5-(4-Fluoro­phen­yl)-2-methyl-3-methyl­sulfinyl-1-benzofuran

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

doi:10.1107/S160053681103056X

. 2011 Aug 2;67(Pt 9):o2242. doi: 10.1107/S160053681103056X

5-(4-Fluorophenyl)-2-methyl-3-methylsulfinyl-1-benzofuran

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

PMCID: PMC3200607 PMID: 22065410

Abstract

In the title compound, C₁₆H₁₃FO₂S, the 4-fluorophenyl ring makes a dihedral angle of 38.75 (8)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds.

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 structural studies of related 5-aryl-2-methyl-3-methylsulfinyl-1-benzofuran drivatives, see: Choi et al. (2006 ▶, 2009 ▶). For the synthesis of 2-methylbenzofuran derivatives, see: Choi et al. (1999 ▶).

Experimental

Crystal data

C₁₆H₁₃FO₂S
M _r = 288.32
Monoclinic,
a = 15.101 (5) Å
b = 5.3150 (16) Å
c = 17.317 (5) Å
β = 93.606 (5)°
V = 1387.1 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 173 K
0.28 × 0.22 × 0.21 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.934, T _max = 0.952
13601 measured reflections
3478 independent reflections
2437 reflections with I > 2σ(I)
R _int = 0.055

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.137
S = 1.05
3478 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.22 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/S160053681103056X/qk2019sup1.cif

e-67-o2242-sup1.cif^{(27.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103056X/qk2019Isup2.hkl

e-67-o2242-Isup2.hkl^{(170.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681103056X/qk2019Isup3.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
C5—H5⋯O2ⁱ	0.95	2.36	3.245 (3)	156
C16—H16B⋯O2ⁱⁱ	0.98	2.43	3.319 (3)	151

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

supplementary crystallographic information

Comment

Recently, many compounds having a benzofuran moiety have drawn much attention owing 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 studies of the substituent effect on the solid state structures of 5-aryl-2-methyl-3-methylsulfinyl-1-benzofuran analogues, see: Choi et al. (2006, 2009), 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 0.011 (2) Å from the least-squares plane defined by the nine constituent atoms. The diheral angle formed by the 4-fluorophenyl ring and the mean plane of the benzofurn fragment is 38.75 (8)°. In the crystal packing (Fig. 2), molecules are linked by weak intermolecular C—H···O hydrogen bonds; the first one between a benzene H atom and the O atom of the sulfinyl group (Table 1; C5—H5···O2ⁱ), the second one between a methyl H atom of the methylsulfinyl group and the O atom of the sulfinyl group (Table 1; C16—H16B···O2ⁱⁱ).

Experimental

5-(4-Fluorophenyl)-2-methyl-3-methylsulfanyl-1-benzofuran was obtained from 4'-fluoro-1,1'-biphenyl-4-ol and α-chloro-α-(methylsufanyl)acetone (Choi et al., 1999). 77% 3-chloroperoxybenzoic acid (291 mg, 1.3 mmol) was added in small portions to a stirred solution of 5-(4-fluorophenyl)-2-methyl-3-methylsulfanyl-1-benzofuran (326 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 70%, m.p. 411–413 K; R_f = 0.46 (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.