2,4,5,6-Tetra­methyl-3-phenyl­sulfinyl-1-benzofuran

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

doi:10.1107/S1600536811018952

. 2011 May 25;67(Pt 6):o1512. doi: 10.1107/S1600536811018952

2,4,5,6-Tetramethyl-3-phenylsulfinyl-1-benzofuran

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

PMCID: PMC3120578 PMID: 21754877

Abstract

In the title compound, C₁₈H₁₈O₂S, the phenyl ring makes a dihedral angle of 87.47 (6)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions.

Related literature

For the biological 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 related 2-methyl-3-phenylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2008a ▶,b ▶,c ▶).

Experimental

Crystal data

C₁₈H₁₈O₂S
M _r = 298.38
Monoclinic,
a = 14.2611 (5) Å
b = 6.0661 (2) Å
c = 17.2436 (7) Å
β = 99.740 (2)°
V = 1470.23 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 173 K
0.29 × 0.20 × 0.14 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.622, T _max = 0.746
25036 measured reflections
3397 independent reflections
2888 reflections with I > 2σ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.155
S = 1.04
3397 reflections
188 parameters
H-atom parameters constrained
Δρ_max = 1.20 e Å⁻³
Δρ_min = −0.56 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/S1600536811018952/jj2090sup1.cif

e-67-o1512-sup1.cif^{(18.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018952/jj2090Isup2.hkl

e-67-o1512-Isup2.hkl^{(166.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811018952/jj2090Isup3.cml

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

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

Cg is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2ⁱ	0.95	2.35	3.286 (3)	169
C10—H10A⋯O2ⁱⁱ	0.98	2.56	3.517 (3)	167
C12—H12C⋯Cgⁱⁱⁱ	0.98	2.66	3.482 (3)	142

Open in a new tab

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

supplementary crystallographic information

Comment

Recently, a series of compounds containing the benzofuran ring system have been shown to exhibit significant pharmacological properties such as antibacterial, antifungal, antitumor, antiviral, and antimicrobial activities (Aslam et al. , 2009, Galal et al. , 2009, Khan et al. , 2005). These types of compounds occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al. , 2003). As a part of our study of the substituent effect on the solid state structures of 2-methyl-3-phenylsulfinyl-1-benzofuran analogues (Choi et al., 2008a,b,c), we report hrerin the crystal structure of the title compound, C₁₈H₁₈O₂S.

In the title compound (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.017 (1) Å from the least-squares plane defined by the nine constituent atoms. The phenyl ring makes a dihedral angle of 87.47 (6)° with the mean plane of the benzofuran fragment. Crystal packing is stabilized by weak intermolecular C—H···O hydrogen bonds (Table 1 & Fig. 2) and weak C—H···Cg π–ring interactions (Table 1 & Fig 3; Cg is the centroid of the C2–C7 benzene ring).

Experimental

77% 3-chloroperoxybenzoic acid (247 mg, 1.1 mmol) was added in small portions to a stirred solution of 2,4,5,6-tetramethyl-3-phenylsulfanyl-1-benzofuran (310 mg, 1.1 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, 2:1 v/v) to afford the title compound as a colorless solid [yield 74%, m.p. 438–439 K; R_f = 0.51 (hexane–ethyl acetate, 2:1 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.