Crystal structures of an imidazo[1,5-a]pyridinium-based ligand and its (C13H12N3)(2)[CdI4] hybrid salt

Olga Yu Vassilyeva, Elena A. Buvaylo, Vladimir N. Kokozay, Brian W. Skelton, Alexandre N. Sobolev

Research output: Contribution to journalArticle

Abstract

The monocation product of the oxidative condensation-cyclization between two molecules of pyridine-2-carbaldehyde and one molecule of CH3NH2 center dot HCl in methanol, 2-methyl-3-(pyridin-2-yl)imidazo[1,5-a]pyridinium, was isolated in the presence of metal ions as bis[2-methyl-3-(pyridin-2-yl)imidazo[1,5-a]pyridin-2-ium] tetraiodocadmate, (C13H12N3)(2)[CdI4], (I), and the mixed chloride/nitrate salt, bis[2-methyl-3-(pyridin-2-yl)imidazo[1,5-a]pyridin-2-ium] 1.5-chloride 0.5-nitrate trihydrate, 2C(13)H(12)N(3)(+)center dot 1.5Cl(-)center dot 0.5NO(3)(-)center dot 3H(2)O, (II). Hybrid salt (I) crystallizes in the space group P2(1)/n with two [L](2)[CdI4] molecules in the asymmetric unit related by pseudosymmetry. In the crystal of (I), layers of organic cations and of tetrahalometallate anions are stacked parallel to the ab plane. Antiparallel L+ cations disposed in a herring-bone pattern form pi-bonded chains through aromatic stacking. In the inorganic layer, adjacent tetrahedral CdI4 units have no connectivity but demonstrate close packing of iodide anions. In the crystal lattice of (II), the cations are arranged in stacks propagating along the a axis; the one-dimensional hydrogen-bonded polymer built of chloride ions and water molecules runs parallel to a column of stacked cations.

Original languageEnglish
Pages (from-to)1209-+
Number of pages23
JournalActa Crystallographica. Section E: Structure Reports Online
Volume75
DOIs
Publication statusPublished - Aug 2019

Cite this

@article{876b2a8500a8435c8e69f5b289019a2b,
title = "Crystal structures of an imidazo[1,5-a]pyridinium-based ligand and its (C13H12N3)(2)[CdI4] hybrid salt",
abstract = "The monocation product of the oxidative condensation-cyclization between two molecules of pyridine-2-carbaldehyde and one molecule of CH3NH2 center dot HCl in methanol, 2-methyl-3-(pyridin-2-yl)imidazo[1,5-a]pyridinium, was isolated in the presence of metal ions as bis[2-methyl-3-(pyridin-2-yl)imidazo[1,5-a]pyridin-2-ium] tetraiodocadmate, (C13H12N3)(2)[CdI4], (I), and the mixed chloride/nitrate salt, bis[2-methyl-3-(pyridin-2-yl)imidazo[1,5-a]pyridin-2-ium] 1.5-chloride 0.5-nitrate trihydrate, 2C(13)H(12)N(3)(+)center dot 1.5Cl(-)center dot 0.5NO(3)(-)center dot 3H(2)O, (II). Hybrid salt (I) crystallizes in the space group P2(1)/n with two [L](2)[CdI4] molecules in the asymmetric unit related by pseudosymmetry. In the crystal of (I), layers of organic cations and of tetrahalometallate anions are stacked parallel to the ab plane. Antiparallel L+ cations disposed in a herring-bone pattern form pi-bonded chains through aromatic stacking. In the inorganic layer, adjacent tetrahedral CdI4 units have no connectivity but demonstrate close packing of iodide anions. In the crystal lattice of (II), the cations are arranged in stacks propagating along the a axis; the one-dimensional hydrogen-bonded polymer built of chloride ions and water molecules runs parallel to a column of stacked cations.",
keywords = "organic-inorganic hybrid, tetrahalometallate, crystal structure, hydrogen-bonding interactions, pi-pi stacking, CYCLIZATION, EMISSION, CATION",
author = "Vassilyeva, {Olga Yu} and Buvaylo, {Elena A.} and Kokozay, {Vladimir N.} and Skelton, {Brian W.} and Sobolev, {Alexandre N.}",
year = "2019",
month = "8",
doi = "10.1107/S2056989019009964",
language = "English",
volume = "75",
pages = "1209--+",
journal = "Acta Crystallographica. Section E: Structure Reports Online",
issn = "1600-5368",
publisher = "INT UNION CRYSTALLOGRAPHY",

}

Crystal structures of an imidazo[1,5-a]pyridinium-based ligand and its (C13H12N3)(2)[CdI4] hybrid salt. / Vassilyeva, Olga Yu; Buvaylo, Elena A.; Kokozay, Vladimir N.; Skelton, Brian W.; Sobolev, Alexandre N.

In: Acta Crystallographica. Section E: Structure Reports Online, Vol. 75, 08.2019, p. 1209-+.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Crystal structures of an imidazo[1,5-a]pyridinium-based ligand and its (C13H12N3)(2)[CdI4] hybrid salt

AU - Vassilyeva, Olga Yu

AU - Buvaylo, Elena A.

AU - Kokozay, Vladimir N.

AU - Skelton, Brian W.

AU - Sobolev, Alexandre N.

PY - 2019/8

Y1 - 2019/8

N2 - The monocation product of the oxidative condensation-cyclization between two molecules of pyridine-2-carbaldehyde and one molecule of CH3NH2 center dot HCl in methanol, 2-methyl-3-(pyridin-2-yl)imidazo[1,5-a]pyridinium, was isolated in the presence of metal ions as bis[2-methyl-3-(pyridin-2-yl)imidazo[1,5-a]pyridin-2-ium] tetraiodocadmate, (C13H12N3)(2)[CdI4], (I), and the mixed chloride/nitrate salt, bis[2-methyl-3-(pyridin-2-yl)imidazo[1,5-a]pyridin-2-ium] 1.5-chloride 0.5-nitrate trihydrate, 2C(13)H(12)N(3)(+)center dot 1.5Cl(-)center dot 0.5NO(3)(-)center dot 3H(2)O, (II). Hybrid salt (I) crystallizes in the space group P2(1)/n with two [L](2)[CdI4] molecules in the asymmetric unit related by pseudosymmetry. In the crystal of (I), layers of organic cations and of tetrahalometallate anions are stacked parallel to the ab plane. Antiparallel L+ cations disposed in a herring-bone pattern form pi-bonded chains through aromatic stacking. In the inorganic layer, adjacent tetrahedral CdI4 units have no connectivity but demonstrate close packing of iodide anions. In the crystal lattice of (II), the cations are arranged in stacks propagating along the a axis; the one-dimensional hydrogen-bonded polymer built of chloride ions and water molecules runs parallel to a column of stacked cations.

AB - The monocation product of the oxidative condensation-cyclization between two molecules of pyridine-2-carbaldehyde and one molecule of CH3NH2 center dot HCl in methanol, 2-methyl-3-(pyridin-2-yl)imidazo[1,5-a]pyridinium, was isolated in the presence of metal ions as bis[2-methyl-3-(pyridin-2-yl)imidazo[1,5-a]pyridin-2-ium] tetraiodocadmate, (C13H12N3)(2)[CdI4], (I), and the mixed chloride/nitrate salt, bis[2-methyl-3-(pyridin-2-yl)imidazo[1,5-a]pyridin-2-ium] 1.5-chloride 0.5-nitrate trihydrate, 2C(13)H(12)N(3)(+)center dot 1.5Cl(-)center dot 0.5NO(3)(-)center dot 3H(2)O, (II). Hybrid salt (I) crystallizes in the space group P2(1)/n with two [L](2)[CdI4] molecules in the asymmetric unit related by pseudosymmetry. In the crystal of (I), layers of organic cations and of tetrahalometallate anions are stacked parallel to the ab plane. Antiparallel L+ cations disposed in a herring-bone pattern form pi-bonded chains through aromatic stacking. In the inorganic layer, adjacent tetrahedral CdI4 units have no connectivity but demonstrate close packing of iodide anions. In the crystal lattice of (II), the cations are arranged in stacks propagating along the a axis; the one-dimensional hydrogen-bonded polymer built of chloride ions and water molecules runs parallel to a column of stacked cations.

KW - organic-inorganic hybrid

KW - tetrahalometallate

KW - crystal structure

KW - hydrogen-bonding interactions

KW - pi-pi stacking

KW - CYCLIZATION

KW - EMISSION

KW - CATION

U2 - 10.1107/S2056989019009964

DO - 10.1107/S2056989019009964

M3 - Article

VL - 75

SP - 1209-+

JO - Acta Crystallographica. Section E: Structure Reports Online

JF - Acta Crystallographica. Section E: Structure Reports Online

SN - 1600-5368

ER -