Crystal structure of anilazine

The title compound [systematic name: 4,6-dichloro-N-(2-chlorophenyl)-1,3,5-triazin-2-amine], C9H5Cl3N4, is a triazine fungicide. The dihedral angle between the planes of the triazine and benzene rings is 4.04 (8)°. In the crystal, two weak C—H⋯N hydrogen bonds and short Cl⋯Cl contacts [3.4222 (4) Å] link adjacent molecules, forming two-dimensional networks parellel to the (112) plane. The planes are linked by weak intermolecular π–π interactions [3.6428 (5) and 3.6490 (5) Å], resulting in a three-dimensional architecture.


S2. Experimental
The title compound was purchased from the Dr. Ehrenstorfer GmbH Company. Slow evaporation of a solution in CHCl 3 gave single crystals suitable for X-ray analysis.

S3. Refinement
All H-atoms were positioned geometrically and refined using a riding model with d(C-H) = 0.95 Å, U iso = 1.2U eq (C) for aromatic C-H groups.

Figure 1
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.

Figure 2
Packing diagram of the title compound with C-H···N hydrogen bonds and short Cl···Cl contacts shown as dashed lines.

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.