Daouda Ballo, Tuo Nanou Tiéba, Hökelek Tuncer, Niameke Jean-Baptiste Kangah, Charles Guillaume Kodjo, Claude Kablan Ahmont Landry, Essassi El Mokhtar
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.
Acta Crystallogr E Crystallogr Commun. 2020 Apr 3;76(Pt 5):605-610. doi: 10.1107/S2056989020004284. eCollection 2020 May 1.
The title compound, CHNO, consists of perimidine and meth-oxy-phenol units, where the tricyclic perimidine unit contains a naphthalene ring system and a non-planar CN 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-H⋯N and N-H⋯O (Phnl = phenol and Prmdn = perimidine) hydrogen bonds link the mol-ecules into infinite chains along the -axis direction. Weak C-H⋯π inter-actions 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%) inter-actions. Hydrogen bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Computational chemistry indicates that in the crystal, the O-H⋯N and N-H⋯O hydrogen-bond energies are 58.4 and 38.0 kJ mol, respectively. Density functional theory (DFT) optimized structures at the B3LYP/ 6-311 G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.
标题化合物CHNO由嘧啶和甲氧基苯酚单元组成，其中三环嘧啶单元包含一个萘环体系和一个非平面的CN环，该环呈信封构象，NCN基团相对于其他五个原子的最佳平面扭转47.44 (7)°。在晶体中，O-H⋯N和N-H⋯O（Phnl = 苯酚，Prmdn = 嘧啶）氢键将分子沿轴方向连接成无限链。弱C-H⋯π相互作用可能进一步稳定晶体结构。晶体结构的 Hirshfeld 表面分析表明，对晶体堆积最重要的贡献来自H⋯H（49.0%）、H⋯C/C⋯H（35.8%）和H⋯O/O⋯H（12.0%）相互作用。氢键和范德华相互作用是晶体堆积中的主要相互作用。计算化学表明，在晶体中，O-H⋯N和N-H⋯O氢键能分别为58.4和38.0 kJ mol。在B3LYP/6-311 G(d,p)水平上对密度泛函理论（DFT）优化的结构与实验测定的固态分子结构进行了比较。阐明了HOMO-LUMO行为以确定能隙。
