Grześkiewicz Anita M, Ostrowska Agata, Borzylo Dmytro, Kubicki Maciej
Faculty of Chemistry, Adam Mickiewicz University, Uniwersytetu Poznańskiego 8, 61-614 Poznań, Poland.
Acta Crystallogr C Struct Chem. 2020 Oct 1;76(Pt 10):992-999. doi: 10.1107/S2053229620012504. Epub 2020 Sep 29.
The dissolution of 6-aminothiocytosine in common solvents (such as methanol, dimethyl sulfoxide and dichloromethane) under alkaline conditions is shown to afford new compounds with a 6-aminothiocytosine skeleton: 2,2'-disulfanediylbis(pyrimidine-4,6-diamine) (1), CHNS, 2,2'-[methanediylbis(sulfanediyl)]bis(pyrimidine-4,6-diamine) (2), CHNS, 2-[(methoxymethyl)sulfanyl]pyrimidine-4,6-diamine (3), CHNOS, and poly[(μ-4,6-diaminopyrimidine-2-sulfinato)potassium(I)] (4), [K(CHNOS)]. The crystal architectures of these compounds are found to be strongly influenced by extensive hydrogen-bond networks, although some individual features are also observed. Specifically, 1 is characterized by very short C-H...N hydrogen bonds, 2 features apparently weak and long C-H...π, C-H...S and π-π contacts as the greatest contributors to stabilization energy, while 3 contains ribbons of molecules formed by centrosymmetric dimers of two types, and 4 is characterized by layers with principal structural units comprising distorted six-molecule rings. The intermolecular interactions in 1-4 are characterized in terms of their geometry, topology and energy, and the corresponding results are confirmed and visualized using Hirshfeld surface analysis.
结果表明，6-氨基硫代胞嘧啶在碱性条件下于常见溶剂（如甲醇、二甲基亚砜和二氯甲烷）中溶解时，会生成具有6-氨基硫代胞嘧啶骨架的新化合物：2,2'-二硫二基双（嘧啶-4,6-二胺）（1），CHNS，2,2'-[甲烷二基双（硫二基）]双（嘧啶-4,6-二胺）（2），CHNS，2-[(甲氧基甲基)硫基]嘧啶-4,6-二胺（3），CHNOS，以及聚[(μ-4,6-二氨基嘧啶-2-亚磺酸钾（I）]（4），[K(CHNOS)]。尽管也观察到了一些个别特征，但发现这些化合物的晶体结构受到广泛氢键网络的强烈影响。具体而言，1的特征是具有非常短的C-H...N氢键，2的显著特征是明显较弱且较长的C-H...π、C-H...S和π-π接触对稳定化能贡献最大，而3包含由两种类型的中心对称二聚体形成的分子带，4的特征是具有由扭曲的六分子环组成主要结构单元的层。通过其几何形状、拓扑结构和能量对1-4中的分子间相互作用进行了表征，并使用 Hirshfeld 表面分析对相应结果进行了确认和可视化。
