Brucinium 2-carboxy-6-nitrophthalate dihydrate

The 1:1 proton-transfer compound of brucine with 3-nitrophthalic acid

Graham Smith, Urs D. Wermuth, David J. Young, Peter C. Healy

Research output: Contribution to journalArticleResearchpeer-review

Abstract

In the title compound (systematic name: 2,3-dimethoxy-10-oxostrychnidinium 2-carboxy-6-nitrophthalate dihydrate), C23H27N 2O4 +·C8H4NO 6-·2H2O, the carboxylic acid and carboxylate groups of the hydrogenphthalate anions form head-to-tail catemeric chains of strong intermolecular O-H⋯O hydrogen bonds [O⋯O distance = 2.563 (5) Å] along the 21 screw axes parallel to the a axis. The chains further associate with the water molecules, forming sheet structures parallel to (010). The protonated N atom at the 19-position of the brucine molecule forms a peripheral intermolecular hydrogen bond with the carboxylate group of the anion.

Original languageEnglish
Pages (from-to)o2008-o2011
Number of pages4
JournalActa Crystallographica Section E: Structure Reports Online
VolumeE61
Issue numberPart 7
DOIs
Publication statusPublished - 1 Jul 2005
Externally publishedYes

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Proton transfer
carboxylates
Anions
Hydrogen bonds
Negative ions
hydrogen bonds
anions
acids
Molecules
Acids
protons
screws
Carboxylic Acids
Carboxylic acids
carboxylic acids
molecules
Atoms
Water
water
atoms

Cite this

@article{c13d84c3fac1498dbcc85d685e4eccf0,
title = "Brucinium 2-carboxy-6-nitrophthalate dihydrate: The 1:1 proton-transfer compound of brucine with 3-nitrophthalic acid",
abstract = "In the title compound (systematic name: 2,3-dimethoxy-10-oxostrychnidinium 2-carboxy-6-nitrophthalate dihydrate), C23H27N 2O4 +·C8H4NO 6-·2H2O, the carboxylic acid and carboxylate groups of the hydrogenphthalate anions form head-to-tail catemeric chains of strong intermolecular O-H⋯O hydrogen bonds [O⋯O distance = 2.563 (5) {\AA}] along the 21 screw axes parallel to the a axis. The chains further associate with the water molecules, forming sheet structures parallel to (010). The protonated N atom at the 19-position of the brucine molecule forms a peripheral intermolecular hydrogen bond with the carboxylate group of the anion.",
author = "Graham Smith and Wermuth, {Urs D.} and Young, {David J.} and Healy, {Peter C.}",
year = "2005",
month = "7",
day = "1",
doi = "10.1107/S1600536805017149",
language = "English",
volume = "E61",
pages = "o2008--o2011",
journal = "Acta Crystallographica Section E: Crystallographic Communications",
issn = "1600-5368",
publisher = "International Union of Crystallography",
number = "Part 7",

}

Brucinium 2-carboxy-6-nitrophthalate dihydrate : The 1:1 proton-transfer compound of brucine with 3-nitrophthalic acid. / Smith, Graham; Wermuth, Urs D.; Young, David J.; Healy, Peter C.

In: Acta Crystallographica Section E: Structure Reports Online, Vol. E61, No. Part 7, 01.07.2005, p. o2008-o2011.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Brucinium 2-carboxy-6-nitrophthalate dihydrate

T2 - The 1:1 proton-transfer compound of brucine with 3-nitrophthalic acid

AU - Smith, Graham

AU - Wermuth, Urs D.

AU - Young, David J.

AU - Healy, Peter C.

PY - 2005/7/1

Y1 - 2005/7/1

N2 - In the title compound (systematic name: 2,3-dimethoxy-10-oxostrychnidinium 2-carboxy-6-nitrophthalate dihydrate), C23H27N 2O4 +·C8H4NO 6-·2H2O, the carboxylic acid and carboxylate groups of the hydrogenphthalate anions form head-to-tail catemeric chains of strong intermolecular O-H⋯O hydrogen bonds [O⋯O distance = 2.563 (5) Å] along the 21 screw axes parallel to the a axis. The chains further associate with the water molecules, forming sheet structures parallel to (010). The protonated N atom at the 19-position of the brucine molecule forms a peripheral intermolecular hydrogen bond with the carboxylate group of the anion.

AB - In the title compound (systematic name: 2,3-dimethoxy-10-oxostrychnidinium 2-carboxy-6-nitrophthalate dihydrate), C23H27N 2O4 +·C8H4NO 6-·2H2O, the carboxylic acid and carboxylate groups of the hydrogenphthalate anions form head-to-tail catemeric chains of strong intermolecular O-H⋯O hydrogen bonds [O⋯O distance = 2.563 (5) Å] along the 21 screw axes parallel to the a axis. The chains further associate with the water molecules, forming sheet structures parallel to (010). The protonated N atom at the 19-position of the brucine molecule forms a peripheral intermolecular hydrogen bond with the carboxylate group of the anion.

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U2 - 10.1107/S1600536805017149

DO - 10.1107/S1600536805017149

M3 - Article

VL - E61

SP - o2008-o2011

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JF - Acta Crystallographica Section E: Crystallographic Communications

SN - 1600-5368

IS - Part 7

ER -