2-(4-Fluoro­phen­yl)-5-iodo-3-methyl­sulfinyl-1-benzofuran

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

doi:10.1107/S1600536809051642

. 2009 Dec 4;66(Pt 1):o44. doi: 10.1107/S1600536809051642

2-(4-Fluorophenyl)-5-iodo-3-methylsulfinyl-1-benzofuran

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

PMCID: PMC2980179 PMID: 21580148

Abstract

In the title compound, C₁₅H₁₀FIO₂S, the O atom and the methyl group of the methylsulfinyl substituent are located on opposite sides of the plane through the benzofuran fragment. The 4-fluorophenyl ring is rotated out of the benzofuran plane by a dihedral angle of 28.33 (5)°. The crystal structure is stabilized by a weak non-classical intermolecular C—H⋯O hydrogen bond and an I⋯O halogen interaction [3.211 (1) Å].

Related literature

For the crystal structures of similar 2-(4-fluorophenyl)-3-methylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2009a ▶,b ▶). For natural products with benzofuran ring systems, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For the biological activity of benzofuran compounds, see: Aslam et al. (2006 ▶); Galal et al. (2009 ▶). For a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C₁₅H₁₀FIO₂S
M _r = 400.19
Triclinic,
a = 8.1045 (2) Å
b = 8.2699 (2) Å
c = 11.0999 (3) Å
α = 94.538 (1)°
β = 91.118 (1)°
γ = 111.982 (1)°
V = 686.73 (3) Å³
Z = 2
Mo Kα radiation
μ = 2.49 mm⁻¹
T = 173 K
0.32 × 0.31 × 0.30 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.504, T _max = 0.526
12180 measured reflections
3179 independent reflections
3130 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.018
wR(F ²) = 0.047
S = 1.17
3179 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.90 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 I. DOI: 10.1107/S1600536809051642/zq2022sup1.cif

e-66-00o44-sup1.cif^{(17.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051642/zq2022Isup2.hkl

e-66-00o44-Isup2.hkl^{(155.9KB, 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—H10⋯O2ⁱ	0.95	2.53	3.432 (2)	158

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Molecules involving benzofuran moiety have attracted widespread interest owing to their presence in natural products (Akgul & Anil, 2003; Soekamto et al., 2003) and their biological activity (Aslam et al., 2006; Galal et al., 2009). As a part of our continuing studies of the effect of side chain substituents on the solid state structures of 2-(4-fluorophenyl)-3-methylsulfinyl-1-benzofuran analogues (Choi et al., 2009a,b), we report the crystal structure of the title compound (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.010 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the plane of the benzofuran and the 4-fluorophenyl ring is 28.33 (5)°. The crystal packing (Fig. 2) is stabilized by a weak non-classical intermolecular C—H···O hydrogen bond between the 4-fluorophenyl H atom and the oxygen of the S═O unit, with a C10—H10···O2ⁱ (Table 1), and an I···O halogen bond between the iodine and the oxygen of the S═O unit [I···O2ⁱⁱ = 3.211 (1) Å; C—I···Oⁱⁱ = 170.98 (5)°] (Politzer et al., 2007).

Experimental

77% 3-Chloroperoxybenzoic acid (247 mg, 1.1 mmol) was added in small portions to a stirred solution of 2-(4-fluorophenyl)-5-iodo-3-methylsulfanyl-1-benzofuran (384 mg, 1.0 mmol) in dichloromethane (20 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 87%, m.p. 485–486 K; R_f = 0.66 (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 chloroforrm at room temperature.