3-(4-Bromo­phenyl­sulfin­yl)-5-chloro-2,7-dimethyl-1-benzo­furan

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S160053681300994X

. 2013 Apr 17;69(Pt 5):o745. doi: 10.1107/S160053681300994X

3-(4-Bromophenylsulfinyl)-5-chloro-2,7-dimethyl-1-benzofuran

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

PMCID: PMC3648275 PMID: 23723895

Abstract

In the title compound, C₁₆H₁₂BrClO₂S, the 4-bromophenyl ring makes a dihedral angle of 88.84 (5)° with the mean plane [r.m.s. deviation = 0.009 (1) Å] of the benzofuran fragment. In the crystal, molecules are linked by weak C—H⋯O and C—S⋯π [3.386 (2) Å] interactions, forming a chain perpendicular to the bc plane.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2012a ▶,b ▶). graphic file with name e-69-0o745-scheme1.jpg

Experimental

Crystal data

C₁₆H₁₂BrClO₂S
M _r = 383.68
Triclinic,
a = 6.1266 (3) Å
b = 10.0247 (5) Å
c = 12.6630 (7) Å
α = 84.749 (3)°
β = 79.235 (2)°
γ = 86.443 (3)°
V = 760.03 (7) Å³
Z = 2
Mo Kα radiation
μ = 3.02 mm⁻¹
T = 173 K
0.33 × 0.23 × 0.16 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.506, T _max = 0.746
13853 measured reflections
3794 independent reflections
3209 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.082
S = 1.05
3794 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.72 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

Click here for additional data file.^{(23.6KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681300994X/aa2089sup1.cif

e-69-0o745-sup1.cif^{(23.6KB, cif)}

Click here for additional data file.^{(186KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681300994X/aa2089Isup2.hkl

e-69-0o745-Isup2.hkl^{(186KB, hkl)}

Click here for additional data file.^{(5.4KB, cml)}

Supplementary material file. DOI: 10.1107/S160053681300994X/aa2089Isup3.cml

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O2ⁱ	0.95	2.50	3.249 (2)	136

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the Blue-Bio Industry Regional Innovation Center (RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan city.

supplementary crystallographic information

Comment

As a part of our continuing study of 5-chloro-2-methyl-1-benzofuran derivatives containing 4-bromophenylsulfonyl (Choi et al., 2012a) and 4-bromophenylsulfinyl (Choi et al., 2012b) substituents in 3-position, 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-bromophenyl ring and the mean plane of the benzofuran ring is 88.84 (5)°. In the crystal structure (Fig. 2), molecules are connected by weak C—H···O hydrogen bonds (Table 1), and by intermolecular C—S···π interactions between the sulfur atom and the 4-bromophenyl ring of an adjacent molecule, with a S1···Cgⁱⁱ being 3.386 (2) Å (Cg is the centroid of the C11/C16 ring).

Experimental

3-Chloroperoxybenzoic acid (77%, 224 mg, 1.0 mmol) was added in small portions to a stirred solution of 3-(4-bromophenylsulfanyl)-5-chloro-2,7-dimethyl-1-benzofuran (331 mg, 0.9 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 5 h, 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 79%, m.p. 442–443 K; R_f = 0.78 (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 ethyl acetate at room temperature.