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

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

doi:10.1107/S1600536811036713

. 2011 Sep 30;67(Pt 10):o2742. doi: 10.1107/S1600536811036713

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

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

PMCID: PMC3201533 PMID: 22065057

Abstract

In the title compound, C₂₁H₁₅FOS, the dihedral angle between the mean plane of the benzofuran fragment and the mean planes of the pendant 4-fluorobenzene and phenyl rings are 31.72 (6)° and 32.51 (6)°, respectively. In the crystal, the molecules are linked by weak C—H⋯π interactions. The crystal studied was a merohedral twin with a 0.62 (9):0.38 (9) domain ratio.

Related literature

For background to 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 structural studies of 2-(4-halophenyl)-3-methylsulfanyl-5-phenyl-1-benzofuran drivatives, see: Choi et al. (2009 ▶, 2010 ▶).

Experimental

Crystal data

C₂₁H₁₅FOS
M _r = 334.39
Monoclinic,
a = 10.6439 (15) Å
b = 7.2006 (10) Å
c = 11.7226 (17) Å
β = 115.396 (2)°
V = 811.6 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 173 K
0.36 × 0.29 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.928, T _max = 0.979
7372 measured reflections
3194 independent reflections
2540 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.106
S = 1.10
3194 reflections
219 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack (1983 ▶), 1278 Friedel pairs
Flack parameter: 0.38 (9)

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/S1600536811036713/hb6402sup1.cif

e-67-o2742-sup1.cif^{(25.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036713/hb6402Isup2.hkl

e-67-o2742-Isup2.hkl^{(156.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811036713/hb6402Isup3.cml

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

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

Cg is the centroid of the C15–C20 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯Cgⁱ	0.95	2.76	3.448 (2)	130

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Recently, many compounds having a benzofuran moiety 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 studies of the substituent effect on the solid state structures of 2-(4-halophenyl)-3-methylsulfanyl-5-phenyl-1-benzofuran analogues (Choi et al., 2009, 2010), we report herein the crystal structure of the title compound.

The title compound crystallizes as the non-centrosymmetric space group P₂₁ in spite of having no asymmetric C atoms. The crystal studied was an inversion twin with a 0.68 (9) : 0.32 (9) domain ratio.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.006 (2) 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 benzofurn fragment is 31.72 (6)°. The dihedral angle between the phenyl ring and the mean plane of the benzofurn fragment is 32.51 (6)°. The crystal packing (Fig. 2) is stabilized by intermolecular C—H···π interactions between a 4-fluorophenyl H atom and the phenyl ring (Table 1; C14—H14···Cgⁱ, Cg is the centroid of the C15–C20 phenyl ring).

Experimental

Zinc chloride (273 mg, 2.0 mmol) was added to a stirred solution of 4-fluoro-4'-hydroxybiphenyl (376 mg, 2.0 mmol) and 2-chloro-2-methylsulfanylacetophenone (401 mg, 2.0 mmol) in dichloromethane (30 mL) at room temperature, and stirring was continued at the same temperature for 1 h. The reaction was quenched by the addition of water and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane–benzene, 5:2 v/v) to afford the title compound as a colorless solid [yield 61%, m.p. 415–416 K; R_f = 0.78 (hexane–benzene, 5:2 v/v)]. Colourless blocks were prepared by slow evaporation of a solution of the title compound in carbon tetrachloride at room temperature.