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Structural and theoretical study of (4E,5Z)‐4,5‐dibenzylidene‐1,2,3,6,7,8‐hexahydroacridine
Author(s) -
Tkachev Valeriy V.,
Utenyshev Andrey N.,
Kovalchukova Olga V.
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202003477
Subject(s) - intramolecular force , intermolecular force , dihedral angle , molecule , chemistry , crystallography , atoms in molecules , density functional theory , crystal (programming language) , covalent bond , electron density , ring (chemistry) , crystal structure , computational chemistry , hydrogen bond , stereochemistry , electron , organic chemistry , physics , quantum mechanics , computer science , programming language
The crystal and molecular structure of (4E,5Z)‐4,5‐dibenzylidene‐1,2,3,6,7,8‐hexahydroacridine as a biologically active substance with potential antioxidant, anti‐inflammatory and anti‐microbial activity is reported. The title compound is found to be non‐planar. The rings are twisted around the central fragment of the molecule by 54.0 and 32.5°. The dihedral angle between the two phenyl rings is 23°. In crystal, the molecules are packed in head‐to‐head stacks along the b ‐axis with no intermolecular H‐bonds. DFT B3LYP theoretical modeling with the LANL2DZ basis is performed and a topological analysis of the electron density distribution is carried out in the framework of the Bader QTAIM theory for both isolated molecules and dimeric associates forming stacks in the crystal. It is found that some intermolecular and intramolecular non‐valent interactions are to some extent related to the formation of weak covalent interactions in the intermolecular and intramolecular space.