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 language | English |
|---|---|
| Pages (from-to) | 257-263 |
| Number of pages | 7 |
| Journal | Journal of Molecular Structure |
| Volume | 239 |
| Issue number | C |
| DOIs | |
| Publication status | Published - okt. 15 1990 |
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ASJC Scopus subject areas
- Structural Biology
- Organic Chemistry
- Physical and Theoretical Chemistry
- Spectroscopy
- Materials Science (miscellaneous)
- Atomic and Molecular Physics, and Optics
Cite this
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. / Argay, G.; Kálmán, A.; Kovács, J.; Pintér, I.
In: Journal of Molecular Structure, Vol. 239, No. C, 15.10.1990, p. 257-263.Research output: Article
}
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 -