Crystal structures of two hydrogen-bonded compounds of chloranilic acid-ethyleneurea (1/1) and chloranilic acid-hydantoin (1/2)

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Abstract

The structures of the hydrogen-bonded 1:1 co-crystal of chloranilic acid (systematic name: 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone) with ethyleneurea (systematic name: imidazolidin-2-one), C6H2Cl2O4·C3H6N2O, (I), and the 1:2 co-crystal of chloranilic acid with hydantoin (systematic name: imidazolidine-2,4-dione), C6H2Cl2O4·2C3H4N2O2, (II), have been determined at 180 K. In the crystals of both compounds, the base molecules are in the lactam form and no acid-base interaction involving H-atom transfer is observed. The asymmetric unit of (I) consists of two independent half-molecules of chloranilic acid, with each of the acid molecules lying about an inversion centre, and one ethyleneurea molecule. The asymmetric unit of (II) consists of one half-molecule of chloranilic acid, which lies about an inversion centre, and one hydantoin molecule. In the crystal of (I), the acid and base molecules are linked via O - H⋯O and N - H⋯O hydrogen bonds, forming an undulating sheet structure parallel to the ab plane. In (II), the base molecules form an inversion dimer via a pair of N - H⋯O hydrogen bonds, and the base dimers are further linked through another N - H⋯O hydrogen bond into a layer structure parallel to ( 01). The acid molecule and the base molecule are linked via an O - H⋯O hydrogen bond.

Original languageEnglish
Pages (from-to)1727-1730
Number of pages4
JournalActa Crystallographica Section E: Crystallographic Communications
Volume74
DOIs
Publication statusPublished - Jan 1 2018

Fingerprint

Hydantoins
Crystal structure
acids
crystal structure
Molecules
Acids
hydrogen
molecules
Hydrogen bonds
hydrogen bonds
Crystals
inversions
Dimers
crystals
dimers
chloranilic acid
Lactams
quinones
Dione
Hydrogen

Keywords

  • chloranilic acid
  • crystal structure
  • ethyleneurea
  • hydantoin
  • hydrogen bond
  • imidazolidin-2-one
  • imidazolidine-2,4-dione

ASJC Scopus subject areas

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

Cite this

@article{4c2d2ab9dfd74feeac58aff4631d0bb3,
title = "Crystal structures of two hydrogen-bonded compounds of chloranilic acid-ethyleneurea (1/1) and chloranilic acid-hydantoin (1/2)",
abstract = "The structures of the hydrogen-bonded 1:1 co-crystal of chloranilic acid (systematic name: 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone) with ethyleneurea (systematic name: imidazolidin-2-one), C6H2Cl2O4·C3H6N2O, (I), and the 1:2 co-crystal of chloranilic acid with hydantoin (systematic name: imidazolidine-2,4-dione), C6H2Cl2O4·2C3H4N2O2, (II), have been determined at 180 K. In the crystals of both compounds, the base molecules are in the lactam form and no acid-base interaction involving H-atom transfer is observed. The asymmetric unit of (I) consists of two independent half-molecules of chloranilic acid, with each of the acid molecules lying about an inversion centre, and one ethyleneurea molecule. The asymmetric unit of (II) consists of one half-molecule of chloranilic acid, which lies about an inversion centre, and one hydantoin molecule. In the crystal of (I), the acid and base molecules are linked via O - H⋯O and N - H⋯O hydrogen bonds, forming an undulating sheet structure parallel to the ab plane. In (II), the base molecules form an inversion dimer via a pair of N - H⋯O hydrogen bonds, and the base dimers are further linked through another N - H⋯O hydrogen bond into a layer structure parallel to ( 01). The acid molecule and the base molecule are linked via an O - H⋯O hydrogen bond.",
keywords = "chloranilic acid, crystal structure, ethyleneurea, hydantoin, hydrogen bond, imidazolidin-2-one, imidazolidine-2,4-dione",
author = "Kazuma Gotoh and Hiroyuki Ishida",
year = "2018",
month = "1",
day = "1",
doi = "10.1107/S205698901801561X",
language = "English",
volume = "74",
pages = "1727--1730",
journal = "Acta Crystallographica Section E: Crystallographic Communications",
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TY - JOUR

T1 - Crystal structures of two hydrogen-bonded compounds of chloranilic acid-ethyleneurea (1/1) and chloranilic acid-hydantoin (1/2)

AU - Gotoh, Kazuma

AU - Ishida, Hiroyuki

PY - 2018/1/1

Y1 - 2018/1/1

N2 - The structures of the hydrogen-bonded 1:1 co-crystal of chloranilic acid (systematic name: 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone) with ethyleneurea (systematic name: imidazolidin-2-one), C6H2Cl2O4·C3H6N2O, (I), and the 1:2 co-crystal of chloranilic acid with hydantoin (systematic name: imidazolidine-2,4-dione), C6H2Cl2O4·2C3H4N2O2, (II), have been determined at 180 K. In the crystals of both compounds, the base molecules are in the lactam form and no acid-base interaction involving H-atom transfer is observed. The asymmetric unit of (I) consists of two independent half-molecules of chloranilic acid, with each of the acid molecules lying about an inversion centre, and one ethyleneurea molecule. The asymmetric unit of (II) consists of one half-molecule of chloranilic acid, which lies about an inversion centre, and one hydantoin molecule. In the crystal of (I), the acid and base molecules are linked via O - H⋯O and N - H⋯O hydrogen bonds, forming an undulating sheet structure parallel to the ab plane. In (II), the base molecules form an inversion dimer via a pair of N - H⋯O hydrogen bonds, and the base dimers are further linked through another N - H⋯O hydrogen bond into a layer structure parallel to ( 01). The acid molecule and the base molecule are linked via an O - H⋯O hydrogen bond.

AB - The structures of the hydrogen-bonded 1:1 co-crystal of chloranilic acid (systematic name: 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone) with ethyleneurea (systematic name: imidazolidin-2-one), C6H2Cl2O4·C3H6N2O, (I), and the 1:2 co-crystal of chloranilic acid with hydantoin (systematic name: imidazolidine-2,4-dione), C6H2Cl2O4·2C3H4N2O2, (II), have been determined at 180 K. In the crystals of both compounds, the base molecules are in the lactam form and no acid-base interaction involving H-atom transfer is observed. The asymmetric unit of (I) consists of two independent half-molecules of chloranilic acid, with each of the acid molecules lying about an inversion centre, and one ethyleneurea molecule. The asymmetric unit of (II) consists of one half-molecule of chloranilic acid, which lies about an inversion centre, and one hydantoin molecule. In the crystal of (I), the acid and base molecules are linked via O - H⋯O and N - H⋯O hydrogen bonds, forming an undulating sheet structure parallel to the ab plane. In (II), the base molecules form an inversion dimer via a pair of N - H⋯O hydrogen bonds, and the base dimers are further linked through another N - H⋯O hydrogen bond into a layer structure parallel to ( 01). The acid molecule and the base molecule are linked via an O - H⋯O hydrogen bond.

KW - chloranilic acid

KW - crystal structure

KW - ethyleneurea

KW - hydantoin

KW - hydrogen bond

KW - imidazolidin-2-one

KW - imidazolidine-2,4-dione

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U2 - 10.1107/S205698901801561X

DO - 10.1107/S205698901801561X

M3 - Article

AN - SCOPUS:85058063817

VL - 74

SP - 1727

EP - 1730

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

SN - 2056-9890

ER -