2-Carb­oxy-1-(3-nitro­phen­yl)ethanaminium perchlorate

Liang, W.-X.; Li, Y.; Wang, G.; Qu, Z.-R.

doi:10.1107/S1600536809051319

Volume 66
Part 1
Page o117
January 2010

Received 25 November 2009
Accepted 28 November 2009
Online 12 December 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.058
wR = 0.237
Data-to-parameter ratio = 15.3
Details

2-Carboxy-1-(3-nitrophenyl)ethanaminium perchlorate

Wen-Xian Liang,^a Yan Li,^a Gang Wang ^a and Zhi-Rong Qu ^a ^*

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

In the cation of the title compound, C₉H₁₁N₂O₄⁺·ClO₄^-, the conformation is stabilized by an intramolecular N-HO hydrogen bond. In the crystal packing, centrosymmetrically related cations interact through intermolecular O-HO hydrogen bonds involving the carboxy groups, forming dimers. The dimers and the perchlorate anions are further linked into layers parallel to the ab plane by C-HO and N-HO hydrogen-bonding interactions.

Related literature

For the synthesis of [beta] -amino acids, see: Cohen et al. (2002); Qu et al. (2004); Zhao (2007). For hydrogen-bond motifs, see: Bernstein et al. (1995); Etter et al. (1990).

Experimental

Crystal data

C₉H₁₁N₂O₄⁺·ClO₄^-
M_r = 310.65
Triclinic, $[P \overline 1]$
a = 7.5932 (8) Å
b = 7.8843 (1) Å
c = 11.8615 (6) Å
= 94.745 (3)°
= 99.780 (7)°
= 116.323 (4)°
V = 617.11 (7) Å³
Z = 2
Mo K radiation
= 0.35 mm^-1
T = 293 K
0.45 × 0.30 × 0.15 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T_min = 0.884, T_max = 0.950
6395 measured reflections
2799 independent reflections
1732 reflections with I > 2(I)
R_int = 0.049

Refinement

R[F² > 2(F²)] = 0.058
wR(F²) = 0.237
S = 0.99
2799 reflections
183 parameters
H-atom parameters constrained
_max = 0.58 e Å^-3
_min = -0.53 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2AO4	0.89	2.36	2.953 (4)	124
N2-H2AO8	0.89	2.15	2.884 (5)	139
N2-H2BO5ⁱ	0.89	2.31	3.113 (5)	150
N2-H2BO6ⁱ	0.89	2.34	3.120 (5)	147
N2-H2CO2ⁱⁱ	0.89	2.15	2.960 (5)	152
O3-H3O4ⁱⁱⁱ	0.82	1.89	2.690 (4)	167
C2-H2O8^iv	0.93	2.58	3.420 (5)	150
C6-H6O2ⁱⁱ	0.93	2.54	3.445 (5)	163
C8-H8AO6^iv	0.97	2.50	3.403 (5)	154
C8-H8BO7^v	0.97	2.57	3.134 (6)	117
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x-1, y-1, z; (iii) -x, -y+1, -z+1; (iv) -x+1, -y+1, -z+1; (v) -x, -y, -z+1.

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: PRPKAPPA (Ferguson, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2399 ).

Acknowledgements

This work was supported by the Technical Fund Financing Projects (No. 9207042464 and 9207041482) from Southeast University to ZRQ.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Cohen, J. H., Abdel-Magid, A. F., Almond, H. R. Jr & Maryanoff, C. A. (2002). Tetrahedron Lett. 43, 1977-1981.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada.
Qu, Z.-R., Zhao, H., Wang, Y.-P., Wang, X.-S., Ye, Q., Li, Y.-H., Xiong, R.-G., Abrahams, B. F., Liu, Z.-G. & Xue, Z.-L. (2004). Chem. Eur. J. 10, 54-60.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Zhao, H. (2007). Acta Cryst. E63, o3400.

organic compounds