3-(3-Fluoro­phenyl­sulfin­yl)-2,4,6,7-tetra­methyl-1-benzofuran

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

doi:10.1107/S1600536811016102

. 2011 May 7;67(Pt 6):o1323. doi: 10.1107/S1600536811016102

3-(3-Fluorophenylsulfinyl)-2,4,6,7-tetramethyl-1-benzofuran

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

PMCID: PMC3120326 PMID: 21754720

Abstract

In the title compound, C₁₈H₁₇FO₂S, the 3-fluorophenyl ring makes a dihedral angle of 78.30 (5)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions.

Related literature

For the biological activity of benzofuran compounds, see: Aslam et al. (2009 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For structural studies of related 3-(4-fluorophenylsulfinyl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010a ▶,b ▶).

Experimental

Crystal data

C₁₈H₁₇FO₂S
M _r = 316.38
Triclinic,
a = 7.2690 (2) Å
b = 8.0039 (3) Å
c = 13.7968 (5) Å
α = 76.839 (1)°
β = 88.561 (1)°
γ = 77.506 (1)°
V = 762.86 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 173 K
0.29 × 0.24 × 0.09 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.936, T _max = 0.979
13783 measured reflections
3520 independent reflections
2958 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.107
S = 1.05
3520 reflections
203 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.30 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/S1600536811016102/zq2099sup1.cif

e-67-o1323-sup1.cif^{(19.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016102/zq2099Isup2.hkl

e-67-o1323-Isup2.hkl^{(172.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811016102/zq2099Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12C⋯O2ⁱ	0.98	2.34	3.295 (2)	165
C10—H10A⋯Cgⁱⁱ	0.98	2.74	3.547 (2)	141

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

supplementary crystallographic information

Comment

A series of benzofuran ring system show interesting pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2009; Galal et al., 2009; Khan et al., 2005). These compounds occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our study of the substituent effect on the solid state structures of 3-(4-fluorophenylsulfinyl)-2-methyl-1-benzofuran analogues (Choi et al., 2010a,b), we report the crystal structure of the title compound.

In the title compound (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.016 (1) Å from the least-squares plane defined by the nine constituent atoms. The 3-fluorophenyl ring makes a dihedral angle of 78.30 (5)° with the mean plane of the benzofuran fragment. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds between a methyl H atom and the O atom of the sulfinyl group (Table 1; C12—H12C···O2ⁱ). The crystal structure is further stabilized by intermolecular C—H···π interactions between a methyl H atom and the benzene ring (Table 1; C10—H10A···Cgⁱⁱ, Cg being the centroid of the C2–C7 benzene ring).

Experimental

77% 3-chloroperoxybenzoic acid (269 mg, 1.2 mmol) was added in small portions to a stirred solution of 3-(3-fluorophenylsulfanyl)-2,4,6,7-tetramethyl-1-benzofuran (360 mg, 1.2 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 5h, 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 (hexane–ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [yield 79%, m.p. 413–414 K; R_f = 0.58 (hexane–ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in acetone at room temperature.