3-(3-Fluoro­phenyl­sulfin­yl)-2,5,7-trimethyl-1-benzofuran

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

doi:10.1107/S1600536811018654

. 2011 May 20;67(Pt 6):o1468. doi: 10.1107/S1600536811018654

3-(3-Fluorophenylsulfinyl)-2,5,7-trimethyl-1-benzofuran

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

PMCID: PMC3120630 PMID: 21754839

Abstract

In the title compound, C₁₇H₁₅FO₂S, the 3-fluorophenyl ring makes a dihedral angle of 86.89 (4)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds. The crystal structure also exhibits a slipped π–π interaction between the furan rings of neighbouring molecules [centroid–centroid distance = 3.719 (2) Å, interplanar distance = 3.475 (2) Å and slippage = 1.325 Å].

Related literature

For the biological activity of benzofuran compounds, see: Aslam et al. (2009 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For structural studies of related 3-(4-fluorophenylsulfinyl)-2,5-dimethyl-1-benzofuran derivatives, see: Choi et al. (2010a ▶,b ▶).

Experimental

Crystal data

C₁₇H₁₅FO₂S
M _r = 302.35
Triclinic,
a = 6.2942 (2) Å
b = 11.1162 (4) Å
c = 11.8021 (6) Å
α = 110.701 (3)°
β = 100.176 (3)°
γ = 103.621 (2)°
V = 719.39 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 296 K
0.29 × 0.25 × 0.21 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.935, T _max = 0.951
12696 measured reflections
3301 independent reflections
2760 reflections with I > 2σ(I)
R _int = 0.122

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.133
S = 1.07
3301 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.44 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/S1600536811018654/ez2242sup1.cif

e-67-o1468-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018654/ez2242Isup2.hkl

e-67-o1468-Isup2.hkl^{(161.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811018654/ez2242Isup3.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
C13—H13⋯O2ⁱ	0.93	2.51	3.227 (2)	134

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Many compounds containing a benzofuran ring system exhibit interesting pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2009, Galal et al., 2009, Khan et al., 2005). These compounds occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our study of the substituent effect on the solid state structures of 3-(4-fluorophenylsulfinyl)-2,5-dimethyl-1-benzofuran analogues (Choi et al., 2010a,b), we report the crystal structure of the title compound.

In the title compound (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.007 (1) Å from the least-squares plane defined by the nine constituent atoms. The 3-fluorophenyl ring makes a dihedral angle of 86.89 (4)° with the mean plane of the benzofuran fragment. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds between a 3-fluorophenyl H atom and the O atom of the sulfinyl group (Table 1; C13—H13···O2ⁱ). The crystal packing (Fig. 2) is further stabilized by a weak slipped π–π interaction between the furan rings of neighbouring molecules, with a Cg···Cgⁱⁱ distance of 3.719 (2) Å and an interplanar distance of 3.475 (2) Å resulting in a slippage of 1.325 Å (Cg is the centroid of the C1/C2/C7/O1/C8 furan ring).

Experimental

77% 3-chloroperoxybenzoic acid (291 mg, 1.3 mmol) was added in small portions to a stirred solution of 3-(3-fluorophenylsulfanyl)-2,5,7-trimethyl-1-benzofuran (342 mg, 1.2 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 4h, 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 (hexane–ethyl acetate, 1:1 v/v) to afford the title compound as a colorless solid [yield 75%, m.p. 434–435 K; R_f = 0.72 (hexane–ethyl acetate, 1:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.