The asymmetric unit of the title compound, C13H10N2O4, contains two independent mol­ecules (A and B). The dihedral angle between the aromatic rings is 48.18 (14)° in mol­ecule A and 45.81 (14)° in mol­ecule B. The mean plane of the carbamate N—C(=O)—O group is twisted slightly from the attached benzene and phenyl rings, making respective dihedral angles of 12.97 (13) and 60.93 (14)° in A, and 23.11 (14) and 59.10 (14)° in B. In the crystal, A and B mol­ecules are arranged alternately through N—H⋯O hydrogen bonds and C—H⋯π inter­actions, forming chains along the a axis. The chains are further linked by C—H⋯O hydrogen bonds into a double-chain structure.

The asymmetric unit of the title carbamate, contains two independent mol­ecules (A and B) with similar conformations. In the crystal, they are arranged alternately, forming –A–B–A–B– chains linked by N—H⋯O(carbon­yl) hydrogen bonds, which extend along the a-axis direction.

In the title compound, C22H14ClN3O2, the indole unit is essentially coplanar, with a maximum deviation of 0.035 Å for the C atom bearing the methyl group. The central pyridine ring is inclined to the indole ring system by 43.7 (1)°. The dihedral angle between the phenyl ring and the indole ring system is 15.7 (2)°, while that between the phenyl ring and the central pyridine ring is 46.3 (1)°. The mol­ecular structure is stabilized by an intra­molecular O—H⋯O hydrogen bonding, forming an S(6) ring motif. In the crystal, mol­ecules are linked via pairs of N—H⋯N hydrogen bonds, forming inversion dimers with an R 2 2(16) ring motif. The crystal structure also features C—H⋯π and π–π inter­actions [centroid–centroid separation = 3.688 (1) Å].

In the title compound, C18H14N2O2, the six-membered oxazine ring adopts a half-chair conformation and its mean plane makes a dihedral angle of 83.23 (7)° with the pyrrolidine ring of the indoline ring system. In the crystal, mol­ecules are linked via N—H⋯O hydrogen bonds, forming chains along [100]. The chains are linked by C—H⋯π inter­actions, forming slabs parallel to (001).

In the racemic title compound, C20H16N2O5, the pyran ring adopts a shallow envelope conformation, with the stereogenic C atom displaced from the other atoms by 0.273 (2) Å. The dihedral angle between the fused-ring system and the pendant p-tolyl group is 87.62 (7)°. The mol­ecular conformation is consolidated by an intra­molecular N—H⋯O hydrogen bond, which generates an S(6) ring. In the crystal, mol­ecules are linked by C—H⋯O inter­actions, resulting in [010] chains.