Tan Sang Loon, Jotani Mukesh M, Tiekink Edward R T
Research Centre for Crystalline Materials, School of Science and Technology, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia.
Department of Physics, Bhavan's Sheth R. A. College of Science, Ahmedabad, Gujarat 380001, India.
Acta Crystallogr E Crystallogr Commun. 2020 Jan 7;76(Pt 2):155-161. doi: 10.1107/S2056989019017328. eCollection 2020 Feb 1.
In the title compound, CHNOS, a tris-ubstituted thio-urea derivative, the central CNS chromophore is almost planar (r.m.s. deviation = 0.018 Å) and the pendant hy-droxy-ethyl groups lie to either side of this plane. While to a first approximation the thione-S and carbonyl-O atoms lie to the same side of the mol-ecule, the S-C-N-C torsion angle of -47.8 (2)° indicates a considerable twist. As one of the hy-droxy-ethyl groups is orientated towards the thio-amide residue, an intra-molecular N-H⋯O hydrogen bond is formed which leads to an (7) loop. A further twist in the mol-ecule is indicated by the dihedral angle of 65.87 (7)° between the planes through the CNS chromophore and the 4-nitro-benzene ring. There is a close match between the experimental and gas-phase, geometry-optimized (DFT) mol-ecular structures. In the crystal, O-H⋯O and O-H⋯S hydrogen bonds give rise to supra-molecular layers propagating in the plane. The connections between layers to consolidate the three-dimensional architecture are of the type C-H⋯O, C-H⋯S and nitro-O⋯π. The nature of the supra-molecular association has been further analysed by a study of the calculated Hirshfeld surfaces, non-covalent inter-action plots and computational chemistry, all of which point to the significant influence and energy of stabilization provided by the conventional hydrogen bonds.
在标题化合物CHNOS（一种三取代硫脲衍生物）中，中心CNS发色团几乎呈平面状（均方根偏差 = 0.018 Å），且悬垂的羟乙基位于该平面的两侧。虽然初步看来硫酮-S和羰基-O原子位于分子的同一侧，但-47.8 (2)°的S-C-N-C扭转角表明存在相当大的扭曲。由于其中一个羟乙基朝向硫代酰胺残基定向，形成了分子内N-H⋯O氢键，从而导致一个(7)环。通过CNS发色团的平面与4-硝基苯环的平面之间65.87 (7)°的二面角表明分子中存在进一步的扭曲。实验和气相几何优化（DFT）分子结构之间有很好的匹配。在晶体中，O-H⋯O和O-H⋯S氢键产生了在平面内传播的超分子层。层与层之间巩固三维结构的连接类型为C-H⋯O、C-H⋯S和硝基-O⋯π。通过对计算的Hirshfeld表面、非共价相互作用图和计算化学的研究，进一步分析了超分子缔合的性质，所有这些都表明传统氢键提供了显著的影响和稳定能量。
