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(Z)-tert-Butyl 2-(4-amino-9H-fluoren-9-yl­idene)acetate

The title compound, C(19)H(19)NO(2), obtained as an almost equimolar mixture (as shown by (1)H NMR) with the E isomer through a Wittig reaction between 4-amino-9H-fluoren-9-one and the stabilized ylide Ph(3)P=CHCO(2)C(CH(3))(3), was obtained pure in the Z configuration following crystallization from...

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Detalles Bibliográficos
Autores principales: Krokidis, Marios, Papaioannou, Dionissios, Nastopoulos, Vassilios
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2008
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2959429/
https://www.ncbi.nlm.nih.gov/pubmed/21201178
http://dx.doi.org/10.1107/S1600536808029735
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author Krokidis, Marios
Papaioannou, Dionissios
Nastopoulos, Vassilios
author_facet Krokidis, Marios
Papaioannou, Dionissios
Nastopoulos, Vassilios
author_sort Krokidis, Marios
collection PubMed
description The title compound, C(19)H(19)NO(2), obtained as an almost equimolar mixture (as shown by (1)H NMR) with the E isomer through a Wittig reaction between 4-amino-9H-fluoren-9-one and the stabilized ylide Ph(3)P=CHCO(2)C(CH(3))(3), was obtained pure in the Z configuration following crystallization from toluene. The mol­ecule shows a planar arrangement of the ring system and the new double bond, whereas the carbonyl O atom forms a 45.1 (3)° dihedral angle with it. The mol­ecules are linked by N—H⋯O hydrogen bonds, forming cyclic structures with R (4) (4)(24) graph-set motifs. These motifs are connected to each other, giving rise to a sheet structure parallel to the ab plane. The linkage within the sheets is further enhanced by π–π stacking inter­actions between the fluorene units [centroid–centroid distance = 3.583 (2) Å].
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spelling pubmed-29594292010-12-30 (Z)-tert-Butyl 2-(4-amino-9H-fluoren-9-yl­idene)acetate Krokidis, Marios Papaioannou, Dionissios Nastopoulos, Vassilios Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(19)H(19)NO(2), obtained as an almost equimolar mixture (as shown by (1)H NMR) with the E isomer through a Wittig reaction between 4-amino-9H-fluoren-9-one and the stabilized ylide Ph(3)P=CHCO(2)C(CH(3))(3), was obtained pure in the Z configuration following crystallization from toluene. The mol­ecule shows a planar arrangement of the ring system and the new double bond, whereas the carbonyl O atom forms a 45.1 (3)° dihedral angle with it. The mol­ecules are linked by N—H⋯O hydrogen bonds, forming cyclic structures with R (4) (4)(24) graph-set motifs. These motifs are connected to each other, giving rise to a sheet structure parallel to the ab plane. The linkage within the sheets is further enhanced by π–π stacking inter­actions between the fluorene units [centroid–centroid distance = 3.583 (2) Å]. International Union of Crystallography 2008-09-20 /pmc/articles/PMC2959429/ /pubmed/21201178 http://dx.doi.org/10.1107/S1600536808029735 Text en © Krokidis et al. 2008 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
Krokidis, Marios
Papaioannou, Dionissios
Nastopoulos, Vassilios
(Z)-tert-Butyl 2-(4-amino-9H-fluoren-9-yl­idene)acetate
title (Z)-tert-Butyl 2-(4-amino-9H-fluoren-9-yl­idene)acetate
title_full (Z)-tert-Butyl 2-(4-amino-9H-fluoren-9-yl­idene)acetate
title_fullStr (Z)-tert-Butyl 2-(4-amino-9H-fluoren-9-yl­idene)acetate
title_full_unstemmed (Z)-tert-Butyl 2-(4-amino-9H-fluoren-9-yl­idene)acetate
title_short (Z)-tert-Butyl 2-(4-amino-9H-fluoren-9-yl­idene)acetate
title_sort (z)-tert-butyl 2-(4-amino-9h-fluoren-9-yl­idene)acetate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2959429/
https://www.ncbi.nlm.nih.gov/pubmed/21201178
http://dx.doi.org/10.1107/S1600536808029735
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