5-Chloro-3-ethyl­sulfinyl-2-(4-iodo­phen­yl)-1-benzofuran

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

doi:10.1107/S1600536810033581

. 2010 Aug 28;66(Pt 9):o2449. doi: 10.1107/S1600536810033581

5-Chloro-3-ethylsulfinyl-2-(4-iodophenyl)-1-benzofuran

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

PMCID: PMC3008065 PMID: 21588770

Abstract

In the title compound, C₁₆H₁₂ClIO₂S, the 4-iodophenyl ring is rotated out of the benzofuran plane by 9.4 (1)°. In the crystal structure, intermolecular C—H⋯π interactions and short intermolecular I⋯O contacts [3.142 (2) Å] are observed.

Related literature

For the crystal structures of related 3-ethylsulfinyl-2-(4-iodophenyl)-1-benzofuran derivatives, see: Choi et al. (2010a ▶,b ▶). For a review on halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C₁₆H₁₂ClIO₂S
M _r = 430.67
Monoclinic,
a = 11.9782 (3) Å
b = 10.4604 (3) Å
c = 12.9624 (4) Å
β = 107.827 (1)°
V = 1546.16 (8) Å³
Z = 4
Mo Kα radiation
μ = 2.38 mm⁻¹
T = 173 K
0.35 × 0.25 × 0.14 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.514, T _max = 0.746
14190 measured reflections
3549 independent reflections
3252 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.025
wR(F ²) = 0.054
S = 1.67
3549 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.75 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 datablocks global, I. DOI: 10.1107/S1600536810033581/nc2194sup1.cif

e-66-o2449-sup1.cif^{(18.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033581/nc2194Isup2.hkl

e-66-o2449-Isup2.hkl^{(174.1KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg is the centroid of the C2–C7 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯Cgⁱ	0.97	3.04	3.750 (3)	131

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

As a part of our ongoing studies of the substituent effect on the solid state structures of 3-ethylsulfinyl-2-(4-iodophenyl)-1-benzofuran analogues (Choi et al., 2010a,b), we report the crystal structure of the title compound (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.015 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the benzofuran plane and the 4-iodophenyl ring is 9.4 (1)° (Fig. 1). In the crystal structure weak C—H···π interactions between the methylene H atom of the ethyl group and the benzene ring of an adjacent benzofuran ring is observed (Fig. 2 and Tab. 1). In addition, a short I···O contact is observed [I···O2ⁱⁱ = 3.142 (2)Å; C12—I···O2ⁱⁱ = 158.24 (7)°] which indicate a weak interaction (Politzer et al., 2007).

Experimental

3-chloroperoxybenzoic acid (77%) (202 mg, 0.9 mmol) was added in small portions to a stirred solution of 5-chloro-3-ethylsulfanyl-2-(4-iodophenyl)-1-benzofuran (373 mg, 0.9 mmol) in dichloromethane (30 mL) at 273 K. The mixture was stirred for 5 h at room temperature, 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, 1:1 v/v) to afford the title compound as a colorless solid [yield 76%, m.p. 439–440 K; R_f = 0.56 (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 acetone at room temperature.