Abstract
The asymmetric unit of the title salt, C4H5FN3O(+)·C6H4NO3 (-), contains one 4-amino-5-fluoro-2-oxo-2,3-di-hydro-pyrimidin-1-ium (5-fluoro-cytosinium, 5FC) cation and a 3-hy-droxy-picolinate (3HAP) anion. The 4-amino-5-fluoro-2-oxo-2,3-di-hydro-pyrimidine mol-ecule is protonated at one of the pyrimidine N atoms. The typical intra-molecular N-H⋯F and O-H⋯O S(5) and S(6) hydrogen-bond ring motifs are observed in the cations and anions. The protonated N atom and 2-amine group of the 5FC cation inter-act with the 3HPA anion through a pair of nearly parallel N-H⋯O hydrogen bonds, forming a robust R 2 (2)(8) ring motif. The ions are further linked by N-H⋯N, O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds, generating R 2 (2)(7), R 3 (3)(12) and R 6 (5)(18) ring motifs, respectively, leading to supra-molecular wave-like sheets parallel to (010). The crystal structure is further stabilized by C-H⋯π inter-actions, generating a three-dimensional architecture.
Highlights
The protonated N atom and 2-amine group of the 5FC cation interact with the 3HPA anion through a pair of nearly parallel N—H O hydrogen bonds, forming a robust R22(8) ring motif
We report the molecular structure of the title salt, formed from the reaction of 5-fluorocytosine with 3-hydoi:10.1107/S1600536814021898
There is an intramolecular N—H F hydrogen bond with an S(5) ring motif between the N4 amino group and the F atom of the 5fluorocytosinum cation. These hydrogen-bonding parameters are similar to those observed in 5-fluorocytosinium salicylate (Prabakaran et al, 2001)
Summary
Fluorinated pyrimidine and purine derivatives have received much interest because of their wide range of biological applications (Giner-Sorolla & Bendich, 1958). 5-Fuorocytosine is a fluorinated pyrimidine derivative anti-metabolite drug and is extensively used as an anti-fungal agent for the treatment of Candida and Cryptococcus (Vermes et al., 2000). 5-Fluorocytosine is a versatile molecule that plays essential roles in many biological applications, such as antitumour, potential gene therapy and gene-directed prodrug therapy (GDEPT) in the treatment of cancer (Kohila et al., 2012). Fluorinated pyrimidine and purine derivatives have received much interest because of their wide range of biological applications (Giner-Sorolla & Bendich, 1958). 5-Fuorocytosine is a fluorinated pyrimidine derivative anti-metabolite drug and is extensively used as an anti-fungal agent for the treatment of Candida and Cryptococcus (Vermes et al., 2000). The crystal structures of 5-fluorocytosine monohydrate, 5-fluorocytosine co-crystals and salts have been reported The crystal structures of various salts and complexes of 3-hydroxypicolinic acid have been reported (Quintal et al, 2000; Soares-Santos et al., 2003; Betz and Gerber, 2011; Nirmalram et al, 2011). We report the molecular structure of the title salt, formed from the reaction of 5-fluorocytosine with 3-hydoi:10.1107/S1600536814021898.
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