The enantiomers of a previously reported naphthalimide derivative are shown in this study to form a solid solution; furthermore, on the basis of the knowledge of solid solution structural aspects other naphthalimide derivatives have been synthesized and shown to lack the enantioselectivity in the solid state. The structural origin of solid solution formation is the same as observed in most of the cases in the literature—quasi-centrosymmetric structures form at nonracemic compositions where the most abundant enantiomer adjusts its conformation to mimic the absent one. Such solid solutions belong to the type showing some enantioselectivity. An extended single crystal X-ray diffraction study of the crystals of different enantiomeric compositions reveals the nature of the disorder in studied solid solutions. Intermolecular interactions are analyzed in terms of Hirshfeld surfaces and by means of density functional theory calculations to explore the differences of isostructural quasi-centrosymmetric (enantiopure) and genuine centrosymmetric (racemic) packings to shed light on the energetic aspects of solid solution formation as well as to explain the origin of partial enantioselectivity. Furthermore, lattice energy calculations explain why two structurally distinct solid solutions (around the racemic and near the pure enantiomer regions) form as found for one of the studied compounds.

中文翻译：

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设计对映异构体的固溶体：固态的手性萘二甲酰亚胺衍生物对映体选择性不足

在这项研究中显示了先前报道的萘二甲酰亚胺衍生物的对映体形成了固溶体。此外，基于对固溶体结构方面的了解，已经合成了其他萘二甲酰亚胺衍生物，并且显示出在固态下缺乏对映选择性。固溶体形成的结构起源与文献中大多数情况下所观察到的相同-准-中心对称结构在非外消旋组合物上形成，其中最丰富的对映异构体调节其构象以模仿不存在的对映异构体。这样的固溶体属于表现出一定对映选择性的类型。对不同对映体组成的晶体进行的扩展单晶X射线衍射研究揭示了所研究固溶体中疾病的性质。分子间的相互作用根据Hirshfeld曲面进行分析，并通过密度泛函理论计算来探讨同构准结构的差异-中心对称（对映纯）和真正的中心对称（外消旋）填料，以阐明固溶体形成的高能方面，并解释部分对映选择性的起源。此外，晶格能计算解释了为什么形成一种结构不同的固溶体（在外消旋体附近和纯对映体区域附近），这是针对一种所研究化合物发现的。