2-Carb­oxy-1-phenyl­ethanaminium perchlorate

Xiu-Zhi Li; Hui Li; Zhi-Rong Qu

doi:10.1107/S1600536809016171

. 2009 May 7;65(Pt 6):o1214. doi: 10.1107/S1600536809016171

2-Carboxy-1-phenylethanaminium perchlorate

Xiu-Zhi Li ^a, Hui Li ^a, Zhi-Rong Qu ^a,^*

PMCID: PMC2969710 PMID: 21583083

Abstract

In the title compound, C₉H₁₂NO₂ ⁺·ClO₄ ⁻, an intramolecular N—H⋯O interaction results in the formation of a six-membered ring having a twisted chair conformation. In the crystal structure, intermolecular O—H⋯O, N—H⋯O and C—H⋯O interactions link the molecules into a network. A weak C—H⋯π interaction is also found.

Related literature

There has been an increased interest in the enantiomeric preparation of β-amino acids as precursors for the synthesis of novel biologically active compounds, see: Arki et al. (2004 ▶); Cohen et al. (2002 ▶); Zeller et al. (1965 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₉H₁₂NO₂ ⁺·ClO₄ ⁻
M _r = 265.65
Orthorhombic,
a = 6.6583 (13) Å
b = 13.826 (3) Å
c = 24.300 (5) Å
V = 2237.0 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 294 K
0.45 × 0.35 × 0.12 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (Blessing, 1995 ▶) T _min = 0.863, T _max = 0.957
21012 measured reflections
2560 independent reflections
1966 reflections with I > 2σ(I)
R _int = 0.058

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.110
S = 1.10
2560 reflections
156 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809016171/hk2675sup1.cif

e-65-o1214-sup1.cif^{(15.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016171/hk2675Isup2.hkl

e-65-o1214-Isup2.hkl^{(125.8KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O2	0.89	2.13	2.773 (3)	128
C9—H9⋯O5ⁱ	0.93	2.56	3.409 (3)	152
C3—H3⋯O5ⁱ	0.98	2.57	3.370 (3)	139
C3—H3⋯O2ⁱⁱ	0.98	2.58	3.286 (3)	129
N1—H1C⋯O3ⁱⁱⁱ	0.89	2.05	2.892 (3)	158
N1—H1B⋯O3^iv	0.89	2.28	3.046 (3)	144
N1—H1A⋯O6^v	0.89	2.13	2.979 (3)	159
O1—H1⋯O2^vi	0.82	2.41	3.046 (2)	135
O1—H1⋯O4^vii	0.82	2.35	3.048 (3)	143
C8—H8⋯Cg1^viii	0.93	2.79	3.688 (3)	162

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) . Cg1 is the centroid of the C4–C9 ring.

Acknowledgments

This work was supported by the Technical Fund Financing Projects (grant Nos. 9207042464 and 9207041482) from Southeast University to ZRQ.

supplementary crystallographic information

Comment

β-Amino acids are important molecules, due to their pharmacological properties. Recently, there has been an increased interest in the enantiomeric preparations of β-amino acids, as precursors for the synthesis of novel biologically active compounds (Arki et al., 2004; Cohen et al., 2002; Zeller et al., 1965). We report herein the crystal structure of the title compound.

The asymmetric unit of the title compound contains one cation and one anion (Fig.1 ), in which the bond lengths (Allen et al., 1987) and angles are within normal ranges. Ring A (C4-C9) is, of course, planar. Intramolecular N-H···O interaction results in the formation of a six-membered ring B (O2/N1/C1-C3/H1B) having twisted conformation.

In the crystal structure, intermolecular O-H···O, N-H···O and C-H···O interactions (Table 1) link the molecules into a network (Fig. 2), in which they may be effective in the stabilization of the structure. There also exists a weak C—H···π interaction (Table 1).

Experimental

Under nitrogen protection, benzaldehyde (3.18 g, 30 mmol), malonic acid (5.00 g, 48 mmol) and ammonium acetate (6.00 g, 78 mmol) were added into a flask and refluxed for 10 h to yield a colorless precipitate. The crude product was obtained after filtration, then it was dissolved in ethanol/ perchloric acid (1:1), after slowly evaporating over a period of 4 d, colorless prism crystals of the title compound suitable for X-ray analysis were isolated.