5-Ethyl-3-(4-Fluoro­phenyl­sulfon­yl)-2-methyl-1-benzofuran

Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee

doi:10.1107/S1600536810036391

. 2010 Sep 18;66(Pt 10):o2575. doi: 10.1107/S1600536810036391

5-Ethyl-3-(4-Fluorophenylsulfonyl)-2-methyl-1-benzofuran

Hong Dae Choi ^a, Pil Ja Seo ^a, Byeng Wha Son ^b, Uk Lee ^b,^*

PMCID: PMC2983155 PMID: 21587558

Abstract

In the title molecule, C₁₇H₁₅FO₃S, the 4-fluorophenyl ring makes a dihedral angle of 74.06 (4)° with the mean plane of the benzofuran fragment. In the crystal structure, molecules are linked by weak intermolecular C—H⋯O and C—H⋯π interactions. The crystal structure also exhibits aromatic π–π interactions between the benzene rings of adjacent molecules [centroid–centroid distance = 3.629 (2) Å].

Related literature

For the crystal structures of similar 3-(4-fluorophenylsulfonyl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010a ▶,b ▶). For the biological activity of benzofuran compounds, see: Aslam et al. (2006 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶).

Experimental

Crystal data

C₁₇H₁₅FO₃S
M _r = 318.35
Triclinic,
a = 8.0042 (1) Å
b = 9.7114 (2) Å
c = 11.3741 (2) Å
α = 66.487 (1)°
β = 82.998 (1)°
γ = 67.964 (1)°
V = 751.10 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 173 K
0.31 × 0.25 × 0.24 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.929, T _max = 0.946
13998 measured reflections
3722 independent reflections
3264 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.102
S = 1.04
3722 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810036391/su2211sup1.cif

e-66-o2575-sup1.cif^{(19.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810036391/su2211Isup2.hkl

e-66-o2575-Isup2.hkl^{(182.5KB, hkl)}

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

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

Cg is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2ⁱ	0.95	2.40	3.3143 (17)	161
C11—H11C⋯Cgⁱⁱ	0.98	2.66	3.491 (2)	143

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This work was supported by Blue-Bio Industry RIC at Dongeui University as a RIC program under the Ministry of Knowledge Economy and the city of Busan.

supplementary crystallographic information

Comment

Many compounds containing a benzofuran ring show important biological properties such as, antifungal (Aslam et al., 2006), antitumor and antiviral (Galal et al., 2009), antimicrobial (Khan et al., 2005) activities. These compounds occur widely in nature (Akgul & Anil, 2003; Soekamto et al., 2003). As part of our ongoing studies of the effect of side chain substituents on the solid state structures of 3-(4-fluorophenylsulfonyl)-2-methyl-1-benzofuran analogues (Choi et al., 2010a,b), we report herein on the crystal structure of the title compound.

In the title molecule (Fig. 1) the benzofuran unit is essentially planar, with a mean deviation of 0.009 (1) Å from the least-squares plane defined by the nine constituent atoms. The 4-fluorophenyl ring makes a dihedral angle of 74.06 (4)° with the mean plane of the benzofuran fragment.

The crystal packing (Fig. 2) is stabilized by a weak intermolecular C–H···O hydrogen bond between the 4-fluorophenyl H atom and the oxygen of the O═ S═O unit[ C13–H13···O2ⁱ; see Table 1], and by an intermolecular C–H···π interaction between a methyl H-atom and the benzene ring of a neighbouring molecule [C11–H11C···Cgⁱⁱ ; see Table 1]. The molecular packing (Fig. 2) is further stabilized by an aromatic π···π interaction between the benzene rings of neighbouring molecules, with a Cg···Cgⁱⁱⁱ distance of 3.629 (2) Å (Cg is the centroid of the C2-C7 benzene ring; see Table 1).

Experimental

77% 3-chloroperoxybenzoic acid (381 mg, 1.7 mmol) was added in small portions to a stirred solution of 5-ethyl-3-(4-fluorophenylsulfanyl)-2-methyl-1-benzofuran (229 mg, 0.8 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 6h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (silica gel, benzene) to afford the title compound as a colorless solid [yield 82%, m.p. 377-378 K; R_f = 0.68 (benzene)]. Single crystals, suitable for X-ray diffraction, were prepared by slow evaporation of a solution of the title compound in diisopropyl ether at room temperature.