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

Ren, C.-Y.; Hou, G.-F.; Yu, Y.-H.; Gao, J.-S.

doi:10.1107/S1600536811054535

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 (C-C) = 0.006 Å
R = 0.066
wR = 0.176
Data-to-parameter ratio = 15.7
Details

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

Chang-Yue Ren,^a Guang-Feng Hou,^a Ying-Hui Yu ^a and Jin-Sheng Gao ^a ^*

^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⁺·C₁₁H₁₀O₆^2-, 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-HO 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). For the structure of a similar achiral carboxylic acid, see: Gong et al. (2010).

Experimental

Crystal data

C₂H₁₀N₂²⁺·C₁₁H₁₀O₆^2-
M_r = 300.31
Monoclinic, P 2₁
a = 10.066 (2) Å
b = 6.7887 (14) Å
c = 11.050 (2) Å
= 99.30 (3)°
V = 745.2 (3) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.937, T_max = 0.994
7250 measured reflections
3288 independent reflections
1855 reflections with I > 2(I)
R_int = 0.066

Refinement

R[F² > 2(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
_max = 0.40 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H33O2ⁱ	0.90 (1)	1.86 (2)	2.736 (5)	164 (4)
N1-H32O3	0.91 (1)	1.88 (1)	2.784 (5)	174 (5)
N1-H31O3ⁱⁱ	0.90 (1)	1.94 (3)	2.764 (5)	150 (5)
N2-H34O5	0.90 (1)	1.86 (2)	2.736 (5)	166 (5)
N2-H35O5ⁱⁱⁱ	0.90 (1)	1.94 (3)	2.748 (5)	148 (5)
N2-H36O6^iv	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); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002); 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: 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.
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.

organic compounds