5-Bromo-3-cyclo­hexyl­sulfinyl-2,7-dimethyl-1-benzofuran

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

doi:10.1107/S1600536811011354

. 2011 Apr 7;67(Pt 5):o1039. doi: 10.1107/S1600536811011354

5-Bromo-3-cyclohexylsulfinyl-2,7-dimethyl-1-benzofuran

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

PMCID: PMC3089368 PMID: 21754366

Abstract

In the title compound, C₁₆H₁₉BrO₂S, the cyclohexyl ring adopts a chair conformation. In the crystal, molecules are linked by a Br⋯Br [3.5994 (5) Å] contact and a C—H⋯π interaction involving the phenyl ring of the benzofuran. The crystal structure also exhibits a slipped π–π interaction between the furan rings of neighbouring molecules [centroid–centroid distance = 3.767 (1) Å and interplanar distance of 3.452 (1) Å with a slippage of 1.508 Å].

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For structural studies of the related 5-bromo-3-cyclohexylsulfinyl-2-methyl-1-benzofuran, see: Choi et al. (2011 ▶).

Experimental

Crystal data

C₁₆H₁₉BrO₂S
M _r = 355.28
Triclinic,
a = 6.3957 (2) Å
b = 11.2576 (3) Å
c = 12.0384 (3) Å
α = 104.726 (2)°
β = 101.426 (1)°
γ = 106.380 (1)°
V = 769.53 (4) Å³
Z = 2
Mo Kα radiation
μ = 2.81 mm⁻¹
T = 173 K
0.19 × 0.17 × 0.09 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.660, T _max = 0.746
14554 measured reflections
3887 independent reflections
3165 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.030
wR(F ²) = 0.077
S = 1.03
3887 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.30 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 datablocks global, I. DOI: 10.1107/S1600536811011354/dn2669sup1.cif

e-67-o1039-sup1.cif^{(19.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011354/dn2669Isup2.hkl

e-67-o1039-Isup2.hkl^{(190.5KB, hkl)}

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

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

Cg1 is the centroid of the phenyl ring of the benzofuran.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯Cg1ⁱ	0.98	2.97	3.717 (2)	134

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Many compounds having a benzofuran skeleton have attracted interesting pharmacological properties such as antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2006, Galal et al., 2009, Khan et al., 2005). These compounds occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing study of the substituent effect on the solid state structures of 3-cyclohexylsulfinyl-5-halo-2-methyl-1-benzofuran analogues (Choi et al., 2011), 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 0.010 (1) Å from the least-squares plane defined by the nine constituent atoms. The crystal packing (Fig. 2) is stabilized by an intermolecular Br1···Br1ⁱ contact at 3.5994 (5) Å, and by a weak intermolecular C—H···π interaction (Table 1, Cg1 is the centroid of the C2–C7 phenyl ring of the benzofuran). The crystal packing (Fig. 2) is further stabilized by a weak slippest π···π interaction between the furan rings of neighbouring molecules, with a Cg2···Cg2ⁱⁱ distance of 3.767 (1) Å and an interplanar distance of 3.452 (1) Å resulting in a slippage of 1.508 Å (Cg2 is the centroid of the C1/C2/C7/O1/C8 furan ring).

Experimental

77% 3-chloroperoxybenzoic acid (269 mg, 1.2 mmol) was added in small portions to a stirred solution of 5-bromo-3-cyclohexylsulfanyl-2,7-dimethyl-1-benzofuran (373 mg, 1.1 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 3h, 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 75%, m.p. 415–416 K; R_f = 0.61 (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 acetone at room temperature.