N-(2-Benzoylethyl)propan-2-aminium chloride

In the title salt, C12H18NO+·Cl−, N—H⋯Cl interactions between the free chloride anions and the organic cations connect the molecules into hydrogen-bond dimers, forming a R 2 2(8) motif. The dimers are linked by C—H⋯O hydrogen bonds into chains extending along [301]. The carbonyl group is co-planar with the phenyl ring [C—C—C=O torsion angle = −3.3 (7)°]. The side chain has an E conformation.

In the title salt, C 12 H 18 NO + ÁCl À , N-HÁ Á ÁCl interactions between the free chloride anions and the organic cations connect the molecules into hydrogen-bond dimers, forming a R 2 2 (8) motif. The dimers are linked by C-HÁ Á ÁO hydrogen bonds into chains extending along [301]. The carbonyl group is co-planar with the phenyl ring [C-C-C O torsion angle = À3.3 (7) ]. The side chain has an E conformation.
The geometric parameters of the title salt (I) in Fig. 1 are within the range of expected values for this type of compound (Allen et al.,1987;Abonia et al., 2011;Tuzina et al., 2006).

Experimental
A mixture of the appropriate ketone (50 mmol), paraformaldehyde (50 mmol), and isopropylamine hydrochloride (27 mmol) was heated in an oil bath at 403 K. The reaction vessel was then removed from the oil bath and when the temperature of the mixture dropped to 338 K, ethyl acetate (40-80 ml) was added. The mixture was stirred at room temperature for 24 h and the resultant precipitate was collected and recrystallized from ether/methanol. The melting point was 445-447 K (lit. Plati et al., 1949 m.p. 447-449 K) and the yield was 55% (Mete et al., 2011b).

Figure 1
View of the title molecule with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.

Figure 2
The packing and hydrogen bonding of (I) viewed down the b axis. H atoms not involved in hydrogen bondings are omitted for the sake of clarity. Special details Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles Refinement. Refinement on F 2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F 2 > σ(F 2 ) is used only for calculating -R-factor-obs 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.