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Hydrogen bonded networks in hydrophilic channels: crystal structure of hydrated Ciprofloxacin Lactate and comparison with structurally similar compounds

Prasanna, MD and Row, Guru TN (2001) Hydrogen bonded networks in hydrophilic channels: crystal structure of hydrated Ciprofloxacin Lactate and comparison with structurally similar compounds. In: Journal of Molecular Structure, 559 (1-3). pp. 255-261.

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Abstract

Ciprofloxacin Lactate {4-(3-carboxy-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-quinolinyl-)-1-piperazinium-lactate–water (1/1/1.5)} $(C_{20}H_{24}N_3O_6 F_1·5H_2O)$ belonging to the family of fluoroquinolone antibacterial agents with wide spectrum activity has been studied using single crystal X-ray diffraction techniques. The crystal structure has channels running along crystallographic b-axis with $\pi$-stacks of Ciprofloxacin moieties linked through water molecules. A ten-membered hydrogen bonded pattern formed by centrosymmetrically related lactate and water molecules fill the center of the channel. The molecular assembly viewed down the b-axis depicts an infinitely extended open framework channels with the major diameter of about 10.60 $\AA$ and minor diameter of 4.79 $\AA$ . The structure also has a C–H· ··F intramolecular interaction and an intramolecular hydrogen bond. Analysis of the structures containing 7-piperazin-1-oyl-quinolin-4(1H)-one moiety using the Cambridge Structural Database reveals that a majority of the structures show the propensity to form channels via $\pi\cdot\cdot\cdot\pi$ interactions. Also, a detailed comparative study with the structure of magnesium sulfate adduct of ciprofloxacin shows that such interactions lead to similar molecular assemblies.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Elsevier.
Keywords: Ciprofloxacin Lactate; Channel structure; Hydrogen bonding; p-Stacking; Weak interactions
Department/Centre: Division of Chemical Sciences > Solid State & Structural Chemistry Unit
Division of Chemical Sciences > Organic Chemistry
Date Deposited: 03 Jun 2006
Last Modified: 19 Sep 2010 04:28
URI: http://eprints.iisc.ernet.in/id/eprint/7464

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