5-Fluoro-2-(4-fluoro­phen­yl)-7-methyl-3-phenyl­sulfinyl-1-benzo­furan

Pil Ja Seo; Hong Dae Choi; Uk Lee

doi:10.1107/S1600536813017583

. 2013 Jun 29;69(Pt 7):o1187. doi: 10.1107/S1600536813017583

5-Fluoro-2-(4-fluorophenyl)-7-methyl-3-phenylsulfinyl-1-benzofuran

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

PMCID: PMC3770441 PMID: 24046726

Abstract

In the title compound, C₂₁H₁₄F₂O₂S, the dihedral angles between the mean plane [r.m.s. deviation = 0.007 (2) Å] of the benzofuran ring system and the pendant 4-fluorophenyl and phenyl rings are 5.93 (9) and 80.23 (5)°, respectively. In the crystal, molecules are linked by weak C—H⋯O and 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. (2011 ▶, 2012 ▶); Seo et al. (2011 ▶).

Experimental

Crystal data

C₂₁H₁₄F₂O₂S
M _r = 368.38
Monoclinic,
a = 12.3698 (8) Å
b = 7.9967 (5) Å
c = 17.4195 (10) Å
β = 100.323 (4)°
V = 1695.20 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 173 K
0.30 × 0.26 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.655, T _max = 0.746
30145 measured reflections
4267 independent reflections
3147 reflections with I > 2σ(I)
R _int = 0.065

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.123
S = 1.04
4267 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.29 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, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813017583/gg2118sup1.cif

e-69-o1187-sup1.cif^{(26.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813017583/gg2118Isup2.hkl

e-69-o1187-Isup2.hkl^{(209.1KB, hkl)}

Click here for additional data file.^{(6.4KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813017583/gg2118Isup3.cml

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

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

Cg1 is the centroid of the C16–C21 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯O2ⁱ	0.95	2.35	3.252 (3)	158
C9—H9B⋯Cg1ⁱⁱ	0.98	2.79	3.519 (2)	132

Open in a new tab

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

Acknowledgments

This work was supported by a Dong-eui University grant (No. 2013AA076).

supplementary crystallographic information

Comment

As a part of our continuing study of 2-(4-fluorophenyl)-3-phenylsulfinyl-1-benzofuran derivatives containing chloro (Choi et al., 2011), bromo (Seo et al., 2011) and iodo (Choi et al., 2012) substituents in 5-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 0.007 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angles between the mean plane of the benzofuran ring system and the pendant 4-fluorophenyl and phenyl rings are 5.93 (9) and 80.23 (5)°, respectively. In the crystal structure (Fig. 2), molecules are connected by weak C–H···O and C–H···π interactions (Table 1, Cg1 is the centroid of the C16-C21 phenyl ring), forming a three-dimensional network.

Experimental

3-Chloroperoxybenzoic acid (77%, 202 mg, 0.9 mmol) was added in small portions to a stirred solution of 5-fluoro-2-(4-fluorophenyl)-7-methyl-3-phenylsulfanyl-1-benzofuran (282 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 (benzene) to afford the title compound as a colorless solid [yield 54%, m.p. 466-467 K; R_f = 0.42 (benzene)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in benzene at room temperature.