2-(2-Fluoro­phen­yl)-3-methyl­sulfanyl-5-phenyl-1-benzo­furan

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S1600536813009768

. 2013 Apr 13;69(Pt 5):o721. doi: 10.1107/S1600536813009768

2-(2-Fluorophenyl)-3-methylsulfanyl-5-phenyl-1-benzofuran

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

PMCID: PMC3648253 PMID: 23723873

Abstract

In the title compound, C₂₁H₁₅FOS, the dihedral angles between the mean plane [r.m.s. deviation = 0.041 (1) Å] of the benzofuran fragment and the pendant 2-fluorophenyl and phenyl rings are 46.09 (3) and 24.34 (5)°, respectively. In the crystal, molecules are linked by weak C—H⋯π interactions, forming a three-dimensional network.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2006 ▶); Seo et al. (2011 ▶). graphic file with name e-69-0o721-scheme1.jpg

Experimental

Crystal data

C₂₁H₁₅FOS
M _r = 334.39
Monoclinic,
a = 11.1257 (2) Å
b = 7.4232 (1) Å
c = 19.4212 (3) Å
β = 97.319 (1)°
V = 1590.90 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 173 K
0.27 × 0.19 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.689, T _max = 0.746
28795 measured reflections
3967 independent reflections
3190 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.101
S = 1.05
3967 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.26 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 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Click here for additional data file.^{(26.1KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813009768/ds2230sup1.cif

e-69-0o721-sup1.cif^{(26.1KB, cif)}

Click here for additional data file.^{(194.5KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009768/ds2230Isup2.hkl

e-69-0o721-Isup2.hkl^{(194.5KB, hkl)}

Click here for additional data file.^{(6.2KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813009768/ds2230Isup3.cml

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

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

Cg1 and Cg2 are the C9–C14 phenyl and 2-fluorophenyl rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯Cg1ⁱ	0.95	2.82	3.682 (2)	131
C14—H14⋯Cg2ⁱⁱ	0.95	2.71	3.528 (2)	145

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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 3-methylsulfanyl-5-phenyl-1-benzofuran derivatives containing phenyl (Choi et al., 2006) and 3-fluorophenyl (Seo et al., 2011) substituents in 2-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 0.041 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angles between the mean plane of the benzofuran fragment and the pendant 2-fluorophenyl and phenyl rings are 46.09 (3) and 24.34 (5), respectively. In the crystal structure (Fig. 2), molecules are connected by weak intermolecular C–H···π interactions (Table 1, Cg1 and Cg2 are the centroids of the C9–C14 phenyl ring and the C15-C20 2-fluorophenyl ring, respectively).

Experimental

Zinc chloride (218 mg, 1.6 mmol) was added to a stirred solution of 4-phenylphenol (272 mg, 1.6 mmol) and 2-chloro-2-methylsulfanyl-2'-fluoroacetophenone (350 mg, 1.6 mmol) in dichloromethene (20 mL) at room temperature, and stirring was continued at the same temperature for 40 min. The reaction was quenched by the addition of water and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane-benzene, 5:2 v/v) to afford the title compound as a colorless solid [yield 51%, m.p. 368-369 K; R_f = 0.63 (hexane-benzene, 5:2 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.