No abstract

The title Schiff base compound was synthesized via the condensation reaction of 1,2-di­amine­benzene with 4-benz­yloxy-2-hy­droxy­benzaldehyde. The mol­ecule is V-shaped and possesses mirror symmetry; the mirror bis­ects the central benzene ring. There are two intra­molecular O—H⋯N hydrogen bonds present forming S(6) ring motifs.

The title Schiff base compounds, (I) and (II), were synthesized via the condensation reaction of 2-amino-4-chloro­phenol for (I), and 2-(2,3-di­hydro-1H-indol-3-yl)ethan-1-amine for (II), with 4-benz­yloxy-2-hy­droxy­benzaldehyde. In both compounds, there is an intra­molecular hydrogen bond forming an S(6) ring motif; an O—H⋯O hydrogen bond in (I), but a charge-assisted N+—H⋯O− hydrogen bond in (II).

In the title compound, C20H16N2O4, the mol­ecule adopts an E conformation about the N=C bond. There is an intra­molecular O—H⋯N hydrogen bond forming an S(6) ring motif. The nitro­benzene and benz­yloxy rings are inclined to the central benzene ring by 4.34 (10) and 27.66 (11)°, respectively, and to one another by 31.40 (12)°. In the crystal, mol­ecules are linked via C—H⋯O hydrogen bonds, forming zigzag chains along [001]. Within the chains there are C—H⋯π inter­actions present. The chains are linked via π–π inter­actions [inter-centroid distance = 3.7048 (15) Å], forming slabs parallel to the bc plane.

Key indicatorsSingle-crystal X-ray study T = 293 K Mean '(C±C) = 0.005 A Ê R factor = 0.060 wR factor = 0.209 Data-to-parameter ratio = 21.4For details of how these key indicators were automatically derived from the article, see Figure 1 Molecular structure of (I). Displacement ellipsoids are shown at the 50% probability level.