5-Cyclo­hexyl-3-(3-fluoro­phenyl­sulfin­yl)-2-methyl-1-benzo­furan

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S160053681301475X

. 2013 Jun 8;69(Pt 7):o1026. doi: 10.1107/S160053681301475X

5-Cyclohexyl-3-(3-fluorophenylsulfinyl)-2-methyl-1-benzofuran

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

PMCID: PMC3772463 PMID: 24046606

Abstract

In the title compound, C₂₁H₂₁FO₂S, the cyclohexyl ring adopts a chair conformation. The 3-fluorophenyl ring makes a dihedral angle of 83.16 (4)° with the mean plane [r.m.s. deviation = 0.005 (1) Å] of the benzofuran ring system. In the crystal, molecules are linked by pairs of C—H⋯π interactions into inversion dimers, which are further packed into stacks along the a-axis direction by C—H⋯π interactions.

Related literature

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

Experimental

Crystal data

C₂₁H₂₁FO₂S
M _r = 356.44
Triclinic,
a = 8.9147 (1) Å
b = 10.1270 (2) Å
c = 10.5101 (2) Å
α = 90.376 (1)°
β = 110.407 (1)°
γ = 97.439 (1)°
V = 880.44 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 173 K
0.33 × 0.31 × 0.29 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.692, T _max = 0.746
19435 measured reflections
4369 independent reflections
3897 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.124
S = 1.04
4369 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.94 e Å⁻³
Δρ_min = −0.41 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 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681301475X/bx2442sup1.cif

e-69-o1026-sup1.cif^{(28KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681301475X/bx2442Isup2.hkl

e-69-o1026-Isup2.hkl^{(214KB, hkl)}

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

Supplementary material file. DOI: 10.1107/S160053681301475X/bx2442Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯Cg1ⁱ	0.99	3.00	3.697 (1)	128
C14—H14B⋯Cg2ⁱ	0.99	2.91	3.569 (1)	125
C19—H19⋯Cg2ⁱⁱ	0.95	2.90	3.677 (1)	140

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

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 continuing study of 5-cyclohexyl-2-methyl-1-benzofuran derivatives containing phenylsulfinyl (Choi et al., 2011), 4-bromophenylsulfinyl (Choi et al., 2012a) and 4-methylphenylsulfinyl (Choi et al., 2012b)substituents in 3-position, 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 0.005 (1) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring has the chair form. The dihedral angle between the 3-fluorophenyl ring and the mean plane of the benzofuran ring system is 83.16 (4)°. In the crystal structure (Fig. 2), molecules are connected by pairs of C—H···π interactions into dimers, which are further packed into stacks along the a axis by C—H···π interactions (Table 1, Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively).

Experimental

3-Chloroperoxybenzoic acid (77%, 202 mg, 0.9 mmol) was added in small portions to a stirred solution of 5-cyclohexyl-3-(3-fluorophenylsulfanyl)-2-methyl-1-benzofuran (272 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, 4:1 v/v) to afford the title compound as a colorless solid [yield 68%, m.p. 403–404 K; R_f = 0.43 (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 ethyl acetate at room temperature.