Cocrystals offer an opportunity to modulate the properties of active pharmaceutical ingredients (APIs). The formation of heteromolecular hydrogen bonds is important in the prediction and formation of cocrystals. In this article, ten cocrystals of flavonoids and 4,4′-vinylenedipyridine (VDP) were synthesized and characterized. By calculating the molecular electrostatic potential surfaces (MEPS) of flavonoids and VDP, the possible heteromolecular hydrogen bonds and API/CCF ratio in the cocrystals were predicted. Single crystals of the ten cocrystals were all obtained, and their crystal structures were elaborated. After analyzing the computational data and the experimental results, it was found that the predicted results matched well with the actual situations in cocrystals when the potential number of intermolecular hydrogen-bond donors in the flavonoids are no more than two. In other cases, the situation of heteromolecular hydrogen bonds will be more complex.

中文翻译：

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黄酮类化合物和4,4'-亚乙烯基二吡啶共晶体形成的见解：杂氢键，摩尔比和结构分析

共晶提供了调节活性药物成分（API）性质的机会。杂分子氢键的形成对共晶的预测和形成很重要。本文合成并表征了十个类黄酮和4,4'-乙烯基二吡啶（VDP）的共晶体。通过计算类黄酮和VDP的分子静电势表面（MEPS），预测了共晶中可能存在的异氢键和API / CCF比。全部获得了十个共晶的单晶，并且详细说明了它们的晶体结构。在分析了计算数据和实验结果之后，发现当类黄酮中分子间氢键供体的潜在数目不超过两个时，预测结果与共晶中的实际情况非常吻合。在其他情况下，杂分子氢键的情况将更加复杂。