Title of article :
Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 2-(2,3-dihydro-1H-perimidin-2-yl)-6-methoxyphenol
Author/Authors :
Daoud , Ballo PLaboratoire de Chimie Organique Heterocyclique URAC 21 - Pôle de Competence harmacochimie - Faculté des Sciences - Universite Mohammed V, Rabat, Morocco , Tiéba Tuo, Nanou Laboratoire de Chimie Organique et de Substances Naturelles - UFR Sciences des Structures de la Matière et Technologie - Université Félix Houphouët-Boigny, Côte d'Ivoire , Hökelek, Tuncer Department of Physics - Hacettepe University, Turkey , Jean-Baptiste, Kangah Niameke Laboratoire de Thermodynamique et Physicochimie du Milieu - Université Nangui Abrogoua, Côte d'Ivoire , Charles Guillaume, Kodjo Laboratoire de Cristallographie et Physique Moléculaire - UFR SSMT - Université Félix Houphouët Boigny, Côte d'Ivoire , Landry Claude, Kablan Ahmont UFR des Sciences Biologiques - Université Péléforo Gon Coulibaly, Côte d'Ivoire , Essassia, El Mokhtar PLaboratoire de Chimie Organique Heterocyclique URAC 21 - Pôle de Competence harmacochimie - Faculté des Sciences - Universite Mohammed V, Rabat, Morocco
Abstract :
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.
Keywords :
crystal structure , perimidin , methoxyphenol , Hirshfeld surface
