Publication Date:
2017-05-05
Description:
In the title compounds,N-(5-acetyl-2-methylphenyl)quinoline-2-carboxamide [C19H16N2O2, (I)],N-(5-acetyl-2-bromophenyl)quinoline-2-carboxamide [C18H13BrN2O2, (II)] andN-(5-acetyl-2-ethynylphenyl)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 molecular structures of (I) and (III) each feature an intramolecular N—H...N hydrogen bond, forming anS(5) ring, while in (II) an intramolecular bifurcated N—H...(N,Br) hydrogen bond forms twoS(5) rings. In the crystals, weak C—H...O hydrogen bonds link molecules of (I) intoC(7) chains long [010], molecules of (II) into chains ofR22(8) rings along [110] and molecules of (III) intoC(8) chains along [010]. In (I), there are no significant π–π stacking interactions under 4 Å, but in both (II) and (III), π–π interactions 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)].
Electronic ISSN:
2056-9890
Topics:
Chemistry and Pharmacology
,
Geosciences
Permalink