p-Tolylmethanaminium cyclohexane-1,2-diyl phosphate

In the title molecular salt, C8H12N+·C6H10O4P−, the cation and anion are connected by N—H⋯O hydrogen bonds. The C atoms of the cyclohexane ring are disordered over two sets of sites in a 0.51 (4):0.49 (4) occupancy ratio to generate two superimposed chair conformations. One of the terminal phosphate O atoms is also disordered in a 0.62 (2):0.38 (2) ratio.

In the title molecular salt, C 8 H 12 N + ÁC 6 H 10 O 4 P À , the cation and anion are connected by N-HÁ Á ÁO hydrogen bonds. The C atoms of the cyclohexane ring are disordered over two sets of sites in a 0.51 (4):0.49 (4) occupancy ratio to generate two superimposed chair conformations. One of the terminal phosphate O atoms is also disordered in a 0.62 (2):0.38 (2) ratio.
The C atoms of the cyclohexane ring are disordered, with a site-occupancy factor of 0.51 (4) for the major component and the O atom attached to the phosphate is also disordered, with a site-occupancy factor of 0.62 (2).
The N atom in the p-tolyl methanammonium cation exhibits a trigonal pyramidal coordinate geometry with three phosphate O atom forming three N-H···O interactions.
White fumes of HCl were observed upon addition, reaction mixture was stirred at 273 K for 30 min. Then 0.8 ml (6.5 mmol) 4-methylbenzylamine was added slowly at 273 K. Reaction mixture was stirred at 273 K for 1 h and warmed up to room temperature and stirred for 48 h. The reaction was monitored using thin layer chromatography. The reaction mixture was then washed with 2 ml of water. The product was extracted using dichloromethane and purified by crystallization in dichloromethane to yield colourless blocks of (I).

Refinement
All H atoms except the nitrogen H atoms were fixed geometrically and allowed to ride on the parent C atoms with aromatic C-H = 0.93 Å, aliphatic C-H = 0.98 Å, methine C-H = 0.97 Å, methylene C-H = 0.97 Å and methyl C-H = 0.96 Å. The displacement parameters were set for phenyl, methine and aliphatic H atoms at U iso (H) = 1.2U eq (C) and methyl H atoms at U iso (H) = 1.5U eq (C) The cyclohexane ring C9-C14 are disordered in two orientations with refined site occupancy of 0.51 (4) and 0.49 (5) respectively. The O atom attached to the phosphate is also disordered, with a site-occupancy factor of 0.62 (2) and 0.38 (3) respectively. Some anisotropic displacement ellipsoids were rather elongated which led us to use the EADP restraints. Fig. 1. View of (I) with atoms represented as 30% probability ellipsoids.

Special details
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 > 2sigma(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. (