Diethyl 2-{[3-(2-meth­oxy­benz­yl)thio­phen-2-yl]methyl­idene}malonate

Ranjith, S.; Sakthi Murugesan, K.; Subbiah Pandi, A.; Dhayalan, V.; Mohana Krishnan, A.K.

doi:10.1107/S1600536811022525

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1688

doi:10.1107/S1600536811022525

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Diethyl 2-{[3-(2-methoxybenzyl)thiophen-2-yl]methylidene}malonate

S. Ranjith,^a K. Sakthi Murugesan,^a A. Subbiah Pandi,^a ^* V. Dhayalan ^b and A. K. Mohana Krishnan ^b

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: a_sp59@yahoo.in

(Received 16 April 2011; accepted 10 June 2011; online 18 June 2011)

In the title compound, C₂₀H₂₂O₅S, the dihedral angle between the mean planes through the thiophene and benzene rings is 75.2 (1)°. The methoxy group is essentially coplanar with the benzene ring, the largest deviation from the mean plane being 0.019 (2) Å for the O atom. The malonate group assumes an extended conformation.

Related literature

For the biological activities of thiophene derivatives, see: Bonini et al. (2005 ); Brault et al. (2005 ); Isloora et al. (2010 ); Xia et al. (2010 ). For a similar thiophene structure, see: Dufresne & Skene (2010 ).

Experimental

Crystal data

C₂₀H₂₂O₅S
M_r = 374.44
Orthorhombic, P b c a
a = 8.1680 (2) Å
b = 16.4046 (4) Å
c = 28.8651 (7) Å
V = 3867.72 (16) Å³
Z = 8
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 293 K
0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.953, T_max = 0.964
35690 measured reflections
3695 independent reflections
2687 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.145
S = 1.02
3695 reflections
238 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O2ⁱ	0.93	2.55	3.429 (3)	159
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007); 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/S1600536811022525/nk2101sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811022525/nk2101Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811022525/nk2101Isup3.cml

checkCIF report

Comment top

Thiophene derivatives exhibit anti-HIVPR inhibition (Bonini et al., 2005) and antibreast cancer (Brault et al., 2005) activity. In addition, some of the benzo[b]thiophene derivatives show significant antimicrobial and anti-inflammatory activity (Isloora et al., 2010). Thiophene derivates have been viewed as significant compounds for applications in many fields (Xia et al., 2010). Against this background, and in order to obtain detailed information on molecular conformations in the solid state, an X-ray study of the title compound was carried out.

X-Ray analysis confirms the molecular structure and atom connectivity as illustrated in Fig. 1. The bond lengths and angles in (Fig. 1) agree with those observed in other thiophene derivative (Dufresne & Skene, 2010). The thiophene ring system make the dihedral angle of 75.2 (1)° with respect to benzene ring. The atom O1 is deviated by 0.019 (2) Å from the least-squares plane of the benzene ring. The malonate group assumes an extended conformation as can be seen from torsion angles C14—C18—O5—C19 of 178.3 (2)° and C14—C15—O3—C16 of 173.9 (2)°.

Related literature top

For the biological activities of thiophene derivatives, see: Bonini et al. (2005); Brault et al. (2005); Isloora et al. (2010); Xia et al. (2010). For a similar thiophene structure, see: Dufresne & Skene (2010).

Experimental top

To a solution of diethyl-2-((3-(bromomethyl)thiophen-2-yl)methylene)malonate (2.88 mmol) in dry dichloroethane (15 ml), anhydrous ZnBr₂ (2.84 mmol) and anisole (3.17 mmol) were added. The reaction mixture was stirred at room temperature for 9 h and then refluxed for 1 h under N₂ atmosphere. The solvent was removed and the residue was quenched with ice–water (50 ml) containing 1 ml of Conc. HCl, extracted with chloroform (3 × 10 ml) and dried (Na₂SO₄). Removal of solvent followed by flash column chromatographic purification (n-hexane/ethyl acetate 98:2) led to the isolation of diethyl-2-((3-(2-methoxybenzyl)thiophen-2-yl) methylene)malonate as a colorless crystal. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in methanol at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 structure of the title compound with displacement ellipsoids at the 30% probability level.

Diethyl 2-{[3-(2-methoxybenzyl)thiophen-2-yl]methylidene}malonate top

Crystal data top

C₂₀H₂₂O₅S	F(000) = 1584
M_r = 374.44	D_x = 1.286 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3696 reflections
a = 8.1680 (2) Å	θ = 1.4–25.8°
b = 16.4046 (4) Å	µ = 0.19 mm⁻¹
c = 28.8651 (7) Å	T = 293 K
V = 3867.72 (16) Å³	Block, white
Z = 8	0.25 × 0.22 × 0.19 mm

Data collection top

Bruker APEXII CCD area detector diffractometer	3695 independent reflections
Radiation source: fine-focus sealed tube	2687 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
ω and ϕ scans	θ_max = 25.8°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.953, T_max = 0.964	k = −20→19
35690 measured reflections	l = −35→35

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.145	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0896P)² + 0.4403P] where P = (F_o² + 2F_c²)/3
3695 reflections	(Δ/σ)_max = 0.001
238 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₀H₂₂O₅S	V = 3867.72 (16) Å³
M_r = 374.44	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 8.1680 (2) Å	µ = 0.19 mm⁻¹
b = 16.4046 (4) Å	T = 293 K
c = 28.8651 (7) Å	0.25 × 0.22 × 0.19 mm

Data collection top

Bruker APEXII CCD area detector diffractometer	3695 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2687 reflections with I > 2σ(I)
T_min = 0.953, T_max = 0.964	R_int = 0.053
35690 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.145	H-atom parameters constrained
S = 1.02	Δρ_max = 0.30 e Å⁻³
3695 reflections	Δρ_min = −0.21 e Å⁻³
238 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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.

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

	x	y	z	U_iso*/U_eq
C1	0.2480 (3)	0.84683 (13)	0.40960 (7)	0.0502 (5)
H1	0.2853	0.7955	0.4182	0.060*
C2	0.0917 (3)	0.87086 (14)	0.41448 (8)	0.0577 (6)
H2	0.0097	0.8382	0.4270	0.069*
C3	0.2653 (2)	0.97752 (12)	0.37999 (6)	0.0406 (5)
C4	0.3501 (2)	0.90728 (11)	0.39004 (6)	0.0391 (4)
C5	0.5308 (2)	0.89232 (12)	0.38274 (6)	0.0416 (5)
H5A	0.5455	0.8420	0.3656	0.050*
H5B	0.5764	0.9363	0.3644	0.050*
C6	0.6220 (2)	0.88675 (12)	0.42814 (6)	0.0392 (4)
C7	0.6554 (3)	0.81224 (12)	0.44834 (7)	0.0499 (5)
H7	0.6246	0.7646	0.4332	0.060*
C8	0.7338 (3)	0.80722 (15)	0.49063 (8)	0.0605 (6)
H8	0.7551	0.7566	0.5039	0.073*
C9	0.7800 (3)	0.87723 (15)	0.51296 (7)	0.0600 (6)
H9	0.8333	0.8739	0.5414	0.072*
C10	0.7487 (3)	0.95238 (14)	0.49386 (7)	0.0541 (6)
H10	0.7799	0.9996	0.5094	0.065*
C11	0.6703 (2)	0.95747 (11)	0.45135 (7)	0.0415 (5)
C12	0.6731 (3)	1.10362 (14)	0.45138 (9)	0.0702 (7)
H12A	0.6190	1.1058	0.4809	0.105*
H12B	0.6364	1.1481	0.4325	0.105*
H12C	0.7893	1.1076	0.4559	0.105*
C13	0.3340 (2)	1.05129 (11)	0.36133 (6)	0.0410 (5)
H13	0.4477	1.0519	0.3598	0.049*
C14	0.2619 (2)	1.11897 (12)	0.34583 (6)	0.0418 (5)
C15	0.0810 (2)	1.13214 (12)	0.34553 (7)	0.0467 (5)
C16	−0.1688 (3)	1.09125 (18)	0.31161 (12)	0.0825 (9)
H16A	−0.2077	1.1441	0.3013	0.099*
H16B	−0.2117	1.0811	0.3424	0.099*
C17	−0.2233 (4)	1.0273 (3)	0.27952 (11)	0.1122 (13)
H17A	−0.1722	1.0351	0.2499	0.168*
H17B	−0.3401	1.0300	0.2761	0.168*
H17C	−0.1933	0.9748	0.2916	0.168*
C18	0.3658 (3)	1.18679 (13)	0.32912 (8)	0.0541 (6)
C19	0.3623 (4)	1.31693 (16)	0.29168 (9)	0.0758 (8)
H19A	0.2947	1.3649	0.2963	0.091*
H19B	0.4635	1.3244	0.3088	0.091*
C20	0.3981 (4)	1.3071 (2)	0.24258 (10)	0.0962 (10)
H20A	0.4699	1.2614	0.2383	0.144*
H20B	0.4500	1.3556	0.2311	0.144*
H20C	0.2980	1.2980	0.2259	0.144*
O1	0.63527 (19)	1.02826 (8)	0.42901 (5)	0.0542 (4)
O2	0.0111 (2)	1.17398 (10)	0.37271 (7)	0.0752 (5)
O3	0.00937 (18)	1.08978 (10)	0.31226 (5)	0.0587 (4)
O4	0.5109 (2)	1.18958 (11)	0.33296 (8)	0.0910 (7)
O5	0.2766 (2)	1.24465 (9)	0.30883 (5)	0.0639 (5)
S1	0.06061 (7)	0.96745 (4)	0.39524 (2)	0.0526 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0581 (14)	0.0429 (11)	0.0496 (11)	−0.0054 (10)	−0.0043 (10)	0.0073 (9)
C2	0.0579 (15)	0.0586 (14)	0.0565 (13)	−0.0150 (12)	0.0021 (11)	0.0091 (11)
C3	0.0398 (11)	0.0421 (11)	0.0399 (10)	0.0006 (8)	−0.0028 (8)	−0.0007 (8)
C4	0.0450 (12)	0.0387 (10)	0.0338 (9)	−0.0009 (8)	−0.0038 (8)	−0.0015 (8)
C5	0.0489 (12)	0.0380 (10)	0.0378 (10)	0.0053 (9)	−0.0007 (9)	−0.0010 (8)
C6	0.0382 (10)	0.0396 (10)	0.0397 (10)	0.0030 (8)	0.0012 (8)	−0.0015 (8)
C7	0.0595 (14)	0.0385 (11)	0.0516 (12)	0.0054 (10)	−0.0067 (10)	−0.0025 (9)
C8	0.0754 (16)	0.0534 (14)	0.0526 (13)	0.0114 (12)	−0.0090 (11)	0.0089 (10)
C9	0.0710 (16)	0.0669 (16)	0.0422 (12)	0.0082 (13)	−0.0118 (11)	0.0015 (11)
C10	0.0600 (14)	0.0544 (14)	0.0478 (12)	−0.0047 (10)	−0.0056 (11)	−0.0106 (10)
C11	0.0420 (11)	0.0369 (10)	0.0457 (11)	0.0004 (8)	0.0015 (9)	−0.0011 (8)
C12	0.0827 (18)	0.0391 (12)	0.0889 (18)	−0.0098 (12)	−0.0012 (14)	−0.0097 (12)
C13	0.0364 (10)	0.0416 (11)	0.0450 (11)	0.0006 (8)	0.0001 (8)	−0.0002 (8)
C14	0.0389 (11)	0.0385 (10)	0.0480 (11)	0.0017 (8)	0.0007 (9)	−0.0007 (8)
C15	0.0447 (12)	0.0361 (10)	0.0592 (13)	0.0028 (9)	0.0043 (10)	0.0044 (10)
C16	0.0380 (13)	0.088 (2)	0.121 (2)	0.0024 (13)	−0.0115 (14)	0.0139 (18)
C17	0.070 (2)	0.178 (4)	0.088 (2)	−0.035 (2)	−0.0234 (17)	0.002 (2)
C18	0.0474 (14)	0.0444 (12)	0.0706 (14)	0.0025 (10)	0.0056 (11)	0.0067 (11)
C19	0.096 (2)	0.0568 (15)	0.0747 (17)	−0.0089 (14)	0.0089 (15)	0.0113 (13)
C20	0.111 (3)	0.101 (2)	0.0764 (19)	−0.0050 (19)	0.0193 (17)	0.0097 (17)
O1	0.0689 (10)	0.0344 (7)	0.0593 (9)	−0.0046 (7)	−0.0092 (7)	−0.0008 (6)
O2	0.0597 (10)	0.0637 (11)	0.1023 (13)	0.0107 (9)	0.0193 (10)	−0.0254 (10)
O3	0.0378 (8)	0.0702 (10)	0.0681 (10)	0.0033 (7)	−0.0059 (7)	−0.0051 (8)
O4	0.0428 (10)	0.0703 (12)	0.160 (2)	−0.0049 (9)	0.0016 (11)	0.0353 (12)
O5	0.0642 (10)	0.0492 (9)	0.0782 (11)	−0.0018 (8)	−0.0022 (8)	0.0227 (8)
S1	0.0422 (3)	0.0553 (4)	0.0603 (4)	−0.0012 (2)	0.0033 (2)	0.0067 (3)

Geometric parameters (Å, º) top

C1—C2	1.344 (3)	C12—H12B	0.9600
C1—C4	1.413 (3)	C12—H12C	0.9600
C1—H1	0.9300	C13—C14	1.334 (3)
C2—S1	1.698 (2)	C13—H13	0.9300
C2—H2	0.9300	C14—C18	1.480 (3)
C3—C4	1.375 (3)	C14—C15	1.493 (3)
C3—C13	1.439 (3)	C15—O2	1.189 (2)
C3—S1	1.737 (2)	C15—O3	1.322 (3)
C4—C5	1.511 (3)	C16—O3	1.456 (3)
C5—C6	1.510 (3)	C16—C17	1.469 (4)
C5—H5A	0.9700	C16—H16A	0.9700
C5—H5B	0.9700	C16—H16B	0.9700
C6—C7	1.381 (3)	C17—H17A	0.9600
C6—C11	1.396 (3)	C17—H17B	0.9600
C7—C8	1.381 (3)	C17—H17C	0.9600
C7—H7	0.9300	C18—O4	1.192 (3)
C8—C9	1.370 (3)	C18—O5	1.332 (3)
C8—H8	0.9300	C19—C20	1.456 (4)
C9—C10	1.375 (3)	C19—O5	1.463 (3)
C9—H9	0.9300	C19—H19A	0.9700
C10—C11	1.387 (3)	C19—H19B	0.9700
C10—H10	0.9300	C20—H20A	0.9600
C11—O1	1.359 (2)	C20—H20B	0.9600
C12—O1	1.429 (3)	C20—H20C	0.9600
C12—H12A	0.9600

C2—C1—C4	113.4 (2)	H12B—C12—H12C	109.5
C2—C1—H1	123.3	C14—C13—C3	130.83 (19)
C4—C1—H1	123.3	C14—C13—H13	114.6
C1—C2—S1	112.43 (17)	C3—C13—H13	114.6
C1—C2—H2	123.8	C13—C14—C18	118.84 (18)
S1—C2—H2	123.8	C13—C14—C15	123.97 (18)
C4—C3—C13	125.96 (18)	C18—C14—C15	117.16 (17)
C4—C3—S1	110.60 (15)	O2—C15—O3	124.75 (19)
C13—C3—S1	123.39 (15)	O2—C15—C14	123.7 (2)
C3—C4—C1	112.01 (18)	O3—C15—C14	111.48 (17)
C3—C4—C5	126.77 (17)	O3—C16—C17	107.4 (2)
C1—C4—C5	121.21 (18)	O3—C16—H16A	110.2
C6—C5—C4	111.75 (15)	C17—C16—H16A	110.2
C6—C5—H5A	109.3	O3—C16—H16B	110.2
C4—C5—H5A	109.3	C17—C16—H16B	110.2
C6—C5—H5B	109.3	H16A—C16—H16B	108.5
C4—C5—H5B	109.3	C16—C17—H17A	109.5
H5A—C5—H5B	107.9	C16—C17—H17B	109.5
C7—C6—C11	118.48 (17)	H17A—C17—H17B	109.5
C7—C6—C5	121.15 (17)	C16—C17—H17C	109.5
C11—C6—C5	120.34 (17)	H17A—C17—H17C	109.5
C6—C7—C8	121.2 (2)	H17B—C17—H17C	109.5
C6—C7—H7	119.4	O4—C18—O5	123.9 (2)
C8—C7—H7	119.4	O4—C18—C14	124.7 (2)
C9—C8—C7	119.6 (2)	O5—C18—C14	111.45 (18)
C9—C8—H8	120.2	C20—C19—O5	109.6 (2)
C7—C8—H8	120.2	C20—C19—H19A	109.7
C8—C9—C10	120.78 (19)	O5—C19—H19A	109.7
C8—C9—H9	119.6	C20—C19—H19B	109.7
C10—C9—H9	119.6	O5—C19—H19B	109.7
C9—C10—C11	119.7 (2)	H19A—C19—H19B	108.2
C9—C10—H10	120.2	C19—C20—H20A	109.5
C11—C10—H10	120.2	C19—C20—H20B	109.5
O1—C11—C10	124.65 (18)	H20A—C20—H20B	109.5
O1—C11—C6	115.03 (17)	C19—C20—H20C	109.5
C10—C11—C6	120.32 (18)	H20A—C20—H20C	109.5
O1—C12—H12A	109.5	H20B—C20—H20C	109.5
O1—C12—H12B	109.5	C11—O1—C12	118.66 (17)
H12A—C12—H12B	109.5	C15—O3—C16	116.32 (19)
O1—C12—H12C	109.5	C18—O5—C19	117.7 (2)
H12A—C12—H12C	109.5	C2—S1—C3	91.58 (10)

C4—C1—C2—S1	0.5 (2)	S1—C3—C13—C14	−10.9 (3)
C13—C3—C4—C1	177.77 (18)	C3—C13—C14—C18	178.9 (2)
S1—C3—C4—C1	0.3 (2)	C3—C13—C14—C15	0.9 (3)
C13—C3—C4—C5	−1.4 (3)	C13—C14—C15—O2	103.5 (3)
S1—C3—C4—C5	−178.86 (14)	C18—C14—C15—O2	−74.5 (3)
C2—C1—C4—C3	−0.5 (3)	C13—C14—C15—O3	−74.7 (2)
C2—C1—C4—C5	178.72 (18)	C18—C14—C15—O3	107.2 (2)
C3—C4—C5—C6	110.5 (2)	C13—C14—C18—O4	−8.6 (3)
C1—C4—C5—C6	−68.6 (2)	C15—C14—C18—O4	169.6 (2)
C4—C5—C6—C7	96.2 (2)	C13—C14—C18—O5	171.06 (18)
C4—C5—C6—C11	−81.9 (2)	C15—C14—C18—O5	−10.8 (3)
C11—C6—C7—C8	0.4 (3)	C10—C11—O1—C12	−3.5 (3)
C5—C6—C7—C8	−177.7 (2)	C6—C11—O1—C12	176.92 (18)
C6—C7—C8—C9	−0.2 (4)	O2—C15—O3—C16	−4.3 (3)
C7—C8—C9—C10	0.3 (4)	C14—C15—O3—C16	173.90 (19)
C8—C9—C10—C11	−0.4 (4)	C17—C16—O3—C15	−167.5 (2)
C9—C10—C11—O1	−179.0 (2)	O4—C18—O5—C19	−2.1 (4)
C9—C10—C11—C6	0.5 (3)	C14—C18—O5—C19	178.30 (19)
C7—C6—C11—O1	179.11 (18)	C20—C19—O5—C18	95.8 (3)
C5—C6—C11—O1	−2.8 (3)	C1—C2—S1—C3	−0.25 (18)
C7—C6—C11—C10	−0.5 (3)	C4—C3—S1—C2	−0.03 (16)
C5—C6—C11—C10	177.62 (19)	C13—C3—S1—C2	−177.60 (17)
C4—C3—C13—C14	171.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O2ⁱ	0.93	2.55	3.429 (3)	159

Symmetry code: (i) −x+1/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₂O₅S
M_r	374.44
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	8.1680 (2), 16.4046 (4), 28.8651 (7)
V (Å³)	3867.72 (16)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.25 × 0.22 × 0.19

Data collection
Diffractometer	Bruker APEXII CCD area detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.953, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	35690, 3695, 2687
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.612

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.145, 1.02
No. of reflections	3695
No. of parameters	238
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.21

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O2ⁱ	0.93	2.55	3.429 (3)	158.5

Symmetry code: (i) −x+1/2, y−1/2, z.

Acknowledgements

SR and ASP thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.

References

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