5-Cyclo­hexyl-2-methyl-3-phenyl­sulfinyl-1-benzofuran

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

doi:10.1107/S1600536811013705

. 2011 Apr 16;67(Pt 5):o1157. doi: 10.1107/S1600536811013705

5-Cyclohexyl-2-methyl-3-phenylsulfinyl-1-benzofuran

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

PMCID: PMC3089290 PMID: 21754465

Abstract

In the title compound, C₂₁H₂₂O₂S, the cyclohexyl ring adopts a chair conformation. The phenyl ring makes a dihedral angle of 84.80 (4)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked through weak intermolecular C—H⋯O hydrogen bonds.

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 structural studies of related 3-arylsulfinyl-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C₂₁H₂₂O₂S
M _r = 338.45
Triclinic,
a = 8.8532 (2) Å
b = 10.2011 (2) Å
c = 10.4752 (3) Å
α = 90.734 (1)°
β = 111.568 (1)°
γ = 97.127 (1)°
V = 871.25 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 173 K
0.35 × 0.25 × 0.16 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.650, T _max = 0.746
15560 measured reflections
4012 independent reflections
3481 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.106
S = 1.07
4012 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.26 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/S1600536811013705/zl2365sup1.cif

e-67-o1157-sup1.cif^{(20.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013705/zl2365Isup2.hkl

e-67-o1157-Isup2.hkl^{(196.6KB, 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—H15B⋯O2ⁱ	0.98	2.52	3.4516 (19)	159
C21—H21⋯O2ⁱⁱ	0.95	2.47	3.2793 (18)	144

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

supplementary crystallographic information

Comment

Many compounds having a benzofuran ring system have attracted much attention owing to their diverse 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 compounds widely occur in nature (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our study of the substituent effect on the solid state structures of 3-arylsulfinyl-2-methyl-1-benzofuran analogues (Choi et al., 2010, 2011), we report here on 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 (1) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring is in the chair form. The dihedral angle formed by the mean plane of the benzofuran ring and the phenyl ring is 84.80 (4)° . The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds; the first one between a methyl H atom and the O atom of the sulfinyl group (Table 1; C15—H15B···O2ⁱ), and the second one between a phenyl H atom and the O atom of the sulfinyl group (Table 1; C21—H21···O2ⁱⁱ).

Experimental

77% 3-chloroperoxybenzoic acid (269 mg, 1.2 mmol) was added in small portions to a stirred solution of 5-cyclohexyl-2-methyl-3-phenylsulfanyl-1-benzofuran (354 mg, 1.1 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 5h, 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, 2:1 v/v) to afford the title compound as a colorless solid [yield 71%, m.p. 406–407 K; R_f = 0.68 (hexane–ethyl acetate, 2:1 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.