N,N′-Di(pyridine-4-yl)-pyridine-3,5-dicarboxamide, a Pincer-Type Tricationic Compound; Synthesis, Crystal Structure, Hirshfeld Surface Analysis, and Computational Chemistry Studies,Journal of Chemical Crystallography

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N,N′-Di(pyridine-4-yl)-pyridine-3,5-dicarboxamide, a Pincer-Type Tricationic Compound; Synthesis, Crystal Structure, Hirshfeld Surface Analysis, and Computational Chemistry Studies
Journal of Chemical Crystallography ( IF 0.4 ) Pub Date : 2021-09-13 , DOI: 10.1007/s10870-021-00902-4
Bitrus Bikimi Ayiya ₁ , Obinna Chibueze Okpareke ₂

Affiliation

Abstract

The synthesis, structure, and spectroscopic characterization of a pincer-type compound; N,N′-di(pyridine-4-yl)-pyridine-3,5-dicarboxamide is described_. The tricationic pro-ligand (C₂₀H₂₂N₅O₂)³⁺ bearing two pendant alkylated 4-pyridyl arms at the 3,5-positions of the central pyridyl group features three triflate anions (CF₃SO₃⁻) in the asymmetric unit. Two of the triflate ligands in the structure are connected to the pincer cation by strong N–H⋯O hydrogen bonds. The central N-methyl moiety is planar to a r.m.s deviation of 0.01, and the two adjacent N-methylpyridine moieties are out of the plane with dihedral angles of 33.62° (3) and 86.08° (3). The molecular packing structure of the compound shows an 18-molecule aggregate in a 3-dimensional supramolecular synthon stabilized by intermolecular N–H⋯O and C–H⋯O contacts. The Hirshfeld surface analysis and fingerprint plots show that the OH/HO contacts resulting from C–H⋯O intermolecular interactions contributed significantly to the overall surface interaction with a total percentage contribution of 35.4%. The pairwise interaction energy calculations were implemented with a Gaussian plugin in Crystal Explorer 17 at the B3LYP/6-31G(d,p) level of theory. Energy profile diagrams and interaction energy values indicate that the crystal structure was stabilized by a combination of electrostatic and dispersion forces in the crystal lattice.

Graphic Abstract

The crystal structure of a tricationic pro-ligand N,N′-di(pyridine-4-yl)-pyridine-3,5-dicarboxamide is described. The structures features three triflate anions in the asymmetric unit with two of the triflate ligands in the structure connected to the pincer pro-ligand by strong N–H⋯O hydrogen bonds. Hirshfeld surface interaction and pairwise interaction energies are explored.

中文翻译：

N,N'-Di(pyridine-4-yl)-pyridine-3,5-dicarboxamide，一种钳型三阳离子化合物；合成、晶体结构、Hirshfeld 表面分析和计算化学研究

摘要

一种钳状化合物的合成、结构和光谱表征；描述了 N,N'-二(吡啶-4-基)-吡啶-3,5-二甲酰胺_。所述tricationic前配体（C ₂₀ ħ ₂₂ Ñ ₅ Ò ₂）³⁺带有两个侧挂在中心吡啶基的3,5-二烷基化的位置4-吡啶基臂具有三个三氟甲磺酸阴离子（CF ₃ SO ₃^-）在不对称单位。结构中的两个三氟甲磺酸酯配体通过强 N-H⋯O 氢键连接到钳形阳离子。中心N-甲基部分是平面的，rms 偏差为 0.01，两个相邻的N-甲基吡啶部分位于平面外，二面角为 33.62° (3) 和 86.08° (3)。该化合物的分子堆积结构显示了 18 分子聚集体在 3 维超分子合成子中，由分子间 N-H⋯O 和 C-H⋯O 接触稳定。Hirshfeld 表面分析和指纹图表明，由 C–H⋯O 分子间相互作用产生的 OH/H2O 接触对整体表面相互作用有显着贡献，总贡献百分比为 35.4%。在 B3LYP/6-31G(d,p) 理论水平上，使用 Crystal Explorer 17 中的高斯插件实现了成对相互作用能量计算。能量分布图和相互作用能值表明晶体结构通过晶格中的静电力和色散力的组合而稳定。