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()-{[(丁基硫烷基)甲硫基]氨基}(4-甲氧基亚苄基)胺:晶体结构与 Hirshfeld 表面分析

()-{[(Butyl-sulfan-yl)methane-thio-yl]amino}(4-meth-oxy-benzyl-idene)amine: crystal structure and Hirshfeld surface analysis.

作者信息

Rusli Aqilah Fasihah, Kwong Huey Chong, Crouse Karen A, Jotani Mukesh M, Tiekink Edward R T

机构信息

Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, UPM, Serdang 43400, Malaysia.

Department of Physics, Bhavan's Sheth R. A. College of Science, Ahmedabad, Gujarat 380001, India.

出版信息

Acta Crystallogr E Crystallogr Commun. 2020 Jan 17;76(Pt 2):208-213. doi: 10.1107/S2056989020000328. eCollection 2020 Feb 1.

Abstract

The title hydrazine carbodi-thio-ate, CHNOS, is constructed about a central and almost planar CNS chromophore (r.m.s. deviation = 0.0263 Å); the terminal meth-oxy-benzene group is close to coplanar with this plane [dihedral angle = 3.92 (11)°]. The -butyl group has an extended all- conformation [torsion angles S-C-C-C = -173.2 (3)° and C-C-C-C = 180.0 (4)°; m = methyl-ene and me = meth-yl]. The most prominent feature of the mol-ecular packing is the formation of centrosymmetric eight-membered {⋯HNCS} synthons, as a result of thio-amide-N-H⋯S(thio-amide) hydrogen bonds; these are linked meth-oxy-C-H⋯π(meth-oxy-benzene) inter-actions to form a linear supra-molecular chain propagating along the -axis direction. An analysis of the calculated Hirshfeld surfaces and two-dimensional fingerprint plots point to the significance of H⋯H (58.4%), S⋯H/H⋯S (17.1%), C⋯H/H⋯C (8.2%) and O⋯H/H⋯O (4.9%) contacts in the packing. The energies of the most significant inter-actions, . the N-H⋯S and C-H⋯π inter-actions have their most significant contributions from electrostatic and dispersive components, respectively. The energies of two other identified close contacts at close to van der Waals distances, . a thione-sulfur and meth-oxy-benzene-hydrogen contact (occurring within the chains along the axis) and between methyl-ene-H atoms (occurring between chains to consolidate the three-dimensional architecture), are largely dispersive in nature.

摘要

标题为肼基二硫代甲酸酯,化学式为CHNOS,其结构围绕一个中心且近乎平面的CNS发色团构建(均方根偏差 = 0.0263 Å);末端甲氧基苯基团与该平面近乎共面[二面角 = 3.92 (11)°]。丁基具有伸展的全反式构象[扭转角S - C - C - C = -173.2 (3)°和C - C - C - C = 180.0 (4)°;m = 亚甲基,me = 甲基]。分子堆积的最显著特征是由于硫代酰胺 - N - H⋯S(硫代酰胺)氢键形成了中心对称的八元{⋯HNCS}合成子;这些通过甲氧基 - C - H⋯π(甲氧基苯)相互作用相连,形成沿 - 轴方向传播的线性超分子链。对计算得到的Hirshfeld表面和二维指纹图谱的分析表明,H⋯H(58.4%)、S⋯H/H⋯S(17.1%)、C⋯H/H⋯C(8.2%)和O⋯H/H⋯O(4.9%)接触在堆积中具有重要意义。最显著相互作用的能量,即N - H⋯S和C - H⋯π相互作用,分别主要来自静电和色散成分。另外两个确定的接近范德华距离的紧密接触的能量,即硫酮硫和甲氧基苯 - 氢接触(沿 轴在链内发生)以及亚甲基 - H原子之间的接触(在链间发生以巩固三维结构),在本质上主要是色散性的。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1a96/7001837/a7f5c3e0ed84/e-76-00208-fig1.jpg

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