The crystal structures of the antimicrobial drug tinidazole [TNZ; systematic name: 1‐(2‐ethylsulfonylethyl)‐2‐methyl‐5‐nitroimidazole, C₈H₁₃N₃O₄S] and the 1:1 cocrystal of TNZ with the naturally occurring compound vanillic acid (VA; systematic name: 4‐hydroxy‐3‐methoxybenzoic acid, C₈H₈O₄), namely, the TNZ–VA cocrystal, were determined by single‐crystal X‐ray analysis at 100 K. The supramolecular structure of the TNZ–VA cocrystal is composed of a carboxylic acid dimer and an O—H…N(heterocycle) synthon in the form of layers made up of O—H…N and O—H…O hydrogen bonds. The layers are joined via C—H…O hydrogen bonds, π–π stacking and C—H…π interactions. The energy framework analysis, together with interaction energy calculations using the DLPNO‐CCSD(T) method, indicates that the TNZ–VA cocrystal inherits strong interactions from the TNZ and VA crystals, which accounts for the enhanced thermal stability and reduced dissolution rate. To the best of our knowledge, this is the first example of a cocrystal containing TNZ.

中文翻译：

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替硝唑和替硝唑-香草酸共晶体的晶体结构，热稳定性和溶解行为：能量框架的见解。

抗菌药物替硝唑[ TNZ ; 系统名称：1-（2-乙基磺酰基乙基）-2-甲基-5-硝基咪唑，C ₈ H ₁₃ N ₃ O ₄ S]和TNZ与天然存在的化合物香草酸（VA） 1：1共晶；系统名称： 4-羟基-3-甲氧基苯甲酸，C ₈ ħ ₈ Ò ₄），即TNZ - VA共晶体中，通过单晶X射线分析在100 K.所述的超分子结构决定TNZ - VA共晶体由羧酸二聚体和OH-N（杂环）合成子组成，其形式为OH-N和OH-O氢键。这些层通过C–H…O氢键，π–π堆积和CH–H…π相互作用连接。能量框架分析以及使用DLPNO-CCSD（T）方法的相互作用能计算表明，TNZ - VA共晶体继承了TNZ和VA晶体的强相互作用，这说明了增强的热稳定性和降低的溶解速率。据我们所知，这是含TNZ共晶体的第一个例子。