The main objective of this study is to investigate the potential of cinnoline oxides and their nitro derivatives as explosive materials. Thus, the study includes the synthesis, crystal structure prediction, single-crystal X-ray structure determination, crystal packing analysis and calculation of the detonation properties of [1,2,5]oxadiazolo[3,4-c]cinnoline 5-oxide, 1,5-dioxides and their nitro derivatives. It was found that the exocyclic oxygen atom of the 1,2,5-oxadiazole ring affects the nitration reaction of the benzene ring of cinnoline oxides: its absence requires more hard nitration conditions, but at the same time makes it possible to obtain a dinitro cinnoline derivative. 7,9-Dinitro-[1,2,5]oxadiazolo[3,4-c]cinnoline 5-oxide was obtained for the first time. Previously unknown experimental crystal structures were established for six compounds. For all of the compounds studied, crystal structure prediction was used to obtain information about crystal packing, even in the absence of experimental data. It was shown that crystal structure prediction based on the grid algorithm for structure generation and a force field approach with a charge-shifted model of electrostatic interactions for energy minimization and ranking yielded reliable results for this class of compounds. Crystal packing analysis was used to reveal supramolecular synthons, and to find differences and similarities in crystal structures. For example, the crystals of cinnoline 1,5-dioxides, molecules with an exocyclic oxygen atom of the 1,2,5-oxadiazole ring, are isostructural or nearly isostructural to the corresponding cinnoline 5-oxides, but their density and oxygen balance are higher. The calculated detonation parameters indicated the moderate performance of the [1,2,5]oxadiazolo[3,4-c]cinnoline oxides as explosives.

中文翻译：

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[1,2,5]恶二唑并[3,4-c]肉啉5-氧化物、1,5-二氧化物及其硝基衍生物作为高能量密度材料的前景如何？合成、实验和预测的晶体结构以及计算的爆炸特性

本研究的主要目的是研究肉啉氧化物及其硝基衍生物作为爆炸材料的潜力。因此，该研究包括[1,2,5]恶二唑并[3,4- c ]肉啉5-氧化物的合成、晶体结构预测、单晶X射线结构测定、晶体堆积分析和爆炸性质计算, 1,5-二氧化物及其硝基衍生物。研究发现1,2,5-恶二唑环的环外氧原子影响了肉啉氧化物苯环的硝化反应：它的缺失需要更困难的硝化条件，但同时使得获得二硝基成为可能肉桂啉衍生物。首次得到7,9-二硝基-[1,2,5]恶二唑并[3,4- c ]肉啉5-氧化物。建立了六种化合物以前未知的实验晶体结构。对于所有研究的化合物，即使在没有实验数据的情况下，也可以使用晶体结构预测来获取有关晶体堆积的信息。结果表明，基于用于结构生成的网格算法和用于能量最小化和排序的静电相互作用的电荷转移模型的力场方法的晶体结构预测为此类化合物产生了可靠的结果。晶体堆积分析用于揭示超分子合成子，并找出晶体结构的差异和相似之处。例如，肉啉1,5-二氧化物的晶体，即具有1,2,5-恶二唑环的环外氧原子的分子，与相应的肉啉5-氧化物是同构或接近同构的，但它们的密度和氧平衡是不同的。更高。计算的爆炸参数表明[1,2,5]恶二唑并[3,4- c ]肉啉氧化物作为炸药具有中等性能。