3-(4-Bromo­phenyl­sulfin­yl)-2,5-dimethyl-1-benzofuran

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S1600536812002656

. 2012 Feb 4;68(Pt 3):o584. doi: 10.1107/S1600536812002656

3-(4-Bromophenylsulfinyl)-2,5-dimethyl-1-benzofuran

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

PMCID: PMC3297310 PMID: 22412500

Abstract

In the title compound, C₁₆H₁₃BrO₂S, the 4-bromophenyl ring makes a dihedral angle of 87.87 (6)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by a weak π–π interaction between the 4-bromophenyl rings [centroid-to-centroid distance = 3.907 (3) Å, interplanar distance = 3.528 (3) Å and slippage = 1.679 (3) Å].

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 crystal structures of related compounds, see: Choi et al. (2010a ▶,b ▶).

Experimental

Crystal data

C₁₆H₁₃BrO₂S
M _r = 349.23
Triclinic,
a = 6.4145 (3) Å
b = 10.0266 (5) Å
c = 11.7639 (6) Å
α = 101.606 (3)°
β = 92.240 (2)°
γ = 103.932 (2)°
V = 716.28 (6) Å³
Z = 2
Mo Kα radiation
μ = 3.01 mm⁻¹
T = 173 K
0.30 × 0.23 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.518, T _max = 0.746
12848 measured reflections
3507 independent reflections
3048 reflections with I > 2σ(I)
R _int = 0.044

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.087
S = 1.04
3507 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.59 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/S1600536812002656/kp2381sup1.cif

e-68-0o584-sup1.cif^{(17.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002656/kp2381Isup2.hkl

e-68-0o584-Isup2.hkl^{(172KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812002656/kp2381Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by the Blue-Bio Industry Regional Innovation Centre (grant No. RIC08-06-07) 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 drawn much attention owing to their valuable biological properties such as antibacterial, antifungal, antitumor, and antiviral activities (Aslam et al., 2009; Galal et al., 2009; Khan et al., 2005). These benzofuran derivatives occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our continuing study of 2,5-dimethyl-1-benzofuran derivatives containing either 3-(4-fluorophenylsulfinyl) (Choi et al., 2010a) or 3-(4-chlorophenylsufinyl) (Choi et al., 2010b) substituents, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is planar with the mean deviation of 0.006 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 4-bromophenyl ring and the mean plane of the benzofuran fragment is 87.87 (6)°. The crystal packing (Fig. 2) is further stabilised by a weak π–π interaction between the 4-bromophenyl rings of adjacent molecules, with a Cg···Cgⁱ distance of 3.907 (3) Å and an interplanar distance of 3.528 (3) Å resulting in a slippage of 1.679 (3) Å (Cg is the centroid of the C11–C16 4-bromophenyl ring).

Experimental

3-Chloroperoxybenzoic acid 77% (269 mg, 1.2 mmol) was added in small portions to a stirred solution of 3-(4-bromophenylsulfanyl)-2,5-dimethyl-1-benzofuran (366 mg, 1.1 mmol) in dichloromethane (40 ml) at 273 K. After being stirred at room temperature for 5 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 (hexane–ethyl acetate, 2:1 v/v) to afford the title compound as a colourless solid [yield 72%, m.p. 434–435 K; R_f = 0.49 (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.