Prasanna, M. D. ; Guru Row, T. N. (2001) Hydrogen bonded networks in hydrophilic channels: crystal structure of hydrated ciprofloxacin lactate and comparison with structurally similar compounds Journal of Molecular Structure, 559 (1-3). pp. 255-261. ISSN 0022-2860
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00222...
Related URL: http://dx.doi.org/10.1016/S0022-2860(00)00701-8
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)}(C20H24N3O6F1.5H2O) 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 π-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 Å and minor diameter of 4.79 Å. 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 π…π 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: | Article |
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Source: | Copyright of this article belongs to Elsevier Science. |
Keywords: | Ciprofloxacin Lactate; Channel Structure; Hydrogen Bonding; π-Stacking; Weak Interactions |
ID Code: | 12012 |
Deposited On: | 10 Nov 2010 05:07 |
Last Modified: | 03 Jun 2011 04:24 |
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