Synthesis, crystal structure and Hirshfeld surface analysis of sulfamethoxazolium methylsulfate monohydrate

Autores
Moroni, Aldana Beatriz; Bottoso, Tiago; Lionello, Diego Fernando; Vega, Daniel R.; Kaufman, Teodoro Saul; Calvo, Natalia Lorena
Año de publicación
2024
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The mol­ecular salt sulfamethoxazolium {or 4-[(5-methyl-1,2-oxazol-3-yl)sulf­amo­yl]anilinium methyl sulfate monohydrate}, C10H12N3O3S+·CH3O4S−·H2O, was prepared by the reaction of sulfamethoxazole and H2SO4 in methanol and crystallized from methanol–ether–water. Protonation takes place at the nitro­gen atom of the primary amino group. In the crystal, N—H⋯O hydrogen bonds (water and methyl­sulfate anion) and inter­molecular N—H⋯N inter­actions involving the sulfonamide and isoxazole nitro­gen atoms, link the components into a tri-dimensional network, additional cohesion being provided by face-to-face π–π inter­actions between the phenyl rings of adjacent mol­ecules. A Hirshfeld surface analysis was used to verify the contributions of the different inter­molecular inter­actions, showing that the three most important contributions for the crystal packing are from H⋯O (54.1%), H⋯H (29.2%) and H⋯N (5.0%) inter­actions.
Fil: Moroni, Aldana Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Bottoso, Tiago. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas.; Argentina
Fil: Lionello, Diego Fernando. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Comisión Nacional de Energía Atómica; Argentina
Fil: Vega, Daniel R.. Comisión Nacional de Energía Atómica; Argentina
Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Calvo, Natalia Lorena. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Materia
CRYSTAL STRUCTURE
HYDROGEN BONDING
METHYL SULFATE
MOLECULAR SALT
SULFAMETHOXAZOLIUM
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/263621
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/263621
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis, crystal structure and Hirshfeld surface analysis of sulfamethoxazolium methylsulfate monohydrateMoroni, Aldana BeatrizBottoso, TiagoLionello, Diego FernandoVega, Daniel R.Kaufman, Teodoro SaulCalvo, Natalia LorenaCRYSTAL STRUCTUREHYDROGEN BONDINGMETHYL SULFATEMOLECULAR SALTSULFAMETHOXAZOLIUMhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The mol­ecular salt sulfamethoxazolium {or 4-[(5-methyl-1,2-oxazol-3-yl)sulf­amo­yl]anilinium methyl sulfate monohydrate}, C10H12N3O3S+·CH3O4S−·H2O, was prepared by the reaction of sulfamethoxazole and H2SO4 in methanol and crystallized from methanol–ether–water. Protonation takes place at the nitro­gen atom of the primary amino group. In the crystal, N—H⋯O hydrogen bonds (water and methyl­sulfate anion) and inter­molecular N—H⋯N inter­actions involving the sulfonamide and isoxazole nitro­gen atoms, link the components into a tri-dimensional network, additional cohesion being provided by face-to-face π–π inter­actions between the phenyl rings of adjacent mol­ecules. A Hirshfeld surface analysis was used to verify the contributions of the different inter­molecular inter­actions, showing that the three most important contributions for the crystal packing are from H⋯O (54.1%), H⋯H (29.2%) and H⋯N (5.0%) inter­actions.Fil: Moroni, Aldana Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Bottoso, Tiago. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas.; ArgentinaFil: Lionello, Diego Fernando. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Comisión Nacional de Energía Atómica; ArgentinaFil: Vega, Daniel R.. Comisión Nacional de Energía Atómica; ArgentinaFil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Calvo, Natalia Lorena. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaInternational Union of Crystallography2024-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/263621Moroni, Aldana Beatriz; Bottoso, Tiago; Lionello, Diego Fernando; Vega, Daniel R.; Kaufman, Teodoro Saul; et al.; Synthesis, crystal structure and Hirshfeld surface analysis of sulfamethoxazolium methylsulfate monohydrate; International Union of Crystallography; Acta Crystallographica Section E Crystallographic Communications; 80; 10; 9-2024; 1064-10682056-9890CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://journals.iucr.org/paper?S2056989024009204info:eu-repo/semantics/altIdentifier/doi/10.1107/S2056989024009204info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:26:35Zoai:ri.conicet.gov.ar:11336/263621instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-10-15 14:26:35.532CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis, crystal structure and Hirshfeld surface analysis of sulfamethoxazolium methylsulfate monohydrate
title Synthesis, crystal structure and Hirshfeld surface analysis of sulfamethoxazolium methylsulfate monohydrate
spellingShingle Synthesis, crystal structure and Hirshfeld surface analysis of sulfamethoxazolium methylsulfate monohydrate
Moroni, Aldana Beatriz
CRYSTAL STRUCTURE
HYDROGEN BONDING
METHYL SULFATE
MOLECULAR SALT
SULFAMETHOXAZOLIUM
title_short Synthesis, crystal structure and Hirshfeld surface analysis of sulfamethoxazolium methylsulfate monohydrate
title_full Synthesis, crystal structure and Hirshfeld surface analysis of sulfamethoxazolium methylsulfate monohydrate
title_fullStr Synthesis, crystal structure and Hirshfeld surface analysis of sulfamethoxazolium methylsulfate monohydrate
title_full_unstemmed Synthesis, crystal structure and Hirshfeld surface analysis of sulfamethoxazolium methylsulfate monohydrate
title_sort Synthesis, crystal structure and Hirshfeld surface analysis of sulfamethoxazolium methylsulfate monohydrate
dc.creator.none.fl_str_mv Moroni, Aldana Beatriz
Bottoso, Tiago
Lionello, Diego Fernando
Vega, Daniel R.
Kaufman, Teodoro Saul
Calvo, Natalia Lorena
author Moroni, Aldana Beatriz
author_facet Moroni, Aldana Beatriz
Bottoso, Tiago
Lionello, Diego Fernando
Vega, Daniel R.
Kaufman, Teodoro Saul
Calvo, Natalia Lorena
author_role author
author2 Bottoso, Tiago
Lionello, Diego Fernando
Vega, Daniel R.
Kaufman, Teodoro Saul
Calvo, Natalia Lorena
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv CRYSTAL STRUCTURE
HYDROGEN BONDING
METHYL SULFATE
MOLECULAR SALT
SULFAMETHOXAZOLIUM
topic CRYSTAL STRUCTURE
HYDROGEN BONDING
METHYL SULFATE
MOLECULAR SALT
SULFAMETHOXAZOLIUM
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The mol­ecular salt sulfamethoxazolium {or 4-[(5-methyl-1,2-oxazol-3-yl)sulf­amo­yl]anilinium methyl sulfate monohydrate}, C10H12N3O3S+·CH3O4S−·H2O, was prepared by the reaction of sulfamethoxazole and H2SO4 in methanol and crystallized from methanol–ether–water. Protonation takes place at the nitro­gen atom of the primary amino group. In the crystal, N—H⋯O hydrogen bonds (water and methyl­sulfate anion) and inter­molecular N—H⋯N inter­actions involving the sulfonamide and isoxazole nitro­gen atoms, link the components into a tri-dimensional network, additional cohesion being provided by face-to-face π–π inter­actions between the phenyl rings of adjacent mol­ecules. A Hirshfeld surface analysis was used to verify the contributions of the different inter­molecular inter­actions, showing that the three most important contributions for the crystal packing are from H⋯O (54.1%), H⋯H (29.2%) and H⋯N (5.0%) inter­actions.
Fil: Moroni, Aldana Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Bottoso, Tiago. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas.; Argentina
Fil: Lionello, Diego Fernando. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Comisión Nacional de Energía Atómica; Argentina
Fil: Vega, Daniel R.. Comisión Nacional de Energía Atómica; Argentina
Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Calvo, Natalia Lorena. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
description The mol­ecular salt sulfamethoxazolium {or 4-[(5-methyl-1,2-oxazol-3-yl)sulf­amo­yl]anilinium methyl sulfate monohydrate}, C10H12N3O3S+·CH3O4S−·H2O, was prepared by the reaction of sulfamethoxazole and H2SO4 in methanol and crystallized from methanol–ether–water. Protonation takes place at the nitro­gen atom of the primary amino group. In the crystal, N—H⋯O hydrogen bonds (water and methyl­sulfate anion) and inter­molecular N—H⋯N inter­actions involving the sulfonamide and isoxazole nitro­gen atoms, link the components into a tri-dimensional network, additional cohesion being provided by face-to-face π–π inter­actions between the phenyl rings of adjacent mol­ecules. A Hirshfeld surface analysis was used to verify the contributions of the different inter­molecular inter­actions, showing that the three most important contributions for the crystal packing are from H⋯O (54.1%), H⋯H (29.2%) and H⋯N (5.0%) inter­actions.
publishDate 2024
dc.date.none.fl_str_mv 2024-09
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/263621
Moroni, Aldana Beatriz; Bottoso, Tiago; Lionello, Diego Fernando; Vega, Daniel R.; Kaufman, Teodoro Saul; et al.; Synthesis, crystal structure and Hirshfeld surface analysis of sulfamethoxazolium methylsulfate monohydrate; International Union of Crystallography; Acta Crystallographica Section E Crystallographic Communications; 80; 10; 9-2024; 1064-1068
2056-9890
CONICET Digital
CONICET
url http://hdl.handle.net/11336/263621
identifier_str_mv Moroni, Aldana Beatriz; Bottoso, Tiago; Lionello, Diego Fernando; Vega, Daniel R.; Kaufman, Teodoro Saul; et al.; Synthesis, crystal structure and Hirshfeld surface analysis of sulfamethoxazolium methylsulfate monohydrate; International Union of Crystallography; Acta Crystallographica Section E Crystallographic Communications; 80; 10; 9-2024; 1064-1068
2056-9890
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://journals.iucr.org/paper?S2056989024009204
info:eu-repo/semantics/altIdentifier/doi/10.1107/S2056989024009204
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv International Union of Crystallography
publisher.none.fl_str_mv International Union of Crystallography
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1846082712568332288
score 13.22299

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