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

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S1600536812013086

. 2012 Mar 27;68(Pt 4):o1237. doi: 10.1107/S1600536812013086

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

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

PMCID: PMC3344167 PMID: 22606170

Abstract

In the title compound, C₂₀H₁₂FIO₂S, the dihedral angles between the mean plane [r.m.s. deviation = 0.014 (1) Å] of the benzofuran fragment and the pendant 4-fluorophenyl and phenyl rings are 8.0 (1) and 86.06 (6)°, respectively. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds. The crystal structure also exhibits weak π–π interactions between the furan and benzene rings of neighbouring molecules [centroid–centroid distance = 3.547 (2) Å, interplanar distance = 3.397 (2) Å and slippage = 1.021 (2) Å].

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2011 ▶); Seo et al. (2011 ▶).

Experimental

Crystal data

C₂₀H₁₂FIO₂S
M _r = 462.26
Triclinic,
a = 8.1771 (2) Å
b = 9.8877 (2) Å
c = 11.8423 (3) Å
α = 103.108 (1)°
β = 90.872 (1)°
γ = 111.546 (1)°
V = 862.23 (4) Å³
Z = 2
Mo Kα radiation
μ = 2.00 mm⁻¹
T = 173 K
0.27 × 0.26 × 0.12 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.516, T _max = 0.746
15186 measured reflections
3974 independent reflections
3696 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.024
wR(F ²) = 0.060
S = 1.07
3974 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.75 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 datablock(s) global, I. DOI: 10.1107/S1600536812013086/kj2197sup1.cif

e-68-o1237-sup1.cif^{(25.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013086/kj2197Isup2.hkl

e-68-o1237-Isup2.hkl^{(194.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812013086/kj2197Isup3.cml

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
C19—H19⋯O2ⁱ	0.95	2.38	3.297 (3)	163

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

As a part of our ongoing study of 2-(4-fluorophenyl)-5-halo-3-phenylsulfinyl-1-benzofuran derivatives containing 5-chloro (Choi et al., 2011) and 5-bromo (Seo et al., 2011) substituents, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.014 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angles between the mean plane of the benzofuran fragment and the pendant 4-fluorophenyl and phenyl rings are 8.0 (1)° and 86.06 (6)°, respectively. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds (Table 1). The crystal packing (Fig. 2) is further stabilized by weak π–π interactions between the furan and benzene rings of neighbouring molecules, with a Cg1···Cg2ⁱⁱ distance of 3.547 (2) Å and an interplanar distance of 3.397 (2) Å resulting in a slippage of 1.021 (2) Å (Cg1 and Cg2are the centroids of the C1/C2/C7/O1/C8 furan ring and C2–C7 benzene ring, respectively).

Experimental

77% 3-Chloroperoxybenzoic acid (179 mg, 0.8 mmol) was added in small portions to a stirred solution of 2-(4-fluorophenyl)-5-iodo-3-phenylsulfanyl-1-benzofuran (312 mg, 0.7 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 (hexane:ethyl acetate, 4:1 v/v) to afford the title compound as a colorless solid [yield 52%, m.p. 435–436 K; R_f = 0.49 (hexane:ethyl acetate, 4:1 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.