5-Chloro-2-(4-chloro­phen­yl)-7-methyl-3-methyl­sulfinyl-1-benzofuran

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

doi:10.1107/S1600536810006823

. 2010 Feb 27;66(Pt 3):o706. doi: 10.1107/S1600536810006823

5-Chloro-2-(4-chlorophenyl)-7-methyl-3-methylsulfinyl-1-benzofuran

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

PMCID: PMC2983503 PMID: 21580444

Abstract

In the title compound, C₁₆H₁₂Cl₂O₂S, the O atom and the methyl group of the methylsulfinyl substituent lie on opposite sides of the plane through the benzofuran fragment. The 4-chlorophenyl ring is rotated out of the benzofuran plane, as indicated by the dihedral angle of 15.91 (4)°. In the crystal, molecules are linked into chains along the b axis by weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For the crystal structures of similar 2-(4-fluorophenyl)-5-halo-3-methylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2009 ▶, 2010a ▶,b ▶). For the biological activity of benzofuran compounds, see: Aslam et al. (2006 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶).

Experimental

Crystal data

C₁₆H₁₂Cl₂O₂S
M _r = 339.22
Triclinic,
a = 7.538 (2) Å
b = 9.734 (2) Å
c = 11.277 (3) Å
α = 72.525 (2)°
β = 88.846 (3)°
γ = 70.058 (2)°
V = 738.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.58 mm⁻¹
T = 173 K
0.50 × 0.50 × 0.45 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.760, T _max = 0.780
6331 measured reflections
3170 independent reflections
2879 reflections with I > 2σ(I)
R _int = 0.017

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.089
S = 1.03
3170 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.33 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/S1600536810006823/hg2648sup1.cif

e-66-0o706-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810006823/hg2648Isup2.hkl

e-66-0o706-Isup2.hkl^{(155.5KB, hkl)}

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
C15—H15A⋯O2ⁱ	0.96	2.52	3.216 (2)	130

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Compounds containing benzofuran skeleton display significant biological activities such as antifungal (Aslam et al., 2006), antitumor and antiviral (Galal et al., 2009), antimicrobial (Khan et al., 2005) properties. These compounds are widely occurring in nature (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing studies of the effect of side chain substituents on the solid state structures of 2-(4-fluorophenyl)-5-halo-3-methylsulfinyl-1-benzofuran analogues (Choi et al., 2009, 2010a,b), we report the crystal structure of the title compound (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.013 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the plane of the benzofuran and the 4-chlorophenyl ring is 15.91 (4)°. The crystal packing (Fig. 2) is stabilized by a weak intermolecular C—H···O hydrogen bond between the methyl H atom and the oxygen of the S═O unit, with a C15—H15A···O2ⁱ (Table 1).

Experimental

77% 3-Chloroperoxybenzoic acid (247 mg, 1.1 mmol) was added in small portions to a stirred solution of 5-chloro-2-(4-chlorophenyl)-7-methyl-3-methylsulfanyl-1-benzofuran (323 mg, 1.0 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, 1:1 v/v) to afford the title compound as a colorless solid [yield 79%, m.p. 456–457 K; R_f = 0.62 (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 tetrahydrofuran at room temperature.