(4-Methoxyphenyl)(4-propylcyclohexyl)methanone

The asymmetric unit of the title compound, C17H24O2, contains two independent molecules with different conformations. The least-squares plane through the cyclohexane ring makes dihedral angles of 52.9 (5) and 81.4 (4)° with the benzene ring in the two molecules. The cyclohexane ring adopts a chair conformation in both molecules. In the crystal, weak C—H⋯O hydrogen bonds link molecules related by translation in [100] into two crystallographically independent chains.

The asymmetric unit of the title compound, C 17 H 24 O 2 , contains two independent molecules with different conformations. The least-squares plane through the cyclohexane ring makes dihedral angles of 52.9 (5) and 81.4 (4) with the benzene ring in the two molecules. The cyclohexane ring adopts a chair conformation in both molecules. In the crystal, weak C-HÁ Á ÁO hydrogen bonds link molecules related by translation in [100] into two crystallographically independent chains.   Table 1 Hydrogen-bond geometry (Å , ). supplementary materials . E69, o404 [doi:10.1107/S1600536813003644] (4-Methoxyphenyl)(4-propylcyclohexyl)methanone Ling Wang, Zi-Qian Chang, Jie Zhang and Cheng-Min Li Comment SGLT2 inhibitors constitute new class of hyperglycemic agents, and the most advanced drug dapagliflozin has been approved recently in EU for the treatment of type 2 diabetes (Washburn, 2009). The title compound has been obtained in our laboratory as an intermediate used in the synthesis of SGLT2 inhibitors (Zhao et al., 2011;Shao et al., 2011).

Related literature
The asymmetric unit of the title compound, C 17 H 24 O 2 , contains two independent molecules differing in conformations.
In one independent molecule, the mean planes of C27/C28/C30/C31 and benzene ring C19-C24 form a dihedral angle of 52.9 (5)°, while in another independent molecule, the mean planes of C10/C11/C13/C14 and benzene ring C2-C7 form a dihedral angle of 81.4 (4)°. The cyclohexane ring adopts a chair conformation in both molecules. All bond lengths are normal and correspond to those observed in the related compound (Wang et al., 2011).
In the crystal, weak intermolecular C-H···O hydrogen bonds (Table 1)

link the molecules related by translation in
[100] into two crystallographically independent chains.

Experimental
17.03 g (0.1 mol) of trans-4-propylcyclohexanecarboxylic acid was stirred in 150 ml of dried dichloromethane at room temperature, followed by dropwise addition of 17.80 g (0.13 mol) of freshly distilled oxalyl chloride and 0.1 ml of dried DMF. The resulting mixture was stirred at room temperature for 5 h and evaporated in vacuo to remove the solvent and excessive oxalyl chloride to give a residue, which was dissolved in 100 ml of dried dichloromethane followed by addition of 10.81 g (0.1 mol) of anisole. The mixture thus obtained was stirred at 10 centigrade followed by addition of 14.67 g (0.11 mol) of AlCl 3 portionwise. The reaction mixture was then stirred at room temperature overnight, poured into 300 ml of ice-water and extracted with 100 ml, three times of dichloromethane. The combined extracts were washed with brine, dried over Na2SO4 and evaporated to dryness. The residue was purified by column chromatography to afford the pure title compound as colorless crystals. The single crystals suitable for single-crystal X-ray diffraction were obtained by slow evaporation at room temperature of a 0.2 M solution of the title compound in dichloromethane/hexane (1/15).

Refinement
All H atoms were geometrically positioned (C-H = 0.95-1.00 Å) , and included in the final cycles of refinement using a riding model, with U iso (H) = 1.2-1.5 U eq (C).  Two independent molecules of the title compound showing the atomic numbering and 40% probability displacement ellipsoids.

(4-Methoxyphenyl)(4-propylcyclohexyl)methanone
Crystal data (1)  Special details Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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.