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In the title compound, C21H20FN3O5, the the pyrrolidine ring makes dihedral angles of 84.91 (6) and 62.38 (7)° with the oxindole unit and the fluoro­phenyl ring, respectively. The pyrrolidine ring assumes an envelope conformation with the spiro C atom as the flap. The crystal packing features weak N—H...N and C—H...O hydrogen bonds.

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In the title compound, C13H18N2O4, the dihedral angle between the benzene and pyrrolidine (all atoms) rings is 70.6 (1)°. The pyrrolidine ring adopts a half-chair conformation. In the crystal, mol­ecules form chains along the c-axis direction linked by O—H...N hydrogen bonds, which are then connected by C—H...O inter­actions, forming a sheet parallel to the bc plane.

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In the crystal of the title molecular salt, C7H10N+·C6H5O4S, the benzene­sulfonate units are linked through phenol–sulfonate O—H...O hydrogen bonds, forming chains along the c-axis direction. These chains are linked via N—H...O hydrogen bonds involving two of the three H atoms of the ammonium group of the 4-methyl­anilium cation, giving rise to two-dimensional networks parallel to the bc plane which are further connected through an additional N—H...O inter­action in which the third ammonium H atom is involved, generating a three-dimensional network.

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The title salt, C5H6N3O2+·C2F3O2, crystallizes with two cations and two anions in the asymmetric unit. In the crystal, the acetate and pyridine groups are linked by a pair of N—H...O hydrogen bonds, forming loops described by the graph-set motif R22(8). These loops are linked via N—H...O hydrogen bonds, forming chains along [001]. The chains are in turn linked by C—H...O and C—H...F hydrogen bonds, generating a three-dimensional supra­molecular network. In both anions, the O and F atoms are disordered over two sites, with occupancy ratios of 0.852 (3):0.148 (3) and 0.851 (3):0.149 (3).

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In the title compound, C21H24ClNO, the piperidine ring adopts a chair conformation. The two phenyl rings are inclined to one another by 20.7 (1)°, and are inclined to the mean plane of the four planar atoms of the piperidine ring by 87.64 (10) and 70.8 (1)°. The mol­ecular structure features short intra­molecular C—H...Cl and C—H...O contacts. In the crystal, there are no significant inter­molecular inter­actions present.
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