5-Bromo-3-(4-fluoro­phenyl­sulfin­yl)-2-phenyl-1-benzofuran

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S1600536812044054

. 2012 Oct 31;68(Pt 11):o3242. doi: 10.1107/S1600536812044054

5-Bromo-3-(4-fluorophenylsulfinyl)-2-phenyl-1-benzofuran

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

PMCID: PMC3515320 PMID: 23284540

Abstract

In the title compound, C₂₀H₁₂BrFO₂S, the dihedral angles between the mean plane [r.m.s. deviation = 0.006 (2) Å] of the benzofuran fragment and the pendant 4-fluorophenyl and phenyl rings are 84.98 (5) and 40.98 (6)°, respectively. In the crystal, molecules are linked by C—H⋯O and C—H⋯π interactions.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2009 ▶); Seo et al. (2011 ▶).

Experimental

Crystal data

C₂₀H₁₂BrFO₂S
M _r = 415.27
Triclinic,
a = 9.2288 (2) Å
b = 9.4790 (2) Å
c = 10.4939 (2) Å
α = 67.396 (1)°
β = 89.933 (1)°
γ = 82.373 (1)°
V = 838.74 (3) Å³
Z = 2
Mo Kα radiation
μ = 2.60 mm⁻¹
T = 173 K
0.39 × 0.33 × 0.22 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.557, T _max = 0.746
15136 measured reflections
3888 independent reflections
3417 reflections with I > 2σ(I)
R _int = 0.045

Refinement

R[F ² > 2σ(F ²)] = 0.030
wR(F ²) = 0.079
S = 1.05
3888 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.74 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

Click here for additional data file.^{(25.9KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812044054/bv2213sup1.cif

e-68-o3242-sup1.cif^{(25.9KB, cif)}

Click here for additional data file.^{(190.6KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812044054/bv2213Isup2.hkl

e-68-o3242-Isup2.hkl^{(190.6KB, hkl)}

Click here for additional data file.^{(5.9KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812044054/bv2213Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg is the centroid of the C9–C14 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O2ⁱ	0.95	2.41	3.341 (3)	167
C19—H19⋯O1ⁱⁱ	0.95	2.50	3.447 (2)	175
C16—H16⋯Cg ⁱⁱⁱ	0.95	2.99	3.832 (2)	148

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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

As a part of our ongoing studies of 5-bromo-1-benzofuran derivatives containing 2-phenyl-3-phenylsulfinyl (Choi et al., 2009) and 2-(4-fluorophenyl)-3-phenylsulfinyl (Seo 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 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angles formed by the mean plane of the benzofuran fragment and the pendant 4-fluorophenyl and phenyl rings are 84.98 (5) and 40.98 (6)°, respectively. 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 C9–C14 2-phenyl ring).

Experimental

3-Chloroperoxybenzoic acid (77%, 202 mg, 0.9 mmol) was added in small portions to a stirred solution of 5-bromo-3-(4-fluorophenylsulfanyl)-2-phenyl-1-benzofuran (319 mg, 0.8 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 5h, 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 63%, m.p. 445-446 K; R_f = 0.75 (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 acetone at room temperature.