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Hydrogen-bonding patterns in the cocrystal 2-amino-4,6-dimethoxy-pyrimidine-anthranilic acid (1/1).

ABSTRACT: In the title cocrystal, C(6)H(9)N(3)O(2)·C(7)H(7)NO(2), the asymmetric unit contains two crystallographically independent 2-amino-4,6-dimeth-oxy pyrimidine-anthranilic acid adducts. The 2-amino-4,6-dimeth-oxy pyrimidine mol-ecules inter-act with the carboxylic group of the respective anthranilic acid mol-ecules through N-H?O and O-H?N hydrogen bonds, forming a cyclic hydrogen-bonded motif R(2) (2)(8). The pyrimidine mol-ecules also form base pairs via a pair of N-H?N hydrogen bonds, forming another R(2) (2)(8) motif. The typical intra-molecular N-H?O hydrogen bond is observed in the anthranilic acid mol-ecules. Furthermore, the crystal structure is stabilized by C-H?O hydrogen bonds.

SUBMITTER: Thanigaimani K

PROVIDER: S-EPMC2915181 | biostudies-literature | 2007 Dec

REPOSITORIES: biostudies-literature

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Hydrogen-bonding patterns in the cocrystal 2-amino-4,6-dimethoxy-pyrimidine-anthranilic acid (1/1).

Thanigaimani Kaliyaperumal K Muthiah Packianathan Thomas PT Lynch Daniel E DE

Acta crystallographica. Section E, Structure reports online 20071206 Pt 1

In the title cocrystal, C(6)H(9)N(3)O(2)·C(7)H(7)NO(2), the asymmetric unit contains two crystallographically independent 2-amino-4,6-dimeth-oxy pyrimidine-anthranilic acid adducts. The 2-amino-4,6-dimeth-oxy pyrimidine mol-ecules inter-act with the carboxylic group of the respective anthranilic acid mol-ecules through N-H⋯O and O-H⋯N hydrogen bonds, forming a cyclic hydrogen-bonded motif R(2) (2)(8). The pyrimidine mol-ecules also form base pairs via a pair of N-H⋯N hydrogen bonds, forming anot ...[more]

PMID: 21200672

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Project description:The pharmaceutical cocrystal of caffeine-citric acid (CAF-CA, Form II) has been studied to explore the presence of hydrogen bonding interactions and structure-reactivity-property relationship between the two constituents CAF and Citric acid. The cocrystal was prepared by slurry crystallization. Powder X-ray diffraction (PXRD) analysis was done to characterize CAF-CA cocrystal. Also, differential scanning calorimetry (DSC) confirmed the existence of CAF-CA cocrystal. The vibrational spectroscopic (FT-IR and FT-Raman) signatures and quantum chemical approach have been used as a strategy to get insights into structural and spectral features of CAF-CA cocrystal. There was a good correlation among the experimental and theoretical results of dimer of cocrystal, as this model is capable of covering all nearest possible interactions present in the crystal structure of cocrystal. The spectroscopic results confirmed that (O33-H34) mode forms an intramolecular (C25 = O28∙∙∙H34-O33), while (O26-H27) (O39-H40) and (O43-H44) groups form intermolecular hydrogen bonding (O26-H27∙∙∙N24-C22, O39-H40∙∙∙O52 = C51 and O43-H44∙∙∙O86 = C83) in cocrystal due to red shifting and increment in bond length. The quantum theory of atoms in molecules (QTAIM) analysis revealed (O88-H89∙∙∙O41) as strongest intermolecular hydrogen bonding interaction with interaction energy -12.4247 kcal mol-1 in CAF-CA cocrystal. The natural bond orbital analysis of the second-order theory of the Fock matrix highlighted the presence of strong interactions (N∙∙∙H and O∙∙∙H) in cocrystal. The HOMO-LUMO energy gap value shows that the CAF-CA cocrystal is more reactive, less stable and softer than CAF active pharmaceutical ingredients. The electrophilic and nucleophilic reactivities of atomic sites involved in intermolecular hydrogen bond interactions in cocrystal have been demonstrated by mapping electron density isosurfaces over electrostatic potential i.e. plotting molecular electrostatic potential (MESP) map. The molar refractivity value of cocrystal lies within the set range by Lipinski and hence it may be used as orally active form. The results show that the physicochemical properties of CAF-CA cocrystal are enhanced in comparison to CAF (API).

Dataset Information

Hydrogen-bonding patterns in the cocrystal 2-amino-4,6-dimethoxy-pyrimidine-anthranilic acid (1/1).

Publications

Hydrogen-bonding patterns in the cocrystal 2-amino-4,6-dimethoxy-pyrimidine-anthranilic acid (1/1).

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