5-Bromo-3-cyclo­hexyl­sulfonyl-2,7-dimethyl-1-benzofuran

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

doi:10.1107/S160053681101539X

. 2011 Apr 29;67(Pt 5):o1279. doi: 10.1107/S160053681101539X

5-Bromo-3-cyclohexylsulfonyl-2,7-dimethyl-1-benzofuran

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

PMCID: PMC3089243 PMID: 21754561

Abstract

In the title compound, C₁₆H₁₉BrO₃S, the cyclohexyl ring adopts a chair conformation. In the crystal, molecules are linked through weak C—H⋯O hydrogen bonds and Br⋯O contacts [3.211 (1) Å].

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-5-halo-2-methyl-1-benzofuran derivatives, see: Choi et al. (2011a ▶,b ▶). For a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C₁₆H₁₉BrO₃S
M _r = 371.28
Triclinic,
a = 6.6992 (2) Å
b = 8.4654 (2) Å
c = 14.1065 (3) Å
α = 101.773 (1)°
β = 99.283 (1)°
γ = 92.067 (1)°
V = 770.94 (3) Å³
Z = 2
Mo Kα radiation
μ = 2.81 mm⁻¹
T = 173 K
0.26 × 0.25 × 0.21 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.525, T _max = 0.591
13840 measured reflections
3542 independent reflections
3247 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.025
wR(F ²) = 0.066
S = 1.10
3542 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.59 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/S160053681101539X/lr2008sup1.cif

e-67-o1279-sup1.cif^{(19.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101539X/lr2008Isup2.hkl

e-67-o1279-Isup2.hkl^{(173.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681101539X/lr2008Isup3.cml

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
C10—H10B⋯O2ⁱ	0.98	2.55	3.384 (2)	143

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Many compounds containing a benzofuran skeleton have drawn much attention owing to 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-5-halo-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 0.004 (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 between a methyl H atom and the O atom of the sulfonyl group (Table 1; C10—H10B···O2ⁱⁱ). The crystal packing (Fig. 2) is further stabilized by a Br···O halogen-bonding between the bromine and the O atom of the sulfonyl group [Br1···O2ⁱ = 3.211 (1) Å, C4—Br1···O2ⁱ = 168.13 (6)°] (Politzer et al., 2007).

Experimental

77% 3-chloroperoxybenzoic acid (448 mg, 2.0 mmol) was added in small portions to a stirred solution of 5-bromo-3-cyclohexylsulfanyl-2,7-dimethyl-1-benzofuran (305 mg, 0.9 mmol) in dichloromethane (40 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, 4:1 v/v) to afford the title compound as a colorless solid [yield 72%, m.p. 440–441 K; R_f = 0.55 (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.