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-tetra-hydro-18 H -dibenzo[ h , o ][1,4,7]trioxa-cyclo-hexa-decine-17-carboxamide.

Autor: Wodajo AT; College of Natural and Computational Sciences, University of Gondar, 196 Gondar, Ethiopia., Tran TTV; Faculty of Chemistry, VNU University of Science, Vietnam National University, Hanoi, 334 Nguyen Trai, Thanh Xuan, Hanoi, Vietnam., Truong HH; Inorganic Chemistry Department, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklay St., Moscow 117198, Russian Federation., Tskhovrebov AG; Inorganic Chemistry Department, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklay St., Moscow 117198, Russian Federation.; N. N. Semenov Federal Research Center, for Chemical Physics, Russian Academy of Sciences, Ul. Kosygina 4, Moscow, Russian Federation., Le TD; Faculty of Chemistry, VNU University of Science, Vietnam National University, Hanoi, 334 Nguyen Trai, Thanh Xuan, Hanoi, Vietnam., Khrustalev VN; Inorganic Chemistry Department, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklay St., Moscow 117198, Russian Federation.; N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp., Moscow 119991, Russian Federation., Le TA; Faculty of Chemistry, VNU University of Science, Vietnam National University, Hanoi, 334 Nguyen Trai, Thanh Xuan, Hanoi, Vietnam.
Jazyk: angličtina
Zdroj: Acta crystallographica. Section E, Crystallographic communications [Acta Crystallogr E Crystallogr Commun] 2020 Aug 14; Vol. 76 (Pt 9), pp. 1454-1457. Date of Electronic Publication: 2020 Aug 14 (Print Publication: 2020).
DOI: 10.1107/S2056989020010968
Abstrakt: 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 mol-ecule 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 pyridyl-carboxamide fragment and the benzene ring results in a slight deviation of macrocycle from planarity. The structure also features intra-molecular 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 mol-ecules are linked into infinite zigzag chains via inter-molecular C-H⋯π contacts. The chains are bound into layers parallel to (100) by weak inter-molecular C-H⋯O hydrogen bonds.
(© Wodajo et al. 2020.)
Databáze: MEDLINE
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