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

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

doi:10.1107/S1600536811008270

. 2011 Mar 9;67(Pt 4):o828. doi: 10.1107/S1600536811008270

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

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

PMCID: PMC3099810 PMID: 21754112

Abstract

In the title compound, C₁₅H₁₇ClO₃S, the cyclohexyl ring adopts a chair conformation. In the crystal, molecules are linked through weak intermolecular C—H⋯O 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-chloro-2-methyl-1-benzofuran derivatives, see: Choi et al. (2008 ▶, 2010 ▶).

Experimental

Crystal data

C₁₅H₁₇ClO₃S
M _r = 312.80
Monoclinic,
a = 14.3135 (2) Å
b = 9.2829 (2) Å
c = 11.3433 (2) Å
β = 107.566 (1)°
V = 1436.91 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.42 mm⁻¹
T = 173 K
0.29 × 0.18 × 0.11 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.891, T _max = 0.954
13251 measured reflections
3287 independent reflections
2856 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.093
S = 1.07
3287 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.37 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/S1600536811008270/bh2340sup1.cif

e-67-0o828-sup1.cif^{(18.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008270/bh2340Isup2.hkl

e-67-0o828-Isup2.hkl^{(161.3KB, hkl)}

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

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

Cg is the centroid of the benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O3ⁱ	0.95	2.54	3.2630 (19)	133
C10—H10⋯O2ⁱⁱ	1.00	2.42	3.3899 (19)	162
C9—H9C⋯Cgⁱⁱⁱ	0.98	2.69	3.577 (2)	151

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

supplementary crystallographic information

Comment

Many compounds containing a benzofuran ring exhibit 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 3-arylsulfonyl-5-chloro-2-methyl-1-benzofuran analogues (Choi et al., 2008, 2010), 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 0.009 (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 intermolecular C–H···O hydrogen bonds; the first one between a benzene H atom and the O atom of the sulfonyl unit (Table 1: C6–H6···O3ⁱ), and the second one between a cyclohexyl H atom and the O atom of the sulfonyl unit (Table 1: C10–H10···O2ⁱⁱ). The crystal packing (Fig. 2) is further stabilized by intermolecular C–H···π interactions between a methyl H atoms and the benzene rings (Table 1: C9–H9C···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 5-chloro-3-cyclohexylsulfanyl-2-methyl-1-benzofuran (389 mg, 1.1 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 5 h, 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 73%, m.p. 440-441 K; R_f = 0.63 (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.