Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 2-(2,3-dihydro-1H-perimidin-2-yl)-6-methoxyphenol

Acta Crystallographica Section E: Crystallographic Communications

Tuncer Hökelek¹  Ballo Daouda²  El Mokhtar Essassi²  Nanou Tiéba Tuo³  Kodjo Charles Guillaume⁴  Kangah Niameke Jean-Baptiste⁵  Kablan Ahmont Landry Claude⁶ 

[1] Department of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey;Laboratoire de Chimie Organique Heterocyclique URAC 21, Pôle de Competence Pharmacochimie, Faculté des Sciences, Universite Mohammed V, Rabat, Morocco;Laboratoire de Chimie Organique et de Substances Naturelles, UFR Sciences des Structures de la Matière et Technologie, Université Félix Houphouët-Boigny, 22 BP 582 Abidjan, Côte d'Ivoire;Laboratoire de Cristallographie et Physique Moléculaire, UFR SSMT, Université Félix Houphouët Boigny, 01 BP V34 Abidjan 01, Côte d'Ivoire;Laboratoire de Thermodynamique et Physicochimie du Milieu, Université Nangui Abrogoua, UFR-SFA, 02 BP 801 Abidjan 02, Côte d'Ivoire;UFR des Sciences Biologiques, Université Péléforo Gon Coulibaly, BP 1328 Korhogo, Côte d'Ivoire;

关键词: crystal structure;    perimidin;    methoxyphenol;    hirshfeld surface;   

DOI  :  10.1107/S2056989020004284

来源: DOAJ

【 摘 要 】

The title compound, C18H16N2O2, consists of perimidine and methoxyphenol units, where the tricyclic perimidine unit contains a naphthalene ring system and a non-planar C4N2 ring adopting an envelope conformation with the NCN group hinged by 47.44 (7)° with respect to the best plane of the other five atoms. In the crystal, O—HPhnl...NPrmdn and N—HPrmdn...OPhnl (Phnl = phenol and Prmdn = perimidine) hydrogen bonds link the molecules into infinite chains along the b-axis direction. Weak C—H...π interactions may further stabilize the crystal structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (49.0%), H...C/C...H (35.8%) and H...O/O...H (12.0%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Computational chemistry indicates that in the crystal, the O—HPhnl...NPrmdn and N—HPrmdn...OPhnl hydrogen-bond energies are 58.4 and 38.0 kJ mol−1, respectively. 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