Received 11 April 2011
Three independent molecules of the title estrone derivative and a molecule of methanol comprise the asymmetric unit of the title compound [systematic name: 13-methyl-6,7,8,9,11,12,13,14,15,16-decahydrocyclopenta[a]phenanthren-3-ol-methanol (3/1)], 3C18H24O·CH3OH. Two of the estrone molecules exhibit 50:50 disorder (one displays whole-molecule disorder and the other partial disorder in the fused five- and six-membered rings) so that five (partial) molecular conformations are discernable. The conformation of the six-membered ring abutting the aromatic ring is close to a half-chair in all five components. The conformation of the six-membered ring fused to the five-membered ring is based on a chair with varying degrees of distortion ranging from minor to significant. Two distinct conformations are found for the five-membered ring: in four molecules, the five-membered ring is twisted about the bond linking it to the six-membered ring, and in the other, the five-membered ring is an envelope with the quaternary C atom being the flap atom. The crystal packing features O-HO hydrogen bonding whereby the four molecules comprising the asymmetric unit are linked into a supramolecular chain along the b axis.
For the original synthesis, see: Huang-Minlon (1949). For geometric and structural features for a series of cholestane derivatives, see: Rajnikant et al. (2006). For background to steroidal estrogen boronic acids and boronates, see: Ketuly & Hadi (2010). For related structures see: Ketuly et al. (1997, 2010).
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and QMOL (Gans & Shalloway, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5844 ).
The authors thank the University of Malaya for support and greatly appreciate UMRG grant No. RG035/10BIO.
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