Cargando…

Propiverinium picrate

The title compound [systematic name: 4-(2,2-diphenyl-2-prop­oxyacet­oxy)-1-methyl­piperidin-1-ium picrate], C(23)H(30)NO(3) (+)·C(6)H(2)N(3)O(7) (−), crystallizes as a salt with one cation–anion (propiverinium picrate) pair in the asymmetric unit. A significant number of conformational changes are o...

Descripción completa

Detalles Bibliográficos
Autores principales: Jasinski, Jerry P., Butcher, Ray J., Hakim Al-Arique, Q. N. M., Yathirajan, H. S., Narayana, B.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977143/
https://www.ncbi.nlm.nih.gov/pubmed/21583452
http://dx.doi.org/10.1107/S1600536809022995
_version_ 1782191037194698752
author Jasinski, Jerry P.
Butcher, Ray J.
Hakim Al-Arique, Q. N. M.
Yathirajan, H. S.
Narayana, B.
author_facet Jasinski, Jerry P.
Butcher, Ray J.
Hakim Al-Arique, Q. N. M.
Yathirajan, H. S.
Narayana, B.
author_sort Jasinski, Jerry P.
collection PubMed
description The title compound [systematic name: 4-(2,2-diphenyl-2-prop­oxyacet­oxy)-1-methyl­piperidin-1-ium picrate], C(23)H(30)NO(3) (+)·C(6)H(2)N(3)O(7) (−), crystallizes as a salt with one cation–anion (propiverinium picrate) pair in the asymmetric unit. A significant number of conformational changes are observed between the crystalline environment of this cation–anion salt and that of a density functional theory (DFT) calculation of the geometry-optimized structure. The angle between the dihedral planes of the two benzyl rings in the propiverinium cation increases by 14.4 (0)° from that of the crystalline environment. The dihedral angles between the mean planes of each of the benzyl rings and the mean plane of the piperidine increase by 2.0 (8) and 12.3 (5)°. The angles between the mean plane of the acetate group and the mean planes of the inter­connected piperidine group and the two benzyl rings decrease by 0.2 (1), 7.4 (6) and 3.2 (2)°, respectively. The mean plane of the phenolate group in the anion changes by +22.6 (9), +22.1 (1) and −2.8 (6)° from the mean planes of the piperidine and benzyl rings in the cation, respectively. In the crystal, a bifurcated N—H⋯(O,O) hydrogen bond and a weak C—H⋯π ring inter­action help to establish the packing. The two O atoms of the p-NO(2) group are disordered with occupancies 0.825 (10):0.175 (10).
format Text
id pubmed-2977143
institution National Center for Biotechnology Information
language English
publishDate 2009
publisher International Union of Crystallography
record_format MEDLINE/PubMed
spelling pubmed-29771432010-12-30 Propiverinium picrate Jasinski, Jerry P. Butcher, Ray J. Hakim Al-Arique, Q. N. M. Yathirajan, H. S. Narayana, B. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound [systematic name: 4-(2,2-diphenyl-2-prop­oxyacet­oxy)-1-methyl­piperidin-1-ium picrate], C(23)H(30)NO(3) (+)·C(6)H(2)N(3)O(7) (−), crystallizes as a salt with one cation–anion (propiverinium picrate) pair in the asymmetric unit. A significant number of conformational changes are observed between the crystalline environment of this cation–anion salt and that of a density functional theory (DFT) calculation of the geometry-optimized structure. The angle between the dihedral planes of the two benzyl rings in the propiverinium cation increases by 14.4 (0)° from that of the crystalline environment. The dihedral angles between the mean planes of each of the benzyl rings and the mean plane of the piperidine increase by 2.0 (8) and 12.3 (5)°. The angles between the mean plane of the acetate group and the mean planes of the inter­connected piperidine group and the two benzyl rings decrease by 0.2 (1), 7.4 (6) and 3.2 (2)°, respectively. The mean plane of the phenolate group in the anion changes by +22.6 (9), +22.1 (1) and −2.8 (6)° from the mean planes of the piperidine and benzyl rings in the cation, respectively. In the crystal, a bifurcated N—H⋯(O,O) hydrogen bond and a weak C—H⋯π ring inter­action help to establish the packing. The two O atoms of the p-NO(2) group are disordered with occupancies 0.825 (10):0.175 (10). International Union of Crystallography 2009-07-01 /pmc/articles/PMC2977143/ /pubmed/21583452 http://dx.doi.org/10.1107/S1600536809022995 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.
Hakim Al-Arique, Q. N. M.
Yathirajan, H. S.
Narayana, B.
Propiverinium picrate
title Propiverinium picrate
title_full Propiverinium picrate
title_fullStr Propiverinium picrate
title_full_unstemmed Propiverinium picrate
title_short Propiverinium picrate
title_sort propiverinium picrate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977143/
https://www.ncbi.nlm.nih.gov/pubmed/21583452
http://dx.doi.org/10.1107/S1600536809022995
work_keys_str_mv AT jasinskijerryp propiveriniumpicrate
AT butcherrayj propiveriniumpicrate
AT hakimalariqueqnm propiveriniumpicrate
AT yathirajanhs propiveriniumpicrate
AT narayanab propiveriniumpicrate