Triethylammonium 1,1′-binaphthyl-2,2′-diyl phosphate

Ravikumar R Gowda,Debashis Chakraborty,Venkatachalam Ramkumar

doi:10.1107/s160053681002026x

Ravikumar R Gowda, Debashis Chakraborty + Show 1 more

Open Access

https://doi.org/10.1107/s160053681002026x

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Abstract

In the crystal structure of the title compound, C6H16N+·C20H12O4P−, an N—H⋯O interaction links the cation to the anion. The N atom in the triethylammonium cation exhibits a trigonal-bipyramidal coordination geometry and forms an N—H⋯O interaction with one phosphate O atom of the 1,1′-binaphthyl-2,2′-diyl phosphate ligand. A bifurcated C—H⋯O interaction with the other phosphate O atom links molecules along the a axis. The dihedral angle between the two naphthyl ring systems is 58.92 (3)°. The refined Flack parameter value of 0.50 (10) indicates inversion twinning.

Highlights

H atoms treated by a mixture of independent and constrained refinement max = 0.54 e Å3
In the crystal structure of the title compound, C6H16N+C20H12O4P, an N—H O interaction links the cation to the anion
A recent report depicts phosphoric acid acts as Bronsted acid to catalyze the addition of enolizable βdiketones, β-ketoesters, and vinylogous amides to α,β-unsaturated aldehydes to lead to substituted chromenones, pyranones, and tetra hydroquinolinones in good yields under mild reaction conditions via a formal [3+3] cycloaddition (Moreau et al, 2009)

Summary

Data collection

H atoms treated by a mixture of independent and constrained refinement max = 0.54 e Å3. Key indicators: single-crystal X-ray study; T = 298 K; mean (C–C) = 0.003 Å; Rfactor = 0.043; wR factor = 0.121; data-to-parameter ratio = 18.7. In the crystal structure of the title compound, C6H16N+C20H12O4P, an N—H O interaction links the cation to the anion. The N atom in the triethylammonium cation exhibits a trigonal-bipyramidal coordination geometry and forms an N—. H O interaction with one phosphate O atom of the 1,10 binaphthyl-2,20 -diyl phosphate ligand. A bifurcated C—H O interaction with the other phosphate O atom links molecules along the a axis. The dihedral angle between the two naphthyl ring systems is 58.92 (3). The refined Flack parameter value of 0.50 (10) indicates inversion twinning

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Crystal data

Graphite monochromator phi and ω scans

Special details