Intermolecular interactions, disorder and twinning in ciprofloxacin-2,2-difluoroethanol (2/3) and ciprofloxacin-water (3/14.5)

Francesca P A Fabbiani, Jean Baptiste Arlin, Gernot Buth, Birger Dittrich, Alastair J Florence, Regine Herbst-Irmer, Heidrun Sowa

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

The antibiotic ciprofloxacin [systematic name: 1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-4-ium-1-yl)-1,4-dihydroquinoline-3-carboxylate], has been crystallized as a 2:3 solvate with 2,2-difluoroethanol, 2C(17)H(18)FN(3)O(3)·3C(2)H(4)O(2), (I), and as a 3:14.5 hydrate, 3C(17)H(18)FN(3)O(3)·14.5H(2)O, (II). The structure of (I) was determined using synchrotron X-ray diffraction data and refined as a two-component nonmerohedral twin. Both structures contain several independent molecules in the asymmetric unit: (I) contains two zwitterionic ciprofloxacin molecules and three difluoroethanol solvent molecules, while (II) contains three zwitterionic ciprofloxacin molecules and a mixture of ordered and disordered water molecules. The intermolecular interactions were analysed using fingerprint plots derived from Hirshfeld surfaces, providing a detailed description of the unique environment of each independent ciprofloxacin molecule.
LanguageEnglish
Pageso120-o124
Number of pages5
JournalActa Crystallographica Section C: Crystal Structure Communications
Volume67
Issue number3
DOIs
Publication statusPublished - Mar 2011

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Twinning
Ciprofloxacin
Molecules
Water
Synchrotrons
Dermatoglyphics
X-Ray Diffraction
Names
Anti-Bacterial Agents
Hydrates
X ray diffraction

Keywords

  • anti-bacterial agents
  • ciprofloxacin
  • crystallography, X-ray
  • hydrogen bonding
  • isoquinolines
  • molecular structure
  • piperazines
  • water
  • X-ray diffraction

Cite this

Fabbiani, Francesca P A ; Arlin, Jean Baptiste ; Buth, Gernot ; Dittrich, Birger ; Florence, Alastair J ; Herbst-Irmer, Regine ; Sowa, Heidrun. / Intermolecular interactions, disorder and twinning in ciprofloxacin-2,2-difluoroethanol (2/3) and ciprofloxacin-water (3/14.5). In: Acta Crystallographica Section C: Crystal Structure Communications. 2011 ; Vol. 67, No. 3. pp. o120-o124.
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abstract = "The antibiotic ciprofloxacin [systematic name: 1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-4-ium-1-yl)-1,4-dihydroquinoline-3-carboxylate], has been crystallized as a 2:3 solvate with 2,2-difluoroethanol, 2C(17)H(18)FN(3)O(3)·3C(2)H(4)O(2), (I), and as a 3:14.5 hydrate, 3C(17)H(18)FN(3)O(3)·14.5H(2)O, (II). The structure of (I) was determined using synchrotron X-ray diffraction data and refined as a two-component nonmerohedral twin. Both structures contain several independent molecules in the asymmetric unit: (I) contains two zwitterionic ciprofloxacin molecules and three difluoroethanol solvent molecules, while (II) contains three zwitterionic ciprofloxacin molecules and a mixture of ordered and disordered water molecules. The intermolecular interactions were analysed using fingerprint plots derived from Hirshfeld surfaces, providing a detailed description of the unique environment of each independent ciprofloxacin molecule.",
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Intermolecular interactions, disorder and twinning in ciprofloxacin-2,2-difluoroethanol (2/3) and ciprofloxacin-water (3/14.5). / Fabbiani, Francesca P A; Arlin, Jean Baptiste; Buth, Gernot; Dittrich, Birger; Florence, Alastair J; Herbst-Irmer, Regine; Sowa, Heidrun.

In: Acta Crystallographica Section C: Crystal Structure Communications, Vol. 67, No. 3, 03.2011, p. o120-o124.

Research output: Contribution to journalArticle

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T1 - Intermolecular interactions, disorder and twinning in ciprofloxacin-2,2-difluoroethanol (2/3) and ciprofloxacin-water (3/14.5)

AU - Fabbiani, Francesca P A

AU - Arlin, Jean Baptiste

AU - Buth, Gernot

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AU - Sowa, Heidrun

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KW - water

KW - X-ray diffraction

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