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4-[(E)-(2,4-Difluoro­phen­yl)(hydroxy­imino)meth­yl]piperidinium picrate

The title compound, C(12)H(15)F(2)N(2)O(+)·C(6)H(2)N(3)O(7) (−), a picrate salt of 4-[(E)-(2,4-difluoro­phen­yl)(hydroxy­imino)meth­yl]piper­idine, crystallizes with two independent mol­ecules in a cation–anion pair in the asymmetric unit. In the cation, a methyl group is tris­ubstituted by hydroxy­...

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Autores principales: Jasinski, Jerry P., Butcher, Ray J., Yathirajan, H. S., Mallesha, L., Mohana, K. N.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2970333/
https://www.ncbi.nlm.nih.gov/pubmed/21577832
http://dx.doi.org/10.1107/S1600536809035363
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author Jasinski, Jerry P.
Butcher, Ray J.
Yathirajan, H. S.
Mallesha, L.
Mohana, K. N.
author_facet Jasinski, Jerry P.
Butcher, Ray J.
Yathirajan, H. S.
Mallesha, L.
Mohana, K. N.
author_sort Jasinski, Jerry P.
collection PubMed
description The title compound, C(12)H(15)F(2)N(2)O(+)·C(6)H(2)N(3)O(7) (−), a picrate salt of 4-[(E)-(2,4-difluoro­phen­yl)(hydroxy­imino)meth­yl]piper­idine, crystallizes with two independent mol­ecules in a cation–anion pair in the asymmetric unit. In the cation, a methyl group is tris­ubstituted by hydroxy­imino, piperidin-4-yl and 2,4-difluoro­phenyl groups, the latter of which contains an F atom disordered over two positions in the ring [occupancy ratio 0.631 (4):0.369 (4)]. The mean plane of the hydr­oxy group is in a synclinical conformation nearly orthogonal [N—C—C—C = 72.44 (19)°] to the mean plane of the piperidine ring, which adopts a slightly distorted chair conformation. The dihedral angle between the mean plane of the 2,4-difluoro­phenyl and piperidin-4-yl groups is 60.2 (3)°. In the picrate anion, the mean planes of the two o-NO(2) and single p-NO(2) groups adopt twist angles of 5.7 (2), 25.3 (7) and 8.3 (6)°, respectively, with the attached planar benzene ring. The dihedral angle between the mean planes of the benzene ring in the picrate anion and those in the hydroxy­imino, piperidin-4-yl and 2,4-difluoro­phenyl groups in the cation are 84.9 (7), 78.9 (4) and 65.1 (1)°, respectively. Extensive hydrogen-bond inter­actions occur between the cation–anion pair, which help to establish the crystal packing in the unit cell. This includes dual three-center hydrogen bonds with the piperidin-4-yl group, the phenolate and o-NO(2) O atoms of the picrate anion at different positions in the unit cell, which form separate N—H⋯(O,O) bifurcated inter­molecular hydrogen-bond inter­actions. Also, the hydr­oxy group forms a separate hydrogen bond with a nearby piperidin-4-yl N atom, thus providing two groups of hydrogen bonds, which form an infinite two-dimensional network along (011).
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spelling pubmed-29703332010-12-30 4-[(E)-(2,4-Difluoro­phen­yl)(hydroxy­imino)meth­yl]piperidinium picrate Jasinski, Jerry P. Butcher, Ray J. Yathirajan, H. S. Mallesha, L. Mohana, K. N. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(12)H(15)F(2)N(2)O(+)·C(6)H(2)N(3)O(7) (−), a picrate salt of 4-[(E)-(2,4-difluoro­phen­yl)(hydroxy­imino)meth­yl]piper­idine, crystallizes with two independent mol­ecules in a cation–anion pair in the asymmetric unit. In the cation, a methyl group is tris­ubstituted by hydroxy­imino, piperidin-4-yl and 2,4-difluoro­phenyl groups, the latter of which contains an F atom disordered over two positions in the ring [occupancy ratio 0.631 (4):0.369 (4)]. The mean plane of the hydr­oxy group is in a synclinical conformation nearly orthogonal [N—C—C—C = 72.44 (19)°] to the mean plane of the piperidine ring, which adopts a slightly distorted chair conformation. The dihedral angle between the mean plane of the 2,4-difluoro­phenyl and piperidin-4-yl groups is 60.2 (3)°. In the picrate anion, the mean planes of the two o-NO(2) and single p-NO(2) groups adopt twist angles of 5.7 (2), 25.3 (7) and 8.3 (6)°, respectively, with the attached planar benzene ring. The dihedral angle between the mean planes of the benzene ring in the picrate anion and those in the hydroxy­imino, piperidin-4-yl and 2,4-difluoro­phenyl groups in the cation are 84.9 (7), 78.9 (4) and 65.1 (1)°, respectively. Extensive hydrogen-bond inter­actions occur between the cation–anion pair, which help to establish the crystal packing in the unit cell. This includes dual three-center hydrogen bonds with the piperidin-4-yl group, the phenolate and o-NO(2) O atoms of the picrate anion at different positions in the unit cell, which form separate N—H⋯(O,O) bifurcated inter­molecular hydrogen-bond inter­actions. Also, the hydr­oxy group forms a separate hydrogen bond with a nearby piperidin-4-yl N atom, thus providing two groups of hydrogen bonds, which form an infinite two-dimensional network along (011). International Union of Crystallography 2009-09-05 /pmc/articles/PMC2970333/ /pubmed/21577832 http://dx.doi.org/10.1107/S1600536809035363 Text en © Jasinski et al. 2009 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.
Yathirajan, H. S.
Mallesha, L.
Mohana, K. N.
4-[(E)-(2,4-Difluoro­phen­yl)(hydroxy­imino)meth­yl]piperidinium picrate
title 4-[(E)-(2,4-Difluoro­phen­yl)(hydroxy­imino)meth­yl]piperidinium picrate
title_full 4-[(E)-(2,4-Difluoro­phen­yl)(hydroxy­imino)meth­yl]piperidinium picrate
title_fullStr 4-[(E)-(2,4-Difluoro­phen­yl)(hydroxy­imino)meth­yl]piperidinium picrate
title_full_unstemmed 4-[(E)-(2,4-Difluoro­phen­yl)(hydroxy­imino)meth­yl]piperidinium picrate
title_short 4-[(E)-(2,4-Difluoro­phen­yl)(hydroxy­imino)meth­yl]piperidinium picrate
title_sort 4-[(e)-(2,4-difluoro­phen­yl)(hydroxy­imino)meth­yl]piperidinium picrate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2970333/
https://www.ncbi.nlm.nih.gov/pubmed/21577832
http://dx.doi.org/10.1107/S1600536809035363
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