(E)-1,2-Diphenyl­ethenyl methane­sulfonate

Yonghua Feng; Liu Ying; Chen Zhang

doi:10.1107/S160053681001281X

. 2010 Apr 24;66(Pt 5):o1143. doi: 10.1107/S160053681001281X

(E)-1,2-Diphenylethenyl methanesulfonate

Yonghua Feng ^a, Liu Ying ^b, Chen Zhang ^c,^*

PMCID: PMC2979264 PMID: 21579191

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 ▶). For related structures, see: Cui et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₅H₁₄O₃S
M _r = 274.33
Orthorhombic,
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 ▶) 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
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack (1983 ▶), 1341 Friedel Pairs
Flack parameter: −0.03 (7)

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

Supplementary Material

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

e-66-o1143-sup1.cif^{(16.2KB, cif)}

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

e-66-o1143-Isup2.hkl^{(155.2KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O2ⁱ	0.93	2.53	3.376 (2)	152
C15—H152⋯Cg1ⁱⁱ	0.96	2.68	3.514 (1)	145

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Symmetry codes: (i) Inline graphic ; (ii) . Cg1 is the centroid of the C9–C14 ring.

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.