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In the title compound, C30H30Cl2N2O3, the indole ring system is roughly planar, with a maximum deviation of 0.1039 (18) Å for the carbonyl C atom, and makes a dihedral angle of 86.61 (9)° with the mean plane of the pyrrolidine ring. This spiro pyrrolidine ring adopts an envelope conformation with the N atom at the flap position. The pyrrole ring of the indole ring system adopts a twisted conformation on the C—C(=O) bond. The mol­ecular structure is stabilized by an intra­molecular C—H...O hydrogen bond, which generates an S(6) ring motif, and a π–π inter­action [centroid–centroid distance = 3.6577 (12) Å] involving the 2,4-di­chloro­phenyl ring and the benzyl ring. In the crystal, mol­ecules are linked via C—H...O hydrogen bonds, forming C(9) chains running parallel to [10-1].

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In the title compound, C29H29BrN2O3, the indole ring system is essentially planar (r.m.s. deviation = 0.079 Å) and makes a dihedral angle of 85.23 (10)° with the mean plane of the 4-methyl­pyrrolidine ring. This ring adopts an envelope conformation with the N atom at the flap. The pyrrolidine ring of the indole ring system adopts a twisted conformation on the C—C(=O) bond. The mol­ecular structure is stabilized by an intra­molecular C—H...O hydrogen bond, which generates an S(6) ring motif. In the crystal, mol­ecules are linked via pairs of C—H...O hydrogen bonds, forming inversion dimers with an R22(14) ring motif. These dimers are further linked by N—H...O and C—H...O hydrogen bonds, forming two-dimensional networks lying parallel to (10-1).

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In the title compound, C27H24Cl2N2O3, the indole ring system is essentially planar, with a maximum deviation of 0.082 (2) Å for the carbonyl C atom. It makes a dihedral angle of 88.53 (6)° with the mean plane of the 4-methyl­pyrrolidine ring, which adopts an envelope conformation with the N atom at the flap position. The mol­ecular structure is stabilized by intra­molecular C—H...O hydrogen bonds, which generate S(6) and S(7) ring motifs, and an intra­molecular π–π inter­action involving the benzyl and di­chloro-substituted benzene rings [centroid–centroid distance = 3.6291 (11) Å]. In the crystal, mol­ecules are linked via N—H...O hydrogen bonds, forming C(7) chains running parallel to [10-1].

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In the title solvate, C29H30N2O3·CHCl3, the dihedral angle between the indole ring system (r.m.s. deviation = 0.050 Å) and the 4-methyl­pyrrolidine ring is 88.88 (8)°. The latter ring adopts an envelope conformation with the N atom as the flap. Its mean plane makes dihedral angles of 86.94 (11) and 42.08 (9)° with the phenyl and di­methyl­benzene rings, respectively. The mol­ecular conformation is stabilized by intra­molecular C—H...O hydrogen bonds, which generate S(6) and S(9) ring motifs. The chloro­form solvent mol­ecule is linked to the organic mol­ecule by a C—H...O hydrogen bond involving the carbonyl O atom of the carboxyl­ate group. In the crystal, mol­ecules are linked via bifurcated N—H...(N,O) and C—H...O hydrogen bonds, forming chains propagating along [001].
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