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Enrofloxacin hydro-chloride dihydrate
Jorge E Miranda-Calderón1, Lilia Gutiérrez1, Marcos Flores-Alamo2
1Departamento de Fisiología y Farmacología, Facultad de Medicina Veterinaria y Zootecnia, Universidad Nacional Autónoma de México, Av. Universidad 3000, Delegación Coyoacán, Ciudad de México, CP 04510, Mexico.
Summary
This study details the crystal structure of protonated enrofloxacin chloride dihydrate. It reveals specific molecular conformations and intermolecular interactions, including hydrogen bonds and pi-pi stacking, forming a 3D crystal lattice.
Area of Science:
- Crystallography
- Supramolecular Chemistry
- Medicinal Chemistry
Background:
- Enrofloxacin is a widely used fluoroquinolone antibiotic.
- Understanding its crystalline structure is crucial for pharmaceutical development and formulation.
- The presence of water molecules and counterions can significantly influence drug properties.
Purpose of the Study:
- To elucidate the detailed crystal structure of enrofloxacin chloride dihydrate.
- To characterize the molecular conformation and intermolecular interactions within the crystal lattice.
- To provide insights into the solid-state behavior of enrofloxacin.
Main Methods:
- Single-crystal X-ray diffraction analysis was employed.
- The asymmetric unit composition and crystallographic parameters were determined.
- Hydrogen bonding networks and π-π interactions were analyzed.
Main Results:
- The asymmetric unit contains two independent protonated enrofloxacin monocations, two chloride anions, and four water molecules.
- Piperazinium rings adopt chair conformations with specific dihedral angles between the cyclopropyl and quinoline ring systems.
- Intramolecular hydrogen bonds were observed within each cation, and intermolecular interactions (O-H⋯Cl, N-H⋯Cl, O-H⋯O, π-π stacking) form a 3D array.
Conclusions:
- The crystal structure of enrofloxacin chloride dihydrate has been successfully determined.
- The study highlights the importance of hydrogen bonding and π-π interactions in stabilizing the crystal structure.
- These findings contribute to a deeper understanding of fluoroquinolone solid-state chemistry.