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

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

doi:10.1107/S1600536811007872

. 2011 Mar 9;67(Pt 4):o805. doi: 10.1107/S1600536811007872

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

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

PMCID: PMC3099851 PMID: 21754093

Abstract

In the title compound, C₂₁H₂₈O₃S, the benzofuran unit is essentially planar, with a mean deviation of 0.016 (1) Å from the least-squares plane defined by the nine constituent atoms. Both cyclohexane rings adopt chair conformations.

Related literature

For the pharmacological 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 ▶). For structural studies of related 2-aryl-5-cyclohexyl-3-methylsufinyl-1-benzofuran derivatives, see: Choi et al. (2011a ▶,b ▶).

Experimental

Crystal data

C₂₁H₂₈O₃S
M _r = 360.49
Triclinic,
a = 6.8819 (2) Å
b = 10.7244 (3) Å
c = 13.3533 (4) Å
α = 77.132 (2)°
β = 83.165 (2)°
γ = 87.597 (2)°
V = 953.83 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 298 K
0.20 × 0.17 × 0.17 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.963, T _max = 0.969
17113 measured reflections
4397 independent reflections
3140 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.136
S = 1.06
4397 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.32 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 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536811007872/nk2090sup1.cif

e-67-0o805-sup1.cif^{(22KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007872/nk2090Isup2.hkl

e-67-0o805-Isup2.hkl^{(215.4KB, hkl)}

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

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

Cg is the centroid of the C1/C2/C7/O1/C8 furan ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14B⋯Cgⁱ	0.97	2.80	3.649 (3)	147

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Many compounds involving a benzofuran ring have attracted interesting pharmacological properties such as antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2006, Galal et al., 2009, Khan et al., 2005). These compounds occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing study of the substituent effect on the solid state structures of 2-aryl-5-cyclohexyl-3-methylsufinyl-1-benzofuran analogues (Choi et al., 2011a, b), we report herein 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 0.016 (1) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexane rings in each are in the chair form.

The molecular packing is stabilized by weak intermolecular C—H···π interactions between a cyclohexyl H atom in the 5-position and the furan ring (Table 1).

Experimental

77% 3-chloroperoxybenzoic acid (448 mg, 2.0 mmol) was added in small portions to a stirred solution of 5-cyclohexyl-3-cyclohexylsulfanyl-2-methyl-1-benzofuran (295 mg, 0.9 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 6h, 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 (benzene) to afford the title compound as a colorless solid [yield 79%, m.p. 378–379 K; R_f = 0.65 (benzene)]. 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.