3-(4-Bromo­phenyl­sulfon­yl)-5-chloro-2-methyl-1-benzofuran

Hong Dae Choi; Pil Ja Seo; Uk Lee

doi:10.1107/S1600536812024592

. 2012 Jun 13;68(Pt 7):o2027. doi: 10.1107/S1600536812024592

3-(4-Bromophenylsulfonyl)-5-chloro-2-methyl-1-benzofuran

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

PMCID: PMC3393296 PMID: 22807853

Abstract

In the title compound, C₁₅H₁₀BrClO₃S, the 4-bromo-substituted benzene ring forms a dihedral angle of 72.55 (6)° with the mean plane [mean deviation = 0.008 (2) Å] of the benzofuran ring system. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds into chains along [001]. There are also π–π interactions between the furan and benzene rings of symmetry-related benzofuran systems [centroid–centroid distances = 3.549 (3) and 3.632 (3) Å].

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2008 ▶, 2010 ▶).

Experimental

Crystal data

C₁₅H₁₀BrClO₃S
M _r = 385.65
Triclinic,
a = 7.1089 (2) Å
b = 10.4169 (3) Å
c = 11.0217 (3) Å
α = 69.659 (2)°
β = 89.526 (2)°
γ = 71.632 (1)°
V = 721.58 (4) Å³
Z = 2
Mo Kα radiation
μ = 3.18 mm⁻¹
T = 173 K
0.38 × 0.31 × 0.27 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.448, T _max = 0.746
13182 measured reflections
3570 independent reflections
3007 reflections with I > 2σ(I)
R _int = 0.054

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.097
S = 1.08
3570 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.43 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 (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/S1600536812024592/lh5482sup1.cif

e-68-o2027-sup1.cif^{(23.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812024592/lh5482Isup2.hkl

e-68-o2027-Isup2.hkl^{(175KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812024592/lh5482Isup3.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
C11—H11⋯O2ⁱ	0.95	2.53	3.203 (3)	128
C15—H15⋯O3ⁱⁱ	0.95	2.57	3.195 (3)	124

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

supplementary crystallographic information

Comment

As a part of our ongoing study of 5-chloro-2-methyl-1-benzofuran derivatives containing 3-phenylsulfonyl (Choi et al., 2008) and 3-(4-fluorophenylsulfonyl) (Choi et al., 2010) 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 0.008 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 4-bromo substituted benzene ring and the mean plane of the benzofuran fragment is 72.55 (6)°. In the crystal structure (Fig. 2), molecules are connected by weak C—H···O hydrogen bonds (Table 1). The crystal packing (Fig. 3) also exhibits offset π–π interactions between the furan and benzene rings of neighbouring molecules, with Cg1···Cg2ⁱⁱⁱ & Cg1···Cg2^iv distances of 3.549 (3) Å & 3.632 (3) Å [Symmetry codes: (iii) - x + 1,- y + 1,- z + 1; (iv) - x, - y + 1,- z + 1] and interplanar distances of 3.510 (3) Å & 3.343 (3) Å resulting in slippages of 0.511 (3) Å & 1.420 (3) Å (Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively).

Experimental

3-Chloroperoxybenzoic acid (77%, 381 mg, 1.7 mmol) was added in small portions to a stirred solution of 3-(4-bromophenylsulfanyl)-5-chloro-2-methyl-1-benzofuran (318 mg, 0.8 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 (benzene) to afford the title compound as a colorless solid [yield 76%, m.p. 454-456 K; R_f = 0.71 (benzene)]. 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.