Halogen⋯halogen contacts for the stabilization of a new polymorph of 9,10-dichloroanthracene
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, crystalli...
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todo:paper_00222860_v1059_n1_p1_Foi2023-10-03T14:30:30Z Halogen⋯halogen contacts for the stabilization of a new polymorph of 9,10-dichloroanthracene Foi, A. Corrêa, R.S. Ellena, J. Doctorovich, F. Di Salvo, F. 9,10-Dichloroanthracene Cl⋯Cl interactions DFT-D Halogen-bonding Molecular conformation Polymorphism 9,10-Dichloroanthracene DFT-D Dispersion correction Electronic structure calculations Halogen bonding Intermolecular interactions Molecular conformation Stacking interaction Chlorine compounds Electronic structure Hydrogen bonds Polymorphism Chlorine 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. © 2013 Elsevier B.V. All rights reserved. Fil:Ellena, J. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Doctorovich, F. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Di Salvo, F. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00222860_v1059_n1_p1_Foi |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
9,10-Dichloroanthracene Cl⋯Cl interactions DFT-D Halogen-bonding Molecular conformation Polymorphism 9,10-Dichloroanthracene DFT-D Dispersion correction Electronic structure calculations Halogen bonding Intermolecular interactions Molecular conformation Stacking interaction Chlorine compounds Electronic structure Hydrogen bonds Polymorphism Chlorine |
| spellingShingle |
9,10-Dichloroanthracene Cl⋯Cl interactions DFT-D Halogen-bonding Molecular conformation Polymorphism 9,10-Dichloroanthracene DFT-D Dispersion correction Electronic structure calculations Halogen bonding Intermolecular interactions Molecular conformation Stacking interaction Chlorine compounds Electronic structure Hydrogen bonds Polymorphism Chlorine Foi, A. Corrêa, R.S. Ellena, J. Doctorovich, F. Di Salvo, F. Halogen⋯halogen contacts for the stabilization of a new polymorph of 9,10-dichloroanthracene |
| topic_facet |
9,10-Dichloroanthracene Cl⋯Cl interactions DFT-D Halogen-bonding Molecular conformation Polymorphism 9,10-Dichloroanthracene DFT-D Dispersion correction Electronic structure calculations Halogen bonding Intermolecular interactions Molecular conformation Stacking interaction Chlorine compounds Electronic structure Hydrogen bonds Polymorphism Chlorine |
| 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. © 2013 Elsevier B.V. All rights reserved. |
| format |
JOUR |
| author |
Foi, A. Corrêa, R.S. Ellena, J. Doctorovich, F. Di Salvo, F. |
| author_facet |
Foi, A. Corrêa, R.S. Ellena, J. Doctorovich, F. Di Salvo, F. |
| author_sort |
Foi, A. |
| title |
Halogen⋯halogen contacts for the stabilization of a new polymorph of 9,10-dichloroanthracene |
| 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 |
| url |
http://hdl.handle.net/20.500.12110/paper_00222860_v1059_n1_p1_Foi |
| work_keys_str_mv |
AT foia halogenhalogencontactsforthestabilizationofanewpolymorphof910dichloroanthracene AT correars halogenhalogencontactsforthestabilizationofanewpolymorphof910dichloroanthracene AT ellenaj halogenhalogencontactsforthestabilizationofanewpolymorphof910dichloroanthracene AT doctorovichf halogenhalogencontactsforthestabilizationofanewpolymorphof910dichloroanthracene AT disalvof halogenhalogencontactsforthestabilizationofanewpolymorphof910dichloroanthracene |
| _version_ |
1782028656446537728 |