3-(2-Fluoro­phenyl­sulfin­yl)-2,4,5,6-tetra­methyl-1-benzofuran

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S1600536812035714

. 2012 Aug 23;68(Pt 9):o2742. doi: 10.1107/S1600536812035714

3-(2-Fluorophenylsulfinyl)-2,4,5,6-tetramethyl-1-benzofuran

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

PMCID: PMC3435754 PMID: 22969625

Abstract

In the title compound, C₁₈H₁₇FO₂S, the 2-fluorophenyl ring makes a dihedral angle of 85.45 (4)° with the mean plane [r.m.s. deviation = 0.017 (1) Å] of the benzofuran fragment. In the crystal, molecules are linked by weak C—H⋯O and C—H⋯π interactions.

Related literature

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

Experimental

Crystal data

C₁₈H₁₇FO₂S
M _r = 316.38
Monoclinic,
a = 14.6851 (4) Å
b = 6.0786 (2) Å
c = 17.1647 (4) Å
β = 102.223 (1)°
V = 1497.47 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 173 K
0.33 × 0.30 × 0.07 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.593, T _max = 0.746
24418 measured reflections
3264 independent reflections
2803 reflections with I > 2σ(I)
R _int = 0.043

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.101
S = 1.08
3264 reflections
203 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.40 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 datablock(s) global, I. DOI: 10.1107/S1600536812035714/lr2079sup1.cif

e-68-o2742-sup1.cif^{(25.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035714/lr2079Isup2.hkl

e-68-o2742-Isup2.hkl^{(160.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812035714/lr2079Isup3.cml

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

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

Cg1 and Cg2 are the centroids of the C2–C7 benzene ring and the C13–C18 2-fluorophenyl ring, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2ⁱ	0.95	2.40	3.3279 (19)	165
C12—H12C⋯Cg1ⁱⁱ	0.98	2.69	3.486 (2)	138
C16—H16⋯Cg2ⁱⁱⁱ	0.95	2.70	3.553 (2)	149

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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 study of 2,4,5,6-tetramethyl-1-benzofuran derivatives containing 3-phenylsulfinyl (Seo et al., 2011a) and 3-(3-fluorophenylsulfinyl) (Seo et al., 2011b) 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 0.017 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 2-fluorophenyl ring and the mean plane of the benzofuran ring is 85.45 (4)°. In the crystal structure (Fig. 2), molecules are connected by weak C–H···O and C—H···π interactions (Table 1, Cg1 and Cg2 are the centroids -of the C2–C7 benzene ring and the C13–C18 2-fluorophenyl ring, respectively).

Experimental

3-Chloroperoxybenzoic acid (77%, 269 mg, 1.2 mmol) was added in small portions to a stirred solution of 3-(2-fluorophenylsulfanyl)-2,4,5,6-tetramethyl-1-benzofuran (330 mg, 1.1 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 3h, 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 63%, m.p. 464–465 K; R_f = 0.63 (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 ethyl acetate at room temperature.