1-[2,2-Bis(phenyl-sulfon-yl)ethen-yl]-4-meth-oxy-benzene.

In the title compound, C(21)H(18)O(5)S(2), the two sulfur-bound phenyl rings lie on opposite sides of the meth-oxy-phenyl 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 mol-ecules 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 = 414.50

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.084

S = 1.08

4445 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.38 e Å−3

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812001961/zj2048sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812001961/zj2048Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H18O5S2	F(000) = 864
Mr = 414.50	Dx = 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

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

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(Fo2) + (0.031P)2 + 1.0861P] where P = (Fo2 + 2Fc2)/3
4445 reflections	(Δ/σ)max < 0.001
254 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) ; (iii) .