Crystal Structure of Optically Active Sulfones Based on 4-Aminothiophenol and 5-Menthyloxy- and 5-Bornyloxy-2(5H)-Furanones: Stereochemical Features

D.P.Gerasimova^{a, b,} *, L.V.Frantsuzova^a, A.F.Saifina^a, A.M.Khabibrakhmanova^b, A.M.Khabibullina^b, E.S.Rabbanieva^b, A.R.Kurbangalieva^b, and O.A.Lodochnikova^{a, b}

^aArbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Kazan, Russia

^bButlerov Chemistry Institute, Kazan (Volga region) Federal University, Kazan, Russia

email: *darya.p_gerasimova@mail.ru

Received 15 October, 2024

Abstract— Novel optically active thioethers and sulfones based on 2(5H)-furanone, 4-aminothiophenol, and two monoterpene alcohols l-menthol and l-borneol are synthesized. The crystal structures of two optically active sulfonyl derivatives of the furanone series are studied by single crystal X-ray diffraction (XRD). In both crystals, the compound is presented by independent molecules A and B having radical differences in conformations and hydrogen bond systems. The efficiency of the approach involving a detailed examination of all stereochemical features of a molecule in a crystal is demonstrated based on single crystal XRD data with the use of the Hirshfeld surface analysis.

Keywords: pseudosymmetry, supramolecular associate, intermolecular interactions, Hirshfeld surface, furanones, sulfones.

DOI: 10.1134/S0022476625020131