Ghandour Ismail, Bouayad Abdelouahed, Hökelek Tuncer, Haoudi Amal, Capet Frédéric, Renard Catherine, Kandri Rodi Youssef
Laboratoire de Chimie de la Matière Condensée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Immouzzer, BP 2202, Fez, Morocco.
Department of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey.
Acta Crystallogr E Crystallogr Commun. 2019 Jun 4;75(Pt 7):951-956. doi: 10.1107/S2056989019007801. eCollection 2019 Jul 1.
The title compound, CHNO, consists of an imidazolidine unit linked to two phenyl rings and two prop-2-yn-1-yl moieties. The imidazolidine ring is oriented at dihedral angles of 79.10 (5) and 82.61 (5)° with respect to the phenyl rings, while the dihedral angle between the two phenyl rings is 62.06 (5)°. In the crystal, inter-molecular C-H⋯O (Prop = prop-2-yn-1-yl and Imdzln = imidazolidine) hydrogen bonds link the mol-ecules into infinite chains along the -axis direction. Two weak C-H⋯π inter-actions are also observed. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (43.3%), H⋯C/C⋯H (37.8%) and H⋯O/O⋯H (18.0%) inter-actions. Hydrogen bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Computational chemistry indicates that the C-H⋯O hydrogen-bond energy in the crystal is -40.7 kJ mol. Density functional theory (DFT) optimized structures at the B3LYP/6-311G(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由一个与两个苯环和两个丙-2-炔-1-基部分相连的咪唑烷单元组成。咪唑烷环相对于苯环的二面角为79.10 (5)°和82.61 (5)°，而两个苯环之间的二面角为62.06 (5)°。在晶体中，分子间C-H⋯O（Prop = 丙-2-炔-1-基，Imdzln = 咪唑烷）氢键将分子沿c轴方向连接成无限链。还观察到两种弱C-H⋯π相互作用。晶体结构的 Hirshfeld 表面分析表明，晶体堆积的最重要贡献来自H⋯H（43.3%）、H⋯C/C⋯H（37.8%）和H⋯O/O⋯H（18.0%）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。计算化学表明晶体中的C-H⋯O氢键能为-40.7 kJ mol。在B3LYP/6-311G(d,p)水平上的密度泛函理论（DFT）优化结构与固态下实验测定的分子结构进行了比较。阐明了HOMO-LUMO行为以确定能隙。
