N-[ ( S )-1-Phenylethyl ] carbamoyl } methylaminium chloride

All the geometrical parameters for (I) lie within their expected ranges (Allen et al., 1995). The absolute configuration of (I) is well defined and atom C7 has S configuration, as expected from the configuration of the equivalent C atom in the (S)-1-phenylethylamine starting material. The dihedral angle between the mean planes of the benzene ring (atoms C1–C6) and the C7/C9/C10/N1/O1 grouping is 66.14 (13) . The crystal packing in (I) is influenced by hydrogen bonds (Table 1). An N—H O bond arising from the N1 group links the cations into chains propagating in the a direction. The –NH3 group participates in three N—H Cl bonds [mean H Cl = 2.32 Å, mean N Cl = 3.183 (3) Å, mean N— H Cl = 159 ], which crosslink the [100] stacks in the b direction. The only intermolecular interactions in the c Received 24 August 2005 Accepted 26 August 2005 Online 7 September 2005

In the title compound, C 10 H 15 N 2 O + ÁCl À , the crystal packing is influenced by N-HÁ Á ÁO and N-HÁ Á ÁCl hydrogen bonds, resulting in a layered structure.

Comment
The known title compound, (I) (Fig. 1), was prepared as an intermediate in the syntheses of new asymmetric catalysts, following the literature procedure of Ho et al. (2001).
All the geometrical parameters for (I) lie within their expected ranges (Allen et al., 1995). The absolute configuration of (I) is well defined and atom C7 has S configuration, as expected from the configuration of the equivalent C atom in the (S)-1-phenylethylamine starting material. The dihedral angle between the mean planes of the benzene ring (atoms C1-C6) and the C7/C9/C10/N1/O1 grouping is 66.14 (13) .
The crystal packing in (I) is influenced by hydrogen bonds (Table 1). An N-HÁ Á ÁO bond arising from the N1 group links the cations into chains propagating in the a direction. The -NH 3 group participates in three N-HÁ Á ÁCl bonds [mean HÁ Á ÁCl = 2.32 Å , mean NÁ Á ÁCl = 3.183 (3) Å , mean N-HÁ Á ÁCl = 159 ], which crosslink the [100] stacks in the b direction. The only intermolecular interactions in the c direction are van der Waals forces (Fig. 2). A PLATON (Spek, 2003) analysis of (I) flagged a short intramolecular C-HÁ Á ÁO distance ( Fig. 1 and Table 1), although its structural significance -an attractive interaction or a repulsive steric contactis not clear.

Experimental
N-Boc glycine (10 mmol, 1.75 g) was dissolved in dry THF (30 ml) in a dry flask under nitrogen. The solution was cooled to 195 K, and Nmethyl morpholine (10 mmol, 1.01 g, 1.09 ml) was added with stirring.
i Bu-chloroformate (10 mmol, 1.36 g, 1.30 ml) was added, and the solution stirred for 30 min. (S)-1-Phenylethylamine (10 mmol, 1.21 g, 1.29 ml) was added in one portion and the reaction mixture stirred at room temperature for 18 h. The solvent was removed in vacuo. The residue was taken up in EtOAc (30 ml), washed with 10% aqueous Na 2 CO 3 (20 ml), 0.1 M aqueous HCl (20 ml) and saturated brine (20 ml), then dried over Na 2 SO 4 and filtered, and the solvent was removed in vacuo. The resulting oil (1.37 g, 4.95 mmol) was dissolved in dry dichloromethane (DCM, 15 ml) and cooled to 273 K. Bubbling excess dry HCl through the reaction medium with stirring for 2 h allowed the collection of the desired product as a white precipitate, which was recrystallized from EtOH/Et 2 O (1.09 g, 89%). Slow evaporation of a DCM solution of the purified material produced colourless needles of (I) suitable for diffraction; m.p.

D-HÁ
All H atoms were placed in calculated positions (C-H = 0.95-0.99 Å and N-H = 0.88-0.91 Å ) and refined as riding on their carrier atoms, allowing for rotation of the rigid terminal -XH 3 groups. The constraint U iso (H) = 1.2U eq (carrier) or U iso (H) = 1.5U eq (methyl carrier) was applied as applicable.
The crystal packing in (I) is influenced by hydrogen bonds (Table 1). An N-H···O bond arising from the N1 group links the molecules into chains propagating in the a direction. The -NH 3 group participates in three N-H···Cl bonds [mean H···Cl = 2.32 Å, mean N···Cl = 3.183 (3) Å, mean N-H···Cl = 159°], which crosslink the [100] stacks in the b direction. The only intermolecular interactions in the c direction are van der Waals forces (Fig. 2). A PLATON (Spek, 2003) analysis of (I) flagged a short intramolecular C-H···O distance ( Fig. 1 and Table 1), although its structural significance -an attractive interaction or a repulsive steric contact -is not clear.

S2. Experimental
N-Boc glycine (10 mmol, 1.75 g) was dissolved in dry THF (30 ml) in a dry flask under nitrogen. The solution was cooled to 195 K, and N-methyl morpholine (10 mmol, 1.01 g, 1.09 ml) was added with stirring. iBu-chloroformate (10 mmol, 1.36 g, 1.30 ml) was added, and the solution stirred for 30 min. (S)-1-Phenylethylamine (10 mmol, 1.21 g, 1.29 ml) was added in one portion and the reaction stirred at room temperature for 18 h. The solvent was removed in vacuo.
The residue was taken up in EtOAc (30 ml), washed with 10% aqueous Na 2 CO 3 (20 ml), 0.1 M aqueous HCl (20 ml) and saturated brine (20 ml), then dried over Na 2 SO 4 and filtered, and the solvent was removed in vacuo. The resulting oil (1.37 g, 4.95 mmol) was dissolved in dry DCM (15 ml) and cooled to 273 K. Bubbling excess dry HCl through the reaction medium with stirring for 2 h allowed the collection of the desired product as a white precipitate, which was

Figure 1
View of (I) (50% probability displacement ellipsoids; H atoms are drawn as small spheres of arbitrary radii). The N-H···Cl hydrogen bond and possible C-H···O interaction are indicated by dashed lines.   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.