1-[2,2-Bis(phenyl­sulfon­yl)ethen­yl]-4-meth­oxy­benzene

Asahara, H.; Mayer, P.; Mayr, H.

doi:10.1107/S1600536812001961

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o470

doi:10.1107/S1600536812001961

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1-[2,2-Bis(phenylsulfonyl)ethenyl]-4-methoxybenzene

Haruyasu Asahara,^a Peter Mayer ^a ^* and Herbert Mayr ^a

^aLudwig-Maximilians-Universität, Department of Chemistry, Butenandtstrasse 5–13, 81377 München, Germany
^*Correspondence e-mail: p.mayer@lmu.de

(Received 16 December 2011; accepted 16 January 2012; online 21 January 2012)

In the title compound, C₂₁H₁₈O₅S₂, the two sulfur-bound phenyl rings lie on opposite sides of the methoxyphenyl group, making dihedral angles of 77.58 (8) and 87.45 (8)°with it. The dihedral angle between the sulfur-bound phenyl rings is 57.31 (8)°. In the crystal, π–π stacking is observed between the two sulfur-bound phenyl rings, with a centroid–centroid distance of 3.878 (1) Å and a dihedral angle of 7.58 (8)°. The molecules are linked by weak C—H⋯O and C—H⋯π contacts.

Related literature

For background to bissulfonyl ethylenes and their synthesis, see: Simpkins (1993 ); Najera & Yus (1999 ); Prilezhaeva (2000 ); Nielsen et al. (2010 ), Zhu & Lu (2009 ), Alba et al. (2010 ), Sulzer-Moss et al. (2009 ). For a related structure, see: De Lucchi et al. (1985 ).

Experimental

Crystal data

C₂₁H₁₈O₅S₂
M_r = 414.50
Monoclinic, P 2₁ /c
a = 7.8291 (1) Å
b = 21.6666 (4) Å
c = 12.0332 (2) Å
β = 107.8449 (10)°
V = 1942.99 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 173 K
0.33 × 0.26 × 0.21 mm

Data collection

Nonius KappaCCD diffractometer
15675 measured reflections
4445 independent reflections
3908 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.084
S = 1.08
4445 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C16–C21 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯Cg1ⁱ	0.95	2.56	3.4835 (17)	164
C14—H14⋯O1ⁱⁱ	0.95	2.51	3.229 (2)	133
C21—H21⋯O3ⁱ	0.95	2.50	3.2695 (19)	138
C20—H20⋯O4ⁱⁱⁱ	0.95	2.59	3.453 (2)	151
Symmetry codes: (i) -x, -y, -z+1; (ii) x+1, y, z; (iii) x-1, y, z.

Data collection: COLLECT (Hooft, 2004 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812001961/zj2048sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812001961/zj2048Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812001961/zj2048Isup3.cml

checkCIF report

Comment top

Bissulfonyl ethylenes are important reagents in synthetic organic chemistry, because they are active Michael acceptors [Simpkins (1993), Najera et al. (1999), Prilezhaeva (2000)]. Recently, organocatalytic Michael additions of bissulfonyl ethylene have also been reported [Nielsen et al. (2010), Zhu et al. (2009), Alba et al. (2010)]. During our studies on the electrophilic reactivity of bissulfonyl ethylenes, we discussed structure-reactivity relationships.

In the title compound, the C1—C2 double bond deviates only slighthly from coplanarity with the phenyl ring of the methoxyphenyl group (plane-bond angle 10.22 (10)°). The double bonds S1—O2 and S2—O3 are coplanar with the C1—C2 double bond as is indicated by the torsion angles O2—S1—C1—C2 (-178.13 (13)°) and O3—S2—C1—C2 (1.12 (13)°). The sulfur-bound phenyl rings lie to opposite sides of the methoxyphenyl group with dihedral angles of 77.58 (8)° and 87.45 (8)°. The ring bound to S1 is almost coplanar with the S1—O1 double bond (plane-bond angle 7.79 (8)°), the ring bound to S2 is nearly coplanar with the S2—O4 double bond (plane-bond angle 9.12 (7)°). The molecular structure of the title compound is shown in Figure 1.

The packing of the title compound is shown in Figure 2. π-π-stacking is observed between the two sulfur-bound phenyl rings with a centroid-centroid distance of 3.878 (1) Å and a dihedral angle of 7.58 (8)°. A C–H···π contact is established between the phenyl ring bound to S2 and the C8–H8 moiety. The distance of H8 to the centre of gravity of the phenyl ring is 2.56 Å, the angle around H8 is 164°. Furthermore weak C–H···O contacts with sulfur-bound oxygen atoms as acceptors are observed.

Related literature top

For background to bissulfonyl ethylenes and their synthesis, see: Simpkins (1993); Najera & Yus (1999); Prilezhaeva (2000); Nielsen et al. (2010), Zhu & Lu (2009), Alba et al. (2010), Sulzer-Moss et al. (2009). For a related structure, see: De Lucchi et al. (1985).

Experimental top

The title compound has been obtained by following modified method of Alexakis [Sulzer-Moss et al. (2009)]. A mixture of p-anisaldehyde (15.0 g, 110 mmol, 7.4 equiv.), bis(phenylsulfonyl)methane (4.4 g, 14.8 mmol, 1.0 equiv.), diethylammonium chloride (32.1 mmol, 2.1 equiv.) and potassium fluoride (2.5 mmol, 0.17 equiv.) in dry toluene (150 ml) was stirred and refluxed under a Dean Stark water separator for 24 h. After cooling, the solvent was evaporated and residue was partitioned between water (50 ml) and CH₂Cl₂ (150 ml). The organic phase was separated and the aqueous phase was extracted with CH₂Cl₂ (three times 25 ml). The combined organic layer was dried over Na₂SO₄, filtered and concentrated under reduced pressure. The crude mixture was purified by flash column chromatography on silica gel (pentane/ethyl acetate: from 95/5 to 80/20), followed by recrystallization from pentane/chloroform. mp 123.0–123.9 °C (yield 4.9 g, 11.8 mmol, 79.9%).

Computing details top

Data collection: COLLECT (Hooft, 2004); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level) for non-H atoms.
	Fig. 2. The packing of the title compound.

1-[2,2-bis(phenylsulfonyl)ethenyl]-4-methoxybenzene top

Crystal data top

C₂₁H₁₈O₅S₂	F(000) = 864
M_r = 414.50	D_x = 1.417 (1) Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7909 reflections
a = 7.8291 (1) Å	θ = 3.1–27.5°
b = 21.6666 (4) Å	µ = 0.31 mm⁻¹
c = 12.0332 (2) Å	T = 173 K
β = 107.8449 (10)°	Block, yellow
V = 1942.99 (5) Å³	0.33 × 0.26 × 0.21 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	3908 reflections with I > 2σ(I)
Radiation source: rotating anode	R_int = 0.026
MONTEL, graded multilayered X-ray optics monochromator	θ_max = 27.5°, θ_min = 3.3°
CCD; rotation images; thick slices scans	h = −10→10
15675 measured reflections	k = −27→28
4445 independent reflections	l = −15→15

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.031P)² + 1.0861P] where P = (F_o² + 2F_c²)/3
4445 reflections	(Δ/σ)_max < 0.001
254 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₂₁H₁₈O₅S₂	V = 1942.99 (5) Å³
M_r = 414.50	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.8291 (1) Å	µ = 0.31 mm⁻¹
b = 21.6666 (4) Å	T = 173 K
c = 12.0332 (2) Å	0.33 × 0.26 × 0.21 mm
β = 107.8449 (10)°

Data collection top

Nonius KappaCCD diffractometer	3908 reflections with I > 2σ(I)
15675 measured reflections	R_int = 0.026
4445 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.084	H-atom parameters constrained
S = 1.08	Δρ_max = 0.33 e Å⁻³
4445 reflections	Δρ_min = −0.38 e Å⁻³
254 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 > 2σ(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	0.20814 (5)	0.197024 (16)	0.62810 (3)	0.02090 (9)
S2	0.18614 (5)	0.089334 (17)	0.46455 (3)	0.02332 (10)
O1	0.07863 (14)	0.21777 (5)	0.68234 (10)	0.0292 (2)
O2	0.20435 (14)	0.22512 (5)	0.51907 (9)	0.0278 (2)
O3	0.17420 (16)	0.02302 (5)	0.46677 (9)	0.0313 (3)
O4	0.33662 (14)	0.11588 (5)	0.43740 (9)	0.0305 (3)
O5	0.25877 (18)	0.04667 (6)	1.16063 (9)	0.0365 (3)
C1	0.18455 (19)	0.11624 (7)	0.60485 (12)	0.0214 (3)
C2	0.1764 (2)	0.07226 (7)	0.68278 (13)	0.0245 (3)
H2	0.1564	0.0325	0.6481	0.029*
C3	0.1902 (2)	0.07015 (7)	0.80624 (12)	0.0242 (3)
C4	0.18860 (19)	0.12011 (7)	0.88083 (13)	0.0243 (3)
H4	0.1734	0.1609	0.8506	0.029*
C5	0.2090 (2)	0.11019 (7)	0.99738 (13)	0.0276 (3)
H5	0.2058	0.1443	1.0464	0.033*
C6	0.2341 (2)	0.05075 (7)	1.04444 (13)	0.0274 (3)
C7	0.2320 (2)	0.00049 (8)	0.97225 (14)	0.0338 (4)
H7	0.2464	−0.0403	1.0027	0.041*
C8	0.2085 (2)	0.01103 (7)	0.85489 (14)	0.0322 (4)
H8	0.2045	−0.0234	0.8054	0.039*
C9	0.2945 (3)	−0.01316 (9)	1.21382 (15)	0.0435 (4)
H9A	0.1915	−0.0403	1.1800	0.065*
H9B	0.3150	−0.0094	1.2981	0.065*
H9C	0.4014	−0.0307	1.1998	0.065*
C10	0.42503 (19)	0.20496 (7)	0.72786 (13)	0.0227 (3)
C11	0.4505 (2)	0.23657 (7)	0.83213 (13)	0.0284 (3)
H11	0.3517	0.2532	0.8523	0.034*
C12	0.6252 (2)	0.24312 (8)	0.90616 (14)	0.0365 (4)
H12	0.6463	0.2645	0.9780	0.044*
C13	0.7677 (2)	0.21894 (9)	0.87638 (15)	0.0394 (4)
H13	0.8863	0.2241	0.9275	0.047*
C14	0.7396 (2)	0.18709 (9)	0.77248 (16)	0.0368 (4)
H14	0.8387	0.1701	0.7531	0.044*
C15	0.5677 (2)	0.17990 (8)	0.69699 (14)	0.0283 (3)
H15	0.5474	0.1583	0.6254	0.034*
C16	−0.0154 (2)	0.11649 (7)	0.36510 (12)	0.0231 (3)
C17	−0.0075 (2)	0.14543 (7)	0.26401 (13)	0.0298 (3)
H17	0.1047	0.1546	0.2526	0.036*
C18	−0.1677 (2)	0.16064 (8)	0.17987 (14)	0.0361 (4)
H18	−0.1656	0.1801	0.1096	0.043*
C19	−0.3298 (2)	0.14774 (8)	0.19744 (15)	0.0355 (4)
H19	−0.4383	0.1582	0.1390	0.043*
C20	−0.3363 (2)	0.11958 (8)	0.29952 (15)	0.0323 (4)
H20	−0.4487	0.1113	0.3112	0.039*
C21	−0.1780 (2)	0.10357 (7)	0.38461 (14)	0.0270 (3)
H21	−0.1806	0.0842	0.4549	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01895 (17)	0.02019 (17)	0.02280 (18)	0.00109 (13)	0.00526 (13)	0.00185 (13)
S2	0.02724 (19)	0.02359 (19)	0.01953 (17)	0.00020 (14)	0.00776 (14)	0.00026 (13)
O1	0.0256 (5)	0.0272 (6)	0.0373 (6)	0.0061 (4)	0.0134 (5)	0.0010 (5)
O2	0.0302 (6)	0.0260 (6)	0.0252 (5)	0.0007 (4)	0.0054 (4)	0.0073 (4)
O3	0.0453 (7)	0.0237 (6)	0.0250 (5)	0.0030 (5)	0.0112 (5)	−0.0005 (4)
O4	0.0279 (6)	0.0390 (7)	0.0275 (6)	−0.0007 (5)	0.0125 (5)	0.0005 (5)
O5	0.0530 (7)	0.0367 (7)	0.0210 (5)	0.0024 (6)	0.0133 (5)	0.0005 (5)
C1	0.0213 (7)	0.0219 (7)	0.0204 (6)	−0.0013 (5)	0.0056 (5)	−0.0011 (5)
C2	0.0267 (7)	0.0229 (7)	0.0231 (7)	−0.0024 (6)	0.0062 (6)	−0.0017 (6)
C3	0.0261 (7)	0.0244 (7)	0.0218 (7)	−0.0024 (6)	0.0069 (6)	−0.0006 (6)
C4	0.0240 (7)	0.0232 (7)	0.0261 (7)	−0.0021 (6)	0.0082 (6)	0.0002 (6)
C5	0.0305 (8)	0.0274 (8)	0.0260 (7)	−0.0012 (6)	0.0102 (6)	−0.0053 (6)
C6	0.0297 (8)	0.0334 (8)	0.0198 (7)	−0.0022 (6)	0.0085 (6)	−0.0004 (6)
C7	0.0511 (10)	0.0261 (8)	0.0255 (8)	0.0004 (7)	0.0139 (7)	0.0027 (6)
C8	0.0503 (10)	0.0233 (8)	0.0247 (8)	−0.0026 (7)	0.0138 (7)	−0.0033 (6)
C9	0.0634 (12)	0.0432 (11)	0.0268 (8)	0.0097 (9)	0.0180 (8)	0.0097 (7)
C10	0.0209 (7)	0.0218 (7)	0.0241 (7)	−0.0031 (5)	0.0046 (5)	0.0024 (5)
C11	0.0342 (8)	0.0242 (8)	0.0261 (7)	−0.0037 (6)	0.0080 (6)	0.0004 (6)
C12	0.0448 (10)	0.0330 (9)	0.0248 (8)	−0.0110 (8)	0.0005 (7)	0.0012 (7)
C13	0.0305 (9)	0.0432 (10)	0.0349 (9)	−0.0134 (7)	−0.0039 (7)	0.0104 (8)
C14	0.0220 (8)	0.0451 (10)	0.0419 (10)	−0.0015 (7)	0.0077 (7)	0.0094 (8)
C15	0.0234 (7)	0.0325 (8)	0.0289 (8)	−0.0020 (6)	0.0079 (6)	0.0013 (6)
C16	0.0272 (7)	0.0200 (7)	0.0202 (7)	−0.0025 (6)	0.0047 (6)	−0.0018 (5)
C17	0.0345 (8)	0.0296 (8)	0.0243 (7)	−0.0056 (7)	0.0076 (6)	0.0028 (6)
C18	0.0448 (10)	0.0343 (9)	0.0237 (8)	−0.0024 (7)	0.0022 (7)	0.0053 (6)
C19	0.0344 (9)	0.0308 (9)	0.0324 (8)	0.0027 (7)	−0.0030 (7)	−0.0033 (7)
C20	0.0280 (8)	0.0289 (8)	0.0386 (9)	−0.0007 (6)	0.0082 (7)	−0.0083 (7)
C21	0.0313 (8)	0.0233 (7)	0.0273 (7)	−0.0020 (6)	0.0105 (6)	−0.0024 (6)

Geometric parameters (Å, º) top

S1—O1	1.4359 (11)	C9—H9B	0.9800
S1—O2	1.4383 (11)	C9—H9C	0.9800
S1—C10	1.7620 (15)	C10—C11	1.389 (2)
S1—C1	1.7731 (15)	C10—C15	1.391 (2)
S2—O4	1.4357 (11)	C11—C12	1.392 (2)
S2—O3	1.4405 (12)	C11—H11	0.9500
S2—C16	1.7638 (15)	C12—C13	1.375 (3)
S2—C1	1.7897 (14)	C12—H12	0.9500
O5—C6	1.3544 (18)	C13—C14	1.385 (3)
O5—C9	1.435 (2)	C13—H13	0.9500
C1—C2	1.352 (2)	C14—C15	1.382 (2)
C2—C3	1.457 (2)	C14—H14	0.9500
C2—H2	0.9500	C15—H15	0.9500
C3—C8	1.397 (2)	C16—C17	1.387 (2)
C3—C4	1.409 (2)	C16—C21	1.392 (2)
C4—C5	1.379 (2)	C17—C18	1.389 (2)
C4—H4	0.9500	C17—H17	0.9500
C5—C6	1.396 (2)	C18—C19	1.377 (3)
C5—H5	0.9500	C18—H18	0.9500
C6—C7	1.390 (2)	C19—C20	1.386 (2)
C7—C8	1.386 (2)	C19—H19	0.9500
C7—H7	0.9500	C20—C21	1.388 (2)
C8—H8	0.9500	C20—H20	0.9500
C9—H9A	0.9800	C21—H21	0.9500

O1—S1—O2	117.52 (7)	O5—C9—H9C	109.5
O1—S1—C10	109.09 (7)	H9A—C9—H9C	109.5
O2—S1—C10	109.05 (7)	H9B—C9—H9C	109.5
O1—S1—C1	109.08 (7)	C11—C10—C15	121.94 (14)
O2—S1—C1	107.57 (7)	C11—C10—S1	120.33 (12)
C10—S1—C1	103.64 (7)	C15—C10—S1	117.71 (11)
O4—S2—O3	117.79 (7)	C10—C11—C12	117.97 (15)
O4—S2—C16	109.75 (7)	C10—C11—H11	121.0
O3—S2—C16	107.20 (7)	C12—C11—H11	121.0
O4—S2—C1	109.11 (7)	C13—C12—C11	120.72 (16)
O3—S2—C1	106.75 (7)	C13—C12—H12	119.6
C16—S2—C1	105.54 (7)	C11—C12—H12	119.6
C6—O5—C9	117.78 (13)	C12—C13—C14	120.50 (15)
C2—C1—S1	127.66 (11)	C12—C13—H13	119.8
C2—C1—S2	116.11 (11)	C14—C13—H13	119.8
S1—C1—S2	116.10 (8)	C15—C14—C13	120.17 (17)
C1—C2—C3	136.46 (14)	C15—C14—H14	119.9
C1—C2—H2	111.8	C13—C14—H14	119.9
C3—C2—H2	111.8	C14—C15—C10	118.70 (15)
C8—C3—C4	117.20 (14)	C14—C15—H15	120.7
C8—C3—C2	114.97 (14)	C10—C15—H15	120.7
C4—C3—C2	127.82 (14)	C17—C16—C21	121.88 (14)
C5—C4—C3	120.49 (14)	C17—C16—S2	118.33 (12)
C5—C4—H4	119.8	C21—C16—S2	119.53 (11)
C3—C4—H4	119.8	C16—C17—C18	118.24 (15)
C4—C5—C6	120.95 (14)	C16—C17—H17	120.9
C4—C5—H5	119.5	C18—C17—H17	120.9
C6—C5—H5	119.5	C19—C18—C17	120.58 (16)
O5—C6—C7	124.39 (15)	C19—C18—H18	119.7
O5—C6—C5	115.88 (14)	C17—C18—H18	119.7
C7—C6—C5	119.73 (14)	C18—C19—C20	120.75 (15)
C8—C7—C6	118.70 (15)	C18—C19—H19	119.6
C8—C7—H7	120.7	C20—C19—H19	119.6
C6—C7—H7	120.7	C19—C20—C21	119.75 (16)
C7—C8—C3	122.86 (15)	C19—C20—H20	120.1
C7—C8—H8	118.6	C21—C20—H20	120.1
C3—C8—H8	118.6	C20—C21—C16	118.78 (15)
O5—C9—H9A	109.5	C20—C21—H21	120.6
O5—C9—H9B	109.5	C16—C21—H21	120.6
H9A—C9—H9B	109.5

O1—S1—C1—C2	−49.65 (15)	O1—S1—C10—C11	−9.58 (14)
O2—S1—C1—C2	−178.13 (13)	O2—S1—C10—C11	119.97 (12)
C10—S1—C1—C2	66.46 (15)	C1—S1—C10—C11	−125.68 (12)
O1—S1—C1—S2	134.70 (8)	O1—S1—C10—C15	171.88 (12)
O2—S1—C1—S2	6.22 (10)	O2—S1—C10—C15	−58.57 (13)
C10—S1—C1—S2	−109.19 (9)	C1—S1—C10—C15	55.78 (13)
O4—S2—C1—C2	−127.17 (12)	C15—C10—C11—C12	0.4 (2)
O3—S2—C1—C2	1.12 (13)	S1—C10—C11—C12	−178.05 (12)
C16—S2—C1—C2	114.95 (12)	C10—C11—C12—C13	0.0 (2)
O4—S2—C1—S1	49.00 (10)	C11—C12—C13—C14	−0.6 (3)
O3—S2—C1—S1	177.29 (8)	C12—C13—C14—C15	0.7 (3)
C16—S2—C1—S1	−68.88 (9)	C13—C14—C15—C10	−0.3 (3)
S1—C1—C2—C3	−3.5 (3)	C11—C10—C15—C14	−0.3 (2)
S2—C1—C2—C3	172.18 (15)	S1—C10—C15—C14	178.21 (12)
C1—C2—C3—C8	−167.66 (18)	O4—S2—C16—C17	14.62 (14)
C1—C2—C3—C4	11.9 (3)	O3—S2—C16—C17	−114.41 (12)
C8—C3—C4—C5	1.6 (2)	C1—S2—C16—C17	132.07 (12)
C2—C3—C4—C5	−177.91 (14)	O4—S2—C16—C21	−171.11 (12)
C3—C4—C5—C6	0.9 (2)	O3—S2—C16—C21	59.86 (13)
C9—O5—C6—C7	3.5 (2)	C1—S2—C16—C21	−53.66 (13)
C9—O5—C6—C5	−176.81 (16)	C21—C16—C17—C18	−1.1 (2)
C4—C5—C6—O5	177.80 (14)	S2—C16—C17—C18	172.98 (13)
C4—C5—C6—C7	−2.4 (2)	C16—C17—C18—C19	0.6 (3)
O5—C6—C7—C8	−178.93 (16)	C17—C18—C19—C20	0.3 (3)
C5—C6—C7—C8	1.3 (3)	C18—C19—C20—C21	−0.7 (2)
C6—C7—C8—C3	1.3 (3)	C19—C20—C21—C16	0.2 (2)
C4—C3—C8—C7	−2.8 (3)	C17—C16—C21—C20	0.8 (2)
C2—C3—C8—C7	176.83 (16)	S2—C16—C21—C20	−173.31 (12)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C16–C21 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Cg1ⁱ	0.95	2.56	3.4835 (17)	164
C14—H14···O1ⁱⁱ	0.95	2.51	3.229 (2)	133
C21—H21···O3ⁱ	0.95	2.50	3.2695 (19)	138
C20—H20···O4ⁱⁱⁱ	0.95	2.59	3.453 (2)	151

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₈O₅S₂
M_r	414.50
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	7.8291 (1), 21.6666 (4), 12.0332 (2)
β (°)	107.8449 (10)
V (Å³)	1942.99 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.33 × 0.26 × 0.21

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	15675, 4445, 3908
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.084, 1.08
No. of reflections	4445
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.38

Computer programs: COLLECT (Hooft, 2004), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C16–C21 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Cg1ⁱ	0.95	2.56	3.4835 (17)	164
C14—H14···O1ⁱⁱ	0.95	2.51	3.229 (2)	133
C21—H21···O3ⁱ	0.95	2.50	3.2695 (19)	138
C20—H20···O4ⁱⁱⁱ	0.95	2.59	3.453 (2)	151

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

Acknowledgements

The authors thank Professor Peter Klüfers for generous allocation of diffractometer time.

References

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