5-Cyclo­hexyl-3-(4-fluoro­phenyl­sulfin­yl)-2-methyl-1-benzofuran

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

doi:10.1107/S1600536811007112

. 2011 Mar 2;67(Pt 4):o768. doi: 10.1107/S1600536811007112

5-Cyclohexyl-3-(4-fluorophenylsulfinyl)-2-methyl-1-benzofuran

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

PMCID: PMC3099981 PMID: 21754062

Abstract

In the title compound, C₂₁H₂₁FO₂S, the cyclohexyl ring adopts a chair conformation. The 4-fluorophenyl ring makes a dihedral angle of 83.55 (4)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked through weak intermolecular C—H⋯O and C—H⋯π interactions. The crystal structure also exhibits aromatic π–π interactions between the furan rings of neighbouring molecules [centroid–centroid distance = 3.541 (2) 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 related 3-(4-fluorophenylsulfinyl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010a ▶,b ▶,c ▶).

Experimental

Crystal data

C₂₁H₂₁FO₂S
M _r = 356.44
Triclinic,
a = 9.2531 (2) Å
b = 10.1934 (2) Å
c = 10.8151 (2) Å
α = 81.127 (1)°
β = 66.716 (1)°
γ = 72.248 (1)°
V = 891.73 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 173 K
0.29 × 0.23 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.943, T _max = 0.964
15790 measured reflections
4073 independent reflections
3436 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.111
S = 1.04
4073 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.27 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/S1600536811007112/zq2090sup1.cif

e-67-0o768-sup1.cif^{(21.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007112/zq2090Isup2.hkl

e-67-0o768-Isup2.hkl^{(199.6KB, hkl)}

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

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

Cg1 is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯O1ⁱ	0.95	2.48	3.283 (2)	142
C21—H21⋯O2ⁱⁱ	0.95	2.37	3.213 (2)	148
C10—H10B⋯Cg1ⁱⁱⁱ	0.99	2.86	3.624 (2)	135
C15—H15C⋯Cg1^iv	0.98	2.93	3.510 (2)	119

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

supplementary crystallographic information

Comment

Many compounds having a benzofuran skeleton have attracted much attention owing to their interesting pharmacological properties such as antifungal, antitumor and antiviral, antimicrobial activities (Aslam et al., 2006, Galal et al., 2009, Khan et al., 2005). These compounds widely occur in nature (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our study of the substituent effect on the solid state structures of 3-(4-fluorophenylsulfinyl)-2-methyl-1-benzofuran analogues (Choi et al., 2010a,b,c), we report here 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 0.004 (1) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring is in the chair form. The dihedral angle formed by the mean plane of the benzofuran ring and the 4-fluorophenyl ring is 83.55 (4)°. The molecular packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds; the first one between a 4-fluorophenyl H atom and the furan O atom (Table 1; C20—H20···O1ⁱ), and the second one between a 4-fluorophenyl H atom and the oxygen of the S═O unit (Table 1; C21-H21···O2ⁱⁱ). The molecular packing (Fig. 3) is further stabilized by intermolecular C—H···π interactions; the first one between a cyclohexyl H atom and the benzene ring (Table 1; C10—H10B···Cg1ⁱⁱⁱ), and the second one between a methyl H atom and the benzene ring (Table 1; C15—H15C···Cg1^iv, Cg1 is the centroid of the C2–C7 benzene ring). The molecular packing (Fig. 3) also exhibits aromatic π–π interactions between the furan rings of neighbouring molecules, with a Cg2···Cg2^iv distance of 3.541 (2) ° (Cg2 is the centroid of the C1/C2/C7/O1/C8 furan ring).

Experimental

77% 3-chloroperoxybenzoic acid (224 mg, 1.0 mmol) was added in small portions to a stirred solution of 5-cyclohexyl-3-(4-fluorophenylsulfanyl)-2-methyl-1-benzofuran (306 mg, 0.9 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 4h, 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 74%, m.p. 422–423 K; R_f = 0.59 (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.