2-(4-Fluoro­phen­yl)-3-isopropyl­sulfinyl-5,6-methyl­enedi­oxy-1-benzofuran

Pil Ja Seo; Hong Dae Choi; Byeng Wha Son; Uk Lee

doi:10.1107/S1600536811051178

. 2011 Nov 30;67(Pt 12):o3504. doi: 10.1107/S1600536811051178

2-(4-Fluorophenyl)-3-isopropylsulfinyl-5,6-methylenedioxy-1-benzofuran

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

PMCID: PMC3239126 PMID: 22199974

Abstract

In the title compound, C₁₈H₁₅FO₄S, the fluorobenzene ring makes a dihedral angle of 4.3 (1)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds. The O atom of the sulfinyl group is disordered over two orientations, with site-occupancy factors of 0.940 (3) and 0.060 (3).

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For the crystal structures of related compounds, see: Choi et al. (2010a ▶,b ▶).

Experimental

Crystal data

C₁₈H₁₅FO₄S
M _r = 346.36
Triclinic,
a = 6.2519 (1) Å
b = 9.6773 (2) Å
c = 12.9267 (2) Å
α = 90.122 (1)°
β = 94.726 (1)°
γ = 101.920 (1)°
V = 762.47 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 173 K
0.45 × 0.21 × 0.14 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.898, T _max = 0.967
13552 measured reflections
3488 independent reflections
3171 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.101
S = 1.06
3488 reflections
229 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.56 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/S1600536811051178/fj2487sup1.cif

e-67-o3504-sup1.cif^{(26.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051178/fj2487Isup2.hkl

e-67-o3504-Isup2.hkl^{(171KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811051178/fj2487Isup3.cml

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5B⋯O4Aⁱ	0.99	2.27	3.231 (2)	163
C18—H18A⋯O4Aⁱⁱ	0.98	2.49	3.354 (2)	147

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

supplementary crystallographic information

Comment

Recently, substituted benzofuran derivatives have drawn much attention due to their valuable pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2009, Galal et al., 2009, Khan et al., 2005). These benzofuran derivatives occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing study of 5,6-(methylenedioxy)benzofuran derivatives containing either 3-methylsulfinyl (Choi et al., 2010a) or 3-ethylsulfinyl (Choi et al., 2010b) 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 0.006 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the 4-fluorophenyl ring and the mean plane of the benzofuran fragment is 4.3 (1)°. The O atom of the sulfinyl group is disordered over two positions with site-occupancy factors, from refinement, of 0.940 (3) (Part A) and 0.060 (3) (part B). The crystal packing is stabilized by weak intermolecular C—H···O hydrogen bonds; the first one between a methylene H atom and the O atom of the S═O unit (Table 1, first entry & Fig. 2), and the second one between a methyl H atom of the isopropyl group and the O atom of the S═O unit (Table 1, second entry & Fig. 2).

Experimental

77% 3-chloroperoxybenzoic acid (224 mg, 1.0 mmol) was added in small portions to a stirred solution of 2-(4-fluorophenyl)-3-isopropylsulfanyl-5,6-methylenedioxy-1-benzofuran (251 mg, 0.8 mmol) in dichloromethane (30 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, 1:2 v/v) to afford the title compound as a colorless solid [yield 71%, m.p. 437–438 K; R_f = 0.55 (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 in ethyl acetate at room temperature.