2,5-Dimethyl-3-(4-methyl­phenyl­sulfin­yl)-1-benzofuran

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S1600536812015450

. 2012 Apr 18;68(Pt 5):o1410. doi: 10.1107/S1600536812015450

2,5-Dimethyl-3-(4-methylphenylsulfinyl)-1-benzofuran

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

PMCID: PMC3344536 PMID: 22590298

Abstract

In the title compound, C₁₇H₁₆O₂S, the 4-methylphenyl ring makes a dihedral angle of 88.28 (5)° with the mean plane [mean deviation = 0.009 (1) Å] of the benzofuran fragment. In the crystal, molecules are linked by weak C—H⋯O and C—H⋯π interactions.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010a ▶,b ▶, 2012 ▶).

Experimental

Crystal data

C₁₇H₁₆O₂S
M _r = 284.36
Orthorhombic,
a = 13.072 (2) Å
b = 6.1790 (11) Å
c = 17.979 (3) Å
V = 1452.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 173 K
0.37 × 0.23 × 0.14 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.624, T _max = 0.746
13920 measured reflections
3587 independent reflections
3101 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.090
S = 1.03
3587 reflections
184 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ▶), 1729 Friedel pairs
Flack parameter: −0.01 (7)

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/S1600536812015450/fy2054sup1.cif

e-68-o1410-sup1.cif^{(24.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015450/fy2054Isup2.hkl

e-68-o1410-Isup2.hkl^{(175.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812015450/fy2054Isup3.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
C12—H12⋯O2ⁱ	0.95	2.60	3.334 (2)	134
C17—H17B⋯O1ⁱⁱ	0.98	2.52	3.387 (3)	148
C10—H10B⋯Cgⁱⁱⁱ	0.98	2.74	3.538 (3)	139

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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-dimethyl-1-benzofuran derivatives containing 3-(4-fluorophenylsulfinyl) (Choi et al., 2010a), 3-(4-chlorophenylsulfinyl) (Choi et al., 2010b) and 3-(4-bromophenylsulfinyl) (Choi et al., 2012) 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 0.009 (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 benzofurn fragment is 88.28 (5)°. In the crystal structure, molecules are connected by weak intermolecular C—H···O hydrogen bonds (Fig. 2 & Table 1) and C—H···π interactions (Fig. 3 & Table 1, Cg is the centroid of the C2–C7 benzene ring).

Experimental

3-Chloroperoxybenzoic acid (77%, 291 mg, 1.3 mmol) was added in small portions to a stirred solution of 2,5-dimethyl-3-(4-methylphenylsulfanyl)-1-benzofuran (322 mg, 1.2 mmol) in dichloromethane (30 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 73%, m.p. 412–413 K; R_f = 0.44 (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 benzene at room temperature.