Crystal structure of 5-fluoro-2-(3-fluoro­phen­yl)-3-methyl­sulfinyl-1-benzo­furan

Hong Dae Choi; Uk Lee

doi:10.1107/S160053681402251X

. 2014 Oct 18;70(Pt 11):o1168. doi: 10.1107/S160053681402251X

Crystal structure of 5-fluoro-2-(3-fluorophenyl)-3-methylsulfinyl-1-benzofuran

Hong Dae Choi ^a, Uk Lee ^b,^*

PMCID: PMC4257342 PMID: 25484808

Abstract

In the title compound, C₁₅H₁₀F₂O₂S, the dihedral angle between the planes of the benzofuran ring system [r.m.s. deviation = 0.015 (1) Å] and the 3-fluorophenyl ring is 26.60 (5)°. In the crystal, molecules are linked by C—H⋯O and C—H⋯F hydrogen bonds, and by π–π interactions between the benzofuran rings of inversion-related molecules [centroid(benzene)–centroid(furan) distance = 3.819 (2) Å], forming a three-dimensional network.

Keywords: crystal structure, benzofuran, 3-fluorophenyl, π–π interactions.

Related literature

For a related structure and background to benzofuran derivatives, see: Choi & Lee (2014 ▶). For further synthetic details, see: Choi et al. (1999 ▶).

Experimental

Crystal data

C₁₅H₁₀F₂O₂S
M _r = 292.29
Monoclinic,
a = 8.4826 (2) Å
b = 16.6307 (4) Å
c = 9.7493 (2) Å
β = 113.756 (1)°
V = 1258.81 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 173 K
0.62 × 0.55 × 0.42 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.846, T _max = 0.892
12021 measured reflections
3111 independent reflections
2736 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.098
S = 1.03
3111 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.35 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/S160053681402251X/fy2119sup1.cif

e-70-o1168-sup1.cif^{(370.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681402251X/fy2119Isup2.hkl

e-70-o1168-Isup2.hkl^{(152.7KB, hkl)}

Click here for additional data file.^{(4.9KB, cml)}

Supporting information file. DOI: 10.1107/S160053681402251X/fy2119Isup3.cml

Click here for additional data file.^{(387.1KB, tif)}

. DOI: 10.1107/S160053681402251X/fy2119fig1.tif

The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.

Click here for additional data file.^{(695.7KB, tif)}

x y z x y z x y z x y z x y z x y z x y z x y z . DOI: 10.1107/S160053681402251X/fy2119fig2.tif

A view of the C—H⋯O, C—H⋯F and π–π interactions (dotted lines) in the crystal structure of the title compound. H atoms not participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) − x + 2, y − Inline graphic , − z + ; (ii) x − 1, y, z − 1; (iii) − x + 2, − y + 1, − z + 2; (iv) x, y, z + 1; (v) − x + 2, − y + 1, − z + 1; (vi) − x + 2, y + , − z + ; (vii) x + 1, y, z + 1; (viii) − x + 2, y + , − z + .]

CCDC reference: 1029041

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

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
C5H5O2ⁱ	0.95	2.45	3.2612(18)	143
C12H12O2ⁱⁱ	0.95	2.42	3.3361(19)	161
C15H15AF1ⁱⁱⁱ	0.98	2.54	3.409(2)	147
C15H15BF2^iv	0.98	2.55	3.163(2)	121

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

Acknowledgments

The X-ray centre of the Gyeongsang National University is acknowledged for providing access to the single-crystal diffractometer.

supplementary crystallographic information

S1. Comment

As a part of our continuing program for benzofuran derivatives (Choi & Lee, 2014), 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 0.015 (1) Å from the least-squares plane defined by the nine constituent atoms. The 3-fluorophenyl ring is essentially planar, with a mean deviation of 0.009 (1) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring and the 3-fluorophenyl ring is 26.60 (5)°. In the crystal structure (Fig. 2), molecules are linked by C—H···O and C—H···F hydrogen bonds (Table 1), and by π–π interactions between the benzene and furan rings of neighbouring molecules, with a Cg1···Cg2^v distance of 3.819 (2) Å and an interplanar distance of 3.283 (2) Å resulting in a slippage of 1.951 (2) Å (Cg1 and Cg2 are the centroids of the C2–C7 benzene ring and C1/C2/C7/O1/C8 furan ring, respectively), forming a three-dimensional network.

S2. Experimental

The starting material 5-fluoro-2-(3-fluorophenyl)-3-methylsulfanyl-1-benzofuran was prepared by literature method (Choi et al., 1999). 3-Chloroperoxybenzoic acid (77%, 269 mg, 1.2 mmol) was added in small portions to a stirred solution of 5-fluoro-2-(3-fluorophenyl)-3-methylsulfanyl-1-benzofuran (304 mg, 1.1 mmol) in dichloromethane (30 ml) at 273 K. After being stirred at room temperature for 8h, the mixture was washed with saturated sodium bicarbonate solution (2 × 10 ml) 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, 1:2 v/v) to afford the title compound as a colorless solid [yield 71% (207 mg); m.p. 459–460 K; R_f = 0.48 (hexane–ethyl acetate, 1:2 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound (24 mg) in acetone (20 ml) at room temperature.