Methyl (2E)-2-[(2,4-dioxo-1,3-thia-zolidin-3-yl)meth-yl]-3-phenyl-prop-2-enoate.

In the title compound, C(14)H(13)NO(4)S, the thia-zolidine ring is essentially planar [maximum deviation = 0.010 (2) Å for the carbonyl C atom between the N and S atoms] and is oriented at a dihedral angle of 60.1 (1)° with respect to the benzene ring. In the crystal, mol-ecules are linked into zigzag chains running along the c axis by C-H⋯O hydrogen bonds. The crystal packing is further stabilized by C-H⋯π inter-actions involving the benzene ring.

Related literature

For the biological activity of thia­zolidine derivatives, see: Chen et al. (2000 ▶); Jacop & Kutty (2004 ▶); Kalia et al. (2007 ▶); Vicentini et al. (1998 ▶); Vigorita et al. (1992 ▶). For resonance effects of n class="Chemical">acrylate, see: Merlino (1971 ▶); Varghese et al. (1986 ▶). For closely related structures, see: Fun et al. (2009 ▶); Vijayakumar et al. (2012 ▶).

Experimental

Crystal data

C14H13NO4S

M = 291.31

Orthorhombic,

a = 11.9274 (3) Å

b = 15.6064 (6) Å

c = 7.2949 (3) Å

V = 1357.90 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 293 K

0.26 × 0.22 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.937, T max = 0.956

13845 measured reflections

2948 independent reflections

2576 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.082

S = 1.03

2948 reflections

182 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶), 1348 Friedel pairs

Flack parameter: 0.01 (7)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: n class="Gene">APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia (1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812000578/bt5778sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000578/bt5778Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812000578/bt5778Isup3.cml

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

C14H13NO4S	F(000) = 608
Mr = 291.31	Dx = 1.425 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2955 reflections
a = 11.9274 (3) Å	θ = 1.3–26.9°
b = 15.6064 (6) Å	µ = 0.25 mm−1
c = 7.2949 (3) Å	T = 293 K
V = 1357.90 (8) Å3	Block, colourless
Z = 4	0.26 × 0.22 × 0.18 mm

Bruker APEXII CCD diffractometer	2948 independent reflections
Radiation source: fine-focus sealed tube	2576 reflections with I > 2σ(I)
graphite	Rint = 0.026
Detector resolution: 10.0 pixels mm-1	θmax = 27.0°, θmin = 2.2°
ω scans	h = −9→15
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −19→19
Tmin = 0.937, Tmax = 0.956	l = −9→9
13845 measured reflections

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)] = 0.030	H-atom parameters constrained
wR(F2) = 0.082	w = 1/[σ2(Fo2) + (0.0474P)2 + 0.0813P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
2948 reflections	Δρmax = 0.12 e Å−3
182 parameters	Δρmin = −0.22 e Å−3
1 restraint	Absolute structure: Flack (1983), 1348 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (7)

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 > 2sigma(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	0.88283 (12)	0.42078 (11)	0.3591 (3)	0.0453 (4)
C2	0.88406 (18)	0.46494 (13)	0.1782 (3)	0.0656 (6)
H2A	0.9463	0.5049	0.1725	0.079*
H2B	0.8150	0.4967	0.1609	0.079*
C3	0.89926 (13)	0.30148 (13)	0.1635 (3)	0.0476 (4)
C4	0.90014 (12)	0.27637 (10)	0.4973 (3)	0.0414 (3)
H4A	0.8444	0.2315	0.4854	0.050*
H4B	0.8827	0.3088	0.6071	0.050*
C5	1.01448 (11)	0.23548 (9)	0.5200 (2)	0.0358 (3)
C6	1.02982 (13)	0.15517 (9)	0.5761 (2)	0.0371 (3)
H6	1.1043	0.1377	0.5805	0.044*
C7	0.94821 (12)	0.08968 (10)	0.6322 (2)	0.0351 (3)
C8	0.84781 (14)	0.10827 (10)	0.7234 (2)	0.0415 (4)
H8	0.8296	0.1648	0.7508	0.050*
C9	0.77608 (14)	0.04342 (11)	0.7725 (2)	0.0474 (4)
H9	0.7092	0.0564	0.8319	0.057*
C10	0.80204 (15)	−0.04058 (11)	0.7348 (3)	0.0501 (4)
H10	0.7525	−0.0840	0.7672	0.060*
C11	0.90151 (15)	−0.06013 (11)	0.6491 (3)	0.0492 (4)
H11	0.9195	−0.1170	0.6246	0.059*
C12	0.97448 (14)	0.00418 (10)	0.5993 (2)	0.0421 (4)
H12	1.0421	−0.0097	0.5431	0.050*
C13	1.11324 (12)	0.29123 (10)	0.4825 (2)	0.0396 (3)
C14	1.31055 (14)	0.30026 (12)	0.4659 (3)	0.0592 (5)
H14A	1.3018	0.3385	0.3638	0.089*
H14B	1.3737	0.2634	0.4448	0.089*
H14C	1.3228	0.3330	0.5756	0.089*
N1	0.89204 (9)	0.33305 (8)	0.3393 (2)	0.0387 (3)
O1	0.87429 (10)	0.45658 (8)	0.5042 (2)	0.0606 (3)
O2	0.90570 (11)	0.22625 (10)	0.1267 (2)	0.0704 (4)
O3	1.10784 (9)	0.36635 (7)	0.4537 (2)	0.0627 (4)
O4	1.21042 (8)	0.24908 (7)	0.4864 (2)	0.0562 (3)
S1	0.89843 (4)	0.38495 (4)	0.00251 (8)	0.07068 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0282 (7)	0.0397 (8)	0.0680 (12)	−0.0004 (6)	−0.0036 (8)	0.0022 (9)
C2	0.0571 (11)	0.0562 (12)	0.0834 (16)	−0.0031 (9)	−0.0105 (10)	0.0271 (11)
C3	0.0327 (8)	0.0616 (11)	0.0484 (10)	0.0003 (7)	−0.0045 (7)	−0.0026 (9)
C4	0.0379 (8)	0.0397 (8)	0.0467 (9)	0.0014 (6)	0.0036 (7)	0.0044 (8)
C5	0.0328 (7)	0.0388 (7)	0.0359 (7)	−0.0008 (5)	−0.0004 (6)	−0.0030 (6)
C6	0.0333 (7)	0.0420 (8)	0.0360 (7)	0.0000 (6)	−0.0017 (6)	−0.0004 (6)
C7	0.0354 (7)	0.0388 (8)	0.0312 (7)	0.0002 (6)	−0.0038 (6)	0.0016 (6)
C8	0.0456 (9)	0.0414 (8)	0.0376 (8)	0.0038 (6)	0.0035 (7)	0.0025 (7)
C9	0.0416 (9)	0.0605 (10)	0.0401 (9)	−0.0026 (7)	0.0059 (8)	0.0073 (7)
C10	0.0526 (9)	0.0543 (10)	0.0434 (9)	−0.0163 (8)	−0.0092 (8)	0.0097 (8)
C11	0.0621 (11)	0.0373 (8)	0.0482 (10)	−0.0015 (7)	−0.0080 (9)	0.0020 (7)
C12	0.0442 (9)	0.0401 (8)	0.0419 (9)	0.0055 (7)	−0.0023 (7)	0.0022 (7)
C13	0.0374 (7)	0.0409 (8)	0.0405 (8)	−0.0027 (6)	−0.0025 (7)	−0.0052 (7)
C14	0.0339 (8)	0.0728 (11)	0.0709 (14)	−0.0108 (8)	0.0018 (9)	0.0034 (11)
N1	0.0350 (6)	0.0353 (7)	0.0457 (8)	−0.0001 (5)	−0.0021 (6)	0.0020 (6)
O1	0.0543 (7)	0.0463 (7)	0.0811 (10)	0.0042 (5)	−0.0015 (8)	−0.0153 (8)
O2	0.0777 (10)	0.0645 (9)	0.0690 (10)	0.0068 (7)	−0.0084 (8)	−0.0233 (8)
O3	0.0443 (7)	0.0381 (6)	0.1056 (13)	−0.0058 (5)	0.0005 (7)	0.0012 (7)
O4	0.0319 (5)	0.0495 (6)	0.0873 (9)	−0.0023 (4)	0.0024 (6)	0.0087 (7)
S1	0.0586 (3)	0.1007 (4)	0.0527 (3)	0.0051 (2)	−0.0039 (3)	0.0233 (3)

C1—O1	1.202 (3)	C7—C12	1.392 (2)
C1—N1	1.381 (2)	C7—C8	1.400 (2)
C1—C2	1.489 (3)	C8—C9	1.373 (2)
C2—S1	1.797 (3)	C8—H8	0.9300
C2—H2A	0.9700	C9—C10	1.375 (2)
C2—H2B	0.9700	C9—H9	0.9300
C3—O2	1.207 (2)	C10—C11	1.375 (3)
C3—N1	1.376 (2)	C10—H10	0.9300
C3—S1	1.754 (2)	C11—C12	1.377 (3)
C4—N1	1.456 (2)	C11—H11	0.9300
C4—C5	1.515 (2)	C12—H12	0.9300
C4—H4A	0.9700	C13—O3	1.1928 (19)
C4—H4B	0.9700	C13—O4	1.3330 (18)
C5—C6	1.331 (2)	C14—O4	1.4445 (18)
C5—C13	1.490 (2)	C14—H14A	0.9600
C6—C7	1.470 (2)	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600
O1—C1—N1	124.04 (18)	C9—C8—H8	119.9
O1—C1—C2	124.52 (16)	C7—C8—H8	119.9
N1—C1—C2	111.44 (18)	C8—C9—C10	120.69 (16)
C1—C2—S1	108.14 (13)	C8—C9—H9	119.7
C1—C2—H2A	110.1	C10—C9—H9	119.7
S1—C2—H2A	110.1	C9—C10—C11	119.78 (15)
C1—C2—H2B	110.1	C9—C10—H10	120.1
S1—C2—H2B	110.1	C11—C10—H10	120.1
H2A—C2—H2B	108.4	C10—C11—C12	120.23 (16)
O2—C3—N1	124.05 (18)	C10—C11—H11	119.9
O2—C3—S1	124.99 (16)	C12—C11—H11	119.9
N1—C3—S1	110.95 (14)	C11—C12—C7	120.73 (16)
N1—C4—C5	113.71 (13)	C11—C12—H12	119.6
N1—C4—H4A	108.8	C7—C12—H12	119.6
C5—C4—H4A	108.8	O3—C13—O4	122.40 (13)
N1—C4—H4B	108.8	O3—C13—C5	124.31 (13)
C5—C4—H4B	108.8	O4—C13—C5	113.29 (13)
H4A—C4—H4B	107.7	O4—C14—H14A	109.5
C6—C5—C13	119.85 (13)	O4—C14—H14B	109.5
C6—C5—C4	123.64 (13)	H14A—C14—H14B	109.5
C13—C5—C4	116.47 (12)	O4—C14—H14C	109.5
C5—C6—C7	130.50 (15)	H14A—C14—H14C	109.5
C5—C6—H6	114.8	H14B—C14—H14C	109.5
C7—C6—H6	114.8	C3—N1—C1	117.22 (16)
C12—C7—C8	118.24 (14)	C3—N1—C4	121.05 (13)
C12—C7—C6	118.01 (14)	C1—N1—C4	121.65 (16)
C8—C7—C6	123.69 (14)	C13—O4—C14	116.35 (12)
C9—C8—C7	120.28 (15)	C3—S1—C2	92.23 (10)
O1—C1—C2—S1	179.94 (13)	C6—C5—C13—O4	8.7 (2)
N1—C1—C2—S1	−0.45 (17)	C4—C5—C13—O4	−173.45 (16)
N1—C4—C5—C6	−142.14 (16)	O2—C3—N1—C1	−178.70 (15)
N1—C4—C5—C13	40.1 (2)	S1—C3—N1—C1	1.56 (16)
C13—C5—C6—C7	175.87 (15)	O2—C3—N1—C4	4.6 (2)
C4—C5—C6—C7	−1.8 (3)	S1—C3—N1—C4	−175.10 (10)
C5—C6—C7—C12	149.04 (17)	O1—C1—N1—C3	178.90 (14)
C5—C6—C7—C8	−33.6 (3)	C2—C1—N1—C3	−0.71 (18)
C12—C7—C8—C9	−2.2 (2)	O1—C1—N1—C4	−4.5 (2)
C6—C7—C8—C9	−179.56 (15)	C2—C1—N1—C4	175.93 (14)
C7—C8—C9—C10	0.7 (3)	C5—C4—N1—C3	66.50 (18)
C8—C9—C10—C11	0.8 (3)	C5—C4—N1—C1	−110.01 (16)
C9—C10—C11—C12	−0.7 (3)	O3—C13—O4—C14	4.0 (3)
C10—C11—C12—C7	−1.0 (3)	C5—C13—O4—C14	−175.17 (15)
C8—C7—C12—C11	2.4 (2)	O2—C3—S1—C2	178.77 (16)
C6—C7—C12—C11	179.87 (15)	N1—C3—S1—C2	−1.50 (13)
C6—C5—C13—O3	−170.43 (18)	C1—C2—S1—C3	1.09 (14)
C4—C5—C13—O3	7.4 (3)

Cg is the centroid of the C7–C12 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1i	0.97	2.54	3.379 (2)	145.
C9—H9···Cgii	0.93	2.81	3.522 (2)	134.
C12—H12···Cgiii	0.93	2.80	3.541 (2)	137.

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C7–C12 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O1i	0.97	2.54	3.379 (2)	145
C9—H9⋯Cgii	0.93	2.81	3.522 (2)	134
C12—H12⋯Cgiii	0.93	2.80	3.541 (2)	137

Symmetry codes: (i) ; (ii) ; (iii) .