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3-Hydr­oxy-1,2,3,9-tetra­hydro­pyrrolo[2,1-b]quinazolin-4-ium chloride dihydrate: (+)-vasicinol hydro­chloride dihydrate from Peganum harmala L

The title compound, C(11)H(13)N(2)O(+)·Cl(−)·2H(2)O, the dihydrate of (+)-vasicinol hydro­chloride, is a pyrrolidinoquinazoline alkaloid. It was isolated from the ethyl acetate fraction of the leaves of Peganum harmala L. The pyrrolidine ring has an envelope conformation with the C atom at position...

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Autores principales: Khan, Amir Muhammad, Abbas, Ghulam, Qureshi, Rizwana Aleem, Khan, Uzma, Ghufran, Muhammad Asad, Stoeckli-Evans, Helen
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2968537/
https://www.ncbi.nlm.nih.gov/pubmed/21582144
http://dx.doi.org/10.1107/S1600536809003766
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author Khan, Amir Muhammad
Abbas, Ghulam
Qureshi, Rizwana Aleem
Khan, Uzma
Ghufran, Muhammad Asad
Stoeckli-Evans, Helen
author_facet Khan, Amir Muhammad
Abbas, Ghulam
Qureshi, Rizwana Aleem
Khan, Uzma
Ghufran, Muhammad Asad
Stoeckli-Evans, Helen
author_sort Khan, Amir Muhammad
collection PubMed
description The title compound, C(11)H(13)N(2)O(+)·Cl(−)·2H(2)O, the dihydrate of (+)-vasicinol hydro­chloride, is a pyrrolidinoquinazoline alkaloid. It was isolated from the ethyl acetate fraction of the leaves of Peganum harmala L. The pyrrolidine ring has an envelope conformation with the C atom at position 2 acting as the flap and the C atom at position 3, carrying the hydroxyl substituent, has an S configuration. The absolute configuration was determined as a result of the anomalous scattering of the Cl atom. In the crystal structure, mol­ecules stack along the a axis, connected to one another via inter­molecular O—H⋯Cl and N—H⋯Cl hydrogen bonds, forming approximately triangular-shaped R (2) (1)(7) rings, and O—H⋯Cl and O—H⋯O hydrogen bonds, forming penta­gonal-shaped R (5) (4)(10) rings. The overall effect is a ribbon-like arrangement running parallel to the a axis.
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spelling pubmed-29685372010-12-30 3-Hydr­oxy-1,2,3,9-tetra­hydro­pyrrolo[2,1-b]quinazolin-4-ium chloride dihydrate: (+)-vasicinol hydro­chloride dihydrate from Peganum harmala L Khan, Amir Muhammad Abbas, Ghulam Qureshi, Rizwana Aleem Khan, Uzma Ghufran, Muhammad Asad Stoeckli-Evans, Helen Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(11)H(13)N(2)O(+)·Cl(−)·2H(2)O, the dihydrate of (+)-vasicinol hydro­chloride, is a pyrrolidinoquinazoline alkaloid. It was isolated from the ethyl acetate fraction of the leaves of Peganum harmala L. The pyrrolidine ring has an envelope conformation with the C atom at position 2 acting as the flap and the C atom at position 3, carrying the hydroxyl substituent, has an S configuration. The absolute configuration was determined as a result of the anomalous scattering of the Cl atom. In the crystal structure, mol­ecules stack along the a axis, connected to one another via inter­molecular O—H⋯Cl and N—H⋯Cl hydrogen bonds, forming approximately triangular-shaped R (2) (1)(7) rings, and O—H⋯Cl and O—H⋯O hydrogen bonds, forming penta­gonal-shaped R (5) (4)(10) rings. The overall effect is a ribbon-like arrangement running parallel to the a axis. International Union of Crystallography 2009-02-06 /pmc/articles/PMC2968537/ /pubmed/21582144 http://dx.doi.org/10.1107/S1600536809003766 Text en © Khan 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
Khan, Amir Muhammad
Abbas, Ghulam
Qureshi, Rizwana Aleem
Khan, Uzma
Ghufran, Muhammad Asad
Stoeckli-Evans, Helen
3-Hydr­oxy-1,2,3,9-tetra­hydro­pyrrolo[2,1-b]quinazolin-4-ium chloride dihydrate: (+)-vasicinol hydro­chloride dihydrate from Peganum harmala L
title 3-Hydr­oxy-1,2,3,9-tetra­hydro­pyrrolo[2,1-b]quinazolin-4-ium chloride dihydrate: (+)-vasicinol hydro­chloride dihydrate from Peganum harmala L
title_full 3-Hydr­oxy-1,2,3,9-tetra­hydro­pyrrolo[2,1-b]quinazolin-4-ium chloride dihydrate: (+)-vasicinol hydro­chloride dihydrate from Peganum harmala L
title_fullStr 3-Hydr­oxy-1,2,3,9-tetra­hydro­pyrrolo[2,1-b]quinazolin-4-ium chloride dihydrate: (+)-vasicinol hydro­chloride dihydrate from Peganum harmala L
title_full_unstemmed 3-Hydr­oxy-1,2,3,9-tetra­hydro­pyrrolo[2,1-b]quinazolin-4-ium chloride dihydrate: (+)-vasicinol hydro­chloride dihydrate from Peganum harmala L
title_short 3-Hydr­oxy-1,2,3,9-tetra­hydro­pyrrolo[2,1-b]quinazolin-4-ium chloride dihydrate: (+)-vasicinol hydro­chloride dihydrate from Peganum harmala L
title_sort 3-hydr­oxy-1,2,3,9-tetra­hydro­pyrrolo[2,1-b]quinazolin-4-ium chloride dihydrate: (+)-vasicinol hydro­chloride dihydrate from peganum harmala l
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2968537/
https://www.ncbi.nlm.nih.gov/pubmed/21582144
http://dx.doi.org/10.1107/S1600536809003766
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