3-Ethyl­sulfinyl-2-(3-fluoro­phen­yl)-5,6-methyl­enedi­oxy-1-benzofuran

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S1600536812044832

. 2012 Nov 14;68(Pt 12):o3339. doi: 10.1107/S1600536812044832

3-Ethylsulfinyl-2-(3-fluorophenyl)-5,6-methylenedioxy-1-benzofuran

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

PMCID: PMC3588941 PMID: 23476177

Abstract

In the title compound, C₁₇H₁₃FO₄S, the 3-fluorophenyl ring makes a dihedral angle of 6.14 (5)° with the mean plane [r.m.s. deviation = 0.008 (1) Å] of the benzofuran fragment. In the crystal, molecules are linked by weak C—H⋯F, C—H⋯O and C—H⋯π interactions, forming a three--dimensional network. The crystal structure also exhibits slipped π–π interactions between the 3-fluorophenyl rings of neighbouring molecules [centroid–centroid distance = 3.769 (2) Å and slippage = 1.684 (2) Å].

Related literature

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

Experimental

Crystal data

C₁₇H₁₃FO₄S
M _r = 332.33
Monoclinic,
a = 8.8516 (2) Å
b = 21.8221 (4) Å
c = 7.7228 (2) Å
β = 102.949 (1)°
V = 1453.80 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 173 K
0.39 × 0.29 × 0.26 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.908, T _max = 0.937
14376 measured reflections
3600 independent reflections
3131 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.101
S = 1.02
3600 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.45 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 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Click here for additional data file.^{(25.1KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812044832/mw2094sup1.cif

e-68-o3339-sup1.cif^{(25.1KB, cif)}

Click here for additional data file.^{(176.5KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812044832/mw2094Isup2.hkl

e-68-o3339-Isup2.hkl^{(176.5KB, hkl)}

Click here for additional data file.^{(5.8KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812044832/mw2094Isup3.cml

Additional supplementary materials: 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
C9—H9A⋯O4ⁱ	0.99	2.45	3.314 (2)	145
C9—H9B⋯O2ⁱⁱ	0.99	2.59	3.519 (3)	156
C16—H16A⋯O4ⁱⁱⁱ	0.99	2.29	3.2689 (19)	169
C6—H6⋯F1^iv	0.95	2.37	3.2532 (18)	154
C17—H17B⋯Cg1^v	0.98	2.74	3.642 (3)	153

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

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 5,6-methylenedioxy-1-benzofuran derivatives containing [3-ethylsulfinyl-2-(4-fluorophenyl)] (Choi et al., 2010) and [2-(4-fluorophenyl)-3-isopropylsulfinyl] (Seo et al., 2011) 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 0.008 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 3-fluorophenyl ring and the mean plane of the benzofuran fragment is 6.14 (5)°. In the crystal structure (Figs. 2 & 3), molecules are connected by weak C—H···F, C—H···O and C—H···π interactions (Table 1, Cg1 is the centroid of the C2–C7 benzene ring). The crystal packing (Fig. 3) also exhibits slipped π–π interactions between the 3-fluorophenyl rings of neighbouring molecules, with a Cg2···Cg2^vi distance of 3.769 (2) Å and an interplanar distance of 3.372 (2) Å resulting in a slippage of 1.684 (2) Å (Cg2 is the centroid of the C10–C15 3-fluorophenyl ring).

Experimental

3-Chloroperoxybenzoic acid (77%, 224 mg, 1.0 mmol) was added in small portions to a stirred solution of 3-ethylsulfanyl-2-(3-fluorophenyl)-5,6-methylenedioxy-1-benzofuran (284 mg, 0.9 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 4h, 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, 1:1 v/v) to afford the title compound as a colorless solid [yield 73%, m.p. 408–409 K; R_f = 0.61 (hexane–ethyl acetate, 1:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in acetone at room temperature.