5-Iodo-2,7-dimethyl-3-(4-methyl­phenyl­sulfon­yl)-1-benzofuran

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S1600536812037932

. 2012 Sep 8;68(Pt 10):o2893. doi: 10.1107/S1600536812037932

5-Iodo-2,7-dimethyl-3-(4-methylphenylsulfonyl)-1-benzofuran

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

PMCID: PMC3470245 PMID: 23125689

Abstract

In the title compound, C₁₇H₁₅IO₃S, the 4-methylphenyl ring makes a dihedral angle of 76.95 (5)° with the mean plane [r.m.s. deviation = 0.019 (2) Å] of the benzofuran fragment. In the crystal, molecules are linked via pairs of C—H⋯O hydrogen bonds, forming inversion dimers. These dimers are connected by slipped π–π interactions between the benzene rings of neighbouring molecules [centroid–centroid distance = 3.671 (3) Å and slippage = 1.049 (3) Å].

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2008 ▶); Seo et al. (2012 ▶).

Experimental

Crystal data

C₁₇H₁₅IO₃S
M _r = 426.25
Monoclinic,
a = 11.5480 (5) Å
b = 9.9394 (4) Å
c = 14.8911 (6) Å
β = 107.611 (1)°
V = 1629.10 (12) Å³
Z = 4
Mo Kα radiation
μ = 2.10 mm⁻¹
T = 173 K
0.33 × 0.27 × 0.22 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.634, T _max = 0.746
16012 measured reflections
4075 independent reflections
3619 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.027
wR(F ²) = 0.070
S = 1.05
4075 reflections
202 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.91 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/S1600536812037932/im2395sup1.cif

e-68-o2893-sup1.cif^{(25.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037932/im2395Isup2.hkl

e-68-o2893-Isup2.hkl^{(199.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812037932/im2395Isup3.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
C16—H16⋯O3ⁱ	0.95	2.58	3.246 (2)	127

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Symmetry code: (i) Inline graphic .

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 ongoing study of 5-iodo-2,7-dimethyl-benzofuran derivatives containing either phenyl-sulfonyl (Choi et al., 2008) or 4-fluorophenyl-sulfonyl (Seo et al., 2012) substituents in 3-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 0.019 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 4-methylphenyl ring and the mean plane of the benzofuran fragment is 76.95 (5)°. In the crystal structure, molecules are linked via pairs of C—H···O hydrogen bonds (Fig. 2 & Table 1), forming inversion dimers. These dimers are connected by slipped π–π interactions between the benzene rings of neighbouring molecules, with a Cg···Cgⁱⁱ distance of 3.671 (3) Å and an interplanar distance of 3.518 (2) Å resulting in a slippage of 1.049 (3) Å (Fig. 2, Cg is the centroid of the C2–C7 benzene ring).

Experimental

3-Chloroperoxybenzoic acid (77%, 381 mg, 1.7 mmol) was added in small portions to a stirred solution of 5-iodo-2,7-dimethyl-3-(4-methylphenylsulfanyl)-benzofuran (315 mg, 0.8 mmol) in dichloromethane (50 mL) at 273 K. After being stirred at room temperature for 10h, the mixture was washed with saturated sodium bicarbonate solution, the organic layer was separated and dried over magnesium sulfate. After filtration the solution was concentrated at reduced pressure. The residue was purified by column chromatography (benzene ) to afford the title compound as a colorless solid [yield 68%, m.p. 483–484 K; R_f = 0.56 (benzene)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in acetone at room temperature.