5-Bromo-3-cyclo­pentyl­sulfinyl-2-methyl-1-benzofuran

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

doi:10.1107/S1600536811017120

. 2011 May 11;67(Pt 6):o1386. doi: 10.1107/S1600536811017120

5-Bromo-3-cyclopentylsulfinyl-2-methyl-1-benzofuran

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

PMCID: PMC3120517 PMID: 21754775

Abstract

In the title compound, C₁₄H₁₅BrO₂S, the cyclopentyl ring adopts an envelope conformation. In the cyclopentyl ring, two adjacent C atoms are disordered over two sets of sites with site-occupancy factors of 0.618 (11) and 0.382 (11). In the crystal, molecules are linked through weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For the biological 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-bromo-3-cyclohexylsulfinyl-2-methyl-1-benzofuran derivatives, see: Choi et al. (2011a ▶,b ▶).

Experimental

Crystal data

C₁₄H₁₅BrO₂S
M _r = 327.23
Monoclinic,
a = 9.4166 (6) Å
b = 9.5369 (7) Å
c = 15.1662 (11) Å
β = 100.033 (4)°
V = 1341.17 (16) Å³
Z = 4
Mo Kα radiation
μ = 3.21 mm⁻¹
T = 173 K
0.31 × 0.24 × 0.13 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.531, T _max = 0.746
12376 measured reflections
3098 independent reflections
2567 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.094
S = 1.06
3098 reflections
182 parameters
83 restraints
H-atom parameters constrained
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.64 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/S1600536811017120/qk2009sup1.cif

e-67-o1386-sup1.cif^{(25KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017120/qk2009Isup2.hkl

e-67-o1386-Isup2.hkl^{(152KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811017120/qk2009Isup3.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⋯O2ⁱ	0.95	2.46	3.392 (3)	169

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Recently, many compounds having a benzofuran skeleton have attracted much attention due to their 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 benzofuran derivatives occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As part of our ongoing program of the substituent effect on the solid state structures of 5-bromo-3-cyclohexylsulfinyl-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 0.012 (2) Å from the least-squares plane defined by the nine constituent atoms. The cyclopentyl ring is in the envelope form. In the cyclopentyl ring, two C atoms (C12 & C13) are disordered over two positions with site-occupancy factors, from refinement of 0.62 (1) (part A) and 0.38 (1) (part B). The crystal packing is stabilized by weak intermolecular C—H···O hydrogen bonds; the first one between a benzene H atom and the O atom of the sulfinyl group (Table 1; C3—H3···O2ⁱ), and the second one between a cyclopentyl H atom and the furan O atom (Table 1; C11—H11C···O1ⁱⁱ).

Experimental

77% 3-chloroperoxybenzoic acid (269 mg, 1.2 mmol) was added in small portions to a stirred solution of 5-bromo-3-cyclopentylsulfanyl-2-methyl-1-benzofuran (373 mg, 1.2 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 4h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over anhydrous magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane–ethyl acetate, 1:1 v/v) to afford the title compound as a colorless solid [yield 71%, m.p. 405–406 K; R_f = 0.66 (hexane–ethyl acetate, 1:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.