The biologically transformed product of estradiol valerate, namely 3,7α-dihydroxyestra-1,3,5(10)-trien-17-one monohydrate, CHO·HO, has been investigated using UV-Vis, IR, H andC NMR spectroscopic techniques, as well as by mass spectrometric analysis. Its crystal structure was determined using single-crystal X-ray diffraction based on data collected at 100 K. The structure was refined using the independent atom model (IAM) and the transferred electron-density parameters from the ELMAM2 database. The structure is stabilized by a network of hydrogen bonds and van der Waals interactions. The topology of the hydrogen bonds has been analyzed by the Bader theory of `Atoms in Molecules' framework. The molecular electrostatic potential for the transferred multipolar atom model reveals an asymmetric character of the charge distribution across the molecule due to a substantial charge delocalization within the molecule. The molecular dipole moment was also calculated, which shows that the molecule has a strongly polar character.
Key indicators: single-crystal X-ray study; T = 173 K; mean (C-C) = 0.002 Å; disorder in main residue; R factor = 0.037; wR factor = 0.098; data-to-parameter ratio = 14.0.The absolute configuration of the title compound, C 16 H 26 O, was determined as (1R,3S,8R,11R) based mainly on the synthetic pathway but is also implied by the X-ray analysis. The molecule contains fused six-and seven-membered rings. Part of the seven-membered ring was refined as disordered over two sets of sites with the occupancy ratio fixed at 0.86:0.14. The disorder corresponds to a major chair conformation and a minor boat conforation. In the crysyal, O-HÁ Á ÁO hydrogen bonds connect the molecules into chains parallel to the a axis. Table 1 Hydrogen-bond geometry (Å , ).
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ReferencesAgilent (2012). CrysAlis PRO.
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