TY - JOUR
T1 - N-acetyl-5-isopropyl-2-tioxoimidazolidin-4-one
T2 - Synthesis, spectroscopic characterization, crystal structure, DFT calculations, Hirshfeld surface analysis and energy framework study
AU - Delgado, Gerzon E.
AU - Mora, Asiloé J.
AU - Seijas, Luis E.
AU - Almeida, Rafael
AU - Chacón, Cecilia
AU - Azotla-Cruz, Liliana
AU - Cisterna, Jonathan
AU - Cárdenas, Alejandro
AU - Brito, Iván
N1 - Funding Information:
This work was partially done into G.E. Delgado visit at the Universidad de Antofagasta , supported by MINEDUC -UA project, code ANT 1856, Chile. G.E. Delgado thank to FONACIT Venezuela (grant LAB-97000821 ). J. Cisterna, A. Cárdenas and I. Brito thank to Universidad de Antofagasta Chile for purchase license for the Cambridge Structural Database and Amsterdam Density Functional (ADF) software to perform DFT density calculations.
Funding Information:
This work was partially done into G.E. Delgado visit at the Universidad de Antofagasta, supported by MINEDUC-UA project, code ANT 1856, Chile. G.E. Delgado thank to FONACIT Venezuela (grant LAB-97000821). J. Cisterna, A. C?rdenas and I. Brito thank to Universidad de Antofagasta Chile for purchase license for the Cambridge Structural Database and Amsterdam Density Functional (ADF) software to perform DFT density calculations.
Publisher Copyright:
© 2020 Elsevier B.V.
PY - 2020/11/5
Y1 - 2020/11/5
N2 - Studies based on the role of non-covalent interactions in supramolecular structure of materials with pharmacological properties have gained considerable relevance. Herein, we report the structural characterization of a new thiohydantoin compound which are important heterocyclic scaffolds and a class of well-known molecules for their pharmacological properties. N-acetyl-5-isopropyl-2-thioxoimidazolidin-4-one compound has been synthesized and characterized by FT-IR, 1H NMR and 13C NMR spectroscopy. Its crystal structure was also determined by single-crystal X-ray diffraction studies. This material crystallizes in the triclinic system with space group P1¯(N°2), Z = 4, with two independent molecules in the asymmetric unit. The crystal packing is governed by N–H⋯O hydrogen bond-type intermolecular interactions, forming infinite one-dimensional chains with graph-set motif C(6). The manifestations of cooperative effects in the formation of supramolecular synthons observed were analyzed from the fully optimized clusters employing a DFT/B3LYP level of calculations, which reproduce the main features of the stereochemistry and geometries of the synthons exhibited by X-ray diffraction. Additionally, these intermolecular interactions were analyzed using Hirshfeld surfaces analysis, 2D finger print plots, shape index topological surfaces and 3D energy framework (crystal packing in terms on energy).
AB - Studies based on the role of non-covalent interactions in supramolecular structure of materials with pharmacological properties have gained considerable relevance. Herein, we report the structural characterization of a new thiohydantoin compound which are important heterocyclic scaffolds and a class of well-known molecules for their pharmacological properties. N-acetyl-5-isopropyl-2-thioxoimidazolidin-4-one compound has been synthesized and characterized by FT-IR, 1H NMR and 13C NMR spectroscopy. Its crystal structure was also determined by single-crystal X-ray diffraction studies. This material crystallizes in the triclinic system with space group P1¯(N°2), Z = 4, with two independent molecules in the asymmetric unit. The crystal packing is governed by N–H⋯O hydrogen bond-type intermolecular interactions, forming infinite one-dimensional chains with graph-set motif C(6). The manifestations of cooperative effects in the formation of supramolecular synthons observed were analyzed from the fully optimized clusters employing a DFT/B3LYP level of calculations, which reproduce the main features of the stereochemistry and geometries of the synthons exhibited by X-ray diffraction. Additionally, these intermolecular interactions were analyzed using Hirshfeld surfaces analysis, 2D finger print plots, shape index topological surfaces and 3D energy framework (crystal packing in terms on energy).
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U2 - 10.1016/j.molstruc.2020.128630
DO - 10.1016/j.molstruc.2020.128630
M3 - Research Article
AN - SCOPUS:85086309884
SN - 0022-2860
VL - 1219
JO - Journal of Molecular Structure
JF - Journal of Molecular Structure
M1 - 128630
ER -