Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 3 (March 2013)

organic compounds

Acta Cryst. (2013). C69, 285-288    [ doi:10.1107/S0108270113003806 ]

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

J. Bacsa, M. Okello, P. Singh and V. Nair

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 [beta]-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 [beta]-C atom of the chain. Weak intra­molecular hydrogen bonds exist between the weakly acidic [alpha]-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 [beta]-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 1H and 13C NMR correlation spectroscopy study confirm that the same tautomer exists in solution as in the solid state.

Formula: C27H22F3N3O5

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[ doi:10.1107/S0108270113003806/fn31281sup3.cdx ]
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[ doi:10.1107/S0108270113003806/fn31281sup4.cml ]
Supplementary material


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