Cyclohexylammonium acetate–N,N′,N′′-tricyclohexylphosphoric triamide (1/1)

In the phosphoric triamide molecule of the title compound, C6H14N+·C2H3O2 −·C18H36N3OP, the P atom displays a distorted tetrahedral geometry and the cyclohexyl rings adopt chair conformations with the NH groups in equatorial positions. In the crystal, the cations, anions and phosphoric triamide molecules are linked via N—H⋯O hydrogen bonds into a two-dimensional array parallel to the bc plane. The O atom of the P(O) group acts as a double-hydrogen-bond acceptor.

In the phosphoric triamide molecule of the title compound, C 6 H 14 N + ÁC 2 H 3 O 2 À ÁC 18 H 36 N 3 OP, the P atom displays a distorted tetrahedral geometry and the cyclohexyl rings adopt chair conformations with the NH groups in equatorial positions. In the crystal, the cations, anions and phosphoric triamide molecules are linked via N-HÁ Á ÁO hydrogen bonds into a two-dimensional array parallel to the bc plane. The O atom of the P(O) group acts as a double-hydrogen-bond acceptor.

D-HÁ
The cyclohexyl rings of phosphoric triamide molecule and also in the C 6 H 11 NH 3 + cation have the chair conformation and the NH and NH 3 + groups are in the equatorial position of the rings. In P(O)(NHC 6 H 11 ) 3 , the P atom exists in a distorted tetrahedral environment with the P-N bond lengths of 1.6315 (14) Å, 1.6440 (14) Å and 1.6463 (14) Å (for P1-N1).
The P═O bond length and the P-N-C bond angles are standard for the phosphoric triamides (Pourayoubi, Tarahhomi et al., 2012 andSabbaghi et al., 2011).

Experimental
The title co-crystal was obtained fortuitously from a reaction between phosphoryl chloride and cyclohexylamine in acetonitrile at 273 K (4 h) and then the treatment of dibenzylamine at ice bath temperature. The presence of acetate anion is attributed to the hydrolysis of acetonitrile in acidic media of reaction (Vollhardt & Schore, 1998).

Refinement
Structure was solved by direct methods and all non-hydrogen atoms were refined by full matrix least squares on F 2 . All nitrogen hydrogen atoms were found from a Fourier difference map and were refined isotropically with N-H distance of 0.87 (2) Å and 1.2U eq of parent N atom. All other H atoms were placed in calculated positions and treated as riding on their parent atoms with C-H = 0.980 Å (CH 3 ), 0.990 Å (CH 2 ), and 1.000 Å (CH) with 1.5U eq for methyl groups and 1.2U eq for other H atoms.  An ORTEP-style plot and atom labeling scheme for the title cocrystal. Displacement ellipsoids are given at 50% probability level and H atoms are drawn as small spheres of arbitrary radii.    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 P1 0.03749 (