5-Fluoro-2-(2-fluoro­phen­yl)-3-methyl­sulfinyl-1-benzo­furan

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S1600536814014810

. 2014 Jun 25;70(Pt 7):o829. doi: 10.1107/S1600536814014810

5-Fluoro-2-(2-fluorophenyl)-3-methylsulfinyl-1-benzofuran

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

PMCID: PMC4120583 PMID: 25161603

Abstract

In the title compound, C₁₅H₁₀F₂O₂S, the dihedral angle between the plane of the benzofuran ring system (r.m.s. deviation = 0.015 Å) and that of the 2-fluorophenyl ring is 28.53 (6)°. In the crystal, molecules are linked by C—H⋯O and C—H⋯F hydrogen bonds, and by π–π interactions between the furan and benzene rings of neighbouring molecules [centroid–centroid distance = 3.625 (2) Å], forming a three-dimensional network.

Keywords: crystal structure

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2009a ▶,b ▶, 2012 ▶). graphic file with name e-70-0o829-scheme1.jpg

Experimental

Crystal data

C₁₅H₁₀F₂O₂S
M _r = 292.29
Monoclinic,
a = 8.6184 (2) Å
b = 16.8358 (4) Å
c = 9.4019 (2) Å
β = 111.254 (1)°
V = 1271.40 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 173 K
0.55 × 0.27 × 0.24 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.863, T _max = 0.937
12086 measured reflections
3118 independent reflections
2650 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.100
S = 1.07
3118 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.40 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 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814014810/bt6985sup1.cif

e-70-0o829-sup1.cif^{(17.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814014810/bt6985Isup2.hkl

e-70-0o829-Isup2.hkl^{(153KB, hkl)}

Click here for additional data file.^{(4.9KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814014810/bt6985Isup3.cml

CCDC reference: 1009826

Additional supporting information: 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	2.52	3.343 (2)	145
C12—H12⋯O2ⁱⁱ	0.95	2.39	3.326 (2)	166
C15—H15A⋯F1ⁱⁱⁱ	0.98	2.54	3.419 (2)	149

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

supplementary crystallographic information

S1. Comment

As a part of our ongoing project of 5-fluoro-3-methylsulfinyl-1-benzofuran derivatives containing 4-bromophenyl (Choi et al., 2009a), 4-fluorophenyl (Choi et al., 2009b) and 4-methylphenyl (Choi et al., 2012) substituents in 2-position, 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 0.015 (1) Å from the least-squares plane defined by the nine constituent atoms. The 2-fluorophenyl ring is essentially planar, with a mean deviation of 0.053 (1) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring system and the 2-fluorophenyl ring is 28.53 (6)°. In the crystal structure (Fig. 2), molecules are inked by C—H···O and C—H···F hydrogen bonds (Table 1), and by π–π interactions between the furan and benzene rings of neighbouring molecules, with a Cg1···Cg2^iv distance of 3.625 (2) Å and an interplanar distance of 3.295 (2) Å resulting in a slippage of 1.511 (2) Å (Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively), forming a three-dimensional network.

S2. Experimental

3-Chloroperoxybenzoic acid (77%, 269 mg, 1.2 mmol) was added in small portions to a stirred solution of 5-fluoro-2-(2-fluorophenyl)-3-methylsulfanyl-1-benzofuran (304 mg, 1.1 mmol) in dichloromethane (35 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. 412–413 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 acetone at room temperature.