Structural relationships in the solid state of the anti-chagas agent (<Emphasis Type="Italic">E</Emphasis>)-phenylethenylbenzofuroxan |
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Authors: | Felipe Terra Martins Alejandro Pedro Ayala Williams Porcal Hugo Cerecetto Mercedes González and Javier Ellena |
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Institution: | 1.Instituto de Física de S?o Carlos,Universidade de S?o Paulo,Sao Carlos,Brazil;2.Departamento de Física,Universidade Federal do Ceará,Fortaleza,Brazil;3.Departamento de Química Organica, Facultad de Ciencias-Facultad de Química,Universidad de la República,Montevideo,Uruguay |
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Abstract: | The crystal structure and the vibrational spectrum of a potential drug for Chagas‘s disease treatment, the (E)-isomer of phenylethenylbenzofuroxan 1 (5(6)(E)-(2-phenylethenyl)]benzo1,2-c]1,2,5-oxadiazole N-oxide), are reported. In order to provide insights into structural relationships, quantum mechanical calculations were employed
starting from crystal structure. These results have given theoretical support to state interesting structural features, such
as the effect of some intermolecular contacts on the molecule conformation and the electronic delocalization decreasing through
atoms of the benzofuroxan moiety. Furthermore, the MOGUL comparative analysis in the Cambridge Structural Database provided
additional evidences on these structural behaviors of compound 1. Intermolecular contacts interfere on the intramolecular geometry, as, for instance, on the phenyl group orientation, which
is twisted by 12.32(6)° from the ethenylbenzofuroxan plane. The experimental Raman spectrum of compound 1 presents unexpected frequency shift and also anomalous Raman activities. At last, the molecule skeleton deformation and the
characteristic vibrational modes were correlated by matching the experimental Raman spectrum to the calculated one. |
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