2,6-Diaminopyrimidin-4(3<i>H</i>)-one–4-nitrobenzoic acid (1/1)

Subashini, A.; Muthiah, Packianathan Thomas; Bocelli, Gabriele; Cantoni, A.

doi:10.1107/s1600536807047861

Cited by 2 publications

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References 7 publications

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“…Pyrimidine and aminopyrimidine derivatives are biologically important for they occur in nature as components of nucleic acid and drugs. , Several co-crystals of aminopyrimidine and pyridine derivatives have been reported earlier from our group. − In the present study, 17 co-crystals using aminopyrimidine bases, 2-amino-4, 6-dimethylpyrimidine (MP) and 2-amino-4-chloro-6-methylpyrimidine (CP), with various acids (Scheme ) are prepared in which the two bases differ only by a chlorine/methyl group at C4 of the pyrimidine ring. Thus, the availability of a series of isostructural co-crystals offers an opportunity to determine the structural packing arrangement and their similarities.…”

Section: Introductionmentioning

confidence: 92%

Design of a Series of Isostructural Co-Crystals with Aminopyrimidines: Isostructurality through Chloro/Methyl Exchange and Studies on Supramolecular Architectures

Ebenezer

Muthiah

Butcher

2011

Crystal Growth & Design

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A series of 17 co-crystals involving 2-amino-4-chloro-6-methyl pyrimidine/2-amino-4,6-dimethyl pyrimidine with various carboxylic acids, C7H5O2-R (where R = H, Cl, CH3, NO2, OCH3, COOH) and C9H8O2, have been prepared in which the analogues differ only with respect to chlorine and methyl groups. The basis of this work is the formation of isostructural co-crystals based on the chloro/methyl interchange. The results show good success in the harvest of isostructural compounds. Isostructurality calculations have been carried out in order to substantiate these results. Apart from this some of the compounds have been identified to show good resemblance in their structure, yet do not have any relation based on chloro/methyl interchange. This is explained by the fact that all the co-crystals in the present study tend to form one common supermolecule: a linear heterotetramer. This supermolecule is known to be the most stable and reliable heterotetramer formed between an aminopyrimidine and benzoic acid, according to a recent report, which is believed to be responsible for the isostructurality other than chloro/methyl exchange.

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Section: Introductionmentioning

confidence: 92%

Design of a Series of Isostructural Co-Crystals with Aminopyrimidines: Isostructurality through Chloro/Methyl Exchange and Studies on Supramolecular Architectures

Ebenezer

Muthiah

Butcher

2011

Crystal Growth & Design

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Pseudopolymorphs of 2,6-diaminopyrimidin-4-one and 2-amino-6-methylpyrimidin-4-one: one or two tautomers present in the same crystal

2011

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The derivatives of pyrimidin-4-one can adopt either a 1H- or a 3H-tautomeric form, which affects the hydrogen-bonding interactions in cocrystals with compounds containing complementary functional groups. In order to study their tautomeric preferences, we crystallized 2,6-diaminopyrimidin-4-one and 2-amino-6-methylpyrimidin-4-one. During various crystallization attempts, four structures of 2,6-diaminopyrimidin-4-one were obtained, namely solvent-free 2,6-diaminopyrimidin-4-one, C(4)H(6)N(4)O, (I), 2,6-diaminopyrimidin-4-one-dimethylformamide-water (3/4/1), C(4)H(6)N(4)O·1.33C(3)H(7)NO·0.33H(2)O, (Ia), 2,6-diaminopyrimidin-4-one dimethylacetamide monosolvate, C(4)H(6)N(4)O·C(4)H(9)NO, (Ib), and 2,6-diaminopyrimidin-4-one-N-methylpyrrolidin-2-one (3/2), C(4)H(6)N(4)O·1.5C(5)H(9)NO, (Ic). The 2,6-diaminopyrimidin-4-one molecules exist only as 3H-tautomers. They form ribbons characterized by R(2)(2)(8) hydrogen-bonding interactions, which are further connected to form three-dimensional networks. An intermolecular N-H···N interaction between amine groups is observed only in (I). This might be the reason for the pyramidalization of the amine group. Crystallization experiments on 2-amino-6-methylpyrimidin-4-one yielded two isostructural pseudopolymorphs, namely 2-amino-6-methylpyrimidin-4(3H)-one-2-amino-6-methylpyrimidin-4(1H)-one-dimethylacetamide (1/1/1), C(5)H(7)N(3)O·C(5)H(7)N(3)O·C(4)H(9)NO, (IIa), and 2-amino-6-methylpyrimidin-4(3H)-one-2-amino-6-methylpyrimidin-4(1H)-one-N-methylpyrrolidin-2-one (1/1/1), C(5)H(7)N(3)O·C(5)H(7)N(3)O·C(5)H(9)NO, (IIb). In both structures, a 1:1 mixture of 1H- and 3H-tautomers is present, which are linked by three hydrogen bonds similar to a Watson-Crick C-G base pair.

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2,6-Diaminopyrimidin-4(3H)-one–4-nitrobenzoic acid (1/1)

Cited by 2 publications

References 7 publications

Design of a Series of Isostructural Co-Crystals with Aminopyrimidines: Isostructurality through Chloro/Methyl Exchange and Studies on Supramolecular Architectures

Design of a Series of Isostructural Co-Crystals with Aminopyrimidines: Isostructurality through Chloro/Methyl Exchange and Studies on Supramolecular Architectures

Pseudopolymorphs of 2,6-diaminopyrimidin-4-one and 2-amino-6-methylpyrimidin-4-one: one or two tautomers present in the same crystal

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