3-(4-Fluoro­phenyl­sulfin­yl)-5-iodo-2,7-dimethyl-1-benzofuran

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

doi:10.1107/S1600536811012591

. 2011 Apr 13;67(Pt 5):o1082. doi: 10.1107/S1600536811012591

3-(4-Fluorophenylsulfinyl)-5-iodo-2,7-dimethyl-1-benzofuran

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

PMCID: PMC3089076 PMID: 21754404

Abstract

In the title compound, C₁₆H₁₂FlO₂S, the 4-fluorophenyl ring makes a dihedral angle of 80.21 (6)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked through weak intermolecular C—H⋯O hydrogen bonds. The crystal structure also exhibits an intermolecular I⋯F contact [3.423 (2) Å].

Related literature

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 our previous structural studies of related 3-(4-fluorophenylsulfinyl)-5-halo-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010a ▶,b ▶,c ▶).

Experimental

Crystal data

C₁₆H₁₂FIO₂S
M _r = 414.22
Triclinic,
a = 9.0845 (2) Å
b = 9.2761 (2) Å
c = 10.1252 (2) Å
α = 71.315 (1)°
β = 80.838 (1)°
γ = 70.485 (1)°
V = 760.53 (3) Å³
Z = 2
Mo Kα radiation
μ = 2.25 mm⁻¹
T = 173 K
0.25 × 0.23 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.603, T _max = 0.666
13286 measured reflections
3477 independent reflections
3276 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.025
wR(F ²) = 0.065
S = 1.15
3477 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −1.25 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 datablocks global, I. DOI: 10.1107/S1600536811012591/bv2179sup1.cif

e-67-o1082-sup1.cif^{(18.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012591/bv2179Isup2.hkl

e-67-o1082-Isup2.hkl^{(170.5KB, hkl)}

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
C3—H3⋯O2ⁱ	0.95	2.51	3.444 (3)	169
C9—H9A⋯O2ⁱⁱ	0.98	2.48	3.437 (3)	165
C15—H15⋯O1ⁱⁱⁱ	0.95	2.49	3.342 (3)	149

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

supplementary crystallographic information

Comment

A series of benzofuran ring system have attracted much attention owing to their interesting pharmacological properties such as antifungal, antitumor and antiviral, antimicrobial activities (Aslam et al., 2006, Galal et al., 2009, Khan et al., 2005). These compounds widely occur in nature (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our study of the substituent effect on the solid state structures of 3-(4-fluorophenylsulfinyl)-5-halo-2-methyl-1-benzofuran analogues (Choi et al., 2010a,b,c), we report here 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 0.009 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the mean plane of the benzofuran fragment and the 4-fluorophenyl ring is 80.21 (6)°. The molecular packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds; the first one between a benzene H atom and the oxygen of the S═O unit (Table 1: C3—H3···O2ⁱ), and the second one between a methyl H atom and the oxygen of the S═O unit (Table 1: C9—H9A···O2ⁱⁱ), and the third one between a 4-fluorophenyl H atom and the furan O atom (Table 1; C15—H15···O1ⁱⁱⁱ). The crystal packing (Fig. 2) is further stabilized by an I···F contact at 3.423 (2) Å [C4—I1···F1^iv = 161.10 (6) ° ].

Experimental

77% 3-chloroperoxybenzoic acid (202 mg, 0.9 mmol) was added in small portions to a stirred solution of 3-(4-fluorophenylsulfanyl)-5-iodo-2,7-dimethyl-1-benzofuran (318 mg, 0.8 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 72%, m.p. 423–424 K; Rf = 0.65 (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.