Acta Crystallographica Section C

Crystal Structure Communications

Volume 68, Part 11 (November 2012)


organic compounds



fg3272 scheme

Acta Cryst. (2012). C68, o431-o435    [ doi:10.1107/S0108270112039534 ]

The inner-salt zwitterion, the dihydrochloride dihydrate and the dimethyl sulfoxide disolvate of 3,6-bis(pyridin-2-yl)pyrazine-2,5-dicarboxylic acid

Y. Wang and H. Stoeckli-Evans

Abstract: 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.

Formula: C16H10N4O4 and ·2C2H6OS, and C16H12N4O42+·2Cl-·2H2O


hkldisplay filedownload file

Structure factor file (CIF format) (116.6 kbytes)
[ doi:10.1107/S0108270112039534/fg3272Iasup2.hkl ]
Contains datablock Ia


hkldisplay filedownload file

Structure factor file (CIF format) (82.8 kbytes)
[ doi:10.1107/S0108270112039534/fg3272Ibsup3.hkl ]
Contains datablock Ib


hkldisplay filedownload file

Structure factor file (CIF format) (97.4 kbytes)
[ doi:10.1107/S0108270112039534/fg3272Icsup4.hkl ]
Contains datablock Ic


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