Synthesis, crystal structure, Hirshfeld surface analysis and energy framework calculations of trans-3,7,9,9-tetramethyl-10-(prop-2-yn-1-yl)-1,2,3,4,4a,9,9a,10-octahydroacridine

Synthesis, crystal structure, Hirshfeld surface analysis and energy framework calculations of trans-3,7,9,9-tetramethyl-10-(prop-2-yn-1-yl)-1,2,3,4,4a,9,9a,10-octahydroacridine

The title heterocyclic compound, C20H27N, has been prepared in good yield (72%) via a BiCl3-catalyzed cationic Povarov reaction between N-propargyl-4-methylaniline and (±)-citronellal. The X-ray single-crystal study indicates that the structure consists of molecules connected by C—H...π contacts to...

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Main Authors: Mauricio Acelas, Analio Dugarte-Dugarte, Arnold R. Romero Bohórquez, José Antonio Henao, José Miguel Delgado, Graciela Díaz de Delgado
Format: Article
Language:English
Published: International Union of Crystallography 2021-03-01
Series:Acta Crystallographica Section E: Crystallographic Communications
Subjects:
octahydroacridine
povarov reaction
hirshfeld surface
energy frameworks
dft calculations
spectroscopic characterization
crystal structure
Online Access:http://scripts.iucr.org/cgi-bin/paper?S2056989021001183
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spelling doaj-298799f03ade41caab91ed0fe712aa682021-04-22T11:23:32ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902021-03-0177322623210.1107/S2056989021001183hb7966Synthesis, crystal structure, Hirshfeld surface analysis and energy framework calculations of trans-3,7,9,9-tetramethyl-10-(prop-2-yn-1-yl)-1,2,3,4,4a,9,9a,10-octahydroacridineMauricio Acelas0Analio Dugarte-Dugarte1Arnold R. Romero Bohórquez2José Antonio Henao3José Miguel Delgado4Graciela Díaz de Delgado5Grupo de Investigación en Compuestos Orgánicos de Interés Medicinal (CODEIM), Parque Tecnológico Guatiguará, Universidad Industrial de Santander, Piedecuesta, ColombiaLaboratorio de Cristalografía-LNDRX, Departamento de Química, Facultad de Ciencias, Universidad de los Andes, Mérida, VenezuelaGrupo de Investigación en Compuestos Orgánicos de Interés Medicinal (CODEIM), Parque Tecnológico Guatiguará, Universidad Industrial de Santander, Piedecuesta, ColombiaGrupo de Investigación en Química Estructural (GIQUE), Escuela de Química, Facultad de Ciencias, Universidad Industrial de Santander, Bucaramanga, ColombiaLaboratorio de Cristalografía-LNDRX, Departamento de Química, Facultad de Ciencias, Universidad de los Andes, Mérida, VenezuelaLaboratorio de Cristalografía-LNDRX, Departamento de Química, Facultad de Ciencias, Universidad de los Andes, Mérida, VenezuelaThe title heterocyclic compound, C20H27N, has been prepared in good yield (72%) via a BiCl3-catalyzed cationic Povarov reaction between N-propargyl-4-methylaniline and (±)-citronellal. The X-ray single-crystal study indicates that the structure consists of molecules connected by C—H...π contacts to produce chains, which pack in a sandwich–herringbone fashion along the b-axis direction. Hirshfeld surface analysis indicates that H...H interactions dominate by contributing 79.1% to the total surface. Energy frameworks and DFT calculations indicate a major contribution of dispersive forces to the total interaction energy.http://scripts.iucr.org/cgi-bin/paper?S2056989021001183octahydroacridinepovarov reactionhirshfeld surfaceenergy frameworksdft calculationsspectroscopic characterizationcrystal structure
collection DOAJ
language English
format Article
sources DOAJ
author Mauricio Acelas
Analio Dugarte-Dugarte
Arnold R. Romero Bohórquez
José Antonio Henao
José Miguel Delgado
Graciela Díaz de Delgado
spellingShingle Mauricio Acelas
Analio Dugarte-Dugarte
Arnold R. Romero Bohórquez
José Antonio Henao
José Miguel Delgado
Graciela Díaz de Delgado
Synthesis, crystal structure, Hirshfeld surface analysis and energy framework calculations of trans-3,7,9,9-tetramethyl-10-(prop-2-yn-1-yl)-1,2,3,4,4a,9,9a,10-octahydroacridine
Acta Crystallographica Section E: Crystallographic Communications
octahydroacridine
povarov reaction
hirshfeld surface
energy frameworks
dft calculations
spectroscopic characterization
crystal structure
author_facet Mauricio Acelas
Analio Dugarte-Dugarte
Arnold R. Romero Bohórquez
José Antonio Henao
José Miguel Delgado
Graciela Díaz de Delgado
author_sort Mauricio Acelas
title Synthesis, crystal structure, Hirshfeld surface analysis and energy framework calculations of trans-3,7,9,9-tetramethyl-10-(prop-2-yn-1-yl)-1,2,3,4,4a,9,9a,10-octahydroacridine
title_short Synthesis, crystal structure, Hirshfeld surface analysis and energy framework calculations of trans-3,7,9,9-tetramethyl-10-(prop-2-yn-1-yl)-1,2,3,4,4a,9,9a,10-octahydroacridine
title_full Synthesis, crystal structure, Hirshfeld surface analysis and energy framework calculations of trans-3,7,9,9-tetramethyl-10-(prop-2-yn-1-yl)-1,2,3,4,4a,9,9a,10-octahydroacridine
title_fullStr Synthesis, crystal structure, Hirshfeld surface analysis and energy framework calculations of trans-3,7,9,9-tetramethyl-10-(prop-2-yn-1-yl)-1,2,3,4,4a,9,9a,10-octahydroacridine
title_full_unstemmed Synthesis, crystal structure, Hirshfeld surface analysis and energy framework calculations of trans-3,7,9,9-tetramethyl-10-(prop-2-yn-1-yl)-1,2,3,4,4a,9,9a,10-octahydroacridine
title_sort synthesis, crystal structure, hirshfeld surface analysis and energy framework calculations of trans-3,7,9,9-tetramethyl-10-(prop-2-yn-1-yl)-1,2,3,4,4a,9,9a,10-octahydroacridine
publisher International Union of Crystallography
series Acta Crystallographica Section E: Crystallographic Communications
issn 2056-9890
publishDate 2021-03-01
description The title heterocyclic compound, C20H27N, has been prepared in good yield (72%) via a BiCl3-catalyzed cationic Povarov reaction between N-propargyl-4-methylaniline and (±)-citronellal. The X-ray single-crystal study indicates that the structure consists of molecules connected by C—H...π contacts to produce chains, which pack in a sandwich–herringbone fashion along the b-axis direction. Hirshfeld surface analysis indicates that H...H interactions dominate by contributing 79.1% to the total surface. Energy frameworks and DFT calculations indicate a major contribution of dispersive forces to the total interaction energy.
topic octahydroacridine
povarov reaction
hirshfeld surface
energy frameworks
dft calculations
spectroscopic characterization
crystal structure
url http://scripts.iucr.org/cgi-bin/paper?S2056989021001183
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