5-Fluoro-3-methyl­sulfinyl-2-phenyl-1-benzofuran

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

doi:10.1107/S1600536809028189

. 2009 Jul 22;65(Pt 8):o1957. doi: 10.1107/S1600536809028189

5-Fluoro-3-methylsulfinyl-2-phenyl-1-benzofuran

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

PMCID: PMC2977333 PMID: 21583635

Abstract

In the title compound, C₁₅H₁₁FO₂S, the O atom and the methyl group of the methylsulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. The 2-phenyl ring is rotated out of the benzofuran plane, making a dihedral angle of 32.1 (2)°. The crystal structure is stabilized by aromatic π–π interactions between the benzene rings of neighbouring molecules [centroid–centroid distance = 3.690 (5) Å]. In addition, the crystal structure exhibits intermolecular C—H⋯O and C—H⋯F interactions.

Related literature

For the crystal structures of similar 5-halo-3-methylsulfinyl-2-phenyl-1-benzofuran derivatives, see: Choi et al. (2007a ▶,b ▶). For the biological and pharmacological activity of benzofuran compounds, see: Howlett et al. (1999 ▶); Ward (1997 ▶).

Experimental

Crystal data

C₁₅H₁₁FO₂S
M _r = 274.30
Monoclinic,
a = 8.507 (4) Å
b = 16.655 (7) Å
c = 9.553 (4) Å
β = 113.732 (5)°
V = 1239.1 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 273 K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: none
8954 measured reflections
2251 independent reflections
1478 reflections with I > 2σ(I)
R _int = 0.133

Refinement

R[F ² > 2σ(F ²)] = 0.061
wR(F ²) = 0.157
S = 1.07
2251 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536809028189/er2071sup1.cif

e-65-o1957-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028189/er2071Isup2.hkl

e-65-o1957-Isup2.hkl^{(110.7KB, hkl)}

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	0.93	2.48	3.282 (5)	145
C12—H12⋯O2ⁱⁱ	0.93	2.48	3.371 (5)	160
C13—H13⋯O2ⁱⁱⁱ	0.93	2.64	3.555 (5)	170
C15—H15B⋯O1^iv	0.96	2.67	3.493 (6)	144
C15—H15A⋯F^v	0.96	2.62	3.509 (6)	155

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

Acknowledgments

This work was supported by Dong-eui University (grant No. 2009AA099).

supplementary crystallographic information

Comment

The benzofuran ring systems have been received considerable attenttion in the field of their biological and pharmacological properties (Howlett et al., 1999; Ward, 1997). This work is related to our communications on the synthesis and structures of 5-halo-3-methylsulfinyl-2-phenyl-1-benzofuran analogues, viz. 5-bromo-3-methylsulfinyl-2-phenyl-1-benzofuran (Choi et al., 2007a) and 5-iodo-3-methylsulfinyl-2-phenyl-1-benzofuran (Choi et al., 2007b). Here we report the crystal structure of the title compound, 5-fluoro-3-methylsulfinyl-2-phenyl-1-benzofuran (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.011 (3) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the planes of the benzofuran and the phenyl rings is 3.690 (5)°. The crystal packing (Fig. 2) is stabilized by aromatic π–π interactions between the benzene rings of the adjacent molecules, with a Cg···Cg distance of 3.690 (5) Å (Cg is the centroid of the C2–C7 benzene ring). The crystal packing (Fig. 2) exhibits four C–H···O and an C–H···F intermolecular interactions (Table 1 and Fig. 2).

Experimental

The 77% 3-chloroperoxybenzoic acid (291 mg, 1.3 mmol) was added in small portions to a stirred solution of 5-fluoro-3-methylsulfanyl-2-phenyl-1-benzofuran (310 mg, 1.2 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 3h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by column chromatography (hexane-ethyl acetate, 1 : 1 v/v) to afford the title compound as a colorless solid [yield 83%, m.p. 462-463 K; R_f = 0.47 (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 tetrahydrofuran at room temperature.