1-(4-Chlorobenzylideneamino)pyridinum iodide

In the title compound, C12H10ClN2 +·I−, the aromatic rings are oriented at a dihedral angle of 54.55 (3)°. In the crystal structure, intermolecular C—H⋯I and C—H⋯Cl hydrogen bonds link the molecules.

In the title compound, C 12 H 10 ClN 2 + ÁI À , the aromatic rings are oriented at a dihedral angle of 54.55 (3) . In the crystal structure, intermolecular C-HÁ Á ÁI and C-HÁ Á ÁCl hydrogen bonds link the molecules.
In the molecule of the title compound ( Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges.
In the crystal structure, intramolecular C-H···I and intermolecular C-H···Cl hydrogen bonds (Table 1)

S2. Experimental
For the preparation of the title compound, 1-aminopyridinium iodide (22.2 g, 0.10 mol) was dissolved in ethanol (20 ml), 4-methylbenzaldehyde (12.4 g, 0.1 mol) was added with stirring, and then the mixture was heated at reflux for 5 h. Upon cooling to room temperature, a precipitate formed, which was collected by filtration and washed with cold ethanol (2 X 10 ml) to obtain a yellow solid (yield; 24.0 g, 70%). Crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution.

S3. Refinement
H atoms were positioned geometrically, with C-H = 0.93 Å for aromatic and methine H and constrained to ride on their parent atoms, with U iso (H) = 1.2U eq (C).  The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are 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.