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In the title compound, C28H27FN4O3·H2O, the benzimidazole ring system is essentially planar with a maximum deviation of 0.028 (1) Å. It makes dihedral angles of 47.59 (5) and 60.31 (5)°, respectively, with the pyridine and benzene rings, which make a dihedral angle of 22.58 (6)° with each other. The pyrrolidine ring shows an envelope conformation with one of the methyl­ene C atoms as the flap. In the crystal, the components are connected into a tape along the b-axis direction through O—H...O and O—H...N hydrogen bonds and a π–π inter­action between the pyridine and benzene rings [centroid–centroid distance of 3.685 (8) Å]. The tapes are further linked into layers parallel to the ab plane by C—H...O and C—H...F inter­actions.

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In the title mol­ecule, C23H22N2OS, the di­phenyl­acetyl and ethyl­benzene groups adopt a transcis conformation, respectively, with respect to the S atom across the (S=)C—N bonds. This conformation is stabilized by an intra­molecular N—H...O hydrogen bond and a weak C—H...S hydrogen bond. The ethyl-substituted benzene ring forms dihedral angles of 87.53 (15) and 73.94 (15)° with the phenyl rings. In the crystal, N—H...O hydrogen bonds link mol­ecules into chains along [100]. A weak C—H...π inter­action is also observed.

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In the 3-hy­droxy­picolinate anion of the title salt, C6H9N2+·C6H4NO3, an intra­molecular O—H...O hydrogen bond with an S(6) graph-set motif is formed, so that the anion is essentially planar, with a dihedral angle of 9.55 (9)° between the pyridine ring and the carboxyl­ate group. In the crystal, the cations and anions are linked via N—H...O hydrogen bonds, forming a centrosymmetric 2 + 2 aggregate with R22(8) and R42(8) ring motifs. The crystal structure also features N—H...N and weak C—H...π inter­actions.

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In the title salt, C6H9N2+·C7H5O3, the anion is essentially planar, with a dihedral angle of 2.72 (17)° between the benzene ring and the carboxyl­ate group. In the crystal, the anions are connected by O—H...O hydrogen bonds, forming a 41 helical chain along the c axis. 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 another N—H...O hydrogen bond, resulting in a three-dimensional network.
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