5-Fluoro-2-(4-methyl­phen­yl)-3-methyl­sulfinyl-1-benzofuran

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S1600536812044844

. 2012 Nov 14;68(Pt 12):o3338. doi: 10.1107/S1600536812044844

5-Fluoro-2-(4-methylphenyl)-3-methylsulfinyl-1-benzofuran

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

PMCID: PMC3588940 PMID: 23476176

Abstract

In the title compound, C₁₆H₁₃FO₂S, the 4-methylphenyl ring makes a dihedral angle of 29.53 (4)° with the mean plane of the benzofuran fragment [r.m.s. deviation = 0.004 (1) Å]. In the crystal, molecules are linked by pairs of weak C—H⋯O hydrogen bonds, forming inversion dimers that stack along the a axis.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2009a ▶,b ▶).

Experimental

Crystal data

C₁₆H₁₃FO₂S
M _r = 288.32
Triclinic,
a = 8.0407 (2) Å
b = 8.0838 (2) Å
c = 11.3517 (2) Å
α = 80.126 (1)°
β = 85.091 (1)°
γ = 66.773 (1)°
V = 667.88 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 173 K
0.53 × 0.40 × 0.24 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.701, T _max = 0.746
12234 measured reflections
3307 independent reflections
3095 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.091
S = 1.09
3307 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.24 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

Click here for additional data file.^{(23.8KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812044844/su2522sup1.cif

e-68-o3338-sup1.cif^{(23.8KB, cif)}

Click here for additional data file.^{(162.2KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812044844/su2522Isup2.hkl

e-68-o3338-Isup2.hkl^{(162.2KB, hkl)}

Click here for additional data file.^{(5.2KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812044844/su2522Isup3.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
C14—H14⋯O2ⁱ	0.95	2.54	3.4138 (16)	154

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the Blue-Bio Industry Regional Innovation Center (RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan City.

supplementary crystallographic information

Comment

As a part of our ongoing study of 5-fluoro-3-methylsulfinyl-1-benzofuran derivatives with various substituents in the 2-position, such as 4-bromophenyl (Choi et al., 2009a) or 4-iodophenyl (Choi et al., 2009b), 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 0.004 (1) Å from the mean plane defined by the nine constituent atoms. The dihedral angle between the 4-methylphenyl ring and the mean plane of the benzofuran ring is 29.53 (4)°.

In the crystal, molecules are connected by a pair of weak C—H···O hydrogen bonds, forming inversion dimers that stack along the a axis (Table 1).

Experimental

3-Chloroperoxybenzoic acid (77%, 269 mg, 1.2 mmol) was added in small portions to a stirred solution of 5-fluoro-2-(4-methylphenyl)-3-methylsulfanyl-1-benzofuran (326 mg, 1.1 mmol) in dichloromethane (30 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 73%, m.p. 417–418 K; R_f = 0.45 (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 acetone at room temperature.