5-Bromo-2-(4-chloro­phen­yl)-3-ethyl­sulfinyl-7-methyl-1-benzofuran

Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee

doi:10.1107/S1600536810042790

. 2010 Oct 30;66(Pt 11):o2960. doi: 10.1107/S1600536810042790

5-Bromo-2-(4-chlorophenyl)-3-ethylsulfinyl-7-methyl-1-benzofuran

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

PMCID: PMC3009263 PMID: 21589128

Abstract

In the title compound, C₁₇H₁₄BrClO₂S, the 4-chlorophenyl ring makes a dihedral angle of 13.42 (4)° with the mean plane of the benzofuran ring. In the crystal, pairs of intermolecular Br⋯O contacts [3.125 (1) Å] link the molecules into centrosymmetric dimers, which are further linked via intermolecular C—H⋯O hydrogen bonds.

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For our previous structural studies of related 3-ethylsulfinyl-5-halo-2-(4-halophenyl)-7-methyl-1-benzofuran derivatives, see: Choi et al. (2010a ▶,b ▶,c ▶,d ▶). For a review of halogen bonding, see: Politzer et al. (2007 ▶).

Experimental

Crystal data

C₁₇H₁₄BrClO₂S
M _r = 397.70
Triclinic,
a = 7.3159 (1) Å
b = 10.3502 (2) Å
c = 11.8936 (2) Å
α = 68.690 (1)°
β = 89.223 (1)°
γ = 70.941 (1)°
V = 787.36 (2) Å³
Z = 2
Mo Kα radiation
μ = 2.92 mm⁻¹
T = 179 K
0.29 × 0.28 × 0.25 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.485, T _max = 0.524
14107 measured reflections
3657 independent reflections
3342 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.025
wR(F ²) = 0.066
S = 1.08
3657 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.44 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/S1600536810042790/rz2506sup1.cif

e-66-o2960-sup1.cif^{(19.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042790/rz2506Isup2.hkl

e-66-o2960-Isup2.hkl^{(179.3KB, hkl)}

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—H17B⋯O2ⁱ	0.98	2.62	3.488 (2)	148

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by Blue-Bio Industry RIC at Dongeui University as an RIC programme under the Ministry of Knowledge Economy and Busan city.

supplementary crystallographic information

Comment

Many compounds involving a benzofuran ring have received particular attention in view of their potent pharmacological properties such as antifungal, antitumor and antiviral, antimicrobial activities (Aslam et al., 2006, Galal et al., 2009, Khan et al., 2005). These compounds widely occur in nature (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our continuing studies of the substituent effect on the solid state structures of 3-ethylsulfinyl-5-halo-2-(4-halophenyl)-7-methyl-1-benzofuran analogues (Choi et al., 2010a,b,c,d), we report herein on the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.019 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the mean plane of the benzofuran ring and the 4-chlorophenyl ring is 13.42 (4)° . The molecular packing (Fig. 2) is stabilized by a Br···O halogen-bonding between the bromine and the oxygen of the S═O unit [Br···O2ⁱⁱ = 3.125 (1) Å, C4—Br···O2ⁱⁱ = 167.44 (6)° .] (Politzer et al., 2007). The crystal packing (Fig. 2) is further stabilized by a weak intermolecular C—H···O hydrogen bond between the methyl H atom of the ethyl group and the S═O unit (C17—H17B···O2ⁱ; Table 1).

Experimental

77% 3-chloroperoxybenzoic acid (179 mg, 0.8 mmol) was added in small portions to a stirred solution of 5-bromo-2-(4-chlorophenyl)-3-ethylsulfanyl-7-methyl-1-benzofuran (318 mg, 0.8 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 3h, 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 79%, m.p. 443–444 K, R_f = 0.63 (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 tetrahydrofuran at room temperature.