5-Chloro-2-(4-methyl­phen­yl)-3-methyl­sulfinyl-1-benzo­furan

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S1600536813018400

. 2013 Jul 6;69(Pt 8):o1213. doi: 10.1107/S1600536813018400

5-Chloro-2-(4-methylphenyl)-3-methylsulfinyl-1-benzofuran

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

PMCID: PMC3793721 PMID: 24109308

Abstract

In the title compound, C₁₆H₁₃ClO₂S, the dihedral angle between the mean plane [r.m.s. deviation = 0.004 (2) Å] of the benzofuran ring system and the 4-methylphenyl ring is 29.25 (8)°. In the crystal, inversion dimers linked by pairs of weak C—H⋯O interactions generate R ₂ ²(14) loops.

Related literature

For the pharmacological 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 the crystal structures of related compounds, see: Choi et al. (2007 ▶, 2009 ▶). graphic file with name e-69-o1213-scheme1.jpg

Experimental

Crystal data

C₁₆H₁₃ClO₂S
M _r = 304.77
Triclinic,
a = 8.0694 (8) Å
b = 8.0763 (8) Å
c = 11.4208 (11) Å
α = 90.185 (6)°
β = 96.280 (6)°
γ = 111.701 (6)°
V = 686.63 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 173 K
0.35 × 0.34 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.865, T _max = 0.958
12808 measured reflections
3423 independent reflections
3021 reflections with I > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.103
S = 1.05
3423 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.28 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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813018400/nk2211sup1.cif

e-69-o1213-sup1.cif^{(23.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813018400/nk2211Isup2.hkl

e-69-o1213-Isup2.hkl^{(167.9KB, hkl)}

Click here for additional data file.^{(5.2KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813018400/nk2211Isup3.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
C14—H14⋯O2ⁱ	0.95	2.54	3.436 (2)	158

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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

Many compounds having a benzofuran moiety 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 continuing study of 5-chloro-3-methylsulfinyl-1-benzofuran derivatives containing phenyl (Choi et al., 2007) and 4-fluorophenyl (Choi et al., 2009) 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 0.004 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the mean plane of the benzofuran ring system and the 4-methylphenyl ring is 29.25 (8)°. In the crystal structure, molecules are connected by weak C—H···O hydrogen bonds (Table 1), resulting in a three-dimensional network.

Experimental

3-Chloroperoxybenzoic acid (77%, 269 mg, 1.2 mmol) was added in small portions to a stirred solution of 5-chloro-2-(4-methylphenyl)-3-methylsulfanyl-1-benzofuran (317 mg, 1.1 mmol) in dichloromethane (40 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 70%, m.p. 459–460 K; R_f = 0.49 (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.