3-(4-Chloro­phenyl­sulfon­yl)-5-isopropyl-2-methyl-1-benzofuran

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S1600536811014784

. 2011 Apr 29;67(Pt 5):o1226. doi: 10.1107/S1600536811014784

3-(4-Chlorophenylsulfonyl)-5-isopropyl-2-methyl-1-benzofuran

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

PMCID: PMC3089266 PMID: 21754524

Abstract

In the title molecule, C₁₈H₁₇ClO₃S, the 4-chlorophenyl ring makes a dihedral angle of 77.03 (5)° with the mean plane of the benzofuran fragment. In the crystal structure, the molecules are linked by weak intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For the structures of related 3-arylsulfonyl-5-isopropyl-2-methyl-1-benzofuran derivatives, see: Choi et al. (2008 ▶, 2010 ▶).

Experimental

Crystal data

C₁₈H₁₇ClO₃S
M _r = 348.83
Monoclinic,
a = 11.4851 (4) Å
b = 11.3194 (4) Å
c = 13.0600 (4) Å
β = 101.475 (2)°
V = 1663.92 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 296 K
0.29 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.660, T _max = 0.746
14572 measured reflections
3643 independent reflections
3109 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.120
S = 1.08
3643 reflections
211 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.65 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 datablocks global, I. DOI: 10.1107/S1600536811014784/su2271sup1.cif

e-67-o1226-sup1.cif^{(19.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014784/su2271Isup2.hkl

e-67-o1226-Isup2.hkl^{(178.6KB, hkl)}

Additional supplementary materials: 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
C12—H12C⋯O3ⁱ	0.96	2.57	3.489 (3)	160
C11—H11B⋯Cgⁱⁱ	0.96	2.81	3.562 (3)	136

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

Acknowledgments

This work was supported by a Dong-eui University Foundation Grant (2011).

supplementary crystallographic information

Comment

Many compounds containing a benzofuran ring have recently drawn considerable attention due to their interesting pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2009; Galal et al., 2009; Khan et al., 2005). These compounds occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing program of the substituent effect on the solid state structures of 3-arylsulfonyl-5-isopropyl-2-methyl-1-benzofuran analogues (Choi et al., 2008, 2010), 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 0.007 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the 4-chlorophenyl ring and the mean plane of the benzofuran fragment is 77.03 (5)°. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds between a methyl H atom and the O atom of the sulfonyl group (Table 1; C12—H12C···O3ⁱ). The crystal packing (Fig. 3) is further stabilized by intermolecular C—H···π interactions between a methyl H atom of the isopropyl group and the benzene ring of an adjacent molecule (Table 1; C10—H11B···Cgⁱⁱ, Cg is the centroid of the C2–C7 benzene ring).

Experimental

77% 3-chloroperoxybenzoic acid (560 mg, 2.5 mmol) was added in small portions to a stirred solution of 3-(4-chlorophenylsulfanyl)-5-isopropyl-2-methyl-1-benzofuran (380 mg, 1.2 mmol) in dichloromethane (40 ml) at 273 K. After being stirred at room temperature for 6 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 colourless solid [yield 71%, m.p. 409–410 K; R_f = 0.65 (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.