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rac-N-Benzyl­isatincreatinine (unknown solvate)

The title compound, C(19)H(18)N(4)O(3) [systematic name: (RS)-1-benzyl-3-hy­droxy-3-(2-imino-3-methyl-5-oxoimidazolidin-4-yl)-2,3-dihydro-1H-indol-2-one], was prepared as a racemate (RR and SS) by the aldol condensation of N-benzyl­isatin with creatinine in the presence of sodium acetate in acetic a...

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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/PMC3569814/
https://www.ncbi.nlm.nih.gov/pubmed/23424560
http://dx.doi.org/10.1107/S1600536813000378
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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 The title compound, C(19)H(18)N(4)O(3) [systematic name: (RS)-1-benzyl-3-hy­droxy-3-(2-imino-3-methyl-5-oxoimidazolidin-4-yl)-2,3-dihydro-1H-indol-2-one], was prepared as a racemate (RR and SS) by the aldol condensation of N-benzyl­isatin with creatinine in the presence of sodium acetate in acetic acid. The r.m.s. deviation of the isatin ring system is 0.033 Å. The benzyl group is disordered over two orientations, with refined occupancies of 0.847 (7) and 0.153 (7). The dihedral angles between the isatin ring system and the benzene ring (major disorder component) and the imidazole ring are 82.82 (7) and 51.31 (3)°, respectively, In the crystal, mol­ecules are linked into (001) sheets by N—H⋯O and O—H⋯N hydrogen bonds, which incorporate R (2) (2)(9) ring motifs. The crystal was grown from mixed solvents (ethanol, methanol and possibly also ethyl acetate). These solvents are disordered in the crystal and the resulting electron density was found to be uninter­pretable. The solvent contribution to the scattering was removed with the SQUEEZE routine in PLATON [Spek (2009 ▶). Acta Cryst. D65, 148–155]. The formula mass and density do not take account of the solvent.
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spelling pubmed-35698142013-02-19 rac-N-Benzyl­isatincreatinine (unknown solvate) Penthala, Narsimha Reddy Crooks, Peter A. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(19)H(18)N(4)O(3) [systematic name: (RS)-1-benzyl-3-hy­droxy-3-(2-imino-3-methyl-5-oxoimidazolidin-4-yl)-2,3-dihydro-1H-indol-2-one], was prepared as a racemate (RR and SS) by the aldol condensation of N-benzyl­isatin with creatinine in the presence of sodium acetate in acetic acid. The r.m.s. deviation of the isatin ring system is 0.033 Å. The benzyl group is disordered over two orientations, with refined occupancies of 0.847 (7) and 0.153 (7). The dihedral angles between the isatin ring system and the benzene ring (major disorder component) and the imidazole ring are 82.82 (7) and 51.31 (3)°, respectively, In the crystal, mol­ecules are linked into (001) sheets by N—H⋯O and O—H⋯N hydrogen bonds, which incorporate R (2) (2)(9) ring motifs. The crystal was grown from mixed solvents (ethanol, methanol and possibly also ethyl acetate). These solvents are disordered in the crystal and the resulting electron density was found to be uninter­pretable. The solvent contribution to the scattering was removed with the SQUEEZE routine in PLATON [Spek (2009 ▶). Acta Cryst. D65, 148–155]. The formula mass and density do not take account of the solvent. International Union of Crystallography 2013-01-26 /pmc/articles/PMC3569814/ /pubmed/23424560 http://dx.doi.org/10.1107/S1600536813000378 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-N-Benzyl­isatincreatinine (unknown solvate)
title rac-N-Benzyl­isatincreatinine (unknown solvate)
title_full rac-N-Benzyl­isatincreatinine (unknown solvate)
title_fullStr rac-N-Benzyl­isatincreatinine (unknown solvate)
title_full_unstemmed rac-N-Benzyl­isatincreatinine (unknown solvate)
title_short rac-N-Benzyl­isatincreatinine (unknown solvate)
title_sort rac-n-benzyl­isatincreatinine (unknown solvate)
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3569814/
https://www.ncbi.nlm.nih.gov/pubmed/23424560
http://dx.doi.org/10.1107/S1600536813000378
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AT crookspetera racnbenzylisatincreatinineunknownsolvate