Halogen⋯halogen contacts for the stabilization of a new polymorph of 9,10-dichloroanthracene

Autores
Foi, Maria Ana; Correa, Rodrigo S.; Ellena, Javier; Doctorovich, Fabio; Di Salvo, Florencia
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A new polymorph of 9,10-dichloroanthracene (9,10-DCA) namely as γ form, was obtained. The crystal structure of the γ polymorphic system showed an orthorhombic P212121 space group with a = 3.8957(2) Å, b = 15.9383(5) Å, c = 17.3107(7) Å, α = β = γ = 90°, while the other polymorphs, α and β, crystallized in P21/a and P-1 ones, respectively. The intermolecular geometries of γ form were analyzed showing that the crystalline self-assembly of this new polymorph of the 9,10-DCA is stabilized by non-classical C–H⋯Cl hydrogen bonds, π–π stacking interactions, and mainly by Cl⋯Cl interactions. Structural parameters confirmed the halogen⋯halogen contacts correspond to the Type II geometry. Complementary, electronic structure calculations were performed in other to estimate the energetic contribution of the observed intermolecular interactions in the crystal packing of the new system. Density Functional Theory (DFT) considering empirical dispersion corrections (named as DFT-D) and MP2 correlated very well and showed energy values according to previously reported related compounds (e.g., the energy for the Cl···Cl is −5.37 and −3.25 kcal mol−1 for MP2/6-31+G** and B2PLYP-D/6-31+G**, respectively). On the other hand, and as expected, DFT using B3LYP as functional was not able to describe properly the studied intermolecular interactions. Moreover, it even predicts repulsive energies for most of the analyzed arrangements.
Fil: Foi, Maria Ana. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina
Fil: Correa, Rodrigo S.. Universidade Federal do São Carlos; Brasil
Fil: Ellena, Javier. Universidade de Sao Paulo; Brasil
Fil: Doctorovich, Fabio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina
Fil: Di Salvo, Florencia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina
Materia
Dichloroanthracene
Polymorphism
Molecular Conformation
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/30480
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/30480
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Halogen⋯halogen contacts for the stabilization of a new polymorph of 9,10-dichloroanthraceneFoi, Maria AnaCorrea, Rodrigo S.Ellena, JavierDoctorovich, FabioDi Salvo, FlorenciaDichloroanthracenePolymorphismMolecular Conformationhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A new polymorph of 9,10-dichloroanthracene (9,10-DCA) namely as γ form, was obtained. The crystal structure of the γ polymorphic system showed an orthorhombic P212121 space group with a = 3.8957(2) Å, b = 15.9383(5) Å, c = 17.3107(7) Å, α = β = γ = 90°, while the other polymorphs, α and β, crystallized in P21/a and P-1 ones, respectively. The intermolecular geometries of γ form were analyzed showing that the crystalline self-assembly of this new polymorph of the 9,10-DCA is stabilized by non-classical C–H⋯Cl hydrogen bonds, π–π stacking interactions, and mainly by Cl⋯Cl interactions. Structural parameters confirmed the halogen⋯halogen contacts correspond to the Type II geometry. Complementary, electronic structure calculations were performed in other to estimate the energetic contribution of the observed intermolecular interactions in the crystal packing of the new system. Density Functional Theory (DFT) considering empirical dispersion corrections (named as DFT-D) and MP2 correlated very well and showed energy values according to previously reported related compounds (e.g., the energy for the Cl···Cl is −5.37 and −3.25 kcal mol−1 for MP2/6-31+G** and B2PLYP-D/6-31+G**, respectively). On the other hand, and as expected, DFT using B3LYP as functional was not able to describe properly the studied intermolecular interactions. Moreover, it even predicts repulsive energies for most of the analyzed arrangements.Fil: Foi, Maria Ana. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; ArgentinaFil: Correa, Rodrigo S.. Universidade Federal do São Carlos; BrasilFil: Ellena, Javier. Universidade de Sao Paulo; BrasilFil: Doctorovich, Fabio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; ArgentinaFil: Di Salvo, Florencia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; ArgentinaElsevier Science2014-02info: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/11336/30480Foi, Maria Ana; Correa, Rodrigo S. ; Ellena, Javier ; Doctorovich, Fabio; Di Salvo, Florencia; Halogen⋯halogen contacts for the stabilization of a new polymorph of 9,10-dichloroanthracene; Elsevier Science; Journal of Molecular Structure; 1059; 2-2014; 1-70022-2860CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.molstruc.2013.11.028info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0022286013009794info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:12:28Zoai:ri.conicet.gov.ar:11336/30480instacron: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 10:12:28.256CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Halogen⋯halogen contacts for the stabilization of a new polymorph of 9,10-dichloroanthracene
title Halogen⋯halogen contacts for the stabilization of a new polymorph of 9,10-dichloroanthracene
spellingShingle Halogen⋯halogen contacts for the stabilization of a new polymorph of 9,10-dichloroanthracene
Foi, Maria Ana
Dichloroanthracene
Polymorphism
Molecular Conformation
title_short Halogen⋯halogen contacts for the stabilization of a new polymorph of 9,10-dichloroanthracene
title_full Halogen⋯halogen contacts for the stabilization of a new polymorph of 9,10-dichloroanthracene
title_fullStr Halogen⋯halogen contacts for the stabilization of a new polymorph of 9,10-dichloroanthracene
title_full_unstemmed Halogen⋯halogen contacts for the stabilization of a new polymorph of 9,10-dichloroanthracene
title_sort Halogen⋯halogen contacts for the stabilization of a new polymorph of 9,10-dichloroanthracene
dc.creator.none.fl_str_mv Foi, Maria Ana
Correa, Rodrigo S.
Ellena, Javier
Doctorovich, Fabio
Di Salvo, Florencia
author Foi, Maria Ana
author_facet Foi, Maria Ana
Correa, Rodrigo S.
Ellena, Javier
Doctorovich, Fabio
Di Salvo, Florencia
author_role author
author2 Correa, Rodrigo S.
Ellena, Javier
Doctorovich, Fabio
Di Salvo, Florencia
author2_role author
author
author
author
dc.subject.none.fl_str_mv Dichloroanthracene
Polymorphism
Molecular Conformation
topic Dichloroanthracene
Polymorphism
Molecular Conformation
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A new polymorph of 9,10-dichloroanthracene (9,10-DCA) namely as γ form, was obtained. The crystal structure of the γ polymorphic system showed an orthorhombic P212121 space group with a = 3.8957(2) Å, b = 15.9383(5) Å, c = 17.3107(7) Å, α = β = γ = 90°, while the other polymorphs, α and β, crystallized in P21/a and P-1 ones, respectively. The intermolecular geometries of γ form were analyzed showing that the crystalline self-assembly of this new polymorph of the 9,10-DCA is stabilized by non-classical C–H⋯Cl hydrogen bonds, π–π stacking interactions, and mainly by Cl⋯Cl interactions. Structural parameters confirmed the halogen⋯halogen contacts correspond to the Type II geometry. Complementary, electronic structure calculations were performed in other to estimate the energetic contribution of the observed intermolecular interactions in the crystal packing of the new system. Density Functional Theory (DFT) considering empirical dispersion corrections (named as DFT-D) and MP2 correlated very well and showed energy values according to previously reported related compounds (e.g., the energy for the Cl···Cl is −5.37 and −3.25 kcal mol−1 for MP2/6-31+G** and B2PLYP-D/6-31+G**, respectively). On the other hand, and as expected, DFT using B3LYP as functional was not able to describe properly the studied intermolecular interactions. Moreover, it even predicts repulsive energies for most of the analyzed arrangements.
Fil: Foi, Maria Ana. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina
Fil: Correa, Rodrigo S.. Universidade Federal do São Carlos; Brasil
Fil: Ellena, Javier. Universidade de Sao Paulo; Brasil
Fil: Doctorovich, Fabio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina
Fil: Di Salvo, Florencia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina
description A new polymorph of 9,10-dichloroanthracene (9,10-DCA) namely as γ form, was obtained. The crystal structure of the γ polymorphic system showed an orthorhombic P212121 space group with a = 3.8957(2) Å, b = 15.9383(5) Å, c = 17.3107(7) Å, α = β = γ = 90°, while the other polymorphs, α and β, crystallized in P21/a and P-1 ones, respectively. The intermolecular geometries of γ form were analyzed showing that the crystalline self-assembly of this new polymorph of the 9,10-DCA is stabilized by non-classical C–H⋯Cl hydrogen bonds, π–π stacking interactions, and mainly by Cl⋯Cl interactions. Structural parameters confirmed the halogen⋯halogen contacts correspond to the Type II geometry. Complementary, electronic structure calculations were performed in other to estimate the energetic contribution of the observed intermolecular interactions in the crystal packing of the new system. Density Functional Theory (DFT) considering empirical dispersion corrections (named as DFT-D) and MP2 correlated very well and showed energy values according to previously reported related compounds (e.g., the energy for the Cl···Cl is −5.37 and −3.25 kcal mol−1 for MP2/6-31+G** and B2PLYP-D/6-31+G**, respectively). On the other hand, and as expected, DFT using B3LYP as functional was not able to describe properly the studied intermolecular interactions. Moreover, it even predicts repulsive energies for most of the analyzed arrangements.
publishDate 2014
dc.date.none.fl_str_mv 2014-02
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/11336/30480
Foi, Maria Ana; Correa, Rodrigo S. ; Ellena, Javier ; Doctorovich, Fabio; Di Salvo, Florencia; Halogen⋯halogen contacts for the stabilization of a new polymorph of 9,10-dichloroanthracene; Elsevier Science; Journal of Molecular Structure; 1059; 2-2014; 1-7
0022-2860
CONICET Digital
CONICET
url http://hdl.handle.net/11336/30480
identifier_str_mv Foi, Maria Ana; Correa, Rodrigo S. ; Ellena, Javier ; Doctorovich, Fabio; Di Salvo, Florencia; Halogen⋯halogen contacts for the stabilization of a new polymorph of 9,10-dichloroanthracene; Elsevier Science; Journal of Molecular Structure; 1059; 2-2014; 1-7
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.2013.11.028
info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0022286013009794
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
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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