5-Cyclo­hexyl-3-(4-fluoro­phenyl­sulfon­yl)-2-methyl-1-benzofuran

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

doi:10.1107/S1600536811006593

. 2011 Mar 2;67(Pt 4):o767. doi: 10.1107/S1600536811006593

5-Cyclohexyl-3-(4-fluorophenylsulfonyl)-2-methyl-1-benzofuran

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

PMCID: PMC3099782 PMID: 21754061

Abstract

In the title compound, C₂₁H₂₁FO₃S, the cyclohexyl ring adopts a chair conformation. The 4-fluorophenyl ring makes a dihedral angle of 77.71 (4)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked through intermolecular C—H⋯O hydrogen bonds and aromatic π–π interactions between the furan rings of neighbouring molecules [centroid–centroid distance = 3.578 (2) Å].

Related literature

For the biological 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 our previous structural studies of related 3-(4-fluorophenylsulfonyl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010a ▶,b ▶).

Experimental

Crystal data

C₂₁H₂₁FO₃S
M _r = 372.44
Triclinic,
a = 9.2014 (3) Å
b = 10.2563 (4) Å
c = 11.1105 (4) Å
α = 80.564 (2)°
β = 66.317 (2)°
γ = 71.825 (2)°
V = 911.41 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 173 K
0.33 × 0.23 × 0.17 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.640, T _max = 0.746
15715 measured reflections
3967 independent reflections
3395 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.106
S = 1.03
3967 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.39 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/S1600536811006593/kp2311sup1.cif

e-67-0o767-sup1.cif^{(21.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811006593/kp2311Isup2.hkl

e-67-0o767-Isup2.hkl^{(194.4KB, hkl)}

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
C17—H17⋯O3ⁱ	0.93	2.59	3.2970 (19)	133
C20—H20⋯O1ⁱⁱ	0.93	2.60	3.285 (2)	131
C21—H21⋯O2ⁱⁱⁱ	0.93	2.42	3.3114 (19)	160

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

supplementary crystallographic information

Comment

Many compounds involving a benzofuran ring have attracted much attention owing to their interesting pharmacological properties such as antifungal, antimicrobial, antitumor and antiviral 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 program of the substituent effect on the solid state structures of 3-(4-fluorophenylsulfonyl)-2-methyl-1-benzofuran analogues (Choiet al., 2010a,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 0.013 (1) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring is in the chair conformation. The 4-fluorophenyl ring makes a dihedral angle of 77.71 (4)° with the mean plane of the benzofuran ring. The crystal packing (Fig. 2, Table 1) is stabilised by intermolecular C—H···O hydrogen bonds; the first one between a 4-fluorophenyl H atom and the oxygen of the O═S═O unit (Table 1; C17—H17···O3ⁱ), the second one between a 4-fluorophenyl H atom and the furan O atom (Table 1; C20—H20···O1ⁱ), the third one between a 4-fluorophenyl H atom and the oxygen of the O═S═O unit (Table 1; C21–H21···O2ⁱⁱⁱ). The crystal packing (Fig. 3) is also stabilised by an aromatic π–π interaction between the furan rings of adjacent molecules, with a Cg···Cgⁱdistance of 3.578 (2) Å (Cg is the centroid of the C1/C2/C7/O1/C8 furan ring).

Experimental

3-Chloroperoxybenzoic acid, 77% (426 mg, 1.9 mmol) was added in small portions to a stirred solution of 5-cyclohexyl-3-(4-fluorophenylsulfanyl)-2-methyl-1-benzofuran (306 mg, 0.9 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 6 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 colourless solid [yield 73%, m.p. 426–427 K; R_f = 0.68 (hexane–ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in benzene at room temperature.