1-[6-(1H-Indol-1-yl)pyridin-2-yl]-1H-indole-3-carbaldehyde.

In the title compound, C22H15N3O, the dihedral angle between the two indole units is 33.72 (3)°. The mol-ecular structure features a weak intra-molecular C-H⋯N inter-action. In the crystal, weak C-H⋯O and C-H⋯π inter-actions, forming a two-dimensional network parallel to the bc plane.

9-[4-(Azido-meth-yl)phen-yl]-9H-carbazole-3-carbo-nitrile.

In the title compound C20H13N5, the dihedral angle between the carbazole ring system (r.m.s. deviation = 0.027 Å) and the pendant benzene ring is 55.08 (6)°. One of the azide N atoms is disordered over two positions in a 0.65 (2):0.35 (2) ratio. In the crystal, aromatic π-π stacking is observed [minimum centroid-centroid separation = 3.6499 (13) Å] as well as inversion-dimers connected by pairs of weak C-H⋯π inter-actions.

2-Bromo-1-(1-phenyl-sulfonyl-1H-indol-3-yl)propan-1-one.

In the title compound, C17H14BrNO3S, the phenyl ring makes a dihedral angle of 89.78 (16)° with the plane of the indole ring system. The terminal Br atom and the methyl group are disordered over two sets of sites, with site occupancies of 0.860 (2) and 0.140 (2). In the crystal, mol-ecules are linked into a chain along the b-axis direction by weak C-H⋯O hydrogen bonds. The chains are further linked by C-H⋯π inter-actions, forming layers parallel to the bc plane.

2-Methyl-1-phenyl-sulfonyl-1H-indole-3-carbaldehyde.

In the title compound, C(16)H(13)NO(3)S, the sulfonyl-bound phenyl ring forms a dihedral angle of 84.17 (6)° with the indole ring system. An intra-molecular C-H⋯O hydrogen bond generates an S(6) ring motif. The crystal structure exhibits weak inter-molecular C-H⋯O hydrogen bonds and π-π inter-actions between the five- and six-membered rings of the indole group [centroid-centroid distance = 3.6871 (9) Å].

9-p-Tolyl-9H-carbazole-3-carbonitrile.

In the title compound, C(20)H(14)N(2), the carbazole ring system is essentially planar (r.m.s. deviation = 0.187 Å) and is inclined at an angle of 54.33 (4) ° with respect to the benzene ring. The crystal packing is stabilized by weak C-H⋯N and C-H⋯π inter-actions.

Ethyl 1-phenyl-sulfonyl-1H-indole-2-carboxyl-ate.

In the title compound, C(17)H(15)NO(4)S, the six-membered ring of the indole unit makes a dihedral angle of 72.40 (5)° with the phenyl ring. The mol-ecular structure features a short C-H⋯O contact.

3-Iodo-2-methyl-1-phenyl-sulfonyl-1H-indole.

In the title compound, C(15)H(12)INO(2)S, the sulfonyl-bound phenyl ring forms a dihedral angle 82.84 (9)° with the indole ring system. The mol-ecular structure is stabilized by a weak intra-molecular C-H⋯O hydrogen bond. The crystal structure exhibits weak inter-molecular C-H⋯π inter-actions and π-π inter-actions between the indole groups [centroid-centroid distance between the five-membered and six-membered rings of the indole group = 3.7617 (18) Å].

Ethyl 1-benzene-sulfonyl-2-[(E)-2-(2-methyl-phen-yl)ethen-yl]indole-3-carboxyl-ate.

In the title compound, C(26)H(23)NO(4)S, the phenyl, tolyl and ester groups make dihedral angles of 82.28 (5), 77.67 (6) and 8.52 (6)°, respectively, with the indole ring system. The S atom of the sulfonyl group is displaced by 0.1968 (4) Šfrom the indole mean plane. The mol-ecular structure is stabilized by weak intra-molecular C-H⋯O inter-actions. The crystal structure structure features short intramolecular C-H⋯O contacts and π-π stacking inter-actions between the phenyl and tolyl groups [centroid-centroid distance = 3.9448 (11) Å].