Abstract

In the title compound, C24H15Cl2N3O2, one quinoline ring system is essentially planar and the other is slightly bent. An intra-molecular O-H⋯N hydrogen bond involving the hy-droxy group and a pyridine N atom forms an S(5) ring motif. In the crystal, two mol-ecules are associated into an inversion dimer with two R 2 2(7) ring motifs through inter-molecular O-H⋯N and O-H⋯O hydrogen bonds. The dimers are further linked by an inter-molecular C-H⋯O hydrogen bond and four C-H⋯π inter-actions, forming a two-dimensional network parallel to (001).

Highlights

  • In the title compound, C24H15Cl2N3O2, one quinoline ring system is essentially planar and the other is slightly bent

  • Two molecules are associated into an inversion dimer with two R22(7) ring motifs through intermolecular O—HÁ Á ÁN and O—HÁ Á ÁO hydrogen bonds

  • Molecules are linked by intermolecular O— HÁ Á ÁO and O—HÁ Á ÁN hydrogen bonds [O3—H3Á Á ÁO4i and O4—H4Á Á ÁN5i; symmetry code: (i) –x + 1, –y + 2, –z + 2], forming an inversion dimer with two R22(7) ring motifs (Fig. 2 and Table 1)

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Summary

Chemical context

8-Quinolinol and its derivatives are well-known chelating agents in analytical chemistry and bidentate ligands to metal ions in structural chemistry. Multinuclear metal complexes based on the dimeric 8-quinolinol ligand, 1,1-bis(8hydroxyquinolin-7-yl)ethane, have been investigated (Zhu et al, 2012; Zhang et al, 2014; Wu et al, 2017; Gao et al, 2018). On the other hand, Yamato et al (1986, 1987) reported the aromatic-group-substituted dimeric 8-quinolinol derivatives, 1,1-bis(8-hydroxyquinolin-7-yl)-1-(4-methoxyphenyl)methane, 1,1-bis(8-hydroxyquinolin-7-yl)-1-(furan-2-yl)methane and 1,1-bis(8-hydroxyquinolin-7-yl)-1-(thiophen-2-yl)methane, to be candidates for antitumor agents. We are attempting to develop a 2-pyridyl group-introduced dimeric 8-quinolinolbased ligand for mono- and multi-nuclear metal complexes, and report here the crystal structure of the title compound

Structural commentary
Supramolecular features
Database survey
Synthesis and crystallization
Refinement
Full Text
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