2-Methyl-3-phenyl­sulfonyl-5-propyl-1-benzofuran

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

doi:10.1107/S1600536808025786

. 2008 Aug 16;64(Pt 9):o1761. doi: 10.1107/S1600536808025786

2-Methyl-3-phenylsulfonyl-5-propyl-1-benzofuran

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

PMCID: PMC2960507 PMID: 21201743

Abstract

The title compound, C₁₈H₁₈O₃S, was prepared by the oxidation of 2-methyl-3-phenylsulfanyl-5-propyl-1-benzofuran with 3-chloroperoxybenzoic acid. The phenyl ring makes a dihedral angle of 81.74 (6)° with the plane of the benzofuran fragment. The crystal structure is stabilized by C—H⋯π interactions between a methyl H atom and the phenyl ring of the phenylsulfonyl substituent from a neighbouring molecule, and by intermolecular C—H⋯O interactions.

Related literature

For the crystal structures of similar 2-methyl-3-phenylsulfonyl-1-benzofuran compounds, see: Choi et al. (2008a ▶,b ▶).

Experimental

Crystal data

C₁₈H₁₈O₃S
M _r = 314.38
Monoclinic,
a = 7.2712 (9) Å
b = 17.583 (2) Å
c = 12.788 (2) Å
β = 102.669 (2)°
V = 1595.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 173 (2) K
0.40 × 0.40 × 0.30 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: none
8966 measured reflections
3125 independent reflections
2606 reflections with I > 2σ(I)
R _int = 0.053

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.135
S = 1.12
3125 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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/S1600536808025786/gw2046sup1.cif

e-64-o1761-sup1.cif^{(19.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025786/gw2046Isup2.hkl

e-64-o1761-Isup2.hkl^{(153.4KB, hkl)}

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

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

Cg is the centroid of the C9–C14 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O3ⁱ	0.95	2.60	3.355 (3)	137
C18—H18C⋯Cgⁱⁱ	0.98	3.29	3.947 (4)	126

Open in a new tab

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

supplementary crystallographic information

Comment

This work is related to our communications on the synthesis and structure of 2-methyl-3-phenylsulfonyl-1-benzofuran analogues, viz. 5-ethyl-2-methyl-3-phenylsulfonyl-1-benzofuran (Choi et al., 2008a) and 5-isopropyl-2-methyl-3-phenylsulfonyl-1-benzofuran (Choi et al., 2008b). Here we report the crystal structure of the title compound, 2-methyl-3-phenylsulfonyl-5-propyl-1-benzofuran (Fig. 1).

The benzofuran unit is almost planar, with a mean deviation of 0.018 (2) Å from the least-squares plane defined by the nine constituent atoms. The phenyl ring (C9–C14) makes a dihedral angle of 81.74 (6)° with the plane of the benzofuran fragment. The crystal packing (Fig. 2) is stabilized by intermolecular C—H···π interactions between a methyl H atom and the phenyl ring of the phenylsulfonyl substituent, with a C18—H18C···Cgⁱⁱ separation of 3.291 (4) Å (Fig. 2 and Table 1; Cg is the centroid of the C9–C14 phenyl ring, symmetry code as in Fig. 2). The molecular packing is further stabilized by intermolecular C—H···O interactions (Fig. 2 and Table 1; symmetry code as in Fig. 2).

Experimental

77% 3-Chloroperoxybenzoic acid (471 mg, 2.1 mmol) was added in small portions to a stirred solution of 2-methyl-3-phenylsulfanyl-5-propyl-1-benzofuran (282 mg, 1.0 mmol) in dichloromethane (30 ml) at 273 K. After being stirred for 4 h at room temperature, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by column chromatography (hexane-ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [yield 83%, m.p. 388–389 K; R_f = 0.75 (hexane–ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by evaporation of a solution of the title compound in acetone at room temperature. Spectroscopic analysis: ¹H NMR (CDCl₃, 400 MHz) δ 0.94 (t, J = 7.32 Hz, 3H), 1.62–1.69 (m, 2H), 2,68 (t,J = 7.32 Hz, 2H), 2.79 (s, 3H), 7.12 (d, J = 8.44 Hz, 1H), 7.31 (d, J = 8.44 Hz, 1H), 7.48–7.60 (m, 3H), 7.67 (s, 1H), 8.01 (d, J = 8.44 Hz, 2H); EI-MS 314 [M⁺].