3-(4-Bromo­phenyl­sulfon­yl)-5-cyclo­pentyl-2-methyl-1-benzofuran

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S1600536812019411

. 2012 May 5;68(Pt 6):o1624. doi: 10.1107/S1600536812019411

3-(4-Bromophenylsulfonyl)-5-cyclopentyl-2-methyl-1-benzofuran

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

PMCID: PMC3379229 PMID: 22719427

Abstract

In the title compound, C₂₀H₁₉BrO₃S, the cyclopentyl ring adopts an envelope conformation. The 4-bromophenyl ring makes a dihedral angle of 82.09 (6)° with the mean plane [mean deviation = 0.026 (2) Å] of the benzofuran fragment. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds and Br⋯O contacts [3.309 (2) Å].

Related literature

For background information and the crystal structure of a related compound, see: Seo et al. (2011 ▶). For a review of halogen bonding, see: Politzer et al. (2007 ▶). graphic file with name e-68-o1624-scheme1.jpg

Experimental

Crystal data

C₂₀H₁₉BrO₃S
M _r = 419.32
Monoclinic,
a = 6.8956 (2) Å
b = 17.1034 (3) Å
c = 15.7773 (3) Å
β = 97.533 (1)°
V = 1844.69 (7) Å³
Z = 4
Mo Kα radiation
μ = 2.36 mm⁻¹
T = 173 K
0.38 × 0.34 × 0.27 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.469, T _max = 0.570
18310 measured reflections
4602 independent reflections
3416 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.093
S = 1.02
4602 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.73 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/S1600536812019411/fy2055sup1.cif

e-68-o1624-sup1.cif^{(27.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019411/fy2055Isup2.hkl

e-68-o1624-Isup2.hkl^{(225.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812019411/fy2055Isup3.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	2.51	3.169 (3)	126

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

As a part of our ongoing study of 5-cyclopentyl-2-methyl-1-benzofuran derivatives containing a 3-phenylsulfonyl substituent (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 0.026 (2) Å from the least-squares plane defined by the nine constituent atoms. The cyclopentyl ring has an envelope conformtion. The dihedral angle between the 4-bromophenyl ring and the mean plane of the benzofurn fragment is 82.09 (6)°. In the crystal structure (Fig. 2), molecules are connected by weak C—H···O interactions (Table 1). The crystal packing (Fig. 2) also exhibits Br···O halogen-bonding interactions between the bromine atom and the O atom of the O═S═O unit [Br1···O3ⁱ = 3.309 (2) Å, C18—Br1···O3ⁱ = 153.82 (8)°] (Politzer et al., 2007).

Experimental

3-Chloroperoxybenzoic acid (77%, 381 mg, 1.7 mmol) was added in small portions to a stirred solution of 3-(4-bromophenylsulfanyl)-5-cyclopentyl-2-methyl-1-benzofuran (310 mg, 0.8 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 10 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 (benzene) to afford the title compound as a colorless solid [yield 71%, m.p. 423–424 K; R_f = 0.48 (benzene)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in acetone at room temperature.