Synthesis by deamination reaction and crystal structure at 120 K of (16 Z,19 E)-18-oxo- N -(pyridin-2-yl)-6,7,9,10-tetra­hydro-18 H -dibenzo[ h, o ][1,4,7]trioxa­cyclo­hexa­decine-17-carboxamide

The title compound, C 27 H 24 N 2 O 5, is a product of the deamination reaction from aza-14-crown-4 ether containing the γ-piperidone subunit. The title mol­ecule contains a 16-membered macrocycle with the conformation of the C - O - C - C - O - C - C - O - C polyether chain being t-g (-) -t-t-g (+) -t (t = trans, 180°; g = gauche, ±60°). The dihedral angle between the planes of the benzene rings fused to the aza-14-crown-4-ether moiety is 31.11 (14)°. The cavity size inside the macrocycle is 4.72 Å. The macrocycle is significantly flattened as a result of the extended conjugated system. Steric repulsion between the pyridyl­carboxamide fragment and the benzene ring results in a slight deviation of macrocycle from planarity. The structure also features intra­molecular hydrogen bonding, which results in a deviation of the angle between the planes of amide and pyridyl groups from planarity: this angle is 16.32 (18)°. In the crystal, the mol­ecules are linked into infinite zigzag chains via inter­molecular C - H⋯π contacts. The chains are bound into layers parallel to (100) by weak inter­molecular C - H⋯O hydrogen bonds. © 2020 International Union of Crystallography. All rights reserved.

International Union of Crystallography
  • 1 College of Natural and Computational Sciences, University of Gondar, Gondar, 196, Ethiopia
  • 2 Faculty of Chemistry, VNU University of Science, Vietnam National University, Hanoi, 334 Nguyen Trai, Thanh Xuan, Hanoi, Viet Nam
  • 3 Inorganic Chemistry Department, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklay St., Moscow, 117198, Russian Federation
  • 4 N. N. Semenov Federal Research Center, for Chemical Physics, Russian Academy of Sciences, Ul. Kosygina 4, Moscow, Russian Federation
  • 5 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp., Moscow, 119991, Russian Federation
Ключевые слова
aza-crown ether; C - H⋯π contacts; crystal structure; deamination reaction; dibenzo-16-crown-3; hydrogen bonds; γ-piperidone
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