3-Cyclo­hexyl­sulfonyl-2,5-dimethyl-1-benzofuran

Pil Ja Seo; Hong Dae Choi; Uk Lee

doi:10.1107/S160053681101498X

. 2011 Apr 29;67(Pt 5):o1225. doi: 10.1107/S160053681101498X

3-Cyclohexylsulfonyl-2,5-dimethyl-1-benzofuran

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

PMCID: PMC3089093 PMID: 21754523

Abstract

In the title compound, C₁₆H₂₀O₃S, the cyclohexyl ring adopts a chair conformation and the arylsulfonyl unit is in the equatorial position. In the crystal, molecules are linked through weak intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions.

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-cyclohexylsulfonyl-2-methyl-1-benzofuran derivatives, see: Choi et al. (2011a ▶,b ▶).

Experimental

Crystal data

C₁₆H₂₀O₃S
M _r = 292.38
Monoclinic,
a = 5.6854 (3) Å
b = 21.2391 (13) Å
c = 12.3944 (7) Å
β = 99.295 (3)°
V = 1477.01 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 173 K
0.30 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.643, T _max = 0.746
13128 measured reflections
3228 independent reflections
2477 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.106
S = 1.05
3228 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.34 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/S160053681101498X/gk2370sup1.cif

e-67-o1225-sup1.cif^{(19KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101498X/gk2370Isup2.hkl

e-67-o1225-Isup2.hkl^{(158.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681101498X/gk2370Isup3.cml

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
C11—H11⋯O2ⁱ	1.00	2.31	3.273 (2)	161
C12—H12B⋯O3ⁱⁱ	0.99	2.57	3.443 (2)	146
C10—H10C⋯Cgⁱⁱⁱ	0.99	2.75	3.556 (2)	140

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

Acknowledgments

This work was supported by Dong-eui University (grant No. 2011AA098).

supplementary crystallographic information

Comment

Many compounds containing a benzofuran ring have drawn 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 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-cyclohexylsulfonyl-2-methyl-1-benzofuran analogues (Choi et al., 2011a,b), 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 0.006 (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 intermolecular C–H···O hydrogen bonds; the first one between a cyclohexyl H atom and the O atom of the sulfonyl group (Table 1; C11–H11···O2ⁱ), and the second one between a cyclohexyl H atom and the O atom of the sulfonyl group (Table 1; C12–H12B···O3ⁱⁱ). The crystal packing (Fig. 2) is further stabilized by intermolecular C–H···π interactions between a methyl H atom and the benzene ring (Table 1; C10–H10C···Cgⁱⁱⁱ, Cg is the centroid of the C2-C7 benzene ring).

Experimental

77% 3-chloroperoxybenzoic acid (515 mg, 2.3 mmol) was added in small portions to a stirred solution of 3-cyclohexylsulfanyl-2,5-dimethyl-1-benzofuran (286 mg, 1.1 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 colorless solid [yield 72%, m.p. 417-418 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 ethyl acetate at room temperature.