Ethane-1,2-diaminium bis­(4-carb­oxy-2-propyl-1H-imidazole-5-carb­oxy­ate) monohydrate

Ying, Y.-M.; Zhang, T.; Yang, G.-R.; Ma, N.

doi:10.1107/S1600536812029406

Volume 68
Part 8
Page o2327
August 2012

Received 14 May 2012
Accepted 28 June 2012
Online 4 July 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R = 0.060
wR = 0.182
Data-to-parameter ratio = 11.9
Details

Ethane-1,2-diaminium bis(4-carboxy-2-propyl-1H-imidazole-5-carboxyate) monohydrate

Yi-Mei Ying,^a Tong Zhang,^b Guang-Rui Yang ^a and Ning Ma ^a ^*

^aInstitute of Environmental and Municipal Engineering, North China University of Water Conservancy and Electric Power, Zhengzhou 450011, People's Republic of China, and ^bHenan Museum, Zhengzhou 450001, People's Republic of China
Correspondence e-mail: hbsymaning@163.com

In the title hydrated molecular salt, C₂H₁₀N₂²⁺·2C₈H₉N₂O₄^-·H₂O, an intramolecular O-HO hydrogen bond occurs in the anion, forming an S(7) ring. The -CO₂ and -CO₂H groups make dihedral angles of 3.2 (2) and 2.0 (3)°, respectively, with the five-membered ring. In the crystal, N-HO, N-HN and O-HO hydrogen bonds lead to the formation of a three-dimensional supramolecular architecture. The methyl group in the anion is disordered over two sets of sites in a 0.716 (9):0.284 (9) ratio. The ethylenediamine cation is generated by symmetry and the water molecule lies on a twofold axis.

Related literature

For background to studies of supramolecular structures of co-crystals containing organic acids and organic bases resulting from hydrogen bonding, see: Wang & Wei (2005).

Experimental

Crystal data

C₂H₁₀N₂²⁺·2C₈H₉N₂O₄^-·H₂O
M_r = 474.48
Monoclinic, C 2/c
a = 15.234 (4) Å
b = 16.859 (4) Å
c = 9.699 (3) Å
= 112.991 (5)°
V = 2293.1 (10) Å³
Z = 4
Mo K radiation
= 0.11 mm^-1
T = 296 K
0.36 × 0.28 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) T_min = 0.961, T_max = 0.983
5444 measured reflections
2011 independent reflections
1500 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.060
wR(F²) = 0.182
S = 1.05
2011 reflections
169 parameters
34 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.30 e Å^-3
_min = -0.45 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2AO4ⁱ	0.86	1.92	2.759 (3)	166
N3-H3AN1	0.89	2.03	2.921 (3)	176
N3-H3AO1	0.89	2.54	2.964 (3)	110
N3-H3BO1ⁱⁱ	0.89	1.94	2.792 (3)	160
N3-H3CO1Wⁱⁱⁱ	0.89	2.08	2.917 (3)	157
O2-H2O3	0.82	1.64	2.457 (3)	177
O1W-H1WO3	0.85 (1)	1.96 (1)	2.795 (2)	169 (4)
Symmetry codes: (i) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y, -z-{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GG2081 ).

Acknowledgements

This work was supported financially by the North China University of Water Conservancy and Electric Power, China.

References

Bruker (2001). SAINT-Plus and SMART. Bruker AXS, Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wang, Z.-L. & Wei, L.-H. (2005). Acta Cryst. E61, o3129-o3130.

organic compounds