Crystal structure of 4,6-diamino-2,2-dimethyl-3-[3-(2,4,5-trichlorophenoxy)propoxy]-2,3-dihydro-1,3,5-triazin-1-ium chloride methanol monosolvate

In the title methanol-solvated salt, C14H19Cl3N5O2 +·Cl−·CH3OH, the triazine molecule is protonated at one of the triazine N atoms. In the crystal, the triazine cations are linked through a pair of N—H⋯N hydrogen bonds, with graph-set R 2 2(8), forming an inversion dimer. The protonated N atom and the 2- and 4-amino groups of the triazine cation interact with the chloride anion through N—H⋯Cl hydrogen bonds, leading to the formation of a tape structure running along the b-axis direction. A short Cl⋯Cl contact [3.2937 (9) Å] is observed in the tape. The methanol molecule is linked to the chloride anion and the triazine cation, respectively, by an O—H⋯Cl hydrogen bond and a C—H⋯O interaction.

In the title compound, the WR99210 molecule is protonated at one of the nitrogen atoms of the triazine moiety. This is In the crystal, the triazine moiety is centrosymmetrically paired through N-H···N hydrogen bonds involving the 2amino group and the N3 atom of the triazine, leading to a hydrogen-bonding pattern with a graph-set R 2 2 (8) (Fig. 2). The pairs further interact with the chloride anion through N-H···Cl hydrogen bonds. The chloride anion connects 2-amino and 4-amino groups on either side of the paired triazine, forming an eight-membered hydrogen bonded ring motif with a graph-set R 3 2 (8). The protonated N1 and 2-amino groups of the cationic triazine also interacted with two chloride anions to form a ring motif with a graph-set R 4 2 (12). In addition, we found a graph-set R 3 2 (15) ring motif through an O-H···Cl hydrogen bond between the methanol molecule and the chloride anion as well as a C-H···O hydrogen bond between the benzene ring (C14) and the methanol molecule (Table 1).

S2. Experimental
WR99210 was a kind gift from Dr. Bongkoch Tarnchompoo, BIOTEC, National Science and Technology Development Agency, Thailand. Single crystals of the title compound were prepared from a methanolic solution by slow evaporation at 298 K. The colorless crystals suitable for X-ray diffraction were obtained after a few days.

S3. Refinement
The N-bound H atoms were located in a difference Fourier map and were refined with restraint of N-H = 0.88 (1) Å. All other H atoms were placed in idealized positions and refined as riding atoms, with C-H = 0.93-0.97 Å and O-H = 0.82 Å, and with U iso (H) = 1.5U eq (O, C methyl ) and 1.2U eq (C) for other H atoms.

Figure 1
View of the molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level.

Special details
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.