Supramolecular self-assembly of a coumarine-based acylthiourea synthon directed by π-stacking interactions: Crystal structure and Hirshfeld surface analysis

Autores
Saeed, Aamer; Ashraf, Saba; Flörke, Ulrich; Delgado Espinoza, Zuly Yuliana; Erben, Mauricio Federico; Pérez, Hiram
Año de publicación
2016
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The structure of 1-(2-oxo-2H-chromene-3-carbonyl)-3-(2-methoxy-phenyl)thiourea (1) has been determined by single-crystal X-ray crystallography. This compound crystallizes in the monoclinic space group P21/c with a = 7.455 (2) Å, b = 12.744 (3) Å, c = 16.892 (4) Å, β = 90.203 (6)° and Z = 4. Both, the coumarin and the phenyl rings are nearly coplanar with the central 1-acylthiourea group, with the CO and CS bonds adopting an opposite orientation. Intramolecular N–H···O, C–H···O, and C–H···S hydrogen bonds are favored by the planar conformation. The molecules are packed through C–H···O, C–H···S and C–H···C hydrogen bonds, and two π···π interactions with offset arrangement. Inter-centroid distance of 3.490 (2) Å, slip angles of 18.5 and 20.9°, and vertical displacements of 1.10 and 1.24 Å are the stacking parameters corresponding to the stronger π···π interaction. Hirshfeld surface analysis was performed for visualizing, exploring and quantifying intermolecular interactions in the crystal lattice of compound 1, and compared with two closely related species. Shape index and Curvedness surfaces indicated π-stacking with different features in opposed sides of the molecule. Fingerprint plot showed C···C contacts with similar contributions to the crystal packing in comparison with those associated to hydrogen bonds. Enrichment ratios for H···H, O···H, S···H and C···C contacts revealed a high propensity to form in the crystal.
Fil: Saeed, Aamer. Quaid-I-Azam University; Pakistán
Fil: Ashraf, Saba. Quaid-I-Azam University; Pakistán
Fil: Flörke, Ulrich. University of Paderborn; Alemania
Fil: Delgado Espinoza, Zuly Yuliana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Fil: Erben, Mauricio Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Fil: Pérez, Hiram. Universidad de La Habana; Cuba
Materia
Thiourea
Coumarine
Crystal Structure
Hydrogen Bonding
Π-Stacking
Hirshfeld Surface Analysis
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/48251
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/48251
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Supramolecular self-assembly of a coumarine-based acylthiourea synthon directed by π-stacking interactions: Crystal structure and Hirshfeld surface analysisSaeed, AamerAshraf, SabaFlörke, UlrichDelgado Espinoza, Zuly YulianaErben, Mauricio FedericoPérez, HiramThioureaCoumarineCrystal StructureHydrogen BondingΠ-StackingHirshfeld Surface Analysishttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The structure of 1-(2-oxo-2H-chromene-3-carbonyl)-3-(2-methoxy-phenyl)thiourea (1) has been determined by single-crystal X-ray crystallography. This compound crystallizes in the monoclinic space group P21/c with a = 7.455 (2) Å, b = 12.744 (3) Å, c = 16.892 (4) Å, β = 90.203 (6)° and Z = 4. Both, the coumarin and the phenyl rings are nearly coplanar with the central 1-acylthiourea group, with the CO and CS bonds adopting an opposite orientation. Intramolecular N–H···O, C–H···O, and C–H···S hydrogen bonds are favored by the planar conformation. The molecules are packed through C–H···O, C–H···S and C–H···C hydrogen bonds, and two π···π interactions with offset arrangement. Inter-centroid distance of 3.490 (2) Å, slip angles of 18.5 and 20.9°, and vertical displacements of 1.10 and 1.24 Å are the stacking parameters corresponding to the stronger π···π interaction. Hirshfeld surface analysis was performed for visualizing, exploring and quantifying intermolecular interactions in the crystal lattice of compound 1, and compared with two closely related species. Shape index and Curvedness surfaces indicated π-stacking with different features in opposed sides of the molecule. Fingerprint plot showed C···C contacts with similar contributions to the crystal packing in comparison with those associated to hydrogen bonds. Enrichment ratios for H···H, O···H, S···H and C···C contacts revealed a high propensity to form in the crystal.Fil: Saeed, Aamer. Quaid-I-Azam University; PakistánFil: Ashraf, Saba. Quaid-I-Azam University; PakistánFil: Flörke, Ulrich. University of Paderborn; AlemaniaFil: Delgado Espinoza, Zuly Yuliana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; ArgentinaFil: Erben, Mauricio Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; ArgentinaFil: Pérez, Hiram. Universidad de La Habana; CubaElsevier Science2016-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/48251Saeed, Aamer; Ashraf, Saba; Flörke, Ulrich; Delgado Espinoza, Zuly Yuliana; Erben, Mauricio Federico; et al.; Supramolecular self-assembly of a coumarine-based acylthiourea synthon directed by π-stacking interactions: Crystal structure and Hirshfeld surface analysis; Elsevier Science; Journal of Molecular Structure; 1111; 5-2016; 76-830022-2860CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2016.01.074info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0022286016300746info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:56:07Zoai:ri.conicet.gov.ar:11336/48251instacron: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:34982025-09-29 09:56:07.406CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Supramolecular self-assembly of a coumarine-based acylthiourea synthon directed by π-stacking interactions: Crystal structure and Hirshfeld surface analysis
title Supramolecular self-assembly of a coumarine-based acylthiourea synthon directed by π-stacking interactions: Crystal structure and Hirshfeld surface analysis
spellingShingle Supramolecular self-assembly of a coumarine-based acylthiourea synthon directed by π-stacking interactions: Crystal structure and Hirshfeld surface analysis
Saeed, Aamer
Thiourea
Coumarine
Crystal Structure
Hydrogen Bonding
Π-Stacking
Hirshfeld Surface Analysis
title_short Supramolecular self-assembly of a coumarine-based acylthiourea synthon directed by π-stacking interactions: Crystal structure and Hirshfeld surface analysis
title_full Supramolecular self-assembly of a coumarine-based acylthiourea synthon directed by π-stacking interactions: Crystal structure and Hirshfeld surface analysis
title_fullStr Supramolecular self-assembly of a coumarine-based acylthiourea synthon directed by π-stacking interactions: Crystal structure and Hirshfeld surface analysis
title_full_unstemmed Supramolecular self-assembly of a coumarine-based acylthiourea synthon directed by π-stacking interactions: Crystal structure and Hirshfeld surface analysis
title_sort Supramolecular self-assembly of a coumarine-based acylthiourea synthon directed by π-stacking interactions: Crystal structure and Hirshfeld surface analysis
dc.creator.none.fl_str_mv Saeed, Aamer
Ashraf, Saba
Flörke, Ulrich
Delgado Espinoza, Zuly Yuliana
Erben, Mauricio Federico
Pérez, Hiram
author Saeed, Aamer
author_facet Saeed, Aamer
Ashraf, Saba
Flörke, Ulrich
Delgado Espinoza, Zuly Yuliana
Erben, Mauricio Federico
Pérez, Hiram
author_role author
author2 Ashraf, Saba
Flörke, Ulrich
Delgado Espinoza, Zuly Yuliana
Erben, Mauricio Federico
Pérez, Hiram
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Thiourea
Coumarine
Crystal Structure
Hydrogen Bonding
Π-Stacking
Hirshfeld Surface Analysis
topic Thiourea
Coumarine
Crystal Structure
Hydrogen Bonding
Π-Stacking
Hirshfeld Surface Analysis
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 structure of 1-(2-oxo-2H-chromene-3-carbonyl)-3-(2-methoxy-phenyl)thiourea (1) has been determined by single-crystal X-ray crystallography. This compound crystallizes in the monoclinic space group P21/c with a = 7.455 (2) Å, b = 12.744 (3) Å, c = 16.892 (4) Å, β = 90.203 (6)° and Z = 4. Both, the coumarin and the phenyl rings are nearly coplanar with the central 1-acylthiourea group, with the CO and CS bonds adopting an opposite orientation. Intramolecular N–H···O, C–H···O, and C–H···S hydrogen bonds are favored by the planar conformation. The molecules are packed through C–H···O, C–H···S and C–H···C hydrogen bonds, and two π···π interactions with offset arrangement. Inter-centroid distance of 3.490 (2) Å, slip angles of 18.5 and 20.9°, and vertical displacements of 1.10 and 1.24 Å are the stacking parameters corresponding to the stronger π···π interaction. Hirshfeld surface analysis was performed for visualizing, exploring and quantifying intermolecular interactions in the crystal lattice of compound 1, and compared with two closely related species. Shape index and Curvedness surfaces indicated π-stacking with different features in opposed sides of the molecule. Fingerprint plot showed C···C contacts with similar contributions to the crystal packing in comparison with those associated to hydrogen bonds. Enrichment ratios for H···H, O···H, S···H and C···C contacts revealed a high propensity to form in the crystal.
Fil: Saeed, Aamer. Quaid-I-Azam University; Pakistán
Fil: Ashraf, Saba. Quaid-I-Azam University; Pakistán
Fil: Flörke, Ulrich. University of Paderborn; Alemania
Fil: Delgado Espinoza, Zuly Yuliana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Fil: Erben, Mauricio Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Fil: Pérez, Hiram. Universidad de La Habana; Cuba
description The structure of 1-(2-oxo-2H-chromene-3-carbonyl)-3-(2-methoxy-phenyl)thiourea (1) has been determined by single-crystal X-ray crystallography. This compound crystallizes in the monoclinic space group P21/c with a = 7.455 (2) Å, b = 12.744 (3) Å, c = 16.892 (4) Å, β = 90.203 (6)° and Z = 4. Both, the coumarin and the phenyl rings are nearly coplanar with the central 1-acylthiourea group, with the CO and CS bonds adopting an opposite orientation. Intramolecular N–H···O, C–H···O, and C–H···S hydrogen bonds are favored by the planar conformation. The molecules are packed through C–H···O, C–H···S and C–H···C hydrogen bonds, and two π···π interactions with offset arrangement. Inter-centroid distance of 3.490 (2) Å, slip angles of 18.5 and 20.9°, and vertical displacements of 1.10 and 1.24 Å are the stacking parameters corresponding to the stronger π···π interaction. Hirshfeld surface analysis was performed for visualizing, exploring and quantifying intermolecular interactions in the crystal lattice of compound 1, and compared with two closely related species. Shape index and Curvedness surfaces indicated π-stacking with different features in opposed sides of the molecule. Fingerprint plot showed C···C contacts with similar contributions to the crystal packing in comparison with those associated to hydrogen bonds. Enrichment ratios for H···H, O···H, S···H and C···C contacts revealed a high propensity to form in the crystal.
publishDate 2016
dc.date.none.fl_str_mv 2016-05
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/11336/48251
Saeed, Aamer; Ashraf, Saba; Flörke, Ulrich; Delgado Espinoza, Zuly Yuliana; Erben, Mauricio Federico; et al.; Supramolecular self-assembly of a coumarine-based acylthiourea synthon directed by π-stacking interactions: Crystal structure and Hirshfeld surface analysis; Elsevier Science; Journal of Molecular Structure; 1111; 5-2016; 76-83
0022-2860
CONICET Digital
CONICET
url http://hdl.handle.net/11336/48251
identifier_str_mv Saeed, Aamer; Ashraf, Saba; Flörke, Ulrich; Delgado Espinoza, Zuly Yuliana; Erben, Mauricio Federico; et al.; Supramolecular self-assembly of a coumarine-based acylthiourea synthon directed by π-stacking interactions: Crystal structure and Hirshfeld surface analysis; Elsevier Science; Journal of Molecular Structure; 1111; 5-2016; 76-83
0022-2860
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2016.01.074
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0022286016300746
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science
publisher.none.fl_str_mv Elsevier Science
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
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score 13.070432

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