2-Ammonio-3-(4-nitro­phen­yl)propanoate monohydrate

Dai, W.; Fu, D.-W.

doi:10.1107/S1600536808017960

Volume 64
Part 8
Page o1446
August 2008

Received 31 May 2008
Accepted 12 June 2008
Online 9 July 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.052
wR = 0.141
Data-to-parameter ratio = 8.5
Details

2-Ammonio-3-(4-nitrophenyl)propanoate monohydrate

Wei Dai ^a and Da-Wei Fu ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
Correspondence e-mail: fudavid88@yahoo.com.cn

The title compound, C₉H₁₀N₂O₄·H₂O, exists as a zwitterion with a deprotonated carboxyl group and a protonated amine group. The crystal packing is stabilized by intermolecular N-HO and O-HO hydrogen bonds, building sheets parallel to the (001) plane.

Related literature

For details on [alpha] -amino acids as precursors for the synthesis of novel biologically active compounds, see: Lucchese et al. (2007); Arki et al. (2004); Hauck et al. (2006); Azim et al. (2006).

Experimental

Crystal data

C₉H₁₀N₂O₄·H₂O
M_r = 228.21
Monoclinic, P 2₁
a = 6.2349 (12) Å
b = 5.2990 (11) Å
c = 15.727 (3) Å
= 101.40 (3)°
V = 509.35 (18) Å³
Z = 2
Mo K radiation
= 0.12 mm^-1
T = 293 (2) K
0.30 × 0.25 × 0.15 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T_min = 0.964, T_max = 0.982
5388 measured reflections
1297 independent reflections
1184 reflections with I > 2(I)
R_int = 0.034

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.140
S = 1.14
1297 reflections
153 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.36 e Å^-3
_min = -0.34 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2AO3ⁱ	0.89	2.16	2.745 (4)	123
N2-H2BO4ⁱⁱ	0.89	2.30	2.904 (4)	125
O5-H30O4ⁱⁱⁱ	0.92 (6)	1.81 (6)	2.721 (5)	177 (5)
O5-H31O3^iv	0.79 (8)	2.11 (8)	2.809 (4)	148 (6)
Symmetry codes: (i) x, y-1, z; (ii) $[-x, y-{\script{1\over 2}}, -z+1]$ ; (iii) x+1, y, z; (iv) x+1, y-1, z.

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: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2221 ).

Acknowledgements

This work was supported by a Start-up Grant from Southeast University to Professor Ren-Gen Xiong, and by the Excellent Doctor Degree Foundation from Southeast University to D-WF.

References

Arki, A., Tourwe, D., Solymar, M., Fueloep, F., Armstrong, D. W. & Peter, A. (2004). Chromatographia, 60, S43-S54.
Azim, A., Shah, V. & Doncel, G.-F. (2006). Bioconjugate Chem. 17, 1523-1529.
Hauck, T., Sunkel, K. & Beck, W. (2006). Z. Anorg. Allg. Chem. 632, 2305-2309.
Lucchese, G., Stufano, A. & Trost, B. (2007). Amino Acids, 33, 703-707.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds