5-Cyclo­hexyl-3-methyl­sulfinyl-2-phenyl-1-benzofuran

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

doi:10.1107/S1600536810054358

. 2011 Jan 8;67(Pt 2):o281. doi: 10.1107/S1600536810054358

5-Cyclohexyl-3-methylsulfinyl-2-phenyl-1-benzofuran

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

PMCID: PMC3051680 PMID: 21522973

Abstract

In the title compound, C₂₁H₂₂O₂S, the cyclohexyl ring adopts a chair conformation while the phenyl ring makes a dihedral angle of 33.38 (5)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked through weak intermolecular C—H⋯O and C—H⋯π interactions.

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-methylsulfinyl-2-phenyl-1-benzofuran derivatives, see: Choi et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

C₂₁H₂₂O₂S
M _r = 338.45
Monoclinic,
a = 9.9864 (2) Å
b = 17.1899 (3) Å
c = 11.0792 (2) Å
β = 113.540 (1)°
V = 1743.64 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 173 K
0.30 × 0.23 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.944, T _max = 0.972
16429 measured reflections
4009 independent reflections
3171 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.103
S = 1.04
4009 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.40 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/S1600536810054358/xu5130sup1.cif

e-67-0o281-sup1.cif^{(20.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810054358/xu5130Isup2.hkl

e-67-0o281-Isup2.hkl^{(196.5KB, 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
C5—H5⋯O2ⁱ	0.95	2.50	3.429 (2)	167
C21—H21B⋯O2ⁱⁱ	0.98	2.33	3.290 (2)	165
C19—H19⋯Cgⁱⁱ	0.95	2.59	3.392 (2)	142

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

supplementary crystallographic information

Comment

Many compounds possessing a benzofuran ring system have received much attention in view of their important pharmacological properties such as antifungal, antimicrobial, antitumor and antiviral activities (Aslam et al., 2006; Galal et al., 2009; Khan et al., 2005). These compounds widely occur in nature (Akgul & Anil, 2003; Soekamto et al., 2003). As part of our ongoing program of the substituent effect on the solid state structures of 3-methylsulfinyl-2-phenyl-1-benzofuran analogues (Choi et al., 2007, 2008), 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 0.025 (1) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring is in the chair form. The phenyl ring makes a dihedral angle of33.38 (5)° with the mean plane of the benzofuran ring. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds; the first one between a benzene H atom and the oxygen of the S═O unit (Table 1; C5—H5···O2ⁱ), and the second one between a methyl H atom and the oxygen of the S═O unit (Table 1; C21—H21B···O2ⁱⁱ). The crystal packing (Fig. 2) is further stabilized by an intermolecular C–H···π interaction between the phenyl H atom and the benzene ring (Table 1; C19—H19···Cgⁱⁱ, Cg is the centroid of the C2–C7 benzene ring).

Experimental

77% 3-Chloroperoxybenzoic acid (269 mg, 1.2 mmol) was added in small portions to a stirred solution of 5-cyclohexyl-3-methylsulfanyl-2-phenyl-1-benzofuran (386 mg, 1.2 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 4 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, 2:1 v/v) to afford the title compound as a colorless solid [yield 71%, m.p. 445-446 K; R_f = 0.55 (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 acetone at room temperature.