Syntheses and crystal structures of three salts of sparfloxacin, one incorporating extended tapes of fused pentagonal water assemblies

Holehundi J. Shankara Prasad; Devaraju; Vinaya; Yeriyur B. Basavaraju; Hemmige S. Yathirajan; Sean Parkin; L. Van Meervelt

doi:10.1107/S2056989022011239

Syntheses and crystal structures of three salts of sparfloxacin, one incorporating extended tapes of fused pentagonal water assemblies

Holehundi J. Shankara Prasad, Devaraju, Vinaya, Yeriyur B. Basavaraju, Hemmige S. Yathirajan, Sean Parkin, L. Van Meervelt

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Three organic salts of sparfloxacin, a difluorinated third-generation fluoroquinolone antibiotic, have been synthesized and their crystal structures determined. The salts, sparfloxacinium 4-nitrobenzoate dihydrate, C19H23F2N4O3 +·C7H4NO4 -·2H2O (I), sparfloxacinium 2-phenylacetate, C19H23F2N4O3 +·C8H7O2 - (II), and sparfloxacinium 4-methylbenzoate trihydrate, C19H23F2N4O3 +·C8H7O2 -·3H2O (III), exhibit similar inter-species packing interactions. The overall crystal structures each, however, have their own distinct characteristics, which are described here along with a Hirshfeld surface analysis of the various atom-Atom contacts involving the sparfloxacinium cations. In the crystal structure of III, an extended supramolecular tape of edge-fused hydrogen-bonded water pentagons was found. These pentagonal water and tape motifs are compared to related constructs in a broad selection of structure types, ranging from macromolecules to small molecules, clathrates, and exotic 'ice' formations on clean metal surfaces.

Original language	English
Pages (from-to)	1257-1264
Number of pages	8
Journal	Acta Crystallographica Section E: Crystallographic Communications
Volume	78
DOIs	https://doi.org/10.1107/S2056989022011239
State	Published - Nov 30 2022

Bibliographical note

Publisher Copyright:
© 2022 International Union of Crystallography. All rights reserved.

Funding

One of the authors (HJS) is grateful to the University of Mysore for research facilities. HSY also thanks UGC for a BSR Faculty fellowship for three years.

Funders	Funder number
University Grants Commission

Keywords

crystal structure
hydrogen bonding
sparfloxacin
sparfloxacinium salt
water pentagons
π-π stacking

ASJC Scopus subject areas

General Chemistry
General Materials Science
Condensed Matter Physics

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10.1107/S2056989022011239

Cite this

Shankara Prasad, H. J., Devaraju, Vinaya, Basavaraju, Y. B., Yathirajan, H. S., Parkin, S., & Van Meervelt, L. (2022). Syntheses and crystal structures of three salts of sparfloxacin, one incorporating extended tapes of fused pentagonal water assemblies. Acta Crystallographica Section E: Crystallographic Communications, 78, 1257-1264. https://doi.org/10.1107/S2056989022011239

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abstract = "Three organic salts of sparfloxacin, a difluorinated third-generation fluoroquinolone antibiotic, have been synthesized and their crystal structures determined. The salts, sparfloxacinium 4-nitrobenzoate dihydrate, C19H23F2N4O3 +·C7H4NO4 -·2H2O (I), sparfloxacinium 2-phenylacetate, C19H23F2N4O3 +·C8H7O2 - (II), and sparfloxacinium 4-methylbenzoate trihydrate, C19H23F2N4O3 +·C8H7O2 -·3H2O (III), exhibit similar inter-species packing interactions. The overall crystal structures each, however, have their own distinct characteristics, which are described here along with a Hirshfeld surface analysis of the various atom-Atom contacts involving the sparfloxacinium cations. In the crystal structure of III, an extended supramolecular tape of edge-fused hydrogen-bonded water pentagons was found. These pentagonal water and tape motifs are compared to related constructs in a broad selection of structure types, ranging from macromolecules to small molecules, clathrates, and exotic 'ice' formations on clean metal surfaces.",

keywords = "crystal structure, hydrogen bonding, sparfloxacin, sparfloxacinium salt, water pentagons, π-π stacking",

author = "{Shankara Prasad}, {Holehundi J.} and Devaraju and Vinaya and Basavaraju, {Yeriyur B.} and Yathirajan, {Hemmige S.} and Sean Parkin and {Van Meervelt}, L.",

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Shankara Prasad, HJ, Devaraju, Vinaya, Basavaraju, YB, Yathirajan, HS, Parkin, S & Van Meervelt, L 2022, 'Syntheses and crystal structures of three salts of sparfloxacin, one incorporating extended tapes of fused pentagonal water assemblies', Acta Crystallographica Section E: Crystallographic Communications, vol. 78, pp. 1257-1264. https://doi.org/10.1107/S2056989022011239

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T1 - Syntheses and crystal structures of three salts of sparfloxacin, one incorporating extended tapes of fused pentagonal water assemblies

AU - Shankara Prasad, Holehundi J.

AU - Devaraju,

AU - Vinaya,

AU - Basavaraju, Yeriyur B.

AU - Yathirajan, Hemmige S.

AU - Parkin, Sean

AU - Van Meervelt, L.

PY - 2022/11/30

Y1 - 2022/11/30

N2 - Three organic salts of sparfloxacin, a difluorinated third-generation fluoroquinolone antibiotic, have been synthesized and their crystal structures determined. The salts, sparfloxacinium 4-nitrobenzoate dihydrate, C19H23F2N4O3 +·C7H4NO4 -·2H2O (I), sparfloxacinium 2-phenylacetate, C19H23F2N4O3 +·C8H7O2 - (II), and sparfloxacinium 4-methylbenzoate trihydrate, C19H23F2N4O3 +·C8H7O2 -·3H2O (III), exhibit similar inter-species packing interactions. The overall crystal structures each, however, have their own distinct characteristics, which are described here along with a Hirshfeld surface analysis of the various atom-Atom contacts involving the sparfloxacinium cations. In the crystal structure of III, an extended supramolecular tape of edge-fused hydrogen-bonded water pentagons was found. These pentagonal water and tape motifs are compared to related constructs in a broad selection of structure types, ranging from macromolecules to small molecules, clathrates, and exotic 'ice' formations on clean metal surfaces.

AB - Three organic salts of sparfloxacin, a difluorinated third-generation fluoroquinolone antibiotic, have been synthesized and their crystal structures determined. The salts, sparfloxacinium 4-nitrobenzoate dihydrate, C19H23F2N4O3 +·C7H4NO4 -·2H2O (I), sparfloxacinium 2-phenylacetate, C19H23F2N4O3 +·C8H7O2 - (II), and sparfloxacinium 4-methylbenzoate trihydrate, C19H23F2N4O3 +·C8H7O2 -·3H2O (III), exhibit similar inter-species packing interactions. The overall crystal structures each, however, have their own distinct characteristics, which are described here along with a Hirshfeld surface analysis of the various atom-Atom contacts involving the sparfloxacinium cations. In the crystal structure of III, an extended supramolecular tape of edge-fused hydrogen-bonded water pentagons was found. These pentagonal water and tape motifs are compared to related constructs in a broad selection of structure types, ranging from macromolecules to small molecules, clathrates, and exotic 'ice' formations on clean metal surfaces.

KW - crystal structure

KW - hydrogen bonding

KW - sparfloxacin

KW - sparfloxacinium salt

KW - water pentagons

KW - π-π stacking

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JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

ER -

Syntheses and crystal structures of three salts of sparfloxacin, one incorporating extended tapes of fused pentagonal water assemblies

Abstract

Bibliographical note

Funding

Keywords

ASJC Scopus subject areas

Access to Document

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