5-Cyclo­hexyl-3-(3-fluoro­phenyl­sulfon­yl)-2-methyl-1-benzofuran

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

doi:10.1107/S1600536811011767

. 2011 Apr 7;67(Pt 5):o1053. doi: 10.1107/S1600536811011767

5-Cyclohexyl-3-(3-fluorophenylsulfonyl)-2-methyl-1-benzofuran

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

PMCID: PMC3089263 PMID: 21754380

Abstract

In the title compound, C₂₁H₂₁FO₃S, the cyclohexyl ring adopts a chair conformation. The 3-fluorophenyl ring makes a dihedral angle of 79.15 (4)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions.

Related literature

For the biological activity of benzofuran compounds, see: Aslam et al. (2009 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For the structure of 5-cyclohexyl-3-(4-fluorophenylsulfonyl)-2-methyl-1-benzofuran, see: Choi et al. 2011 ▶).

Experimental

Crystal data

C₂₁H₂₁FO₃S
M _r = 372.44
Triclinic,
a = 9.0456 (2) Å
b = 10.1996 (2) Å
c = 10.4216 (2) Å
α = 89.915 (1)°
β = 70.461 (1)°
γ = 83.775 (1)°
V = 900.18 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 173 K
0.36 × 0.18 × 0.17 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.603, T _max = 0.666
16115 measured reflections
4143 independent reflections
3650 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.109
S = 1.06
4143 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.53 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/S1600536811011767/mw2005sup1.cif

e-67-o1053-sup1.cif^{(21.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011767/mw2005Isup2.hkl

e-67-o1053-Isup2.hkl^{(203KB, hkl)}

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

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

Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21⋯O3ⁱ	0.95	2.38	3.300 (2)	163
C13—H13A⋯Cg1ⁱⁱ	0.99	2.80	3.638 (2)	143
C19—H19⋯Cg2ⁱⁱⁱ	0.95	2.87	3.660 (2)	141

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

supplementary crystallographic information

Comment

Many compounds possessing a benzofuran ring have attracted much attention due to their interesting pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2009, 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 part of our ongoing program of the substituent effect on the solid state structures of 5-cyclohexyl-3-(4-fluorophenylsulfonyl)-2-methyl-1-benzofuran analogues (Choi et al., 2011), 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 0.005 (1) Å from the least-squares plane defined by the nine constituent atoms. The 3-fluorophenyl ring makes a dihedral angle of 79.15 (4)° with the mean plane of the benzofuran ring. The cyclohexyl ring is in the chair form. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds (Table 1; C21—H21···O3ⁱ). The crystal packing (Fig. 2) is further stabilized by intermolecular C—H···π interactions; the first one between a cyclohexyl H atom and the furan ring (Table 1; C13—H13A···Cg1ⁱⁱ. Cg1 is the centroid of the C1/C2/C7/O1/C8 furan ring), and the second one between a 3-fluorophenyl H atom and the benzene ring (Table 1; C19—H19···Cg2ⁱⁱⁱ. Cg2 is the centroid of the C2–C7 benzene ring).

Experimental

77% 3-chloroperoxybenzoic acid (515 mg, 2.3 mmol) was added in small portions to a stirred solution of 5-cyclohexyl-3-(3-fluorophenylsulfanyl)-2-methyl-1-benzofuran (374 mg, 1.1 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 6h, 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 71%, m.p. 444–445 K; R_f = 0.63 (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 benzene at room temperature.