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Crystal structure and hydrogen-bonding patterns in 5-fluoro-cytosinium picrate.

ABSTRACT: In the crystal structure of the title compound, 5-fluoro-cytosinium picrate, C₄H₅FN₃O⁺·C₆H₂N₃O₇^-, one N heteroatom of the 5-fluoro-cytosine (5FC) ring is protonated. The 5FC ring forms a dihedral angle of 19.97?(11)° with the ring of the picrate (PA^-) anion. In the crystal, the 5FC⁺ cation inter-acts with the PA^- anion through three-centre N-H?O hydrogen bonds, forming two conjoined rings having R₂¹(6) and R₁²(6) motifs, and is extended by N-H?O hydrogen bonds and C-H?O inter-actions into a two-dimensional sheet structure lying parallel to (001). Also present in the crystal structure are weak C-F?? inter-actions.

SUBMITTER: Mohana M

PROVIDER: S-EPMC5347054 | biostudies-literature | 2017 Mar

REPOSITORIES: biostudies-literature

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Crystal structure and hydrogen-bonding patterns in 5-fluoro-cytosinium picrate.

Mohana Marimuthu M Thomas Muthiah Packianathan P McMillen Colin D CD

Acta crystallographica. Section E, Crystallographic communications 20170214 Pt 3

In the crystal structure of the title compound, 5-fluoro-cytosinium picrate, C4H5FN3O+·C6H2N3O7-, one N heteroatom of the 5-fluoro-cytosine (5FC) ring is protonated. The 5FC ring forms a dihedral angle of 19.97 (11)° with the ring of the picrate (PA-) anion. In the crystal, the 5FC+ cation inter-acts with the PA- anion through three-centre N-H⋯O hydrogen bonds, form ...[more]

PMID: 28316809

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Project description:BackgroundTrimethoprim [2,4-diamino-5-(3',4',5'-trimethoxybenzyl)pyrimidine] is an antifolate drug. It selectively inhibits the bacterial dihydrofolate reductase (DHFR) enzyme.ResultsIn the crystal structures of trimethoprim (TMP)-hydrogen phthalate (1) and trimethoprim-hydrogen adipate (2), one of the N atoms of the pyrimidine ring is protonated and it interacts with the deprotonated carboxylate oxygens through a pair of nearly parallel N-H...O hydrogen bonds to form a fork-like interaction. In the compound 1, the pyrimidine moieties of the TMP cations are centrosymmetrically paired through a pair of N-H...N hydrogen bonds involving 4-amino group and the N (N3) atom of the pyrimidine rings to form a 8-membered hydrogen bonded ring [R2(2)(8)]. The 4-amino group of one TMP moiety and 2-amino group of another TMP moiety (both moieties are members of a base pair) are bridged by the carbonyl oxygen of the phthalate moiety through N-H...O hydrogen bonds forming 8-membered hydrogen-bonded ring [R2(2)(8)]. The characteristic hydrogen-bonded rings observed in the structure aggregate into a supramolecular ladder consisting of a pair of chains, each of which is built up of alternate TMP and hydrogen phthalate ions. In the compound 2, two TMP cations and two hydrogen adipate anions are arranged about an inversion center so that the complementary DDAA (D = donor, A = acceptor) arrays of quadruple hydrogen-bonding patterns are formed. The head-to-tail arrangement of the hydrogen adipate ions leads to a hydrogen-bonded supramolecular chain. From crystal engineering point of view, it is interesting to note that the compound 1 has a hydrogen-bonded network remarkably identical with its aliphatic analogue, trimethoprim hydrogen maleate. Similarly the compound 2, resembles its homolog trimethoprim hydrogen glutarate.ConclusionIn the crystal structure of trimethoprim hydrogen phthalate, the hydrogen-bonded network is remarkably identical with its aliphatic analogue, trimethoprim hydrogen maleate. Similarly in the crystal structure of trimethoprim hydrogen adipate the hydrogen bonded network resembles its homolog trimethoprim hydrogen glutarate.

Dataset Information

Crystal structure and hydrogen-bonding patterns in 5-fluoro-cytosinium picrate.

Publications

Crystal structure and hydrogen-bonding patterns in 5-fluoro-cytosinium picrate.

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