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

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S1600536814007181

. 2014 Apr 5;70(Pt 5):o520. doi: 10.1107/S1600536814007181

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

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

PMCID: PMC4011263 PMID: 24860334

Abstract

In the title compound, C₁₇H₁₅BrO₃S, the dihedral angle between the mean planes of the benzofuran and 4-methylphenyl rings is 76.43 (5)°. In the crystal, molecules are linked via pairs of C—H⋯O hydrogen bonds into inversion dimers that are further linked by Br⋯Br [3.6517 (4) Å] contacts about inversion centers into supramolecular sheets that lie parallel to (111).

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2011 ▶, 2012 ▶, 2013 ▶).

Experimental

Crystal data

C₁₇H₁₅BrO₃S
M _r = 379.26
Triclinic,
a = 8.1554 (2) Å
b = 9.9790 (2) Å
c = 10.1260 (2) Å
α = 77.410 (1)°
β = 77.114 (1)°
γ = 76.009 (1)°
V = 767.68 (3) Å³
Z = 2
Mo Kα radiation
μ = 2.82 mm⁻¹
T = 173 K
0.34 × 0.32 × 0.23 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.543, T _max = 0.746
14016 measured reflections
3812 independent reflections
3336 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.028
wR(F ²) = 0.073
S = 1.04
3812 reflections
202 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.42 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814007181/gg2139sup1.cif

e-70-0o520-sup1.cif^{(19.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814007181/gg2139Isup2.hkl

e-70-0o520-Isup2.hkl^{(186.8KB, hkl)}

Click here for additional data file.^{(5.8KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814007181/gg2139Isup3.cml

CCDC reference: 994776

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2ⁱ	0.95	2.54	3.330 (2)	140

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

1. Comment

As a part of our ongoing study of 5-bromo-2,7-dimethyl-1-benzofuran derivatives containing cyclohexylsulfonyl (Choi et al., 2011), 4-fluorophenylsulfonyl (Choi et al., 2012) and 4-methylphenylsulfinyl (Choi et al., 2013) substituents in the 3-position, we report here on the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran ring system is essentially planar, with a mean deviation of 0.008 (1) Å from the least-squares plane defined by the nine constituent atoms. The 4-methylphenyl ring is essentially planar, with a mean deviation of 0.005 (1) 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 76.43 (5)°. In the crystal structure (Fig. 2), molecules are linked via pairs of C—H···O hydrogen bonds (Table 1) into inversion dimers.

In the crystal, molecules are linked via pairs of C—H···O hydrogen bonds into inversion dimers that are further linked by C—H···O interactions and Br···Br [3.6517 (4) Å] contacts about inversion centers into supramolecular sheets that lie parallel with the (111) plane.

2. Experimental

3-Chloroperoxybenzoic acid (77%, 448 mg, 2.0 mmol) was added in small portions to a stirred solution of 5-bromo-2,7-dimethyl-3-(4-methylphenylsulfanyl)-1-benzofuran (312 mg, 0.9 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 8h, 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 69%, m.p. 474-475 K; R_f = 0.48 (hexane-ethyl acetate, 4:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow vaporation of a solution of the title compound in ethyl acetate at room temperature.