Methyl (2E)-2-[(2,4-dioxo-1,3-thia­zolidin-3-yl)meth­yl]-3-phenyl­prop-2-enoate

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

doi:10.1107/S1600536812000578

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages o328-o329

doi:10.1107/S1600536812000578

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Methyl (2E)-2-[(2,4-dioxo-1,3-thiazolidin-3-yl)methyl]-3-phenylprop-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 2 January 2012; accepted 6 January 2012; online 11 January 2012)

In the title compound, C₁₄H₁₃NO₄S, the thiazolidine 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, molecules 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 interactions 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 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_r = 291.31
Orthorhombic, P c a 2₁
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[F² > 2σ(F²)] = 0.030
wR(F²) = 0.082
S = 1.03
2948 reflections
182 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.22 e Å⁻³
Absolute structure: Flack (1983 ), 1348 Friedel pairs
Flack parameter: 0.01 (7)

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) $[-x+2, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[x+{\script{3\over 2}}, -y, z]$ ; (iii) $[-x+2, -y, z-{\script{1\over 2}}]$ .

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/S1600536812000578/bt5778sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812000578/bt5778Isup3.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 thiazolidine ring (S1/N1/C1–C3) is essentially planar [maximum deviation = 0.010 (2) Å for the C3 atom] and lies at an angle 60.1 (1)° with respect to the benzene ring. The significant difference in length of the C13—O4 = 1.333 (2) Å and C14—O4 = 1.445 (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 (359°) 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, Vijayakumar et al., 2012).

In the crystal, intermolecular C—H···O hydrogen bonds invoving atoms C2 and O1 link molecules into C(4) chains running along c axis (Fig. 2). The crystal packing is further stabilized by C—H···π interactions, the first one between a benzene H atom and the benzene ring (C7–C12) of an adjacent molecule, with a C9—H9···Cgⁱⁱ seperation of 2.81 Å and the second one between a benzene H atom and the benzene ring (C7–C12) of a neighbouring molecule, with a C12—H12···Cgⁱⁱⁱ seperation of 2.80 Å ( Table 1 and Fig. 3; Cg is the centroid of the C7–C12 benzene ring , symmetry code as in Fig. 3).

Related literature top

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 acrylate, see: Merlino (1971); Varghese et al. (1986). For closely related structures, see: Fun et al. (2009); Vijayakumar et al. (2012).

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, methyl (2Z)-methyl-2 -(bromomethyl)-3-phenylprop-2-enoate (1 mmol, 0.254 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 (0.285 g, 98% 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 C(4) chains along c axis. [Symmetry code: (i)2-x, 1-y, -1/2+z; (iv) x, y, -1+z; (v)2-x, 1-y, -3/2+z; (vi)x, y, -2+z; (vii)2-x, 1-y, -5/2+z].
	Fig. 3. A view of the C—H···π interactions, in the molecular structure of the title compound. Cg is the centroid of the (C7–C12) benzene ring. [Symmetry code: (ii) 3/2-x, y, 1/2+z; (iii) 2-x, -y, -1/2+z.]

Methyl (2E)-2-[(2,4-dioxo-1,3-thiazolidin-3-yl)methyl]-3- phenylprop-2-enoate top

Crystal data top

C₁₄H₁₃NO₄S	F(000) = 608
M_r = 291.31	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0474P)² + 0.0813P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
2948 reflections	Δρ_max = 0.12 e Å⁻³
182 parameters	Δρ_min = −0.22 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1348 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (7)

Crystal data top

C₁₄H₁₃NO₄S	V = 1357.90 (8) Å³
M_r = 291.31	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 11.9274 (3) Å	µ = 0.25 mm⁻¹
b = 15.6064 (6) Å	T = 293 K
c = 7.2949 (3) Å	0.26 × 0.22 × 0.18 mm

Data collection top

Bruker APEXII CCD diffractometer	2948 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2576 reflections with I > 2σ(I)
T_min = 0.937, T_max = 0.956	R_int = 0.026
13845 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	H-atom parameters constrained
wR(F²) = 0.082	Δρ_max = 0.12 e Å⁻³
S = 1.03	Δρ_min = −0.22 e Å⁻³
2948 reflections	Absolute structure: Flack (1983), 1348 Friedel pairs
182 parameters	Absolute structure parameter: 0.01 (7)
1 restraint

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
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y+1, z−1/2; (ii) x+3/2, −y, z; (iii) −x+2, −y, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃NO₄S
M_r	291.31
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	293
a, b, c (Å)	11.9274 (3), 15.6064 (6), 7.2949 (3)
V (Å³)	1357.90 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.26 × 0.22 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.937, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	13845, 2948, 2576
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.638

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.082, 1.03
No. of reflections	2948
No. of parameters	182
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.22
Absolute structure	Flack (1983), 1348 Friedel pairs
Absolute structure parameter	0.01 (7)

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

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)	144.8
C9—H9···Cgⁱⁱ	0.93	2.81	3.522 (2)	134.0
C12—H12···Cgⁱⁱⁱ	0.93	2.80	3.541 (2)	137.0

Symmetry codes: (i) −x+2, −y+1, z−1/2; (ii) x+3/2, −y, z; (iii) −x+2, −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

Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, H. S., Li, Z. M. & Han, Y. F. (2000). J. Agric. Food Chem. 48, 5312–5315. Web of Science CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Fun, H.-K., Goh, J. H., Vinayaka, A. C. & Kalluraya, B. (2009). Acta Cryst. E65, o2094. Web of Science CSD CrossRef IUCr Journals Google Scholar
Jacop, J. & Kutty, G. N. (2004). Indian Drugs, 41, 76–79. Google Scholar
Kalia, R., Rao, C. M. & Kutty, N. G. (2007). Arzneim. Forsch. (Drug Res.), 57, 616–622. CAS Google Scholar
Merlino, S. (1971). Acta Cryst. B27, 2491–2492. CrossRef CAS IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Varghese, B., Srinivasan, S., Padmanabhan, P. V. & Ramadas, S. R. (1986). Acta Cryst. C42, 1544–1546. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Vicentini, C. B., Manfrini, M., Veronese, A. C. & Guarneri, M. (1998). J. Heterocycl. Chem. 35, 29–36. CrossRef CAS Google Scholar
Vigorita, M. G., Basile, M., Zappala, C., Gabbrielli, G. & Pizzimenti, F. (1992). Farmaco, 47, 893–906. PubMed CAS Web of Science Google Scholar
Vijayakumar, S., Murugavel, S., Kannan, D. & Bakthadoss, M. (2012). Acta Cryst. E68, o156–o157. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 2| February 2012| Pages o328-o329

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