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The title compound, C23H18N2O4S2, contains a pyrrolo group fused onto the plane of an indole ring with phenylsulfonyl and p-toluenesulfonyl groups bonded to the indole and pyrrolo rings. The angles between the mean planes of the pyrrolo-indole ring and the phenylsulfonyl and p-toluenesulfonyl rings are 73.7 (6) and 80.6 (0)°, respectively. The dihedral angle between the mean planes of the two benzene rings is 78.7 (4)°. In the crystal, both classical N—H...O and non-classical C—H...O intermolecular hydrogen-bonding interactions are observed, as well as weak π–π interactions [centroid–centroid distances = 3.6258 (8) and 3.9298 (8) Å], which contribute to the stability of the packing.

In the title compound, C14H15BrN2O, the pyrrolidine ring adopts a twist conformation. The amide group is twisted out of π-conjugation with the pyrrole double bond due to steric hindrance by the Br atom.

The crystal structure of the title compound, C16H19BrN2O, reveals that the amide group is twisted out of π-conjugation with the indole double bond due to steric hindrance by the Br atom. The azepane ring adopts a twist-chair conformation.

The crystal structure of the title compound, C15H19BrN2O, reveals that the amide group is twisted out of π-conjugation with the pyrrole double bond due to steric hindrance by the Br atom.

The title compound, C5H18N2O, reveals a cis–trans stereochemistry for this rare example of the 5H-indolizino[1,2-b]indole ring system.

Hexahydropyrrolo[3,4-b]indoles 6, 10, and 13 are obtained from 2-bromo-3-carboxamides 5, 9, and 12, respectively, by a 1,5-radical translocation process followed by 5-endo-trig cyclization to the indole C-2 position.