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In the inner-salt zwitterion of 3,6-bis­(pyridin-2-yl)pyrazine-2,5-dicarb­oxy­lic acid, (I), namely 5-carb­oxy-3-(pyridin-1-ium-2-yl)-6-(pyridin-2-yl)pyrazine-2-carboxyl­ate, [C16H10N4O4, (Ia)], the pyrazine ring has a twist–boat conformation. The opposing pyridine and pyridinium rings are almost perpendicular to one another, with a dihedral angle of 80.24 (18)°, and are inclined to the pyrazine mean plane by 36.83 (17) and 43.74 (17)°, respectively. The carb­oxy and carboxyl­ate groups are inclined to the mean plane of the pyrazine ring by 43.60 (17) and 45.46 (17)°, respectively. In the crystal structure, the mol­ecules are linked via N—H...O and O—H...O hydrogen bonds, leading to the formation of double-stranded chains propagating in the [010] direction. On treating (Ia) with aqueous 1 M HCl, the diprotonated dihydrate form 2,2′-(3,6-dicar­boxy­pyrazine-2,5-di­yl)bis­(pyridin-1-ium) dichloride dihydrate [C16H12N4O42+·2Cl·2H2O, (Ib)] was obtained. The cation lies about an inversion centre. The pyridinium rings and carb­oxy groups are inclined to the planar pyrazine ring by 55.53 (9) and 19.8 (2)°, respectively. In the crystal structure, the mol­ecules are involved in N—H...Cl, O—H...Owater and Owater—H...Cl hydrogen bonds, leading to the formation of chains propagating in the [010] direction. When (Ia) was recrystallized from dimethyl sulfoxide (DMSO), the DMSO disolvate 3,6-bis­(pyridin-2-yl)pyrazine-2,5-dicarb­oxy­lic acid dimethyl sulfoxide disolvate [C16H10N4O4·2C2H6OS, (Ic)] of (I) was obtained. Here, the mol­ecule of (I) lies about an inversion centre and the pyridine rings are inclined to the planar pyrazine ring by only 23.59 (12)°. However, the carb­oxy groups are inclined to the pyrazine ring by 69.0 (3)°. In the crystal structure, the carb­oxy groups are linked to the DMSO mol­ecules by O—H...O hydrogen bonds. In all three crystal structures, the presence of nonclassical hydrogen bonds gives rise to the formation of three-dimensional supra­molecular architectures.
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