetic and biological inter­est, see: Abonia et al. (2010 ▶); Abonia (2014 ▶); Moreno-Fuquen et al. (2014 ▶). For hydrogen bonding, see: Nardelli (1995 ▶). For hydrogen-bond graph-set motifs, see: Etter (1990 ▶).

Experimental

Crystal data

C20H21NO6S

M = 403.44

Monoclinic,

a = 15.3098 (11) Å

b = 14.3677 (12) Å

c = 8.6546 (3) Å

β = 97.429 (4)°

V = 1887.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 295 K

0.25 × 0.24 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer

6325 measured reflections

3845 independent reflections

2922 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.150

S = 1.03

3845 reflections

258 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.34 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681402340X/gg2142sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681402340X/gg2142Isup2.hkl

Click here for additional data file.

. DOI: 10.1107/S160053681402340X/gg2142fig1.tif

Mol­ecular conformation and atom numbering scheme for the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radius.

Click here for additional data file.

. DOI: 10.1107/S160053681402340X/gg2142fig2.tif

Part of the crystal structure of (I), forming one-dimensional chain, along [001]. Symmetry code: (i) −x+1,-y,-z+1; (ii) x,+y,+z-1.

Click here for additional data file.

. DOI: 10.1107/S160053681402340X/gg2142fig3.tif

The formation of the title compound.

CCDC reference: 1030709

Additional supporting information: crystallographic information; 3D view; checkCIF report

C20H21NO6S	F(000) = 848
Mr = 403.44	Dx = 1.420 Mg m−3
Monoclinic, P21/c	Melting point: 395(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.3098 (11) Å	Cell parameters from 4353 reflections
b = 14.3677 (12) Å	θ = 2.9–26.4°
c = 8.6546 (3) Å	µ = 0.21 mm−1
β = 97.429 (4)°	T = 295 K
V = 1887.7 (2) Å3	Block, white
Z = 4	0.25 × 0.24 × 0.12 mm

Nonius KappaCCD diffractometer	2922 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.018
Graphite monochromator	θmax = 26.4°, θmin = 2.9°
CCD rotation images, thick slices scans	h = −19→19
6325 measured reflections	k = −17→14
3845 independent reflections	l = −10→10

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.150	w = 1/[σ2(Fo2) + (0.0917P)2 + 0.3214P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3845 reflections	Δρmax = 0.34 e Å−3
258 parameters	Δρmin = −0.34 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.031 (5)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
S1	0.05694 (4)	0.24960 (4)	0.17750 (7)	0.0661 (2)
N1	0.14541 (10)	0.12826 (11)	0.03330 (17)	0.0446 (4)
O1	0.33492 (13)	−0.23628 (12)	0.3230 (2)	0.0820 (5)
O2	0.18594 (11)	−0.21212 (12)	0.26924 (19)	0.0699 (5)
O3	0.03899 (10)	0.05317 (10)	−0.12885 (15)	0.0544 (4)
O4	0.43425 (9)	0.18093 (12)	0.53026 (18)	0.0665 (4)
O5	0.36360 (10)	0.04832 (11)	0.69166 (16)	0.0633 (4)
O6	0.20130 (10)	−0.01846 (11)	0.59983 (16)	0.0611 (4)
C1	0.25404 (13)	−0.00145 (13)	0.0739 (2)	0.0465 (4)
C2	0.19505 (13)	−0.06376 (13)	0.1275 (2)	0.0471 (4)
H2	0.1345	−0.0546	0.1076	0.056*
C3	0.23005 (13)	−0.13912 (14)	0.2109 (2)	0.0496 (5)
C4	0.31919 (15)	−0.15342 (14)	0.2424 (2)	0.0569 (5)
C5	0.37858 (15)	−0.09274 (17)	0.1948 (3)	0.0681 (6)
H5	0.4390	−0.1018	0.2186	0.082*
C6	0.34390 (14)	−0.01630 (15)	0.1082 (3)	0.0597 (5)
H6	0.3824	0.0262	0.0723	0.072*
C7	0.2520 (2)	−0.2654 (2)	0.3556 (4)	0.0985 (10)
H7A	0.2483	−0.2583	0.4660	0.118*
H7B	0.2436	−0.3307	0.3291	0.118*
C8	0.21892 (14)	0.08075 (14)	−0.0244 (2)	0.0517 (5)
H8A	0.2663	0.1250	−0.0290	0.062*
H8B	0.2001	0.0593	−0.1297	0.062*
C9	0.06129 (12)	0.11079 (12)	−0.02699 (19)	0.0440 (4)
C10	−0.00378 (13)	0.16964 (15)	0.0466 (2)	0.0531 (5)
H10A	−0.0405	0.1304	0.1028	0.064*
H10B	−0.0415	0.2033	−0.0332	0.064*
C11	0.16404 (13)	0.19973 (13)	0.1526 (2)	0.0487 (4)
H11	0.1991 (14)	0.2490 (14)	0.116 (2)	0.047 (5)*
C12	0.21490 (13)	0.16198 (13)	0.3015 (2)	0.0455 (4)
C13	0.17821 (13)	0.09318 (14)	0.3864 (2)	0.0485 (4)
H13	0.1202	0.0744	0.3582	0.058*
C14	0.22882 (13)	0.05301 (14)	0.5134 (2)	0.0480 (4)
C15	0.31476 (13)	0.08397 (14)	0.5598 (2)	0.0494 (5)
C16	0.35014 (13)	0.15420 (14)	0.4761 (2)	0.0495 (5)
C17	0.30002 (13)	0.19268 (14)	0.3455 (2)	0.0485 (4)
H17	0.3238	0.2388	0.2882	0.058*
C18	0.47265 (17)	0.2509 (2)	0.4451 (4)	0.0809 (8)
H18A	0.5313	0.2637	0.4940	0.121*
H18B	0.4747	0.2298	0.3404	0.121*
H18C	0.4379	0.3066	0.4432	0.121*
C19	0.40464 (18)	−0.03832 (19)	0.6684 (3)	0.0789 (7)
H19A	0.4372	−0.0586	0.7648	0.118*
H19B	0.3604	−0.0837	0.6335	0.118*
H19C	0.4440	−0.0312	0.5914	0.118*
C20	0.11256 (16)	−0.0499 (2)	0.5620 (3)	0.0705 (6)
H20A	0.1015	−0.0999	0.6305	0.106*
H20B	0.0728	0.0005	0.5738	0.106*
H20C	0.1037	−0.0715	0.4561	0.106*

	U11	U22	U33	U12	U13	U23
S1	0.0659 (4)	0.0607 (4)	0.0668 (4)	0.0178 (3)	−0.0108 (3)	−0.0235 (3)
N1	0.0525 (9)	0.0384 (8)	0.0411 (7)	0.0034 (7)	−0.0006 (6)	−0.0032 (6)
O1	0.0796 (12)	0.0583 (10)	0.0997 (13)	0.0094 (9)	−0.0203 (10)	0.0197 (9)
O2	0.0717 (10)	0.0571 (9)	0.0785 (10)	−0.0042 (8)	0.0007 (8)	0.0229 (8)
O3	0.0715 (9)	0.0474 (8)	0.0423 (7)	−0.0078 (7)	−0.0001 (6)	−0.0040 (6)
O4	0.0510 (8)	0.0731 (11)	0.0703 (9)	−0.0093 (7)	−0.0115 (7)	0.0114 (8)
O5	0.0688 (10)	0.0676 (10)	0.0492 (8)	0.0066 (8)	−0.0093 (7)	0.0052 (7)
O6	0.0635 (9)	0.0663 (10)	0.0527 (8)	−0.0078 (7)	0.0049 (6)	0.0109 (7)
C1	0.0514 (10)	0.0423 (10)	0.0461 (9)	0.0034 (8)	0.0072 (8)	−0.0041 (8)
C2	0.0463 (10)	0.0450 (10)	0.0487 (10)	0.0017 (8)	0.0011 (8)	−0.0004 (8)
C3	0.0566 (11)	0.0443 (10)	0.0467 (10)	−0.0019 (8)	0.0017 (8)	−0.0024 (8)
C4	0.0622 (12)	0.0446 (11)	0.0594 (12)	0.0071 (10)	−0.0093 (9)	−0.0018 (9)
C5	0.0483 (11)	0.0590 (13)	0.0941 (17)	0.0082 (10)	−0.0015 (11)	−0.0036 (12)
C6	0.0500 (11)	0.0495 (12)	0.0808 (14)	−0.0006 (9)	0.0137 (10)	−0.0004 (10)
C7	0.095 (2)	0.087 (2)	0.108 (2)	−0.0009 (17)	−0.0095 (18)	0.0476 (18)
C8	0.0570 (11)	0.0478 (11)	0.0518 (10)	0.0038 (9)	0.0122 (9)	0.0026 (8)
C9	0.0565 (11)	0.0366 (9)	0.0374 (8)	−0.0016 (8)	0.0007 (7)	0.0038 (7)
C10	0.0548 (11)	0.0517 (12)	0.0510 (10)	0.0031 (9)	0.0003 (8)	−0.0020 (9)
C11	0.0564 (11)	0.0395 (10)	0.0473 (10)	−0.0005 (8)	−0.0039 (8)	−0.0045 (8)
C12	0.0525 (10)	0.0391 (9)	0.0429 (9)	0.0016 (8)	−0.0015 (7)	−0.0054 (7)
C13	0.0488 (10)	0.0489 (11)	0.0462 (10)	−0.0018 (9)	0.0002 (8)	−0.0050 (8)
C14	0.0567 (11)	0.0456 (10)	0.0415 (9)	−0.0009 (9)	0.0060 (8)	−0.0035 (8)
C15	0.0536 (11)	0.0511 (11)	0.0414 (9)	0.0053 (9)	−0.0019 (8)	−0.0024 (8)
C16	0.0472 (10)	0.0497 (11)	0.0495 (10)	0.0007 (8)	−0.0018 (8)	−0.0062 (8)
C17	0.0524 (10)	0.0452 (10)	0.0465 (10)	0.0003 (8)	0.0009 (8)	−0.0010 (8)
C18	0.0523 (13)	0.089 (2)	0.0960 (19)	−0.0172 (12)	−0.0103 (12)	0.0222 (15)
C19	0.0738 (16)	0.0671 (16)	0.0913 (18)	0.0130 (13)	−0.0061 (13)	0.0130 (14)
C20	0.0702 (14)	0.0772 (16)	0.0645 (13)	−0.0188 (13)	0.0107 (11)	0.0061 (12)

S1—C10	1.788 (2)	C7—H7A	0.9700
S1—C11	1.828 (2)	C7—H7B	0.9700
N1—C9	1.349 (2)	C8—H8A	0.9700
N1—C11	1.458 (2)	C8—H8B	0.9700
N1—C8	1.459 (2)	C9—C10	1.509 (3)
O1—C4	1.385 (3)	C10—H10A	0.9700
O1—C7	1.399 (4)	C10—H10B	0.9700
O2—C3	1.378 (2)	C11—C12	1.517 (3)
O2—C7	1.405 (3)	C11—H11	0.97 (2)
O3—C9	1.225 (2)	C12—C17	1.382 (3)
O4—C16	1.367 (2)	C12—C13	1.393 (3)
O4—C18	1.418 (3)	C13—C14	1.386 (3)
O5—C15	1.380 (2)	C13—H13	0.9300
O5—C19	1.420 (3)	C14—C15	1.398 (3)
O6—C14	1.369 (2)	C15—C16	1.392 (3)
O6—C20	1.429 (3)	C16—C17	1.396 (3)
C1—C6	1.386 (3)	C17—H17	0.9300
C1—C2	1.393 (3)	C18—H18A	0.9600
C1—C8	1.513 (3)	C18—H18B	0.9600
C2—C3	1.371 (3)	C18—H18C	0.9600
C2—H2	0.9300	C19—H19A	0.9600
C3—C4	1.372 (3)	C19—H19B	0.9600
C4—C5	1.361 (3)	C19—H19C	0.9600
C5—C6	1.395 (3)	C20—H20A	0.9600
C5—H5	0.9300	C20—H20B	0.9600
C6—H6	0.9300	C20—H20C	0.9600
C10—S1—C11	94.26 (9)	C9—C10—H10B	110.1
C9—N1—C11	119.64 (16)	S1—C10—H10B	110.1
C9—N1—C8	121.38 (16)	H10A—C10—H10B	108.4
C11—N1—C8	118.90 (16)	N1—C11—C12	112.43 (15)
C4—O1—C7	104.81 (19)	N1—C11—S1	105.27 (13)
C3—O2—C7	104.86 (19)	C12—C11—S1	114.18 (14)
C16—O4—C18	117.14 (16)	N1—C11—H11	110.3 (12)
C15—O5—C19	114.25 (18)	C12—C11—H11	107.3 (13)
C14—O6—C20	117.56 (17)	S1—C11—H11	107.2 (12)
C6—C1—C2	119.85 (18)	C17—C12—C13	120.77 (17)
C6—C1—C8	120.77 (18)	C17—C12—C11	118.81 (17)
C2—C1—C8	119.37 (17)	C13—C12—C11	120.29 (17)
C3—C2—C1	117.18 (18)	C14—C13—C12	119.46 (18)
C3—C2—H2	121.4	C14—C13—H13	120.3
C1—C2—H2	121.4	C12—C13—H13	120.3
C2—C3—C4	122.25 (19)	O6—C14—C13	124.46 (18)
C2—C3—O2	128.10 (19)	O6—C14—C15	115.25 (17)
C4—C3—O2	109.59 (18)	C13—C14—C15	120.28 (18)
C5—C4—C3	122.0 (2)	O5—C15—C16	119.59 (18)
C5—C4—O1	128.6 (2)	O5—C15—C14	120.59 (18)
C3—C4—O1	109.4 (2)	C16—C15—C14	119.76 (17)
C4—C5—C6	116.4 (2)	O4—C16—C15	115.97 (17)
C4—C5—H5	121.8	O4—C16—C17	124.14 (19)
C6—C5—H5	121.8	C15—C16—C17	119.89 (18)
C1—C6—C5	122.3 (2)	C12—C17—C16	119.78 (18)
C1—C6—H6	118.8	C12—C17—H17	120.1
C5—C6—H6	118.8	C16—C17—H17	120.1
O1—C7—O2	109.8 (2)	O4—C18—H18A	109.5
O1—C7—H7A	109.7	O4—C18—H18B	109.5
O2—C7—H7A	109.7	H18A—C18—H18B	109.5
O1—C7—H7B	109.7	O4—C18—H18C	109.5
O2—C7—H7B	109.7	H18A—C18—H18C	109.5
H7A—C7—H7B	108.2	H18B—C18—H18C	109.5
N1—C8—C1	113.99 (15)	O5—C19—H19A	109.5
N1—C8—H8A	108.8	O5—C19—H19B	109.5
C1—C8—H8A	108.8	H19A—C19—H19B	109.5
N1—C8—H8B	108.8	O5—C19—H19C	109.5
C1—C8—H8B	108.8	H19A—C19—H19C	109.5
H8A—C8—H8B	107.6	H19B—C19—H19C	109.5
O3—C9—N1	124.56 (18)	O6—C20—H20A	109.5
O3—C9—C10	122.99 (18)	O6—C20—H20B	109.5
N1—C9—C10	112.44 (15)	H20A—C20—H20B	109.5
C9—C10—S1	108.06 (14)	O6—C20—H20C	109.5
C9—C10—H10A	110.1	H20A—C20—H20C	109.5
S1—C10—H10A	110.1	H20B—C20—H20C	109.5
C6—C1—C2—C3	−1.2 (3)	C8—N1—C11—C12	−60.8 (2)
C8—C1—C2—C3	177.50 (16)	C9—N1—C11—S1	−2.3 (2)
C1—C2—C3—C4	0.4 (3)	C8—N1—C11—S1	174.29 (13)
C1—C2—C3—O2	−176.52 (18)	C10—S1—C11—N1	4.45 (14)
C7—O2—C3—C2	−175.1 (2)	C10—S1—C11—C12	−119.35 (15)
C7—O2—C3—C4	7.6 (3)	N1—C11—C12—C17	113.8 (2)
C2—C3—C4—C5	1.1 (3)	S1—C11—C12—C17	−126.32 (17)
O2—C3—C4—C5	178.6 (2)	N1—C11—C12—C13	−62.1 (2)
C2—C3—C4—O1	−177.80 (18)	S1—C11—C12—C13	57.8 (2)
O2—C3—C4—O1	−0.3 (2)	C17—C12—C13—C14	−2.2 (3)
C7—O1—C4—C5	174.1 (3)	C11—C12—C13—C14	173.64 (17)
C7—O1—C4—C3	−7.1 (3)	C20—O6—C14—C13	−3.9 (3)
C3—C4—C5—C6	−1.8 (3)	C20—O6—C14—C15	177.17 (19)
O1—C4—C5—C6	176.9 (2)	C12—C13—C14—O6	−176.27 (17)
C2—C1—C6—C5	0.5 (3)	C12—C13—C14—C15	2.7 (3)
C8—C1—C6—C5	−178.2 (2)	C19—O5—C15—C16	−100.9 (2)
C4—C5—C6—C1	0.9 (3)	C19—O5—C15—C14	81.9 (2)
C4—O1—C7—O2	12.0 (3)	O6—C14—C15—O5	−5.0 (3)
C3—O2—C7—O1	−12.2 (3)	C13—C14—C15—O5	175.98 (17)
C9—N1—C8—C1	−98.3 (2)	O6—C14—C15—C16	177.76 (17)
C11—N1—C8—C1	85.2 (2)	C13—C14—C15—C16	−1.3 (3)
C6—C1—C8—N1	−137.52 (19)	C18—O4—C16—C15	178.6 (2)
C2—C1—C8—N1	43.8 (2)	C18—O4—C16—C17	−1.4 (3)
C11—N1—C9—O3	178.98 (17)	O5—C15—C16—O4	2.1 (3)
C8—N1—C9—O3	2.5 (3)	C14—C15—C16—O4	179.39 (18)
C11—N1—C9—C10	−1.8 (2)	O5—C15—C16—C17	−177.93 (17)
C8—N1—C9—C10	−178.28 (16)	C14—C15—C16—C17	−0.7 (3)
O3—C9—C10—S1	−175.68 (14)	C13—C12—C17—C16	0.3 (3)
N1—C9—C10—S1	5.1 (2)	C11—C12—C17—C16	−175.61 (17)
C11—S1—C10—C9	−5.43 (15)	O4—C16—C17—C12	−178.89 (18)
C9—N1—C11—C12	122.59 (18)	C15—C16—C17—C12	1.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···O1i	0.96	2.45	3.350 (3)	155
C8—H8B···O6ii	0.97	2.60	3.529 (2)	161

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C18H18AO1i	0.96	2.45	3.350(3)	155
C8H8BO6ii	0.97	2.60	3.529(2)	161

Symmetry codes: (i) ; (ii) .