Crystal structure, Hirshfeld surface analysis and DFT studies of 2-(2,3-dihydro-1H-perimidin-2-yl)phenol

Acta Crystallographica Section E: Crystallographic Communications

Tuncer Hökelek¹  Pascal Retailleau²  Ballo Daouda³  El Mokhtar Essassi³  Niameke Jean-Baptiste Kangah⁴  Nanou Tiéba Tuo⁴  Charles Guillaume Kodjo⁴ 

[1] Department of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey;Institut de Chimie des Substances Naturelles, 1 av. de la Terrasse, 91198 Gif sur Yvette, France;Laboratoire de Chimie Organique Heterocyclique URAC 21, Pôle de Competence Pharmacochimie, Faculté des Sciences, Université Mohammed V, Rabat, Morocco;Laboratoire de Thermodynamique et Physicochimie du Milieu, Université Nangui, Abrogoua, UFR-SFA, 02 BP 801 Abidjan 02, Côte d'Ivoire;

关键词: crystal structure;    perimidine;    phenol;    hirshfeld surface;   

DOI  :  10.1107/S2056989020005939

来源: DOAJ

【 摘 要 】

The asymmetric unit of the title compound, C17H14N2O, contains two independent molecules each consisting of perimidine and phenol units. The tricyclic perimidine units contain naphthalene ring systems and non-planar C4N2 rings adopting envelope conformations with the C atoms of the NCN groups hinged by 44.11 (7) and 48.50 (6)° with respect to the best planes of the other five atoms. Intramolecular O—H...N hydrogen bonds may help to consolidate the molecular conformations. The two independent molecules are linked through an N—H...O hydrogen bond. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (52.9%) and H...C/C...H (39.5%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Density functional theory (DFT) optimized structures at the B3LYP/ 6–311 G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

【 授权许可】

Unknown