3-(3-Bromo­phenyl­sulfin­yl)-5-cyclo­hexyl-2-methyl-1-benzo­furan

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S160053681400316X

. 2014 Feb 15;70(Pt 3):o309. doi: 10.1107/S160053681400316X

3-(3-Bromophenylsulfinyl)-5-cyclohexyl-2-methyl-1-benzofuran

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

PMCID: PMC3998404 PMID: 24765010

Abstract

In the title compound, C₂₁H₂₁BrO₂S, the cyclohexyl ring adopts a chair conformation. The dihedral angle between the mean plane [r.m.s. deviation = 0.178 (2) Å] of the benzofuran ring system and the mean plane of the 3-bromophenyl ring is 86.52 (6)°. In the crystal, molecules are linked by weak C—H⋯O and C—H⋯π hydrogen bonds, and by a slipped π–π interaction between the furan rings of neighbouring molecules [centroid–centroid distance = 3.518 (3) Å, interplanar distance = 3.471 (3) Å and slippage = 0.573 (3) Å], resulting in a three-dimensional network.

Related literature

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

Experimental

Crystal data

C₂₁H₂₁BrO₂S
M _r = 417.35
Monoclinic,
a = 17.6432 (9) Å
b = 8.9425 (5) Å
c = 12.4776 (7) Å
β = 108.277 (3)°
V = 1869.33 (18) Å³
Z = 4
Mo Kα radiation
μ = 2.32 mm⁻¹
T = 173 K
0.33 × 0.25 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.482, T _max = 0.746
13952 measured reflections
3290 independent reflections
2635 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.081
S = 1.02
3290 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.35 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) I. DOI: 10.1107/S160053681400316X/gk2602sup1.cif

e-70-0o309-sup1.cif^{(26.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681400316X/gk2602Isup2.hkl

e-70-0o309-Isup2.hkl^{(161.4KB, hkl)}

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

Supporting information file. DOI: 10.1107/S160053681400316X/gk2602Isup3.cml

CCDC reference: 986408

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

Cg1 is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O1ⁱ	0.98	2.58	3.358 (3)	136
C21—H21⋯O2ⁱⁱ	0.95	2.45	3.306 (3)	151
C15—H15C⋯Cg1ⁱⁱⁱ	0.98	2.82	3.502 (3)	127

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

supplementary crystallographic information

1. Comment

As a part of our continuing study of 5-cyclohexyl-2-methyl-1-benzofuran derivatives containing 4-fluorophenylsulfinyl (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 cyclohexyl ring has a chair conformation. The benzofuran ring system is essentially planar, with a mean deviation of 0.178 (2) Å from the least-squares plane defined by the nine constituent atoms. The 3-bromophenyl ring is essentially planar, with a mean deviation of 0.005 (2) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring system and the 3-bromophenyl ring is 86.52 (6)°. In the crystal structure (Fig. 2), molecules are connected by C—H···O and C—H···π hydrogen bonds (Table 1, Cg1 is the centroid of the C2–C7 benzene ring). The crystal packing (Fig. 2) also exhibits a slipped π···π interaction between the furan rings of neighbouring molecules, with a Cg2···Cg2ⁱⁱⁱ distance of 3.518 (3) Å and an interplanar distance of 3.471 (3) Å resulting in a slippage of 0.573 (3) Å (Cg2 is the centroid of the C1/C2/C7/O1/C8 furan ring).

2. Experimental

3-Chloroperoxybenzoic acid (77%, 224 mg, 1.0 mmol) was added in small portions to a stirred solution of 3-(3-bromophenylsulfanyl)-5-cyclohexyl-2-methyl-1-benzofuran(361 mg, 0.9 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 71%, m.p. 415–416 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 ethyl acetate at room temperature.