Doxycycline hydrate and doxycycline hydrochloride dihydrate – crystal structure and charge density analysis.
In: Zeitschrift für Kristallographie. Crystalline Materials, Jg. 233 (2018-09-01), Heft 9/10, S. 649-661
academicJournal
Zugriff:
High-resolution low-temperature X-ray diffraction experiments for doxycycline monohydrate and hydrochloride dihydrate have been performed. Translation-Libration-Screw (TLS) analysis for both crystal forms as well as the data from neutron diffraction experiment for hydrochloride combined with the Hansen-Coppens formalism resulted in precise charge density distribution models for both the zwitterionic monohydrate and a protonated hydrochloride crystal forms. Their detailed topological analysis suggested that the electron structure of doxycycline's amide moiety undergoes significant changes during protonation due to formation of a very strong resonance-assisted hydrogen bond. A notably increased participation of amide nitrogen atom and hydrogen-accepting oxygen atom in the resonance upon doxycycline protonation was observed. A comparison of TLS- and neutron data-derived hydrogen parameters confirmed the experimental neutron data to be vital for proper description of intra- and inter-molecular interactions in this compound. Finally, calculated lattice and interaction energies quantified repulsive Dox-Dox interactions in the protonated crystal form of the antibiotic, relating with a good solubility of doxycycline hydrochloride relative to its hydrate. [ABSTRACT FROM AUTHOR]
Titel: |
Doxycycline hydrate and doxycycline hydrochloride dihydrate – crystal structure and charge density analysis.
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Autor/in / Beteiligte Person: | Tchoń, Daniel ; Makal, Anna ; Gutmann, Matthias ; Woźniak, Krzysztof |
Zeitschrift: | Zeitschrift für Kristallographie. Crystalline Materials, Jg. 233 (2018-09-01), Heft 9/10, S. 649-661 |
Veröffentlichung: | 2018 |
Medientyp: | academicJournal |
ISSN: | 2194-4946 (print) |
DOI: | 10.1515/zkri-2018-2058 |
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