3-(3-Fluoro­phenyl­sulfin­yl)-2,4,6-trimethyl-1-benzofuran

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

doi:10.1107/S1600536811043716

. 2011 Oct 29;67(Pt 11):o3113. doi: 10.1107/S1600536811043716

3-(3-Fluorophenylsulfinyl)-2,4,6-trimethyl-1-benzofuran

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

PMCID: PMC3247498 PMID: 22220116

Abstract

In the title compound, C₁₇H₁₅FO₂S, the 3-fluorophenyl ring makes a dihedral angle of 78.38 (4)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by weak C—H⋯O and C—H⋯π interactions. The crystal structure also exhibits a slipped π–π interaction between the furan and benzene rings of neighbouring molecules [centroid–centroid distances = 3.628 (2) Å, interplanar distance = 3.417 (2) Å and slippage = 1.219 (2) Å].

Related literature

For the pharmacological 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 the crystal structures of related compounds, see: Choi et al. (2010a ▶,b ▶).

Experimental

Crystal data

C₁₇H₁₅FO₂S
M _r = 302.35
Triclinic,
a = 6.8561 (2) Å
b = 8.0705 (2) Å
c = 13.9069 (3) Å
α = 103.719 (1)°
β = 91.280 (1)°
γ = 106.973 (1)°
V = 711.50 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 173 K
0.36 × 0.20 × 0.17 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.919, T _max = 0.960
12726 measured reflections
3257 independent reflections
2971 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.098
S = 1.06
3257 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.29 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 datablock(s) global, I. DOI: 10.1107/S1600536811043716/mw2033sup1.cif

e-67-o3113-sup1.cif^{(24.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043716/mw2033Isup2.hkl

e-67-o3113-Isup2.hkl^{(159.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811043716/mw2033Isup3.cml

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

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

Cg2 is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯O2ⁱ	0.98	2.30	3.2727 (18)	172
C10—H10A⋯Cg2ⁱⁱ	0.98	2.74	3.655 (2)	155

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

supplementary crystallographic information

Comment

Substituted benzofuran derivatives have drawn much attention due to their valuable 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 benzofuran derivatives occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing study of benzofuran derivatives containing either 3-(4-fluorophenylsulfinyl) (Choi et al., 2010a) or 3-(4-chlorophenylsufinyl) (Choi et al., 2010b) substituents, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.019 (1) ° from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 3-fluorophenyl ring and the mean plane of the benzofuran fragment is 78.38 (4)°. The crystal packing (Fig. 2) is stabilized by weak intermolecular C–H···O and C–H···π interactions (Table 1) as well as by a weak slipped π–π interaction between the furan and benzene rings of adjacent molecules with a Cg1···Cg2ⁱⁱⁱ distance of 3.628 (2) Å and an interplanar distance of 3.417 (2) Å resulting in a slippage of 1.219 (2) Å (Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2-C7 benzene ring, respectively).

Experimental

77% 3-chloroperoxybenzoic acid (291 mg, 1.3 mmol) was added in small portions to a stirred solution of 3-(3-fluorophenylsulfanyl)-2,4,6-trimethyl 1-benzofuran (343 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, 2:1 v/v) to afford the title compound as a colorless solid [yield 76%, m.p. 406-407 K; R_f = 0.55 (hexane-ethyl acetate, 4:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in benzene at room temperature.