5-Bromo-3-(4-fluoro­phenyl­sulfin­yl)-2,4,6-trimethyl-1-benzofuran

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

doi:10.1107/S1600536811002303

. 2011 Jan 22;67(Pt 2):o471. doi: 10.1107/S1600536811002303

5-Bromo-3-(4-fluorophenylsulfinyl)-2,4,6-trimethyl-1-benzofuran

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

PMCID: PMC3051696 PMID: 21523130

Abstract

In the title molecule, C₁₇H₁₄BrFO₂S, the 4-fluorophenyl ring makes a dihedral angle of 75.92 (5)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds and aromatic π–π interactions between the benzene and the furan rings of neighbouring molecules [centroid–centroid distance = 3.556 (1) Å].

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 5-bromo-3-(4-fluorophenylsulfinyl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C₁₇H₁₄BrFO₂S
M _r = 381.25
Triclinic,
a = 7.6121 (3) Å
b = 8.3551 (3) Å
c = 13.0681 (4) Å
α = 71.551 (2)°
β = 84.206 (2)°
γ = 74.850 (2)°
V = 760.86 (5) Å³
Z = 2
Mo Kα radiation
μ = 2.85 mm⁻¹
T = 173 K
0.29 × 0.28 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.621, T _max = 0.746
13138 measured reflections
3491 independent reflections
3041 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.026
wR(F ²) = 0.070
S = 1.03
3491 reflections
202 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.36 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/S1600536811002303/su2248sup1.cif

e-67-0o471-sup1.cif^{(19.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002303/su2248Isup2.hkl

e-67-0o471-Isup2.hkl^{(171.2KB, 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
C14—H14⋯O2ⁱ	0.95	2.35	3.232 (2)	154

Open in a new tab

Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Many compounds containing a benzofuran ring show interesting potent pharmacological properties, such as antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2006; Galal et al., 2009; Khan et al., 2005). These compounds occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing study of the substituent effect on the solid state structures of 5-bromo-3-(4-fluorophenylsulfinyl)-2-methyl-1-benzofuran analogues (Choi et al., 2010; 2011), 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 0.004 (1)Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the mean plane of the benzofuran fragment and the 4-fluorophenyl ring is 75.92 (5)°.

In the crystal the molecular packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds between the 4-fluorophenyl H-atom and the oxygen of the S═O unit (Table 1; C14–H14···O2ⁱ). The crystal packing (Fig. 2) is further stabilized by aromatic π–π interactions between the benzene and furan rings of the adjacent molecules. The Cg1···Cg2ⁱⁱ distance of 3.556 (1)Å (Cg1 and Cg2 are the centroids of the C2-C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively; symmetry code: (ii) = - x + 2, - y + 1, - z + 1).

Experimental

77% 3-chloroperoxybenzoic acid (224 mg, 1.0 mmol) was added in small portions to a stirred solution of 5-bromo-3-(4-fluorophenylsulfanyl)-2,4,6-trimethyl-1-benzofuran (329 mg, 0.9 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 4h, 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 73%, m.p. 424–425 K; R_f = 0.54 (hexane–ethyl acetate, 4:1 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.