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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International Union of Crystallography
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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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