Synthesis, crystal structure and Hirshfeld analysis of the bis{(E)-2-[1-(benzo[d][1,3]dioxol-5-yl)ethylidene]-N-ethylhydrazine-1-carbothioamide-κS}-dichloridomercury(II) complex
Synthesis, crystal structure and Hirshfeld analysis of the bis{(E)-2-[1-(benzo[d][1,3]dioxol-5-yl)ethylidene]-N-ethylhydrazine-1-carbothioamide-κS}-dichloridomercury(II) complex
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15.05.2026Publisher
IUCrPublisher Location
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https://hdl.handle.net/20.500.11811/14325
Abstract
The title compound, [HgCl2(C12H15N3O2S)2], was synthesized by the reaction of (E)-2-[1-(benzo[d][1,3]dioxol-5-yl)ethylidene]-N-ethylhydrazine-1-carbothioamide [common name: 3′,4′-(methylenedioxy)acetophenone 4-ethylthiosemicarbazone] with mercury(II) chloride in a 2:1 molar ratio at ambient temperature, using ethanol as solvent. A white solid was isolated and colourless single crystals of the title compound for the SC-XRD analysis were obtained from a solution in (methanesulfinyl)methane (common name: dimethyl sulfoxide, DMSO) with a hexane overlay. The HgII metal center is fourfold coordinated in a distorted tetrahedral geometry by two neutral thiosemicarbazone derivatives, acting as κS-donors, and two chlorido ligands. The complex molecule exhibits a sequence of four intramolecular hydrogen-bonded rings, formed by two interactions of the N—H⋅⋅⋅Cl type, with graph-set motifs of S(6) and showing a chelate-like coordination environment around the metal center, and two additional interactions of the N—H⋅⋅⋅N type with S(5) graph-set motifs. In the crystal, the molecules are linked via N—H⋅⋅⋅Cl intermolecular interactions along the c-axis, forming a hydrogen-bonded ribbon-like supramolecular arrangement that resembles a zigzag pattern along the c-axis direction, and with the Cl atoms acting as bridges between intra- and intermolecular hydrogen bonds. The Hirshfeld surface analysis suggests that the major contributions for the crystal cohesion are the H⋅⋅⋅H (40.4%), H⋅⋅⋅Cl/Cl⋅⋅⋅H (14.5%), H⋅⋅⋅C/C⋅⋅⋅H (11.3%), H⋅⋅⋅O/O⋅⋅⋅H (10.6%) and H⋅⋅⋅S/S⋅⋅⋅H (9.2%) intermolecular contacts, with the surface being mapped over the dnorm, shape-index and curvedness properties.
Subjects
crystal structure, thiosemicarbazone complex, mercury(II) complex, H-bonded chelate-type, H-bonded intramolecular rings
Classification (DDC)
540 ChemiePublished in
Acta crystallographica. Section E, Crystallographic communications, 2026, volume 82, part 6, pp. 656-664First Publication
https://doi.org/10.1107/S2056989026004822de Farias, Renan Lira; Beck, Johannes; Daniels, Jörg; Bof de Oliveira, Adriano: Synthesis, crystal structure and Hirshfeld analysis of the bis{(E)-2-[1-(benzo[d][1,3]dioxol-5-yl)ethylidene]-N-ethylhydrazine-1-carbothioamide-κS}-dichloridomercury(II) complex. In: Acta crystallographica. Section E, Crystallographic communications. 2026, volume 82, part 6, 656-664.
Online-Ausgabe in bonndoc: https://hdl.handle.net/20.500.11811/14325
Online-Ausgabe in bonndoc: https://hdl.handle.net/20.500.11811/14325
@article{handle:20.500.11811/14325,
author = {{Renan Lira de Farias} and {Johannes Beck} and {Jörg Daniels} and {Adriano Bof de Oliveira}},
title = {Synthesis, crystal structure and Hirshfeld analysis of the bis{(E)-2-[1-(benzo[d][1,3]dioxol-5-yl)ethylidene]-N-ethylhydrazine-1-carbothioamide-κS}-dichloridomercury(II) complex},
publisher = {IUCr},
year = 2026,
month = may,
journal = {Acta crystallographica. Section E, Crystallographic communications},
volume = 2026, volume 82,
number = part 6,
pages = 656--664,
note = {The title compound, [HgCl2(C12H15N3O2S)2], was synthesized by the reaction of (E)-2-[1-(benzo[d][1,3]dioxol-5-yl)ethylidene]-N-ethylhydrazine-1-carbothioamide [common name: 3′,4′-(methylenedioxy)acetophenone 4-ethylthiosemicarbazone] with mercury(II) chloride in a 2:1 molar ratio at ambient temperature, using ethanol as solvent. A white solid was isolated and colourless single crystals of the title compound for the SC-XRD analysis were obtained from a solution in (methanesulfinyl)methane (common name: dimethyl sulfoxide, DMSO) with a hexane overlay. The HgII metal center is fourfold coordinated in a distorted tetrahedral geometry by two neutral thiosemicarbazone derivatives, acting as κS-donors, and two chlorido ligands. The complex molecule exhibits a sequence of four intramolecular hydrogen-bonded rings, formed by two interactions of the N—H⋅⋅⋅Cl type, with graph-set motifs of S(6) and showing a chelate-like coordination environment around the metal center, and two additional interactions of the N—H⋅⋅⋅N type with S(5) graph-set motifs. In the crystal, the molecules are linked via N—H⋅⋅⋅Cl intermolecular interactions along the c-axis, forming a hydrogen-bonded ribbon-like supramolecular arrangement that resembles a zigzag pattern along the c-axis direction, and with the Cl atoms acting as bridges between intra- and intermolecular hydrogen bonds. The Hirshfeld surface analysis suggests that the major contributions for the crystal cohesion are the H⋅⋅⋅H (40.4%), H⋅⋅⋅Cl/Cl⋅⋅⋅H (14.5%), H⋅⋅⋅C/C⋅⋅⋅H (11.3%), H⋅⋅⋅O/O⋅⋅⋅H (10.6%) and H⋅⋅⋅S/S⋅⋅⋅H (9.2%) intermolecular contacts, with the surface being mapped over the dnorm, shape-index and curvedness properties.},
url = {https://hdl.handle.net/20.500.11811/14325}
}
author = {{Renan Lira de Farias} and {Johannes Beck} and {Jörg Daniels} and {Adriano Bof de Oliveira}},
title = {Synthesis, crystal structure and Hirshfeld analysis of the bis{(E)-2-[1-(benzo[d][1,3]dioxol-5-yl)ethylidene]-N-ethylhydrazine-1-carbothioamide-κS}-dichloridomercury(II) complex},
publisher = {IUCr},
year = 2026,
month = may,
journal = {Acta crystallographica. Section E, Crystallographic communications},
volume = 2026, volume 82,
number = part 6,
pages = 656--664,
note = {The title compound, [HgCl2(C12H15N3O2S)2], was synthesized by the reaction of (E)-2-[1-(benzo[d][1,3]dioxol-5-yl)ethylidene]-N-ethylhydrazine-1-carbothioamide [common name: 3′,4′-(methylenedioxy)acetophenone 4-ethylthiosemicarbazone] with mercury(II) chloride in a 2:1 molar ratio at ambient temperature, using ethanol as solvent. A white solid was isolated and colourless single crystals of the title compound for the SC-XRD analysis were obtained from a solution in (methanesulfinyl)methane (common name: dimethyl sulfoxide, DMSO) with a hexane overlay. The HgII metal center is fourfold coordinated in a distorted tetrahedral geometry by two neutral thiosemicarbazone derivatives, acting as κS-donors, and two chlorido ligands. The complex molecule exhibits a sequence of four intramolecular hydrogen-bonded rings, formed by two interactions of the N—H⋅⋅⋅Cl type, with graph-set motifs of S(6) and showing a chelate-like coordination environment around the metal center, and two additional interactions of the N—H⋅⋅⋅N type with S(5) graph-set motifs. In the crystal, the molecules are linked via N—H⋅⋅⋅Cl intermolecular interactions along the c-axis, forming a hydrogen-bonded ribbon-like supramolecular arrangement that resembles a zigzag pattern along the c-axis direction, and with the Cl atoms acting as bridges between intra- and intermolecular hydrogen bonds. The Hirshfeld surface analysis suggests that the major contributions for the crystal cohesion are the H⋅⋅⋅H (40.4%), H⋅⋅⋅Cl/Cl⋅⋅⋅H (14.5%), H⋅⋅⋅C/C⋅⋅⋅H (11.3%), H⋅⋅⋅O/O⋅⋅⋅H (10.6%) and H⋅⋅⋅S/S⋅⋅⋅H (9.2%) intermolecular contacts, with the surface being mapped over the dnorm, shape-index and curvedness properties.},
url = {https://hdl.handle.net/20.500.11811/14325}
}
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