3-(4-Fluoro­phenyl­sulfin­yl)-2,5-dimethyl-1-benzofuran

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

doi:10.1107/S1600536810003740

. 2010 Feb 6;66(Pt 3):o543. doi: 10.1107/S1600536810003740

3-(4-Fluorophenylsulfinyl)-2,5-dimethyl-1-benzofuran

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

PMCID: PMC2983593 PMID: 21580314

Abstract

In the title compound, C₁₆H₁₃FO₂S, 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 nearly perpendicular to this plane, making a dihedral angle of 87.41 (3). The crystal structure exhibits a weak intermolecular C—H⋯O hydrogen bond.

Related literature

For the crystal structures of similar 2-methyl-3-phenylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2007 ▶, 2008a ▶,b ▶). 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 ▶).

Experimental

Crystal data

C₁₆H₁₃FO₂S
M _r = 288.32
Monoclinic,
a = 11.3951 (5) Å
b = 6.1223 (3) Å
c = 19.6899 (9) Å
β = 100.155 (2)°
V = 1352.13 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 173 K
0.30 × 0.30 × 0.21 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.645, T _max = 0.746
22996 measured reflections
3115 independent reflections
2830 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.099
S = 1.07
3115 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.32 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/S1600536810003740/fk2012sup1.cif

e-66-0o543-sup1.cif^{(18.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003740/fk2012Isup2.hkl

e-66-0o543-Isup2.hkl^{(152.9KB, 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
C10—H10B⋯O2ⁱ	0.98	2.62	3.554 (2)	159

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Molecules containing benzofuran skeleton show various pharmacological activities such as antifungal (Aslam et al., 2006), antitumor and antiviral (Galal et al., 2009), antimicrobial (Khan et al., 2005) properties, and these compounds are widely occurring 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-phenylsulfinyl-1-benzofuran analogues (Choi et al., 2007, 2008a,b), we report the crystal structure of the title compound (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.009 (1) ° 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 [87.41 (3)°] and is tilted slightly towards it. The crystal packing (Fig. 2) is stabilized by a weak intermolecular C—H···O hydrogen bond between the methyl H atom and the oxygen of the S═O unit, with a C10—H10B···O2ⁱ (Table 1).

Experimental

77% 3-Chloroperoxybenzoic acid (291 mg, 1.3 mmol) was added in small portions to a stirred solution of 3-(4-fluorophenylsulfanyl)-2,5-dimethyl-1-benzofuran (326 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 80%, m.p. 420-421 K; R_f = 0.69 (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 ethyl acetate at room temperature.