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Volume 70 
Part 1 
Page o61  
January 2014  

Received 5 November 2013
Accepted 8 December 2013
Online 14 December 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.006 Å
R = 0.050
wR = 0.128
Data-to-parameter ratio = 17.8
Details
Open access

Hexa­kis­(3-chloro-2-methyl­anilinium) cyclo­hexa­phosphate dihydrate

aChemistry Laboratory of Materials, Sciences Faculty of Bizerta, 7021 Jarzouna, Bizerta, Tunisia
Correspondence e-mail: Lamia.khederi@fsb.rnu.tn

In the organic/inorganic salt hydrate, 6C7H9ClN+·P6O186-·2H2O, the cyclo­hexa­phosphate anion resides on an inversion centre. The asymmetric unit consists of three cations, one half-anion and a water mol­ecule. In the crystal, the water mol­ecules and the [P6O18]6- anions are linked by O-H...O hydrogen bonds, generating infinite layers parallel to the ab plane. These layers are inter­connected by the organic cations through N-H...O hydrogen bonds.

Related literature

For the properties of hybrid materials, see: Shi et al. (2000[Shi, F. N., Shen, Z., You, X. Z. & Duan, C. Y. (2000). J. Mol. Struct. 523, 143-147.]); Yokotani et al. (1989[Yokotani, A., Sasaki, T., Yoshida, K. & Nakai, S. (1989). Appl. Phys. Lett. 55, 2692-2693.]); Xiao et al. (2005[Xiao, D., An, H., Waag, E. & Xu, L. (2005). J. Mol. Struct. 738, 217-225.]); Koo et al. (2004[Koo, B. K., Ouellette, W., Burkholder, E. M., Golub, V., O'Connor, C. J. & Zubieta, J. (2004). Solid State Sci. 6, 461-468.]). For related structures containing cyclo­hexa­phosphate rings, see: Khedhiri et al. (2012[Khedhiri, L., Akriche, S., Al-Deyab, S. S. & Rzaigui, M. (2012). Acta Cryst. E68, o2038-o2039.]); Amri et al. (2009[Amri, O., Abid, S. & Rzaigui, M. (2009). Acta Cryst. E65, o654.]); Marouani & Rzaigui (2010[Marouani, H. & Rzaigui, M. (2010). Acta Cryst. E66, o233.]); Averbuch-Pouchot & Durif (1991[Averbuch-Pouchot, M. T. & Durif, A. (1991). Eur. J. Solid State Inorg. Chem. 28, 9-22.]). For bond lengths, see: Fábry et al. (2002[Fábry, J., Krupková, R. & Studnicka, V. (2002). Acta Cryst. E58, o105-o107.]). For the preparation of cyclo­hexa­phospho­ric acid, see: Schülke & Kayser (1985[Schülke, U. & Kayser, R. (1985). Z. Anorg. Allg. Chem. 531, 167-175.]).

[Scheme 1]

Experimental

Crystal data
  • 6C7H9ClN+·P6O186-·2H2O

  • Mr = 1365.46

  • Triclinic, [P \overline 1]

  • a = 9.576 (5) Å

  • b = 10.187 (4) Å

  • c = 17.392 (5) Å

  • [alpha] = 94.48 (2)°

  • [beta] = 103.74 (4)°

  • [gamma] = 112.25 (4)°

  • V = 1498.5 (12) Å3

  • Z = 1

  • Mo K[alpha] radiation

  • [mu] = 0.52 mm-1

  • T = 293 K

  • 0.32 × 0.22 × 0.15 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • 7464 measured reflections

  • 7229 independent reflections

  • 4800 reflections with I > 2[sigma](I)

  • Rint = 0.033

  • 2 standard reflections every 120 min intensity decay: 5%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.128

  • S = 1.02

  • 7229 reflections

  • 405 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.39 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O8 0.95 (4) 1.76 (4) 2.705 (4) 179 (5)
N1-H1B...O1Wi 0.97 (4) 1.85 (4) 2.779 (4) 160 (3)
N1-H1C...O4ii 0.94 (4) 1.83 (4) 2.766 (4) 173 (3)
O1W-H1W...O1iii 0.82 (5) 2.02 (6) 2.813 (4) 164 (5)
O1W-H2W...O5ii 0.82 (5) 2.14 (5) 2.934 (4) 163 (5)
N2-H2A...O5 0.90 (4) 2.02 (4) 2.871 (4) 156 (4)
N2-H2B...O2iv 0.93 (5) 1.85 (5) 2.763 (4) 166 (3)
N2-H2C...O1v 0.89 (4) 1.89 (4) 2.775 (4) 176 (4)
N3-H3A...O7iv 1.00 (5) 1.77 (5) 2.759 (4) 171 (5)
N3-H3B...O4ii 1.01 (4) 1.83 (4) 2.834 (4) 172 (4)
N3-H3C...O2iv 0.85 (4) 2.00 (4) 2.827 (4) 166 (3)
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z+1; (iii) x, y-1, z; (iv) x+1, y, z; (v) -x+1, -y+2, -z+1.

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, 1995[Harms, K. & Wocadlo, S. (1995). 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: FJ2652 ).


References

Amri, O., Abid, S. & Rzaigui, M. (2009). Acta Cryst. E65, o654.  [CSD] [CrossRef] [IUCr Journals]
Averbuch-Pouchot, M. T. & Durif, A. (1991). Eur. J. Solid State Inorg. Chem. 28, 9-22.  [ChemPort]
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Fábry, J., Krupková, R. & Studnicka, V. (2002). Acta Cryst. E58, o105-o107.  [CSD] [CrossRef] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Khedhiri, L., Akriche, S., Al-Deyab, S. S. & Rzaigui, M. (2012). Acta Cryst. E68, o2038-o2039.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Koo, B. K., Ouellette, W., Burkholder, E. M., Golub, V., O'Connor, C. J. & Zubieta, J. (2004). Solid State Sci. 6, 461-468.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Marouani, H. & Rzaigui, M. (2010). Acta Cryst. E66, o233.  [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]
Shi, F. N., Shen, Z., You, X. Z. & Duan, C. Y. (2000). J. Mol. Struct. 523, 143-147.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Xiao, D., An, H., Waag, E. & Xu, L. (2005). J. Mol. Struct. 738, 217-225.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Yokotani, A., Sasaki, T., Yoshida, K. & Nakai, S. (1989). Appl. Phys. Lett. 55, 2692-2693.  [CrossRef] [ChemPort] [Web of Science]


Acta Cryst (2014). E70, o61  [ doi:10.1107/S1600536813033230 ]

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