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

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

doi:10.1107/S1600536811007859

. 2011 Mar 9;67(Pt 4):o804. doi: 10.1107/S1600536811007859

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

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

PMCID: PMC3099820 PMID: 21754092

Abstract

There are two independent molecules in the asymmetric unit of the title compound, C₁₅H₁₇ClO₂S, in each of which the cyclohexyl rings adopt chair conformations. In the crystal, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For the pharmacological 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 the structure of 5-bromo-3-cyclohexylsulfinyl-2-methyl-1-benzofuran, see: Choi et al. (2011 ▶).

Experimental

Crystal data

C₁₅H₁₇ClO₂S
M _r = 296.80
Monoclinic,
a = 12.0755 (2) Å
b = 9.0033 (2) Å
c = 13.9112 (2) Å
β = 108.667 (1)°
V = 1432.86 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 173 K
0.28 × 0.24 × 0.17 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.896, T _max = 0.932
14184 measured reflections
6583 independent reflections
6143 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.084
S = 1.03
6583 reflections
345 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.37 e Å⁻³
Absolute structure: Flack (1983 ▶), 2822 Friedel pairs
Flack parameter: 0.03 (4)

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 I. DOI: 10.1107/S1600536811007859/hg5004sup1.cif

e-67-0o804-sup1.cif^{(26.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007859/hg5004Isup2.hkl

e-67-0o804-Isup2.hkl^{(322.2KB, 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
C5—H5⋯O2ⁱ	0.95	2.54	3.469 (3)	166

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Many compounds containing a benzofuran ring exhibit interesting pharmacological properties such as antifungal, antitumor and antiviral, and antimicrobial 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 study of the substituent effect on the solid state structures of 3-cyclohexylsulfinyl-5-halo-2-methyl-1-benzofuran analogues (Choi et al., 2011), we report herein on the crystal structure of the title compound.

The title compound crystallizes as the non-centrosymmetric space group P2₁ in spite of having no asymmetric C atoms. The asymmetric unit of the title compound is shown in Fig. 1. There are two independent unique molecules [ A & B] in which the benzofuran unit is essentially planar, with a mean deviation of 0.007 (1) Å for A and 0.009 (1) Å for B, respectively, from the least-squares plane defined by the nine constituent atoms. The cyclohexyl rings are in the chair form. The molecular packing is stabilized by weak intermolecular C—H···O hydrogen bonds between a benzene H atom and the O atom of the sulfinyl group (Table 1; C5—H5···O2ⁱ).

Experimental

77% 3-chloroperoxybenzoic acid (269 mg, 1.2 mmol) was added in small portions to a stirred solution of 5-chloro-3-cyclohexylsulfanyl-2-methyl-1-benzofuran (309 mg, 1.1 mmol) in dichloromethane (40 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 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 76%, m.p. 382–383 K; R_f = 0.47 (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 aectone at room temperature.