Unknown

Dataset Information

0

Crystal structure and DFT study of the zwitterionic form of 3-{(E)-1-[(4-ethoxyphenyl)iminiumyl]ethyl}-6-methyl-2-oxo-2H-pyran-4-olate.

ABSTRACT: The title Schiff base compound, C16H17NO4, crystallizes as a zwitterion, with the phenolic H atom having been transferred to the imino group. The resulting iminium and hy-droxy groups are linked by an intra-molecular N-H?O hydrogen bond, enclosing an S(6) ring motif. The conformation about the C=N bond is E and the dihedral angle between the benzene and pyran rings is 70.49?(6)°. In the crystal, mol-ecules are linked by C-H?O hydrogen bonds, forming a three-dimensional supra-molecular structure. There are also C-H?? inter-actions and offset ?-? inter-actions, involving the pyran rings [inter-centroid distance = 3.4156?(8)?Å], which consolidate the three-dimensional structure. Quantum chemical calculations of the mol-ecule are in good agreement with the solid state keto-amine (NH) form of the title compound.

SUBMITTER: Djedouani A 

PROVIDER: S-EPMC5956330 | biostudies-literature | 2018 Feb

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Crystal structure and DFT study of the zwitterionic form of 3-{(<i>E</i>)-1-[(4-ethoxyphenyl)iminiumyl]ethyl}-6-methyl-2-oxo-2<i>H</i>-pyran-4-olate.

Djedouani Amel A   Anak Barkahem B   Tabti Salima S   Cleymand Franck F   François Michel M   Fleutot Solenne S  

Acta crystallographica. Section E, Crystallographic communications 20180116 Pt 2

The title Schiff base compound, C<sub>16</sub>H<sub>17</sub>NO<sub>4</sub>, crystallizes as a zwitterion, with the phenolic H atom having been transferred to the imino group. The resulting iminium and hy-droxy groups are linked by an intra-molecular N-H⋯O hydrogen bond, enclosing an <i>S</i>(6) ring motif. The conformation about the C=N bond is <i>E</i> and the dihedral angle between the benzene and pyran rings is 70.49 (6)°. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming  ...[more]

Similar Datasets

Unknown Zwitterionic 6-methyl-2-oxo-3-[1-(ureido-iminio)eth-yl]-2H-pyran-4-olate monohydrate.
| S-EPMC2960563 | biostudies-other
Unknown Ethyl 2-(3-acetyl-6-methyl-2-oxo-2H-pyran-4-yl-oxy)acetate.
| S-EPMC2979740 | biostudies-literature
Unknown 4-Hy-droxy-3-[(4-hy-droxy-6-methyl-2-oxo-3,6-dihydro-2H-pyran-3-yl)(3-thien-yl)meth-yl]-6-methyl-3,6-dihydro-2H-pyran-2-one.
| S-EPMC3051638 | biostudies-literature
Unknown Bis(3-acetyl-6-methyl-2-oxo-2H-pyran-4-olato)bis-(dimethyl sulfoxide)nickel(II).
| S-EPMC2970285 | biostudies-literature
Unknown (7-Chloro-2-oxo-2H-chromen-4-yl)methyl di-ethyl-carbamodi-thio-ate.
| S-EPMC3884430 | biostudies-literature
Unknown Crystal structures of 4-methyl-2-oxo-2H-chromene-7,8-diyl di-acetate and 4-methyl-2-oxo-2H-chromene-7,8-diyl bis-(pent-4-ynoate).
| S-EPMC4908516 | biostudies-literature
Unknown 2-Oxo-2-(2-oxo-2H-chromen-3-yl)ethyl di-ethyl-dithio-carbamate.
| S-EPMC3884423 | biostudies-literature
Unknown 2-(4-Methoxyphenoxy)-6-methyl-3-oxo-3,6-dihydro-2H-pyran-4-yl benzoate.
| S-EPMC2968613 | biostudies-other
Unknown Crystal structure and Hirshfeld surface analysis of ethyl 2'-amino-5-bromo-3'-cyano-6'-methyl-2-oxo-spiro-[indoline-3,4'-pyran]-5'-carboxyl-ate.
| S-EPMC9443792 | biostudies-literature
Unknown Crystal structure of 3-{1-[(1-allyl-1H-indazol-6-yl)amino]-ethyl-idene}-6-methyl-2H-pyran-2,4(3H)-dione.
| S-EPMC4257434 | biostudies-other