5-Fluoro-3-(4-fluoro­phenyl­sulfon­yl)-2-methyl-1-benzofuran

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

doi:10.1107/S1600536810025468

. 2010 Jul 3;66(Pt 8):o1909. doi: 10.1107/S1600536810025468

5-Fluoro-3-(4-fluorophenylsulfonyl)-2-methyl-1-benzofuran

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

PMCID: PMC3007400 PMID: 21588241

Abstract

In the title compound, C₁₅H₁₀F₂O₃S, the 4-fluorophenyl ring makes a dihedral angle of 73.20 (4)° with the plane of the benzofuran fragment. The crystal structure is stabilized by aromatic π–π interactions between the furan and benzene rings of neighbouring molecules [centroid–centroid distance = 3.805 (3) Å]. The crystal structure also exhibits weak intermolecular C—H⋯O and C—H⋯F interactions.

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For the structures of related 5-halo-2-methyl-3-phenylsulfonyl-1-benzofuran derivatives, see: Choi et al. (2008a ▶,b ▶,c ▶).

Experimental

Crystal data

C₁₅H₁₀F₂O₃S
M _r = 308.29
Triclinic,
a = 7.2799 (9) Å
b = 9.5161 (12) Å
c = 10.1052 (13) Å
α = 89.844 (2)°
β = 75.057 (2)°
γ = 74.558 (2)°
V = 650.32 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 173 K
0.40 × 0.40 × 0.30 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.674, T _max = 0.746
5657 measured reflections
2797 independent reflections
2404 reflections with I > 2σ(I)
R _int = 0.017

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.092
S = 1.10
2797 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.39 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 datablocks global, I. DOI: 10.1107/S1600536810025468/zl2288sup1.cif

e-66-o1909-sup1.cif^{(18.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025468/zl2288Isup2.hkl

e-66-o1909-Isup2.hkl^{(137.3KB, 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
C11—H11⋯O2ⁱ	0.93	2.45	3.247 (2)	144
C14—H14⋯F2ⁱⁱ	0.93	2.53	3.441 (2)	168

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

supplementary crystallographic information

Comment

Compounds containing a benzofuran skeleton show diverse pharmacological properties such as antifungal (Aslam et al., 2006), antitumor and antiviral (Galal et al., 2009), and antimicrobial (Khan et al., 2005) activities. These compounds widely occur in nature (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our study of the substituent effect on the solid state structures of 5-halo-2-methyl-3-phenylsulfonyl-1-benzofuran analogues (Choi et al., 2008a,b,c), we report the crystal structure of the title compound (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.013 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the benzofuran plane and the 4-fluorophenyl ring is 73.20 (4)°. The crystal packing (Fig. 2) is stabilized by aromatic π–π interactions between the furan and the benzene rings of neighbouring molecules, with a Cg1···Cg2ⁱⁱⁱ distance of 3.805 (3) Å (Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively). The molecular packing (Fig. 2) is further stabilized by a weak intermolecular C—H···O hydrogen bond between the 4-fluorophenyl H atom and the oxygen of the O═S═O unit (C11—H11···O2ⁱ, see Table 1 for symmetry operator and numerical values). The crystal packing (Fig. 2) also exhibits C—H···F hydrogen bonds between the 4-fluorophenyl H atom and the fluorine of 4-fluorophenyl ring (C14—H14···F2ⁱⁱ, Table 1).

Experimental

77% 3-chloroperoxybenzoic acid (381 mg, 1.7 mmol) was added in small portions to a stirred solution of 5-fluoro-3-(4-fluorophenylsulfanyl)-2-methyl-1-benzofuran (221 mg, 0.8 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 8h, 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 76%, m.p. 426–427 K; R_f = 0.49 (benzene)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in benzene at room temperature.