3-Methyl-5-(3-phenoxyphenyl)cyclohex-2-enone

In the title molecule, C19H18O2, the cyclohexene ring adopts an envelope conformation, with all substituents equatorial. The dihedral angle between the benzene and phenyl rings is 83.75 (16)°. No classical hydrogen bonds are found in the crystal structure.


S1. Comment
The present X-ray diffraction study was undertaken to determine how the conformation of the system is affected by the substitution of a methyl group at position 3 and a phenoxyphenyl group at position 5 of the cyclohexenone ring. The molecular structure of the title compound, with atomic numbering scheme, is shown in Fig. 1. The cyclohexene ring adopts an envelope conformation, with all substituents equatorial. The dihedral angle between the benzene and phenyl rings is 83.75 (16)°. No classical hydrogen bonds are found in the crystal structure.

S2. Experimental
The title compound was prepared according to the general procedure reported by Pandiarajan et al. (2005). A mixture of 2,4-bis(ethoxycarbonyl)-5-hydroxy-5-methyl-3,3′-phenoxy phenylcyclohexanone (4.40 g, 0.01 mol) in glacial acetic acid (25 ml) and concentrated hydrochloric acid (50 ml) was refluxed for 12 h. After completion of the reaction, the reaction mixture was neutralized with aqueous ammonia and separated by using chloroform. The product was purified by column chromatography 9.5:0.5 v/v). The yield of the isolated product was 2.08 g (75%).

S3. Refinement
H atoms were positioned geometrically and allowed to ride on their parent atoms, with C-H = 0.95-1.00 Å and U iso (H) = xU eq (carrier atom), where x = 1.5 for methyl and 1.2 for all other C atoms. The maximum residual electron density peak is located 1.08 Å from C5. supporting information sup-2 Acta Cryst. (2008). E64, o1020

Figure 1
The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 40% probability level. Hydrogen atoms are represented by spheres of arbitrary radius.

Data collection
Nonius KappaCCD area-detector diffractometer Radiation source: Nonius FR590 sealed tube generator Horizontally mounted graphite crystal monochromator Detector resolution: 9 pixels mm -1 ω scans with κ offsets 32821 measured reflections 2566 independent reflections 1708 reflections with I > 2σ(I) Special details Experimental. Solvent used: ? Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.560 (2) Frames collected: 270 Seconds exposure per frame: 114 Degrees rotation per frame: 1.2 Crystal-Detector distance (mm): 30.0 Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles 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.