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(R,R)-1-Acetyl-1′-(2,4,6-trinitro­phen­yl)-2,2′-bipyrrolidine

The structure of the title mol­ecule, C(16)H(19)N(5)O(7), is mainly determined by the steric effect of a bulky 2,4,6-trinitro­phenyl group attached to the N atom of a pyrrolidine ring. Both pyrrolidine rings adopt an envelope conformation, with one of the methylene C atoms as the flap in each case,...

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Autores principales: Eichstaedt, Katarzyna, Olszewska, Teresa, Gdaniec, Maria
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588260/
https://www.ncbi.nlm.nih.gov/pubmed/23476399
http://dx.doi.org/10.1107/S1600536812051161
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author Eichstaedt, Katarzyna
Olszewska, Teresa
Gdaniec, Maria
author_facet Eichstaedt, Katarzyna
Olszewska, Teresa
Gdaniec, Maria
author_sort Eichstaedt, Katarzyna
collection PubMed
description The structure of the title mol­ecule, C(16)H(19)N(5)O(7), is mainly determined by the steric effect of a bulky 2,4,6-trinitro­phenyl group attached to the N atom of a pyrrolidine ring. Both pyrrolidine rings adopt an envelope conformation, with one of the methylene C atoms as the flap in each case, and the N—C—C—N torsion angle along the bond connecting the two pyrrolidine rings is −174.9 (2)°. The benzene ring of the 2,3,5-trinitro­phenyl substituent is deformed and the r.m.s. deviation of its six atoms from the best plane is 0.026 Å. The N atoms of the two nitro groups in the ortho positions deviate from the best plane of the benzene ring by −0.033 (5) and 0.385 (5) Å. These groups, as well as the pyrrolidine ring, are twisted relative to the aromatic ring in the same direction, their best planes forming dihedral angles of 30.2 (2), 64.8 (1) and 46.6 (2)°, respectively, with the ring. An intra­molecular C—H⋯O hydrogen bond occurs. In the crystal, there is a short [O⋯C = 3.019 (4) Å] contact between a nitro O atom and a C atom of the benzene ring bearing the nitro group and a C—H⋯O inter­action between a methyl H atom and another nitro O atom.
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spelling pubmed-35882602013-03-08 (R,R)-1-Acetyl-1′-(2,4,6-trinitro­phen­yl)-2,2′-bipyrrolidine Eichstaedt, Katarzyna Olszewska, Teresa Gdaniec, Maria Acta Crystallogr Sect E Struct Rep Online Organic Papers The structure of the title mol­ecule, C(16)H(19)N(5)O(7), is mainly determined by the steric effect of a bulky 2,4,6-trinitro­phenyl group attached to the N atom of a pyrrolidine ring. Both pyrrolidine rings adopt an envelope conformation, with one of the methylene C atoms as the flap in each case, and the N—C—C—N torsion angle along the bond connecting the two pyrrolidine rings is −174.9 (2)°. The benzene ring of the 2,3,5-trinitro­phenyl substituent is deformed and the r.m.s. deviation of its six atoms from the best plane is 0.026 Å. The N atoms of the two nitro groups in the ortho positions deviate from the best plane of the benzene ring by −0.033 (5) and 0.385 (5) Å. These groups, as well as the pyrrolidine ring, are twisted relative to the aromatic ring in the same direction, their best planes forming dihedral angles of 30.2 (2), 64.8 (1) and 46.6 (2)°, respectively, with the ring. An intra­molecular C—H⋯O hydrogen bond occurs. In the crystal, there is a short [O⋯C = 3.019 (4) Å] contact between a nitro O atom and a C atom of the benzene ring bearing the nitro group and a C—H⋯O inter­action between a methyl H atom and another nitro O atom. International Union of Crystallography 2012-12-22 /pmc/articles/PMC3588260/ /pubmed/23476399 http://dx.doi.org/10.1107/S1600536812051161 Text en © Eichstaedt et al. 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
Eichstaedt, Katarzyna
Olszewska, Teresa
Gdaniec, Maria
(R,R)-1-Acetyl-1′-(2,4,6-trinitro­phen­yl)-2,2′-bipyrrolidine
title (R,R)-1-Acetyl-1′-(2,4,6-trinitro­phen­yl)-2,2′-bipyrrolidine
title_full (R,R)-1-Acetyl-1′-(2,4,6-trinitro­phen­yl)-2,2′-bipyrrolidine
title_fullStr (R,R)-1-Acetyl-1′-(2,4,6-trinitro­phen­yl)-2,2′-bipyrrolidine
title_full_unstemmed (R,R)-1-Acetyl-1′-(2,4,6-trinitro­phen­yl)-2,2′-bipyrrolidine
title_short (R,R)-1-Acetyl-1′-(2,4,6-trinitro­phen­yl)-2,2′-bipyrrolidine
title_sort (r,r)-1-acetyl-1′-(2,4,6-trinitro­phen­yl)-2,2′-bipyrrolidine
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3588260/
https://www.ncbi.nlm.nih.gov/pubmed/23476399
http://dx.doi.org/10.1107/S1600536812051161
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