Crystallographic and Computational Studies of Conformationally Controlled 1,3-Bis(benzo[b]selenophen-2-yl)thiourea by Chalcogen-Bonding Interactions

IF 0.7 4区化学 Q4 CRYSTALLOGRAPHY

Journal of Chemical Crystallography Pub Date : 2026-10-13 DOI:10.1007/s10870-026-01121-5

Takumi Inoue, Nami Morita, Yui Amijima, Rika Sakai, Ryuji Kyan, Shohei Hamada, Yusuke Kobayashi, Takumi Furuta

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引用次数: 0

Abstract

A single crystal of 1,3-bis(benzo[b]selenophen-2-yl)thiourea (1) was obtained from a mixed solvent of dimethyl sulfoxide (DMSO) and acetone, and its crystal structure was determined using X-ray diffraction (XRD) analysis. The crystallographic study revealed that 1 adopts a planar structure in the trans–trans conformation with an Se⋯S⋯Se arrangement by chalcogen-bonding interactions. A thiourea–DMSO solvate, comprising two molecules of 1 and four DMSO molecules, was formed within the asymmetric unit. This solvate crystallizes in the orthorhombic system with Pca2₁ as the space group and is stabilized by N–H⋯O and C–H⋯O hydrogen-bonding interactions. Furthermore, the electronic nature of 1 was investigated using density functional theory (DFT) calculations, including natural bond orbital (NBO) analysis and reduced density gradient (RDG)-based non-covalent interaction (NCI) plot index analysis as well as QTAIM analysis, to confirm the presence of chalcogen-bonding interactions on both sides of the thiocarbonyl group.

Graphical Abstract

The structure of 1,3-bis(benzo[b]selenophen-2-yl)thiourea–DMSO solvate displays intramolecular Se⋯S⋯Se chalcogen-bonding interactions, as well as intermolecular N–H⋯O and C–H⋯O hydrogen-bonding interactions

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硫键作用下构象控制的1,3-二（苯并[b]硒酚-2-基）硫脲的晶体学和计算研究

在二甲亚砜（DMSO）和丙酮的混合溶剂中制备了1,3-双（苯并[b]硒苯-2-基）硫脲(1)单晶，并用x射线衍射（XRD）分析了其晶体结构。晶体学研究表明，1在反-反式构象中采用平面结构，通过硫键相互作用具有Se⋯S⋯Se排列。在不对称单元内形成由2个1分子和4个DMSO分子组成的硫脲- DMSO溶剂化物。该溶剂化物在以Pca2 1为空间基团的正交体系中结晶，并通过N-H⋯O和C-H⋯O氢键相互作用稳定。此外，利用密度泛函理论（DFT）计算，包括自然键轨道（NBO）分析和基于降低密度梯度（RDG）的非共价相互作用（NCI）图指数分析以及QTAIM分析，研究了1的电子性质，以确认硫羰基两侧存在硫键相互作用。图形摘要1,3-双（苯并[b]硒苯-2-基）硫脲- dmso溶剂化物的结构显示出分子内Se⋯S⋯Se硫键相互作用，以及分子间N-H⋯O和C-H⋯O氢键相互作用

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来源期刊

Journal of Chemical Crystallography 化学-光谱学

CiteScore

1.50

自引率

12.50%

发文量

审稿时长

6.3 months

期刊介绍： Journal of Chemical Crystallography is an international and interdisciplinary publication dedicated to the rapid dissemination of research results in the general areas of crystallography and spectroscopy. Timely research reports detail topics in crystal chemistry and physics and their relation to problems of molecular structure; structural studies of solids, liquids, gases, and solutions involving spectroscopic, spectrometric, X-ray, and electron and neutron diffraction; and theoretical studies.