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

doi:10.1107/S0108270111005488

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

Strathclyde Institute Of Pharmacy And Biomedical Sciences

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

16 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.

Original language	English
Pages (from-to)	o120-o124
Number of pages	5
Journal	Acta Crystallographica Section C: Crystal Structure Communications
Volume	67
Issue number	3
DOIs	https://doi.org/10.1107/S0108270111005488
Publication status	Published - Mar 2011

Keywords

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

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10.1107/S0108270111005488

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

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.",

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

author = "Fabbiani, {Francesca P A} and Arlin, {Jean Baptiste} and Gernot Buth and Birger Dittrich and Florence, {Alastair J} and Regine Herbst-Irmer and Heidrun Sowa",

year = "2011",

month = mar,

doi = "10.1107/S0108270111005488",

language = "English",

volume = "67",

pages = "o120--o124",

journal = "Acta Crystallographica Section C: Crystal Structure Communications",

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

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

TY - JOUR

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

AU - Dittrich, Birger

AU - Florence, Alastair J

AU - Herbst-Irmer, Regine

AU - Sowa, Heidrun

PY - 2011/3

Y1 - 2011/3

N2 - 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.

AB - 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.

KW - anti-bacterial agents

KW - ciprofloxacin

KW - crystallography, X-ray

KW - hydrogen bonding

KW - isoquinolines

KW - molecular structure

KW - piperazines

KW - water

KW - X-ray diffraction

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DO - 10.1107/S0108270111005488

M3 - Article

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SP - o120-o124

JO - Acta Crystallographica Section C: Crystal Structure Communications

JF - Acta Crystallographica Section C: Crystal Structure Communications

IS - 3

ER -

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

Abstract

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Physical Organic Chemistry: Opportunities In Synthesis, Materials And Pharmaceuticals (Science And Innovation Award)

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

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Physical Organic Chemistry: Opportunities In Synthesis, Materials And Pharmaceuticals (Science And Innovation Award)

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