5-Bromo-3-(4-fluoro­phenyl­sulfon­yl)-2,7-dimethyl-1-benzofuran

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S1600536812043607

. 2012 Oct 27;68(Pt 11):o3208. doi: 10.1107/S1600536812043607

5-Bromo-3-(4-fluorophenylsulfonyl)-2,7-dimethyl-1-benzofuran

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

PMCID: PMC3515296 PMID: 23284516

Abstract

In the title compound, C₁₆H₁₂BrFO₃S, the 4-fluorophenyl ring makes a dihedral angle of 72.35 (5)° with the mean plane [r.m.s. deviation = 0.008 (1) Å] of the benzofuran fragment. In the crystal, molecules are linked into [010] chains via two different inversion-generated pairs of C—H⋯O hydrogen bonds. The crystal structure also exhibits slipped π–π interactions between the benzene rings of neighbouring molecules [centroid–centroid distance = 3.667 (2) Å and slippage = 1.341 (2) Å], and between the benzene and the furan rings of neighbouring molecules [centroid–centroid distance = 3.759 (2) Å and slippage = 0.757 (2) Å].

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010 ▶, 2012 ▶).

Experimental

Crystal data

C₁₆H₁₂BrFO₃S
M _r = 383.23
Triclinic,
a = 8.0789 (1) Å
b = 9.2754 (2) Å
c = 11.3555 (2) Å
α = 71.283 (1)°
β = 72.645 (1)°
γ = 70.042 (1)°
V = 740.30 (2) Å³
Z = 2
Mo Kα radiation
μ = 2.94 mm⁻¹
T = 173 K
0.29 × 0.21 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.527, T _max = 0.746
14090 measured reflections
3680 independent reflections
3259 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.028
wR(F ²) = 0.074
S = 1.02
3680 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.47 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.^{(24.7KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812043607/hb6977sup1.cif

e-68-o3208-sup1.cif^{(24.7KB, cif)}

Click here for additional data file.^{(180.4KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812043607/hb6977Isup2.hkl

e-68-o3208-Isup2.hkl^{(180.4KB, hkl)}

Click here for additional data file.^{(5.5KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812043607/hb6977Isup3.cml

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
C3—H3⋯O2ⁱ	0.95	2.53	3.408 (2)	154
C9—H9A⋯O2ⁱⁱ	0.98	2.50	3.304 (2)	139

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

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 continuing study of 5-bromo-2-methyl-1-benzofuran derivatives containing 4-fluorophenylsulfonyl (Choi et al., 2010) and 4-methylphenylsulfonyl (Choi et al., 2012) substituents in 3-position, 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 0.008 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 4-fluorophenyl ring and the mean plane of the benzofuran ring is 72.35 (5). In the crystal structure (Fig. 2), molecules are linked via pairs of C—H···O hydrogen bonds (Table 1), forming inversion dimers. The crystal packing (Fig. 2) also exhibits slipped π–π interactions; the first one between the benzene rings of neighbouring molecules, with a Cg1···Cg1ⁱⁱⁱ distance of 3.667 (2) Å and an interplanar distance of 3.413 (2) Å resulting in a slippage of 1.341 (2) Å (Cg1 is the centroid of the C2–C7 benzene ring), and the second one between the benzene and the furan rings of neighbouring molecules, with a Cg1···Cg2ⁱⁱ distance of 3.759 (2) Å and an interplanar distance of 3.682 (2) Å resulting in a slippage of 0.757 (2) Å (Cg2 is the C1/C2/C7/O1/C8 furan ring).

Experimental

3-Chloroperoxybenzoic acid (77%, 381 mg, 1.7 mmol) was added in small portions to a stirred solution of 5-bromo-3-(4-fluorophenylsulfanyl)-2,7-dimethyl-1-benzofuran (281 mg, 0.8 mmol) in dichloromethane (40 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 (hexane–ethyl acetate, 4:1 v/v) to afford the title compound as a colorless solid [yield 71%, m.p. 472–473 K; R_f = 0.57 (hexane–ethyl acetate, 4:1 v/v)]. Colourless blocks were prepared by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.