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Two Crystal Structures of Benzo-1,2-Thiazine-S,S-Dioxide with a Condensed Norbornane Fragment Differing in the Configuration of the Nitrogen Atom in the Molecule

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Abstract

Configuration lability of the nitrogen atom in the –N(H)–SO2– group of the cyclic sulfonamide molecule determines the existence of two different diastereomeric forms (individual and crystal solvate ones) occurring in the corresponding crystals. Molecular structures of the diastereomeric forms in crystals and in the gas phase are studied using quantum chemical calculations. It is established that the inversion of the nitrogen configuration leads to the electron density redistribution and to some geometry shifts in the heteroatom-bearing key fragment of the molecule.

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Funding

The XRD experiment and the quantum chemical calculations were funded by the Russian Science Foundation (project No. 22-13-00284) at the Distributed Spectral-Analytical Center of Shared Facilities for the Study of Structure, Composition and Properties of Substances and Materials of FRC Kazan Scientific Center of RAS. The synthesis of the key compound was partially funded by the Priority 2030 Strategic Leadership Program of KFU.

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Authors and Affiliations

  1. Arbuzov Institute of Organic and Physical Chemistry, Subdivision of the Federal State Budgetary Institution of Science “Kazan Scientific Center of Russian Academy of Sciences”, Kazan, Russia

    D. P. Gerasimova & O. A. Lodochnikova

  2. Kant Baltic Federal University, Kaliningrad, Russia

    Y. V. Veremeichik

  3. Kazan (Volga region) Federal University, Butlerov Institute of Chemistry, Kazan, Russia

    O. A. Lodochnikova

Authors
  1. D. P. Gerasimova
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  2. Y. V. Veremeichik
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  3. O. A. Lodochnikova
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Correspondence to O. A. Lodochnikova.

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Russian Text © The Author(s), 2023, published in Zhurnal Strukturnoi Khimii, 2023, Vol. 64, No. 8, 114890.https://doi.org/10.26902/JSC_id114890

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Gerasimova, D.P., Veremeichik, Y.V. & Lodochnikova, O.A. Two Crystal Structures of Benzo-1,2-Thiazine-S,S-Dioxide with a Condensed Norbornane Fragment Differing in the Configuration of the Nitrogen Atom in the Molecule. J Struct Chem 64, 1504–1512 (2023). https://doi.org/10.1134/S0022476623080140

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