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

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

doi:10.1107/S160053681103933X

. 2011 Sep 30;67(Pt 10):o2805. doi: 10.1107/S160053681103933X

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

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

PMCID: PMC3201441 PMID: 22058829

Abstract

In the title compound, C₁₄H₁₅ClO₃S, the cyclopenyl ring adopts an envelope conformation. In the crystal, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds into dual chains propagating in [100]. The dual chains arise from pairs of the same or different hydrogen bonds between adjacent molecules.

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 the crystal structures of related compounds, see: Seo et al. (2011a ▶,b ▶).

Experimental

Crystal data

C₁₄H₁₅ClO₃S
M _r = 298.77
Triclinic,
a = 7.4833 (8) Å
b = 8.7888 (9) Å
c = 10.9061 (10) Å
α = 66.919 (5)°
β = 82.848 (6)°
γ = 82.689 (6)°
V = 652.31 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.45 mm⁻¹
T = 173 K
0.39 × 0.27 × 0.22 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.844, T _max = 0.905
11884 measured reflections
3252 independent reflections
2721 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.143
S = 1.05
3252 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.73 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/S160053681103933X/cv5153sup1.cif

e-67-o2805-sup1.cif^{(24.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103933X/cv5153Isup2.hkl

e-67-o2805-Isup2.hkl^{(159.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681103933X/cv5153Isup3.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
C3—H3⋯O3ⁱ	0.95	2.51	3.420 (2)	160
C12—H12A⋯O2ⁱⁱ	0.99	2.59	3.557 (2)	167
C13—H13B⋯O3ⁱⁱ	0.99	2.61	3.516 (3)	153

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

supplementary crystallographic information

Comment

Recently, many compounds containing a benzofuran moiety have received much attention because of 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 ongoing study of benzofuran derivatives containing either 3-cyclopentylsulfinyl (Seo et al., 2011a) or 3-cyclopentylsulfonyl (Seo et al., 2011b) substituents, we report herein the crystal structure of the title compound (I).

In (I) (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.005 (2) Å from the least-squares plane defined by the nine constituent atoms. The cyclopentyl ring is in the envelope form. In the crystal structure (Fig. 2), weak intermolecular C—H···O hydrogen bonds (Table 1) link molecules into dual chains propagated in [100] (Fig. 2).

Experimental

77% 3-Chloroperoxybenzoic acid (560 mg, 2.5 mmol) was added in small portions to a stirred solution of 5-chloro-3-cyclopentylsulfanyl-2-methyl-1-benzofuran (320 mg, 1.2 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 70%, m.p. 412–413 K; R_f = 0.46 (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.