Ethyl­enedi­ammonium disodium (1-hydroxy­ethyl­idene)­di­phospho­nate tetrahydrate, [NH3(CH2)2NH3]Na2(hedp)·­4H2O

Wu, Z.-B.; Liu, Z.-M.; Tian, P.; Xu, L.; He, Y.-L.; Sang, S.-Y.; Yang, Y.; Liu, X.-M.; Liu, X.-C.; Bao, X.-H.

doi:10.1107/S1600536803013278

Ethylenediammonium disodium (1-hydroxyethylidene)diphosphonate tetrahydrate, [NH₃(CH₂)₂NH₃]Na₂(hedp)·4H₂O

Z.-B. Wu, Z.-M. Liu, P. Tian, L. Xu, Y.-L. He, S.-Y. Sang, Y. Yang, X.-M. Liu, X.-C. Liu and X.-H. Bao

The title structure, C₂H₁₀N₂²⁺·2Na⁺·C₂H₄O₇P₂⁴⁻·4H₂O or (NH₃CH₂CH₂NH₃)Na₂(hedp)·4H₂O (SDP-2) (hedp = 1-hydroxyethylidenediphosphonate), contains one-dimensional anionic sodium–hedp chains which are connected by N—H

O and O—H

O hydrogen bonds. There are two crystallographically independent P atom environments.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803013278/lh6070sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803013278/lh6070Isup2.hkl Contains datablock I

CCDC reference: 194948

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.026
wR factor = 0.064
Data-to-parameter ratio = 9.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



PLAT_420  Alert B D-H Without Acceptor       O9     -   H9A    ...          ?

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           25.02
         From the CIF: _reflns_number_total               2203
         Count of symmetry unique reflns         1351
         Completeness (_total/calc)            163.06%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured       852
         Fraction of Friedel pairs measured     0.631
         Are heavy atom types Z>Si present          yes
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.


 0 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 0 Alert Level C = Please check

Comment top

Hydroxyethane-1,1-diphosphonic acid (H₄hedp), which has a characteristic P—C—P linkage, finds applications in biomedical areas, water treatment, ion exchange and lipophlic solvent extraction (Francis et al., 1969; Jurisson et al., 1993). Recently, owing to its versatile coordination abilities with metal ions, the compound has been introduced into the field of materials and used as a polydentate ligand to construct novel structures with special properties (Serezhkin et al., 2000; Sergienko, 2000; Nash et al., 1998). Hedp possesses seven active oxygen atoms, so, at most, it can serve as a heptadentate ligand. Furthermore, the CH₃ and OH groups attached to the organic tether of hedp not only provide a steric hindrance, but also a possible hydrophobic or hydrophilic environment which may be important in the self-assembly of some metal diphosphonates.

More recently, many efforts have been devoted to synthesizing open-framework metal–hedp compounds. The idea was highlighted by the studies on Sn₂(hedp) (Zapf et al., 1996). Attempting to obtain novel structures, Zheng et al. (2000, 2001) using different organic amines as the template, synthesized several metal–hedp compounds with different structures (Zheng et al., 2000, 2002; Song et al., 2001). The authors attributed the structural difference among the compounds to the effect of the templates employed. The smaller size template NH₂CH₂CH₂NH₂ (en) directed the formation of a linear single chain compound; while the larger size templates such as NH₂(CH₂)_mNH₂ (m = 4, 5, 6) directed the formation of anionic double chains which were held together by strong hydrogen bonds to form three-dimensional channels. The use of organic amines as templates in the above synthesizing process is relatively new, which not only diversifies the members of the family but also adds a promising direction for the future studies of the compounds.

In the present paper, we describe the synthesis and crystal structure of a new member of the metal-hedp series, (NH₃CH₂CH₂NH₃)Na₂(hedp)·4H₂O (designated as SDP2), (I).

The fundamental building unit of SDP2 is the extended one-dimensional anionic [Na₂(hedp)(H₂O)₃]^2- chains along the b axis, which are charge-balanced by enH₂²⁺ cations and linked together by hydrogen bonds (Figs 1 and 2). Within a chain, two kinds of Na atom environments are found. The Na1 atom links with the hedp ligand through atoms O1 and O7 from one ligand and O3ⁱ, O4ⁱ and O5ⁱ [symmetry code: (i) x, 1 + y, z] from another neighboring ligand. Being different from Na1, there are three bonds from water molecules, O8, O9 and O10 and three bonds from the hedp ligand through O3, O5 and O7 contributing to the coordination of Na2. For the two tetrahedral coordinated P atoms in a ligand, there are two pendant {PO} bonds in the form of P═O, namely P1═O2 and P2═O6. The lengths of the P═O is 1.5231 (19) and 1.514 (2) Å, respectively. In comparison with the P═O bond lengths in H₄hedp and other metal–hedp compounds, the distance is longer, which can be explained by the fact that there are strong hydrogen bonds between the P ═O and the enH₂²⁺. Here hedp acts as a pentadentate ligand, bridging the Na atoms through four ionized O(P) atoms of the two diphosphonate groups and the protonated O(C) atom of the hydroxyl group. The torsion angles for O2—P1—C1—P2 and O6—P2—C1—P1 are -166.84 (12) and -166.68 (15)°, respectively. In structural contrast between SDP2 and another disodium 1-hydroxylidenediphosphonate tetrahydrate (Barnett et al., 1979), the effect of ethylenediamine on tailoring the structure of the sodium 1-hydroxylidenediphosphonate is obvious. Between the chains, the protonated enH₂²⁺ and acts as a charge-compensating cation and also bridges the chains through N—H···O hydrogen bonds. Three coordinated water molecules O8, O9 and O10 and one lattice water O11 also contribute to the hydrogen-bonding motif (see Table 2). It is the strong hydrogen bonds that help stabilize the crystal structure.

Experimental top

All starting materials were analytical pure and used without further purification. SDP2 was prepared by the following method. Na₄C₂H₄O₇P₂, NH₄F(ammonium fluoride), H₂O(deionized water) and C₄H₈O₂ (dioxane), in a 1:0.2:80:2 molar ratio, were stirred at ambient temperature in a plastic container. Ethylenediamine was added dropwise to the mixture until a pH of 10 was achieved. Stirring was continued until a homogeneous white gel formed. The container was covered with a watch glass, and left undisturbed at ambient temperature. After two weeks, transparent and colorless crystals began to form. The purity of SDP2 was verified by elemental analysis: calculated for C₄H₂₂N₂Na₂O₁₁P₂ (wt%): C 12.57, H 5.81, N 7.33, Na 12.03, P 16.21; found: C 11.90, H 4.73, N 7.07, Na 11.85, P 15.30. F T–IR (KBr pellet,ν cm^-1: 3259, 3103, 2993, 2988, 2130, 1719, 1648, 996, 955, 885, 806, 733. ¹³C CP/MAS NMR (external reference: DSS, δ p.p.m.): 22.8 (CH₃), 36.7 (CH₂CH₂), and 72.1 (≡C); ³¹P MAS NMR (external reference: 85% H₃PO₄, δ p.p.m.): 20.1 and 17.9.

Structure description top

In the present paper, we describe the synthesis and crystal structure of a new member of the metal-hedp series, (NH₃CH₂CH₂NH₃)Na₂(hedp)·4H₂O (designated as SDP2), (I).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SHELXTL (Sheldrick, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The asymmetric unit of SDP2 with the atomic labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate the hydrogen-bonding interactions.
	Fig. 2. SDP2 structure viewed along [010]. Displacement ellipsoids are drawn at the 60% probability level. Key: C atoms, gray; H atoms, white; N atoms, yellow; P atoms, green; Na atoms, red; O atoms, blue).

Ethylenediammonium disodium (1-hydroxyethylidene)diphosphonate tetrahydrate top

Crystal data top

C₂H₁₀N₂²⁺·2Na⁺·C₂H₄O₇P₂⁴⁻·4H₂O	F(000) = 800
M_r = 382.16	D_x = 1.731 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c-2n	Cell parameters from 2203 reflections
a = 20.966 (7) Å	θ = 1.9–25.0°
b = 5.8928 (18) Å	µ = 0.41 mm⁻¹
c = 11.871 (4) Å	T = 293 K
V = 1466.6 (8) Å³	Arching, colourless
Z = 4	0.20 × 0.10 × 0.10 mm

Data collection top

Bruker SMART CCD diffractometer	2203 independent reflections
Radiation source: fine-focus sealed tube	2021 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
φ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→22
T_min = 0.922, T_max = 0.960	k = −7→4
5700 measured reflections	l = −12→14

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.026	H-atom parameters constrained
wR(F²) = 0.064	w = 1/[σ²(F_o²) + (0.0395P)²] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
2203 reflections	Δρ_max = 0.27 e Å⁻³
236 parameters	Δρ_min = −0.31 e Å⁻³
13 restraints	Absolute structure: Flack (1983), 1217 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.10 (10)

Crystal data top

C₂H₁₀N₂²⁺·2Na⁺·C₂H₄O₇P₂⁴⁻·4H₂O	V = 1466.6 (8) Å³
M_r = 382.16	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 20.966 (7) Å	µ = 0.41 mm⁻¹
b = 5.8928 (18) Å	T = 293 K
c = 11.871 (4) Å	0.20 × 0.10 × 0.10 mm

Data collection top

Bruker SMART CCD diffractometer	2203 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2021 reflections with I > 2σ(I)
T_min = 0.922, T_max = 0.960	R_int = 0.025
5700 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	H-atom parameters constrained
wR(F²) = 0.064	Δρ_max = 0.27 e Å⁻³
S = 1.06	Δρ_min = −0.31 e Å⁻³
2203 reflections	Absolute structure: Flack (1983), 1217 Friedel pairs
236 parameters	Absolute structure parameter: −0.10 (10)
13 restraints

Special details top

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 F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² 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 (Å²) top

	x	y	z	U_iso*/U_eq
Na1	0.61931 (5)	0.93017 (17)	0.76226 (11)	0.0273 (3)
Na2	0.67051 (6)	0.3420 (2)	0.91792 (10)	0.0291 (3)
P1	0.53935 (3)	0.42129 (11)	0.74458 (6)	0.01483 (16)
O1	0.53603 (9)	0.6738 (3)	0.77194 (16)	0.0235 (5)
C1	0.59651 (13)	0.3776 (4)	0.6273 (2)	0.0164 (6)
P2	0.68185 (3)	0.40810 (10)	0.66815 (6)	0.01623 (16)
O2	0.47523 (8)	0.3352 (3)	0.70202 (16)	0.0209 (4)
C2	0.58056 (14)	0.5353 (5)	0.5298 (2)	0.0236 (6)
H2D	0.5835	0.6901	0.5545	0.035*
H2E	0.5380	0.5050	0.5040	0.035*
H2F	0.6101	0.5103	0.4693	0.035*
O3	0.56466 (8)	0.2817 (3)	0.84275 (16)	0.0217 (4)
O4	0.59212 (10)	0.1408 (3)	0.59455 (19)	0.0240 (5)
H4	0.5590 (17)	0.122 (5)	0.553 (3)	0.032 (9)*
O5	0.70022 (8)	0.2009 (3)	0.73698 (18)	0.0259 (5)
O6	0.71844 (10)	0.4233 (5)	0.5584 (2)	0.0418 (6)
O7	0.68648 (9)	0.6216 (3)	0.7393 (2)	0.0353 (6)
N1	0.78297 (12)	0.8749 (4)	0.8196 (2)	0.0207 (5)
H1A	0.7635 (16)	0.996 (6)	0.791 (3)	0.031*
H1B	0.7900 (16)	0.884 (5)	0.893 (3)	0.031*
H1C	0.7545 (15)	0.762 (5)	0.801 (3)	0.031*
N2	0.92905 (12)	0.5870 (5)	0.7006 (2)	0.0244 (6)
H2A	0.9432 (16)	0.442 (6)	0.700 (3)	0.037*
H2B	0.9586 (16)	0.689 (5)	0.722 (3)	0.037*
H2C	0.9226 (18)	0.615 (5)	0.628 (3)	0.037*
C3	0.84201 (13)	0.8452 (4)	0.7533 (3)	0.0236 (6)
H3A	0.8725	0.9616	0.7744	0.028*
H3B	0.8324	0.8637	0.6739	0.028*
C4	0.87151 (14)	0.6126 (4)	0.7724 (3)	0.0262 (7)
H4A	0.8832	0.5959	0.8511	0.031*
H4B	0.8408	0.4954	0.7540	0.031*
O8	0.66083 (11)	−0.0356 (4)	0.9915 (2)	0.0406 (6)
H8A	0.6361 (12)	−0.150 (4)	0.994 (4)	0.061*
H8B	0.6981 (8)	−0.073 (5)	1.014 (4)	0.061*
O9	0.59591 (11)	0.5420 (4)	1.02754 (19)	0.0354 (5)
H9A	0.5755 (14)	0.471 (6)	0.977 (2)	0.053*
H9B	0.5711 (14)	0.580 (6)	1.082 (2)	0.053*
O10	0.76383 (13)	0.4109 (4)	1.0085 (3)	0.0515 (7)
H10A	0.7860 (16)	0.298 (4)	1.026 (4)	0.077*
H10B	0.7771 (19)	0.534 (3)	1.037 (4)	0.077*
O11	0.50591 (13)	0.9515 (4)	0.9562 (2)	0.0447 (7)
H11A	0.513 (2)	1.075 (3)	0.922 (3)	0.067*
H11B	0.515 (2)	0.839 (4)	0.913 (3)	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Na1	0.0228 (6)	0.0172 (5)	0.0419 (7)	−0.0011 (4)	0.0035 (5)	0.0002 (5)
Na2	0.0269 (6)	0.0346 (6)	0.0258 (6)	0.0021 (5)	−0.0015 (5)	−0.0058 (5)
P1	0.0139 (3)	0.0146 (3)	0.0160 (3)	−0.0005 (2)	0.0002 (3)	0.0001 (3)
O1	0.0209 (10)	0.0166 (10)	0.0329 (13)	0.0000 (7)	0.0036 (9)	−0.0028 (8)
C1	0.0153 (13)	0.0166 (14)	0.0172 (14)	0.0007 (10)	0.0015 (11)	−0.0019 (10)
P2	0.0134 (3)	0.0161 (3)	0.0192 (4)	−0.0008 (3)	0.0002 (3)	0.0003 (3)
O2	0.0146 (9)	0.0225 (9)	0.0256 (10)	−0.0034 (7)	−0.0037 (8)	0.0018 (8)
C2	0.0208 (15)	0.0295 (16)	0.0205 (15)	0.0028 (12)	0.0008 (12)	0.0040 (12)
O3	0.0191 (10)	0.0262 (11)	0.0199 (10)	0.0006 (8)	−0.0019 (8)	0.0061 (8)
O4	0.0205 (11)	0.0192 (10)	0.0322 (12)	0.0004 (8)	−0.0054 (9)	−0.0093 (8)
O5	0.0186 (9)	0.0207 (10)	0.0385 (12)	0.0035 (7)	−0.0036 (9)	0.0083 (9)
O6	0.0189 (12)	0.0798 (19)	0.0266 (12)	−0.0014 (11)	0.0038 (10)	0.0102 (11)
O7	0.0222 (11)	0.0195 (10)	0.0641 (16)	0.0033 (7)	−0.0139 (11)	−0.0160 (11)
N1	0.0187 (13)	0.0202 (14)	0.0233 (14)	0.0014 (10)	−0.0019 (10)	−0.0010 (11)
N2	0.0204 (13)	0.0238 (14)	0.0289 (15)	0.0037 (10)	0.0019 (11)	−0.0028 (11)
C3	0.0216 (14)	0.0253 (14)	0.0239 (15)	0.0005 (11)	0.0011 (13)	0.0013 (12)
C4	0.0226 (14)	0.0254 (16)	0.0305 (18)	0.0006 (11)	0.0005 (12)	0.0018 (13)
O8	0.0258 (13)	0.0398 (13)	0.0563 (17)	−0.0011 (10)	−0.0078 (12)	0.0125 (13)
O9	0.0259 (12)	0.0516 (15)	0.0286 (13)	0.0050 (10)	−0.0005 (10)	−0.0133 (10)
O10	0.0484 (17)	0.0371 (14)	0.069 (2)	−0.0067 (12)	−0.0309 (14)	0.0024 (14)
O11	0.0589 (17)	0.0320 (14)	0.0433 (16)	−0.0047 (12)	0.0251 (13)	0.0049 (11)

Geometric parameters (Å, º) top

Na1—O1	2.312 (2)	P2—O5	1.5188 (19)
Na1—O7	2.316 (2)	P2—Na1ⁱⁱ	3.3014 (15)
Na1—O5ⁱ	2.348 (2)	C2—H2D	0.96
Na1—O4ⁱ	2.414 (3)	C2—H2E	0.96
Na1—O3ⁱ	2.553 (2)	C2—H2F	0.96
Na1—O8ⁱ	2.864 (3)	O3—Na1ⁱⁱ	2.553 (2)
Na1—C1ⁱ	3.122 (3)	O4—Na1ⁱⁱ	2.414 (3)
Na1—Na2ⁱ	3.2336 (17)	O4—H4	0.86 (4)
Na1—P2ⁱ	3.3014 (15)	O5—Na1ⁱⁱ	2.348 (2)
Na1—P1ⁱ	3.3511 (15)	N1—C3	1.477 (4)
Na1—P1	3.4418 (15)	N1—H1A	0.89 (4)
Na1—Na2	4.0718 (19)	N1—H1B	0.89 (4)
Na2—O10	2.269 (3)	N1—H1C	0.92 (3)
Na2—O9	2.351 (2)	N2—C4	1.485 (4)
Na2—O5	2.386 (2)	N2—H2A	0.91 (4)
Na2—O8	2.399 (3)	N2—H2B	0.90 (3)
Na2—O3	2.418 (2)	N2—H2C	0.89 (4)
Na2—O7	2.706 (3)	C3—C4	1.521 (4)
Na2—P2	3.0000 (17)	C3—H3A	0.97
Na2—Na1ⁱⁱ	3.2336 (17)	C3—H3B	0.97
Na2—H9A	2.25 (3)	C4—H4A	0.97
P1—O3	1.5219 (19)	C4—H4B	0.97
P1—O2	1.5231 (19)	O8—Na1ⁱⁱ	2.864 (3)
P1—O1	1.5247 (19)	O8—H8A	0.850 (10)
P1—C1	1.855 (3)	O8—H8B	0.853 (10)
P1—Na1ⁱⁱ	3.3511 (15)	O9—H9A	0.85 (3)
C1—O4	1.452 (3)	O9—H9B	0.86 (3)
C1—C2	1.522 (4)	O10—H10A	0.84 (3)
C1—P2	1.862 (3)	O10—H10B	0.85 (3)
C1—Na1ⁱⁱ	3.122 (3)	O11—H11A	0.851 (10)
P2—O6	1.514 (2)	O11—H11B	0.86 (3)
P2—O7	1.518 (2)

O1—Na1—O7	87.25 (8)	O9—Na2—H9A	21.1 (7)
O1—Na1—O5ⁱ	174.92 (10)	O5—Na2—H9A	129.2 (4)
O7—Na1—O5ⁱ	94.54 (8)	O8—Na2—H9A	97.2 (10)
O1—Na1—O4ⁱ	101.46 (8)	O3—Na2—H9A	49.5 (7)
O7—Na1—O4ⁱ	116.74 (10)	O7—Na2—H9A	98.6 (10)
O5ⁱ—Na1—O4ⁱ	73.49 (8)	P2—Na2—H9A	109.6 (8)
O1—Na1—O3ⁱ	99.94 (7)	Na1ⁱⁱ—Na2—H9A	98.0 (4)
O7—Na1—O3ⁱ	162.58 (9)	Na1—Na2—H9A	67.7 (10)
O5ⁱ—Na1—O3ⁱ	79.67 (7)	O3—P1—O2	112.43 (11)
O4ⁱ—Na1—O3ⁱ	77.61 (7)	O3—P1—O1	112.36 (11)
O1—Na1—O8ⁱ	103.20 (8)	O2—P1—O1	110.82 (11)
O7—Na1—O8ⁱ	88.99 (9)	O3—P1—C1	105.93 (11)
O5ⁱ—Na1—O8ⁱ	81.61 (8)	O2—P1—C1	105.97 (12)
O4ⁱ—Na1—O8ⁱ	144.99 (8)	O1—P1—C1	108.95 (11)
O3ⁱ—Na1—O8ⁱ	73.96 (7)	O3—P1—Na1ⁱⁱ	46.44 (8)
O1—Na1—C1ⁱ	117.50 (8)	O2—P1—Na1ⁱⁱ	100.06 (8)
O7—Na1—C1ⁱ	134.08 (10)	O1—P1—Na1ⁱⁱ	148.47 (8)
O5ⁱ—Na1—C1ⁱ	58.07 (7)	C1—P1—Na1ⁱⁱ	66.67 (8)
O4ⁱ—Na1—C1ⁱ	26.69 (7)	O3—P1—Na1	104.74 (8)
O3ⁱ—Na1—C1ⁱ	55.81 (7)	O2—P1—Na1	137.76 (8)
O8ⁱ—Na1—C1ⁱ	118.33 (7)	C1—P1—Na1	81.49 (8)
O1—Na1—Na2ⁱ	135.46 (7)	Na1ⁱⁱ—P1—Na1	120.33 (4)
O7—Na1—Na2ⁱ	117.05 (7)	P1—O1—Na1	126.35 (11)
O5ⁱ—Na1—Na2ⁱ	47.41 (6)	O4—C1—C2	111.7 (2)
O4ⁱ—Na1—Na2ⁱ	99.42 (6)	O4—C1—P1	107.07 (17)
O3ⁱ—Na1—Na2ⁱ	47.63 (5)	C2—C1—P1	110.14 (18)
O8ⁱ—Na1—Na2ⁱ	45.84 (5)	O4—C1—P2	102.90 (16)
C1ⁱ—Na1—Na2ⁱ	73.15 (6)	C2—C1—P2	110.51 (19)
O1—Na1—P2ⁱ	150.96 (7)	P1—C1—P2	114.33 (14)
O7—Na1—P2ⁱ	112.85 (7)	O4—C1—Na1ⁱⁱ	48.33 (12)
O5ⁱ—Na1—P2ⁱ	24.52 (5)	C2—C1—Na1ⁱⁱ	160.01 (19)
O4ⁱ—Na1—P2ⁱ	51.40 (5)	P1—C1—Na1ⁱⁱ	80.27 (9)
O3ⁱ—Na1—P2ⁱ	67.21 (5)	P2—C1—Na1ⁱⁱ	78.51 (9)
O8ⁱ—Na1—P2ⁱ	98.09 (6)	O6—P2—O7	113.40 (15)
C1ⁱ—Na1—P2ⁱ	33.56 (5)	O6—P2—O5	112.44 (13)
Na2ⁱ—Na1—P2ⁱ	54.64 (4)	O7—P2—O5	110.53 (14)
O1—Na1—P1ⁱ	100.93 (6)	O6—P2—C1	105.57 (12)
O7—Na1—P1ⁱ	167.12 (9)	O7—P2—C1	106.62 (11)
O5ⁱ—Na1—P1ⁱ	76.50 (5)	O5—P2—C1	107.83 (11)
O4ⁱ—Na1—P1ⁱ	52.14 (5)	O6—P2—Na2	153.90 (9)
O3ⁱ—Na1—P1ⁱ	25.59 (4)	O7—P2—Na2	64.09 (11)
O8ⁱ—Na1—P1ⁱ	98.67 (6)	O5—P2—Na2	51.97 (8)
C1ⁱ—Na1—P1ⁱ	33.06 (5)	C1—P2—Na2	99.71 (9)
Na2ⁱ—Na1—P1ⁱ	63.49 (4)	O6—P2—Na1ⁱⁱ	122.86 (11)
P2ⁱ—Na1—P1ⁱ	56.00 (3)	O7—P2—Na1ⁱⁱ	122.96 (11)
O1—Na1—P1	20.90 (5)	C1—P2—Na1ⁱⁱ	67.93 (8)
O7—Na1—P1	66.73 (6)	Na2—P2—Na1ⁱⁱ	61.53 (3)
O5ⁱ—Na1—P1	159.40 (6)	C1—C2—H2D	109.5
O4ⁱ—Na1—P1	106.42 (6)	C1—C2—H2E	109.5
O3ⁱ—Na1—P1	120.74 (6)	H2D—C2—H2E	109.5
O8ⁱ—Na1—P1	105.50 (6)	C1—C2—H2F	109.5
C1ⁱ—Na1—P1	129.05 (6)	H2D—C2—H2F	109.5
Na2ⁱ—Na1—P1	148.25 (5)	H2E—C2—H2F	109.5
P2ⁱ—Na1—P1	156.35 (5)	P1—O3—Na2	121.54 (10)
P1ⁱ—Na1—P1	120.33 (4)	P1—O3—Na1ⁱⁱ	107.97 (10)
O1—Na1—Na2	67.69 (6)	Na2—O3—Na1ⁱⁱ	81.11 (7)
O7—Na1—Na2	39.19 (7)	C1—O4—Na1ⁱⁱ	104.98 (16)
O5ⁱ—Na1—Na2	116.48 (6)	C1—O4—H4	109 (2)
O4ⁱ—Na1—Na2	150.93 (6)	Na1ⁱⁱ—O4—H4	127 (2)
O3ⁱ—Na1—Na2	129.73 (7)	P2—O5—Na1ⁱⁱ	115.58 (10)
O8ⁱ—Na1—Na2	63.17 (5)	P2—O5—Na2	97.93 (10)
C1ⁱ—Na1—Na2	172.80 (6)	Na1ⁱⁱ—O5—Na2	86.16 (8)
Na2ⁱ—Na1—Na2	106.98 (5)	P2—O7—Na1	132.63 (12)
P2ⁱ—Na1—Na2	140.81 (4)	P2—O7—Na2	85.61 (10)
P1ⁱ—Na1—Na2	153.56 (4)	Na1—O7—Na2	108.08 (10)
P1—Na1—Na2	54.16 (3)	C3—N1—H1A	106 (2)
O10—Na2—O9	102.81 (11)	C3—N1—H1B	113 (2)
O10—Na2—O5	105.29 (11)	H1A—N1—H1B	113 (3)
O9—Na2—O5	147.84 (9)	C3—N1—H1C	109 (2)
O10—Na2—O8	93.80 (10)	H1A—N1—H1C	101 (3)
O9—Na2—O8	101.95 (10)	H1B—N1—H1C	112 (3)
O5—Na2—O8	91.53 (9)	C4—N2—H2A	111 (2)
O10—Na2—O3	172.96 (11)	C4—N2—H2B	110 (2)
O9—Na2—O3	70.58 (8)	H2A—N2—H2B	114 (3)
O5—Na2—O3	81.73 (7)	C4—N2—H2C	115 (2)
O8—Na2—O3	85.44 (8)	H2A—N2—H2C	102 (3)
O10—Na2—O7	98.96 (10)	H2B—N2—H2C	105 (3)
O9—Na2—O7	102.18 (9)	N1—C3—C4	111.6 (2)
O5—Na2—O7	58.28 (7)	N1—C3—H3A	109.3
O8—Na2—O7	149.36 (9)	C4—C3—H3A	109.3
O3—Na2—O7	85.06 (7)	N1—C3—H3B	109.3
O10—Na2—P2	112.13 (10)	C4—C3—H3B	109.3
O9—Na2—P2	122.32 (8)	H3A—C3—H3B	108.0
O5—Na2—P2	30.09 (5)	N2—C4—C3	109.7 (2)
O8—Na2—P2	119.14 (8)	N2—C4—H4A	109.7
O3—Na2—P2	74.16 (6)	C3—C4—H4A	109.7
O7—Na2—P2	30.30 (5)	N2—C4—H4B	109.7
O10—Na2—Na1ⁱⁱ	133.73 (8)	C3—C4—H4B	109.7
O9—Na2—Na1ⁱⁱ	118.14 (8)	H4A—C4—H4B	108.2
O5—Na2—Na1ⁱⁱ	46.43 (5)	Na2—O8—Na1ⁱⁱ	75.23 (8)
O8—Na2—Na1ⁱⁱ	58.93 (7)	Na2—O8—H8A	143 (2)
O3—Na2—Na1ⁱⁱ	51.26 (5)	Na1ⁱⁱ—O8—H8A	78 (3)
O7—Na2—Na1ⁱⁱ	92.87 (6)	Na2—O8—H8B	106 (2)
P2—Na2—Na1ⁱⁱ	63.83 (4)	Na1ⁱⁱ—O8—H8B	124 (3)
O10—Na2—Na1	106.86 (7)	H8A—O8—H8B	109.8 (17)
O9—Na2—Na1	69.47 (7)	Na2—O9—H9A	72 (2)
O5—Na2—Na1	87.53 (6)	Na2—O9—H9B	162 (3)
O8—Na2—Na1	158.82 (8)	H9A—O9—H9B	110.7 (17)
O3—Na2—Na1	73.48 (5)	Na2—O10—H10A	117 (3)
O7—Na2—Na1	32.74 (5)	Na2—O10—H10B	129 (3)
P2—Na2—Na1	57.44 (3)	H10A—O10—H10B	113 (4)
Na1ⁱⁱ—Na2—Na1	106.98 (5)	H11A—O11—H11B	109.8 (17)
O10—Na2—H9A	123.8 (7)

O1—Na1—Na2—O10	−164.90 (11)	Na1—P1—C1—P2	55.78 (12)
O7—Na1—Na2—O10	80.18 (13)	O3—P1—C1—Na1ⁱⁱ	25.37 (10)
O5ⁱ—Na1—Na2—O10	18.29 (13)	O2—P1—C1—Na1ⁱⁱ	−94.27 (9)
O4ⁱ—Na1—Na2—O10	122.34 (16)	O1—P1—C1—Na1ⁱⁱ	146.45 (9)
O3ⁱ—Na1—Na2—O10	−80.55 (12)	Na1—P1—C1—Na1ⁱⁱ	128.36 (6)
O8ⁱ—Na1—Na2—O10	−45.94 (11)	O4—C1—P2—O6	77.6 (2)
Na2ⁱ—Na1—Na2—O10	−32.03 (11)	C2—C1—P2—O6	−41.7 (2)
P2ⁱ—Na1—Na2—O10	22.30 (12)	P1—C1—P2—O6	−166.68 (15)
P1ⁱ—Na1—Na2—O10	−96.31 (13)	Na1ⁱⁱ—C1—P2—O6	119.66 (12)
P1—Na1—Na2—O10	176.76 (10)	O4—C1—P2—O7	−161.51 (18)
O1—Na1—Na2—O9	−67.21 (9)	C2—C1—P2—O7	79.1 (2)
O7—Na1—Na2—O9	177.87 (11)	P1—C1—P2—O7	−45.79 (18)
O5ⁱ—Na1—Na2—O9	115.98 (10)	Na1ⁱⁱ—C1—P2—O7	−119.45 (12)
O4ⁱ—Na1—Na2—O9	−139.96 (15)	O4—C1—P2—O5	−42.8 (2)
O3ⁱ—Na1—Na2—O9	17.14 (10)	C2—C1—P2—O5	−162.14 (19)
O8ⁱ—Na1—Na2—O9	51.76 (9)	P1—C1—P2—O5	72.93 (16)
Na2ⁱ—Na1—Na2—O9	65.66 (8)	Na1ⁱⁱ—C1—P2—O5	−0.73 (11)
P2ⁱ—Na1—Na2—O9	119.99 (9)	O4—C1—P2—Na2	−95.81 (16)
P1ⁱ—Na1—Na2—O9	1.39 (11)	C2—C1—P2—Na2	144.84 (18)
P1—Na1—Na2—O9	−85.54 (7)	P1—C1—P2—Na2	19.91 (14)
O1—Na1—Na2—O5	89.87 (8)	Na1ⁱⁱ—C1—P2—Na2	−53.76 (5)
O7—Na1—Na2—O5	−25.05 (9)	O4—C1—P2—Na1ⁱⁱ	−42.05 (14)
O5ⁱ—Na1—Na2—O5	−86.94 (9)	C2—C1—P2—Na1ⁱⁱ	−161.4 (2)
O4ⁱ—Na1—Na2—O5	17.11 (15)	P1—C1—P2—Na1ⁱⁱ	73.67 (12)
O3ⁱ—Na1—Na2—O5	174.22 (8)	O10—Na2—P2—O6	21.9 (3)
O8ⁱ—Na1—Na2—O5	−151.17 (8)	O9—Na2—P2—O6	144.7 (3)
Na2ⁱ—Na1—Na2—O5	−137.27 (6)	O5—Na2—P2—O6	−60.4 (3)
P2ⁱ—Na1—Na2—O5	−82.93 (8)	O8—Na2—P2—O6	−86.0 (3)
P1ⁱ—Na1—Na2—O5	158.46 (9)	O3—Na2—P2—O6	−161.4 (3)
P1—Na1—Na2—O5	71.53 (6)	O7—Na2—P2—O6	90.7 (3)
O1—Na1—Na2—O8	2.0 (2)	Na1ⁱⁱ—Na2—P2—O6	−107.2 (3)
O7—Na1—Na2—O8	−112.9 (2)	Na1—Na2—P2—O6	118.4 (3)
O5ⁱ—Na1—Na2—O8	−174.8 (2)	O10—Na2—P2—O7	−68.73 (11)
O4ⁱ—Na1—Na2—O8	−70.7 (3)	O9—Na2—P2—O7	53.99 (12)
O3ⁱ—Na1—Na2—O8	86.4 (2)	O5—Na2—P2—O7	−151.03 (13)
O8ⁱ—Na1—Na2—O8	121.0 (3)	O8—Na2—P2—O7	−176.71 (11)
Na2ⁱ—Na1—Na2—O8	134.9 (2)	O3—Na2—P2—O7	107.93 (10)
P2ⁱ—Na1—Na2—O8	−170.8 (2)	Na1ⁱⁱ—Na2—P2—O7	162.10 (9)
P1ⁱ—Na1—Na2—O8	70.6 (3)	Na1—Na2—P2—O7	27.69 (8)
P1—Na1—Na2—O8	−16.3 (2)	O10—Na2—P2—O5	82.30 (12)
O1—Na1—Na2—O3	7.76 (7)	O9—Na2—P2—O5	−154.98 (13)
O7—Na1—Na2—O3	−107.16 (10)	O8—Na2—P2—O5	−25.68 (11)
O5ⁱ—Na1—Na2—O3	−169.05 (9)	O3—Na2—P2—O5	−101.03 (11)
O4ⁱ—Na1—Na2—O3	−64.99 (15)	O7—Na2—P2—O5	151.03 (13)
O3ⁱ—Na1—Na2—O3	92.11 (9)	Na1ⁱⁱ—Na2—P2—O5	−46.87 (9)
O8ⁱ—Na1—Na2—O3	126.73 (8)	Na1—Na2—P2—O5	178.72 (10)
Na2ⁱ—Na1—Na2—O3	140.63 (6)	O10—Na2—P2—C1	−172.59 (11)
P2ⁱ—Na1—Na2—O3	−165.04 (8)	O9—Na2—P2—C1	−49.87 (11)
P1ⁱ—Na1—Na2—O3	76.36 (10)	O5—Na2—P2—C1	105.11 (12)
P1—Na1—Na2—O3	−10.57 (5)	O8—Na2—P2—C1	79.43 (11)
O1—Na1—Na2—O7	114.92 (10)	O3—Na2—P2—C1	4.07 (9)
O5ⁱ—Na1—Na2—O7	−61.89 (11)	O7—Na2—P2—C1	−103.86 (12)
O4ⁱ—Na1—Na2—O7	42.16 (15)	Na1ⁱⁱ—Na2—P2—C1	58.24 (8)
O3ⁱ—Na1—Na2—O7	−160.73 (11)	Na1—Na2—P2—C1	−76.17 (8)
O8ⁱ—Na1—Na2—O7	−126.12 (10)	O10—Na2—P2—Na1ⁱⁱ	129.17 (8)
Na2ⁱ—Na1—Na2—O7	−112.21 (9)	O9—Na2—P2—Na1ⁱⁱ	−108.11 (9)
P2ⁱ—Na1—Na2—O7	−57.88 (10)	O5—Na2—P2—Na1ⁱⁱ	46.87 (9)
P1ⁱ—Na1—Na2—O7	−176.49 (13)	O8—Na2—P2—Na1ⁱⁱ	21.19 (8)
P1—Na1—Na2—O7	96.59 (9)	O3—Na2—P2—Na1ⁱⁱ	−54.17 (5)
O1—Na1—Na2—P2	89.23 (6)	O7—Na2—P2—Na1ⁱⁱ	−162.10 (9)
O7—Na1—Na2—P2	−25.69 (8)	Na1—Na2—P2—Na1ⁱⁱ	−134.41 (5)
O5ⁱ—Na1—Na2—P2	−87.58 (8)	O2—P1—O3—Na2	172.90 (11)
O4ⁱ—Na1—Na2—P2	16.47 (13)	O1—P1—O3—Na2	−61.25 (14)
O3ⁱ—Na1—Na2—P2	173.58 (8)	C1—P1—O3—Na2	57.60 (14)
O8ⁱ—Na1—Na2—P2	−151.81 (7)	Na1ⁱⁱ—P1—O3—Na2	90.48 (12)
Na2ⁱ—Na1—Na2—P2	−137.91 (4)	Na1—P1—O3—Na2	−27.57 (12)
P2ⁱ—Na1—Na2—P2	−83.57 (7)	O2—P1—O3—Na1ⁱⁱ	82.42 (12)
P1ⁱ—Na1—Na2—P2	157.82 (9)	O1—P1—O3—Na1ⁱⁱ	−151.74 (9)
P1—Na1—Na2—P2	70.89 (3)	C1—P1—O3—Na1ⁱⁱ	−32.88 (12)
O1—Na1—Na2—Na1ⁱⁱ	47.13 (7)	Na1—P1—O3—Na1ⁱⁱ	−118.06 (7)
O7—Na1—Na2—Na1ⁱⁱ	−67.79 (9)	O9—Na2—O3—P1	96.78 (14)
O5ⁱ—Na1—Na2—Na1ⁱⁱ	−129.67 (7)	O5—Na2—O3—P1	−66.62 (12)
O4ⁱ—Na1—Na2—Na1ⁱⁱ	−25.62 (16)	O8—Na2—O3—P1	−158.83 (14)
O3ⁱ—Na1—Na2—Na1ⁱⁱ	131.49 (7)	O7—Na2—O3—P1	−7.99 (12)
O8ⁱ—Na1—Na2—Na1ⁱⁱ	166.10 (7)	P2—Na2—O3—P1	−36.80 (11)
Na2ⁱ—Na1—Na2—Na1ⁱⁱ	180.0	Na1ⁱⁱ—Na2—O3—P1	−105.69 (13)
P2ⁱ—Na1—Na2—Na1ⁱⁱ	−125.67 (5)	Na1—Na2—O3—P1	23.25 (11)
P1ⁱ—Na1—Na2—Na1ⁱⁱ	115.73 (8)	O9—Na2—O3—Na1ⁱⁱ	−157.53 (9)
P1—Na1—Na2—Na1ⁱⁱ	28.80 (4)	O5—Na2—O3—Na1ⁱⁱ	39.07 (6)
O1—Na1—P1—O3	−108.55 (16)	O8—Na2—O3—Na1ⁱⁱ	−53.15 (8)
O7—Na1—P1—O3	59.90 (11)	O7—Na2—O3—Na1ⁱⁱ	97.69 (7)
O5ⁱ—Na1—P1—O3	85.8 (2)	P2—Na2—O3—Na1ⁱⁱ	68.89 (5)
O4ⁱ—Na1—P1—O3	172.47 (9)	Na1—Na2—O3—Na1ⁱⁱ	128.93 (7)
O3ⁱ—Na1—P1—O3	−102.40 (11)	C2—C1—O4—Na1ⁱⁱ	−179.98 (18)
O8ⁱ—Na1—P1—O3	−22.10 (10)	P1—C1—O4—Na1ⁱⁱ	−59.34 (16)
C1ⁱ—Na1—P1—O3	−171.33 (10)	P2—C1—O4—Na1ⁱⁱ	61.49 (16)
Na2ⁱ—Na1—P1—O3	−44.33 (11)	O6—P2—O5—Na1ⁱⁱ	−114.91 (14)
P2ⁱ—Na1—P1—O3	154.02 (11)	O7—P2—O5—Na1ⁱⁱ	117.25 (12)
P1ⁱ—Na1—P1—O3	−132.20 (8)	C1—P2—O5—Na1ⁱⁱ	1.06 (15)
Na2—Na1—P1—O3	16.80 (8)	Na2—P2—O5—Na1ⁱⁱ	89.53 (12)
O1—Na1—P1—O2	42.71 (19)	O6—P2—O5—Na2	155.56 (11)
O7—Na1—P1—O2	−148.85 (15)	O7—P2—O5—Na2	27.72 (13)
O5ⁱ—Na1—P1—O2	−122.9 (2)	C1—P2—O5—Na2	−88.47 (11)
O4ⁱ—Na1—P1—O2	−36.27 (14)	Na1ⁱⁱ—P2—O5—Na2	−89.53 (12)
O3ⁱ—Na1—P1—O2	48.86 (15)	O10—Na2—O5—P2	−107.89 (10)
O8ⁱ—Na1—P1—O2	129.15 (13)	O9—Na2—O5—P2	42.2 (2)
C1ⁱ—Na1—P1—O2	−20.07 (16)	O8—Na2—O5—P2	157.75 (10)
Na2ⁱ—Na1—P1—O2	106.93 (14)	O3—Na2—O5—P2	72.59 (9)
P2ⁱ—Na1—P1—O2	−54.73 (17)	O7—Na2—O5—P2	−16.69 (8)
P1ⁱ—Na1—P1—O2	19.06 (15)	Na1ⁱⁱ—Na2—O5—P2	115.31 (11)
Na2—Na1—P1—O2	168.05 (13)	Na1—Na2—O5—P2	−1.08 (8)
O7—Na1—P1—O1	168.45 (17)	O10—Na2—O5—Na1ⁱⁱ	136.80 (9)
O5ⁱ—Na1—P1—O1	−165.7 (3)	O9—Na2—O5—Na1ⁱⁱ	−73.13 (17)
O4ⁱ—Na1—P1—O1	−78.98 (15)	O8—Na2—O5—Na1ⁱⁱ	42.44 (8)
O3ⁱ—Na1—P1—O1	6.15 (15)	O3—Na2—O5—Na1ⁱⁱ	−42.72 (7)
O8ⁱ—Na1—P1—O1	86.44 (15)	O7—Na2—O5—Na1ⁱⁱ	−132.00 (8)
C1ⁱ—Na1—P1—O1	−62.78 (16)	P2—Na2—O5—Na1ⁱⁱ	−115.31 (11)
Na2ⁱ—Na1—P1—O1	64.22 (16)	Na1—Na2—O5—Na1ⁱⁱ	−116.39 (6)
P2ⁱ—Na1—P1—O1	−97.43 (17)	O6—P2—O7—Na1	98.0 (2)
P1ⁱ—Na1—P1—O1	−23.65 (14)	O5—P2—O7—Na1	−134.67 (18)
Na2—Na1—P1—O1	125.35 (15)	C1—P2—O7—Na1	−17.7 (2)
O1—Na1—P1—C1	147.12 (17)	Na2—P2—O7—Na1	−110.6 (2)
O7—Na1—P1—C1	−44.44 (11)	Na1ⁱⁱ—P2—O7—Na1	−91.8 (2)
O5ⁱ—Na1—P1—C1	−18.5 (2)	O6—P2—O7—Na2	−151.35 (11)
O4ⁱ—Na1—P1—C1	68.14 (10)	O5—P2—O7—Na2	−24.04 (11)
O3ⁱ—Na1—P1—C1	153.27 (11)	C1—P2—O7—Na2	92.90 (10)
O8ⁱ—Na1—P1—C1	−126.44 (10)	Na1ⁱⁱ—P2—O7—Na2	18.79 (9)
C1ⁱ—Na1—P1—C1	84.34 (11)	O1—Na1—O7—P2	43.9 (2)
Na2ⁱ—Na1—P1—C1	−148.66 (11)	O5ⁱ—Na1—O7—P2	−131.35 (19)
P2ⁱ—Na1—P1—C1	49.68 (13)	O4ⁱ—Na1—O7—P2	−57.6 (2)
P1ⁱ—Na1—P1—C1	123.47 (9)	O3ⁱ—Na1—O7—P2	159.0 (2)
Na2—Na1—P1—C1	−87.54 (9)	O8ⁱ—Na1—O7—P2	147.1 (2)
O1—Na1—P1—Na1ⁱⁱ	−156.35 (14)	C1ⁱ—Na1—O7—P2	−82.8 (2)
O7—Na1—P1—Na1ⁱⁱ	12.10 (10)	Na2ⁱ—Na1—O7—P2	−175.16 (16)
O5ⁱ—Na1—P1—Na1ⁱⁱ	38.0 (2)	P2ⁱ—Na1—O7—P2	−114.49 (18)
O4ⁱ—Na1—P1—Na1ⁱⁱ	124.67 (6)	P1ⁱ—Na1—O7—P2	−86.0 (3)
O3ⁱ—Na1—P1—Na1ⁱⁱ	−150.20 (5)	P1—Na1—O7—P2	39.78 (18)
O8ⁱ—Na1—P1—Na1ⁱⁱ	−69.91 (8)	Na2—Na1—O7—P2	101.0 (2)
C1ⁱ—Na1—P1—Na1ⁱⁱ	140.87 (7)	O1—Na1—O7—Na2	−57.13 (9)
Na2ⁱ—Na1—P1—Na1ⁱⁱ	−92.13 (9)	O5ⁱ—Na1—O7—Na2	127.63 (9)
P2ⁱ—Na1—P1—Na1ⁱⁱ	106.22 (9)	O4ⁱ—Na1—O7—Na2	−158.58 (8)
P1ⁱ—Na1—P1—Na1ⁱⁱ	180.0	O3ⁱ—Na1—O7—Na2	58.0 (3)
Na2—Na1—P1—Na1ⁱⁱ	−31.00 (5)	O8ⁱ—Na1—O7—Na2	46.13 (8)
O3—P1—O1—Na1	82.48 (15)	C1ⁱ—Na1—O7—Na2	176.21 (9)
O2—P1—O1—Na1	−150.80 (13)	Na2ⁱ—Na1—O7—Na2	83.83 (9)
C1—P1—O1—Na1	−34.59 (17)	P2ⁱ—Na1—O7—Na2	144.49 (6)
Na1ⁱⁱ—P1—O1—Na1	41.5 (2)	P1ⁱ—Na1—O7—Na2	173.0 (3)
O7—Na1—O1—P1	−10.61 (15)	P1—Na1—O7—Na2	−61.24 (6)
O4ⁱ—Na1—O1—P1	106.12 (14)	O10—Na2—O7—P2	119.08 (11)
O3ⁱ—Na1—O1—P1	−174.63 (13)	O9—Na2—O7—P2	−135.63 (9)
O8ⁱ—Na1—O1—P1	−98.93 (14)	O5—Na2—O7—P2	16.59 (8)
C1ⁱ—Na1—O1—P1	128.87 (13)	O8—Na2—O7—P2	5.64 (19)
Na2ⁱ—Na1—O1—P1	−137.51 (11)	O3—Na2—O7—P2	−66.74 (9)
P2ⁱ—Na1—O1—P1	124.99 (14)	Na1ⁱⁱ—Na2—O7—P2	−16.03 (8)
P1ⁱ—Na1—O1—P1	159.35 (13)	Na1—Na2—O7—P2	−133.59 (12)
Na2—Na1—O1—P1	−45.62 (12)	O10—Na2—O7—Na1	−107.33 (11)
O3—P1—C1—O4	66.06 (19)	O9—Na2—O7—Na1	−2.04 (11)
O2—P1—C1—O4	−53.58 (19)	O5—Na2—O7—Na1	150.18 (10)
O1—P1—C1—O4	−172.86 (16)	O8—Na2—O7—Na1	139.24 (16)
Na1ⁱⁱ—P1—C1—O4	40.69 (15)	O3—Na2—O7—Na1	66.85 (9)
Na1—P1—C1—O4	169.05 (17)	P2—Na2—O7—Na1	133.59 (12)
O3—P1—C1—C2	−172.34 (19)	Na1ⁱⁱ—Na2—O7—Na1	117.56 (8)
O2—P1—C1—C2	68.0 (2)	N1—C3—C4—N2	177.6 (2)
O1—P1—C1—C2	−51.3 (2)	O10—Na2—O8—Na1ⁱⁱ	−140.24 (10)
Na1ⁱⁱ—P1—C1—C2	162.3 (2)	O9—Na2—O8—Na1ⁱⁱ	115.80 (8)
Na1—P1—C1—C2	−69.34 (18)	O5—Na2—O8—Na1ⁱⁱ	−34.81 (7)
O3—P1—C1—P2	−47.21 (16)	O3—Na2—O8—Na1ⁱⁱ	46.77 (6)
O2—P1—C1—P2	−166.84 (12)	O7—Na2—O8—Na1ⁱⁱ	−25.51 (17)
O1—P1—C1—P2	73.87 (16)	P2—Na2—O8—Na1ⁱⁱ	−22.26 (8)
Na1ⁱⁱ—P1—C1—P2	−72.58 (12)	Na1—Na2—O8—Na1ⁱⁱ	52.3 (2)

Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O7	0.92 (3)	1.80 (3)	2.689 (3)	160 (3)
O11—H11B···O1	0.86 (3)	1.99 (3)	2.804 (3)	158 (3)
N1—H1A···O5ⁱ	0.89 (3)	1.90 (3)	2.768 (3)	163 (3)
N1—H1B···O6ⁱⁱⁱ	0.89 (4)	1.98 (4)	2.850 (4)	165 (3)
N2—H2A···O2^iv	0.91 (4)	1.76 (4)	2.669 (3)	177 (3)
N2—H2B···O1^v	0.90 (3)	1.91 (3)	2.781 (3)	163 (3)
N2—H2C···O8^vi	0.89 (4)	2.54 (4)	3.199 (4)	131 (3)
O4—H4···O11^vii	0.86 (4)	1.83 (4)	2.686 (3)	172 (3)
O8—H8A···O9ⁱⁱ	0.85 (2)	2.04 (3)	2.869 (3)	165 (3)
O8—H8B···O6^viii	0.85 (2)	1.83 (2)	2.664 (3)	165 (3)
O9—H9B···O2^ix	0.86 (3)	1.80 (3)	2.653 (3)	175 (3)
O10—H10A···O6^viii	0.84 (3)	2.25 (2)	2.957 (4)	143 (3)
O10—H10B···O6ⁱⁱⁱ	0.85 (3)	2.31 (2)	3.099 (4)	155 (3)
O11—H11A···O3ⁱ	0.85 (2)	1.88 (3)	2.668 (3)	154 (3)

Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z; (iii) −x+3/2, y+1/2, z+1/2; (iv) x+1/2, −y+1/2, z; (v) x+1/2, −y+3/2, z; (vi) −x+3/2, y+1/2, z−1/2; (vii) −x+1, −y+1, z−1/2; (viii) −x+3/2, y−1/2, z+1/2; (ix) −x+1, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂H₁₀N₂²⁺·2Na⁺·C₂H₄O₇P₂⁴⁻·4H₂O
M_r	382.16
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	293
a, b, c (Å)	20.966 (7), 5.8928 (18), 11.871 (4)
V (Å³)	1466.6 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.41
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.922, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	5700, 2203, 2021
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.064, 1.06
No. of reflections	2203
No. of parameters	236
No. of restraints	13
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.31
Absolute structure	Flack (1983), 1217 Friedel pairs
Absolute structure parameter	−0.10 (10)

Computer programs: SMART (Siemens, 1996), SMART, SHELXTL (Sheldrick, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL.

Selected geometric parameters (Å, º) top

Na1—O1	2.312 (2)	P1—O2	1.5231 (19)
Na1—O7	2.316 (2)	P1—O1	1.5247 (19)
Na1—O5ⁱ	2.348 (2)	P1—C1	1.855 (3)
Na1—O4ⁱ	2.414 (3)	C1—O4	1.452 (3)
Na1—O3ⁱ	2.553 (2)	C1—C2	1.522 (4)
Na2—O10	2.269 (3)	C1—P2	1.862 (3)
Na2—O9	2.351 (2)	P2—O6	1.514 (2)
Na2—O5	2.386 (2)	P2—O7	1.518 (2)
Na2—O8	2.399 (3)	P2—O5	1.5188 (19)
Na2—O3	2.418 (2)	N1—C3	1.477 (4)
Na2—O7	2.706 (3)	N2—C4	1.485 (4)
P1—O3	1.5219 (19)	C3—C4	1.521 (4)

O3—P1—O2	112.43 (11)	O4—C1—P2	102.90 (16)
O3—P1—O1	112.36 (11)	C2—C1—P2	110.51 (19)
O2—P1—O1	110.82 (11)	P1—C1—P2	114.33 (14)
O3—P1—C1	105.93 (11)	O6—P2—O7	113.40 (15)
O2—P1—C1	105.97 (12)	O6—P2—O5	112.44 (13)
O1—P1—C1	108.95 (11)	O7—P2—O5	110.53 (14)
O4—C1—C2	111.7 (2)	O6—P2—C1	105.57 (12)
O4—C1—P1	107.07 (17)	O7—P2—C1	106.62 (11)
C2—C1—P1	110.14 (18)	O5—P2—C1	107.83 (11)

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