Methyl (Z)-2-[(2,4-dioxothia­zolidin-3-yl)meth­yl]-3-(2-methyl­phen­yl)prop-2-enoate

Vijayakumar, S.; Murugavel, S.; Kannan, D.; Bakthadoss, M.

doi:10.1107/S1600536811053682

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Pages o156-o157

doi:10.1107/S1600536811053682

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Methyl (Z)-2-[(2,4-dioxothiazolidin-3-yl)methyl]-3-(2-methylphenyl)prop-2-enoate

S. Vijayakumar,^a S. Murugavel,^b ^* D. Kannan ^c and M. Bakthadoss ^c ‡

^aDepartment of Physics, Sri Balaji Chokkalingam Engineering College, Arni, Thiruvannamalai 632 317, India, ^bDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India, and ^cDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
^*Correspondence e-mail: smurugavel27@gmail.com

(Received 9 December 2011; accepted 13 December 2011; online 17 December 2011)

The C=C bond in the title compound, C₁₅H₁₅NO₄S, has a Z configuration. The thiazolidine 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 molecules into dimers, generating R₂²(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)°] interactions.

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 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_r = 305.34
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.045
wR(F²) = 0.135
S = 1.04
4354 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.32 e Å⁻³

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) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (ii) $[x+1, -y, z-{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811053682/bt5747sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811053682/bt5747Isup3.cml

checkCIF report

Comment top

Thiazolidine derivatives exhibit herbicidal (Chen et al., 2000; Vicentini et al., 1998), antineoplastic (Vigorita et al., 1992), hypolipidemic (Jacop & Kutty, 2004) and anti-inflammatory (Kalia et al., 2007) activities. In view of this importance, the crystal structure of the title compound has been carried out and the results are presented here.

Fig. 1. shows a displacement ellipsoid plot of (I), with the atom numbering scheme. The molecules of the title compound display a Z– configuration about the C6═C5 double bond. The thiazolidine moiety (S1/N1/C1-C3) is essentially planar [maximum deviation = -0.008 (1) Å for the N1 atom] and lies at an angle 59.1 (1)° with respect to the benzene ring. The significant difference in length of the C13—O4 = 1.334 (2) Å and C14—O4 = 1.446 (2) Å bonds is attributed to a partial contribution from the O^-–C = O⁺–C resonance structure of the O3═C13—O4—C14 group (Merlino, 1971). This feature, commonly observed in the carboxylic ester group of the substituents in various compounds gives average values of 1.340 Å and 1.447 Å respectively for these bonds (Varghese et al., 1986). The sum of bond angles around N1 (360°) indicates that N1 is in sp² hybridization. The geometric parameters of the title molecule agrees well with those reported for similar structures (Fun et al., 2009, Vennila et al., 2011).

In the crystal packing (Fig. 2), the molecules at x, y, z and 1-x, y, 1/2-z are linked by C8—H8···O2 hydrogen bonds into cyclic centrosymmetric R₂²(18) dimers (Bernstein et al., 1995). The crystal packing is further stabilized by C—H···π and C—O···π interactions, the first one between a H9 atom and neighbouring benene ring (C7–C12), with a C9—H9···Cg1ⁱⁱ seperation of 2.90 Å (Fig. 3 and Table 1; Cg1 is the centroid of the C7–C12 benzene ring, Symmetry code as in Fig.3), and the second one between oxygen atom O1 and neighbouring thiazolidine ring (N1/S1/C1–C3), with a Ol···centroid(Cg2ⁱⁱⁱ) distance of 3.412 (2) Å and a C1—O1···Cg2ⁱⁱⁱ angle of 115.0 (1)° (Fig. 3; Cg2 is the centroid of the N1/S1/C1—C3 thiazolidine ring, Symmetry code as in Fig. 3).

Related literature top

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 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 top

A solution of thiazolidine-2,4-dione (1 mmol, 0.117 g) and potassium carbonate (1.5 mmol, 0.207 g) in acetonitrile solvent was stirred for 15 minutes at room temperature. To this solution, (Z)-methyl-2 -(bromomethyl)-3-(2-methylphenyl)-prop-2-enoate (1 mmol, 0.269 g) was added dropwise till the addition is complete. After the completion of the reaction, as indicated by TLC, acetonitrile was evaporated. Ethyl acetate (15 ml) and water (15 ml) were added to the crude mass. The organic layer was dried over anhydrous sodium sulfate. Removal of solvent led to the crude product, which was purified through pad of silica gel (100–200 mesh) using ethylacetate and hexanes (1:9) as solvents. The pure title compound was obtained as a colourless solid (0.290 g, 95% yield). Recrystallization was carried out using ethylacetate as solvent.

Computing details top

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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. Part of the crystal structure of the title compound showing C—H···O intermolecular hydrogen bonds (dotted lines) generating R²₂(18) centrosymmetric dimer. [Symmetry code: (i) 1-x, y, 1/2-z].
	Fig. 3. A view of the C—H···π (red dotted lines) and C—O···π (blue dotted lines) interactions, in the molecular structure of the title compound. Cg1 and Cg2 are the centroids of the (C7–C12) benzene ring and (N1/S1/C1–C3) thiazolidine ring, respectively. [Symmetry code: (ii) 3/2-x, 1/2+y, 1/2-z; (iii) 1-x, 2-y, -z.]

Methyl (Z)-2-[(2,4-dioxothiazolidin-3-yl)methyl]- 3-(2-methylphenyl)prop-2-enoate top

Crystal data top

C₁₅H₁₅NO₄S	F(000) = 1280
M_r = 305.34	D_x = 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

Data collection top

Bruker APEXII CCD diffractometer	4354 independent reflections
Radiation source: fine-focus sealed tube	2966 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 10.0 pixels mm^-1	θ_max = 30.2°, θ_min = 2.0°
ω scans	h = −29→30
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −9→8
T_min = 0.941, T_max = 0.959	l = −28→18
18757 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0612P)² + 1.2153P] where P = (F_o² + 2F_c²)/3
4354 reflections	(Δ/σ)_max < 0.001
192 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₅H₁₅NO₄S	V = 2946.3 (2) Å³
M_r = 305.34	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 21.3744 (10) Å	µ = 0.23 mm⁻¹
b = 6.9762 (3) Å	T = 293 K
c = 20.3084 (10) Å	0.26 × 0.23 × 0.18 mm
β = 103.361 (2)°

Data collection top

Bruker APEXII CCD diffractometer	4354 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2966 reflections with I > 2σ(I)
T_min = 0.941, T_max = 0.959	R_int = 0.027
18757 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.04	Δρ_max = 0.26 e Å⁻³
4354 reflections	Δρ_min = −0.32 e Å⁻³
192 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, y, −z+1/2; (ii) x+1, −y, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅NO₄S
M_r	305.34
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	21.3744 (10), 6.9762 (3), 20.3084 (10)
β (°)	103.361 (2)
V (Å³)	2946.3 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.26 × 0.23 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.941, 0.959
No. of measured, independent and observed [I > 2σ(I)] reflections	18757, 4354, 2966
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.708

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.135, 1.04
No. of reflections	4354
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.32

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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)	148.0
C9—H9···Cg1ⁱⁱ	0.93	2.90	3.677 (2)	142

Symmetry codes: (i) −x+1, y, −z+1/2; (ii) x+1, −y, z−1/2.

Footnotes

‡Additional correspondence author, e-mail: bhakthadoss@yahoo.com.

Acknowledgements

The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

References

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Volume 68| Part 1| January 2012| Pages o156-o157

doi:10.1107/S1600536811053682

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

Methyl (Z)-2-[(2,4-dioxo­thia­zolidin-3-yl)meth­yl]-3-(2-methyl­phen­yl)prop-2-enoate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

Methyl (Z)-2-[(2,4-dioxothiazolidin-3-yl)methyl]-3-(2-methylphenyl)prop-2-enoate