Tan Sang Loon, Tiekink Edward R T
Research Centre for Crystalline Materials, School of Science and Technology, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia.
Acta Crystallogr E Crystallogr Commun. 2020 May 29;76(Pt 6):933-939. doi: 10.1107/S2056989020006829. eCollection 2020 Jun 1.
The title di-substituted thio-urea, CHNOS, has the hy-droxy-lethyl and ethyl benzoate substituents bound to the same amine-N atom, and is twisted, having a (+)syn-clinal conformation with the N-C-C-O torsion angles of 49.39 (13) and 59.09 (12)°, respectively; the dihedral angle between the almost planar CNS core and the pendent benzene ring is 69.26 (4)°. In the crystal, supra-molecular layers propagating in the plane are formed a combination of hydroxyl-O-H⋯S(thione), amine-N-H⋯O(hydroxyl, carbon-yl) hydrogen-bonds. The layers stack along the axis with inter-digitation of the benzene rings allowing the formation of π-π stacking [inter-centroid separation = 3.8722 (7) Å] and parallel C=O⋯π inter-actions. A computational chemistry study shows the conventional hydrogen bonding in the crystal leads to significant electrostatic stabilization but dispersion terms are also apparent, notably through the inter-actions involving the benzene residue.
标题二取代硫脲CHNOS中，羟乙基和苯甲酸乙酯取代基连接在同一个胺氮原子上，呈扭曲状，具有（+）顺式构象，N-C-C-O扭转角分别为49.39 (13)°和59.09 (12)°；近乎平面的CNS核心与悬垂苯环之间的二面角为69.26 (4)°。在晶体中，由羟基-O-H⋯S（硫酮）、胺-N-H⋯O（羟基、羰基）氢键的组合形成了在平面内传播的超分子层。这些层沿着轴堆叠，苯环相互交错，从而形成π-π堆积[质心间距 = 3.8722 (7) Å]和平行的C=O⋯π相互作用。一项计算化学研究表明，晶体中的传统氢键导致了显著的静电稳定作用，但色散项也很明显，特别是通过涉及苯残基的相互作用。
