On the structure of 4-amino-(Z)-5-(4′-hydroxy-(E)-but-2′enylidene)-1,5-dihydro-2H-imidazol-2-one·H2O in the crystalline state

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Abstract

The structure of 4-amino-(Z)-5-(4′-hydroxy-(E)-but-2′-enlydinene)-1,5-dihydro-2H-imidazol-2-one monohydrate has been established by X-ray crystallography from diffractometer data: C7H9N3O2·H2O (Mr-185.18) crystallizes in the orthorhombic, space group P212121 with a-4.591 (1) Å, b=9.952 (3) Å, c-19.271 (3) Å, V-880.6 (6) Å3, Z-4, Dc-1.40 g cm-3 and μ(CuKα)=9.0 cm-1. The structure has been solved by direct methods and refined to R=0.037 for 777 observed reflections. While substantiating the molecular geometry inferred from NMR spectra, the X-ray analysis revealed that, in contrast to the preponderance of the 4-imino tautomer (IIb) in solution, in the crystalline state only the 4-amino form (IIa) is present. In solution, the 4-amino tautomer is terminated by the short intramolecular =CH⋯H(NH)- close contact of 2.14 Å repulsing hte contact amino proton to N(3), whereas in crystalline state the hydrogen-bond network developed between the molecules with the assitance of the solvent (water) molecule seems to account for its stability. Among others, the N(1)-H⋯N(3) intermolecular hydrogen bond hardly tolerates a simultaneously protonated N(3) atom required by tautomer IIb.

Original languageEnglish
Pages (from-to)257-263
Number of pages7
JournalJournal of Molecular Structure
Volume239
Issue numberC
DOIs
Publication statusPublished - okt. 15 1990

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tautomers
imidazoles
Hydrogen
Hydrogen bonds
Crystalline materials
Molecules
X ray crystallography
X Ray Crystallography
X ray analysis
Diffractometers
hydrogen bonds
Protons
Nuclear magnetic resonance
X-Rays
diffractometers
Atoms
crystallography
Geometry
Water
molecules

ASJC Scopus subject areas

  • Structural Biology
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Spectroscopy
  • Materials Science (miscellaneous)
  • Atomic and Molecular Physics, and Optics

Cite this

@article{4ce58fda12d0426a99f50ec9db60ba08,
title = "On the structure of 4-amino-(Z)-5-(4′-hydroxy-(E)-but-2′enylidene)-1,5-dihydro-2H-imidazol-2-one·H2O in the crystalline state",
abstract = "The structure of 4-amino-(Z)-5-(4′-hydroxy-(E)-but-2′-enlydinene)-1,5-dihydro-2H-imidazol-2-one monohydrate has been established by X-ray crystallography from diffractometer data: C7H9N3O2·H2O (Mr-185.18) crystallizes in the orthorhombic, space group P212121 with a-4.591 (1) {\AA}, b=9.952 (3) {\AA}, c-19.271 (3) {\AA}, V-880.6 (6) {\AA}3, Z-4, Dc-1.40 g cm-3 and μ(CuKα)=9.0 cm-1. The structure has been solved by direct methods and refined to R=0.037 for 777 observed reflections. While substantiating the molecular geometry inferred from NMR spectra, the X-ray analysis revealed that, in contrast to the preponderance of the 4-imino tautomer (IIb) in solution, in the crystalline state only the 4-amino form (IIa) is present. In solution, the 4-amino tautomer is terminated by the short intramolecular =CH⋯H(NH)- close contact of 2.14 {\AA} repulsing hte contact amino proton to N(3), whereas in crystalline state the hydrogen-bond network developed between the molecules with the assitance of the solvent (water) molecule seems to account for its stability. Among others, the N(1)-H⋯N(3) intermolecular hydrogen bond hardly tolerates a simultaneously protonated N(3) atom required by tautomer IIb.",
author = "G. Argay and A. K{\'a}lm{\'a}n and J. Kov{\'a}cs and I. Pint{\'e}r",
year = "1990",
month = "10",
day = "15",
doi = "10.1016/0022-2860(90)80219-A",
language = "English",
volume = "239",
pages = "257--263",
journal = "Journal of Molecular Structure",
issn = "0022-2860",
publisher = "Elsevier",
number = "C",

}

TY - JOUR

T1 - On the structure of 4-amino-(Z)-5-(4′-hydroxy-(E)-but-2′enylidene)-1,5-dihydro-2H-imidazol-2-one·H2O in the crystalline state

AU - Argay, G.

AU - Kálmán, A.

AU - Kovács, J.

AU - Pintér, I.

PY - 1990/10/15

Y1 - 1990/10/15

N2 - The structure of 4-amino-(Z)-5-(4′-hydroxy-(E)-but-2′-enlydinene)-1,5-dihydro-2H-imidazol-2-one monohydrate has been established by X-ray crystallography from diffractometer data: C7H9N3O2·H2O (Mr-185.18) crystallizes in the orthorhombic, space group P212121 with a-4.591 (1) Å, b=9.952 (3) Å, c-19.271 (3) Å, V-880.6 (6) Å3, Z-4, Dc-1.40 g cm-3 and μ(CuKα)=9.0 cm-1. The structure has been solved by direct methods and refined to R=0.037 for 777 observed reflections. While substantiating the molecular geometry inferred from NMR spectra, the X-ray analysis revealed that, in contrast to the preponderance of the 4-imino tautomer (IIb) in solution, in the crystalline state only the 4-amino form (IIa) is present. In solution, the 4-amino tautomer is terminated by the short intramolecular =CH⋯H(NH)- close contact of 2.14 Å repulsing hte contact amino proton to N(3), whereas in crystalline state the hydrogen-bond network developed between the molecules with the assitance of the solvent (water) molecule seems to account for its stability. Among others, the N(1)-H⋯N(3) intermolecular hydrogen bond hardly tolerates a simultaneously protonated N(3) atom required by tautomer IIb.

AB - The structure of 4-amino-(Z)-5-(4′-hydroxy-(E)-but-2′-enlydinene)-1,5-dihydro-2H-imidazol-2-one monohydrate has been established by X-ray crystallography from diffractometer data: C7H9N3O2·H2O (Mr-185.18) crystallizes in the orthorhombic, space group P212121 with a-4.591 (1) Å, b=9.952 (3) Å, c-19.271 (3) Å, V-880.6 (6) Å3, Z-4, Dc-1.40 g cm-3 and μ(CuKα)=9.0 cm-1. The structure has been solved by direct methods and refined to R=0.037 for 777 observed reflections. While substantiating the molecular geometry inferred from NMR spectra, the X-ray analysis revealed that, in contrast to the preponderance of the 4-imino tautomer (IIb) in solution, in the crystalline state only the 4-amino form (IIa) is present. In solution, the 4-amino tautomer is terminated by the short intramolecular =CH⋯H(NH)- close contact of 2.14 Å repulsing hte contact amino proton to N(3), whereas in crystalline state the hydrogen-bond network developed between the molecules with the assitance of the solvent (water) molecule seems to account for its stability. Among others, the N(1)-H⋯N(3) intermolecular hydrogen bond hardly tolerates a simultaneously protonated N(3) atom required by tautomer IIb.

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U2 - 10.1016/0022-2860(90)80219-A

DO - 10.1016/0022-2860(90)80219-A

M3 - Article

AN - SCOPUS:33749177057

VL - 239

SP - 257

EP - 263

JO - Journal of Molecular Structure

JF - Journal of Molecular Structure

SN - 0022-2860

IS - C

ER -