2-(4-Fluoro­phen­yl)-5-iodo-7-methyl-3-phenyl­sulfinyl-1-benzo­furan

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S1600536813011793

. 2013 May 4;69(Pt 6):o820. doi: 10.1107/S1600536813011793

2-(4-Fluorophenyl)-5-iodo-7-methyl-3-phenylsulfinyl-1-benzofuran

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

PMCID: PMC3684910 PMID: 23795012

Abstract

In the title compound, C₂₁H₁₄FIO₂S, the dihedral angles between the mean plane [r.m.s. deviation = 0.007 (1) Å] of the benzofuran fragment and the pendant 4-fluorophenyl and phenyl rings are 3.66 (7) and 82.37 (6)°, respectively. In the crystal, molecules are linked by pairs of C—H⋯I hydrogen bonds into centrosymmetric dimers, which are further packed into stacks along the b axis by C—H⋯O hydrogen bonds. In addition, the stacked molecules exhibit inversion-related S⋯O contacts [2.9627 (14) Å] involving the sulfinyl groups.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2009 ▶, 2012 ▶). For details of sulfinyl–sulfinyl interactions, see: Choi et al. (2008 ▶) and for a review of carbonyl–carbonyl interactions, see: Allen et al. (1998 ▶).

Experimental

Crystal data

C₂₁H₁₄FIO₂S
M _r = 476.28
Triclinic,
a = 8.1060 (3) Å
b = 10.7771 (4) Å
c = 11.2639 (4) Å
α = 71.814 (2)°
β = 74.496 (2)°
γ = 79.038 (2)°
V = 894.69 (6) Å³
Z = 2
Mo Kα radiation
μ = 1.93 mm⁻¹
T = 173 K
0.36 × 0.28 × 0.19 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.562, T _max = 0.746
16292 measured reflections
4404 independent reflections
4125 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.023
wR(F ²) = 0.062
S = 1.05
4404 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.63 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 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Click here for additional data file.^{(27KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813011793/ld2102sup1.cif

e-69-0o820-sup1.cif^{(27KB, cif)}

Click here for additional data file.^{(215.8KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813011793/ld2102Isup2.hkl

e-69-0o820-Isup2.hkl^{(215.8KB, hkl)}

Click here for additional data file.^{(6.4KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813011793/ld2102Isup3.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
C20—H20⋯O2ⁱ	0.95	2.36	3.314 (3)	177
C17—H17⋯I1ⁱⁱ	0.95	2.97	3.705 (2)	135

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

Acknowledgments

This work was supported by the Blue-Bio Industry Regional Innovation Center (RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan city.

supplementary crystallographic information

Comment

As a part of our continuing study of 5-iodo-3-phenylsulfinyl-1-benzofuran derivatives containing phenyl (Choi et al., 2009) and 4-fluorophenyl (Choi et al., 2012) substituents in 2-position, 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 0.007 (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 3.66 (7) and 82.37 (6)°, respectively. In the crystal structure (Fig. 2), molecules are linked by pairs of C—H···I hydrogen bonds into centrosymmetric dimers, which are further packed into stacks along the b axis by C—H···O hydrogen bonds (Table 1). In addition, the crystal packing (Fig. 2) exhibits a sulfinyl–sulfinyl interaction (Choi et al., 2008) interpreted as similar to a type-II carbonyl–carbonyl interaction (Allen et al., 1998), with S1···O2ⁱⁱⁱ and O2..S1ⁱⁱⁱ distance of 2.9627 (14) Å .

Experimental

3-Chloroperoxybenzoic acid (77%, 179 mg, 0.8 mmol) was added in small portions to a stirred solution of 2-(4-fluorophenyl)-5-iodo-7-methyl-3-phenylsulfanyl-1-benzofuran (322 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, 2:1 v/v) to afford the title compound as a colorless solid [yield 70%, m.p. 473–474 K; R_f = 0.74 (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 benzene at room temperature.