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Enrofloxacinium picrate

There is one cation–anion pair in the asymmetric unit of the title compound [systematic name: 4-(3-carb­oxy-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)-1-ethyl­piperazin-1-ium 2,4,6-tri­nitro­phenolate], C(19)H(23)FN(3)O(3) (+)·C(6)H(2)N(3)O(7) (−). The six-membered piperazine group in the cation adopt...

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Autores principales: Jasinski, Jerry P., Butcher, Ray J., Siddegowda, M. S., Yathirajan, H. S., Siddaraju, B. P.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3051675/
https://www.ncbi.nlm.nih.gov/pubmed/21523099
http://dx.doi.org/10.1107/S160053681100170X
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author Jasinski, Jerry P.
Butcher, Ray J.
Siddegowda, M. S.
Yathirajan, H. S.
Siddaraju, B. P.
author_facet Jasinski, Jerry P.
Butcher, Ray J.
Siddegowda, M. S.
Yathirajan, H. S.
Siddaraju, B. P.
author_sort Jasinski, Jerry P.
collection PubMed
description There is one cation–anion pair in the asymmetric unit of the title compound [systematic name: 4-(3-carb­oxy-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)-1-ethyl­piperazin-1-ium 2,4,6-tri­nitro­phenolate], C(19)H(23)FN(3)O(3) (+)·C(6)H(2)N(3)O(7) (−). The six-membered piperazine group in the cation adopts a slightly distorted chair conformation and contains a protonated N atom. The dihedral angles between the mean planes of the cyclo­propyl and piperazine rings in the cation with the 10-atom ring system of the quinolone group are 48.1 (1) and 69.9 (5)°, respectively. The picrate anion inter­acts with the protonated N atom of an adjacent cation through a bifurcated N—H⋯O three-center hydrogen bond, forming an R (1) (2)(6) ring motif. Furthermore, there is an intra­molecular O—H⋯O hydrogen bond. The dihedral angle between the mean planes of the anion benzene and cation piperizine, quinoline and cyclo­propyl rings are 61.3 (6), 31.1 (4) and 70.4 (9)°, respectively. The mean planes of the two o-NO(2) and single p-NO(2) groups in the picrate anion are twisted by 6.7 (6), 38.3 (9) and 12.8 (7)° with respect to the mean plane of the benzene ring. Strong N—H⋯O and weak inter­molecular C—H⋯O hydrogen bonds in concert with weak π–π stacking inter­actions [centroid–centroid distances = 3.5785 (13), 3.7451 (12) and 3.6587 (13) Å] dominate the crystal packing.
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spelling pubmed-30516752011-04-26 Enrofloxacinium picrate Jasinski, Jerry P. Butcher, Ray J. Siddegowda, M. S. Yathirajan, H. S. Siddaraju, B. P. Acta Crystallogr Sect E Struct Rep Online Organic Papers There is one cation–anion pair in the asymmetric unit of the title compound [systematic name: 4-(3-carb­oxy-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)-1-ethyl­piperazin-1-ium 2,4,6-tri­nitro­phenolate], C(19)H(23)FN(3)O(3) (+)·C(6)H(2)N(3)O(7) (−). The six-membered piperazine group in the cation adopts a slightly distorted chair conformation and contains a protonated N atom. The dihedral angles between the mean planes of the cyclo­propyl and piperazine rings in the cation with the 10-atom ring system of the quinolone group are 48.1 (1) and 69.9 (5)°, respectively. The picrate anion inter­acts with the protonated N atom of an adjacent cation through a bifurcated N—H⋯O three-center hydrogen bond, forming an R (1) (2)(6) ring motif. Furthermore, there is an intra­molecular O—H⋯O hydrogen bond. The dihedral angle between the mean planes of the anion benzene and cation piperizine, quinoline and cyclo­propyl rings are 61.3 (6), 31.1 (4) and 70.4 (9)°, respectively. The mean planes of the two o-NO(2) and single p-NO(2) groups in the picrate anion are twisted by 6.7 (6), 38.3 (9) and 12.8 (7)° with respect to the mean plane of the benzene ring. Strong N—H⋯O and weak inter­molecular C—H⋯O hydrogen bonds in concert with weak π–π stacking inter­actions [centroid–centroid distances = 3.5785 (13), 3.7451 (12) and 3.6587 (13) Å] dominate the crystal packing. International Union of Crystallography 2011-01-22 /pmc/articles/PMC3051675/ /pubmed/21523099 http://dx.doi.org/10.1107/S160053681100170X Text en © Jasinski et al. 2011 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
Jasinski, Jerry P.
Butcher, Ray J.
Siddegowda, M. S.
Yathirajan, H. S.
Siddaraju, B. P.
Enrofloxacinium picrate
title Enrofloxacinium picrate
title_full Enrofloxacinium picrate
title_fullStr Enrofloxacinium picrate
title_full_unstemmed Enrofloxacinium picrate
title_short Enrofloxacinium picrate
title_sort enrofloxacinium picrate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3051675/
https://www.ncbi.nlm.nih.gov/pubmed/21523099
http://dx.doi.org/10.1107/S160053681100170X
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