Abstract:
An unpredicted fourfold screw N—H.O hydrogen bond C(4) motif in a primary dicarboxamide (trans-cyclohexane-1,4-dicarboxamide, C8H14N2O2) was investigated by single-crystal X-ray diffraction and IR and Raman spectroscopies. Electron-density topology and intermolecular energy analyses determined from ab initio calculations were employed to examine the influence of weak C—H.O hydrogen-bond interactions on the peculiar arrangement of molecules in the tetragonal P43212 space group. In addition, the way in which the co-operative effects of those weak bonds might modify their relative influence on molecular packing was estimated from cluster calculations. Based on the results, a structural model is proposed which helps to rationalize the unusual fourfold screw molecular arrangement. © 2018 International Union of Crystallography.
Registro:
Documento: |
Artículo
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Título: | Role of weak C—H…O and strong N—H…O intermolecular interactions on the high-symmetry molecular packing of trans-cyclohexane-1,4-dicarboxamide |
Autor: | Garcí-Reyes, F.; Fantoni, A.C.; Barón, M.; Romano, R.M.; Punte, G.M.; Echeverrí, G.A. |
Filiación: | IFLP (CONICET, CCT–La Plata), Departamento de Física, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, 115 y 49, La Plata, 1900, Argentina Facultad de Ciencias Exactas y Naturales, Universidad de Belgrano, Villanueva 1324, Buenos Aires, 1426, Argentina CEQUINOR (UNLP–CONICET, CCT–La Plata), Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, La Plata, 1900, Argentina Facultad de Ingeniería, Universidad Nacional de La Plata, 115 y 49, La Plata, 1900, Argentina
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Palabras clave: | Ab initio calculations; Carboxamide; Crystal structure; Hydrogen bonds; IR spectroscopy; Raman spectroscopy; Calculations; Crystal structure; Hexane; Infrared spectroscopy; Raman spectroscopy; Screws; Single crystals; Cyclohexane; Ab initio calculations; Carboxamides; Cluster calculations; Co-operative effects; Electron-density topology; IR and Raman spectroscopy; Single crystal x-ray diffraction; Structural modeling; Hydrogen bond interaction; Intermolecular interactions; Molecular arrangements; Hydrogen bonds |
Año: | 2018
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Volumen: | 74
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Número: | 10
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Página de inicio: | 1068
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Página de fin: | 1078
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DOI: |
http://dx.doi.org/10.1107/S2053229618011750 |
Título revista: | Acta Crystallographica Section C: Structural Chemistry
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Título revista abreviado: | Acta crystallogr., C Struct. Chem.
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ISSN: | 20532296
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CODEN: | ACSCG
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_20532296_v74_n10_p1068_GarciReyes |
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Citas:
---------- APA ----------
Garcí-Reyes, F., Fantoni, A.C., Barón, M., Romano, R.M., Punte, G.M. & Echeverrí, G.A.
(2018)
. Role of weak C—H…O and strong N—H…O intermolecular interactions on the high-symmetry molecular packing of trans-cyclohexane-1,4-dicarboxamide. Acta Crystallographica Section C: Structural Chemistry, 74(10), 1068-1078.
http://dx.doi.org/10.1107/S2053229618011750---------- CHICAGO ----------
Garcí-Reyes, F., Fantoni, A.C., Barón, M., Romano, R.M., Punte, G.M., Echeverrí, G.A.
"Role of weak C—H…O and strong N—H…O intermolecular interactions on the high-symmetry molecular packing of trans-cyclohexane-1,4-dicarboxamide"
. Acta Crystallographica Section C: Structural Chemistry 74, no. 10
(2018) : 1068-1078.
http://dx.doi.org/10.1107/S2053229618011750---------- MLA ----------
Garcí-Reyes, F., Fantoni, A.C., Barón, M., Romano, R.M., Punte, G.M., Echeverrí, G.A.
"Role of weak C—H…O and strong N—H…O intermolecular interactions on the high-symmetry molecular packing of trans-cyclohexane-1,4-dicarboxamide"
. Acta Crystallographica Section C: Structural Chemistry, vol. 74, no. 10, 2018, pp. 1068-1078.
http://dx.doi.org/10.1107/S2053229618011750---------- VANCOUVER ----------
Garcí-Reyes, F., Fantoni, A.C., Barón, M., Romano, R.M., Punte, G.M., Echeverrí, G.A. Role of weak C—H…O and strong N—H…O intermolecular interactions on the high-symmetry molecular packing of trans-cyclohexane-1,4-dicarboxamide. Acta crystallogr., C Struct. Chem. 2018;74(10):1068-1078.
http://dx.doi.org/10.1107/S2053229618011750