Lahyaoui Mouad, Haoudi Amal, Kartah Badr Eddine, Mazzah Ahmed, Hökelek Tuncer, Mague Joel T, Kandri Rodi Youssef, Sebbar Nada Kheira
Laboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Immouzzer, BP 2202 Fez, Morocco.
Laboratory Of Applied Organic Chemistry, Sidi Mohamed Ben Abdellah University, Faculty Of Science And Technology, Road Immouzer, BP 2202 Fez, Morocco.
Acta Crystallogr E Crystallogr Commun. 2023 Nov 21;79(Pt 12):1183-1189. doi: 10.1107/S2056989023009933. eCollection 2023 Dec 1.
In the title mol-ecule, CHNO, the pyrimidine ring is essentially planar, with the propynyl group rotated out of this plane by 15.31 (4)°. In the crystal, a tri-periodic network is formed by N-H⋯O, N-H⋯N and C-H⋯O hydrogen-bonding and slipped π-π stacking inter-actions, leading to narrow channels extending parallel to the axis. Hirshfeld surface analysis of the crystal structure reveals that the most important contributions for the crystal packing are from H⋯H (36.2%), H⋯C/C⋯H (20.9%), H⋯O/O⋯H (17.8%) and H⋯N/N⋯H (12.2%) inter-actions, showing that hydrogen-bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Evaluation of the electrostatic, dispersion and total energy frameworks indicates that the stabilization is dominated by the electrostatic energy contributions. The mol-ecular structure optimized by density functional theory (DFT) calculations at the B3LYP/6-311 G(d,p) level is compared with the experimentally determined structure in the solid state. The HOMO-LUMO behaviour was also elucidated to determine the energy gap.
在标题分子CHNO中，嘧啶环基本呈平面状，丙炔基旋转出该平面15.31 (4)°。在晶体中，通过N-H⋯O、N-H⋯N和C-H⋯O氢键以及滑移π-π堆积相互作用形成了一个三周期网络，导致平行于轴延伸的狭窄通道。对晶体结构的 Hirshfeld 表面分析表明，晶体堆积中最重要的贡献来自H⋯H（36.2%）、H⋯C/C⋯H（20.9%）、H⋯O/O⋯H（17.8%）和H⋯N/N⋯H（12.2%）相互作用，表明氢键和范德华相互作用是晶体堆积中的主要相互作用。对静电、色散和总能量框架的评估表明，稳定性主要由静电能量贡献主导。将在B3LYP/6-311 G(d,p)水平上通过密度泛函理论（DFT）计算优化的分子结构与固态下的实验测定结构进行了比较。还阐明了HOMO-LUMO行为以确定能隙。
