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In the title compound, C20H18ClN3, the cyclo­octene ring exhibits conformational disorder of two methyl­ene groups with a site-occupation factor of 0.859 (6) for the major occupied site. In the crystal, mol­ecules are connected into inversion dimers via pairs of weak N—H...N hydrogen bonds, forming an R22(12) graph-set motif. These dimers are further connected via weak N—H...Cl inter­actions into chains running along [011]. There are also C—H...N interactions present in the crystal.

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In the title compound, C21H20N2O, the piperidine ring adopts a chair conformation while the pyran ring adopts a screw-boat conformation. The piperidine ring forms dihedral angles of 65.75 (3) and 67.79 (5)° with the chroman and methyl-substituted benzene rings, respectively. The crystal structure features weak C—H...π and π–π [centroid–centroid distance = 3.8098 (8) Å] inter­actions.

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The title compound, C26H29N3O2, crystallizes with two mol­ecules in the asymmetric unit, having C—H...O inter­actions between them and resulting in a dimer characterized by an R22(11) motif. These dimers are linked into an ABABAB chain via N—H...O, N—H...N and C—H...O built edge-fused R12(5) and R22(7) motifs. This chain is linked to its inversion-related partner via N—H...O bonds with an R22(8) motif and leads to a double chain extending along the b axis characterized by an R66(36) motif across the inversion centres. The methyl group of the phenyl ring and the oxindole of mol­ecule A and B are involved in C—H...π inter­actions. One C atom of the pyrrolizine ring of mol­ecule A and its attached H atoms show positional disorder, the major and minor components being in the ratio 0.706 (7):0.294 (7).
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