(2E,4E)-Ethyl 5-(phenyl­sulfon­yl)penta-2,4-dienoate

Ulaganathan Sankar; V Sabari; G Suresh; Ramakrishnan Uma; S Aravindhan

doi:10.1107/S1600536812009907

. 2012 Mar 17;68(Pt 4):o1093. doi: 10.1107/S1600536812009907

(2E,4E)-Ethyl 5-(phenylsulfonyl)penta-2,4-dienoate

Ulaganathan Sankar ^a, V Sabari ^b, G Suresh ^b, Ramakrishnan Uma ^a, S Aravindhan ^b,^*

PMCID: PMC3344046 PMID: 22589955

Abstract

In the title compound, C₁₃H₁₄O₄S, both C=C double bonds adopt an E conformation. In the crystal, molecules are linked into centrosymmetric R ₂ ²(14) dimers via pairs of C—H⋯O hydrogen bonds.

Related literature

For the biological activity of phenyl sulfonyl-containing compounds see: De-Benedetti et al. (1985 ▶). For a related structure, see: Li (2011 ▶).

Experimental

Crystal data

C₁₃H₁₄O₄S
M _r = 266.30
Triclinic,
a = 6.2525 (3) Å
b = 7.8889 (4) Å
c = 14.5049 (7) Å
α = 82.828 (3)°
β = 87.261 (2)°
γ = 72.426 (2)°
V = 676.69 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 298 K
0.45 × 0.38 × 0.15 mm

Data collection

Bruker APEXII KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.899, T _max = 0.965
8948 measured reflections
3084 independent reflections
2621 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.147
S = 1.87
3084 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812009907/bt5831sup1.cif

e-68-o1093-sup1.cif^{(16.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009907/bt5831Isup2.hkl

e-68-o1093-Isup2.hkl^{(148.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812009907/bt5831Isup3.cml

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
C7—H7⋯O3ⁱ	0.93	2.32	3.212 (2)	161

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Symmetry code: (i) Inline graphic .

Acknowledgments

SA thanks the UGC, India, for financial support.

supplementary crystallographic information

Comment

Phenyl sulfonyl containing compounds show a wide range of biological properties (De-Benedetti et al., 1985).

Fig. 1. shows a displacement ellipsoid plot of the title compound. Both C=C double bonds display an E configuration. The title molecule exhibits structural similarities with the already reported related structure (Li, 2011). The dihedral angle between two planes (C5—C6—S1—O1) and (C1—C6—S1—O2) is 37.32 (6)°. The crystal packing is stabilized by C—H···O intermolecular interactions. The molecules are linked into centrosymmetric R₂²(14) dimers via C7—H7···O3 hydrogen bonds (Table 1). The packing of the compound is shown in (Fig. 2).

Experimental

LIHMDS (8 ml, 8.4 mmol, 1.06 molar solution in THF) was added drop wise to a 0 °C cooled solution of bisphenyl sulfonyl methane (1 g, 3.4 mmol) in dried THF (15 ml) under argon atmosphere. The reaction mixture was stirred at same temp for 1 h, and then trans ethyl 4-bromo coronate (0.71 g, 3.7 mmol) in dry THF (5 ml) was added dropwise and the reaction mixture was allowed to come to RT and it was stirred under argon atmosphere for 16 h. The reaction mixture was quenched by adding saturated NH₄Cl (20 ml) and then extracted with ethyl acetate (2x20 ml) and washed with water (2x20 ml) and sat brine (20 ml). Then, the organic layer was dried over MgSO₄. Evaporation of the solvent under vacuum furnished the crude product, the residue was chromatographed (25% ethyl acetate in hexanes) to give analytically pure (2E, 4E)-ethyl 5-(phenyl sulfonyl)penta-2,4-dienote (0.673 g. yield 75%) as a colorless solid.