2-(4-Fluoro­phen­yl)-3-methyl­sulfinyl-5-phenyl-1-benzofuran

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

doi:10.1107/S1600536810014613

. 2010 Apr 24;66(Pt 5):o1167. doi: 10.1107/S1600536810014613

2-(4-Fluorophenyl)-3-methylsulfinyl-5-phenyl-1-benzofuran

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

PMCID: PMC2979132 PMID: 21579209

Abstract

In the title molecule, C₂₁H₁₅FO₂S, the O atom and the methyl group of the methylsulfinyl substituent are situated on the opposite sides of the plane through the benzofuran fragment. The benzofuran ring plane makes dihedral angles of 28.63 (6) and 31.55 (5)° with the 4-fluorophenyl and phenyl rings, respectively. Weak C—H⋯F and C—H⋯O hydrogen bonds and intermolecular C—H⋯π interactions are present in the crystal structure. The title crystal was refined as an inversion twin with a 0.39 (7):0.61 (7) domain ratio.

Related literature

For the crystal structures of similar 3-alkylsulfanyl-2-(4-fluorophenyl)-5-phenyl-1-benzofuran derivatives, see: Choi et al. (2009 ▶, 2010 ▶). For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For hydrogen bonding, see: Desiraju & Steiner (1999 ▶).

Experimental

Crystal data

C₂₁H₁₅FO₂S
M _r = 350.39
Monoclinic,
a = 10.148 (2) Å
b = 7.117 (1) Å
c = 11.991 (2) Å
β = 110.047 (2)°
V = 813.6 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 173 K
0.40 × 0.40 × 0.25 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.917, T _max = 0.947
4812 measured reflections
3226 independent reflections
3065 reflections with I > 2σ(I)
R _int = 0.019

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.086
S = 1.06
3226 reflections
228 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ▶), 1308 Friedel pairs
Flack parameter: 0.39 (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 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810014613/fb2185sup1.cif

e-66-o1167-sup1.cif^{(20.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014613/fb2185Isup2.hkl

e-66-o1167-Isup2.hkl^{(158.2KB, hkl)}

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

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

Cg1 and Cg2 are the centroids of the C15–C20 (5-phenyl) and the C9–14 (4-fluorophenyl) rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O2ⁱ	0.93	2.61	3.301 (3)	131
C21—H21A⋯O2ⁱⁱ	0.96	2.63	3.375 (3)	135
C21—H21B⋯Fⁱⁱⁱ	0.96	2.55	3.478 (3)	164
C10—H10⋯Cg1^iv	0.93	2.86	3.450 (2)	122
C13—H13⋯Cg2ⁱⁱⁱ	0.93	2.81	3.417 (2)	124

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

supplementary crystallographic information

Comment

The compounds with the benzofuran skeleton show significant pharmacological activities such as fungicide (Aslam et al., 2006), antitumor and antiviral (Galal et al., 2009) and antimicrobial (Khan et al., 2005) properties. These compounds are common in Nature (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing studies of the effect of the side chain substituents on the solid state structures of 3-alkylsulfanyl-2-(4-fluorophenyl)-5-phenyl-1-benzofuran analogues (Choi et al., 2009, 2010), we report the title crystal structure. The title molecule is depicted in Fig. 1.

The benzofuran ring is essentially planar, with a mean deviation of 0.006 (2) Å from the least-squares plane defined by the nine constituent atoms. In the molecule, the benzofuran plane makes dihedral angles of 28.63 (6) and 31.55 (5)° with the 4-fluorophenyl ring and the phenyl ring, respectively. The molecular packing (Fig. 2) is stabilized by an intermolecular C—H···F hydrogen bond between the methyl H atom and the fluorine (Tab. 1). There are also C—H···O interactions (Tab. 1 and Fig. 2) with geometrical parameters that are on the limit of their acceptance as true weak C—H···O hydrogen bonds (Desiraju & Steiner, 1999). The molecular packing (Fig. 3) is further stabilized by two intermolecular C—H···π-electron ring interactions: The first one between the 4-fluorophenyl H atom and the 5-phenyl ring, and the second one between the 4-fluorophenyl H atom and 4-fluorophenyl ring (Tab. 1).

Experimental

77% 3-chloroperoxybenzoic acid (224 mg, 1.0 mmol) was added in small portions to a stirred solution of 2-(4-fluorophenyl)-3-methylsulfanyl-5-phenyl-1-benzofuran (301 mg, 0.9 mmol) in dichloromethane (30 ml) at 273 K. After having been stirred at room temperature for 4h, the mixture was washed with saturated sodium hydrogencarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (silica gel, hexane–ethyl acetate, 1:1 v/v) to afford the title compound as a colourless solid [yield 80%, m.p. 506–507 K; R_f = 0.59 (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 chloroform at room temperature. The average crystal size was approximately 1.0 × 1.0 × 0.5 mm. (The measured crystal was cut from the larger one.) The crystals are colourless and soluble in polar solvents.