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Volume 69 
Part 12 
Page o1731  
December 2013  

Received 15 October 2013
Accepted 28 October 2013
Online 6 November 2013

Key indicators
Single-crystal X-ray study
T = 223 K
Mean [sigma](C-C) = 0.002 Å
R = 0.038
wR = 0.096
Data-to-parameter ratio = 10.2
Details
Open access

Ethane-1,2-diaminium 2,2'-[tereph­thal­oyl­bis(aza­nedi­yl)]di­acetate tetrahydrate

aInstitute of Inorganic and Analytical Chemistry, Clausthal University of Technology, Paul-Ernst-Str. 4, D-38678, Clausthal-Zellerfeld, Germany
Correspondence e-mail: arnold.adam@tu-clausthal.de

In the title salt hydrate, C2H10N22+·C12H10N2O62-·4H2O, each of the ions is located about a centre of inversion and the asymmetric unit is completed by two water molecules in general positons. In the crystal, the cations, anions and water mol­ecules are connected by O-H...O and N-H...O hydrogen bonding into a three-dimensional network.

Related literature

The starting material, 2,2'-(benzene-1,4-dicarboxamido)­diacetatic acid, was prepared by the method of Cleaver & Pratt (1955[Cleaver, C. S. & Pratt, B. C. (1955). J. Am. Chem. Soc. 77, 1544-1546.]). For related organic structures, see: Armelin et al. (2001[Armelin, E., Escudero, E., Campos, L. & Puiggalí, J. (2001). Acta Cryst. C57, 172-173.]); Ray et al. (2006[Ray, S., Hegde, R. P., Das, A. K., Shamala, N. & Banerjee, A. (2006). Tetrahedron, 62, 9603-9609.]). For crystal strucutres of d-block elements with 2,2'-(terephthaloylbis(aza­nedi­yl))di­acetate and similar ligands, see: Duan et al. (2010[Duan, J., Zheng, B., Bai, J., Zhang, Q. & Zuo, C. (2010). Inorg. Chim. Acta, 363, 3172-3177.]); Kostakis et al. (2005[Kostakis, G. E., Casella, L., Hadjiliadis, N., Monzani, E., Kourkoumelis, N. & Plakatouras, J. C. (2005). Chem. Commun. 30, 3859-3861.], 2011[Kostakis, G. E., Casella, L., Boudalis, A. K., Monzani, E. & Plakatouras, J. C. (2011). New J. Chem. 35, 1060-1071.]); Wisser et al. (2008[Wisser, B., Chamayou, A.-C., Miller, R., Scherer, W. & Janiak, C. (2008). CrystEngComm, 10, 461-464.]); Zhang & You (2005)[Zhang, H.-T. & You, X.-Z. (2005). Acta Cryst. E61, m1163-m1165.]; Zhang et al. (2006[Zhang, H.-T., Li, Y.-Z., Wang, T.-W., Nfor, E. N., Wang, H.-Q. & You, X.-Z. (2006). Eur. J. Inorg. Chem. pp. 3532-3536.]).

[Scheme 1]

Experimental

Crystal data
  • C2H10N22+·C12H10N2O62-·4H2O

  • Mr = 412.40

  • Monoclinic, P 21 /c

  • a = 7.3710 (11) Å

  • b = 9.0675 (11) Å

  • c = 14.704 (2) Å

  • [beta] = 105.041 (11)°

  • V = 949.1 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 223 K

  • 0.28 × 0.25 × 0.22 mm

Data collection
  • Stoe IPDS 2 diffractometer

  • 9883 measured reflections

  • 1859 independent reflections

  • 1633 reflections with I > 2[sigma](I)

  • Rint = 0.099

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.096

  • S = 1.09

  • 1859 reflections

  • 183 parameters

  • All H-atom parameters refined

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O4-H4B...O3 0.89 (3) 1.80 (3) 2.6792 (16) 169 (2)
N2-H2B...O3 0.96 (2) 1.85 (2) 2.7896 (17) 164.3 (18)
O4-H4A...O1i 0.87 (3) 2.03 (3) 2.8741 (16) 162 (2)
O5-H5A...O2ii 0.92 (3) 1.87 (3) 2.7669 (17) 168 (2)
O5-H5B...O1iii 0.86 (3) 2.01 (3) 2.8641 (17) 169 (3)
N1-H1...O4iv 0.87 (2) 2.02 (2) 2.8509 (17) 159.8 (18)
N2-H2A...O5v 0.93 (2) 1.91 (2) 2.8278 (18) 172.6 (18)
N2-H2C...O2vi 0.93 (2) 1.89 (2) 2.8086 (17) 169 (2)
Symmetry codes: (i) [-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iv) x-1, y, z; (v) -x+2, -y+1, -z+1; (vi) [-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: X-AREA (Stoe, 2008[Stoe (2008). X-AREA. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-AREA; 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: ORTEP-3 for Windows (Farrugia 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2319 ).


References

Armelin, E., Escudero, E., Campos, L. & Puiggalí, J. (2001). Acta Cryst. C57, 172-173.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Cleaver, C. S. & Pratt, B. C. (1955). J. Am. Chem. Soc. 77, 1544-1546.  [CrossRef] [ChemPort] [Web of Science]
Duan, J., Zheng, B., Bai, J., Zhang, Q. & Zuo, C. (2010). Inorg. Chim. Acta, 363, 3172-3177.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Kostakis, G. E., Casella, L., Boudalis, A. K., Monzani, E. & Plakatouras, J. C. (2011). New J. Chem. 35, 1060-1071.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Kostakis, G. E., Casella, L., Hadjiliadis, N., Monzani, E., Kourkoumelis, N. & Plakatouras, J. C. (2005). Chem. Commun. 30, 3859-3861.  [CSD] [CrossRef]
Ray, S., Hegde, R. P., Das, A. K., Shamala, N. & Banerjee, A. (2006). Tetrahedron, 62, 9603-9609.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Stoe (2008). X-AREA. Stoe & Cie, Darmstadt, Germany.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Wisser, B., Chamayou, A.-C., Miller, R., Scherer, W. & Janiak, C. (2008). CrystEngComm, 10, 461-464.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Zhang, H.-T., Li, Y.-Z., Wang, T.-W., Nfor, E. N., Wang, H.-Q. & You, X.-Z. (2006). Eur. J. Inorg. Chem. pp. 3532-3536.  [Web of Science] [CSD] [CrossRef]
Zhang, H.-T. & You, X.-Z. (2005). Acta Cryst. E61, m1163-m1165.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1731  [ doi:10.1107/S1600536813029632 ]

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