3-(3-Chloro­phenyl­sulfon­yl)-5-isopropyl-2-methyl-1-benzofuran

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S1600536812008525

. 2012 Mar 3;68(Pt 4):o942. doi: 10.1107/S1600536812008525

3-(3-Chlorophenylsulfonyl)-5-isopropyl-2-methyl-1-benzofuran

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

PMCID: PMC3343923 PMID: 22590004

Abstract

In the title compound, C₁₈H₁₇ClO₃S, the 3-chlorobenzene ring makes a dihedral angle of 82.04 (5)° with the mean plane [r.m.s. deviation = 0.006 (1) Å] of the benzofuran fragment. In the crystal, molecules are linked by weak C—H⋯O and C—H⋯π interactions.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C₁₈H₁₇ClO₃S
M _r = 348.83
Triclinic,
a = 7.1700 (2) Å
b = 9.9400 (2) Å
c = 12.2508 (3) Å
α = 83.484 (1)°
β = 77.907 (1)°
γ = 85.707 (1)°
V = 847.05 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 173 K
0.29 × 0.24 × 0.13 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.903, T _max = 0.955
16044 measured reflections
4231 independent reflections
3596 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.132
S = 1.06
4231 reflections
211 parameters
H-atom parameters constrained
Δρ_max = 0.85 e Å⁻³
Δρ_min = −0.46 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/S1600536812008525/lr2052sup1.cif

e-68-0o942-sup1.cif^{(25.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008525/lr2052Isup2.hkl

e-68-0o942-Isup2.hkl^{(207.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812008525/lr2052Isup3.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
C5—H5⋯O3ⁱ	0.95	2.42	3.321 (2)	159
C12—H12A⋯O2ⁱⁱ	0.98	2.42	3.375 (2)	165
C16—H16⋯Cgⁱⁱⁱ	0.95	2.71	3.646 (2)	170

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

supplementary crystallographic information

Comment

As a part of our ongoing study of 5-isopropyl-2-methyl-1-benzofuran derivatives containing either 3-(4-fluorophenylsulfonyl) (Choi et al., 2010) or 3-(4-chlorophenylsufonyl) (Choi 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 0.006 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 3-chlorobenzene ring and the mean plane of the benzofuran fragment is 82.04 (5)°. The crystal packing is stabilized by weak intermolecular C—H···O hydrogen bonds (Fig. 2 & Table 1). The crystal packing is further stabilized by intermolecular C—H···π interactions (Fig. 2 & Table 1, Cg is the centroid of the C2–C7 benzene ring).

Experimental

77% 3-Chloroperoxybenzoic acid (381 mg, 1.7 mmol) was added in small portions to a stirred solution of 3-(3-chlorophenylsulfanyl)-5-isopropyl-2-methyl-1-benzofuran (279 mg, 0.8 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 8h, 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 70%, m.p. 357–358 K; R_f = 0.51 (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 diisopropyl ether at room temperature.