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Synthesis and crystal structure of a meloxicam co-crystal with benzoic acid

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Abstract

Single crystals of a 1:1 co-crystal of meloxicam [4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-2H-1λ6,2-benzothiazine-3-carboxamide], MXM, with benzoic acid, BZA, were crystalized from a THF solution. The same MXM-BZA co-crystal has been obtained as a fine powder by liquid-assisted co-grinding using as fluid additives solvents with different polarity: benzene, toluene, ortho-xylene, meta-xylene, para-xylene, THF, and water. The latter is especially eco-friendly and can be a good candidate for industrial production. The crystal structures of all the MXM co-crystals deposited in the most recent version of the Cambridge Database were compared, in order to correlate the non-covalent interactions in these structures with the сonclusions from the theoretical analysis of solubility carried out by Cysewski (J. Mol. Model 24:112, 2018).

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Notes

  1. A topocentroid is a topological index that is calculated for a group of 5-atoms as proposed by Cremer et al. [25] and 6-atoms as proposed by Boeyens et al. [26].

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Acknowledgments

The authors received funding from the Russian Ministry of Science and Higher Education.

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Authors and Affiliations

  1. SkolTech Skolkovo Institute of Science and Technology, ul. Nobelya 3, Moscow, Russian Federation, 121205

    Christian Tantardini

  2. Novosibirsk State University, ul. Pirogova 2, Novosibirsk, Russian Federation, 630090

    Christian Tantardini, Sergey G. Arkipov, Kseniya A. Cherkashina, Alexander S. Kil’met’ev & Elena V. Boldyreva

  3. Institute of Solid State Chemistry and Mechanochemistry SB RAS, ul. Kutateladze 18, Novosibirsk, Russian Federation, 630128

    Sergey G. Arkipov

  4. Novosibirsk Institute of Organic Chemistry SB RAS, Lavrentiev Ave. 9, Novosibirsk, Russian Federation, 630090

    Alexander S. Kil’met’ev

  5. Boreskov Institute of Catalysis SB RAS, Laverentiev Ave. 5, Novosibirsk, Russian Federation, 630090

    Elena V. Boldyreva

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  1. Christian Tantardini
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  2. Sergey G. Arkipov
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  3. Kseniya A. Cherkashina
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  4. Alexander S. Kil’met’ev
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  5. Elena V. Boldyreva
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Correspondence to Christian Tantardini, Sergey G. Arkipov or Elena V. Boldyreva.

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Tantardini, C., Arkipov, S.G., Cherkashina, K.A. et al. Synthesis and crystal structure of a meloxicam co-crystal with benzoic acid. Struct Chem 29, 1867–1874 (2018). https://doi.org/10.1007/s11224-018-1166-5

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  • DOI: https://doi.org/10.1007/s11224-018-1166-5

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