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

Mrad, M.L.; Ferretti, V.; Rzaigui, M.; Ben Nasr, C.

doi:10.1107/S160053681204189X

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 (C-C) = 0.003 Å
R = 0.038
wR = 0.101
Data-to-parameter ratio = 13.7
Details

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

Mohamed Lahbib Mrad,^a Valeria Ferretti,^b Mohamed Rzaigui ^a and Cherif Ben Nasr ^a ^*

^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 HPO₄^2- anions, while the second one is built up by H₂PO₄^- anions. Both types of chains are held together by O-HO hydrogen bonds. The organic cations are attached to these chains through N-HO and C-HO hydrogen bonds. The piperazin-1,4-diium ring adopts a chair conformation.

Related literature

For graph-set motifs, see: Bernstein et al. (1995). For reference structural data, see: Kaabi et al. (2004); Chtioui & Jouini (2006); Jensen et al. (2007).

Experimental

Crystal data

C₆H₁₈N₃·HPO₄·H₂PO₄
M_r = 325.20
Monoclinic, P 2₁ /c
a = 12.9417 (2) Å
b = 11.1054 (2) Å
c = 9.3981 (4) Å
= 92.566 (1)°
V = 1349.37 (7) Å³
Z = 4
Mo K radiation
= 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(I)
R_int = 0.016

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.101
S = 1.07
3518 reflections
256 parameters
All H-atom parameters refined
_max = 0.87 e Å^-3
_min = -0.69 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO3	0.93 (2)	1.66 (2)	2.582 (2)	168 (2)
N2-H2naO6	0.91 (2)	1.80 (2)	2.692 (2)	167 (2)
N3-H3naO3	0.87 (3)	1.90 (3)	2.759 (2)	168 (3)
O4-H4oO2ⁱ	0.81 (4)	1.78 (4)	2.582 (2)	170 (3)
N2-H2NBO1ⁱ	0.93 (3)	1.72 (3)	2.656 (2)	175 (3)
N3-H3NBO2ⁱⁱ	0.92 (3)	1.79 (3)	2.683 (2)	164 (2)
N3-H3NCO1ⁱⁱⁱ	0.93 (3)	1.83 (3)	2.747 (2)	171 (2)
O8-H8OO6^iv	0.82 (4)	1.80 (4)	2.614 (2)	173 (4)
O7-H7OO5^v	0.80 (4)	1.74 (4)	2.502 (2)	159 (4)
C3-H3AO1	0.96 (2)	2.58 (2)	3.427 (2)	147 (2)
C5-H5BO5^vi	0.99 (2)	2.44 (2)	3.236 (2)	137 (2)
C2-H2BO4^vii	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); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 1999).

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.
Bernstein, J., Davids, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
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.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
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.
Kaabi, K., Ben Nasr, C. & Lefebvre, F. (2004). Mater. Res. Bull. 39, 205-215.
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.

organic compounds