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

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

doi:10.1107/S1600536812001961

Volume 68
Part 2
Page o470
February 2012

Received 16 December 2011
Accepted 16 January 2012
Online 21 January 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.002 Å
R = 0.033
wR = 0.084
Data-to-parameter ratio = 17.5
Details

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

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, [pi] - [pi] 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-HO and C-H [pi] 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
= 107.8449 (10)°
V = 1942.99 (5) Å³
Z = 4
Mo K radiation
= 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 > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.033
wR(F²) = 0.084
S = 1.08
4445 reflections
254 parameters
H-atom parameters constrained
_max = 0.33 e Å^-3
_min = -0.38 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C16-C21 ring.

D-HA	D-H	HA	DA	D-HA
C8-H8Cg1ⁱ	0.95	2.56	3.4835 (17)	164
C14-H14O1ⁱⁱ	0.95	2.51	3.229 (2)	133
C21-H21O3ⁱ	0.95	2.50	3.2695 (19)	138
C20-H20O4ⁱⁱⁱ	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).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZJ2048 ).

Acknowledgements

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

References

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