Pyrimidine-2,4-diamine acetone monosolvate

Draguta, Sergiu; Sandhu, Bhupinder; Khrustalev, Victor N.; Fonarı, Marina S.; Timofeeva, Tatiana V.

doi:10.1107/s1600536813001025

Cited by 4 publications

(2 citation statements)

References 6 publications

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“…It is worth mentioning the fact that five of six adducts reported here have acentric crystal structures in spite of achiral component molecules. It should be mentioned also that among starting aminopyridines [71][72][73][74][75][76] including our recently reported crystal structures 5 and acetone solvate 6, 75,76 four are non-centrosymmetric. This is rather uncommon for achiral molecules and their co-crystalline adducts.…”

Section: Statistical Analysis Of the Crystal Structuresmentioning

confidence: 78%

New acentric materials constructed from aminopyridines and 4-nitrophenol

et al. 2013

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Co-crystallization of 4-nitrophenol (I) with five aminopyridines (4-aminopyridine 1, 3,4-diaminopyridine 2, 2,3-diaminopyridine 3, 3-aminopyridine 4, 2-amino-6-methylpyridine 5) and 2,4-diaminopyrimidine 6 resulted in six adducts with the ratio of components 2 : 1 in five and 1 : 1 in one final compounds. Single crystals were grown by slow evaporation technique using ethanol as a solvent. Five adducts with 1-5 crystallize in acentric P2 1 and Pna2 1 space groups, and one, 2(I)?6 -in centrosymmetric P2 1 /c space group.Compounds 2(I)?1, 2(I)?2, 2(I)?3 are isomorphous, and demonstrate similar H-bonding patterns despite the differences in aminopyridine molecules. Compound 2(I)?5 is isomorphous to two previously reported compounds. Adducts 2(I)?1, 2(I)?2, 2(I)?3, 2(I)?5, 2(I)?6 represent organic salts composed of pyridinium/ pyrimidinium cation, 4-nitrophenolate anion, and 4-nitrophenol neutral molecule. The H-bonded 4-nitrophenol-4-nitrophenolate anionic dimers were found in all compounds with 2 : 1 molar ratio. In adduct I?4 both molecules are in neutral form. The IR spectral data support crystallographic conclusions on salts formation. Plane wave pseudopotential density functional theory calculations were used to predict hyperpolarizability tensor components. Our calculations suggest 2(I)?3 as the best candidate for nonlinear optical materials (14 times more active than urea). Recently, some success was achieved by co-crystallization of polar molecules with 1,2-bis(chloromercurio)tetrafluorobenzene where a strong intermolecular network is formed by the Hg and Cl atoms. 29,30 Several groups demonstrated enhance-

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Section: Statistical Analysis Of the Crystal Structuresmentioning

confidence: 78%

New acentric materials constructed from aminopyridines and 4-nitrophenol

et al. 2013

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“…).Slouf et al, 2002), one solvate, 2,4diaminopyrimidine-acetone (1/1) (LERYOY;Draguta, Sandhu et al, 2013), one salt, hydroxonium bis(2,4-diaminopyrimidinium) phosphate (TEGZIO01;…”

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confidence: 99%

6-Propyl-2-thiouracilversus6-methoxymethyl-2-thiouracil: enhancing the hydrogen-bonded synthon motif by replacement of a methylene group with an O atom

2016

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The understanding of intermolecular interactions is a key objective of crystal engineering in order to exploit the derived knowledge for the rational design of new molecular solids with tailored physical and chemical properties. The tools and theories of crystal engineering are indispensable for the rational design of (pharmaceutical) cocrystals. The results of cocrystallization experiments of the antithyroid drug 6-propyl-2-thiouracil (PTU) with 2,4-diaminopyrimidine (DAPY), and of 6-methoxymethyl-2-thiouracil (MOMTU) with DAPY and 2,4,6-triaminopyrimidine (TAPY), respectively, are reported. PTU and MOMTU show a high structural similarity and differ only in the replacement of a methylene group (-CH2-) with an O atom in the side chain, thus introducing an additional hydrogen-bond acceptor in MOMTU. Both molecules contain an ADA hydrogen-bonding site (A = acceptor and D = donor), while the coformers DAPY and TAPY both show complementary DAD sites and therefore should be capable of forming a mixed ADA/DAD synthon with each other, i.e. N-H...O, N-H...N and N-H...S hydrogen bonds. The experiments yielded one solvated cocrystal salt of PTU with DAPY, four different solvates of MOMTU, one ionic cocrystal of MOMTU with DAPY and one cocrystal salt of MOMTU with TAPY, namely 2,4-diaminopyrimidinium 6-propyl-2-thiouracilate-2,4-diaminopyrimidine-N,N-dimethylacetamide-water (1/1/1/1) (the systematic name for 6-propyl-2-thiouracilate is 6-oxo-4-propyl-2-sulfanylidene-1,2,3,6-tetrahydropyrimidin-1-ide), C4H7N4(+)·C7H9N2OS(-)·C4H6N4·C4H9NO·H2O, (I), 6-methoxymethyl-2-thiouracil-N,N-dimethylformamide (1/1), C6H8N2O2S·C3H7NO, (II), 6-methoxymethyl-2-thiouracil-N,N-dimethylacetamide (1/1), C6H8N2O2S·C4H9NO, (III), 6-methoxymethyl-2-thiouracil-dimethyl sulfoxide (1/1), C6H8N2O2S·C2H6OS, (IV), 6-methoxymethyl-2-thiouracil-1-methylpyrrolidin-2-one (1/1), C6H8N2O2S·C5H9NO, (V), 2,4-diaminopyrimidinium 6-methoxymethyl-2-thiouracilate (the systematic name for 6-methoxymethyl-2-thiouracilate is 4-methoxymethyl-6-oxo-2-sulfanylidene-1,2,3,6-tetrahydropyrimidin-1-ide), C4H7N4(+)·C6H7N2O2S(-), (VI), and 2,4,6-triaminopyrimidinium 6-methoxymethyl-2-thiouracilate-6-methoxymethyl-2-thiouracil (1/1), C4H8N5(+)·C6H7N2O2S(-)·C6H8N2O2S, (VII). Whereas in (I) only an AA/DD hydrogen-bonding interaction was formed, the structures of (VI) and (VII) both display the desired ADA/DAD synthon. Conformational studies on the side chains of PTU and MOMTU also revealed a significant deviation for cocrystals (VI) and (VII), leading to the desired enhancement of the hydrogen-bond pattern within the crystal.

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