Methyl (Z)-2-[(2,4-dioxothia-zolidin-3-yl)meth-yl]-3-(2-methyl-phen-yl)prop-2-enoate.

The C=C bond in the title compound, C(15)H(15)NO(4)S, has a Z configuration. The thia-zolidine ring is essentially planar [maximum deviation = 0.008 (1) Å for the N atom] and is oriented at a dihedral angle of 59.1 (1)° with respect to the benzene ring. In the crystal, pairs of C-H⋯O hydrogen bonds link centrosymmetrically related mol-ecules into dimers, generating R(2) (2)(18) ring motifs. The crystal packing is further stabilized by C-H⋯π and C-O⋯π [O⋯centroid = 3.412 (2) Å and C-O⋯centroid = 115.0 (1)°] inter-actions.

Related literature

For the biolgical 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 ▶); Vennila et al. (2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H15NO4S

M = 305.34

Monoclinic,

a = 21.3744 (10) Å

b = 6.9762 (3) Å

c = 20.3084 (10) Å

β = 103.361 (2)°

V = 2946.3 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.23 mm−1

T = 293 K

0.26 × 0.23 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.941, T max = 0.959

18757 measured reflections

4354 independent reflections

2966 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.135

S = 1.04

4354 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: 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/S1600536811053682/bt5747sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811053682/bt5747Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811053682/bt5747Isup3.cml

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

C15H15NO4S	F(000) = 1280
Mr = 305.34	Dx = 1.377 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4370 reflections
a = 21.3744 (10) Å	θ = 2.0–30.2°
b = 6.9762 (3) Å	µ = 0.23 mm−1
c = 20.3084 (10) Å	T = 293 K
β = 103.361 (2)°	Block, colourless
V = 2946.3 (2) Å3	0.26 × 0.23 × 0.18 mm
Z = 8

Bruker APEXII CCD diffractometer	4354 independent reflections
Radiation source: fine-focus sealed tube	2966 reflections with I > 2σ(I)
graphite	Rint = 0.027
Detector resolution: 10.0 pixels mm-1	θmax = 30.2°, θmin = 2.0°
ω scans	h = −29→30
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −9→8
Tmin = 0.941, Tmax = 0.959	l = −28→18
18757 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0612P)2 + 1.2153P] where P = (Fo2 + 2Fc2)/3
4354 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

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
S1	0.34666 (2)	0.81404 (9)	0.02048 (3)	0.06438 (17)
N1	0.46454 (5)	0.81887 (16)	0.09106 (6)	0.0362 (3)
C4	0.51881 (7)	0.82904 (19)	0.14998 (8)	0.0383 (3)
H4A	0.5026	0.8529	0.1901	0.046*
H4B	0.5460	0.9364	0.1444	0.046*
C3	0.40174 (7)	0.8361 (2)	0.09848 (9)	0.0414 (3)
O4	0.46444 (5)	0.48419 (16)	0.16471 (7)	0.0588 (3)
C6	0.62202 (7)	0.6461 (2)	0.16616 (8)	0.0414 (3)
H6	0.6416	0.5262	0.1714	0.050*
C7	0.66451 (6)	0.8118 (2)	0.16498 (7)	0.0387 (3)
O2	0.38694 (6)	0.86509 (19)	0.15080 (7)	0.0583 (3)
C8	0.66505 (7)	0.9661 (2)	0.20808 (8)	0.0435 (3)
H8	0.6368	0.9677	0.2367	0.052*
O3	0.55140 (6)	0.30807 (16)	0.16562 (8)	0.0638 (4)
C13	0.52619 (7)	0.4616 (2)	0.16372 (8)	0.0432 (3)
C5	0.55872 (7)	0.64927 (19)	0.16051 (7)	0.0378 (3)
C1	0.47255 (8)	0.7930 (2)	0.02682 (8)	0.0473 (4)
O1	0.52437 (6)	0.7789 (2)	0.01315 (7)	0.0677 (4)
C12	0.70731 (7)	0.8089 (2)	0.12198 (9)	0.0463 (4)
C11	0.74813 (8)	0.9646 (3)	0.12352 (9)	0.0542 (4)
H11	0.7760	0.9662	0.0945	0.065*
C9	0.70709 (8)	1.1182 (3)	0.20911 (9)	0.0522 (4)
H9	0.7072	1.2207	0.2384	0.063*
C10	0.74848 (8)	1.1161 (3)	0.16660 (10)	0.0563 (4)
H10	0.7768	1.2176	0.1670	0.068*
C2	0.40897 (9)	0.7833 (4)	−0.02463 (9)	0.0668 (6)
H2A	0.4044	0.6605	−0.0476	0.080*
H2B	0.4066	0.8838	−0.0581	0.080*
C14	0.42702 (10)	0.3104 (3)	0.16151 (13)	0.0740 (6)
H14A	0.4213	0.2544	0.1173	0.111*
H14B	0.3858	0.3400	0.1701	0.111*
H14C	0.4491	0.2214	0.1949	0.111*
C15	0.70806 (12)	0.6449 (3)	0.07429 (13)	0.0782 (7)
H15A	0.6691	0.6460	0.0394	0.117*
H15B	0.7112	0.5262	0.0987	0.117*
H15C	0.7443	0.6578	0.0542	0.117*

	U11	U22	U33	U12	U13	U23
S1	0.0359 (2)	0.0934 (4)	0.0619 (3)	−0.0073 (2)	0.00745 (19)	−0.0024 (3)
N1	0.0322 (6)	0.0367 (6)	0.0412 (6)	−0.0031 (4)	0.0117 (5)	0.0009 (5)
C4	0.0378 (7)	0.0337 (7)	0.0434 (8)	−0.0037 (5)	0.0092 (6)	−0.0015 (6)
C3	0.0367 (7)	0.0370 (7)	0.0537 (9)	−0.0041 (6)	0.0171 (6)	−0.0012 (7)
O4	0.0437 (6)	0.0390 (6)	0.0968 (10)	−0.0075 (5)	0.0228 (6)	0.0094 (6)
C6	0.0419 (8)	0.0363 (7)	0.0463 (8)	0.0011 (6)	0.0110 (6)	0.0068 (6)
C7	0.0307 (6)	0.0412 (7)	0.0425 (7)	0.0006 (5)	0.0049 (5)	0.0076 (6)
O2	0.0509 (7)	0.0672 (8)	0.0649 (8)	−0.0050 (6)	0.0300 (6)	−0.0141 (6)
C8	0.0352 (7)	0.0517 (9)	0.0421 (8)	−0.0012 (6)	0.0057 (6)	0.0007 (7)
O3	0.0621 (8)	0.0351 (6)	0.0998 (11)	0.0017 (5)	0.0304 (7)	0.0084 (6)
C13	0.0463 (8)	0.0347 (7)	0.0505 (9)	−0.0031 (6)	0.0150 (7)	0.0036 (7)
C5	0.0394 (7)	0.0338 (7)	0.0413 (7)	−0.0034 (5)	0.0114 (6)	0.0031 (6)
C1	0.0422 (8)	0.0594 (10)	0.0431 (8)	−0.0062 (7)	0.0154 (6)	0.0020 (8)
O1	0.0476 (7)	0.1061 (11)	0.0566 (7)	−0.0012 (7)	0.0266 (6)	0.0016 (8)
C12	0.0402 (8)	0.0503 (9)	0.0498 (9)	−0.0006 (6)	0.0135 (6)	0.0031 (7)
C11	0.0370 (8)	0.0683 (11)	0.0586 (10)	−0.0074 (7)	0.0141 (7)	0.0107 (9)
C9	0.0434 (8)	0.0533 (9)	0.0537 (10)	−0.0066 (7)	−0.0016 (7)	−0.0059 (8)
C10	0.0410 (9)	0.0574 (10)	0.0656 (11)	−0.0153 (7)	0.0025 (8)	0.0059 (9)
C2	0.0475 (10)	0.1065 (16)	0.0468 (9)	−0.0154 (10)	0.0116 (8)	−0.0008 (10)
C14	0.0562 (11)	0.0524 (10)	0.1121 (18)	−0.0215 (9)	0.0171 (11)	0.0127 (11)
C15	0.0886 (16)	0.0700 (13)	0.0914 (16)	−0.0096 (11)	0.0524 (13)	−0.0158 (12)

S1—C3	1.7485 (17)	C13—C5	1.4911 (19)
S1—C2	1.7953 (19)	C1—O1	1.2064 (19)
N1—C1	1.3665 (19)	C1—C2	1.512 (2)
N1—C3	1.3901 (18)	C12—C11	1.389 (2)
N1—C4	1.4631 (18)	C12—C15	1.501 (3)
C4—C5	1.504 (2)	C11—C10	1.371 (3)
C4—H4A	0.9700	C11—H11	0.9300
C4—H4B	0.9700	C9—C10	1.371 (3)
C3—O2	1.1939 (19)	C9—H9	0.9300
O4—C13	1.3342 (18)	C10—H10	0.9300
O4—C14	1.4457 (19)	C2—H2A	0.9700
C6—C5	1.331 (2)	C2—H2B	0.9700
C6—C7	1.474 (2)	C14—H14A	0.9600
C6—H6	0.9300	C14—H14B	0.9600
C7—C8	1.386 (2)	C14—H14C	0.9600
C7—C12	1.403 (2)	C15—H15A	0.9600
C8—C9	1.387 (2)	C15—H15B	0.9600
C8—H8	0.9300	C15—H15C	0.9600
O3—C13	1.1953 (18)
C3—S1—C2	92.82 (8)	N1—C1—C2	112.00 (13)
C1—N1—C3	116.89 (13)	C11—C12—C7	118.10 (16)
C1—N1—C4	122.45 (12)	C11—C12—C15	120.67 (16)
C3—N1—C4	120.67 (12)	C7—C12—C15	121.21 (15)
N1—C4—C5	113.10 (12)	C10—C11—C12	121.87 (16)
N1—C4—H4A	109.0	C10—C11—H11	119.1
C5—C4—H4A	109.0	C12—C11—H11	119.1
N1—C4—H4B	109.0	C10—C9—C8	119.50 (16)
C5—C4—H4B	109.0	C10—C9—H9	120.3
H4A—C4—H4B	107.8	C8—C9—H9	120.3
O2—C3—N1	124.91 (15)	C11—C10—C9	120.04 (15)
O2—C3—S1	124.04 (12)	C11—C10—H10	120.0
N1—C3—S1	111.04 (11)	C9—C10—H10	120.0
C13—O4—C14	116.05 (14)	C1—C2—S1	107.24 (12)
C5—C6—C7	127.12 (13)	C1—C2—H2A	110.3
C5—C6—H6	116.4	S1—C2—H2A	110.3
C7—C6—H6	116.4	C1—C2—H2B	110.3
C8—C7—C12	119.52 (14)	S1—C2—H2B	110.3
C8—C7—C6	120.94 (14)	H2A—C2—H2B	108.5
C12—C7—C6	119.46 (14)	O4—C14—H14A	109.5
C7—C8—C9	120.95 (15)	O4—C14—H14B	109.5
C7—C8—H8	119.5	H14A—C14—H14B	109.5
C9—C8—H8	119.5	O4—C14—H14C	109.5
O3—C13—O4	123.06 (14)	H14A—C14—H14C	109.5
O3—C13—C5	125.24 (14)	H14B—C14—H14C	109.5
O4—C13—C5	111.70 (12)	C12—C15—H15A	109.5
C6—C5—C13	117.15 (13)	C12—C15—H15B	109.5
C6—C5—C4	123.91 (13)	H15A—C15—H15B	109.5
C13—C5—C4	118.92 (12)	C12—C15—H15C	109.5
O1—C1—N1	123.70 (15)	H15A—C15—H15C	109.5
O1—C1—C2	124.30 (15)	H15B—C15—H15C	109.5
C1—N1—C4—C5	−60.93 (18)	O4—C13—C5—C4	−7.7 (2)
C3—N1—C4—C5	119.28 (14)	N1—C4—C5—C6	125.99 (15)
C1—N1—C3—O2	−177.60 (15)	N1—C4—C5—C13	−52.85 (18)
C4—N1—C3—O2	2.2 (2)	C3—N1—C1—O1	178.80 (16)
C1—N1—C3—S1	1.36 (16)	C4—N1—C1—O1	−1.0 (2)
C4—N1—C3—S1	−178.84 (10)	C3—N1—C1—C2	−1.4 (2)
C2—S1—C3—O2	178.29 (16)	C4—N1—C1—C2	178.78 (15)
C2—S1—C3—N1	−0.68 (13)	C8—C7—C12—C11	−1.2 (2)
C5—C6—C7—C8	53.3 (2)	C6—C7—C12—C11	−178.06 (14)
C5—C6—C7—C12	−129.92 (17)	C8—C7—C12—C15	−179.69 (17)
C12—C7—C8—C9	0.3 (2)	C6—C7—C12—C15	3.5 (2)
C6—C7—C8—C9	177.09 (14)	C7—C12—C11—C10	1.6 (3)
C14—O4—C13—O3	−5.9 (3)	C15—C12—C11—C10	−179.94 (19)
C14—O4—C13—C5	174.51 (16)	C7—C8—C9—C10	0.3 (2)
C7—C6—C5—C13	−179.58 (15)	C12—C11—C10—C9	−1.0 (3)
C7—C6—C5—C4	1.6 (3)	C8—C9—C10—C11	0.0 (3)
O3—C13—C5—C6	−6.2 (3)	O1—C1—C2—S1	−179.42 (16)
O4—C13—C5—C6	173.39 (14)	N1—C1—C2—S1	0.8 (2)
O3—C13—C5—C4	172.74 (17)	C3—S1—C2—C1	−0.06 (15)

Cg1 is the centroid of the C7–C12 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2i	0.93	2.55	3.379 (2)	148.
C9—H9···Cg1ii	0.93	2.90	3.677 (2)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7–C12 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O2i	0.93	2.55	3.379 (2)	148
C9—H9⋯Cg1ii	0.93	2.90	3.677 (2)	142

Symmetry codes: (i) ; (ii) .