N-(4-Fluorobenzoyl)-N′,N′′-diisopropylphosphoric triamide

The asymmetric unit of the title phosphoric triamide, C13H21FN3O2P, consists of two independent molecules. In each molecule, the P=O group and the N—H unit belonging to the C(O)NHP(O) fragment are in a syn conformation with respect to each other. An intramolecular N—H⋯O hydrogen bond occurs in each molecule. The P atom adopts a distorted tetrahedral environment. The methyl groups of an isopropyl fragment are disordered over two sets of sites with refined occupancies of 0.458 (5) and 0.542 (5). In the crystal, molecules are linked through N—H⋯O(=P) and N—H⋯O(=C) hydrogen bonds into chains along [001].


supplementary materials
The asymmetric unit of the title compound consists of two independent molecules. In one molecule, disorder with respect to the methyl carbon atoms C12 and C13 of an isopropyl group was treated using a two-part model (45.8/54.2) with restrained C-C distances of 1.55 (0.02) Å.
In the C(O)NHP(O) fragment, the phosphoryl group adopts a syn orientation with respect to the N-H unit. The P atoms are in a distorted tetrahedral environment as has been noted for other phosphoric triamides (Pourayoubi et al., 2011). The P═O, C═O and P-N bond lengths and the P-N-C bond angles are within the expected values (Pourayoubi et al., 2011;Raissi Shabari et al., 2012).
In the crystal structure, the molecules are linked through N-H···O(═P) and N-H···O(═C) hydrogen bonds into chains along [001], giving R 2 2 (8) and R 2 2 (12) rings (Fig. 2). This sequence of ring motifs is similar to most of the phosphoric tri-  To a solution of 4-F-C 6 H 4 C(O)NHP(O)Cl 2 (1 mmol) in chloroform (25 ml), a solution of isopropylamine (4 mmol) in chloroform (5 ml) was added at 273 K. After 4 h stirring, the solvent was removed and the product was washed with distilled water and recrystallized from a mixture of CH 3 OH/DMF (5:1 v/v) at room temperature.

Refinement
All non-hydrogen atoms refined anisotropically by full matrix least squares on F 2 . Disorder with respect to the methyl carbon atoms C12 and C13 of an isopropyl group was treated using a two part model (45.8/54.2) with restrained C-C distances of 1.55 (0.02) Å. Hydrogen atoms H1N, H2N, H3N, H4N, H5N, and H6N were found from a Fourier difference map and were refined isotropically with N-H distances of 0.87 (2) Å and 1.20 U eq of parent N atom. All other hydrogen atoms were placed in calculated positions with C-H distances of (C-HAr) 0.95 Å, (C-H) 1.00 Å, (CH 3 ) 0.98 Å and U eq of 1.20 and 1.50 of parent C atom.

Figure 1
An ORTEP-style plot and atom labeling scheme for the title compound. Displacement ellipsoids are given at 50% probability level and H atoms are drawn as small spheres of arbitrary radii.

N-(4-Fluorobenzoyl)-N′,N′′-diisopropylphosphoric triamide
Special details Experimental. IR (KBr, ν, cm -1 ): 3345, 3095, 2972, 1657, 1452, 1291, 1215, 1139, 1025, 887, 769, 683. Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 R-factors(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq Occ.  (8)