3-Cyclo­hexyl­sulfonyl-2-methyl-5-propyl-1-benzofuran

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

doi:10.1107/S1600536811031023

. 2011 Aug 6;67(Pt 9):o2262. doi: 10.1107/S1600536811031023

3-Cyclohexylsulfonyl-2-methyl-5-propyl-1-benzofuran

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

PMCID: PMC3200801 PMID: 22058920

Abstract

In the title compound, C₁₈H₂₄O₃S, the cyclohexyl ring adopts a chair conformation. In the crystal, molecules are linked through weak intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions. In the propyl group, one C atom is disordered over two sites with site-occupancy factors of 0.546 (8) and 0.454 (8).

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-3-cyclohexylsulfonyl-2-methyl-1-benzofuran derivatives, see: Choi et al. (2011 ▶); Seo et al. (2011 ▶).

Experimental

Crystal data

C₁₈H₂₄O₃S
M _r = 320.43
Monoclinic,
a = 5.735 (2) Å
b = 23.713 (9) Å
c = 12.618 (5) Å
β = 100.389 (10)°
V = 1687.7 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 173 K
0.36 × 0.11 × 0.09 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.931, T _max = 0.982
14906 measured reflections
3644 independent reflections
2370 reflections with I > 2σ(I)
R _int = 0.081

Refinement

R[F ² > 2σ(F ²)] = 0.061
wR(F ²) = 0.158
S = 1.06
3644 reflections
204 parameters
18 restraints
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.39 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/S1600536811031023/xu5281sup1.cif

e-67-o2262-sup1.cif^{(29KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031023/xu5281Isup2.hkl

e-67-o2262-Isup2.hkl^{(178.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811031023/xu5281Isup3.cml

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
C13—H13⋯O3ⁱ	1.00	2.34	3.314 (3)	164
C18—H18A⋯O2ⁱⁱ	0.99	2.51	3.345 (4)	142
C12—H12C⋯Cgⁱⁱⁱ	0.98	2.84	3.659 (3)	141

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

supplementary crystallographic information

Comment

Recently, many compounds involving a benzofuran ring have received much attention due 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-3-cyclohexylsulfonyl-2-methyl-1-benzofuran analogues (Choi et al., 2011; 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 0.008 (2) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring is in the chair form. In the propyl group, C10 atom is disordered over two positions with site occupancy factors, from refinement of 0.546 (8) (part A) and 0.454 (8) (part B). The molecular packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds; the first one between a cyclohexyl H atom and the O atom of the sulfonyl group (Table 1; C13—H13···O3ⁱ), and the second one between a cyclohexyl H atom and the O atom of the sulfonyl group (Table 1; C18—H18A···O2ⁱⁱ). The crystal packing (Fig. 3) is further stabilized by intermolecular C—H···π interactions between a methyl H atom and the benzene ring (Table 1; C12—H12C···Cgⁱⁱⁱ, Cg is the centroid of the C2–C7 benzene ring).

Experimental

77% 3-Chloroperoxybenzoic acid (560 mg, 2.5 mmol) was added in small portions to a stirred solution of 3-cyclohexylsulfanyl-2-methyl-5-propyl-1-benzofuran (346 mg, 1.2 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 8 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, 4:1 v/v) to afford the title compound as a colorless solid [yield 70%, m.p. 393–395 K; R_f = 0.60 (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 benzene at room temperature.