(2-Hydroxyphenyl)(4,2′:4′,4′′-terpyridin-6′-yl)methanone

The crystal structure of the title compound exhibits an intramolecular O—H⋯O hydrogen bond and is consolidated by C—H⋯O and C—H⋯N hydrogen-bonding interactions.

The title compound, C 22 H 15 N 3 O 2 , can be described as a ketone with a phenol substituent and a terpyridine ligand coordinated to the carbonyl group. The three six-membered rings of the terpyridine ligand are not coplanar. The dihedral angles between the mean planes of the central ring and the external pyridine ligands are 22.77 (9) and 26.77 (7) . The central ring of the terpyridine ligand is also not coplanar with the o-hydroxy phenyl ring, the dihedral angle being 39.72 (5) . An intramolecular O-HÁ Á ÁO hydrogen bond occurs. The crystal structure of the title compound is consolidated by C-HÁ Á ÁO and C-HÁ Á ÁN hydrogen bonding interactions.

Structure description
Pyridine and derivatives play critical roles in the biochemical field. The hydrazone derivatives of benzoylpyridines exhibit cytotoxic activity towards tumor cell lines (Santos et al., 2018) and show excellent antiproliferative activity (Kalinowski et al., 2007). The quest for an efficient method for the preparation of such pyridine derivatives is ongoing. Herein, we report a novel method for the preparation of a 2-benzoylpyridine derivative in a one-pot reaction of 3-aminocoumarin with 4-acetylpyridine. The structural elucidation of the compound by spectroscopic investigation and single-crystal analysis has been performed.
The molecular structure of the title compound is shown in Fig. 1. It crystallizes in the orthorhombic crystal system in P2 1 2 1 2 1 space group with one molecule in the asymmetric unit. The compound can be described as a ketone with a phenol substituent and a terpyridine ligand coordinated to the carbonyl group. The dihedral angle between the mean planes of the central ring of the terpyridine ligand and the o-hydroxy phenyl ring is data reports 39.72 (5) . The three six-membered rings of the terpyridine ligand are not coplanar. The dihedral angles between the mean planes of the central ring and the external pyridine ligands are 22.77 (9) and 26.77 (7) (for C13-C17/N2 and C18-C22/N3, respectively). A strong intramolecular O-HÁ Á ÁO hydrogen bond (O2-H2 0 Á Á ÁO1) exists between the O1 and O2 atoms of the phenol ring (Table 1).

Figure 1
The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.

Figure 4
Unit-cell packing depicting the intermolecularstacking interactions as dotted lines. where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.001 Δρ max = 0.18 e Å −3 Δρ min = −0.23 e Å −3 Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. Refinement. The hydroxy H atom was located in the Fourier maps and freyly refined, while all other H atoms were fixed geometrically and allow to ride on their parent carbon atoms, with a C-H distance of 0.95 Å and U iso (H) = 1.2U eq (C).