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Volume 68 
Part 11 
Page o3120  
November 2012  

Received 25 September 2012
Accepted 6 October 2012
Online 13 October 2012

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.038
wR = 0.101
Data-to-parameter ratio = 13.7
Details
Open access

1-(2-Ammonioethyl)piperazin-1,4-diium dihydrogenophosphate monohydrogenophosphate

aLaboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna, Tunisie, and bChemistry Department and Centro di Strutturistica Diffrattometrica, University of Ferrara, Via L Borsari 46, I-44121 Ferrara, Italy.
Correspondence e-mail: cherif_bennasr@yahoo.fr

The structure of the title compound, C6H18N3·HPO4·H2PO4, is characterized by two kinds of inorganic chains running along the a-axis direction. The first one is composed of HPO42- anions, while the second one is built up by H2PO4- anions. Both types of chains are held together by O-H...O hydrogen bonds. The organic cations are attached to these chains through N-H...O and C-H...O hydrogen bonds. The piperazin-1,4-diium ring adopts a chair conformation.

Related literature

For graph-set motifs, see: Bernstein et al. (1995[Bernstein, J., Davids, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For reference structural data, see: Kaabi et al. (2004[Kaabi, K., Ben Nasr, C. & Lefebvre, F. (2004). Mater. Res. Bull. 39, 205-215.]); Chtioui & Jouini (2006[Chtioui, A. & Jouini, A. (2006). Mater. Res. Bull. 41, 569-575.]); Jensen et al. (2007[Jensen, T. R., Jorgensen, J.-E., Hazell, R. G., Jakobsen, H. J., Chevallier, M.-A., Jorgensen, L. & Wiedermann, A. (2007). Solid State Sci. 9, 72-81.]).

[Scheme 1]

Experimental

Crystal data
  • C6H18N3·HPO4·H2PO4

  • Mr = 325.20

  • Monoclinic, P 21 /c

  • a = 12.9417 (2) Å

  • b = 11.1054 (2) Å

  • c = 9.3981 (4) Å

  • [beta] = 92.566 (1)°

  • V = 1349.37 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.36 mm-1

  • T = 295 K

  • 0.52 × 0.49 × 0.20 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 6163 measured reflections

  • 3518 independent reflections

  • 3167 reflections with I > 2[sigma](I)

  • Rint = 0.016

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

  • wR(F2) = 0.101

  • S = 1.07

  • 3518 reflections

  • 256 parameters

  • All H-atom parameters refined

  • [Delta][rho]max = 0.87 e Å-3

  • [Delta][rho]min = -0.69 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O3 0.93 (2) 1.66 (2) 2.582 (2) 168 (2)
N2-H2na...O6 0.91 (2) 1.80 (2) 2.692 (2) 167 (2)
N3-H3na...O3 0.87 (3) 1.90 (3) 2.759 (2) 168 (3)
O4-H4o...O2i 0.81 (4) 1.78 (4) 2.582 (2) 170 (3)
N2-H2NB...O1i 0.93 (3) 1.72 (3) 2.656 (2) 175 (3)
N3-H3NB...O2ii 0.92 (3) 1.79 (3) 2.683 (2) 164 (2)
N3-H3NC...O1iii 0.93 (3) 1.83 (3) 2.747 (2) 171 (2)
O8-H8O...O6iv 0.82 (4) 1.80 (4) 2.614 (2) 173 (4)
O7-H7O...O5v 0.80 (4) 1.74 (4) 2.502 (2) 159 (4)
C3-H3A...O1 0.96 (2) 2.58 (2) 3.427 (2) 147 (2)
C5-H5B...O5vi 0.99 (2) 2.44 (2) 3.236 (2) 137 (2)
C2-H2B...O4vii 0.96 (3) 2.45 (3) 3.345 (2) 154 (2)
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [-x+2, 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-1; (v) [x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]; (vi) [x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]; (vii) [-x+2, y-{\script{1\over 2}}, -z-{\script{1\over 2}}].

Data collection: KappaCCD Server Software (Nonius, 1997[Nonius (1997). KappaCCD Server Software. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895,Oak Ridge National Laboratory,Oak Ridge, Tennessee, USA.]); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RU2043 ).


Acknowledgements

We would like to acknowledge the support provided by the Secretary of State for Scientific Research and Technology of Tunisia.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Bernstein, J., Davids, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895,Oak Ridge National Laboratory,Oak Ridge, Tennessee, USA.
Chtioui, A. & Jouini, A. (2006). Mater. Res. Bull. 41, 569-575.  [ISI] [CSD] [CrossRef] [ChemPort]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Jensen, T. R., Jorgensen, J.-E., Hazell, R. G., Jakobsen, H. J., Chevallier, M.-A., Jorgensen, L. & Wiedermann, A. (2007). Solid State Sci. 9, 72-81.  [ISI] [CSD] [CrossRef] [ChemPort]
Kaabi, K., Ben Nasr, C. & Lefebvre, F. (2004). Mater. Res. Bull. 39, 205-215.  [ISI] [CSD] [CrossRef] [ChemPort]
Nonius (1997). KappaCCD Server Software. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3120  [ doi:10.1107/S160053681204189X ]

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