Crystal structure of (3R,6R,Z)-3-Hydroxy-3,6-dimethyl-2-(3- methylbutylidene)hexahydrobenzofuran-4(2H)-one, C15H24O3

Abstract

Source of materialThebisabolangelone (0.26g,1.0 mmol)and Pd/C (0.05g,10% w/w)was dissolvedinEtOH(20 ml)at25°Cunder dry nitrogen atmosphere, then hydrogen gas (99%) was bubbled into the vigorous stirred solution (300 ml/minute) for 2.0 hu ntil the bisabolangelone was completely consumed. Filtration of the catalyst and removing the solvents at reduced pressure give white solids, which was purified by columnchromatography on silica with ethylacetate/petroleum ether (1:3) as eluent to give four pure target compound as colourless needles (0.21 g). X-ray quality crystals were obtained by the vapor diffusion of diethyl ether into a solution of the target compound in EtOAc at room temperature, and the colourless orthorhombic crystal with dimensions of 0.23´0.18´0.16 mm wasselectedfor measurement. Diffraction data of the single-crystal were collected at 296(2) KonaRigaku Mecury CCDd iffractometere quippedw ithag raphite-monochromatic Mo Ka (l =0.71073 Å) by Crystal clear software. Atotal of 2766 reflections were collected in the range of 2.74°£ q £ 25.01°by using an w-scan mode, of which 6799 were unique with R int =0.0659 and 2198 were observed with I>2s(I).Empirical absorption corrections were applied. The structures were solved by direct methods using SHELX programs [11]. All of the nonhydrogen atomswere located from the difference Fourier maps, and then refined anisotropically with SHELXL97 via afull-matrix least-square procedure [11].The hydrogen atomswere added according to the theoretically model. Experimental detailsThe positionsofall Hatoms were determined geometrically and refinedu sing ar idingm odel with C-H =0 .93-0.97 Åa nd U iso (methyl H) =1.5 U eq (C) and 1.2 U eq for other Hatoms.