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Updated: Jun 1, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
N-[2-(4-Methyl-2-quinol-yl)phen-yl]acetamide: a P1 structure with Z = 4
Abstract:
The title compound, C(18)H(16)N(2)O, crystallizes in the triclinic space group P1, with four independent mol-ecules in the asymmetric unit wherein two mol-ecules have an irregular -ac, -ac, +ap conformation (ap, antiperiplanar; ac, anticlinal), while the other mol-ecules exhibit a different, +ac, +ac, +ap conformation. The planar (r.m.s. deviation = 0.006 Å in each of the four molecules) quinoline ring systems of the four mol-ecules are oriented at dihedral angles of 32.8 (2), 33.4 (2), 31.7 (2) and 32.3 (2)° with respect to the benzene rings. Intra-molecular N-H⋯N inter-actions occur in all four independent mol-ecules. The crystal packing is stabilized by inter-molecular N-H⋯O and C-H⋯O hydrogen bonds, and are further consolidated by C-H⋯π and π-π stacking inter-actions [centroid-centroid distances = 3.728 (3), 3.722 (3), 3.758 (3) and 3.705 (3) Å].
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