(3,4-Dimeth­oxy­phen­yl)[2-(thio­phen-2-ylcarbon­yl)phen­yl]methanone

Ganesh, G.; Sivasakthikumaran, R.; Govindan, E.; Krishnan, A.K.M.; SubbiahPandi, A.

doi:10.1107/S1600536812037336

organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page o2844

https://doi.org/10.1107/S1600536812037336

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(3,4-Dimethoxyphenyl)[2-(thiophen-2-ylcarbonyl)phenyl]methanone

G. Ganesh,^a R. Sivasakthikumaran,^b E. Govindan,^c A. K. Mohana Krishnan ^b and A. SubbiahPandi ^c ^*

^aDepartment of Physics, S.M.K. Fomra Institute of Technology, Thaiyur, Chennai 603 103, India, ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and ^cDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India
^*Correspondence e-mail: a_sp59@yahoo.in

(Received 30 June 2012; accepted 29 August 2012; online 5 September 2012)

In the title compound, C₂₀H₁₆O₄S, the thiophene ring makes dihedral angles of 72.9 (2) and 60.5 (2)°, respectively, with the dimethoxy benzene and phenyl rings. In the crystal, C—H⋯O hydrogen bonds link the molecules into a C(9) chain along the b axis. The S and C atoms of the thiophene ring are disordered over two sets of sites [site occupancies = 0.675 (3) and 0.325 (3)]. A short intermolecular S⋯O contact [3.084 (2) Å] is observed in the crystal structure, which also features C—H⋯π interactions.

Related literature

For background to thiophene derivatives and their biological activity, see: Bonini et al. (2005 ); Khan et al. (2009 ); Brault et al. (2005 ); Isloora et al. (2010 ); Xia et al. (2010 ). For related structures, see: Asiri et al. (2010 ); Aslam et al. (2011 ).

Experimental

Crystal data

C₂₀H₁₆O₄S
M_r = 352.40
Orthorhombic, P b c a
a = 15.7324 (6) Å
b = 10.7988 (5) Å
c = 20.4877 (11) Å
V = 3480.7 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.21 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 = 0.950, T_max = 0.961
22015 measured reflections
4469 independent reflections
2968 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.107
S = 1.03
4469 reflections
236 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C17/C19/C20/S1′/C18′ ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O4ⁱ	0.93	2.58	3.496 (2)	169
C1—H1A⋯Cg2ⁱⁱ	0.96	2.99	3.799 (3)	143
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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: https://doi.org/10.1107/S1600536812037336/bt5963sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812037336/bt5963Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812037336/bt5963Isup3.mol

Supporting information file. DOI: https://doi.org/10.1107/S1600536812037336/bt5963Isup4.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). Schiff bases are well known ligands in coordination chemistry with a wide range of biological activities (Khan et al., 2009). Against this background, and in order to obtain detailed information on molecular 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 S1—C20 and O2—C8 are normal and comparable to the corresponding values observed in the related structure of (2E)-1-(2,5-Dimethyl-3-thienyl)-3-(2-methoxyphenyl)prop-2-en-1-one (Asiri et al., 2010). The thiophene ring system makes dihedral angles of 72.9 (2) ° and 60.5 (2) °, respectively, with the dimethoxy benzene and the phenyl ring. The atoms O1 and O2 are deviated by -0.002 (1) Å and -0.010 (1) Å from the least squares plane of the C2—C7 ring. The atoms C18 and S1 of the thiophene ring are disordered over two positions [site occupancies = 0.648 (2) and 0.352 (2)].

The atom C3 acts as a donor to the atom O4 of the neighbour molecule at (-x,-1/2 + y, -z). This hydrogen bond is involved in a motif C(9) chain along b axis. Interestingly, a short non-hydrogen intermolecular contact between S1···O2 [3.084 (2) Å] at (1/2 - x,1 - y,-1/2 + z) was observed in the crystal structure. In addition to van der Waals interactions, the crystal packing is stabilized by C—H···π interaction between one of the methyl H atom (H1A) and the centroid (Cg2) of the thiophene ring (Table 1).

Related literature top

For background to thiophene derivatives and their biological activity, see: Bonini et al. (2005); Khan et al. (2009); Brault et al. (2005); Isloora et al. (2010); Xia et al. (2010). For related structures, see: Asiri et al. (2010); Aslam et al. (2011).

Experimental top

To a stirred suspension of benzoic (1 g, 3.44 mmol) in dry THF (20 ml) lead tetra acetate (1.5 g, 3.42 mmol) was added and refluxed at 50 °C for half an hour. The reaction mixture was then poured into water (200 ml) and extracted with ethyl acetate (2x20 ml), washed with brine solution and dried (Na₂SO₄). The removal of solvent in vacuo afforded the crude product upon crystallization from methanol furnished the title compound as a color less solid.

Structure description top

For background to thiophene derivatives and their biological activity, see: Bonini et al. (2005); Khan et al. (2009); Brault et al. (2005); Isloora et al. (2010); Xia et al. (2010). For related structures, see: Asiri et al. (2010); Aslam et al. (2011).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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, showing displacement ellipsoids drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. The molecular structure showing the major and minor occupied site of the disordered atoms.

(3,4-Dimethoxyphenyl)[2-(thiophen-2-ylcarbonyl)phenyl]methanone top

Crystal data top

C₂₀H₁₆O₄S	F(000) = 1472
M_r = 352.40	D_x = 1.345 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4469 reflections
a = 15.7324 (6) Å	θ = 2.4–28.6°
b = 10.7988 (5) Å	µ = 0.21 mm⁻¹
c = 20.4877 (11) Å	T = 293 K
V = 3480.7 (3) Å³	Block, white crystalline
Z = 8	0.25 × 0.22 × 0.19 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	4469 independent reflections
Radiation source: fine-focus sealed tube	2968 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω and φ scans	θ_max = 28.6°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→12
T_min = 0.950, T_max = 0.961	k = −14→13
22015 measured reflections	l = −26→27

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)] = 0.040	H-atom parameters constrained
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.0418P)² + 0.6807P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
4469 reflections	Δρ_max = 0.19 e Å⁻³
236 parameters	Δρ_min = −0.20 e Å⁻³
4 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0032 (4)

Crystal data top

C₂₀H₁₆O₄S	V = 3480.7 (3) Å³
M_r = 352.40	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 15.7324 (6) Å	µ = 0.21 mm⁻¹
b = 10.7988 (5) Å	T = 293 K
c = 20.4877 (11) Å	0.25 × 0.22 × 0.19 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	4469 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2968 reflections with I > 2σ(I)
T_min = 0.950, T_max = 0.961	R_int = 0.029
22015 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	4 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.03	Δρ_max = 0.19 e Å⁻³
4469 reflections	Δρ_min = −0.20 e Å⁻³
236 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	Occ. (<1)
C1	0.07420 (12)	0.29212 (17)	0.52465 (9)	0.0702 (5)
H1A	0.0927	0.2750	0.5684	0.105*
H1B	0.0939	0.2278	0.4960	0.105*
H1C	0.0132	0.2953	0.5235	0.105*
C2	0.08842 (9)	0.44770 (14)	0.44314 (7)	0.0447 (3)
C3	0.03902 (9)	0.38431 (14)	0.39886 (7)	0.0487 (4)
H3	0.0165	0.3075	0.4099	0.058*
C4	0.02285 (9)	0.43475 (14)	0.33805 (7)	0.0471 (3)
H4	−0.0110	0.3917	0.3086	0.056*
C5	0.05654 (8)	0.54875 (13)	0.32047 (7)	0.0419 (3)
C6	0.10764 (8)	0.61269 (13)	0.36538 (7)	0.0432 (3)
H6	0.1313	0.6885	0.3539	0.052*
C7	0.12280 (9)	0.56397 (14)	0.42603 (7)	0.0448 (3)
C8	0.20416 (12)	0.73733 (16)	0.46082 (9)	0.0669 (5)
H8A	0.2364	0.7649	0.4979	0.100*
H8B	0.1584	0.7942	0.4528	0.100*
H8C	0.2404	0.7337	0.4232	0.100*
C10	−0.02731 (9)	0.55919 (13)	0.21288 (7)	0.0432 (3)
C11	−0.10859 (9)	0.55142 (16)	0.23926 (9)	0.0567 (4)
H11	−0.1164	0.5629	0.2838	0.068*
C12	−0.17778 (10)	0.52680 (18)	0.19982 (10)	0.0672 (5)
H12	−0.2320	0.5229	0.2178	0.081*
C13	−0.16671 (11)	0.50815 (17)	0.13424 (10)	0.0664 (5)
H13	−0.2134	0.4912	0.1079	0.080*
C14	−0.08662 (10)	0.51440 (15)	0.10716 (8)	0.0567 (4)
H14	−0.0796	0.5011	0.0626	0.068*
C15	−0.01622 (9)	0.54042 (13)	0.14591 (7)	0.0443 (3)
C16	0.06748 (10)	0.54873 (14)	0.11162 (7)	0.0496 (4)
C17	0.13814 (9)	0.47030 (14)	0.13224 (7)	0.0464 (3)
C9	0.04505 (9)	0.60239 (13)	0.25482 (7)	0.0436 (3)
O1	0.10795 (7)	0.40790 (11)	0.50401 (5)	0.0615 (3)
O2	0.17058 (8)	0.61823 (10)	0.47356 (5)	0.0634 (3)
O3	0.09238 (7)	0.68272 (10)	0.23367 (5)	0.0606 (3)
O4	0.07382 (8)	0.61470 (13)	0.06358 (6)	0.0795 (4)
C19	0.22592 (12)	0.31667 (19)	0.17820 (10)	0.0741 (5)
H19	0.2419	0.2511	0.2050	0.089*
C20	0.27476 (11)	0.37328 (19)	0.13340 (10)	0.0747 (6)
H20	0.3309	0.3501	0.1263	0.090*
S1	0.22947 (5)	0.48657 (9)	0.09150 (7)	0.0691 (3)	0.675 (3)
C18	0.1412 (3)	0.3789 (4)	0.1768 (2)	0.0592 (17)*	0.675 (3)
H18	0.0959	0.3571	0.2036	0.071*	0.675 (3)
S1'	0.13250 (13)	0.3528 (2)	0.18931 (11)	0.0487 (5)	0.325 (3)
C18'	0.2189 (6)	0.4727 (13)	0.1078 (7)	0.160 (9)*	0.325 (3)
H18'	0.2373	0.5316	0.0778	0.192*	0.325 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0799 (12)	0.0676 (11)	0.0631 (11)	0.0014 (9)	0.0013 (9)	0.0211 (9)
C2	0.0434 (7)	0.0473 (8)	0.0434 (8)	0.0063 (6)	0.0002 (6)	0.0017 (6)
C3	0.0491 (8)	0.0439 (8)	0.0530 (9)	−0.0046 (6)	−0.0002 (7)	0.0035 (7)
C4	0.0457 (8)	0.0474 (8)	0.0481 (8)	−0.0060 (6)	−0.0023 (6)	−0.0029 (7)
C5	0.0387 (7)	0.0450 (8)	0.0420 (7)	0.0002 (6)	0.0029 (6)	−0.0017 (6)
C6	0.0409 (7)	0.0412 (7)	0.0475 (8)	−0.0024 (6)	0.0012 (6)	−0.0024 (6)
C7	0.0410 (7)	0.0457 (8)	0.0477 (8)	0.0011 (6)	−0.0031 (6)	−0.0060 (7)
C8	0.0731 (11)	0.0563 (10)	0.0713 (11)	−0.0111 (9)	−0.0122 (9)	−0.0112 (9)
C10	0.0414 (7)	0.0428 (8)	0.0455 (8)	0.0021 (6)	0.0003 (6)	0.0048 (6)
C11	0.0468 (8)	0.0665 (10)	0.0567 (9)	0.0039 (7)	0.0043 (7)	0.0047 (8)
C12	0.0392 (9)	0.0766 (12)	0.0860 (13)	0.0023 (8)	−0.0010 (8)	0.0088 (10)
C13	0.0522 (10)	0.0669 (11)	0.0801 (13)	0.0023 (8)	−0.0214 (9)	0.0003 (10)
C14	0.0617 (10)	0.0565 (10)	0.0520 (9)	0.0055 (8)	−0.0131 (8)	−0.0006 (8)
C15	0.0479 (8)	0.0403 (7)	0.0448 (8)	0.0039 (6)	−0.0027 (6)	0.0035 (6)
C16	0.0590 (9)	0.0486 (8)	0.0411 (8)	0.0023 (7)	0.0036 (7)	0.0010 (7)
C17	0.0464 (8)	0.0490 (8)	0.0438 (8)	−0.0003 (6)	0.0065 (6)	−0.0059 (7)
C9	0.0436 (7)	0.0431 (7)	0.0441 (8)	0.0003 (6)	0.0049 (6)	−0.0030 (6)
O1	0.0726 (7)	0.0614 (7)	0.0506 (6)	−0.0004 (6)	−0.0104 (5)	0.0102 (5)
O2	0.0760 (8)	0.0576 (7)	0.0565 (7)	−0.0122 (6)	−0.0208 (6)	−0.0018 (5)
O3	0.0676 (7)	0.0615 (7)	0.0527 (6)	−0.0207 (6)	0.0014 (5)	0.0064 (5)
O4	0.0883 (9)	0.0898 (9)	0.0605 (7)	0.0172 (7)	0.0181 (7)	0.0303 (7)
C19	0.0794 (13)	0.0703 (12)	0.0724 (12)	0.0139 (10)	−0.0122 (10)	−0.0096 (10)
C20	0.0453 (9)	0.0834 (13)	0.0954 (15)	0.0117 (9)	0.0010 (10)	−0.0217 (12)
S1	0.0501 (4)	0.0695 (5)	0.0876 (6)	0.0022 (3)	0.0239 (4)	−0.0130 (4)
S1'	0.0502 (9)	0.0473 (9)	0.0485 (9)	0.0120 (7)	0.0026 (7)	0.0027 (8)

Geometric parameters (Å, º) top

C1—O1	1.423 (2)	C11—H11	0.9300
C1—H1A	0.9600	C12—C13	1.370 (3)
C1—H1B	0.9600	C12—H12	0.9300
C1—H1C	0.9600	C13—C14	1.378 (2)
C2—O1	1.3544 (17)	C13—H13	0.9300
C2—C3	1.377 (2)	C14—C15	1.391 (2)
C2—C7	1.411 (2)	C14—H14	0.9300
C3—C4	1.383 (2)	C15—C16	1.495 (2)
C3—H3	0.9300	C16—O4	1.2191 (18)
C4—C5	1.388 (2)	C16—C17	1.460 (2)
C4—H4	0.9300	C17—C18	1.345 (4)
C5—C6	1.4034 (19)	C17—C18'	1.366 (9)
C5—C9	1.4756 (19)	C17—S1	1.6709 (17)
C6—C7	1.370 (2)	C17—S1'	1.728 (3)
C6—H6	0.9300	C9—O3	1.2225 (16)
C7—O2	1.3625 (17)	C19—C20	1.344 (3)
C8—O2	1.415 (2)	C19—C18	1.493 (5)
C8—H8A	0.9600	C19—S1'	1.538 (3)
C8—H8B	0.9600	C19—H19	0.9300
C8—H8C	0.9600	C20—C18'	1.483 (10)
C10—C11	1.391 (2)	C20—S1	1.656 (2)
C10—C15	1.3979 (19)	C20—H20	0.9300
C10—C9	1.501 (2)	C18—H18	0.9300
C11—C12	1.382 (2)	C18'—H18'	0.9300

O1—C1—H1A	109.5	C13—C14—H14	119.7
O1—C1—H1B	109.5	C15—C14—H14	119.7
H1A—C1—H1B	109.5	C14—C15—C10	119.35 (14)
O1—C1—H1C	109.5	C14—C15—C16	116.43 (13)
H1A—C1—H1C	109.5	C10—C15—C16	124.22 (13)
H1B—C1—H1C	109.5	O4—C16—C17	120.68 (14)
O1—C2—C3	125.24 (14)	O4—C16—C15	119.11 (14)
O1—C2—C7	115.09 (13)	C17—C16—C15	119.99 (13)
C3—C2—C7	119.67 (13)	C18—C17—C18'	103.3 (6)
C2—C3—C4	120.10 (14)	C18—C17—C16	130.5 (2)
C2—C3—H3	120.0	C18'—C17—C16	126.3 (5)
C4—C3—H3	120.0	C18—C17—S1	112.7 (2)
C3—C4—C5	120.85 (13)	C18'—C17—S1	10.0 (5)
C3—C4—H4	119.6	C16—C17—S1	116.69 (11)
C5—C4—H4	119.6	C18—C17—S1'	5.0 (3)
C4—C5—C6	119.02 (13)	C18'—C17—S1'	108.0 (5)
C4—C5—C9	122.54 (13)	C16—C17—S1'	125.64 (12)
C6—C5—C9	118.33 (12)	S1—C17—S1'	117.35 (12)
C7—C6—C5	120.35 (13)	O3—C9—C5	121.81 (13)
C7—C6—H6	119.8	O3—C9—C10	118.66 (13)
C5—C6—H6	119.8	C5—C9—C10	119.52 (12)
O2—C7—C6	125.38 (13)	C2—O1—C1	117.90 (13)
O2—C7—C2	114.62 (13)	C7—O2—C8	117.72 (12)
C6—C7—C2	120.00 (13)	C20—C19—C18	107.0 (2)
O2—C8—H8A	109.5	C20—C19—S1'	122.1 (2)
O2—C8—H8B	109.5	C18—C19—S1'	15.25 (19)
H8A—C8—H8B	109.5	C20—C19—H19	126.5
O2—C8—H8C	109.5	C18—C19—H19	126.5
H8A—C8—H8C	109.5	S1'—C19—H19	111.3
H8B—C8—H8C	109.5	C19—C20—C18'	103.4 (4)
C11—C10—C15	119.17 (14)	C19—C20—S1	116.37 (14)
C11—C10—C9	119.58 (13)	C18'—C20—S1	13.3 (4)
C15—C10—C9	120.83 (13)	C19—C20—H20	121.8
C12—C11—C10	120.58 (16)	C18'—C20—H20	134.6
C12—C11—H11	119.7	S1—C20—H20	121.8
C10—C11—H11	119.7	C20—S1—C17	91.91 (11)
C13—C12—C11	120.11 (16)	C17—C18—C19	112.0 (3)
C13—C12—H12	119.9	C17—C18—H18	124.0
C11—C12—H12	119.9	C19—C18—H18	124.0
C12—C13—C14	120.26 (16)	C19—S1'—C17	92.13 (16)
C12—C13—H13	119.9	C17—C18'—C20	114.1 (8)
C14—C13—H13	119.9	C17—C18'—H18'	123.0
C13—C14—C15	120.52 (16)	C20—C18'—H18'	123.0

O1—C2—C3—C4	179.55 (13)	C4—C5—C9—C10	21.6 (2)
C7—C2—C3—C4	−0.3 (2)	C6—C5—C9—C10	−162.15 (12)
C2—C3—C4—C5	0.6 (2)	C11—C10—C9—O3	−131.30 (15)
C3—C4—C5—C6	0.1 (2)	C15—C10—C9—O3	41.2 (2)
C3—C4—C5—C9	176.30 (13)	C11—C10—C9—C5	47.76 (19)
C4—C5—C6—C7	−1.1 (2)	C15—C10—C9—C5	−139.72 (14)
C9—C5—C6—C7	−177.44 (12)	C3—C2—O1—C1	−0.8 (2)
C5—C6—C7—O2	−179.37 (13)	C7—C2—O1—C1	179.09 (14)
C5—C6—C7—C2	1.3 (2)	C6—C7—O2—C8	3.2 (2)
O1—C2—C7—O2	0.10 (18)	C2—C7—O2—C8	−177.42 (14)
C3—C2—C7—O2	179.99 (13)	C18—C19—C20—C18'	2.3 (7)
O1—C2—C7—C6	179.46 (12)	S1'—C19—C20—C18'	4.5 (7)
C3—C2—C7—C6	−0.6 (2)	C18—C19—C20—S1	−1.0 (3)
C15—C10—C11—C12	−0.7 (2)	S1'—C19—C20—S1	1.2 (3)
C9—C10—C11—C12	171.96 (15)	C19—C20—S1—C17	1.00 (17)
C10—C11—C12—C13	0.9 (3)	C18'—C20—S1—C17	−13 (3)
C11—C12—C13—C14	−0.3 (3)	C18—C17—S1—C20	−0.7 (3)
C12—C13—C14—C15	−0.4 (3)	C18'—C17—S1—C20	19 (4)
C13—C14—C15—C10	0.5 (2)	C16—C17—S1—C20	−176.59 (13)
C13—C14—C15—C16	−178.31 (15)	S1'—C17—S1—C20	−2.63 (14)
C11—C10—C15—C14	0.0 (2)	C18'—C17—C18—C19	−3.2 (8)
C9—C10—C15—C14	−172.56 (13)	C16—C17—C18—C19	175.46 (19)
C11—C10—C15—C16	178.76 (14)	S1—C17—C18—C19	0.3 (4)
C9—C10—C15—C16	6.2 (2)	S1'—C17—C18—C19	160 (3)
C14—C15—C16—O4	50.8 (2)	C20—C19—C18—C17	0.4 (4)
C10—C15—C16—O4	−127.95 (17)	S1'—C19—C18—C17	−172.7 (12)
C14—C15—C16—C17	−123.81 (15)	C20—C19—S1'—C17	−2.5 (2)
C10—C15—C16—C17	57.4 (2)	C18—C19—S1'—C17	5.3 (9)
O4—C16—C17—C18	−169.2 (3)	C18—C17—S1'—C19	−18 (3)
C15—C16—C17—C18	5.4 (4)	C18'—C17—S1'—C19	−0.7 (8)
O4—C16—C17—C18'	9.2 (9)	C16—C17—S1'—C19	176.50 (15)
C15—C16—C17—C18'	−176.3 (9)	S1—C17—S1'—C19	3.15 (16)
O4—C16—C17—S1	5.9 (2)	C18—C17—C18'—C20	4.8 (13)
C15—C16—C17—S1	−179.57 (11)	C16—C17—C18'—C20	−173.9 (6)
O4—C16—C17—S1'	−167.53 (16)	S1—C17—C18'—C20	−157 (5)
C15—C16—C17—S1'	7.0 (2)	S1'—C17—C18'—C20	3.3 (13)
C4—C5—C9—O3	−159.37 (14)	C19—C20—C18'—C17	−4.7 (13)
C6—C5—C9—O3	16.9 (2)	S1—C20—C18'—C17	162 (4)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C17/C19/C20/S1'/C18' ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O4ⁱ	0.93	2.58	3.496 (2)	169
C1—H1A···Cg2ⁱⁱ	0.96	2.99	3.799 (3)	143

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₆O₄S
M_r	352.40
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	15.7324 (6), 10.7988 (5), 20.4877 (11)
V (Å³)	3480.7 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.25 × 0.22 × 0.19

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.950, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	22015, 4469, 2968
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.674

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.107, 1.03
No. of reflections	4469
No. of parameters	236
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.20

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

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C17/C19/C20/S1'/C18' ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O4ⁱ	0.93	2.58	3.496 (2)	169.0
C1—H1A···Cg2ⁱⁱ	0.96	2.99	3.799 (3)	143

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

Acknowledgements

The authors thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.

References

Asiri, A. M., Khan, S. A. & Tahir, M. N. (2010). Acta Cryst. E66, o2358. Web of Science CSD CrossRef IUCr Journals Google Scholar
Aslam, M., Anis, I., Afza, N., Nelofar, A. & Yousuf, S. (2011). Acta Cryst. E67, o3215. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bonini, C., Chiummiento, L., Bonis, M. D., Funicello, M., Lupattelli, P., Suanno, G., Berti, F. & Campaner, P. (2005). Tetrahedron, 61, 6580–6583. Web of Science CrossRef CAS Google Scholar
Brault, L., Migianu, E., Neguesque, A., Battaglia, E., Bagrel, D. & Kirsch, G. (2005). Eur. J. Med. Chem. 40, 757–760. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Isloora, A. M., Kalluraya, B. & Sridhar Pai, K. (2010). Eur. J. Med. Chem. 45, 825–830. Web of Science PubMed Google Scholar
Khan, K. M., Khan, M., Ali, M., Taha, M., Rasheed, S., Perveen, S. & Choudhary, M. I. (2009). Bioorg. Med. Chem. 17, 7795–7801. Web of Science CrossRef PubMed CAS 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
Xia, G.-M., Ji, M.-W., Lu, P., Sun, G.-X. & Xu, W.-F. (2010). Acta Cryst. E66, o148. Web of Science CSD CrossRef IUCr Journals Google Scholar