Cargando…
6-(2-Chlorobenzyl)-1-(4-chlorophenyl)-7-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one
The title compound, C(19)H(15)Cl(2)N(3)O(2), was obtained by a one-step cyclocondensation of 2-amino-1-(4-chlorophenyl)imidazoline with diethyl (2-chlorobenzyl)malonate under basic conditions. In the crystalline state, the molecule exists as the 7-hydroxy-5-oxo tautomer. The dihedral angles b...
Autores principales: | , , , , , |
---|---|
Formato: | Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2010
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3009369/ https://www.ncbi.nlm.nih.gov/pubmed/21588948 http://dx.doi.org/10.1107/S160053681003919X |
_version_ | 1782194671862153216 |
---|---|
author | Wysocki, Waldemar Matosiuk, Dariusz Rządkowska, Marzena Karczmarzyk, Zbigniew Urbańczyk-Lipkowska, Zofia Kalicki, Przemysław |
author_facet | Wysocki, Waldemar Matosiuk, Dariusz Rządkowska, Marzena Karczmarzyk, Zbigniew Urbańczyk-Lipkowska, Zofia Kalicki, Przemysław |
author_sort | Wysocki, Waldemar |
collection | PubMed |
description | The title compound, C(19)H(15)Cl(2)N(3)O(2), was obtained by a one-step cyclocondensation of 2-amino-1-(4-chlorophenyl)imidazoline with diethyl (2-chlorobenzyl)malonate under basic conditions. In the crystalline state, the molecule exists as the 7-hydroxy-5-oxo tautomer. The dihedral angles between the fused imidazopyrimidine and aromatic chlorophenyl and chlorobenzyl rings are 14.2 (1) and 70.7 (1)°, respectively. The conformation of the molecule is influenced by the intramolecular C—H⋯O and C—H⋯N hydrogen bonds, giving a nearly planar five-ring fused system [maximum deviation from the mean plane = 0.296 (2) Å]. In the crystal structure, strong intermolecular O—H⋯O hydrogen bonds link the molecules into chains along the c axis. These chains are further stabilized by weak C—H⋯Cl and π–π interactions [centroid–centroid distance = 3.6707 (12) Å]. |
format | Text |
id | pubmed-3009369 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2010 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-30093692010-12-30 6-(2-Chlorobenzyl)-1-(4-chlorophenyl)-7-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one Wysocki, Waldemar Matosiuk, Dariusz Rządkowska, Marzena Karczmarzyk, Zbigniew Urbańczyk-Lipkowska, Zofia Kalicki, Przemysław Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(19)H(15)Cl(2)N(3)O(2), was obtained by a one-step cyclocondensation of 2-amino-1-(4-chlorophenyl)imidazoline with diethyl (2-chlorobenzyl)malonate under basic conditions. In the crystalline state, the molecule exists as the 7-hydroxy-5-oxo tautomer. The dihedral angles between the fused imidazopyrimidine and aromatic chlorophenyl and chlorobenzyl rings are 14.2 (1) and 70.7 (1)°, respectively. The conformation of the molecule is influenced by the intramolecular C—H⋯O and C—H⋯N hydrogen bonds, giving a nearly planar five-ring fused system [maximum deviation from the mean plane = 0.296 (2) Å]. In the crystal structure, strong intermolecular O—H⋯O hydrogen bonds link the molecules into chains along the c axis. These chains are further stabilized by weak C—H⋯Cl and π–π interactions [centroid–centroid distance = 3.6707 (12) Å]. International Union of Crystallography 2010-10-09 /pmc/articles/PMC3009369/ /pubmed/21588948 http://dx.doi.org/10.1107/S160053681003919X Text en © Wysocki et al. 2010 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Organic Papers Wysocki, Waldemar Matosiuk, Dariusz Rządkowska, Marzena Karczmarzyk, Zbigniew Urbańczyk-Lipkowska, Zofia Kalicki, Przemysław 6-(2-Chlorobenzyl)-1-(4-chlorophenyl)-7-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one |
title | 6-(2-Chlorobenzyl)-1-(4-chlorophenyl)-7-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one |
title_full | 6-(2-Chlorobenzyl)-1-(4-chlorophenyl)-7-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one |
title_fullStr | 6-(2-Chlorobenzyl)-1-(4-chlorophenyl)-7-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one |
title_full_unstemmed | 6-(2-Chlorobenzyl)-1-(4-chlorophenyl)-7-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one |
title_short | 6-(2-Chlorobenzyl)-1-(4-chlorophenyl)-7-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one |
title_sort | 6-(2-chlorobenzyl)-1-(4-chlorophenyl)-7-hydroxy-2,3-dihydro-1h-imidazo[1,2-a]pyrimidin-5-one |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3009369/ https://www.ncbi.nlm.nih.gov/pubmed/21588948 http://dx.doi.org/10.1107/S160053681003919X |
work_keys_str_mv | AT wysockiwaldemar 62chlorobenzyl14chlorophenyl7hydroxy23dihydro1himidazo12apyrimidin5one AT matosiukdariusz 62chlorobenzyl14chlorophenyl7hydroxy23dihydro1himidazo12apyrimidin5one AT rzadkowskamarzena 62chlorobenzyl14chlorophenyl7hydroxy23dihydro1himidazo12apyrimidin5one AT karczmarzykzbigniew 62chlorobenzyl14chlorophenyl7hydroxy23dihydro1himidazo12apyrimidin5one AT urbanczyklipkowskazofia 62chlorobenzyl14chlorophenyl7hydroxy23dihydro1himidazo12apyrimidin5one AT kalickiprzemysław 62chlorobenzyl14chlorophenyl7hydroxy23dihydro1himidazo12apyrimidin5one |