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

Hong Dae Choi; Uk Lee

doi:10.1107/S1600536814017966

. 2014 Aug 9;70(Pt 9):o991–o992. doi: 10.1107/S1600536814017966

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

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

PMCID: PMC4186186 PMID: 25309297

Abstract

In the title compound, C₁₅H₁₀ClFO₂S, the dihedral angle between the plane of the benzofuran ring system [r.m.s. deviation = 0.013 (1) Å] and that of the 3-fluorophenyl ring [r.m.s. deviation = 0.005 (1) Å] is 31.36 (5)°. In the crystal, molecules are linked by two different pairs of C—H⋯O hydrogen bonds, forming inversion dimers.

Keywords: crystal structure, benzofuran, 3-fluorophenyl, C—H⋯O hydrogen bonds

Related literature

For the pharmaceutical properties of compounds containing the benzofuran moiety, see: Aslam et al. (2009 ▶); Choi et al. (2003 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶); Ono et al. (2002 ▶). For natural products with a benzofuran ring, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For the synthesis of the starting material 5-chloro-2-(3-fluorophenyl)-3-methylsulfanyl-1-benzofuran, see: Choi et al. (1999 ▶). For a related structure, see: Choi et al. (2009 ▶).

Experimental

Crystal data

C₁₅H₁₀ClFO₂S
M _r = 308.74
Triclinic,
a = 8.0038 (1) Å
b = 8.4322 (1) Å
c = 10.6782 (2) Å
α = 88.933 (1)°
β = 81.008 (1)°
γ = 66.859 (1)°
V = 653.81 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.46 mm⁻¹
T = 173 K
0.47 × 0.34 × 0.33 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.813, T _max = 0.863
11737 measured reflections
3124 independent reflections
2887 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.086
S = 1.07
3124 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.44 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/S1600536814017966/zq2226sup1.cif

e-70-0o991-sup1.cif^{(23KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814017966/zq2226Isup2.hkl

e-70-0o991-Isup2.hkl^{(153.3KB, hkl)}

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

Supporting information file. DOI: 10.1107/S1600536814017966/zq2226Isup3.cml

Click here for additional data file.^{(1.2MB, tif)}

. DOI: 10.1107/S1600536814017966/zq2226fig1.tif

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

Click here for additional data file.^{(1.5MB, tif)}

x y z x y z . DOI: 10.1107/S1600536814017966/zq2226fig2.tif

A view of the C—H⋯O hydrogen bonds (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity [symmetry codes: (i) − x, − y + 1, − z + 1; (ii) − x + 1, − y, − z + 1].

CCDC reference: 1017893

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O2ⁱ	0.95	2.57	3.3470 (18)	139
C14—H14⋯O2ⁱⁱ	0.95	2.59	3.4884 (17)	157

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

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

Recently, a number of benzofuran compounds have drawn much attention owing to their interesting pharmaceutical properties such as antibacterial and antifungal, antitumor and antiviral, antimicrobial activities (Aslam et al. 2009; Galal et al., 2009; Khan et al., 2005), and potential inhibitors of β-amyloid formation (Choi et al., 2003, Ono et al., 2002). These benzofuran derivatives occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing project of 2-aryl-5-chloro-3-methylsulfinyl-1-benzofuran derivatives containing 4-fluorophenyl substituent in 2-position (Choi et al., 2009), 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 0.013 (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 0.005 (1) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring system and the 3-fluorophenyl ring is 31.36 (5)°. In the crystal structure (Fig. 2), molecules are linked by two different pairs of C—H···O hydrogen bonds (Table 1), forming inversion dimers.

S2. Experimental

The starting material 5-chloro-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 the starting material (322 mg, 1.1 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 6h, the mixture was washed with saturated sodium bicarbonate solution (2 X 20 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, 1:1 v/v) to afford the title compound as a colorless solid [yield 73% (248 mg); m.p. 483–484 K; R_f = 0.48 (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 (120 mg) in acetone (20 mL) at room temperature.