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The mol­ecule of the title compound, C21H17N3O, is built up from fused five- and six-membered rings connected to a methyl group, a phenyl ring and an (imino­meth­yl)phenol group. The fused ring system is almost planar (r.m.s. deviation = 0.031 Å) and forms dihedral angles of 64.97 (7) and 18.52 (6)° with the phenyl ring and the (imino­meth­yl)phenol group, respectively. In the crystal, centrosymmetric mol­ecules are linked by pairs of C—H⋯π inter­actions into dimeric units, which are further connected by O–H⋯N hydrogen bonds to form layers parallel to (101).

In the title compound, C9H10N2O, the imidazo[1,2-a]pyridine moiety is approximately planar (r.m.s. deviation = 0.024 Å). The methanol group is nearly perpendicular to its mean plane as indicated by the C—C—C—O and N—C—C—O torsion angles of 80.04 (16) and −96.30 (17)°, respectively. In the crystal, mol­ecules are linked by O—H⋯N hydrogen bonds, forming inversion dimers with an R 2 2(10) ring motif. The dimers are liked via C—H⋯O hydrogen bonds, enclosing R 2 2(10) ring motifs and forming ribbons along [201]. The ribbons are linked via a number of π–π inter­actions [centroid–centroid distances vary from 3.4819 (8) to 3.7212 (8) Å], forming a three-dimensional structure.

In the title compound, C15H11N3O4, the imidazo[1,2-a] pyridine ring system is almost planar [r.m.s. deviation = 0.028 (2) Å]. Its mean plane makes dihedral angles of 33.92 (7) and 34.56 (6)° with the meth­oxy­phenyl ring and the nitro group, respectively. The cohesion of the crystal structure is ensured by C—H⋯N and C—H⋯O hydrogen bonds, forming layers almost parallel to the ac plane.