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Volume 68 
Part 1 
Page o223  
January 2012  

Received 4 December 2011
Accepted 19 December 2011
Online 23 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.006 Å
R = 0.066
wR = 0.176
Data-to-parameter ratio = 15.7
Details
Open access

Ethane-1,2-diaminium (R)-2-[4-(1-carboxylatoethoxy)phenoxy]acetate

aEngineering Research Center of Pesticides of Heilongjiang University, Heilongjiang University, Harbin 150050, People's Republic of China, and College of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China
Correspondence e-mail: hgf1000@163.com

In the title compound, C2H10N22+·C11H10O62-, the two acetate groups of the cation form dihedral angles of 74.2 (4) and 63.9 (5)° with the central benzene ring. In the crystal, N-H...O hydrogen bonds link the cations and anions into layers parallel to the ab plane.

Related literature

For the synthesis of the title chiral carboxylic acid, see: Bezwada et al. (2007[Bezwada, R. S. (2007). US Patent 2007/0141113 A1.]). For the structure of a similar achiral carboxylic acid, see: Gong et al. (2010[Gong, Y.-N., Liu, C.-B., Ding, Y., Xiong, Z.-Q. & Xiong, L. M. (2010). J. Coord. Chem. 63, 1865-1872.]).

[Scheme 1]

Experimental

Crystal data
  • C2H10N22+·C11H10O62-

  • Mr = 300.31

  • Monoclinic, P 21

  • a = 10.066 (2) Å

  • b = 6.7887 (14) Å

  • c = 11.050 (2) Å

  • [beta] = 99.30 (3)°

  • V = 745.2 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 293 K

  • 0.62 × 0.10 × 0.06 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.937, Tmax = 0.994

  • 7250 measured reflections

  • 3288 independent reflections

  • 1855 reflections with I > 2[sigma](I)

  • Rint = 0.066

Refinement
  • R[F2 > 2[sigma](F2)] = 0.066

  • wR(F2) = 0.176

  • S = 1.01

  • 3288 reflections

  • 209 parameters

  • 7 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H33...O2i 0.90 (1) 1.86 (2) 2.736 (5) 164 (4)
N1-H32...O3 0.91 (1) 1.88 (1) 2.784 (5) 174 (5)
N1-H31...O3ii 0.90 (1) 1.94 (3) 2.764 (5) 150 (5)
N2-H34...O5 0.90 (1) 1.86 (2) 2.736 (5) 166 (5)
N2-H35...O5iii 0.90 (1) 1.94 (3) 2.748 (5) 148 (5)
N2-H36...O6iv 0.90 (1) 1.84 (1) 2.736 (5) 172 (5)
Symmetry codes: (i) x, y-1, z; (ii) [-x, y-{\script{1\over 2}}, -z]; (iii) [-x+1, y-{\script{1\over 2}}, -z]; (iv) [-x+1, y+{\script{1\over 2}}, -z].

Data collection: RAPID-AUTO (Rigaku, 1998[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); 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: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5213 ).


Acknowledgements

The authors thank the Project of Innovation Service Platform of Heilongjiang Province (PG09J001) and Heilongjiang University for supporting this work.

References

Bezwada, R. S. (2007). US Patent 2007/0141113 A1.
Gong, Y.-N., Liu, C.-B., Ding, Y., Xiong, Z.-Q. & Xiong, L. M. (2010). J. Coord. Chem. 63, 1865-1872.  [CrossRef] [ChemPort]
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o223  [ doi:10.1107/S1600536811054535 ]

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