Anomeric effect and hydrogen-bonded supramolecular motif in 5-(3-fluoro-4-methoxyphenyl)-1-[(3-fluoro-4-methoxyphenyl)aminomethyl]-1,3,5-triazinane-2-thione.

In the title compound, C(18)H(20)F(2)N(4)O(2)S, the triazinane-2-thione ring adopts an envelope conformation, the ring substituents lie on the same side of the mean plane of the heterocyclic ring and the exo lp-N-C-N(triaz) unit (lp is a lone pair and triaz is the triazinane ring) exhibits an antiperiplanar orientation, which is shown to be governed by strong anomeric effects. Molecules are linked into a complex three-dimensional framework by a combination of two N-H...S hydrogen bonds, three C-H...F hydrogen bonds and a pi-pi stacking interaction.