Hirshfeld Surface Analysis and Energy Framework for Crystals of Quinazoline Methylidene Bridged Compounds

Abstract

The crystal structures of 4-(3,4-dimethoxyphenylethylamino)-methylidene-2,3,4,10-tetrahydro-1H-pyrido[2,1-b]-quinazolin-10-one (1) and 4-(3,4-methylene-dioxyphenylethylamino)-methylidene-2,3,4,10-tetrahydro-1H-pyrido[2,1-b]-quina-zolin-10-one hydrochloride (2) were studied by single crystal X-ray diffraction. Their molecular and crystal structures are described in the context of intra- and inter-molecular interactions and of stereoisomerism. The crystallographic study established mixed E, Z configuration about the C4=C12 bond for (1) and E configuration about the C4=C12 bond for (2). For molecular crystals, Hirshfeld surface analyses may provide insight into intermolecular interactions, and energy framework analyses allow one to quantify different contributions to the overall energy. These analyses were performed to pinpoint intermolecular interactions in (1) and (2). According to our results, the molecules are associated with intra- and intermolecular hydrogen bonds, C-H···π and π-stacking interactions. The three-dimensional Hirshfeld surface analyses and two-dimensional fingerprint plots revealed that the structures are dominated by H···H, H···C/C···H and H···O/O···H contacts. The intermolecular energy analysis confirmed a significant contribution of dispersion to the stabilization of molecular packings in (1) and (2).

Experimental and theoretical investigations on a furan-2-carboxamide-bearing thiazole: synthesis, molecular characterization by IR/NMR/XRD, electronic characterization by DFT, Hirshfeld surface analysis and biological activity

“…Hirshfeld surface analysis is a unique and useful tool for understanding the nature of intermolecular interactions and the 3D packing modes of crystal structures. The Hirshfeld surface can be described as an area around the molecule separating it from the space in the crystal (Spackman & Jayatilaka, 2009;Tojiboev et al, 2020). This analysis allows the creation of several maps, such as d norm , shape index and curvedness, each giving different information, and twodimensional (2D) fingerprint plots, which show the contributions of noncovalent interactions to the crystal packing in a quantitative manner.…”

HIRSHFELD SURFACE ANALYSIS OF CRYSTALS OF COMPLEXES - PRODUCTS OF REACTION IN SYSTEMS МХ2 – 1,10-PHENANTHROLINE – GeO2 – CITRIC ACID (М = Ni, Co; X = Cl, CH3COO)

“…[1]. Одним з найбільш ефективних та часто застосовуваних квантово-хімічних методів, що дозволяє кількісно оцінити поверхні молекул, охарактеризувати водневі зв'язки, p-p стекінг взаємодії в структурах є метод поверхонь Хіршфельда [2][3][4][5][6][7].…”