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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...

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Autores principales: Wysocki, Waldemar, Matosiuk, Dariusz, Rządkowska, Marzena, Karczmarzyk, Zbigniew, Urbańczyk-Lipkowska, Zofia, Kalicki, Przemysław
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
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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].
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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
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