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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,...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2012
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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. |
format | Online Article Text |
id | pubmed-3588260 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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