3-Acetyl-2,4-dimethylquinolin-1-ium chloride

In the title salt, C13H14NO+·Cl−, the dihedral angle between the fused ring system (r.m.s. deviation = 0.039 Å) and the attached aldehyde group is 75.27 (16)°. In the crystal, the cation and anion are linked by an N—H⋯Cl hydrogen bond and the resulting pairs are connected into four-ion aggregates by π–π interactions between the C6 and pyridinium rings [3.6450 (9) Å] of inversion-related quinolinium residues.

In the title salt, C 13 H 14 NO + ÁCl À , the dihedral angle between the fused ring system (r.m.s. deviation = 0.039 Å ) and the attached aldehyde group is 75.27 (16) . In the crystal, the cation and anion are linked by an N-HÁ Á ÁCl hydrogen bond and the resulting pairs are connected into four-ion aggregates byinteractions between the C 6 and pyridinium rings [3.6450 (9) Å ] of inversion-related quinolinium residues.

D-HÁ
The fused-ring system of the cation in (I), Fig. 1, is almost planar with the r.m.s. deviation of the fitted atoms being 0.039 Å; maximum deviations are 0.051 (1) Å for the C3 atom and -0.044 (2) Å for the C5 atom. The aldehyde group is almost perpendicular to this plane, forming a C10-C9-C12-O1 torsion angle of 73.64 (18)°.
In the crystal, ions are linked by a N-H···Cl hydrogen bond, Table 1, and connected into four-ion aggregates by π-π interactions between the C 6 and pyridinium rings [inter-centorid distance 3.6450 (9) Å for symmetry operation 1 -x, 1 -y, 1 -z] of centrosymmetrically related quinolinyl residues, Fig. 2. These pack with no specific interactions between them.

Experimental
A mixture of 2-aminoacetophenone (0.68 g, 0.005 M), acetylacetone (0.5 g, 0.005 M) and 1 N HCl (20 ml) was stirred at 363 K for 45 minutes. To the resulting mixture, chloroform (20 ml) was added and the organic layer was passed through anhydrous Na 2 SO 4 . Re-crystallization was by slow evaporation of chloroform solution of (I) which yielded yellow blocks.

Refinement
The C-bound H atoms were geometrically placed (C-H = 0.95-0.98 Å) and refined as riding with U iso (H) = 1.2-1.5U eq (C). The N-bound H atom was refined freely.

Computing details
Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).   A view in projection down the a axis of the unit-cell contents of (I). The N-H···Cl and π-π interactions are shown as blue and purple dashed lines, respectively. 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.