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Stable and reproducible supramolecular motif in the crystal structure of sulfonamides of the benzothiazine series fused to an epoxybornane moiety

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Abstract

The crystal structures of four sulfonamides of the benzothiazine series, fused to an epoxidized norbornane moiety and containing various substituents in the para position of the aromatic ring, were determined. Despite the different volume and acceptor/donor properties of substituents (hydrogen, a methyl group, a cyano group, fluorine), these compounds form isostructural crystals. The main supramolecular motif of these crystals consists of heterochiral chains, which run along a glide plane and are formed via hydrogen bonds between the axial oxygen atom of the sulfonyl group and the amino-group nitrogen atom. The chains are cross-linked to form a crystal structure through C—H…O interactions between the hydrogen atom at the epoxide ring and the equatorial sulfonyl oxygen atom.

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Authors and Affiliations

  1. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of the Russian Academy of Sciences, 8 ul. Akad. Arbuzova, 420088, Kazan, Russian Federation

    O. A. Lodochnikova, E. A. Akhmetshina & I. A. Litvinov

  2. A. M. Butlerov Chemical Institute, Kazan Federal University, 18 ul. Kremlevskaya, 420008, Kazan, Russian Federation

    O. A. Lodochnikova & V. V. Plemenkov

  3. Kazan State Medical University, 49 ul. Butlerova, 420012, Kazan, Russian Federation

    E. R. Mingaleva, V. A. Startseva & L. E. Nikitina

Authors
  1. O. A. Lodochnikova
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  2. E. A. Akhmetshina
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  3. E. R. Mingaleva
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  4. V. A. Startseva
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  5. I. A. Litvinov
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  6. V. V. Plemenkov
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  7. L. E. Nikitina
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Corresponding author

Correspondence to O. A. Lodochnikova.

Additional information

This study was financially supported by the Russian Science Foundation (Project No. 17-13-01209). The synthesis of the key compounds was in part financially supported by the Ministry of Science and Higher Education of the Russian Federation (within the framework of the Government program “5–100 Russian Academic Excellence Project” aimed to improve the competitiveness of the Kazan (Volga region) Federal University among world.s leading research and education centers).

Based on the materials of the International Markovnikov Congress on Organic Chemistry (June 21—28, 2019, Moscow—Kazan, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 0313—0319, February, 2020.

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Lodochnikova, O.A., Akhmetshina, E.A., Mingaleva, E.R. et al. Stable and reproducible supramolecular motif in the crystal structure of sulfonamides of the benzothiazine series fused to an epoxybornane moiety. Russ Chem Bull 69, 313–319 (2020). https://doi.org/10.1007/s11172-020-2762-2

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  • DOI: https://doi.org/10.1007/s11172-020-2762-2

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