5-Cyclo­hexyl-2-methyl-3-(4-methyl­phenyl­sulfin­yl)-1-benzofuran

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S1600536812008409

. 2012 Mar 3;68(Pt 4):o947. doi: 10.1107/S1600536812008409

5-Cyclohexyl-2-methyl-3-(4-methylphenylsulfinyl)-1-benzofuran

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

PMCID: PMC3343928 PMID: 22590009

Abstract

In the title compound, C₂₂H₂₄O₂S, the cyclohexyl ring adopts a chair conformation. The 4-methylphenyl ring makes a dihedral angle of 81.60 (5)° with the mean plane [r.m.s. deviation = 0.004 (1) Å] of the benzofuran fragment. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds and weak π–π interactions between the furan rings of adjacent molecules [centroid–centroid distance = 3.545 (2) Å, interplanar distance = 3.489 (2) Å and slippage = 0.628 (2) Å.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2011 ▶, 2012 ▶).

Experimental

Crystal data

C₂₂H₂₄O₂S
M _r = 352.47
Monoclinic,
a = 16.6086 (4) Å
b = 8.8344 (2) Å
c = 13.0330 (3) Å
β = 104.064 (1)°
V = 1854.97 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 173 K
0.37 × 0.25 × 0.23 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.934, T _max = 0.958
16901 measured reflections
4265 independent reflections
3545 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.128
S = 1.06
4265 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.31 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/S1600536812008409/gk2461sup1.cif

e-68-0o947-sup1.cif^{(27KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008409/gk2461Isup2.hkl

e-68-0o947-Isup2.hkl^{(209KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812008409/gk2461Isup3.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
C17—H17⋯O2ⁱ	0.95	2.48	3.140 (2)	127

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

As a part of our ongoing study of 5-cyclohexyl-2-methyl-1-benzofuran derivatives containing 3-(4-fluorophenylsulfinyl (Choi et al., 2011) or 3-(4-bromophenylsulfinyl) (Choi et al., 2012) substituents, 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 0.004 (1) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring is in the chair form. The dihedral angle between the 4-methylphenyl ring and the mean plane of the benzofurn fragment is 81.60 (5)°. The crystal packing is stabilized by weak intermolecular C–H···O hydrogen bonds (Fig. 2 & Table 1). The crystal packing (Fig. 2) also exhibits weak slipped π–π interactions between the furan rings of adjacent molecules, with a Cg···Cgⁱⁱ distance of 3.545 (2) Å and an interplanar distance of3.489 (2) Å resulting in a slippage of 0.628 (2) Å (Cg is the centroid of the C1/C2/C7/O1/C8 furan ring).

Experimental

77% 3-Chloroperoxybenzoic acid (224 mg, 1.0 mmol) was added in small portions to a stirred solution of 5-cyclohexyl-2-methyl-3-(4-methylphenylsulfanyl)-1-benzofuran (302 mg, 0.9 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 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 77%, m.p. 423-424 K; R_f = 0.52 (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 ethyl acetate at room temperature.