Abstract

In the title mol-ecular salt, 2C6H10N3O+·C8H4O42-, the N atom of each of the two 2-amino-4-meth-oxy-6-methyl-pyrimidine mol-ecules lying between the amine and methyl groups has been protonated. The dihedral angles between the pyrimidine rings of the cations and the benzene ring of the succinate dianion are 5.04 (8) and 7.95 (8)°. Each of the cations is linked to the anion through a pair of N-H⋯O(carboxyl-ate) hydrogen bonds, forming cyclic R22(8) ring motifs which are then linked through inversion-related N-H⋯O hydrogen bonds, giving a central R24(8) motif. Peripheral amine N-H⋯O hydrogen-bonding inter-actions on either side of the succinate anion, also through centrosymmetric R22(8) extensions, form one-dimensional ribbons extending along [211]. The crystal structure also features π-π stacking inter-actions between the aromatic rings of the pyrimidine cations [minimum ring centroid separation = 3.6337 (9) Å]. The inter-molecular inter-actions were also investigated using Hirshfeld surface studies and two-dimensional fingerprint images.

Highlights

  • 2-amino-4-methoxy-6-methylpyrimidine molecules lying between the amine and methyl groups has been protonated

  • The dihedral angles between the pyrimidine rings of the cations and the benzene ring of the succinate dianion are 5.04 (8)

  • Hydrogen bonding plays a vital role in molecular recognition

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Summary

Chemical context

Pyrimidine and aminopyrimidine derivatives have useful applications in many fields, for example as pesticides and pharmaceutical agents (Condon et al, 1993), while imazosulfuron, ethirmol and mepanipyrim have been commercialized as agrochemicals (Maeno et al, 1990). Hydrogen bonding plays a vital role in molecular recognition. It is significant to know the types of hydrogen bonds present to design new materials with highly specific features. Supramolecular chemistry plays a pivotal role in many biological systems and is involved in artificial systems. It refers to the specific relation between two or more molecules through non-covalent interactions such as hydrogen bonding, hydrophobic forces, van der Waals forces and – interactions. Symmetry codes: (i) x þ 2; y þ 2; z þ 1; (ii) x; y þ 1; z

Structural commentary
Supramolecular features
Hirshfeld surface analysis
Database survey
Synthesis and crystallization
Full Text
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