5-Bromo-3-(4-fluoro­phenyl­sulfin­yl)-2-methyl-1-benzofuran

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

doi:10.1107/S1600536810016181

. 2010 May 8;66(Pt 6):o1297. doi: 10.1107/S1600536810016181

5-Bromo-3-(4-fluorophenylsulfinyl)-2-methyl-1-benzofuran

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

PMCID: PMC2979595 PMID: 21579394

Abstract

In the title compound, C₁₅H₁₀BrFO₂S, the O atom and the 4-fluorophenyl group of the 4-fluorophenylsulfinyl substituent are located on opposite sides of the plane through the benzofuran fragment; the 4-fluorophenyl ring is approximately perpendicular to this plane [dihedral angle = 89.38 (6)°]. In the crystal, molecules are linked by a Br⋯Br contact [3.4816 (5) Å], and weak intermolecular C—S⋯π [3.499 (2) Å] and C—F⋯π [3.535 (2) Å] interactions.

Related literature

For the crystal structures of similar derivatives, see: Choi et al. (2010a ▶,b ▶). For the biological 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 ▶).

Experimental

Crystal data

C₁₅H₁₀BrFO₂S
M _r = 353.20
Monoclinic,
a = 11.4704 (4) Å
b = 6.1776 (2) Å
c = 19.6420 (7) Å
β = 98.432 (2)°
V = 1376.78 (8) Å³
Z = 4
Mo Kα radiation
μ = 3.15 mm⁻¹
T = 173 K
0.32 × 0.26 × 0.21 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.453, T _max = 0.746
11827 measured reflections
3148 independent reflections
2655 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.028
wR(F ²) = 0.072
S = 1.05
3148 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.53 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/S1600536810016181/ng2767sup1.cif

e-66-o1297-sup1.cif^{(17.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016181/ng2767Isup2.hkl

e-66-o1297-Isup2.hkl^{(154.5KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

The compounds containing benzofuran skeleton show potent biological activities such as antifungal (Aslam et al.., 2006), antitumor and antiviral (Galal et al.., 2009), antimicrobial (Khan et al.., 2005) properties. These compounds occur widely in nature (Akgul & Anil, 2003; Soekamto et al.. 2003). As a part of our ongoing studies of the effect of side chain substituents on the solid state structures of 2-methyl-3-(4-fluorophenylsulfinyl)-1-benzofuran analogues (Choi et al.., 2010a,b), we report the crystal structure of the title compound (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.007 (1) Å from the least-squares plane defined by the nine constituent atoms. The 4-fluorophenyl ring is almost perpendicular to the plane of the benzofuran fragment [89.38 (6)°] and is tilted slightly towards it. The crystal packing (Fig. 2) is stabilized by a Br···Br interaction at 3.4816 (5) Å. The molecular packing (Fig. 2) is further stabilized by a weak intermolecular C–S···π interaction between the sulfur and the 4-fluorophenyl ring of an adjacent molecule, with a C1–S···Cg1ⁱⁱ [3.499 (2) Å] (Cg1 is the centroid of the C10-C15 4-fluorophenyl ring), and by a weak intermolecular C–F···π interaction between the fluorine and the benzene ring of a neighbouring benzofuran system, with C13–F···Cg2ⁱⁱⁱ [3.535 (2) Å] (Cg2 is the centroid of the C2-C7 benzene ring).

Experimental

77% 3-Chloroperoxybenzoic acid (224 mg, 1.0 mmol) was added in small portions to a stirred solution of 5-bromo-3-(4-fluorophenylsulfanyl)-2-methyl-1-benzofuran (303 mg, 0.9 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 (silica gel, hexane-ethyl acetate, 1:1 v/v) to afford the title compound as a colorless solid [yield 78%, m.p. 401-402 K; R_f = 0.64 (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 benzene at room temperature.