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

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S1600536812048313

. 2012 Nov 30;68(Pt 12):o3487. doi: 10.1107/S1600536812048313

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

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

PMCID: PMC3589059 PMID: 23476295

Abstract

In the title compound, C₁₇H₁₅BrO₃S, the 4-bromophenyl ring makes a dihedral angle of 76.58 (9)° with the mean plane [r.m.s. deviation = 0.006 (2) Å] of the benzofuran fragment. In the crystal, molecules are linked by weak C—H⋯O and C—H⋯π interactions.

Related literature

For the biological activity of benzofuran compounds, see: Aslam et al. (2009 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For the crystal structures of related compounds, see: Choi et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C₁₇H₁₅BrO₃S
M _r = 379.26
Tetragonal,
a = 10.2785 (3) Å
c = 15.2899 (6) Å
V = 1615.34 (9) Å³
Z = 4
Mo Kα radiation
μ = 2.68 mm⁻¹
T = 173 K
0.31 × 0.17 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.450, T _max = 0.746
8518 measured reflections
3085 independent reflections
2558 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.067
S = 1.03
3085 reflections
201 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.29 e Å⁻³
Absolute structure: Flack (1983 ▶), 1000 Friedel pairs
Flack parameter: 0.001 (7)

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, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Click here for additional data file.^{(25.3KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812048313/rn2111sup1.cif

e-68-o3487-sup1.cif^{(25.3KB, cif)}

Click here for additional data file.^{(151.4KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812048313/rn2111Isup2.hkl

e-68-o3487-Isup2.hkl^{(151.4KB, hkl)}

Click here for additional data file.^{(5.7KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812048313/rn2111Isup3.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
C6—H6⋯O3ⁱ	0.95	2.53	3.238 (4)	131
C11—H11A⋯O3ⁱⁱ	0.98	2.58	3.321 (4)	132
C14—H14⋯Cg ⁱⁱⁱ	0.95	2.70	3.495 (4)	142

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

Acknowledgments

This work was supported by the Blue-Bio Industry Regional Innovation Center (RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan City.

supplementary crystallographic information

Comment

Many compounds containing the benzofuran skeleton have attracted much interest owing to their biological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2009; Galal et al., 2009; Khan et al., 2005). As a part of our ongoing study of 5-ethyl-2-methyl-1-benzofuran derivatives containing 4-fluorophenylsulfonyl (Choi et al., 2010) or 3-fluorophenylsulfonyl (Choi et al., 2011) substituents in the 3-position, we report herein the crystal structure of the title compound.

The title compound crystallizes as the non-centrosymmetric space group P4₃ in spite of having no asymmetric C atoms.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a 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 ring is 76.58 (9)°. In the crystal structure (Fig. 2), molecules are connected by weak C—H···O and C—H···π interactions (Table 1, Cg is the centroid of the C2–C7 benzene ring).

Experimental

3-Chloroperoxybenzoic acid (77%, 448 mg, 2.0 mmol) was added in small portions to a stirred solution of 3-(4-bromophenylsulfanyl)-5-ethyl-2-methyl-1-benzofuran (312 mg, 0.9 mmol) in dichloromethane (50 mL) at 273 K. After being stirred at room temperature for 10h, 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 68%, m.p. 404–405 K; R_f = 0.61 (benzene)]. 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.