3-Cyclo­hexyl­sulfonyl-5-isopropyl-2-methyl-1-benzofuran

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

doi:10.1107/S1600536811007215

. 2011 Mar 2;67(Pt 4):o749. doi: 10.1107/S1600536811007215

3-Cyclohexylsulfonyl-5-isopropyl-2-methyl-1-benzofuran

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

PMCID: PMC3100029 PMID: 21754046

Abstract

In the title compound, C₁₈H₂₄O₃S, the cyclohexyl ring adopts a chair conformation. In the crystal, molecules are linked through weak non-classical intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions.

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 3-arylsulfonyl-5-isopropyl-2-methyl-1-benzofuran derivatives, see: Choi et al. (2008 ▶, 2010 ▶).

Experimental

Crystal data

C₁₈H₂₄O₃S
M _r = 320.44
Monoclinic,
a = 5.7117 (1) Å
b = 23.5045 (4) Å
c = 12.7980 (2) Å
β = 102.080 (1)°
V = 1680.09 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 173 K
0.26 × 0.25 × 0.22 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.949, T _max = 0.957
15706 measured reflections
3870 independent reflections
3124 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.118
S = 1.05
3870 reflections
202 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.49 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/S1600536811007215/rk2267sup1.cif

e-67-0o749-sup1.cif^{(20.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007215/rk2267Isup2.hkl

e-67-0o749-Isup2.hkl^{(189.7KB, hkl)}

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

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2ⁱ	1.00	2.33	3.3030 (19)	165
C14—H14A⋯O3ⁱⁱ	0.99	2.58	3.424 (2)	143
C10—H10C⋯Cgⁱ	0.98	2.71	3.548 (2)	144

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

supplementary crystallographic information

Comment

Many compounds having a benzofuran skeleton exhibit diverse 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 3-arylsulfonyl-5-isopropyl-2-methyl-1-benzofuran analogues (Choi et al., 2008, 2010), we report herein the molecular and crystal structures of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.009 (1) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring is in the chair form. The molecular packing (Fig. 2) is stabilized by weak non-classical intermolecular C–H···O hydrogen bonds; the first one between a cyclohexyl H atom and the oxygen of the O═S═O unit (Table 1; C13—H13···O2ⁱ), the second one between a cyclohexyl H atom and the oxygen of the O═S═O unit (Table 1; C14—H14A···O3ⁱⁱ). The crystal packing (Fig. 2) is further stabilized by intermolecular C–H···π interactions between a methyl H atom of the isopropyl group and the benzene ring.

Experimental

The 3-chloroperoxybenzoic acid (77%, 560 mg, 2.5 mmol) was added in small portions to a stirred solution of 3-cyclohexylsulfanyl-5-isopropyl-2-methyl-1-benzofuran (346 mg, 1.2 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 (hexane–ethyl acetate, 4:1 v/v) to afford the title compound as a colourless solid [yield 78%, m.p. 467–468 K; R_f = 0.66 (hexane–ethyl acetate, 4:1 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.