5-Cyclo­pentyl-2-methyl-3-phenyl­sulfonyl-1-benzofuran

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

doi:10.1107/S160053681103042X

. 2011 Aug 2;67(Pt 9):o2223. doi: 10.1107/S160053681103042X

5-Cyclopentyl-2-methyl-3-phenylsulfonyl-1-benzofuran

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

PMCID: PMC3200710 PMID: 22065504

Abstract

In the title compound, C₂₀H₂₀O₃S, the cyclopentyl ring adopts an envelope conformation. The phenyl ring makes a dihedral angle of 81.40 (6)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by 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 5-alkyl-2-methyl-3-phenylsulfonyl-1-benzofuran derivatives, see: Choi et al. (2008a ▶,b ▶); Seo et al. (2011 ▶).

Experimental

Crystal data

C₂₀H₂₀O₃S
M _r = 340.42
Monoclinic,
a = 6.2999 (9) Å
b = 15.001 (2) Å
c = 17.743 (2) Å
β = 92.011 (3)°
V = 1675.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 173 K
0.27 × 0.10 × 0.08 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.946, T _max = 0.983
15497 measured reflections
3616 independent reflections
2869 reflections with I > 2σ(I)
R _int = 0.065

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.130
S = 1.04
3616 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.44 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 datablock(s) global, I. DOI: 10.1107/S160053681103042X/zl2391sup1.cif

e-67-o2223-sup1.cif^{(26.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103042X/zl2391Isup2.hkl

e-67-o2223-Isup2.hkl^{(177.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681103042X/zl2391Isup3.cml

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

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

Cg is the centroid of the C1/C2/C7/O1/C8 furan ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯O3ⁱ	0.99	2.52	3.493 (3)	166
C17—H17⋯O3ⁱⁱ	0.95	2.49	3.183 (3)	129
C10—H10B⋯Cgⁱⁱⁱ	0.99	2.68	3.604 (3)	156

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

supplementary crystallographic information

Comment

Recently, many compounds involving a benzofuran skeleton have drawn much attention owing to their valuable 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 benzofuran derivatives occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our continuing studies of the substituent effect on the solid state structures of 5-alkyl-2-methyl-3-phenylsulfonyl-1-benzofuran analogues (Choi et al., 2008a,b; Seo et al., 2011), 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 0.020 (2) Å from the least-squares plane defined by the nine constituent atoms. The cyclopentyl ring is in the envelope form. The dihedral angle formed by the phenyl ring and the mean plane of the benzofuran fagment is 81.40 (6)°. The molecular packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds; the first one between a cyclopentyl H atom and the O atom of the sulfonyl group (Table 1; C12—H12A···O3ⁱ), and the second one between a phenyl H atom and the O atom of the sulfonyl group (Table 1; C17—H17···O3ⁱⁱ). The crystal packing (Fig. 3) is further stabilized by intermolecular C—H···π interactions between a cyclopentyl H atom and the furan ring (Table 1; C10—H10B···Cgⁱⁱⁱ, Cg is the centroid of the C1/C2/C7/O1/C8 furan ring).

Experimental

77% 3-chloroperoxybenzoic acid (448 mg, 2.0 mmol) was added in small portions to a stirred solution of 5-cyclopentyl-2-methyl-3-phenylsulfanyl-1-benzofuran (277 mg, 0.9 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 8h, 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. 418–419 K; Rf = 0.48 (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.