Ethyl 2-(5-cyclohexyl-3-methylsulfinyl-1-benzofuran-2-yl)acetate

In the title compound, C19H24O4S, the cyclohexyl ring adopts a chair conformation. In the crystal, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds. The O atom of the sulfinyl group is disordered over two orientations with site-occupancy factors of 0.875 (4) and 0.125 (4).


D-HÁ
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2187).
, 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 a part of our ongoing study of the substituent effect on the solid state structures of ethyl 2-(3-methylsulfinyl-1-benzofuran-2-yl)acetate analogues (Choi et al., 2007a,b;2009), 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 0.011 (2) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring is in the chair form. The O atom of sulfinyl group is disordered over two positions with site-occupancy factors, from refinement of 0.875 (3) (part A) and 0.125 (4) (part B). The molecular packing (Fig. 2) is stabilized by weak intermolecular C-H···O hydrogen bonds; the first one between a cyclohexyl H atom and the O atom of the sulfinyl group (Table 1; C14-H14B···O4A i ), and the second one between an H atom of the benzylic methylene group and the O atom of the carbonyl group (Table 1; C15-H15B···O2 ii ).

Experimental
77% 3-chloroperoxybenzoic acid (224 mg, 1.0 mmol) was added in small portions to a stirred solution of ethyl 2-(5-cyclohexyl-3-methylsulfanyl-1-benzofuran-2-yl)acetate (298 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, 1:2 v/v) to afford the title compound as a colorless solid [yield 70%, m.p. 360-361 K; R f = 0.41 (hexane-ethyl acetate, 1:2 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.

Refinement
All H atoms were positioned geometrically and refined using a riding model, with C-H = 0.95 Å for aryl, 1.00 Å for methine, 0.99 Å for methylene and 0.98 Å for methyl H atoms, respectively. U iso (H) = 1.2U eq (C) for aryl, methine, methylene, and 1.5U eq (C) for methyl H atoms. The O atom of sulfinyl group is disordered over two positions with site-ccupancy factors, from refinement of 0.875 (4) (part A) and 0.125 (4) (part B). The S-O distances were restrained to 0.001 Å using command SADI and DELU.
supplementary materials sup-2 Figures Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius. The O atom of sulfinyl group is disordered over two positions with site-occupancy factors, from refinement of 0.875 (3) (part A) and 0.125 (4) (part B).

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2sigma(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.