Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 5,5-diphenyl-1,3-bis(prop-2-yn-1-yl)imidazolidine-2,4-dione

The title compound, C21H16N2O2, consists of an imidazolidine unit linked to two phenyl rings and two prop-2-yn-1-yl moieties. The imidazolidine ring is oriented at dihedral angles of 79.10 (5) and 82.61 (5)° with respect to the phenyl rings, while the dihedral angle between the two phenyl rings is 6...

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Main Authors: Ismail Ghandour, Abdelouahed Bouayad, Tuncer Hökelek, Amal Haoudi, Frédéric Capet, Catherine Renard, Youssef Kandri Rodi
Format: Article
Language:English
Published: International Union of Crystallography 2019-07-01
Series:Acta Crystallographica Section E: Crystallographic Communications
Subjects:
Online Access:http://scripts.iucr.org/cgi-bin/paper?S2056989019007801
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spelling doaj-55b00cb2a7984875b7e00c4f969b328b2020-11-25T00:25:24ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902019-07-0175795195610.1107/S2056989019007801lh5908Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 5,5-diphenyl-1,3-bis(prop-2-yn-1-yl)imidazolidine-2,4-dioneIsmail Ghandour0Abdelouahed Bouayad1Tuncer Hökelek2Amal Haoudi3Frédéric Capet4Catherine Renard5Youssef Kandri Rodi6Laboratoire de Chimie de la Matière Condensée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Immouzzer, BP 2202, Fez, MoroccoLaboratoire de Chimie de la Matière Condensée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Immouzzer, BP 2202, Fez, MoroccoDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, TurkeyLaboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Immouzzer, BP 2202, Fez, MoroccoUnité de Catalyse et de Chimie du Solide (UCCS), UMR 8181, Ecole Nationale Supérieure de Chimie de Lille, Université Lille 1, 59650 Villeneuve, d'Ascq, Cedex, FranceUnité de Catalyse et de Chimie du Solide (UCCS), UMR 8181, Ecole Nationale Supérieure de Chimie de Lille, Université Lille 1, 59650 Villeneuve, d'Ascq, Cedex, FranceLaboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Immouzzer, BP 2202, Fez, MoroccoThe title compound, C21H16N2O2, consists of an imidazolidine unit linked to two phenyl rings and two prop-2-yn-1-yl moieties. The imidazolidine ring is oriented at dihedral angles of 79.10 (5) and 82.61 (5)° with respect to the phenyl rings, while the dihedral angle between the two phenyl rings is 62.06 (5)°. In the crystal, intermolecular C—HProp...OImdzln (Prop = prop-2-yn-1-yl and Imdzln = imidazolidine) hydrogen bonds link the molecules into infinite chains along the b-axis direction. Two weak C—HPhen...π interactions are also observed. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (43.3%), H...C/C...H (37.8%) and H...O/O...H (18.0%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Computational chemistry indicates that the C—HProp...OImdzln hydrogen-bond energy in the crystal is −40.7 kJ mol−1. Density functional theory (DFT) optimized structures at the B3LYP/6–311G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.http://scripts.iucr.org/cgi-bin/paper?S2056989019007801crystal structureimidazolidineoxazoleπ-stackingHirshfeld surface
collection DOAJ
language English
format Article
sources DOAJ
author Ismail Ghandour
Abdelouahed Bouayad
Tuncer Hökelek
Amal Haoudi
Frédéric Capet
Catherine Renard
Youssef Kandri Rodi
spellingShingle Ismail Ghandour
Abdelouahed Bouayad
Tuncer Hökelek
Amal Haoudi
Frédéric Capet
Catherine Renard
Youssef Kandri Rodi
Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 5,5-diphenyl-1,3-bis(prop-2-yn-1-yl)imidazolidine-2,4-dione
Acta Crystallographica Section E: Crystallographic Communications
crystal structure
imidazolidine
oxazole
π-stacking
Hirshfeld surface
author_facet Ismail Ghandour
Abdelouahed Bouayad
Tuncer Hökelek
Amal Haoudi
Frédéric Capet
Catherine Renard
Youssef Kandri Rodi
author_sort Ismail Ghandour
title Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 5,5-diphenyl-1,3-bis(prop-2-yn-1-yl)imidazolidine-2,4-dione
title_short Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 5,5-diphenyl-1,3-bis(prop-2-yn-1-yl)imidazolidine-2,4-dione
title_full Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 5,5-diphenyl-1,3-bis(prop-2-yn-1-yl)imidazolidine-2,4-dione
title_fullStr Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 5,5-diphenyl-1,3-bis(prop-2-yn-1-yl)imidazolidine-2,4-dione
title_full_unstemmed Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 5,5-diphenyl-1,3-bis(prop-2-yn-1-yl)imidazolidine-2,4-dione
title_sort crystal structure, hirshfeld surface analysis and interaction energy and dft studies of 5,5-diphenyl-1,3-bis(prop-2-yn-1-yl)imidazolidine-2,4-dione
publisher International Union of Crystallography
series Acta Crystallographica Section E: Crystallographic Communications
issn 2056-9890
publishDate 2019-07-01
description The title compound, C21H16N2O2, consists of an imidazolidine unit linked to two phenyl rings and two prop-2-yn-1-yl moieties. The imidazolidine ring is oriented at dihedral angles of 79.10 (5) and 82.61 (5)° with respect to the phenyl rings, while the dihedral angle between the two phenyl rings is 62.06 (5)°. In the crystal, intermolecular C—HProp...OImdzln (Prop = prop-2-yn-1-yl and Imdzln = imidazolidine) hydrogen bonds link the molecules into infinite chains along the b-axis direction. Two weak C—HPhen...π interactions are also observed. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (43.3%), H...C/C...H (37.8%) and H...O/O...H (18.0%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Computational chemistry indicates that the C—HProp...OImdzln hydrogen-bond energy in the crystal is −40.7 kJ mol−1. Density functional theory (DFT) optimized structures at the B3LYP/6–311G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.
topic crystal structure
imidazolidine
oxazole
π-stacking
Hirshfeld surface
url http://scripts.iucr.org/cgi-bin/paper?S2056989019007801
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