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The title compound, C15H15NO4S, was obtained by the condensation of 4-amino­aceto­phenone and 4-meth­oxy­benzene­sulfonyl chloride. The dihedral angle between the benzene rings is 86.56 (9)° and the mol­ecule has an approximate V-shaped conformation. The C atom of the meth­oxy group is roughly coplanar with its attached ring [deviation = 0.177 (3) Å], as is the methyl C atom of the acetyl group with its ring [deviation = 0.065 (2) Å]. An intra­molecular C—H...O inter­action generates an S(6) ring. In the crystal, N—H...O and C—H...O hydrogen bonds link the mol­ecules into [010] chains. Weak C—H...π inter­actions are also observed.

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In the title mixed salt, 2C16H15N2+·C6H4ClO3S·NO3, one of the cations shows whole mol­ecule disorder over two sets of sites in a 0.711 (7):0.289 (7) ratio. The 4-chorobenzenesulfon­ate anion is also disordered over two orientations in a 0.503 (6):0.497 (6) ratio. The cations are close to planar, the dihedral angles between the pyridinium and indole rings being 1.48 (3)° in the ordered cation, and 5.62 (3) and 2.45 (3)°, respectively, for the major and minor components of the disordered cation. In the crystal, the cations are stacked in an anti­parallel manner approximately along the a-axis direction and linked with the anions via N—H...O hydrogen bonds and C—H...O inter­actions, generating a three-dimensional network. Weak C—H...π and π–π inter­actions [with centroid–centroid distances of 3.561 (2)–3.969 (7) Å] are also observed.

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In the structure of the title nicotino­nitrile derivative, C19H15N3O, the pyridine ring makes dihedral angles of 11.50 (7) and 43.36 (8)° with the 4-amino­phenyl and phenyl rings, respectively, and the dihedral angle between the phenyl rings is 36.28°. In the crystal, mol­ecules are linked by N—H...N hydrogen bonds into wave-like sheets parallel to (10-2). These sheets are stacked by π–π inter­actions between the 4-amino­phenyl rings of adjacent sheets, with centroid–centroid distances of 3.7499 (9) Å. C—H...π inter­actions are also present.

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The title salt crystallized as the monohydrate C15H16NO2+·C6H4BrSO3·H2O. The cation exists in an E conformation with respect to the ethynyl bond and is essentially planar, with a dihedral angle of 6.52 (14)° between the pyridinium and the benzene rings. The hy­droxy and meth­oxy substituents are coplanar with the benzene ring to which they are attached, with an r.m.s. deviation of 0.0116 (3) Å for the nine non-H atoms [Cmeth­yl—O—C—C torsion angle = −0.8 (4)°]. In the crystal, the cations and anions are stacked by π–π inter­actions, with centroid–centroid distances of 3.7818 (19) and 3.9004 (17) Å. The cations, anions and water mol­ecules are linked by O—H...O hydrogen bonds and weak C—H...O inter­actions, forming a three-dimensional network.
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