Unknown

Dataset Information

0

Solid-state tautomeric structure and invariom refinement of a novel and potent HIV integrase inhibitor.


ABSTRACT: The conformation and tautomeric structure of (Z)-4-[5-(2,6-difluorobenzyl)-1-(2-fluorobenzyl)-2-oxo-1,2-dihydropyridin-3-yl]-4-hydroxy-2-oxo-N-(2-oxopyrrolidin-1-yl)but-3-enamide, C27H22F3N3O5, in the solid state has been resolved by single-crystal X-ray crystallography. The electron distribution in the molecule was evaluated by refinements with invarioms, aspherical scattering factors by the method of Dittrich et al. [Acta Cryst. (2005), A61, 314-320] that are based on the Hansen-Coppens multipole model [Hansen & Coppens (1978). Acta Cryst. A34, 909-921]. The ?-diketo portion of the molecule exists in the enol form. The enol -OH hydrogen forms a strong asymmetric hydrogen bond with the carbonyl O atom on the ?-C atom of the chain. Weak intramolecular hydrogen bonds exist between the weakly acidic ?-CH hydrogen of the keto-enol group and the pyridinone carbonyl O atom, and also between the hydrazine N-H group and the carbonyl group in the ?-position from the hydrazine N-H group. The electrostatic properties of the molecule were derived from the molecular charge density. The molecule is in a lengthened conformation and the rings of the two benzyl groups are nearly orthogonal. Results from a high-field (1)H and (13)C NMR correlation spectroscopy study confirm that the same tautomer exists in solution as in the solid state.

SUBMITTER: Bacsa J 

PROVIDER: S-EPMC3589111 | biostudies-literature | 2013 Mar

REPOSITORIES: biostudies-literature

altmetric image

Publications

Solid-state tautomeric structure and invariom refinement of a novel and potent HIV integrase inhibitor.

Bacsa John J   Okello Maurice M   Singh Pankaj P   Nair Vasu V  

Acta crystallographica. Section C, Crystal structure communications 20130214 Pt 3


The conformation and tautomeric structure of (Z)-4-[5-(2,6-difluorobenzyl)-1-(2-fluorobenzyl)-2-oxo-1,2-dihydropyridin-3-yl]-4-hydroxy-2-oxo-N-(2-oxopyrrolidin-1-yl)but-3-enamide, C27H22F3N3O5, in the solid state has been resolved by single-crystal X-ray crystallography. The electron distribution in the molecule was evaluated by refinements with invarioms, aspherical scattering factors by the method of Dittrich et al. [Acta Cryst. (2005), A61, 314-320] that are based on the Hansen-Coppens multip  ...[more]

Similar Datasets

| S-EPMC8829933 | biostudies-literature
| S-EPMC8297771 | biostudies-literature
| S-EPMC545538 | biostudies-literature
| S-EPMC3274775 | biostudies-literature
| S-EPMC5118987 | biostudies-literature
| S-EPMC3257385 | biostudies-literature
| S-EPMC8739831 | biostudies-literature
| S-EPMC20173 | biostudies-literature
| S-EPMC3846259 | biostudies-literature
| S-EPMC3115487 | biostudies-literature