1-Meth­oxycarbonyl-2-(4-nitro­phen­yl)ethanaminium nitrate

Xiao-Chun Wen

doi:10.1107/S1600536808028390

. 2008 Sep 13;64(Pt 10):o1905. doi: 10.1107/S1600536808028390

1-Methoxycarbonyl-2-(4-nitrophenyl)ethanaminium nitrate

Xiao-Chun Wen ^a,^*

PMCID: PMC2959357 PMID: 21201115

Abstract

In the title compound, C₁₀H₁₃O₄N₂ ⁺·NO₃ ⁻, the nitro group and the benzene ring are essentially coplanar. The dihedral angle between the benzene ring and the methylcarboxylate plane is 49.6 (3)°. The crystal structure is stabilized by cation–anion N—H⋯O and N—H⋯N hydrogen bonds, building sheets parallel to (001).

Related literature

For details of α-amino acid derivatives, see: Lucchese et al. (2007 ▶); Arki et al. (2004 ▶); Hauck et al. (2006 ▶); Dai & Fu (2008 ▶); Wen (2008 ▶); Azim et al. (2006 ▶).

Experimental

Crystal data

C₁₀H₁₃N₂O₄ ⁺·NO₃ ⁻
M _r = 287.23
Monoclinic,
a = 5.3722 (11) Å
b = 8.4244 (17) Å
c = 15.380 (3) Å
β = 93.67 (3)°
V = 694.6 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 298 (2) K
0.25 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.94, T _max = 0.96
7232 measured reflections
1682 independent reflections
1164 reflections with I > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.160
S = 1.04
1682 reflections
181 parameters
7 restraints
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Data collection: CrystalClear (Rigaku, 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808028390/ci2667sup1.cif

e-64-o1905-sup1.cif^{(16.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808028390/ci2667Isup2.hkl

e-64-o1905-Isup2.hkl^{(82.8KB, 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
N2—H2B⋯O5ⁱ	0.89	1.90	2.771 (4)	166
N2—H2B⋯N3ⁱ	0.89	2.60	3.402 (4)	151
N2—H2B⋯O6ⁱ	0.89	2.61	3.218 (5)	126
N2—H2C⋯O6ⁱⁱ	0.89	2.35	2.950 (5)	124
N2—H2C⋯O3ⁱⁱⁱ	0.89	2.41	2.929 (5)	117
N2—H2C⋯O7ⁱⁱⁱ	0.89	2.47	3.176 (5)	137
N2—H2A⋯O7	0.89	2.12	2.993 (5)	166
N2—H2A⋯O5	0.89	2.26	2.917 (4)	130
N2—H2A⋯N3	0.89	2.56	3.402 (4)	158

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

This work was supported by a start-up grant from Southeast University to Professor Ren-Gen Xiong.

supplementary crystallographic information

Comment

Amino acid derivatives are important compounds due to their biological activities, and there has been an increased interest in the enantiomeric preparation of α-amino acid derivatives as precursors for the synthesis of novel biologically active molecules (Lucchese et al., 2007; Arki et al., 2004; Hauck et al., 2006; Azim et al., 2006; Dai et al., 2008; Wen, 2008). Here we report the crystal structure of the title compound.

The asymmetric unit of the title compound contains a organic cation and a NO₃^- anion (Fig. 1). The nitro group and the benzene ring are essentially coplanar, and the methyl 2-aminopropanoate substituent group is in an extended conformation. The dihedral angle between the C1–C6 and C8–C10/O3/O4 planes is 49.6 (3)°. The S absolute configuration at C8 was deduced from the synthetic pathway.

The crystal packing is stabilized by cation–anion N—H···O and N—H···N hydrogen bonds (Table 1) building sheets parallel to the (001) (Fig. 2).

Experimental

Under nitrogen protection, 2-amino-3-phenylpropanoic acid (30 mmol), nitric acid (50 mmol) and sulfuric acid (20 mmol) were added in a flask. The mixture was stirred at 383 K for 3 h. The resulting solution was poured into ice water (100 ml), then filtered and washed with distilled water. The nitration amino acid was esterified with H₂SO₄ and CH₃OH at 383 K for 12 h. The crude product obtained by evaporation of the solution was recrystallized with distilled water (15 ml)-HNO₃ (1 ml) to yield colourless block-like crystals, suitable for X-ray analysis.