Two new 1,3-dicarbonyl compounds bearing an o-hydroxyphenyl moiety (for short, I and II) were synthesized and subjected to structural, experimental and theoretical studies. Vibrational spectroscopy (IR, Raman, diffuse reflectance and X-ray diffraction) were used for solid phase studies, while NMR and electron spectroscopy allowed analysis in solution. The crystal structures of I and II, determined by X-ray diffraction methods, are closely related to each other (rms deviation of homologous atoms from their best fit is 0.147 Å). The observed planarity of β-hydroxyphenylcarbonyl enols fragment in the compounds is enforced by both extended π-bonding and intramolecular OH∙∙∙O bonds. Molecules in I are arranged in the lattice as center-symmetric dimers held by relatively weak intermolecular OH∙∙∙O bonds. Hirshfeld surface (HS) analysis, atoms in molecules (QTAIM), and natural bonding orbitals (NBO) approaches were employed to study theoretically selected dimers constructed from X-ray data. The results were combined with experimental ones to obtain deep insight into the strength and type of intermolecular interactions. A chalcogen bond interaction was detected in I. Although the O···O interaction is unusual, it participates in the attractive forces that stabilize the crystal lattice. The title compounds are present in the solid state only as the ketoenol tautomer, while in solution the diketo tautomer is also detected at concentrations of 5%. In vitro studies showed that I have better antimicrobial properties than II, mainly against the S. aureus strain.

中文翻译：

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1,3-二羰基化合物的结构和光谱研究以及分子间硫族键合相互作用。


合成了两种带有邻羟基苯基部分的新型1,3-二羰基化合物（简称I和II），并进行了结构、实验和理论研究。振动光谱（红外、拉曼、漫反射和 X 射线衍射）用于固相研究，而核磁共振和电子光谱则允许在溶液中进行分析。通过 X 射线衍射方法确定的 I 和 II 的晶体结构彼此密切相关（同源原子与其最佳拟合的均方根偏差为 0.147 Å）。观察到的化合物中 β-羟基苯基羰基烯醇片段的平面性是由扩展的 π 键和分子内 OH∙∙∙O 键增强的。 I 中的分子在晶格中排列为由相对较弱的分子间 OH∙∙∙O 键保持的中心对称二聚体。采用赫什菲尔德表面 (HS) 分析、分子中原子 (QTAIM) 和自然键合轨道 (NBO) 方法来研究从 X 射线数据构建的理论上选定的二聚体。将结果与实验结果结合起来，深入了解分子间相互作用的强度和类型。在 I 中检测到硫族键相互作用。尽管 O·O 相互作用不常见，但它参与了稳定晶格的吸引力。标题化合物仅以酮烯醇互变异构体的形式以固态存在，而在溶液中也检测到浓度为5%的二酮互变异构体。体外研究表明，I 比 II 具有更好的抗菌性能，主要针对金黄色葡萄球菌菌株。