Five fluorinated diphenidine derivatives were synthesized and their structures determined using NMR spectroscopy and X-ray crystallography. All five compounds form hydrogen bonds between their quaternary amine hydrogen atoms and chloride ions. Two compounds show N-H⋯Cl distances of 2.21–2.31 Å, while three exhibit shorter distances of 2.07–2.20 Å. The compound with a pyrrolidine ring adopts an envelope conformation, and the one with a piperidine ring adopts a chair conformation. Crystal packing in all five structures involves C-H⋯π interactions, and no π-π interactions are observed.
Psilocin, the primary metabolite of the psychedelic compound psilocybin, crystallizes in two anhydrous polymorphic forms (I and II). Form I, first reported in 1974, was redetermined to modern standards, and its variable-temperature unit-cell parameters were measured. Form II, described for the first time, crystallizes in space group P21/n and exhibits a different molecular conformation: the N,N-dimethylethylene substituent is gauche, allowing the molecule to form a strong intramolecular O–H⋯N hydrogen bond. In Form II, molecules also form one-dimensional strands via N–H⋯O hydrogen bonds, and the structure shows whole-molecule disorder with an occupancy ratio of 0.689:0.311. Form I lacks intramolecular hydrogen bonds and instead forms a layered structure through intermolecular N–H⋯O and O–H⋯N hydrogen bonds.