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The quinoline ring system of the title salt, C11H12NO+·HSO4, is essentially planar, with a maximum deviation of 0.054 (2) Å for all non H atoms. In the crystal, the cations and anions are linked via N—H...O, O—H...O and weak C—H...O hydrogen bonds, and are stacked respectively in columns along the a axis. π–π stacking inter­actions, with centroid–centroid distances of 3.5473 (12) and 3.6926 (12) Å, are also observed. The crystal studied was an inversion twin with refined components of 0.43 (7):0.57 (7).

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In the title hydrated salt, C11H12NO+·Cl·2H2O, the quinoline ring system is essentially planar, with a maximum deviation of 0.005 (1) Å for all non-H atoms. In the crystal, the three components are linked by O—H...O, N—H...O, O—H...Cl and weak C—H...O hydrogen bonds, forming a layer structure parallel to the ac plane. The crystal structure is further stabilized by π–π stacking inter­actions, with centroid–centroid distances of 3.5213 (6) and 3.7176 (6) Å.

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In the title mol­ecular salt, C5H8N3+·C3H3O4, the cation is essentially planar, with a maximum deviation of 0.005 (1) Å for all non-H atoms. In the anion, an intra­molecular O—H...O hydrogen bond generates an S(6) ring. In the crystal, the cations and anions are connected via N—H...O hydrogen bonds and a weak C—H...O inter­action, forming layers parallel to the ab plane.

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The 4-methyl­benzoate anion of the title salt, C6H9N2+·C8H7O2, is nearly planar, with a dihedral angle of 6.26 (10)° between the benzene ring and the carboxyl­ate group. In the crystal, the protonated N atom and the 2-amino group of the cation are hydrogen bonded to the carboxyl­ate O atoms of the anion via a pair of N—H...O hydrogen bonds with an R22(8) ring motif, forming an approximately planar ion pair with a dihedral angle of 9.63 (4)° between the pyridinium and benzene rings. The ion pairs are further connected via N—H...O and weak C—H...O hydrogen bonds, forming a two-dimensional network parallel to the bc plane.

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In the 5-chloro­salicylate anion of the title salt, C6H9N2+·C7H4ClO3, an intra­molecular O—H...O hydrogen bond with an S(6) graph-set motif is observed and the dihedral angle between the benzene ring and the –CO2 group is 1.6 (6)°. In the crystal, the protonated N atom and the 2-amino group of the cation are hydrogen bonded to the carboxyl­ate O atoms via a pair of N—H...O hydrogen bonds, forming an R22(8) ring motif. The crystal structure also features N—H...O and weak C—H...O inter­actions, resulting in a layer parallel to (10-1).

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The 4-chloro­benzoate anion of the title salt, C6H9N2+·C7H4ClO2, is nearly planar with a dihedral angle of 5.14 (16)° between the benzene ring and the carboxyl­ate group. In the crystal, the protonated N atom and the 2-amino group of the cation are hydrogen bonded to the carboxyl­ate O atoms of the anion via a pair of N—H...O hydrogen bonds with an R22(8) ring motif. The ion pairs are further connected via N—H...O and weak C—H...O hydrogen bonds, forming a two-dimensional network parallel to the bc plane. The crystal structure also features a π–π stacking inter­action between the pyridinium and benzene rings with a centroid–centroid distance of 3.7948 (9) Å.
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