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Trimolecular Co-crystals of Ciprofloxacin, p-Coumaric Acid, and Benzoic Acid or Salicylic Acid

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Abstract

Molecular salts formation is a simple and widely used approach to alter the physicochemical properties of active pharmaceutical ingredients, such as ciprofloxacin (CP), without modifying their chemical structures. In the current work, two co-crystals of p-coumaric acid (PCMA) and organic salts of CP cation (CPH) were prepared and characterized in solid state by X-ray diffraction and by NMR spectroscopy in solution. The two organic salts are CPH:benzoate anion (CPH:BA) and CPH:salicylate anion (CPH:SA). To our knowledge, these are the first two examples of co-crystals of CPH organic salt and a different organic acid. In the two co-crystals (CPH:BA:PCMA and CPH:SA:PCMA), the anion (BA or SA) connects the PCMA molecules and the CPH via O–H∙∙∙O and N–H∙∙∙O hydrogen bonding interactions. The ratio between the three crystalline species in the two co-crystals (CPH:BA:PCMA and CPH:SA:PCMA) is (1:1:1), the ratio was confirmed in solution by NMR spectroscopy.

Graphical Abstract

Co-Crystals of ciprofloxacinuim cation salts of salicylate or benzoate anions and p-coumaric acid have been studied in solution using NMR spectroscopy and in solid state using X-ray crystallography

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Data Availability

The crystallographic data including CIF and fcf files have been deposited into Cambridge Crystallographic Data Centre. CCDC 2044467 and 2044468 contain the crystallographic data. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures.

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Acknowledgements

The authors wish to thank the Deanship of Scientific Research at The University of Jordan for financial support (Grant recommendation No. 27/2014-2015).

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Authors and Affiliations

  1. Department of Chemistry, School of Science, The University of Jordan, Amman, 11942, Jordan

    Firas F. Awwadi

  2. Department of Pharmaceutical Sciences, School of Pharmacy, University of Jordan, Amman, 11942, Jordan

    Lina A. Dahabiyeh & Imad I. Hamdan

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  1. Firas F. Awwadi
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  2. Lina A. Dahabiyeh
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Correspondence to Firas F. Awwadi.

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Awwadi, F.F., Dahabiyeh, L.A. & Hamdan, I.I. Trimolecular Co-crystals of Ciprofloxacin, p-Coumaric Acid, and Benzoic Acid or Salicylic Acid. J Chem Crystallogr 52, 304–314 (2022). https://doi.org/10.1007/s10870-022-00925-5

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  • DOI: https://doi.org/10.1007/s10870-022-00925-5

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