Limits...
Crystal structure of 4-amino-5-fluoro-2-oxo-2,3-di-hydro-pyrimidin-1-ium 3-hy-droxy-pyridine-2-carboxyl-ate.

Karthikeyan A, Thomas Muthiah P, Perdih F - Acta Crystallogr Sect E Struct Rep Online (2014)

Bottom Line: 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.

View Article: PubMed Central - HTML - PubMed

Affiliation: School of Chemistry, Bharathidasan University, Tiruchirappalli 620 024, Tamilnadu, India.

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.

No MeSH data available.


Related in: MedlinePlus

The wavy sheets inter­linked by C—H⋯O hydrogen bonds. Dashed lines represent hydrogen bonds (see Table 1 ▶ for details).
© Copyright Policy - open-access
Related In: Results  -  Collection

License
getmorefigures.php?uid=PMC4257234&req=5

fig3: The wavy sheets inter­linked by C—H⋯O hydrogen bonds. Dashed lines represent hydrogen bonds (see Table 1 ▶ for details).

Mentions: In the crystal structure, the carboxyl­ate group of the 3-hy­droxy­picolinate anion (O3 and O4) inter­acts with the proton­ated N3 atom and the 4-amino group of the 5-fluoro­cytosinium moiety through a pair of N—H⋯O hydrogen bonds, forming a robust (8) motif (Etter, 1990 ▶; Bernstein et al., 1995 ▶). The 3-hy­droxy­picolinate (N2 and C12) atoms inter­act with the N1 atom and the exocyclic oxygen O2 atom of the 5-fluoro­cytosinium moiety through a pair of N—H⋯N and C—H⋯O hydrogen bonds, forming an (7) motif. This type of motif rarely occurs in cytosinium carboxyl­ate inter­actions (Benali-Cherif et al., 2009 ▶). The motif is further connected on the other side by (12) and (18) motifs formed (Bernstein et al., 1995 ▶) through C—H⋯O and N—H⋯O hydrogen bonds involving the O2 and N4 atoms of the 5-fluoro­cytosinium cation and the symmetry-related C6 atom of the another cytosinium cation and O1 atoms of 3-hy­droxy­picolinate anions, generating a wavy sheet-like structure parallel to (010) (Fig. 2 ▶). These wavy sheets are inter­connected via C10—H10⋯O2 hydrogen bonds (Fig. 3 ▶). The crystal structure is further stabilized by C—H⋯π inter­actions between 3-hy­droxy­picolinate anions, Table 1 ▶.


Crystal structure of 4-amino-5-fluoro-2-oxo-2,3-di-hydro-pyrimidin-1-ium 3-hy-droxy-pyridine-2-carboxyl-ate.

Karthikeyan A, Thomas Muthiah P, Perdih F - Acta Crystallogr Sect E Struct Rep Online (2014)

The wavy sheets inter­linked by C—H⋯O hydrogen bonds. Dashed lines represent hydrogen bonds (see Table 1 ▶ for details).
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4257234&req=5

fig3: The wavy sheets inter­linked by C—H⋯O hydrogen bonds. Dashed lines represent hydrogen bonds (see Table 1 ▶ for details).
Mentions: In the crystal structure, the carboxyl­ate group of the 3-hy­droxy­picolinate anion (O3 and O4) inter­acts with the proton­ated N3 atom and the 4-amino group of the 5-fluoro­cytosinium moiety through a pair of N—H⋯O hydrogen bonds, forming a robust (8) motif (Etter, 1990 ▶; Bernstein et al., 1995 ▶). The 3-hy­droxy­picolinate (N2 and C12) atoms inter­act with the N1 atom and the exocyclic oxygen O2 atom of the 5-fluoro­cytosinium moiety through a pair of N—H⋯N and C—H⋯O hydrogen bonds, forming an (7) motif. This type of motif rarely occurs in cytosinium carboxyl­ate inter­actions (Benali-Cherif et al., 2009 ▶). The motif is further connected on the other side by (12) and (18) motifs formed (Bernstein et al., 1995 ▶) through C—H⋯O and N—H⋯O hydrogen bonds involving the O2 and N4 atoms of the 5-fluoro­cytosinium cation and the symmetry-related C6 atom of the another cytosinium cation and O1 atoms of 3-hy­droxy­picolinate anions, generating a wavy sheet-like structure parallel to (010) (Fig. 2 ▶). These wavy sheets are inter­connected via C10—H10⋯O2 hydrogen bonds (Fig. 3 ▶). The crystal structure is further stabilized by C—H⋯π inter­actions between 3-hy­droxy­picolinate anions, Table 1 ▶.

Bottom Line: 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.

View Article: PubMed Central - HTML - PubMed

Affiliation: School of Chemistry, Bharathidasan University, Tiruchirappalli 620 024, Tamilnadu, India.

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.

No MeSH data available.


Related in: MedlinePlus