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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 [sigma](C-C) = 0.005 Å
R = 0.058
wR = 0.237
Data-to-parameter ratio = 15.3
Details
Open access

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

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-H...O hydrogen bond. In the crystal packing, centrosymmetrically related cations interact through intermolecular O-H...O 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-H...O and N-H...O hydrogen-bonding interactions.

Related literature

For the synthesis of [beta]-amino acids, see: Cohen et al. (2002[ Cohen, J. H., Abdel-Magid, A. F., Almond, H. R. Jr & Maryanoff, C. A. (2002). Tetrahedron Lett. 43, 1977-1981.]); Qu et al. (2004[ 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.]); Zhao (2007[ Zhao, H. (2007). Acta Cryst. E63, o3400.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[ Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]); Etter et al. (1990[ Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]).

[Scheme 1]

Experimental

Crystal data
  • C9H11N2O4+·ClO4-

  • Mr = 310.65

  • Triclinic, [P \overline 1]

  • a = 7.5932 (8) Å

  • b = 7.8843 (1) Å

  • c = 11.8615 (6) Å

  • [alpha] = 94.745 (3)°

  • [beta] = 99.780 (7)°

  • [gamma] = 116.323 (4)°

  • V = 617.11 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[ Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.884, Tmax = 0.950

  • 6395 measured reflections

  • 2799 independent reflections

  • 1732 reflections with I > 2[sigma](I)

  • Rint = 0.049

Refinement
  • R[F2 > 2[sigma](F2)] = 0.058

  • wR(F2) = 0.237

  • S = 0.99

  • 2799 reflections

  • 183 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.58 e Å-3

  • [Delta][rho]min = -0.53 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2A...O4 0.89 2.36 2.953 (4) 124
N2-H2A...O8 0.89 2.15 2.884 (5) 139
N2-H2B...O5i 0.89 2.31 3.113 (5) 150
N2-H2B...O6i 0.89 2.34 3.120 (5) 147
N2-H2C...O2ii 0.89 2.15 2.960 (5) 152
O3-H3...O4iii 0.82 1.89 2.690 (4) 167
C2-H2...O8iv 0.93 2.58 3.420 (5) 150
C6-H6...O2ii 0.93 2.54 3.445 (5) 163
C8-H8A...O6iv 0.97 2.50 3.403 (5) 154
C8-H8B...O7v 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[ Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[ Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[ Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[ Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: PRPKAPPA (Ferguson, 1999[ Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada.]).


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.  [CrossRef] [ChemPort] [ISI]
Cohen, J. H., Abdel-Magid, A. F., Almond, H. R. Jr & Maryanoff, C. A. (2002). Tetrahedron Lett. 43, 1977-1981.  [ISI] [CrossRef] [ChemPort]
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
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.  [CrossRef] [details]
Zhao, H. (2007). Acta Cryst. E63, o3400.  [CSD] [CrossRef] [details]


Acta Cryst (2010). E66, o117  [ doi:10.1107/S1600536809051319 ]

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