2,5,7-Trimethyl-3-(4-methyl­phenyl­sulfon­yl)-1-benzofuran

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S160053681202020X

. 2012 May 16;68(Pt 6):o1751. doi: 10.1107/S160053681202020X

2,5,7-Trimethyl-3-(4-methylphenylsulfonyl)-1-benzofuran

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

PMCID: PMC3379338 PMID: 22719536

Abstract

In the title compound, C₁₈H₁₈O₃S, the 4-methylphenyl ring makes a dihedral angle of 86.35 (3)° with the mean plane [mean deviation = 0.006 (1) Å] of the benzofuran fragment. In the crystal, molecules are linked by weak C—H⋯O and C—H⋯π interactions. The crystal structure also exhibits weak π–π interactions between the furan and benzene rings of neighbouring benzofuran systems [centroid–centroid distance = 3.685 (2), interplanar distance = 3.572 (2) and slippage = 0.906 (2) Å].

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2008 ▶, 2010 ▶); Seo et al. (2011 ▶). graphic file with name e-68-o1751-scheme1.jpg

Experimental

Crystal data

C₁₈H₁₈O₃S
M _r = 314.38
Monoclinic,
a = 9.7666 (2) Å
b = 19.4511 (5) Å
c = 8.2979 (2) Å
β = 98.541 (1)°
V = 1558.88 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 173 K
0.41 × 0.39 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.916, T _max = 0.958
15446 measured reflections
3868 independent reflections
3258 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.116
S = 1.04
3868 reflections
203 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.43 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 datablock(s) global, I. DOI: 10.1107/S160053681202020X/sj5234sup1.cif

e-68-o1751-sup1.cif^{(25.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202020X/sj5234Isup2.hkl

e-68-o1751-Isup2.hkl^{(189.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681202020X/sj5234Isup3.cml

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

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

Cg1 and Cg2 are the centroids of the C12–C17 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10C⋯O3ⁱ	0.98	2.46	3.310 (2)	146
C9—H9C⋯Cg1ⁱⁱ	0.98	2.93	3.907 (2)	179
C10—H10B⋯Cg2ⁱⁱⁱ	0.98	2.92	3.800 (2)	150

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

supplementary crystallographic information

Comment

As a part of our ongoing study of 2,5,7-trimethyl-1-benzofuran derivatives containing 3-phenylsulfonyl (Choi et al., 2008), 3-(4-fluorophenylsulfonyl) (Choi et al., 2010) and 3-(3-fluorophenylsulfonyl) (Seo et al., 2011) substituents, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.006 (1) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 4-methylphenyl ring and the mean plane of the benzofuran fragment is 86.35 (3)°. In the crystal structure (Fig. 2), molecules are connected by weak intermolecular C—H···O and C—H···π interactions (Table 1). The crystal packing (Fig. 2) also exhibits weak π···π interactions between the furan and benzene rings of neighbouring benzofuran systems, with a Cg2···Cg3ⁱ distance of 3.685 (2) Å and an interplanar distance of 3.572 (2) Å resulting in a slippage of 0.906 (2) Å (Cg3 is the centroid of the C2–C7 benzene ring).

Experimental

3-Chloroperoxybenzoic acid (77%, 560 mg, 2.5 mmol) was added in small portions to a stirred solution of 2,5,7-trimethyl-3-(4-methylphenylsulfanyl)-1-benzofuran (338 mg, 1.2 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 10h, 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, 4:1 v/v) to afford the title compound as a colorless solid [yield 78%, m.p. 413–414 K; R_f = 0.48 (hexane–ethyl acetate, 4:1 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.