Understanding the supramolecular environment of crystal structures is necessary to facilitate designing molecules with desirable properties. A series of 12 novel 1,3,5-tris(1-phenyl-1H-pyrazol-5-yl)benzenes was used to assess the existence of planar stacking columns in supramolecular structures of pyrazoles. This class of molecules with different substituents may assist in understanding how small structural changes affect the supramolecular environment. The obtained compounds did not present the formation of planar stacking interactions between benzenes in solid or liquid states. This supposition was indicated by single crystal diffraction, Density Functional Theory (DFT) and quantum theory of atoms in molecules (QTAIM) calculations, and concentration-dependent liquid-state 1H nuclear magnetic resonance (NMR). NMR showed that chemical shifts of benzene and pyrazole hydrogens confirm that planar stacking interactions are not formed in solution. The crystalline structures presented different molecular conformations. The molecular structures of 5 and 9b are in a twisted conformation, while compound 7 showed a conformation analogous to a calyx form.

中文翻译：

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1,3,5-三(1-苯基-1H-吡唑-5-基)苯的合成、晶体结构和超分子理解

了解晶体结构的超分子环境对于设计具有理想特性的分子是必要的。一系列 12 种新型 1,3,5-三(1-苯基-1H-吡唑-5-基)苯用于评估吡唑超分子结构中平面堆积柱的存在。这类具有不同取代基的分子可能有助于理解微小的结构变化如何影响超分子环境。所得化合物在固态或液态苯之间没有形成平面堆积相互作用。单晶衍射、密度泛函理论 (DFT) 和分子中原子的量子理论 (QTAIM) 计算以及浓度相关的液态 1 H 核磁共振 (NMR) 表明了这一假设。NMR 显示苯和吡唑氢的化学位移证实在溶液中没有形成平面堆叠相互作用。晶体结构呈现不同的分子构象。5 和 9b 的分子结构呈扭曲构象，而化合物 7 显示出类似于花萼的构象。