3-(4-Fluoro­phenyl­sulfon­yl)-5-iodo-2,7-dimethyl-1-benzofuran

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

doi:10.1107/S1600536811052792

. 2011 Dec 10;68(Pt 1):o96. doi: 10.1107/S1600536811052792

3-(4-Fluorophenylsulfonyl)-5-iodo-2,7-dimethyl-1-benzofuran

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

PMCID: PMC3254446 PMID: 22259594

Abstract

In the title compound, C₁₆H₁₂FIO₃S, the 4-fluorophenyl ring makes a dihedral angle of 72.31 (6)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds, and by an I⋯I contact [3.7764 (3) Å]. The crystal structure also exhibits a weak C—I⋯π [3.901 (3) Å] interaction and a slipped π–π interaction between the furan and benzene rings of neighbouring molecules [centroid–centroid distance = 3.845 (3), interplanar distance = 3.555 (3) and slippage = 1.465 (3) Å].

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 related structures, see: Choi et al. (2008 ▶, 2011 ▶).

Experimental

Crystal data

C₁₆H₁₂FIO₃S
M _r = 430.22
Triclinic,
a = 7.5839 (2) Å
b = 10.2443 (3) Å
c = 10.4651 (3) Å
α = 79.424 (1)°
β = 75.652 (1)°
γ = 80.361 (1)°
V = 767.94 (4) Å³
Z = 2
Mo Kα radiation
μ = 2.24 mm⁻¹
T = 173 K
0.32 × 0.30 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.534, T _max = 0.689
13962 measured reflections
3785 independent reflections
3585 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.022
wR(F ²) = 0.057
S = 1.08
3785 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.72 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/S1600536811052792/bh2405sup1.cif

e-68-00o96-sup1.cif^{(23.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052792/bh2405Isup2.hkl

e-68-00o96-Isup2.hkl^{(185.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811052792/bh2405Isup3.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
C12—H12⋯O3ⁱ	0.95	2.54	3.253 (2)	132
C15—H15⋯O2ⁱⁱ	0.95	2.52	3.294 (3)	139

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

supplementary crystallographic information

Comment

Recently, benzofuran derivatives have drawn much attention due to their valuable 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 benzofuran derivatives occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing study of benzofuran derivatives containing either 3-phenylsulfonyl (Choi et al., 2008) or 3-(4-fluorophenylsulfinyl) (Choi 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 0.007 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the 4-fluorophenyl ring and the mean plane of the benzofurn fragment is 72.31 (6)°. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds (see Table 1), and by an I···I contact at 3.7764 (3) Å. The crystal packing (Fig. 3) is further stabilized by a weak C—I···π interaction between the iodine and the benzene ring of an adjacent molecule, with a C4—I1···Cg2^v [3.901 (3) Å] (Cg2 is the centroid of the C2···C7 benzene ring). The crystal packing (Fig. 3) is also exhibits a weak slipped π–π interaction between the furan and benzene rings of adjacent molecules, with a Cg1···Cg2^iv distance of 3.845 (3) Å and an interplanar distance of 3.555 (3) Å resulting in a slippage of 1.465 (3) Å (Cg1 is the centroid of the C1/C2/C7/O1/C8 furan ring).

Experimental

77% 3-chloroperoxybenzoic acid (381 mg, 1.7 mmol) was added in small portions to a stirred solution of 3-(4-fluorophenylsulfanyl)-5-iodo-2,7-dimethyl-1-benzofuran (318 mg, 0.8 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 8 h, 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 71%, m.p. 430–431 K; R_f = 0.53 (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.