A new cocrystal formed between the nutraceutical compounds pterostilbene and theophylline was synthesized and X-ray characterized in the form of a dichloromethane solvate. An interesting supramolecular assembly is formed by means of a combination of common and uncomment π–π and H-bonding interactions. It was computationally studied by a combination of density functional theory (DFT), quantum theory of “atoms-in-molecules”, and noncovalent interaction plot approaches, and the analyses revealed a π(C═C)···H-bond array interaction, which is the first description of this type of interaction where the donor π-system is a double bond. The participation of the cocrystallized CH₂Cl₂ solvent molecule in Cl···Cl and C–H···π interactions was also studied using DFT and Hirshfeld surface calculations. The Cambridge structural database was inspected to investigate whether the π···H-bond array interaction is common in other theophylline cocrystals. Other examples where the π-system of an aromatic ring or an amido group interact with the H-bond array were found in literature and further discussed herein.

中文翻译：

---

DFT分析在新型蝶形/茶碱共晶体中不常见的π··H键阵列相互作用

合成了在营养保健品化合物蕨类植物和茶碱之间形成的新共晶体，并以二氯甲烷溶剂化物的形式表征了X射线。一个有趣的超分子组装是通过普通和非注释π-π以及H键相互作用的组合而形成的。通过结合密度泛函理论（DFT），“分子中的原子”量子理论和非共价相互作用图方法对它进行了计算研究，分析结果显示出π（C═C）···H键阵列相互作用，这是这种类型相互作用的第一个描述，其中供体π系统是双键。共结晶CH ₂ Cl ₂的参与还使用DFT和Hirshfeld表面计算研究了Cl··Cl和C–H···π相互作用中的溶剂分子。检查了剑桥结构数据库，以调查在其他茶碱共晶体中π···H键阵列相互作用是否普遍。在文献中发现了芳环或酰胺基的π系统与H键阵列相互作用的其他实例，并在本文中进一步讨论。