ao1c06635_si_005.cif (987.63 kB)
9‑Trifluoromethylxanthenediols: Synthesis and Supramolecular Motifs
datasetposted on 2022-04-13, 19:08 authored by Manuel Rodríguez-Molina, Dazaet Galicia-Badillo, Enoc Cetina-Mancilla, Jorge Cárdenas, Lilian I. Olvera, Rubén A. Toscano, Braulio Rodríguez-Molina, Mikhail G. Zolotukhin
The synthesis of four derivatives and the single-crystal X-ray structures of six 9-trifluoromethylxanthenediols (TFXdiols) I–VI are analyzed in this work. These compounds were obtained through superacid-catalyzed condensation of dihydroxybenzenes with 1,1,1-trifluoroacetone or 2,2,2-trifluoroacetophenone. The title molecules have a convex molecular structure due to their three fused rings of the xanthene moiety. We have found that, similar to resorcinol, the configuration of the hydroxyl groups is of great relevance for the crystal packing favoring either interactions above and below their molecular plane or lateral interactions that create layers. Considering that reports of TFXdiols are very scarce, our findings contribute to a better understanding of the molecular conformation and intermolecular interactions in their crystal structures. A similar analysis was extended to a fortuitous cocrystal obtained between 9-trifluoromethyl-9-(4′-fluorophenyl)-xanthenediol and 1,4-dihydroxybenzene, showing that these structures might be used to obtain cocrystals in the future.
three fused ringsvi bfortuitous cocrystal obtained9 ‑ trifluoromethylxanthenediolsxanthene moietytitle moleculessupramolecular motifsstructures mightsix 9ray structuresobtain cocrystalsmolecular planemolecular conformationlateral interactionsintermolecular interactionshydroxyl groupsgreat relevancefour derivativesfindings contributecrystal xcrystal structurescreate layerscatalyzed condensationbetter understanding