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

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S1600536814014822

. 2014 Jun 25;70(Pt 7):o830. doi: 10.1107/S1600536814014822

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

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

PMCID: PMC4120585 PMID: 25161604

Abstract

In the title compound, C₁₈H₁₇FO₂S, the dihedral angle between the plane of the benzofuran ring system (r.m.s. deviation = 0.013 Å) and that of the 4-fluorophenyl ring is 74.30 (5)°. In the crystal, weak C—H⋯O and C—H⋯F hydrogen bonds link the molecules into columns extending in direction [100].

Keywords: crystal structure

Related literature

For the crystal structures of related compounds, see: Choi et al. (2012 ▶); Seo et al. (2011a ▶,b ▶). graphic file with name e-70-0o830-scheme1.jpg

Experimental

Crystal data

C₁₈H₁₇FO₂S
M _r = 316.38
Orthorhombic,
a = 7.8869 (2) Å
b = 11.0042 (2) Å
c = 17.5181 (4) Å
V = 1520.38 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 173 K
0.67 × 0.32 × 0.27 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.862, T _max = 0.941
13898 measured reflections
3761 independent reflections
3369 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.094
S = 1.05
3761 reflections
203 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983 ▶), 1812 Friedel pairs
Absolute structure parameter: −0.02 (7)

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

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814014822/cv5468sup1.cif

e-70-0o830-sup1.cif^{(25.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814014822/cv5468Isup2.hkl

e-70-0o830-Isup2.hkl^{(184.4KB, hkl)}

Click here for additional data file.^{(6.1KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814014822/cv5468Isup3.cml

CCDC reference: 1009827

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O2ⁱ	0.95	2.31	3.247 (3)	169
C17—H17⋯F1ⁱⁱ	0.95	2.50	3.083 (2)	120

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

supplementary crystallographic information

S1. Comment

As a part of our ongoing project of 2,4,5,6-tetramethyl-1-benzofuran derivatives containing phenylsulfinyl (Seo et al., 2011a), 3-fluorophenylsulfinyl (Seo et al., 2011b) and 2-fluorophenylsulfinyl (Choi et al., 2012) substituents in 3-position, 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 0.013 (2) Å from the least-squares plane defined by the nine constituent atoms. The 4-fluorophenyl ring is essentially planar, with a mean deviation of 0.002 (1) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring system and the 4-fluorophenyl ring is 74.30 (5)°. In the crystal structure (Fig. 2), weak intermolecular C—H···O and C—H···F hydrogen bonds (Table 1) link the molecules into columns extended in [100].

S2. Experimental

3-Chloroperoxybenzoic acid (77%, 269 mg, 1.2 mmol) was added in small portions to a stirred solution of 3-(4-fluorophenylsulfanyl)-2,4,5,6-tetramethyl-1-benzofuran (330 mg, 1.1 mmol) in dichloromethane (35 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 (hexane–ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [yield 74%, m.p. 443–444 K; R_f = 0.59 (hexane–ethyl acetate, 2:1 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.