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Volume 69 
Part 7 
Pages o1145-o1146  
July 2013  

Received 24 May 2013
Accepted 16 June 2013
Online 22 June 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.055
wR = 0.152
Data-to-parameter ratio = 37.3
Details
Open access

Bis[1-(2,3-dimethylphenyl)piperazine-1,4-diium] bis(oxonium) cyclohexaphosphate dihydrate

aLaboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna Bizerte, Tunisia, and bPetrochemical Research Chair, College of Science, King Saud University, Riyadh, Saudi Arabia
Correspondence e-mail: sonia.abid@fsb.rnu.tn

In the title compound, 2C12H20N22+·2H3O+·P6O186-·2H2O, a protonated water molecule bridges the centrosymmetrical anionic P6O18 ring via O-H...O hydrogen bonds. The centrosymmetric hydrogen-bonded rings formed by four oxonium cations and four phosphate anions can be described by an R48(36) graph-set motif. The ring motifs are connected by hydrogen bonds into inorganic layers perpendicular to [100]. The 1-(2,3-dimethylphenyl)piperazine-1,4-diium cations are located between the layers, compensating their negative charge and establishing N-H...O hydrogen bonds with the O atoms of the anionic framework.

Related literature

For background to the chemistry of cyclohexaphosphate, see: Durif (1995[Durif, A. (1995). In Crystal Chemistry of Condensed Phosphates. New York and London: Plenum Press.]); Amri et al. (2008[Amri, O., Abid, S. & Rzaigui, M. (2008). Phosphorus Sulfur Silicon Relat. Elem. 183, 1996-2005.]); Marouani et al. (2010[Marouani, H., Rzaigui, M. & Al-Deyab, S. S. (2010). Acta Cryst. E66, o2613.]). For applications of piperazine derivatives, see: Kaur et al. (2010[Kaur, K., Jain, M., Reddy, R. P. & Jain, R. (2010). Eur. J. Med. Chem. 45, 3245-3264.]); Eswaran et al. (2010[Eswaran, S., Adhikari, A. V., Chowdhury, I. H., Pal, N. K. & Thomas, K. D. (2010). Eur. J. Med. Chem. 45, 3374-3383.]); Chou et al. (2010[Chou, L. C., Tsai, M. T., Hsu, M. H., Wang, S. H., Way, T. D., Huang, C. H., Lin, H. Y., Qian, K., Dong, Y., Lee, K. H., Huang, L. J. & Kuo, S. C. (2010). J. Med. Chem. 53, 8047-8058.]); Chen et al. (2004[Chen, Y. L., Hung, H. M., Lu, C. M., Li, K. C. & Tzeng, C. C. (2004). Bioorg. Med. Chem. 12, 6539-6546.]); Shingalapur et al. (2009[Shingalapur, R. V., Hosamani, K. M. & Keri, R. S. (2009). Eur. J. Med. Chem. 44, 4244-4248.]). For related structures with cyclohexaphosphate rings, see: Abid et al. (2011[Abid, S., Al-Deyab, S. S. & Rzaigui, M. (2011). Acta Cryst. E67, m1549-m1550.]); Ameur et al. (2013[Ameur, I., Abid, S., Al-Deyab, S. S. & Rzaigui, M. (2013). Acta Cryst. E69, m305-m306.]); Amri et al. (2009[Amri, O., Abid, S. & Rzaigui, M. (2009). Acta Cryst. E65, o654.]). For related structures with 1-phenylpiperazine-1,4-diium salts, see: Marouani et al. (2010[Marouani, H., Rzaigui, M. & Al-Deyab, S. S. (2010). Acta Cryst. E66, o2613.]); Ben Gharbia et al. (2005[Ben Gharbia, I., Kefi, R., Rayes, A. & Ben Nasr, C. (2005). Z. Kristallogr. 220, 333-334.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995[Bernstein, J., David, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For the synthesis of the precursor, see: Schülke & Kayser (1985[Schülke, U. & Kayser, R. (1985). Z. Anorg. Allg. Chem. 531, 167-175.]).

[Scheme 1]

Experimental

Crystal data
  • 2C12H20N22+·2H3O+·P6O186-·2H2O

  • Mr = 932.50

  • Monoclinic, P 21 /c

  • a = 8.630 (6) Å

  • b = 14.495 (4) Å

  • c = 17.072 (3) Å

  • [beta] = 114.93 (4)°

  • V = 1936.6 (15) Å3

  • Z = 2

  • Ag K[alpha] radiation

  • [lambda] = 0.56085 Å

  • [mu] = 0.20 mm-1

  • T = 293 K

  • 0.60 × 0.40 × 0.10 mm

Data collection
  • Nonius MACH-3 diffractometer

  • Absorption correction: refined from [Delta]F (Walker & Stuart, 1983[Walker, N. & Stuart, D. (1983). Acta Cryst. A39, 158-166.]) Tmin = 0.892, Tmax = 0.981

  • 12060 measured reflections

  • 9442 independent reflections

  • 5475 reflections with I > 2[sigma](I)

  • Rint = 0.031

  • 2 standard reflections every 120 min intensity decay: none

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.152

  • S = 0.99

  • 9442 reflections

  • 253 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.87 e Å-3

  • [Delta][rho]min = -0.67 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
OW1-H1W1...O9 0.79 1.84 2.614 (3) 166
OW1-H2W1...O2i 0.86 1.97 2.781 (3) 159
OW2-H1W2...O8 0.82 1.69 2.487 (2) 167
OW2-H2W2...OW1ii 0.80 1.77 2.503 (3) 152
OW2-H3W2...O6iii 0.85 1.64 2.481 (2) 178
N1-H1...O1 0.91 1.82 2.690 (2) 160
N2-H2A...O5iv 0.90 1.87 2.714 (2) 156
N2-H2B...O2v 0.90 2.10 2.858 (3) 142
N2-H2B...O5v 0.90 2.28 2.916 (3) 127
Symmetry codes: (i) [x+1, -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+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) -x+1, -y+1, -z; (v) x+1, y, z.

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996[Harms, K. & Wocadlo, S. (1996). XCAD4. University of Marburg, Germany.]); 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: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JJ2168 ).


Acknowledgements

This work was supported by the Tunisian Ministry of H. E. Sc. R. and the Deanship of Scientific Research at King Saud University (research group project No. RGP-VPP-089).

References

Abid, S., Al-Deyab, S. S. & Rzaigui, M. (2011). Acta Cryst. E67, m1549-m1550.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Ameur, I., Abid, S., Al-Deyab, S. S. & Rzaigui, M. (2013). Acta Cryst. E69, m305-m306.  [CrossRef] [ChemPort] [IUCr Journals]
Amri, O., Abid, S. & Rzaigui, M. (2008). Phosphorus Sulfur Silicon Relat. Elem. 183, 1996-2005.  [CSD] [CrossRef]
Amri, O., Abid, S. & Rzaigui, M. (2009). Acta Cryst. E65, o654.  [CSD] [CrossRef] [IUCr Journals]
Ben Gharbia, I., Kefi, R., Rayes, A. & Ben Nasr, C. (2005). Z. Kristallogr. 220, 333-334.
Bernstein, J., David, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Chen, Y. L., Hung, H. M., Lu, C. M., Li, K. C. & Tzeng, C. C. (2004). Bioorg. Med. Chem. 12, 6539-6546.  [CrossRef] [PubMed] [ChemPort]
Chou, L. C., Tsai, M. T., Hsu, M. H., Wang, S. H., Way, T. D., Huang, C. H., Lin, H. Y., Qian, K., Dong, Y., Lee, K. H., Huang, L. J. & Kuo, S. C. (2010). J. Med. Chem. 53, 8047-8058.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Durif, A. (1995). In Crystal Chemistry of Condensed Phosphates. New York and London: Plenum Press.
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Eswaran, S., Adhikari, A. V., Chowdhury, I. H., Pal, N. K. & Thomas, K. D. (2010). Eur. J. Med. Chem. 45, 3374-3383.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Harms, K. & Wocadlo, S. (1996). XCAD4. University of Marburg, Germany.
Kaur, K., Jain, M., Reddy, R. P. & Jain, R. (2010). Eur. J. Med. Chem. 45, 3245-3264.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Marouani, H., Rzaigui, M. & Al-Deyab, S. S. (2010). Acta Cryst. E66, o2613.  [CSD] [CrossRef] [IUCr Journals]
Schülke, U. & Kayser, R. (1985). Z. Anorg. Allg. Chem. 531, 167-175.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Shingalapur, R. V., Hosamani, K. M. & Keri, R. S. (2009). Eur. J. Med. Chem. 44, 4244-4248.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Walker, N. & Stuart, D. (1983). Acta Cryst. A39, 158-166.  [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1145-o1146   [ doi:10.1107/S1600536813016759 ]

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