Abstract
The synthesis, structural characterization and influence of solvents on the crystal packing of solvated complexes of ethacridine with phthalic acid: 6,9-diamino-2-ethoxyacridinium phthalate methanol solvate (1), 6,9-diamino-2-ethoxyacridinium phthalate ethanol solvate (2), 6,9-diamino-2-ethoxyacridinium phthalate isobutanol solvate (3), and 6,9-diamino-2-ethoxyacridinium phthalate tert-butanol solvate monohydrate (4) are described in this article. Single-crystal XRD measurements revealed that the compounds 1–4 crystallized in the triclinic P-1 space group, and the 6,9-diamino-2-ethoxyacridinium cations, phthalic acid anions and solvent molecules interact via strong N–H···O, O–H···O, C–H···O hydrogen bonds, and C–H···π and π–π interactions to form different types of basic structural motifs, such as: heterotetramer bis[···cation···anion···] in compound 1 and 2, heterohexamer bis[···cation···alcohol···anion···] in compound 3, and heterohexamer bis[···cation···water···anion···] in compound 4. Presence of solvents molecule(s) in the crystals causes different supramolecular synthons to be obtained and thus has an influence on the crystal packing of the compounds analyzed.
Highlights
IntroductionPresence of solvents molecule(s) in the crystals causes different supramolecular synthons to be obtained and has an influence on the crystal packing of the compounds analyzed
Considering the above, in this paper, we describe the synthesis and structural characterization of four solvated complexes of ethacridine (6,9-diamino-2-ethoxyacridine) with phthalic acid, prepared using different solvents
The 6,9-diamino-2-etoxyacridine cation is linked with phthalic acid anion by N(acridine) –H···O(carboxy) [d(H10···O28) = 1.96(2) Å and ∠(N10–H10···O28) = 172(3)◦ ], and N(9-amino) –H···O(carboxy) [d(H15A···O27) = 2.11(3) Å and ∠(N15–H15A···O27) = 155(2)◦ ] hydrogen bonds to form a cyclic heterotetramer (Table 2, Figure 2a) [48,49]
Summary
Presence of solvents molecule(s) in the crystals causes different supramolecular synthons to be obtained and has an influence on the crystal packing of the compounds analyzed. A commonly available drug, ethacridine lactate monohydrate (acrinol) exhibits antiviral properties and is helpful in curing suppurating infections, inflamed wounds, burns, as well as local infections of the mouth and throat, and inhibits protein synthesis in bacterial cells [2,3]. From a structural point of view, ethacridine is a poorly known compound. The reason for such a small number of structures is the difficulty of obtaining single crystals of high purity and appropriate quality of XRD experiments
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