6-溴-3-(5-溴己基)-2-[4-(二甲基氨基)苯基]-3-咪唑并[4,5-]吡啶的晶体结构、 Hirshfeld表面分析及密度泛函理论研究
Crystal structure, Hirshfeld surface analysis and DFT study of 6-bromo-3-(5-bromo-hex-yl)-2-[4-(di-methyl-amino)-phen-yl]-3-imidazo[4,5-]pyridine.
作者信息
Jabri Zainab, Sebbar Nada Kheira, Hökelek Tuncer, Mague Joel T, Sabir Safia, Rodi Youssef Kandri, Misbahi Khalid
机构信息
Laboratory of Applied Organic Chemistry, Sidi Mohamed Ben Abdellah University, Faculty of Sciences and Techniques, Road Immouzer, BP 2202 Fez, Morocco.
Laboratoire de Chimie Bioorganique Appliquée et Environnement Equipe de Chimie, Bioorganique Appliquée, Faculté des Sciences, Université Ibn Zohr, Agadir, Morocco.
出版信息
Acta Crystallogr E Crystallogr Commun. 2020 Jul 10;76(Pt 8):1234-1238. doi: 10.1107/S2056989020008889. eCollection 2020 Aug 1.
In the title mol-ecule, CHBrN, the imidazo-pyridine moiety is not planar as indicated by the dihedral angle of 2.0 (2)° between the constituent rings; the 4-di-methyl-amino-phenyl ring is inclined to the mean plane of the imidazole ring by 27.4 (1)°. In the crystal, two sets of C-H⋯π(ring) inter-actions form stacks of mol-ecules extending parallel to the axis direction. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (42.2%), H⋯C/C⋯H (23.1%) and H⋯Br/Br⋯H (22.3%) inter-actions. The optimized structure calculated using density functional theory (DFT) at the B3LYP/ 6-311 G(d,p) level is compared with the experimentally determined structure in the solid state. The calculated HOMO-LUMO energy gap is 2.3591 eV.
在标题分子CHBrN中，咪唑并吡啶部分并非平面结构，组成环之间的二面角为2.0（2）°；4-二甲基氨基苯基环相对于咪唑环的平均平面倾斜27.4（1）°。在晶体中，两组C-H⋯π（环）相互作用形成了平行于轴方向延伸的分子堆叠。 Hirshfeld表面分析表明，对晶体堆积最重要的贡献来自H⋯H（42.2%）、H⋯C/C⋯H（23.1%）和H⋯Br/Br⋯H（22.3%）相互作用。使用密度泛函理论（DFT）在B3LYP/6-311G（d,p）水平计算得到的优化结构与固态下实验测定的结构进行了比较。计算得到的HOMO-LUMO能隙为2.3591 eV。
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