1. Crystallographic and Theoretical Exploration of Weak Hydrogen Bonds in Arylmethyl N'-(adamantan-1-yl)piperidine-1-carbothioimidates and Molecular Docking Analysis

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ACS Omega
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Crystal structures of two potential chemotherapeutic agents, namely 4-
nitrobenzyl N′-(adamantan-1-yl)piperidine-1-carbothioimidate 1 and 4-bromobenzyl N′-
(adamantan-1-yl)piperidine-1-carbothioimidate 2, have been analyzed in detail. X-ray analysis
reveals that the molecular conformations of these compounds are strikingly different. These
two structures are compared with two of their closely related structures. In the related
structures, morpholine replaces piperidine. Based on the Hirshfeld surface analysis and twodimensional
(2D) fingerprint plots, we describe the effects of piperidine/morpholine and Br/
NO2 groups on the intermolecular interactions. An analysis of the CLP-PIXEL energy provides
insight into the energetics of the dimers observed in the title compounds and their related
structures. Compound 1 stabilizes with bifurcated C−H···S, C−H···O, and O(lp)···C(π)
interactions, whereas compound 2 stabilizes with C−H···N, C−H···Br, and C−H···C
interactions. The energy frameworks for the crystal structures of the title compounds reveal
differences. The atoms-in-molecules (AIM) analysis was performed to confirm the
intermolecular interactions found in the crystal structures of 1 and 2. Additionally, docking analysis suggests that the title
compounds bind at the active site of human sphingosine kinase 1, a well-known cancer target.

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