The title pyrazine dicarboxamide ligand, , -bis-(quinolin-8-yl)pyrazine-2,3-dicarboxamide (), CHNO, has a twisted conformation with the outer quinoline groups being inclined to the central pyrazine ring by 9.00 (6) and 78.67 (5)°, and by 79.94 (4)° to each other. In the crystal, molecules are linked by C-H⋯O hydrogen bonds, forming layers parallel to the (10) plane, which are in turn linked by offset π-π inter-actions [inter-centroid distances 3.4779 (9) and 3.6526 (8) Å], forming a supra-molecular three-dimensional structure. Reaction of the ligand with Cu(ClO) in aceto-nitrile leads to the formation of the binuclear complex, [μ-(3-{hy-droxy[(quinolin-8-yl)imino]-meth-yl}pyrazin-2-yl)[(quinolin-8-yl)imino]-methano-lato]bis-[diaceto-nitrile-copper(II)] tris-(per-chlor-ate) aceto-nitrile disolvate, [Cu(CHNO)(CHCN)](ClO)·2CHCN or [Cu(HL1)(CHCN)](ClO)·2CHCN (). In the cation of complex , the ligand coordinates to the copper(II) atoms in a bis-tridentate fashion. A resonance-assisted O-H⋯O hydrogen bond is present in the ligand; the position of this H atom was located in a difference-Fourier map. Both copper(II) atoms are fivefold coordinate, being ligated by three N atoms of the ligand and by the N atoms of two aceto-nitrile mol-ecules. The first copper atom has a perfect square-pyramidal geometry while the second copper atom has a distorted shape. In the crystal, the cation and perchlorate anions are linked by a number of C-H⋯O hydrogen bonds, forming a supra-molecular three-dimensional structure.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7057382PMC
http://dx.doi.org/10.1107/S2056989020001838DOI Listing

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The title pyrazine dicarboxamide ligand, , -bis-(quinolin-8-yl)pyrazine-2,3-dicarboxamide (), CHNO, has a twisted conformation with the outer quinoline groups being inclined to the central pyrazine ring by 9.00 (6) and 78.67 (5)°, and by 79.

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The title ligand, CHNO·2HO () [,-bis-(pyridin-4-ylmeth-yl)pyrazine-2,3-dicarboxamide], crystallized as a dihydrate. The mol-ecule is U-shaped with the carboxamide groups being to one another, making a dihedral angle of 81.6 (5)°.

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The crystal structures of three pyrazine-2,5-dicarb-oxamides: three-dimensional supra-molecular structures.

Acta Crystallogr E Crystallogr Commun

May 2017

Institute of Physics, University of Neuchâtel, rue Emile-Argand 11, CH-2000 Neuchâtel, Switzerland.

The complete mol-ecules of the title compounds, ,-bis-(pyridin-2-ylmeth-yl)pyrazine-2,5-dicarboxamide, CHNO (I), 3,6-dimethyl-,-bis-(pyridin-2-yl-meth-yl)pyrazine-2,5-dicarboxamide, CHNO (II), and ,-bis-(pyridin-4-ylmeth-yl)pyrazine-2,5-dicarboxamide, CHNO (III), are generated by inversion symmetry, with the pyrazine rings being located about centres of inversion. Each mol-ecule has an extended conformation with the pyridine rings inclined to the pyrazine ring by 89.17 (7)° in (I), 75.

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Previous efforts led to dicarboxamide derivatives like 1.3, comprising either an imidazole, pyrazine or fenyl ring as the central scaffold, with many congeners displaying strong inhibitory effects against dengue virus (DENV) in cell-based assays. Following up on some literature reports, the rationale was borne out to preserve the pending groups, now attached to either a 2,6-diaminopurine or 2,4-diaminoquinazoline scaffold.

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