5-Bromo-3-ethyl­sulfinyl-2-(4-methyl­phen­yl)-1-benzo­furan

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S1600536814014470

. 2014 Jun 25;70(Pt 7):o808. doi: 10.1107/S1600536814014470

5-Bromo-3-ethylsulfinyl-2-(4-methylphenyl)-1-benzofuran

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

PMCID: PMC4120618 PMID: 25161589

Abstract

In the title compound, C₁₇H₁₅BrO₂S, the dihedral angle between the plane of the benzofuran ring system [r.m.s. deviation = 0.004 (3) Å] and that of the 4-methylphenyl ring is 0.9 (2)°. In the crystal, molecules are linked by C—H⋯O, C—H⋯π and Br⋯π [3.636 (2) Å] interactions, and by π–π interactions between the 4-methylphenyl and furan rings of neighbouring molecules [centroid–centroid distance = 3.650 (2) Å], forming a three-dimensional network.

Keywords: crystal structure

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010 ▶, 2012 ▶). graphic file with name e-70-0o808-scheme1.jpg

Experimental

Crystal data

C₁₇H₁₅BrO₂S
M _r = 363.26
Monoclinic,
a = 5.0202 (3) Å
b = 25.0471 (12) Å
c = 12.2430 (6) Å
β = 100.340 (2)°
V = 1514.45 (14) Å³
Z = 4
Mo Kα radiation
μ = 2.85 mm⁻¹
T = 173 K
0.60 × 0.14 × 0.12 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.541, T _max = 0.746
26373 measured reflections
3868 independent reflections
3104 reflections with I > 2σ(I)
R _int = 0.058

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.139
S = 1.06
3868 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 1.97 e Å⁻³
Δρ_min = −0.83 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 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXS97.

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814014470/ff2130sup1.cif

e-70-0o808-sup1.cif^{(24.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814014470/ff2130Isup2.hkl

e-70-0o808-Isup2.hkl^{(189.6KB, hkl)}

Click here for additional data file.^{(5.5KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814014470/ff2130Isup3.cml

CCDC reference: 1009166

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

Cg1 is the centroid of the C9–C14 4-methylphenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2ⁱ	0.95	2.58	3.507 (4)	164
C16—H16B⋯O2ⁱⁱ	0.99	2.26	3.110 (5)	144
C15—H15C⋯Cg1ⁱⁱ	0.99	2.78	3.607 (3)	143

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

supplementary crystallographic information

S1. Comment

As a part of our ongoing project of 2-aryl-5-bromo-1-benzofuran derivatives containing [3-ethylsulfinyl-2-(4-fluorophenyl)] (Choi et al., 2010) and [2-(4-methylphenyl)-3-methylsulfinyl] (Choi et al., 2012) substituents. We report herein 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 0.004 (3) Å from the least-squares plane defined by the nine constituent atoms. The 4-methylphenyl ring is essentially planar, with a mean deviation of 0.002 (3) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring system and the 4-methylphenyl ring is 0.9 (2)°. In the crystal structure (Fig. 2), molecules are linked by C—H···O and C—H···π hydrogen bonds (Table 1, Cg1 is the centroid of the C9–C14 4-methylphenyl ring) and C4—Br1···π interactions between the bromine atom and the benzene ring of a neighbouring molecule with a Br1···Cg3ⁱⁱⁱ = 3.636 (2) Å (Cg3 is the centroid of the C2–C7 benzene ring). The crystal packing (Fig. 2) also exhibits π···π interactions between the 4-methylphenyl and furan rings of neighbouring molecules, with a Cg1···Cg2ⁱⁱ distance of 3.650 (2) Å (Cg2 is the centroid of the C1/C2/C7/O1/C8 furan ring), forming a three-dimensional network.

S2. Experimental

3-Chloroperoxybenzoic acid (77%, 269 mg, 1.2 mmol) was added in small portions to a stirred solution of 5-bromo-3-ethylsulfanyl-2-(4-methylphenyl)-1-benzofuran (382 mg, 1.1 mmol) in dichloromethane (35 mL) at 273 K. After being stirred at room temperature for 5h, 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 71%, m.p. 404–405 K; R_f = 0.54 (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 benzene at room temperature.