Synthesis, crystal structure, Hirshfeld Surface analysis, and DFT studies of 16-ferrocenylidene-17β-estra-1,3,5-triene-3,17-diol: Towards the application of ferrocene-hormone conjugates to target hormone dependent breast cancer

Publication date: Available online 15 February 2019Source: Journal of Molecular StructureAuthor(s): José A. Carmona-Negrón, Mariola M. Flores-Rivera, Alberto Santana, Arnold L. Rheingold, Enrique MeléndezAbstractThe ferrocene-hormone conjugate 16-ferrocenylidene-17β-estra-1,3,5-triene-3,17-diol crystallizes in a monoclinic unit cell, space group P21. The asymmetric unit cell contains two ferrocene-hormone conjugates, co-crystallized with two water and one acetonitrile molecules. The crystal structure shows a hydrogen bonding network within the hormone residues and the co-crystallized water and acetonitrile molecules. Hirshfeld surface and two-dimensional fingerprint plots were performed for each of the ferrocene-hormone conjugates in order to analyse weak intermolecular contacts. Particular attention is placed on hydrogen bond interactions in the crystal structure. A noncovalent OH-π intermolecular interaction was found in the crystal structure. DFT studies were employed using the long-range functional ωB97XD and 6–311 g** basis set to study such interactions. The existence of this OH-π intermolecular interaction contributes with −2.32 kcal/mol to the total energy of the crystalline structure.Graphical abstract

Source: Journal of Molecular Structure - February 15, 2019 Category: Molecular Biology Source Type: research