N-[Bis(benzylamino)phosphoryl]-2,2,2-trichloroacetamide

In the title compound, C16H17Cl3N3O2P, the P atom has a slightly distorted tetrahedral configuration. The conformations of the carbonyl and phosphoryl groups are anti to each other. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into infinite chains parallel to the b axis.


Related literature
In the title compound, the phosphorus atom has a slightly distorted tetrahedral configuration (Fig.1). The average values of the angles OPN in the molecule are larger than tetrahedral, while the N -P -N angles are smaller, with the exception O1 -P1-N1 106.85 (7) ° and N(1) -P1-N(2) 112.32 (7) °, which can be rationalized by the influence of the hydrogen bonds.
The environment of the nitrogen atoms is practically planar with only slight deviations from the mean planes.
The bond length P ═O (1.479 (1) Å is longer than in the compounds with alkyl amide substituents (the range of bond length d (P ═O) 1.475 -1.478 Å) (Amirkhanov et al., 1997b). In the structure the carbonyl and phosphoryl groups are anti to each other as in most carbacylamidophosphates.

Experimental
The solution of benzylamine (26.8 g, 0.25 mol) in 30 ml of chloroform was cooled to 10 °C and a solution of the dichloride of trichloroacetylamidophosphoric acid (14 g, 0.047 mol) in 150 ml of chloroform was added slowly with stirring. The temperature was not allowed to rise above 15 °C. Stirring was continued for about 40 min. The resulting mixture, containing HL, H 2 NCH 2 C 6 H 5 *HCl and excess dibenzylamine, was filtered from the precipitate (H 2 NCH 2 C 6 H 5 *HCl). Then the solution was evaporated and the residue was treated with aqueous HCl; the product precipitated as a yellow crystalline powder (90 % yield) (Kirsanov & Derkach, 1956). A colourless crystalline compound was obtained after recristallization from acetone. The compound is air stable, soluble in alcohols and hot acetone, insoluble in non-polar aprotic solvents and supplementary materials sup-2 Refinement All hydrogen atoms were located from electron density difference maps and included in the refinement in the riding motion approximation with U iso constrained to be 1.2 times U eq of the carrier atom.
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.