Crystal structures of two 1

2 dihydrate compounds of chloranilic acid with 2-carboxypyridine and 2-carboxyquinoline

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Abstract

The crystal structure of the 1:2 dihydrate compound of chloranilic acid (systematic name: 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone) with 2-carboxypyridine (another common name: picolinic acid; systematic name: pyridine-2-carboxylic acid), namely, 2C 6 H 5.5 NO 2 0.5+ C 6 HCl 2 O 4-2H 2 O, (I), has been determined at 180K, and the structure of the 1:2 dihydrate compound of chloranilic acid with 2-carboxyquinoline (another common name: quinaldic acid; systematic name: quinoline-2-carboxylic acid), namely, 2C 10 H 7 NO 2 C 6 H 2 Cl 2 O 4 2H 2 O, (II), has been redetermined at 200K. This determination presents a higher precision crystal structure than the previously published structure [Marfo-Owusu & Thompson (2014). X-ray Struct. Anal. Online, 30, 55-56]. Compound (I) was analysed as a disordered structure over two states, viz. salt and co-crystal. The salt is bis(2-carboxypyridinium) chloranilate dihydrate, 2C 6 H 6 NO 2 + C 6 Cl 2 O 4 2-2H 2 O, and the co-crystal is bis(pyridinium-2-carboxylate) chloranilic acid dihydrate, 2C 6 H 5 NO 2 C 6 H 2 Cl 2 O 4 2H 2 O, including zwitterionic 2-carboxypyridine. In both salt and co-crystal, the water molecule links the chloranilic acid and 2-carboxypyridine molecules through O-HO and N-HO hydrogen bonds. The 2-carboxypyridine molecules are connected into a head-to-head inversion dimer by a short O-HO hydrogen bond, in which the H atom is disordered over two positions. Compound (II) is a 1:2 dihydrate co-crystal of chloranilic acid and zwitterionic 2-carboxyquinoline. The water molecule links the chloranilic acid and 2-carboxyquinoline molecules through O-HO hydrogen bonds. The 2-carboxyquinoline molecules are connected into a head-to-tail inversion dimer by a pair of N-HO hydrogen bonds.

Original languageEnglish
Pages (from-to)1840-1844
Number of pages5
JournalActa Crystallographica Section E: Crystallographic Communications
Volume73
DOIs
Publication statusPublished - Jan 1 2017

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Crystal structure
acids
crystal structure
Molecules
Acids
Hydrogen bonds
Crystals
Salts
hydrogen bonds
molecules
Dimers
salts
Carboxylic acids
carboxylic acids
crystals
Water
dimers
inversions
Carboxylic Acids
chloranilic acid

Keywords

  • 2-carboxypyridine
  • 2-carboxyquinoline
  • chloranilic acid
  • crystal structure
  • disorder
  • hydrogen bond
  • twitterion

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)
  • Condensed Matter Physics

Cite this

@article{fe7f6183cb5f4f0f8d97d1c9c53c90f5,
title = "Crystal structures of two 1: 2 dihydrate compounds of chloranilic acid with 2-carboxypyridine and 2-carboxyquinoline",
abstract = "The crystal structure of the 1:2 dihydrate compound of chloranilic acid (systematic name: 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone) with 2-carboxypyridine (another common name: picolinic acid; systematic name: pyridine-2-carboxylic acid), namely, 2C 6 H 5.5 NO 2 0.5+ C 6 HCl 2 O 4-2H 2 O, (I), has been determined at 180K, and the structure of the 1:2 dihydrate compound of chloranilic acid with 2-carboxyquinoline (another common name: quinaldic acid; systematic name: quinoline-2-carboxylic acid), namely, 2C 10 H 7 NO 2 C 6 H 2 Cl 2 O 4 2H 2 O, (II), has been redetermined at 200K. This determination presents a higher precision crystal structure than the previously published structure [Marfo-Owusu & Thompson (2014). X-ray Struct. Anal. Online, 30, 55-56]. Compound (I) was analysed as a disordered structure over two states, viz. salt and co-crystal. The salt is bis(2-carboxypyridinium) chloranilate dihydrate, 2C 6 H 6 NO 2 + C 6 Cl 2 O 4 2-2H 2 O, and the co-crystal is bis(pyridinium-2-carboxylate) chloranilic acid dihydrate, 2C 6 H 5 NO 2 C 6 H 2 Cl 2 O 4 2H 2 O, including zwitterionic 2-carboxypyridine. In both salt and co-crystal, the water molecule links the chloranilic acid and 2-carboxypyridine molecules through O-HO and N-HO hydrogen bonds. The 2-carboxypyridine molecules are connected into a head-to-head inversion dimer by a short O-HO hydrogen bond, in which the H atom is disordered over two positions. Compound (II) is a 1:2 dihydrate co-crystal of chloranilic acid and zwitterionic 2-carboxyquinoline. The water molecule links the chloranilic acid and 2-carboxyquinoline molecules through O-HO hydrogen bonds. The 2-carboxyquinoline molecules are connected into a head-to-tail inversion dimer by a pair of N-HO hydrogen bonds.",
keywords = "2-carboxypyridine, 2-carboxyquinoline, chloranilic acid, crystal structure, disorder, hydrogen bond, twitterion",
author = "Kazuma Gotoh and Hiroyuki Ishida",
year = "2017",
month = "1",
day = "1",
doi = "10.1107/S2056989017015997",
language = "English",
volume = "73",
pages = "1840--1844",
journal = "Acta Crystallographica Section E: Crystallographic Communications",
issn = "2056-9890",
publisher = "International Union of Crystallography",

}

TY - JOUR

T1 - Crystal structures of two 1

T2 - 2 dihydrate compounds of chloranilic acid with 2-carboxypyridine and 2-carboxyquinoline

AU - Gotoh, Kazuma

AU - Ishida, Hiroyuki

PY - 2017/1/1

Y1 - 2017/1/1

N2 - The crystal structure of the 1:2 dihydrate compound of chloranilic acid (systematic name: 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone) with 2-carboxypyridine (another common name: picolinic acid; systematic name: pyridine-2-carboxylic acid), namely, 2C 6 H 5.5 NO 2 0.5+ C 6 HCl 2 O 4-2H 2 O, (I), has been determined at 180K, and the structure of the 1:2 dihydrate compound of chloranilic acid with 2-carboxyquinoline (another common name: quinaldic acid; systematic name: quinoline-2-carboxylic acid), namely, 2C 10 H 7 NO 2 C 6 H 2 Cl 2 O 4 2H 2 O, (II), has been redetermined at 200K. This determination presents a higher precision crystal structure than the previously published structure [Marfo-Owusu & Thompson (2014). X-ray Struct. Anal. Online, 30, 55-56]. Compound (I) was analysed as a disordered structure over two states, viz. salt and co-crystal. The salt is bis(2-carboxypyridinium) chloranilate dihydrate, 2C 6 H 6 NO 2 + C 6 Cl 2 O 4 2-2H 2 O, and the co-crystal is bis(pyridinium-2-carboxylate) chloranilic acid dihydrate, 2C 6 H 5 NO 2 C 6 H 2 Cl 2 O 4 2H 2 O, including zwitterionic 2-carboxypyridine. In both salt and co-crystal, the water molecule links the chloranilic acid and 2-carboxypyridine molecules through O-HO and N-HO hydrogen bonds. The 2-carboxypyridine molecules are connected into a head-to-head inversion dimer by a short O-HO hydrogen bond, in which the H atom is disordered over two positions. Compound (II) is a 1:2 dihydrate co-crystal of chloranilic acid and zwitterionic 2-carboxyquinoline. The water molecule links the chloranilic acid and 2-carboxyquinoline molecules through O-HO hydrogen bonds. The 2-carboxyquinoline molecules are connected into a head-to-tail inversion dimer by a pair of N-HO hydrogen bonds.

AB - The crystal structure of the 1:2 dihydrate compound of chloranilic acid (systematic name: 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone) with 2-carboxypyridine (another common name: picolinic acid; systematic name: pyridine-2-carboxylic acid), namely, 2C 6 H 5.5 NO 2 0.5+ C 6 HCl 2 O 4-2H 2 O, (I), has been determined at 180K, and the structure of the 1:2 dihydrate compound of chloranilic acid with 2-carboxyquinoline (another common name: quinaldic acid; systematic name: quinoline-2-carboxylic acid), namely, 2C 10 H 7 NO 2 C 6 H 2 Cl 2 O 4 2H 2 O, (II), has been redetermined at 200K. This determination presents a higher precision crystal structure than the previously published structure [Marfo-Owusu & Thompson (2014). X-ray Struct. Anal. Online, 30, 55-56]. Compound (I) was analysed as a disordered structure over two states, viz. salt and co-crystal. The salt is bis(2-carboxypyridinium) chloranilate dihydrate, 2C 6 H 6 NO 2 + C 6 Cl 2 O 4 2-2H 2 O, and the co-crystal is bis(pyridinium-2-carboxylate) chloranilic acid dihydrate, 2C 6 H 5 NO 2 C 6 H 2 Cl 2 O 4 2H 2 O, including zwitterionic 2-carboxypyridine. In both salt and co-crystal, the water molecule links the chloranilic acid and 2-carboxypyridine molecules through O-HO and N-HO hydrogen bonds. The 2-carboxypyridine molecules are connected into a head-to-head inversion dimer by a short O-HO hydrogen bond, in which the H atom is disordered over two positions. Compound (II) is a 1:2 dihydrate co-crystal of chloranilic acid and zwitterionic 2-carboxyquinoline. The water molecule links the chloranilic acid and 2-carboxyquinoline molecules through O-HO hydrogen bonds. The 2-carboxyquinoline molecules are connected into a head-to-tail inversion dimer by a pair of N-HO hydrogen bonds.

KW - 2-carboxypyridine

KW - 2-carboxyquinoline

KW - chloranilic acid

KW - crystal structure

KW - disorder

KW - hydrogen bond

KW - twitterion

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U2 - 10.1107/S2056989017015997

DO - 10.1107/S2056989017015997

M3 - Article

VL - 73

SP - 1840

EP - 1844

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

SN - 2056-9890

ER -