5-Fluoro-3-(3-fluoro­phenyl­sulfon­yl)-2-methyl-1-benzofuran

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S1600536812031972

. 2012 Jul 18;68(Pt 8):o2477. doi: 10.1107/S1600536812031972

5-Fluoro-3-(3-fluorophenylsulfonyl)-2-methyl-1-benzofuran

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

PMCID: PMC3414932 PMID: 22904919

Abstract

In the title compound, C₁₅H₁₀F₂O₃S, the 3-fluorophenyl ring makes a dihedral angle of 79.51 (6)° with the mean plane [r.m.s. deviation = 0.006 (2) Å] of the benzofuran fragment. In the crystal, molecules are linked by weak C—H⋯F and C—H⋯O hydrogen bonds. The crystal structure also exhibits slipped π–π interactions between the benzene and furan rings of neighbouring molecules [centroid–centroid distances = 3.563 (3) and 3.820 (3) Å and slippages of 0.358 (3)and 1.551 (3) Å]. In the 3-fluorophenyl ring, the F atom is disordered over two positions with site-occupancy factors of 0.887 (3) and 0.113 (3).

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010 ▶, 2012 ▶).

Experimental

Crystal data

C₁₅H₁₀F₂O₃S
M _r = 308.29
Monoclinic,
a = 7.2772 (2) Å
b = 11.0972 (3) Å
c = 16.5625 (5) Å
β = 100.698 (2)°
V = 1314.28 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 296 K
0.30 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.663, T _max = 0.746
12792 measured reflections
3275 independent reflections
2732 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.104
S = 1.04
3275 reflections
202 parameters
14 restraints
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.31 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/S1600536812031972/pk2432sup1.cif

e-68-o2477-sup1.cif^{(23KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031972/pk2432Isup2.hkl

e-68-o2477-Isup2.hkl^{(160.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812031972/pk2432Isup3.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⋯F2ⁱ	0.93	2.45	3.302 (2)	153
C15—H15⋯O3ⁱⁱ	0.93	2.47	3.3754 (19)	165

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

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 continuing study of 5-fluoro-2-methyl-1-benzofuran derivatives containing 3-(4-fluorophenylsulfonyl) (Choi et al., 2010) and 3-(4-methylphenylsulfonyl) (Choi et al., 2012) 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 0.006 (2) Å from the least-squares plane defined by the nine constituent atoms. In the 3-fluorophenyl ring, the F atom is disordered over two positions with site-occupancy factors, from refinement of 0.887 (3) (part A) and 0.113 (3) (part B). The dihedral angle between the 3-fluorophenyl ring and the mean plane of the benzofuran ring is 79.51 (6)°. In the crystal structure (Fig. 2), molecules are connected by weak intermolecular C–H···F and C–H···O hydrogen bonds (Table 1). The crystal packing (Fig. 3) also exhibits slipped π–π interactions between the benzene and furan rings of neighbouring molecules, with Cg1···Cg2ⁱⁱⁱ and Cg1···Cg2^iv distances of 3.563 (3) Å & 3.820 (3) Å, and interplanar distances of 3.545 (3) Å & 3.491 (3) Å resulting in slippages of 0.358 (3) Å & 1.551 (3) Å (Cg1 and Cg2 are the centroids of the C2-C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively).

Experimental

3-Chloroperoxybenzoic acid (77%, 515 mg, 2.3 mmol) was added in small portions to a stirred solution of 5-fluoro-3-(3-fluorophenylsulfanyl)-2-methyl-1-benzofuran (304 mg, 1.1 mmol) in dichloromethane (50 mL) at 273 K. After being stirred at room temperature for 10h, 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 (benzene) to afford the title compound as a colorless solid [yield 73%, m.p. 443-444 K; R_f = 0.66 (benzene)]. 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.