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Acta Crystallogr Sect E Struct Rep Online. 2010 May 1; 66(Pt 5): o1143.
Published online 2010 April 24. doi:  10.1107/S160053681001281X
PMCID: PMC2979264

(E)-1,2-Diphenyl­ethenyl methane­sulfonate

Abstract

In the title compound, C15H14O3S, the dihedral angle between the two benzene rings is 59.3 (8)°. The crystal structure is stabilized by weak inter­molecular C—H(...)π inter­actions between the benzene rings and the central ethyl­ene bridge, and a weak non-classical C—H(...)O hydrogen bond occurs in the structure.

Related literature

For general background to the design and synthesis of vinyl sulfonate derivatives, see: Limmert et al. (2005 [triangle]). For related structures, see: Cui et al. (2009 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

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Object name is e-66-o1143-scheme1.jpg

Experimental

Crystal data

  • C15H14O3S
  • M r = 274.33
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1143-efi1.jpg
  • a = 8.3789 (3) Å
  • b = 11.1397 (4) Å
  • c = 14.8365 (5) Å
  • V = 1384.82 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.23 mm−1
  • T = 296 K
  • 0.41 × 0.39 × 0.29 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.887, T max = 0.934
  • 13673 measured reflections
  • 3163 independent reflections
  • 2606 reflections with F 2 > 2.0σ(F 2)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.032
  • wR(F 2) = 0.092
  • S = 1.00
  • 3163 reflections
  • 174 parameters
  • H-atom parameters constrained
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.20 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1341 Friedel Pairs
  • Flack parameter: −0.03 (7)

Data collection: PROCESS-AUTO (Rigaku, 2006 [triangle]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007 [triangle]); program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: CrystalStructure (Rigaku Americas, 2007 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681001281X/bq2190sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001281X/bq2190Isup2.hkl

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

Acknowledgments

Mr Jianming Gu of the X-ray crystallography facility of Zhejiang University is acknowledged for assistance with the crystal structure analysis.

supplementary crystallographic information

Comment

Vinyl sulfonates, important building blocks in organic synthesis, especially as electrophiles for cross-coupling chemistry, have received much attention in recent years. These kinds of compounds are not generally stable. The title compound (I) seems to be stable by weak intermolecular interactions (Figure 2) between the benzene rings and central ethylene bridge, and also weak non-classical H bond occurs in the structure (Table 1). In (I), all bond lengths and angles are normal (Allen et al., 1987), and the dihedral angle between the two benzene rings is 59.3 (8)° (Figure 1).

Experimental

1,2-diphenylethyne and methanesulfonic acid in the presence of a catalytic amount of (Ph3P)AuNO3 (5 mol%) and phthalimide (10 mol%) in dichloroethane was stirred for 8 h at 373 K. It was quenched with saturated solution of NaHCO3 and then extracted with ethyl acetate (3 x 10 ml). The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography to give the pure product. It proceeds efficiently to form the adduct in 73% yield.

Refinement

All H atoms were placed in calculated positions, with C—H distances in the range 0.93-0.98 and included in the final cycles of refinement in the riding-model approximation, with Uiso(H) = k1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of (I) with atom labels showing the 50% probability displacement ellipsoids.
Fig. 2.
The packing of (I) viewed down the a-axis. Hydrogen bonds are shown as dashed lines. Symmetry code: (i) -0.5+x, 1.5-y, -z.

Crystal data

C15H14O3SF(000) = 576.00
Mr = 274.33Dx = 1.316 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2ac 2abCell parameters from 11138 reflections
a = 8.3789 (3) Åθ = 3.0–27.4°
b = 11.1397 (4) ŵ = 0.23 mm1
c = 14.8365 (5) ÅT = 296 K
V = 1384.82 (8) Å3Chunk, colorless
Z = 40.41 × 0.39 × 0.29 mm

Data collection

Rigaku R-AXIS RAPID diffractometer2606 reflections with F2 > 2.0σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.026
ω scansθmax = 27.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −10→10
Tmin = 0.887, Tmax = 0.934k = −13→14
13673 measured reflectionsl = −19→18
3163 independent reflections

Refinement

Refinement on F2(Δ/σ)max < 0.001
R[F2 > 2σ(F2)] = 0.032Δρmax = 0.15 e Å3
wR(F2) = 0.092Δρmin = −0.20 e Å3
S = 1.00Extinction correction: SHELXL97 (Sheldrick, 2008)
3163 reflectionsExtinction coefficient: 0.0173 (19)
174 parametersAbsolute structure: Flack (1983), 1341 Friedel Pairs
H-atom parameters constrainedFlack parameter: −0.03 (7)
w = 1/[σ2(Fo2) + (0.0507P)2 + 0.1656P] where P = (Fo2 + 2Fc2)/3

Special details

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

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

xyzUiso*/Ueq
S10.61979 (6)0.70614 (5)0.09128 (3)0.05358 (15)
O10.47962 (16)0.75814 (11)0.15261 (8)0.0510 (3)
O20.6188 (2)0.78154 (19)0.01488 (11)0.1006 (6)
O30.6001 (2)0.58046 (14)0.08152 (12)0.0874 (5)
C10.3992 (2)0.68265 (13)0.21579 (10)0.0413 (3)
C20.4741 (2)0.68403 (14)0.30602 (11)0.0426 (3)
C30.4984 (2)0.57768 (18)0.35269 (12)0.0528 (4)
C40.5742 (2)0.5788 (2)0.43570 (13)0.0720 (6)
C50.6285 (3)0.6847 (2)0.47133 (13)0.0848 (7)
C60.6049 (3)0.7911 (2)0.42591 (13)0.0842 (7)
C70.5272 (2)0.7914 (2)0.34348 (12)0.0635 (5)
C80.2696 (2)0.62793 (16)0.18488 (12)0.0462 (4)
C90.1462 (2)0.56029 (14)0.23397 (11)0.0429 (3)
C100.0528 (2)0.47874 (19)0.18648 (13)0.0553 (4)
C11−0.0714 (2)0.4185 (2)0.22810 (16)0.0649 (5)
C12−0.1058 (2)0.43858 (18)0.31661 (16)0.0612 (5)
C13−0.0169 (2)0.51958 (19)0.36462 (14)0.0608 (5)
C140.1080 (2)0.57984 (17)0.32428 (12)0.0522 (4)
C150.7899 (2)0.7341 (2)0.15510 (18)0.0714 (6)
H30.46370.50540.32820.063*
H40.58840.50750.46730.086*
H50.68150.68470.52640.102*
H60.64110.86280.45060.101*
H70.51060.86340.31320.076*
H80.25440.63310.12290.055*
H100.07410.46450.12590.066*
H11−0.13200.36370.19540.078*
H12−0.18910.39750.34430.073*
H13−0.04090.53410.42480.073*
H140.16770.63430.35780.063*
H1510.88290.71310.12080.086*
H1520.79400.81780.17050.086*
H1530.78650.68700.20920.086*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0561 (2)0.0659 (2)0.0387 (2)−0.0098 (2)0.0083 (2)−0.0016 (2)
O10.0526 (7)0.0517 (6)0.0486 (6)0.0011 (5)0.0082 (5)0.0140 (5)
O20.0944 (13)0.1520 (18)0.0553 (8)0.0003 (14)0.0209 (9)0.0421 (10)
O30.0931 (12)0.0749 (10)0.0941 (11)−0.0237 (9)0.0330 (11)−0.0417 (9)
C10.0450 (9)0.0403 (8)0.0387 (7)0.0011 (7)0.0059 (7)0.0078 (6)
C20.0409 (8)0.0484 (9)0.0384 (7)−0.0008 (7)0.0074 (6)−0.0006 (7)
C30.0595 (11)0.0550 (10)0.0437 (9)0.0102 (9)−0.0020 (8)0.0018 (8)
C40.0755 (15)0.0970 (17)0.0437 (10)0.0231 (14)−0.0026 (9)0.0089 (11)
C50.0799 (16)0.136 (2)0.0381 (9)−0.0057 (19)−0.0035 (11)−0.0126 (13)
C60.1004 (19)0.1041 (18)0.0483 (11)−0.0390 (17)0.0141 (12)−0.0247 (12)
C70.0851 (15)0.0571 (10)0.0484 (9)−0.0150 (11)0.0131 (10)−0.0055 (9)
C80.0468 (9)0.0533 (10)0.0384 (8)0.0025 (8)−0.0015 (7)0.0060 (7)
C90.0408 (9)0.0441 (8)0.0438 (8)0.0030 (7)−0.0029 (7)0.0030 (7)
C100.0524 (10)0.0632 (11)0.0504 (9)−0.0025 (9)−0.0063 (9)−0.0050 (9)
C110.0552 (12)0.0616 (12)0.0777 (14)−0.0128 (10)−0.0067 (10)−0.0075 (11)
C120.0477 (10)0.0565 (10)0.0795 (13)−0.0095 (9)0.0092 (10)0.0034 (10)
C130.0573 (12)0.0659 (12)0.0591 (11)−0.0072 (10)0.0161 (10)−0.0025 (10)
C140.0493 (9)0.0560 (10)0.0511 (9)−0.0091 (9)0.0067 (9)−0.0061 (8)
C150.0518 (11)0.0768 (15)0.0857 (16)−0.0016 (11)0.0009 (10)−0.0069 (13)

Geometric parameters (Å, °)

S1—O11.5946 (13)C11—C121.363 (3)
S1—O21.4108 (18)C12—C131.370 (3)
S1—O31.4172 (17)C13—C141.380 (2)
S1—C151.739 (2)C3—H30.930
O1—C11.428 (2)C4—H40.930
C1—C21.478 (2)C5—H50.930
C1—C81.328 (2)C6—H60.930
C2—C31.387 (2)C7—H70.930
C2—C71.392 (2)C8—H80.930
C3—C41.386 (2)C10—H100.930
C4—C51.370 (4)C11—H110.930
C5—C61.378 (4)C12—H120.930
C6—C71.385 (3)C13—H130.930
C8—C91.472 (2)C14—H140.930
C9—C101.391 (2)C15—H1510.960
C9—C141.395 (2)C15—H1520.960
C10—C111.384 (3)C15—H1530.960
O1—S1—O2103.76 (10)C4—C3—H3119.9
O1—S1—O3109.35 (9)C3—C4—H4119.9
O1—S1—C15103.16 (9)C5—C4—H4119.9
O2—S1—O3120.36 (11)C4—C5—H5119.9
O2—S1—C15109.61 (12)C6—C5—H5119.9
O3—S1—C15109.16 (11)C5—C6—H6119.9
S1—O1—C1120.53 (10)C7—C6—H6119.9
O1—C1—C2112.84 (13)C2—C7—H7120.0
O1—C1—C8115.45 (14)C6—C7—H7120.0
C2—C1—C8131.66 (15)C1—C8—H8115.1
C1—C2—C3120.36 (15)C9—C8—H8115.1
C1—C2—C7120.41 (15)C9—C10—H10119.5
C3—C2—C7119.18 (16)C11—C10—H10119.5
C2—C3—C4120.20 (19)C10—C11—H11119.7
C3—C4—C5120.2 (2)C12—C11—H11119.7
C4—C5—C6120.3 (2)C11—C12—H12120.2
C5—C6—C7120.1 (2)C13—C12—H12120.2
C2—C7—C6120.0 (2)C12—C13—H13119.8
C1—C8—C9129.70 (16)C14—C13—H13119.8
C8—C9—C10118.61 (15)C9—C14—H14119.5
C8—C9—C14123.81 (15)C13—C14—H14119.5
C10—C9—C14117.37 (16)S1—C15—H151109.5
C9—C10—C11120.93 (19)S1—C15—H152109.5
C10—C11—C12120.6 (2)S1—C15—H153109.5
C11—C12—C13119.6 (2)H151—C15—H152109.5
C12—C13—C14120.5 (2)H151—C15—H153109.5
C9—C14—C13120.97 (18)H152—C15—H153109.5
C2—C3—H3119.9
O2—S1—O1—C1154.37 (13)C2—C3—C4—C5−1.3 (3)
O3—S1—O1—C124.77 (15)C3—C4—C5—C61.5 (3)
C15—S1—O1—C1−91.29 (14)C4—C5—C6—C7−0.6 (4)
S1—O1—C1—C290.79 (14)C5—C6—C7—C2−0.5 (3)
S1—O1—C1—C8−91.52 (17)C1—C8—C9—C10−158.77 (19)
O1—C1—C2—C3−135.28 (16)C1—C8—C9—C1426.6 (2)
O1—C1—C2—C741.9 (2)C8—C9—C10—C11−175.86 (18)
O1—C1—C8—C9−169.44 (16)C8—C9—C14—C13175.14 (18)
C2—C1—C8—C97.7 (3)C10—C9—C14—C130.5 (2)
C8—C1—C2—C347.5 (2)C14—C9—C10—C11−0.9 (2)
C8—C1—C2—C7−135.3 (2)C9—C10—C11—C120.6 (3)
C1—C2—C3—C4177.46 (18)C10—C11—C12—C130.3 (3)
C1—C2—C7—C6−176.5 (2)C11—C12—C13—C14−0.7 (3)
C3—C2—C7—C60.7 (3)C12—C13—C14—C90.3 (3)
C7—C2—C3—C40.2 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C8—H8···O2i0.932.533.376 (2)152
C15—H152···Cg1ii0.962.683.514 (1)145

Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) −x+1, y+1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2190).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst.32, 115–119.
  • Cui, D.-M., Meng, Q., Zheng, J. Z. & Zhang, C. (2009). Chem. Commun. pp. 1577–1579. [PubMed]
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Limmert, M. E., Roy, A. H. & Hartwig, J. F. (2005). J. Org. Chem.70, 9364–9370. [PubMed]
  • Rigaku (2006). PROCESS-AUTO Rigaku Corporation, Tokyo, Japan.
  • Rigaku (2007). CrystalStructure Rigaku Americas Corporation, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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