Crystal structures of three N-(3-acetyl-phen-yl)quinoline-2-carboxamides.

ABSTRACT: In the title compounds, N-(5-acetyl-2-methyl-phen-yl)quinoline-2-carboxamide [C₁₉H₁₆N₂O₂, (I)], N-(5-acetyl-2-bromo-phen-yl)quinoline-2-carboxamide [C₁₈H₁₃BrN₂O₂, (II)] and N-(5-acetyl-2-ethynylphen-yl)quinoline-2-carboxamide [C₂₀H₁₄N₂O₂, (III)], the quinoline ring system is essentially planar and forms a dihedral angles of 3.68?(5) (I), 5.59?(7) (II) and 1.87?(6)° (III) with the acetyl-substituted ring. The mol-ecular structures of (I) and (III) each feature an intra-molecular N-H?N hydrogen bond, forming an S(5) ring, while in (II) an intra-molecular bifurcated N-H?(N,Br) hydrogen bond forms two S(5) rings. In the crystals, weak C-H?O hydrogen bonds link mol-ecules of (I) into C(7) chains long [010], mol-ecules of (II) into chains of R₂²(8) rings along [110] and mol-ecules of (III) into C(8) chains along [010]. In (I), there are no significant ?-? stacking inter-actions under 4?Å, but in both (II) and (III), ?-? inter-actions link the weak hydrogen-bonded chains into layers parallel to (001) [centroid-centroid disttances of 3.748?(1)?Å in (II) and 3.577?(1), 3.784?(1) and 3.780?(1)?Å in (III)].

SUBMITTER: Pena-Solorzano D 

PROVIDER: S-EPMC5458296 | biostudies-literature | 2017 Jun

REPOSITORIES: biostudies-literature