3β,6α-Diacetoxy-5,9α-dihydroxy-5α-cholest-7-en-11-one

Abstract

The title compound, C31H48O7, a polyoxygenated steroid, was obtained by chemical oxidation of 7-de­hydro­cholesteryl acetate. The mol­ecular geometry features trans A/B and C/D junctions at the steroid core with the acetyl groups in the equatorial position and a fully extended conformation for the alkyl side chain. A chair conformation is observed for rings A and C while ring B adopts a half-chair conformation. The five-membered ring D has an envelope conformation, with the C atom bearing the methyl group at the flap. The terminal isopropyl group and one acetyl group are disordered over two sets of sites with 0.774 (8):0.226 (8) and 0.843 (7):0.157 (7) ratios, respectively. An intra­molecular S(6) O—H⋯O hydrogen-bonding motif involving a hy­droxy donor and acceptor is observed. In the crystal, chains of mol­ecules running along the b axis are formed via O—H⋯O hydrogen bonds between hy­droxy donors and carbonyl acceptors of the ordered acetyl group, giving rise to a C(14) motif. The chains are wrapped around the 21 screw axes.

Crystal structure of an epoxysterol: 9α,11α-epoxy-5α-cholest-7-ene-3β,5,6α-triol 3,6-diacetate

“…We have reported the crystal structure of a steroid closely related to the title compound (Piccialli, Tuzi et al, 2013), in which the two acetyloxy groups, the C18 and C19 methyl groups and the alkyl tail have the same configuration as in the present one, and, moreover, an hydroxy group at C9 and a keto group at C11 are present. In Fig.…”

“…6 the Hirshfeld fingerprint plot of the independent molecule is reported. In the plot, for each Overlay of the X-ray molecular structure of the title compound with the previously reported 3,6-diacetoxy-5,9-dihydroxy-5-cholest-7-en-11one (Piccialli, Tuzi et al, 2013). point of the Hirshfeld surface enveloping the molecule in the crystal, the distance d i to the nearest atom inside the surface and the distance d e to the nearest atom outside the surface are shown.…”