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rac-5-Bromo-N-benzyl­isatincreatinine ethanol monosolvate

In the title compound [systematic name: rac-1-benzyl-5-bromo-3-hy­droxy-3-(2-imino-3-methyl-5-oxoimidazolidin-4-yl)-2,3-dihydro-1H-indol-2-one ethanol monosolvate], C(19)H(17)BrN(4)O(3)·C(2)H(5)OH, which crystallized as a racemate (RR and SS), the isatin ring is almost planar, with an r.m.s. deviati...

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Autores principales: Penthala, Narsimha Reddy, Crooks, Peter A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3569813/
https://www.ncbi.nlm.nih.gov/pubmed/23424559
http://dx.doi.org/10.1107/S160053681300038X
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author Penthala, Narsimha Reddy
Crooks, Peter A.
author_facet Penthala, Narsimha Reddy
Crooks, Peter A.
author_sort Penthala, Narsimha Reddy
collection PubMed
description In the title compound [systematic name: rac-1-benzyl-5-bromo-3-hy­droxy-3-(2-imino-3-methyl-5-oxoimidazolidin-4-yl)-2,3-dihydro-1H-indol-2-one ethanol monosolvate], C(19)H(17)BrN(4)O(3)·C(2)H(5)OH, which crystallized as a racemate (RR and SS), the isatin ring is almost planar, with an r.m.s. deviations from the mean plane of 0.0276 (14) Å. The phenyl ring of the benzyl group makes a dihedral angle with the mean plane of the isatin ring of 87.40 (5)° and the dihedral angle between the imidazole and isatin rings is 58.56 (7)°. In the crystal, mol­ecules are linked into two-dimensional pleated-sheet networks in the ac plane formed by O—H⋯O, N—H⋯O and O—H⋯N hydrogen bonds; within these sheets there are R (4) (4)(10) rings that involve three mol­ecules of the title compound and a single ethanol solvent mol­ecule. In addition, there are π–π inter­actions between inversion-related benzyl groups, with an inter­planar spacing of 3.444 (3) Å.
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spelling pubmed-35698132013-02-19 rac-5-Bromo-N-benzyl­isatincreatinine ethanol monosolvate Penthala, Narsimha Reddy Crooks, Peter A. Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound [systematic name: rac-1-benzyl-5-bromo-3-hy­droxy-3-(2-imino-3-methyl-5-oxoimidazolidin-4-yl)-2,3-dihydro-1H-indol-2-one ethanol monosolvate], C(19)H(17)BrN(4)O(3)·C(2)H(5)OH, which crystallized as a racemate (RR and SS), the isatin ring is almost planar, with an r.m.s. deviations from the mean plane of 0.0276 (14) Å. The phenyl ring of the benzyl group makes a dihedral angle with the mean plane of the isatin ring of 87.40 (5)° and the dihedral angle between the imidazole and isatin rings is 58.56 (7)°. In the crystal, mol­ecules are linked into two-dimensional pleated-sheet networks in the ac plane formed by O—H⋯O, N—H⋯O and O—H⋯N hydrogen bonds; within these sheets there are R (4) (4)(10) rings that involve three mol­ecules of the title compound and a single ethanol solvent mol­ecule. In addition, there are π–π inter­actions between inversion-related benzyl groups, with an inter­planar spacing of 3.444 (3) Å. International Union of Crystallography 2013-01-26 /pmc/articles/PMC3569813/ /pubmed/23424559 http://dx.doi.org/10.1107/S160053681300038X Text en © Penthala and Crooks 2013 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
Penthala, Narsimha Reddy
Crooks, Peter A.
rac-5-Bromo-N-benzyl­isatincreatinine ethanol monosolvate
title rac-5-Bromo-N-benzyl­isatincreatinine ethanol monosolvate
title_full rac-5-Bromo-N-benzyl­isatincreatinine ethanol monosolvate
title_fullStr rac-5-Bromo-N-benzyl­isatincreatinine ethanol monosolvate
title_full_unstemmed rac-5-Bromo-N-benzyl­isatincreatinine ethanol monosolvate
title_short rac-5-Bromo-N-benzyl­isatincreatinine ethanol monosolvate
title_sort rac-5-bromo-n-benzyl­isatincreatinine ethanol monosolvate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3569813/
https://www.ncbi.nlm.nih.gov/pubmed/23424559
http://dx.doi.org/10.1107/S160053681300038X
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