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In the title compound, C20H27N3O, the hy­droxy group forms an intra­molecular O—H...N hydrogen bond with the imino N atom. The dihedral angle between the aromatic rings is 33.09 (9)°. In the crystal, mol­ecules form centrosymmetric dimers via pairs of N—H...N hydrogen bonds involving amino­pyridine fragments.

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In the title compound, C25H23N·CHCl3, the dihydro­anthracene unit is bent with a dihedral angle between the benzene rings of 57.82 (8)°. The N atom of the pyrrolidine heterocycle, which has an envelope conformation with the N atom as the flap, exhibits a pronounced pyramidalization [Σ(C—N—C) = 328.07°], indicating an accentuated N-donor character. In the crystal, this behaviour is evident by the C—H...N hydrogen bond involving a solvent mol­ecule and the N atom. The absolute configuration at the C-atom fused positions of the pyrrolidine group were crystallographically confirmed to be S and R.

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The fused five- and six-membered rings in the title mol­ecule, C10H9N3O2, are essentially coplanar, the largest deviation from the mean plane being 0.012 (1) Å for the C atom linked to the nitro group. The fused-ring system makes a dihedral angle of 11.34 (6)° with the nitro group, leading to a syn-periplanar conformation. The plane through the atoms forming the allyl group is nearly perpendicular to the indazole fused-ring system, as indicated by the dihedral angle of 73.3 (5)°. In the crystal, each mol­ecule is linked to its symmetry equivalent about the center of inversion by pairs of non-classical C—H...O hydrogen bonds, forming an extended tape motif parallel to the (-12-1) plane.
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