3-(2-Fluoro­phenyl­sulfon­yl)-2,5,7-trimethyl-1-benzo­furan

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S1600536814007909

. 2014 Apr 16;70(Pt 5):o566. doi: 10.1107/S1600536814007909

3-(2-Fluorophenylsulfonyl)-2,5,7-trimethyl-1-benzofuran

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

PMCID: PMC4011256 PMID: 24860371

Abstract

In the title compound, C₁₇H₁₅FO₃S, the dihedral angle between the mean planes of the benzofuran and 2-fluorophenyl rings is 87.61 (4) Å. In the crystal, molecules are linked via pairs of C—H⋯π interactions into inversion-related dimers. These dimers are linked by C—H⋯O hydrogen bonds into supramolecular chains running along the a-axis direction.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010 ▶, 2012 ▶); Seo et al. (2011 ▶).

Experimental

Crystal data

C₁₇H₁₅FO₃S
M _r = 318.35
Triclinic,
a = 7.7658 (2) Å
b = 8.3529 (3) Å
c = 12.9732 (4) Å
α = 74.253 (2)°
β = 75.048 (2)°
γ = 66.046 (1)°
V = 729.66 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 173 K
0.34 × 0.26 × 0.23 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.700, T _max = 0.746
13247 measured reflections
3498 independent reflections
3057 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.104
S = 1.04
3498 reflections
202 parameters
H-atom parameters constrained
Δρ_max = 0.34 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 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/S1600536814007909/zq2222sup1.cif

e-70-0o566-sup1.cif^{(24.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814007909/zq2222Isup2.hkl

e-70-0o566-Isup2.hkl^{(171.5KB, hkl)}

Click here for additional data file.^{(5.9KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814007909/zq2222Isup3.cml

CCDC reference: 996303

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

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

Cg1 is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O2ⁱ	0.95	2.58	3.462 (2)	155
C9—H9C⋯Cg1ⁱⁱ	0.98	2.79	3.612 (2)	142

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

supplementary crystallographic information

1. Comment

As a part of our ongoing study of 2,5,7-trimethyl-1-benzofuran derivatives containing 4-fluorophenylsulfonyl (Choi et al., 2010), 3-fluorophenylsulfonyl (Seo et al., 2011) and 4-methylphenylsulfonyl (Choi et al., 2012) substituents in the 3-position, we report here on the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran ring system is essentially planar, with a mean deviation of 0.013 (1) Å from the least-squares plane defined by the nine constituent atoms. The 2-fluorophenyl ring is essentially planar, with a mean deviation of 0.004 (1) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring system and the 2-fluorophenyl ring is 87.61 (4)°. In the crystal structure (Fig. 2), molecules are linked via pairs of C—H···π interactions (Table 1, Cg1 is the centroid of the C2–C7 benzene ring) into inversion-related dimers. These dimers are further linked by C—H···O hydrogen bonds (Table 1), forming supramolecular chains running along the a-axis direction.

2. Experimental

3-Chloroperoxybenzoic acid (77%, 448 mg, 2.0 mmol) was added in small portions to a stirred solution of 3-(2-fluorophenylsulfanyl)-2,5,7-trimethyl-1-benzofuran (257 mg, 0.9 mmol) in dichloromethane (35 mL) at 273 K. After being stirred at room temperature for 10h, 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 71%, m.p. 409–410 K; R_f = 0.52 (benzene)]. Single crystals suitable for X-ray diffraction were prepared by slow vaporation of a solution of the title compound in acetone at room temperature.