5-Cyclo­pentyl-2-(4-methyl­phen­yl)-3-methyl­sulfinyl-1-benzofuran

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S1600536812042249

. 2012 Oct 13;68(Pt 11):o3124. doi: 10.1107/S1600536812042249

5-Cyclopentyl-2-(4-methylphenyl)-3-methylsulfinyl-1-benzofuran

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

PMCID: PMC3515229 PMID: 23284449

Abstract

In the title compound, C₂₁H₂₂O₂S, the cyclopentyl ring adopts an envelope conformation with the flap atom connected to the benzofuran residue. The benzofuran unit is essentially planar, with a mean deviation from the least-squares plane defined by the nine constituent ring atoms of 0.008 (2) Å. In the crystal, molecules are linked via pairs of C—H⋯π interactions, forming inversion dimers. In the ring of the 4-methylphenyl group, four C atoms and their attached H atoms are disordered over two sets of sites, with site-ccupancy factors of 0.899 (5) and 0.10.

Related literature

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

Experimental

Crystal data

C₂₁H₂₂O₂S
M _r = 338.45
Monoclinic,
a = 15.2869 (5) Å
b = 7.2881 (3) Å
c = 15.3608 (6) Å
β = 97.599 (2)°
V = 1696.35 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 173 K
0.29 × 0.23 × 0.17 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.653, T _max = 0.746
12919 measured reflections
2994 independent reflections
2154 reflections with I > 2σ(I)
R _int = 0.043

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.173
S = 1.07
2994 reflections
212 parameters
14 restraints
H-atom parameters constrained
Δρ_max = 0.86 e Å⁻³
Δρ_min = −0.36 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, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Click here for additional data file.^{(30.4KB, cif)}

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536812042249/hg5259sup1.cif

e-68-o3124-sup1.cif^{(30.4KB, cif)}

Click here for additional data file.^{(146.9KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042249/hg5259Isup2.hkl

e-68-o3124-Isup2.hkl^{(146.9KB, hkl)}

Click here for additional data file.^{(6.8KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812042249/hg5259Isup3.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
C20—H20B⋯Cg ⁱ	0.98	2.78	3.665 (2)	150

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the Blue-Bio Industry Regional Innovation Center (RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan city.

supplementary crystallographic information

Comment

As a part of our ongoing study of 5-cyclopentyl-3-methylsulfinyl-1-benzofuran derivatives containing 2-phenyl (Choi et al., 2011) and 2-(4-fluorophenyl) (Seo et al.,2011) 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 0.008 (2) Å from the least-squares plane defined by the nine constituent atoms. The cyclopentyl ring has an envelope conformation. In the phenyl ring of the 4-methylphenyl group, the four C atoms (C15/C16/C18/C19) are disordered over two positions with site-ccupancy factors, from refinement of of 0.899 (5) (part A) and 0.101 (5) (part B). In the crystal structure, molecules are connected via pairs of weak C—H···π interactions (Fig. 2 & Table 1, Cg is the centroid of the C2–C7 benzene ring), forming inversion dimers.

Experimental

3-Chloroperoxybenzoic acid (77%, 224 mg, 1.0 mmol) was added in small portions to a stirred solution of 5-cyclopentyl-2-(4-methylphenyl)-3-methylsulfanyl-1-benzofuran (290 mg, 0.9 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 5h, 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, 1:1 v/v) to afford the title compound as a colorless solid [yield 71%, m.p. 424–425 K; Rf = 0.65 (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 acetone at room temperature.