Related literature   {#sec1}
====================

For background to the chemistry of cyclo­hexa­phosphate, see: Durif (1995[@bb10]); Amri *et al.* (2008[@bb3]); Marouani *et al.* (2010[@bb16]). For applications of piperazine derivatives, see: Kaur *et al.* (2010[@bb15]); Eswaran *et al.* (2010[@bb12]); Chou *et al.* (2010[@bb8]); Chen *et al.* (2004[@bb7]); Shingalapur *et al.* (2009[@bb19]). For related structures with cyclo­hexa­phosphate rings, see: Abid *et al.* (2011[@bb1]); Ameur *et al.* (2013[@bb2]); Amri *et al.* (2009[@bb4]). For related structures with 1-phenyl­piperazine-1,4-diium salts, see: Marouani *et al.* (2010[@bb16]); Ben Gharbia *et al.* (2005[@bb5]). For puckering parameters, see: Cremer & Pople (1975[@bb9]). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein *et al.* (1995[@bb6]). For the synthesis of the precursor, see: Schülke & Kayser (1985[@bb17]).

Experimental   {#sec2}
==============

 {#sec2.1}

### Crystal data   {#sec2.1.1}

2C~12~H~20~N~2~ ^2+^·2H~3~O^+^·P~6~O~18~ ^6−^·2H~2~O*M* *~r~* = 932.50Monoclinic,*a* = 8.630 (6) Å*b* = 14.495 (4) Å*c* = 17.072 (3) Åβ = 114.93 (4)°*V* = 1936.6 (15) Å^3^*Z* = 2Ag *K*α radiationλ = 0.56085 Åμ = 0.20 mm^−1^*T* = 293 K0.60 × 0.40 × 0.10 mm

### Data collection   {#sec2.1.2}

Nonius MACH-3 diffractometerAbsorption correction: refined from Δ*F* (Walker & Stuart, 1983[@bb20]) *T* ~min~ = 0.892, *T* ~max~ = 0.98112060 measured reflections9442 independent reflections5475 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.0312 standard reflections every 120 min intensity decay: none

### Refinement   {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.055*wR*(*F* ^2^) = 0.152*S* = 0.999442 reflections253 parametersH-atom parameters constrainedΔρ~max~ = 0.87 e Å^−3^Δρ~min~ = −0.67 e Å^−3^

 {#d5e709}

Data collection: *CAD-4 EXPRESS* (Enraf--Nonius, 1994[@bb11]); cell refinement: *CAD-4 EXPRESS*; data reduction: *XCAD4* (Harms & Wocadlo, 1996[@bb14]); program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb18]); program(s) used to refine structure: *SHELXL97* (Sheldrick, 2008[@bb18]); molecular graphics: *ORTEP-3 for Windows* (Farrugia, 2012[@bb13]); software used to prepare material for publication: *WinGX* (Farrugia, 2012[@bb13]).

Supplementary Material
======================

Crystal structure: contains datablock(s) I, global. DOI: [10.1107/S1600536813016759/jj2168sup1.cif](http://dx.doi.org/10.1107/S1600536813016759/jj2168sup1.cif)

Structure factors: contains datablock(s) I. DOI: [10.1107/S1600536813016759/jj2168Isup2.hkl](http://dx.doi.org/10.1107/S1600536813016759/jj2168Isup2.hkl)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?jj2168&file=jj2168sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?jj2168sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?jj2168&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [JJ2168](http://scripts.iucr.org/cgi-bin/sendsup?jj2168)).

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).

Comment
=======

The literature reports several cyclohexaphosphates of organic cations and/or inorganic cations (Durif,1995). However, cyclohexaphosphates of mixed cations associating the oxoniumion are still relatively very limited. Up to now, only two examples have been known and structurally characterized (Amri *et al.*, 2008, Marouani *et al.*,2010). In this work, we report the preparation and the structural investigation of a new organic oxonium cyclohexaphospohate, 2(C~12~H~20~N~2~)^2+^.2H~3~O^+^.P~6~O~18~^6-^. 2H~2~O, (I), where the organic species is the piperazinium group. Piperazine derivatives have wide range of applications in pharmaceuticals as antimalarial (Kaur *et al.*, 2010), anti-tuberculosis (Eswaran *et al.*, 2010), antitumor (Chou *et al.*, 2010), anticancer (Chen *et al.*, 2004) and antiviral (Shingalapur *et al.*, 2009) agents.

The asymmetric unit of (I) includes one-half of the P~6~O~18~ ring lying on an inversion center (1/2, 1/2, 0), one 1-(2,3-dimethylphenyl) piperazine-1,4-diium cation, one hydronium cation and one water molecule (Fig.1). As shown in Fig.2, the hydronium cations (OW2) bridge the anionic ring to form 2-D corrugated layers, located at *x* = 1/2 and parallel to the *bc*-plane. The result of these interactions is the formation of a 36-membered ring with an *R*~4~^8^(36) graph-set motif (Bernstein *et al.*, 1995). The centre of 36-membered ring is situated on a crystallographic centre of symmetry. Inside these layers, the phosphoric rings display a chair conformation with geometrical characteristics that show no significant difference in deviation from those observed in other cyclohexaphosphates having the same internal symmetry -1 (Amri *et al.*, 2009; Abid *et al.*, 2011; Ameur *et al.*, 2013). The anchorage of the water molecule OW1 and the organic cations is made by short and long H-bonds, ensuring the interconnection between layers, and thus giving rise to a three-dimensional network. The benzyl ring (C5---C10) is essentially planar with an r.m.s. deviation of 0.0047 Å and is orientated at an angle of 54.09 (5)° with respect to the piperazine ring (Fig.3). The piperazine (N1--N2/C1--C4) ring adopts a chair conformation \[puckering parameters: Q~T~ = 0.577 (2) Å, θ = 0.7 (2)° and φ = 326 (12) (Cremer & Pople, 1975)\] with atoms N1 and N2 deviating by -0.683 (2) and 0.657 (2) Å from the least-squares plane defined by the remaining atoms in the ring. The interatomic bond lengths (C---C,*N*---C) and angles in (C---C---C,*C*---N---C) do not show significant deviation from those reported in a related 1-phenylpiperazine-1,4-diium salt (Ben Gharbia *et al.*, 2005). An extensive network of N---H···O and O---H···O hydrogen-bonding interactions link the components of the structure into a three-dimensional network (Fig. 3).

Experimental {#experimental}
============

Crystals of the title compound were prepared by adding dropwise an ethanolic solution (5 ml) of 1-(2,3)dimethlphenylpiperazine (4 mmol) to an aqueous solution (10 ml) of cyclohexaphosphoric acid (2 mmol). The reaction mixture was stirred at room temperature for few minutes. X-ray quality crystals of the title compound appeared after a few days. The cyclohexaphosphoric acid H~6~P~6~O~18~, was produced from Li~6~P~6~O~18~.6H~2~O, prepared according to the procedure of Schülke and Kayser (Schülke & Kayser, 1985), through an ion-exchange resin in H-state (Amberlite IR 120).

Refinement {#refinement}
==========

H1W1, H1W2, H2W1, H2W2 and H3W2 were located by Fourier maps and refined as riding in their as-found relative positions with *U*~iso~(H) = 1.5*U*~eq~(O). All remaining H atoms were placed in their calculated positions and then refined using the riding model with atom-H lengths of 0.93 Å (CH), 0.97 Å (CH~2~), 0.96 Å (CH~3~), 0.91 Å (NH) and 0.90 Å (NH~3~). *U*~iso~ were set to 1.2 (CH, CH~2~), 1.5 (CH~3~) or 1.20 (NH) times *U*~eq~ of the parent atom.

Figures
=======

![The molecular structure of (I) with 50% probability displacement ellipsoids. Dashed lines indicate O---H···O and N---H···O hydrogen bonds.](e-69-o1145-fig1){#Fap1}

![Fig, 2. Projection along the a axis, of an inorganic layer in the structure of (I). The dashed circles highlight the R48(36) centrosymmetric motifs.](e-69-o1145-fig2){#Fap2}

![(a) The three-dimensional network of (I), projected along the aaxis. (b) Relative orientation of the rings aryl and piperazine in the 1-(2,3-Dimethylphenyl)piperazine-1,4-diium cation.](e-69-o1145-fig3){#Fap3}

Crystal data {#tablewrapcrystaldatalong}
============

  ---------------------------------------------------- -------------------------------------
  2C~12~H~20~N~2~^2+^·2H~3~O^+^·P~6~O~18~^6−^·2H~2~O   *F*(000) = 976
  *M~r~* = 932.50                                      *D*~x~ = 1.599 Mg m^−3^
  Monoclinic, *P*2~1~/*c*                              Ag *K*α radiation, λ = 0.56085 Å
  Hall symbol: -P 2ybc                                 Cell parameters from 25 reflections
  *a* = 8.630 (6) Å                                    θ = 9.3--10.5°
  *b* = 14.495 (4) Å                                   µ = 0.20 mm^−1^
  *c* = 17.072 (3) Å                                   *T* = 293 K
  β = 114.93 (4)°                                      Prism, colourless
  *V* = 1936.6 (15) Å^3^                               0.60 × 0.40 × 0.10 mm
  *Z* = 2                                              
  ---------------------------------------------------- -------------------------------------

Data collection {#tablewrapdatacollectionlong}
===============

  ------------------------------------------------------------------------------------ --------------------------------------
  Nonius MACH-3 diffractometer                                                         5475 reflections with *I* \> 2σ(*I*)
  Radiation source: fine-focus sealed tube                                             *R*~int~ = 0.031
  Graphite monochromator                                                               θ~max~ = 28.0°, θ~min~ = 2.1°
  non--profiled ω scans                                                                *h* = −14→14
  Absorption correction: part of the refinement model (Δ*F*) (Walker & Stuart, 1983)   *k* = −24→2
  *T*~min~ = 0.892, *T*~max~ = 0.981                                                   *l* = −28→16
  12060 measured reflections                                                           2 standard reflections every 120 min
  9442 independent reflections                                                         intensity decay: none
  ------------------------------------------------------------------------------------ --------------------------------------

Refinement {#tablewraprefinementdatalong}
==========

  ------------------------------------- -------------------------------------------------------------------------------------
  Refinement on *F*^2^                  Primary atom site location: structure-invariant direct methods
  Least-squares matrix: full            Secondary atom site location: difference Fourier map
  *R*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.055   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.152                  H-atom parameters constrained
  *S* = 0.99                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0763*P*)^2^\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  9442 reflections                      (Δ/σ)~max~ \< 0.001
  253 parameters                        Δρ~max~ = 0.87 e Å^−3^
  0 restraints                          Δρ~min~ = −0.67 e Å^−3^
  0 constraints                         
  ------------------------------------- -------------------------------------------------------------------------------------

Special details {#specialdetails}
===============

  -----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
  Geometry. All e.s.d.\'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.\'s are taken into account individually in the estimation of e.s.d.\'s in distances, angles and torsion angles; correlations between e.s.d.\'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.\'s is used for estimating e.s.d.\'s involving l.s. planes.
  Refinement. Refinement of *F*^2^ against ALL reflections. The weighted *R*-factor *wR* and goodness of fit *S* are based on *F*^2^, conventional *R*-factors *R* are based on *F*, with *F* set to zero for negative *F*^2^. The threshold expression of *F*^2^ \> σ(*F*^2^) is used only for calculating *R*-factors(gt) *etc*. and is not relevant to the choice of reflections for refinement. *R*-factors based on *F*^2^ are statistically about twice as large as those based on *F*, and *R*- factors based on ALL data will be even larger.
  -----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å^2^) {#tablewrapcoords}
==================================================================================================

  ------ -------------- --------------- --------------- -------------------- --
         *x*            *y*             *z*             *U*~iso~\*/*U*~eq~   
  P1     0.31249 (5)    0.34945 (3)     −0.07303 (3)    0.02004 (9)          
  P2     0.37416 (6)    0.39535 (3)     0.10432 (3)     0.02228 (10)         
  P3     0.69777 (6)    0.49655 (3)     0.18679 (3)     0.02396 (10)         
  O1     0.42651 (16)   0.30040 (10)    −0.10364 (9)    0.0287 (3)           
  O2     0.14736 (17)   0.30794 (10)    −0.08650 (11)   0.0345 (3)           
  O3     0.2778 (2)     0.45146 (10)    −0.11034 (11)   0.0385 (4)           
  O4     0.42266 (17)   0.36921 (13)    0.02683 (9)     0.0403 (4)           
  O5     0.19648 (16)   0.42960 (10)    0.07175 (10)    0.0321 (3)           
  O6     0.4264 (2)     0.31760 (10)    0.16614 (10)    0.0351 (3)           
  O7     0.49427 (17)   0.48166 (9)     0.14480 (10)    0.0325 (3)           
  O8     0.7354 (2)     0.55904 (12)    0.26036 (10)    0.0448 (4)           
  O9     0.7852 (2)     0.40717 (10)    0.19877 (12)    0.0419 (4)           
  OW1    1.0380 (3)     0.2895 (2)      0.25912 (15)    0.0936 (10)          
  H1W1   0.9712         0.3308          0.2474          0.140\*              
  H2W1   1.0790         0.2734          0.3123          0.140\*              
  OW2    0.79099 (19)   0.72073 (11)    0.31371 (10)    0.0372 (3)           
  H1W2   0.7581         0.6706          0.2912          0.056\*              
  H2W2   0.8182         0.7360          0.2764          0.056\*              
  H3W2   0.7184         0.7547          0.3209          0.056\*              
  C1     0.8112 (2)     0.37054 (13)    0.00581 (13)    0.0295 (4)           
  H1A    0.6935         0.3897          −0.0121         0.035\*              
  H1B    0.8824         0.4074          0.0554          0.035\*              
  C2     0.8290 (3)     0.26990 (14)    0.03063 (13)    0.0302 (4)           
  H2C    0.9484         0.2523          0.0532          0.036\*              
  H2D    0.7907         0.2605          0.0759          0.036\*              
  C3     0.7820 (3)     0.22745 (13)    −0.11665 (13)   0.0282 (4)           
  H3A    0.7134         0.1904          −0.1667         0.034\*              
  H3B    0.9005         0.2093          −0.0976         0.034\*              
  C4     0.7625 (3)     0.32817 (13)    −0.14143 (14)   0.0299 (4)           
  H4A    0.8012         0.3384          −0.1865         0.036\*              
  H4B    0.6429         0.3454          −0.1640         0.036\*              
  C5     0.7366 (2)     0.10980 (12)    −0.02396 (12)   0.0258 (3)           
  C6     0.6060 (2)     0.05226 (13)    −0.07716 (12)   0.0265 (3)           
  C7     0.6213 (3)     −0.04254 (14)   −0.05737 (14)   0.0335 (4)           
  C8     0.7617 (3)     −0.07472 (15)   0.01414 (17)    0.0421 (5)           
  H8     0.7708         −0.1374         0.0270          0.051\*              
  C9     0.8877 (3)     −0.01554 (16)   0.06639 (17)    0.0433 (5)           
  H9     0.9801         −0.0383         0.1144          0.052\*              
  C10    0.8771 (3)     0.07749 (16)    0.04755 (15)    0.0364 (5)           
  H10    0.9623         0.1178          0.0821          0.044\*              
  C11    0.4528 (3)     0.08562 (15)    −0.15409 (13)   0.0354 (4)           
  H13    0.4447         0.1515          −0.1513         0.053\*              
  H11    0.3517         0.0578          −0.1544         0.053\*              
  H14    0.4639         0.0690          −0.2059         0.053\*              
  C12    0.4877 (4)     −0.10878 (16)   −0.11266 (19)   0.0477 (6)           
  H122   0.3770         −0.0866         −0.1210         0.072\*              
  H121   0.5077         −0.1680         −0.0850         0.072\*              
  H123   0.4924         −0.1144         −0.1676         0.072\*              
  N1     0.72640 (18)   0.20991 (10)    −0.04534 (10)   0.0227 (3)           
  H1     0.6150         0.2273          −0.0649         0.027\*              
  N2     0.8629 (2)     0.38610 (11)    −0.06582 (12)   0.0298 (3)           
  H2A    0.8476         0.4459          −0.0813         0.036\*              
  H2B    0.9746         0.3729          −0.0475         0.036\*              
  ------ -------------- --------------- --------------- -------------------- --

Atomic displacement parameters (Å^2^) {#tablewrapadps}
=====================================

  ----- -------------- -------------- ------------- --------------- -------------- ---------------
        *U*^11^        *U*^22^        *U*^33^       *U*^12^         *U*^13^        *U*^23^
  P1    0.01473 (16)   0.02149 (19)   0.0252 (2)    −0.00054 (15)   0.00971 (15)   −0.00045 (17)
  P2    0.02042 (19)   0.02102 (19)   0.0271 (2)    −0.00034 (15)   0.01164 (17)   −0.00057 (17)
  P3    0.02164 (19)   0.02002 (19)   0.0283 (2)    0.00048 (16)    0.00867 (17)   0.00217 (17)
  O1    0.0217 (6)     0.0296 (7)     0.0363 (7)    0.0055 (5)      0.0137 (5)     −0.0021 (6)
  O2    0.0221 (6)     0.0335 (7)     0.0522 (9)    −0.0093 (5)     0.0197 (6)     −0.0100 (7)
  O3    0.0558 (10)    0.0228 (6)     0.0560 (10)   0.0102 (6)      0.0420 (8)     0.0084 (7)
  O4    0.0196 (6)     0.0758 (12)    0.0257 (7)    0.0018 (7)      0.0099 (5)     −0.0072 (8)
  O5    0.0205 (6)     0.0297 (7)     0.0475 (8)    0.0007 (5)      0.0157 (6)     −0.0001 (6)
  O6    0.0388 (8)     0.0270 (7)     0.0420 (8)    0.0021 (6)      0.0195 (7)     0.0086 (6)
  O7    0.0224 (6)     0.0209 (6)     0.0518 (9)    −0.0013 (5)     0.0132 (6)     −0.0039 (6)
  O8    0.0574 (10)    0.0368 (9)     0.0331 (8)    −0.0078 (8)     0.0122 (7)     −0.0075 (7)
  O9    0.0328 (8)     0.0290 (7)     0.0603 (10)   0.0119 (6)      0.0160 (7)     0.0105 (7)
  OW1   0.0987 (18)    0.134 (2)      0.0705 (14)   0.0923 (17)     0.0579 (14)    0.0573 (15)
  OW2   0.0349 (7)     0.0385 (8)     0.0389 (8)    −0.0028 (6)     0.0162 (7)     −0.0106 (7)
  C1    0.0236 (8)     0.0264 (8)     0.0393 (10)   −0.0026 (7)     0.0139 (8)     −0.0055 (8)
  C2    0.0283 (9)     0.0289 (9)     0.0304 (9)    −0.0021 (7)     0.0093 (7)     −0.0018 (8)
  C3    0.0316 (9)     0.0249 (8)     0.0363 (10)   0.0015 (7)      0.0223 (8)     0.0021 (7)
  C4    0.0297 (9)     0.0280 (9)     0.0369 (10)   0.0011 (7)      0.0188 (8)     0.0048 (8)
  C5    0.0272 (8)     0.0216 (8)     0.0324 (9)    0.0038 (6)      0.0164 (7)     0.0035 (7)
  C6    0.0323 (9)     0.0245 (8)     0.0299 (9)    0.0023 (7)      0.0200 (7)     0.0014 (7)
  C7    0.0459 (11)    0.0222 (8)     0.0442 (11)   0.0000 (8)      0.0305 (10)    −0.0008 (8)
  C8    0.0526 (14)    0.0252 (9)     0.0598 (15)   0.0097 (9)      0.0346 (12)    0.0128 (10)
  C9    0.0426 (12)    0.0339 (11)    0.0497 (13)   0.0126 (9)      0.0158 (10)    0.0146 (10)
  C10   0.0310 (10)    0.0325 (10)    0.0413 (11)   0.0075 (8)      0.0110 (9)     0.0076 (9)
  C11   0.0364 (10)    0.0329 (10)    0.0335 (10)   −0.0052 (8)     0.0115 (8)     −0.0028 (8)
  C12   0.0568 (15)    0.0290 (10)    0.0662 (17)   −0.0098 (10)    0.0346 (13)    −0.0116 (11)
  N1    0.0199 (6)     0.0212 (6)     0.0289 (7)    0.0015 (5)      0.0120 (6)     0.0014 (6)
  N2    0.0210 (6)     0.0226 (7)     0.0483 (10)   0.0014 (6)      0.0170 (7)     0.0031 (7)
  ----- -------------- -------------- ------------- --------------- -------------- ---------------

Geometric parameters (Å, º) {#tablewrapgeomlong}
===========================

  ---------------------- -------------- --------------------- --------------
  P1---O2                1.4729 (16)    C3---H3A              0.9700
  P1---O1                1.4766 (15)    C3---H3B              0.9700
  P1---O3                1.5878 (15)    C4---N2               1.476 (3)
  P1---O4                1.5894 (16)    C4---H4A              0.9700
  P2---O6                1.4785 (15)    C4---H4B              0.9700
  P2---O5                1.4792 (17)    C5---C6               1.388 (3)
  P2---O7                1.5855 (15)    C5---C10              1.390 (3)
  P2---O4                1.5924 (15)    C5---N1               1.490 (2)
  P3---O8                1.4696 (17)    C6---C7               1.408 (3)
  P3---O9                1.4696 (15)    C6---C11              1.497 (3)
  P3---O3^i^             1.5964 (15)    C7---C8               1.389 (3)
  P3---O7                1.6073 (19)    C7---C12              1.491 (3)
  O3---P3^i^             1.5964 (15)    C8---C9               1.377 (4)
  OW1---H1W1             0.7950         C8---H8               0.9300
  OW1---H2W1             0.8565         C9---C10              1.380 (3)
  OW2---H1W2             0.8154         C9---H9               0.9300
  OW2---H2W2             0.7977         C10---H10             0.9300
  OW2---H3W2             0.8458         C11---H13             0.9600
  C1---N2                1.485 (3)      C11---H11             0.9600
  C1---C2                1.509 (3)      C11---H14             0.9600
  C1---H1A               0.9700         C12---H122            0.9600
  C1---H1B               0.9700         C12---H121            0.9600
  C2---N1                1.501 (2)      C12---H123            0.9600
  C2---H2C               0.9700         N1---H1               0.9100
  C2---H2D               0.9700         N2---H2A              0.9000
  C3---N1                1.506 (2)      N2---H2B              0.9000
  C3---C4                1.509 (3)                            
                                                              
  O2---P1---O1           119.56 (9)     N2---C4---H4B         109.6
  O2---P1---O3           108.13 (9)     C3---C4---H4B         109.6
  O1---P1---O3           110.35 (8)     H4A---C4---H4B        108.1
  O2---P1---O4           110.06 (9)     C6---C5---C10         122.63 (18)
  O1---P1---O4           106.25 (9)     C6---C5---N1          118.49 (16)
  O3---P1---O4           100.89 (10)    C10---C5---N1         118.88 (17)
  O6---P2---O5           118.69 (9)     C5---C6---C7          117.46 (18)
  O6---P2---O7           110.10 (9)     C5---C6---C11         123.56 (17)
  O5---P2---O7           106.42 (9)     C7---C6---C11         118.97 (18)
  O6---P2---O4           107.69 (10)    C8---C7---C6          119.8 (2)
  O5---P2---O4           111.19 (9)     C8---C7---C12         119.7 (2)
  O7---P2---O4           101.38 (9)     C6---C7---C12         120.5 (2)
  O8---P3---O9           120.58 (11)    C9---C8---C7          121.2 (2)
  O8---P3---O3^i^        110.49 (10)    C9---C8---H8          119.4
  O9---P3---O3^i^        107.03 (9)     C7---C8---H8          119.4
  O8---P3---O7           105.68 (10)    C8---C9---C10         120.0 (2)
  O9---P3---O7           110.14 (9)     C8---C9---H9          120.0
  O3^i^---P3---O7        101.25 (9)     C10---C9---H9         120.0
  P1---O3---P3^i^        134.42 (10)    C9---C10---C5         118.8 (2)
  P1---O4---P2           133.32 (10)    C9---C10---H10        120.6
  P2---O7---P3           133.71 (9)     C5---C10---H10        120.6
  H1W1---OW1---H2W1      113.9          C6---C11---H13        109.5
  H1W2---OW2---H2W2      91.8           C6---C11---H11        109.5
  H1W2---OW2---H3W2      117.1          H13---C11---H11       109.5
  H2W2---OW2---H3W2      116.2          C6---C11---H14        109.5
  N2---C1---C2           110.34 (16)    H13---C11---H14       109.5
  N2---C1---H1A          109.6          H11---C11---H14       109.5
  C2---C1---H1A          109.6          C7---C12---H122       109.5
  N2---C1---H1B          109.6          C7---C12---H121       109.5
  C2---C1---H1B          109.6          H122---C12---H121     109.5
  H1A---C1---H1B         108.1          C7---C12---H123       109.5
  N1---C2---C1           111.36 (16)    H122---C12---H123     109.5
  N1---C2---H2C          109.4          H121---C12---H123     109.5
  C1---C2---H2C          109.4          C5---N1---C2          113.59 (15)
  N1---C2---H2D          109.4          C5---N1---C3          110.88 (14)
  C1---C2---H2D          109.4          C2---N1---C3          109.11 (14)
  H2C---C2---H2D         108.0          C5---N1---H1          107.7
  N1---C3---C4           110.72 (15)    C2---N1---H1          107.7
  N1---C3---H3A          109.5          C3---N1---H1          107.7
  C4---C3---H3A          109.5          C4---N2---C1          111.35 (15)
  N1---C3---H3B          109.5          C4---N2---H2A         109.4
  C4---C3---H3B          109.5          C1---N2---H2A         109.4
  H3A---C3---H3B         108.1          C4---N2---H2B         109.4
  N2---C4---C3           110.49 (16)    C1---N2---H2B         109.4
  N2---C4---H4A          109.6          H2A---N2---H2B        108.0
  C3---C4---H4A          109.6                                
                                                              
  O2---P1---O3---P3^i^   −116.25 (16)   C5---C6---C7---C8     1.2 (3)
  O1---P1---O3---P3^i^   16.22 (19)     C11---C6---C7---C8    −179.47 (19)
  O4---P1---O3---P3^i^   128.25 (16)    C5---C6---C7---C12    −178.77 (18)
  O2---P1---O4---P2      −31.2 (2)      C11---C6---C7---C12   0.6 (3)
  O1---P1---O4---P2      −162.03 (16)   C6---C7---C8---C9     −0.2 (3)
  O3---P1---O4---P2      82.82 (18)     C12---C7---C8---C9    179.7 (2)
  O6---P2---O4---P1      114.23 (17)    C7---C8---C9---C10    −0.8 (4)
  O5---P2---O4---P1      −17.4 (2)      C8---C9---C10---C5    0.8 (4)
  O7---P2---O4---P1      −130.16 (17)   C6---C5---C10---C9    0.2 (3)
  O6---P2---O7---P3      53.82 (17)     N1---C5---C10---C9    −178.9 (2)
  O5---P2---O7---P3      −176.32 (13)   C6---C5---N1---C2     157.24 (16)
  O4---P2---O7---P3      −59.98 (16)    C10---C5---N1---C2    −23.6 (2)
  O8---P3---O7---P2      −140.97 (14)   C6---C5---N1---C3     −79.5 (2)
  O9---P3---O7---P2      −9.23 (18)     C10---C5---N1---C3    99.7 (2)
  O3^i^---P3---O7---P2   103.78 (15)    C1---C2---N1---C5     −178.79 (15)
  N2---C1---C2---N1      −56.9 (2)      C1---C2---N1---C3     57.0 (2)
  N1---C3---C4---N2      58.0 (2)       C4---C3---N1---C5     176.94 (15)
  C10---C5---C6---C7     −1.2 (3)       C4---C3---N1---C2     −57.2 (2)
  N1---C5---C6---C7      177.91 (16)    C3---C4---N2---C1     −57.5 (2)
  C10---C5---C6---C11    179.48 (19)    C2---C1---N2---C4     56.8 (2)
  N1---C5---C6---C11     −1.4 (3)                             
  ---------------------- -------------- --------------------- --------------

Symmetry code: (i) −*x*+1, −*y*+1, −*z*.

Hydrogen-bond geometry (Å, º) {#tablewraphbondslong}
=============================

  ----------------------------- --------- --------- ----------- ---------------
  *D*---H···*A*                 *D*---H   H···*A*   *D*···*A*   *D*---H···*A*
  O*W*1---H1*W*1···O9           0.79      1.84      2.614 (3)   166
  O*W*1---H2*W*1···O2^ii^       0.86      1.97      2.781 (3)   159
  O*W*2---H1*W*2···O8           0.82      1.69      2.487 (2)   167
  O*W*2---H2*W*2···O*W*1^iii^   0.80      1.77      2.503 (3)   152
  O*W*2---H3*W*2···O6^iv^       0.85      1.64      2.481 (2)   178
  N1---H1···O1                  0.91      1.82      2.690 (2)   160
  N2---H2*A*···O5^i^            0.90      1.87      2.714 (2)   156
  N2---H2*B*···O2^v^            0.90      2.10      2.858 (3)   142
  N2---H2*B*···O5^v^            0.90      2.28      2.916 (3)   127
  ----------------------------- --------- --------- ----------- ---------------

Symmetry codes: (i) −*x*+1, −*y*+1, −*z*; (ii) *x*+1, −*y*+1/2, *z*+1/2; (iii) −*x*+2, *y*+1/2, −*z*+1/2; (iv) −*x*+1, *y*+1/2, −*z*+1/2; (v) *x*+1, *y*, *z*.

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*                *D*---H   H⋯*A*   *D*⋯*A*     *D*---H⋯*A*
  -------------------------- --------- ------- ----------- -------------
  O*W*1---H1*W*1⋯O9          0.79      1.84    2.614 (3)   166
  O*W*1---H2*W*1⋯O2^i^       0.86      1.97    2.781 (3)   159
  O*W*2---H1*W*2⋯O8          0.82      1.69    2.487 (2)   167
  O*W*2---H2*W*2⋯O*W*1^ii^   0.80      1.77    2.503 (3)   152
  O*W*2---H3*W*2⋯O6^iii^     0.85      1.64    2.481 (2)   178
  N1---H1⋯O1                 0.91      1.82    2.690 (2)   160
  N2---H2*A*⋯O5^iv^          0.90      1.87    2.714 (2)   156
  N2---H2*B*⋯O2^v^           0.90      2.10    2.858 (3)   142
  N2---H2*B*⋯O5^v^           0.90      2.28    2.916 (3)   127

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .
