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In the title compound, C31H25N5O3·C2H6OS, the three indole/indoline units are all essentially planar with maximum deviations of 0.0172 (3), 0.053 (2) and 0.07 (2) Å. The pyrrolidine ring adopts an envelope conformation with the C atoms bearing the 1-ethyl-2-oxo­indole substituent (in which the five-membered ring adopts a twisted conformation) as the flap. The dimethyl sulfoxide solvent mol­ecule is disordered over two positions, with an occupancy factor ratio of 0.871 (4):0.129 (4). The solvent components are linked to the heterocyclic mol­ecule via C—H...O and C—H...S hydrogen bonds. In the crystal, the solvent components are linked to the heterocyclic molecule via C—H...O and C—H...S inter­actions, forming R22(10) ring motifs. The mol­ecules are further connected into a chain along the a-axis direction via N—H...O hydrogen bonds.

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In the title compound, C25H20N6O2·0.15H2O, the dihedral angles between the least-squares planes of the indole and pyrrolidine rings and between the oxindole and imidazole rings are 77.66 (7) and 45.31 (7)°, respectively. The pyrrolidine ring and the fused five-membered pyrrolidine ring of the oxindole moiety exhibit twisted conformations. The amide N atom is involved in both intra- and inter­molecular hydrogen bonding, having a bifurcated character. The mol­ecular structure is characterized by an intra­molecular N—H...O hydrogen bond, which generates an S(7) ring motif while an inter­molecular N—H...O hydrogen bond links the organic and solvent water mol­ecules. In the crystal, N—H...N hydrogen bonds generate a zigzag chain running parallel to c-axis direction. The H atoms of the solvent water mol­ecule were not located.

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In the title compound, C26H20N4O2S, the central pyrrolidine ring adopts a twist conformation on the C—C bond involving the spiro C atom. Its mean plane makes dihedral angles of 78.83 (14), 65.91 (15) and 44.49 (18)° with the mean planes of the adjacent oxindole ring system, the indole system and the thio­phene ring, respectively. The indole and indoline units are essentially planar, with maximum deviations of 0.019 (3) and 0.090 (3) Å, respectively. In the oxindole fused-ring system, the pyrrole ring adopts an envelope conformation with the spiro C atom as the flap. In the crystal, pairs of N—H...O hydrogen bonds link the mol­ecules, forming inversion dimers with an R22(8) ring motif. The dimers are linked by further N—H...O hydrogen bonds, forming a two-dimensional network lying parallel to (100).

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In the title compound, C19H19N5, the piperidine ring adopts a chair conformation. The pyridine ring is essentially planar, with a maximum deviation of 0.039 (2) Å for a C atom substituted with a carbonitrile group. The mean plane of the central pyridine ring makes the dihedral angles of 37.90 (14) and 56.10 (12)° with the piperidine and benzene rings, respectively. In the crystal, mol­ecules are linked via N—H...N and C—H...N hydrogen bonds, forming chains along [101], and enclosing R22(17) ring motifs. The chains are linked by further C—H...N hydrogen bonds, forming two-dimensional networks lying parallel to (10-1), and enclosing inversion dimers with R22(20) ring motifs.
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