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Abstract:

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.

Registro:

Documento: Artículo
Título:Halogen⋯halogen contacts for the stabilization of a new polymorph of 9,10-dichloroanthracene
Autor:Foi, A.; Corrêa, R.S.; Ellena, J.; Doctorovich, F.; Di Salvo, F.
Filiación:Departamento de Química Inorgánica, Analítica, y Química Física, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, Pabellón 2, Piso 3, C1428EHA Buenos Aires, Argentina
Departamento de Química, Universidade Federal de São Carlos-UFSCar, Rodovia Washington Luis, KM 235 CP 676, CEP 13561-901, São Carlos, SP, Brazil
Instituto de Física de São Carlos, Universidade de São Paulo, CP 369, 13560-970 São Carlos, SP, Brazil
Idioma: Inglés
Palabras clave: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
Año:2014
Volumen:1059
Número:1
Página de inicio:1
Página de fin:7
DOI: http://dx.doi.org/10.1016/j.molstruc.2013.11.028
Título revista:Journal of Molecular Structure
Título revista abreviado:J. Mol. Struct.
ISSN:00222860
CODEN:JMOSB
Registro:http://digital.bl.fcen.uba.ar/collection/paper/document/paper_00222860_v1059_n1_p1_Foi

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Citas:

---------- APA ----------
Foi, A., Corrêa, R.S., Ellena, J., Doctorovich, F. & Di Salvo, F. (2014) . Halogen⋯halogen contacts for the stabilization of a new polymorph of 9,10-dichloroanthracene. Journal of Molecular Structure, 1059(1), 1-7.
http://dx.doi.org/10.1016/j.molstruc.2013.11.028
---------- CHICAGO ----------
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" . Journal of Molecular Structure 1059, no. 1 (2014) : 1-7.
http://dx.doi.org/10.1016/j.molstruc.2013.11.028
---------- MLA ----------
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" . Journal of Molecular Structure, vol. 1059, no. 1, 2014, pp. 1-7.
http://dx.doi.org/10.1016/j.molstruc.2013.11.028
---------- VANCOUVER ----------
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. J. Mol. Struct. 2014;1059(1):1-7.
http://dx.doi.org/10.1016/j.molstruc.2013.11.028