Poly[μ2-aqua-diaqua­(μ8-3-nitro­benzene-1,2-dicarboxylato)(μ6-3-nitro­benzene-1,2-dicarboxylato)tetra­sodium]

Shuai, Q.; Di, Y.-Y.; Li, Z.-B.; Li, L.; He, D.-H.

doi:10.1107/S1600536810044600

Poly[μ₂-aqua-diaqua(μ₈-3-nitrobenzene-1,2-dicarboxylato)(μ₆-3-nitrobenzene-1,2-dicarboxylato)tetrasodium]

Q. Shuai, Y.-Y. Di, Z.-B. Li, L. Li and D.-H. He

In the title layered coordination polymer, [Na₄(C₈H₃NO₆)₂(H₂O)₃]_n, the doubly deprotonated 3-nitrobenzene-1,2-dicarboxylate ligands exhibit μ₈- and μ₆-coordination modes to the sodium ions, generating sheets lying parallel to (001). The coordination environments of the sodium ions are distorted octahedral, distorted trigonal-bipyramidal and moncapped trigonal-prismatic. One of the nitro groups is disordered over two sets of sites with site-occupancy factors 0.580 (8):0.419 (2). A network of O—H

O and O—H

N hydrogen bonds helps to establish the packing.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810044600/hb5692sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536810044600/hb5692Isup2.hkl Contains datablock I

CCDC reference: 802951

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.008 Å
Disorder in main residue
R factor = 0.065
wR factor = 0.208
Data-to-parameter ratio = 10.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       3.89 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        O10
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Na3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT314_ALERT_2_C Check Small Angle for H2O: Metal-O15    -H15B         91.78 Deg.
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds (x 1000) Ang ..          8
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C2     -   C4     ...       1.53 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C10    -   C12    ...       1.53 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          4
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.595         61
PLAT480_ALERT_4_C Long H...A H-Bond Reported H13B   ..  O9      ..       2.63 Ang.

Alert level G
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT Unusually Large.       0.12
PLAT301_ALERT_3_G Note: Main Residue  Disorder ...................       3.00 Perc.
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......        162
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        108
            O11 -NA3 -O7  -C9    -16.00  3.00   1.565   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        172
            O10 -NA4 -C2  -C4     64.00  2.00   1.565   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        173
            O1  -NA4 -C2  -C4    168.00  2.00   2.666   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        174
            O15 -NA4 -C2  -C4    -28.00  2.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        175
            O3  -NA4 -C2  -C4     82.00  2.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        176
            O2  -NA4 -C2  -C4    177.00  2.00   2.666   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        177
            O4  -NA4 -C2  -C4   -107.00  2.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        178
            O9  -NA4 -C2  -C4    -89.00  2.00   1.665   1.555   1.555   1.555
PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) .       1.24 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
  12 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
  10 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Ming Ling Guo has obtained one kind of sodium complex {[Na(C₈H₄NO₆)(H₂O)₃].H₂O}_n (Guo, 2004) based on 3-Nitrobenzene-1,2-dicarboxylic acid ligand.

Here we report another kind of sodium complex (I) based on the same ligand. Different from {[Na(C₈H₄NO₆)(H₂O)₃].H₂O}_n, the formula for the title complex is [Na₄(C₈H₃NO₆)₂(H₂O)₃]_n. X-ray single-crystal diffraction analysis indicates the presence of four independent Na^I ions, two 3-Nitrobenzene-1,2-dicarboxylato and three coordinated water molecules in the asymmetric unit. Only one independent Na^I ion can be found in complex of {[Na(C₈H₄NO₆)(H₂O)₃].H₂O}_n. Moreover, the ligand in the title complex is completely deprotonated, which is different from the uncomplete form in complex of {[Na(C₈H₄NO₆)(H₂O)₃].H₂O}_n.

In the title complex, the coordination geometry (Fig. 1) around Na1^I and Na2^I ions could be described as distorted octahedral arrangements with coordination number of 6, all the coordinated atoms are oxygen atoms. For Na1^I center, all the six oxygen atoms come from carboxylate groups. For Na2^I center, four oxygen atoms come from carboxylate groups, two of them come from coordinated water molecules. The coordination numbers of Na3^I and Na4^I ions are 5 and 7, and the geometries around them could be described as distorted trigonal bipyramid and moncapped octahedron prism arrangements. Around Na3^I center, three oxygen atoms come from carboxylate groups, one is nitro oxygen atom, and the last comes from coordinated water molecule. Concerning Na4^I center, six of the oxygen atoms belong to carboxylate groups and only one oxygen atom is from coordinated water molecule. 3-Nitrobenzene-1,2-dicarboxylic acid ligands exhibit two coordination modes (Fig. 2), which can be classified as µ₈-(κ¹², O¹: O¹: O¹: O²: O²: O²: O³: O³: O³: O⁴: O⁴: O⁴) and µ₆-(κ⁸, O⁷: O⁸: O⁸: O⁹: O⁹: O¹⁰: O¹⁰: O¹¹), and a two-dimensional (Fig. 3) polymeric framwork can be assembled by oxygen atoms of the ligands through the two coordination modes. We can clearly see that it is different from the complex synthesized by Ming Ling Guo, which forms polymeric chains by way of edge-sharing via pairs of water molecules between NaO(H₂O)₅ octahedra.

Related literature top

For a related structure containing the same components, see: Guo (2004).

Experimental top

A mixture of strontium chloride hexahydrate (0.0267 g, 0.1 mmol), sodium hydroxide (0.0080 g, 0.2 mmol), 3-Nitrobenzene-1,2-dicarboxylic acid (0.0211 g, 0.1 mmol), and H₂O (20 mL) was placed in a Parr Teflon-lined stainless stell vessel (25 ml), and then the vessel was sealed and heated at 443.15 K for 4 days. Then the vessel was cooled to 373.15 K at a rate of 5 K h^-1 and slowly cooled to room temperature. Colorless, block single crystals suitable for X-ray diffraction were obtained.

Structure description top

Ming Ling Guo has obtained one kind of sodium complex {[Na(C₈H₄NO₆)(H₂O)₃].H₂O}_n (Guo, 2004) based on 3-Nitrobenzene-1,2-dicarboxylic acid ligand.

For a related structure containing the same components, see: Guo (2004).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Coordination environment of Na^I ions in the title complex. Non-hydrogen atoms are shown as 30% probability ellipsoids. Hydrogen atoms are omitted for clarity. Symmetry codes: (A) -x, -y, -z + 1; (B) -x + 1, -y, -z + 1; (D) -x + 1, -y + 1, -z + 1; (E) -x + 2, -y + 1, -z + 1; (G) x - 1, y, z; (H) x, y + 1, z; (I) x + 1, y + 1, z.
	Fig. 2. Coordination modes of 3-Nitrobenzene-1,2-dicarboxylic acid ligands in the title complex. Hydrogen atoms are omitted for clarity.
	Fig. 3. View of two-dimensional framework along c axis in the title complex.

Poly[µ₂-aqua-diaqua(µ₈-3-nitrobenzene-1,2-dicarboxylato)(µ₆-3- nitrobenzene-1,2-dicarboxylato)tetrasodium] top

Crystal data top

[Na₄(C₈H₃NO₆)₂(H₂O)₃]	Z = 2
M_r = 564.24	F(000) = 572
Triclinic, P1	D_x = 1.839 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.6871 (8) Å	Cell parameters from 1631 reflections
b = 10.6193 (15) Å	θ = 2.8–28.2°
c = 14.582 (2) Å	µ = 0.23 mm⁻¹
α = 82.065 (1)°	T = 298 K
β = 83.428 (1)°	Block, colourless
γ = 89.371 (2)°	0.44 × 0.38 × 0.17 mm
V = 1018.8 (2) Å³

Data collection top

Bruker SMART CCD diffractometer	3514 independent reflections
Radiation source: fine-focus sealed tube	2272 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
phi and ω scans	θ_max = 25.0°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −7→7
T_min = 0.905, T_max = 0.962	k = −11→12
5276 measured reflections	l = −17→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.208	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.1154P)² + 0.9421P] where P = (F_o² + 2F_c²)/3
3514 reflections	(Δ/σ)_max < 0.001
344 parameters	Δρ_max = 0.76 e Å⁻³
162 restraints	Δρ_min = −0.69 e Å⁻³

Crystal data top

[Na₄(C₈H₃NO₆)₂(H₂O)₃]	γ = 89.371 (2)°
M_r = 564.24	V = 1018.8 (2) Å³
Triclinic, P1	Z = 2
a = 6.6871 (8) Å	Mo Kα radiation
b = 10.6193 (15) Å	µ = 0.23 mm⁻¹
c = 14.582 (2) Å	T = 298 K
α = 82.065 (1)°	0.44 × 0.38 × 0.17 mm
β = 83.428 (1)°

Data collection top

Bruker SMART CCD diffractometer	3514 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	2272 reflections with I > 2σ(I)
T_min = 0.905, T_max = 0.962	R_int = 0.026
5276 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	162 restraints
wR(F²) = 0.208	H-atom parameters constrained
S = 1.04	Δρ_max = 0.76 e Å⁻³
3514 reflections	Δρ_min = −0.69 e Å⁻³
344 parameters

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	Occ. (<1)
Na1	0.2359 (3)	0.00241 (17)	0.50423 (14)	0.0330 (5)
Na2	0.7386 (3)	0.50445 (17)	0.49820 (13)	0.0302 (5)
Na3	0.0578 (3)	0.5315 (2)	0.28461 (17)	0.0479 (6)
Na4	0.5016 (4)	0.7672 (2)	0.37516 (15)	0.0522 (7)
N1	0.6311 (9)	0.5233 (5)	0.1143 (3)	0.0533 (14)
N2	0.1544 (9)	−0.1646 (5)	0.1478 (4)	0.0556 (14)
O1	0.5149 (5)	0.3531 (3)	0.4692 (2)	0.0299 (8)
O2	0.5038 (5)	0.1449 (3)	0.4694 (2)	0.0335 (8)
O3	0.3758 (5)	0.5587 (3)	0.3345 (2)	0.0328 (8)
O4	0.7092 (5)	0.5666 (3)	0.3304 (2)	0.0324 (8)
O5	0.5745 (9)	0.6168 (4)	0.1406 (3)	0.0703 (13)
O6	0.645 (2)	0.5248 (9)	0.0290 (6)	0.084 (3)	0.581 (14)
O6'	0.794 (3)	0.5271 (13)	0.0538 (10)	0.085 (4)	0.419 (14)
O7	0.0464 (6)	0.3179 (4)	0.3283 (3)	0.0511 (10)
O8	0.0225 (6)	0.1255 (3)	0.4077 (3)	0.0434 (9)
O9	−0.1331 (8)	−0.1086 (4)	0.3542 (3)	0.0583 (11)
O10	0.1955 (8)	−0.1197 (4)	0.3725 (3)	0.0644 (11)
O11	0.0978 (9)	−0.2416 (5)	0.2146 (3)	0.0735 (13)
O12	0.2147 (11)	−0.1972 (6)	0.0737 (4)	0.104 (2)
O13	1.0048 (6)	0.6475 (3)	0.4843 (3)	0.0438 (10)
H13A	0.9897	0.6583	0.5414	0.053*
H13B	1.0595	0.7139	0.4526	0.053*
O14	0.0893 (12)	0.5436 (6)	0.1167 (5)	0.116 (2)
H14B	0.1713	0.5230	0.0724	0.139*
H14C	−0.0290	0.5412	0.1009	0.139*
O15	0.6276 (9)	0.8569 (5)	0.2156 (4)	0.0861 (16)
H15B	0.5852	0.7932	0.1939	0.103*
H15C	0.7525	0.8465	0.2201	0.103*
C1	0.5209 (7)	0.2562 (4)	0.4276 (3)	0.0250 (10)
C2	0.5488 (7)	0.5173 (4)	0.3145 (3)	0.0235 (10)
C3	0.5542 (7)	0.2752 (4)	0.3225 (3)	0.0256 (11)
C4	0.5689 (7)	0.3952 (4)	0.2700 (3)	0.0224 (10)
C5	0.6096 (8)	0.4004 (5)	0.1743 (3)	0.0328 (12)
C6	0.6326 (9)	0.2933 (5)	0.1290 (4)	0.0418 (14)
H6	0.6595	0.3009	0.0645	0.050*
C7	0.6145 (8)	0.1769 (5)	0.1820 (4)	0.0384 (13)
H7	0.6276	0.1036	0.1535	0.046*
C8	0.5770 (8)	0.1676 (5)	0.2771 (4)	0.0320 (12)
H8	0.5664	0.0875	0.3124	0.038*
C9	0.0500 (8)	0.1990 (5)	0.3334 (4)	0.0368 (13)
C10	0.0487 (11)	−0.0812 (5)	0.3305 (4)	0.0437 (15)
C11	0.0931 (8)	0.1445 (5)	0.2430 (4)	0.0379 (13)
C12	0.0976 (8)	0.0117 (5)	0.2412 (4)	0.0376 (13)
C13	0.1464 (9)	−0.0290 (6)	0.1550 (4)	0.0448 (14)
C14	0.1874 (10)	0.0541 (7)	0.0734 (4)	0.0580 (18)
H14A	0.2219	0.0232	0.0171	0.070*
C15	0.1767 (11)	0.1815 (7)	0.0762 (5)	0.0615 (19)
H15A	0.2003	0.2383	0.0215	0.074*
C16	0.1308 (9)	0.2257 (6)	0.1606 (5)	0.0510 (16)
H16	0.1252	0.3129	0.1621	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Na1	0.0312 (11)	0.0249 (11)	0.0412 (12)	−0.0031 (8)	−0.0024 (9)	0.0004 (9)
Na2	0.0293 (11)	0.0276 (11)	0.0333 (11)	−0.0011 (8)	−0.0008 (8)	−0.0051 (8)
Na3	0.0333 (13)	0.0374 (13)	0.0668 (16)	−0.0031 (10)	−0.0023 (11)	0.0127 (11)
Na4	0.0914 (19)	0.0293 (12)	0.0323 (12)	0.0099 (12)	0.0022 (12)	0.0002 (9)
N1	0.092 (4)	0.037 (3)	0.026 (3)	−0.010 (3)	0.010 (3)	−0.001 (2)
N2	0.070 (4)	0.059 (4)	0.038 (3)	0.009 (3)	−0.004 (3)	−0.008 (3)
O1	0.0361 (18)	0.0217 (16)	0.0308 (16)	−0.0013 (13)	−0.0004 (14)	−0.0032 (13)
O2	0.0379 (19)	0.0186 (16)	0.0406 (19)	−0.0014 (14)	−0.0009 (15)	0.0050 (14)
O3	0.0352 (18)	0.0261 (16)	0.0368 (18)	0.0034 (14)	−0.0020 (14)	−0.0061 (14)
O4	0.0358 (18)	0.0217 (16)	0.0388 (18)	−0.0050 (14)	0.0000 (14)	−0.0046 (13)
O5	0.108 (3)	0.043 (2)	0.052 (2)	0.008 (2)	0.010 (2)	0.004 (2)
O6	0.135 (7)	0.063 (5)	0.047 (5)	−0.008 (5)	0.009 (5)	−0.002 (4)
O6'	0.110 (8)	0.061 (6)	0.065 (6)	0.008 (6)	0.040 (6)	0.014 (5)
O7	0.052 (2)	0.034 (2)	0.064 (2)	0.0012 (17)	−0.0030 (19)	0.0017 (17)
O8	0.052 (2)	0.0327 (18)	0.0437 (19)	−0.0015 (16)	−0.0045 (16)	0.0015 (16)
O9	0.082 (3)	0.041 (2)	0.048 (2)	−0.010 (2)	0.006 (2)	−0.0049 (17)
O10	0.090 (3)	0.051 (2)	0.049 (2)	0.024 (2)	−0.009 (2)	−0.0013 (18)
O11	0.114 (3)	0.049 (2)	0.053 (2)	0.011 (2)	0.008 (2)	−0.004 (2)
O12	0.171 (5)	0.081 (4)	0.057 (3)	0.001 (4)	0.020 (3)	−0.025 (3)
O13	0.042 (2)	0.0249 (18)	0.062 (2)	−0.0068 (16)	0.0022 (18)	−0.0012 (17)
O14	0.143 (5)	0.094 (4)	0.099 (4)	0.000 (4)	0.020 (4)	−0.002 (3)
O15	0.088 (4)	0.057 (3)	0.111 (4)	−0.003 (3)	−0.002 (3)	−0.008 (3)
C1	0.020 (2)	0.024 (3)	0.031 (3)	0.0011 (19)	−0.0023 (19)	−0.002 (2)
C2	0.029 (3)	0.015 (2)	0.025 (2)	−0.004 (2)	0.002 (2)	−0.0002 (18)
C3	0.019 (2)	0.028 (3)	0.030 (3)	−0.001 (2)	−0.0028 (19)	−0.004 (2)
C4	0.021 (2)	0.022 (2)	0.024 (2)	−0.0027 (19)	0.0006 (19)	−0.0054 (19)
C5	0.038 (3)	0.029 (3)	0.030 (3)	−0.004 (2)	0.001 (2)	−0.003 (2)
C6	0.056 (4)	0.042 (3)	0.028 (3)	0.001 (3)	0.002 (3)	−0.011 (2)
C7	0.043 (3)	0.036 (3)	0.039 (3)	−0.002 (2)	−0.003 (3)	−0.018 (3)
C8	0.031 (3)	0.023 (3)	0.044 (3)	0.000 (2)	−0.007 (2)	−0.011 (2)
C9	0.024 (3)	0.030 (3)	0.057 (4)	−0.004 (2)	−0.006 (2)	−0.003 (3)
C10	0.069 (4)	0.029 (3)	0.033 (3)	0.014 (3)	−0.008 (3)	−0.004 (2)
C11	0.026 (3)	0.035 (3)	0.048 (3)	−0.004 (2)	−0.003 (2)	0.009 (2)
C12	0.031 (3)	0.039 (3)	0.041 (3)	0.001 (2)	−0.005 (2)	0.003 (2)
C13	0.047 (4)	0.047 (4)	0.039 (3)	0.000 (3)	−0.005 (3)	0.001 (3)
C14	0.061 (4)	0.075 (5)	0.035 (4)	−0.008 (4)	−0.005 (3)	0.004 (3)
C15	0.064 (5)	0.063 (5)	0.050 (4)	−0.018 (4)	−0.007 (3)	0.020 (3)
C16	0.044 (4)	0.045 (4)	0.059 (4)	−0.010 (3)	−0.007 (3)	0.011 (3)

Geometric parameters (Å, º) top

Na1—O2	2.323 (4)	O4—Na3^viii	2.390 (4)
Na1—O8ⁱ	2.354 (4)	O7—C9	1.255 (6)
Na1—O2ⁱⁱ	2.357 (4)	O8—C9	1.240 (7)
Na1—O8	2.374 (4)	O8—Na1ⁱ	2.354 (4)
Na1—O10	2.502 (5)	O9—C10	1.252 (8)
Na1—O9ⁱ	2.511 (5)	O9—Na1ⁱ	2.511 (5)
Na2—O1ⁱⁱⁱ	2.312 (4)	O9—Na4^ix	2.755 (6)
Na2—O1	2.320 (4)	O10—C10	1.251 (7)
Na2—O13	2.326 (4)	O10—Na4^x	2.363 (5)
Na2—O13^iv	2.353 (4)	O11—Na3^x	2.488 (5)
Na2—O3ⁱⁱⁱ	2.474 (4)	O13—Na2^iv	2.353 (4)
Na2—O4	2.475 (4)	O13—H13A	0.8498
Na3—O7	2.270 (4)	O13—H13B	0.8500
Na3—O3	2.358 (4)	O14—H14B	0.8500
Na3—O4^v	2.390 (4)	O14—H14C	0.8500
Na3—O14	2.419 (7)	O15—H15B	0.8500
Na3—O11^vi	2.488 (5)	O15—H15C	0.8500
Na4—O10^vi	2.363 (5)	C1—C3	1.509 (7)
Na4—O1ⁱⁱⁱ	2.437 (4)	C2—C4	1.526 (6)
Na4—O15	2.448 (6)	C3—C4	1.391 (7)
Na4—O3	2.546 (4)	C3—C8	1.396 (7)
Na4—O2ⁱⁱⁱ	2.563 (4)	C4—C5	1.385 (7)
Na4—O4	2.647 (4)	C5—C6	1.390 (7)
Na4—O9^vii	2.755 (6)	C6—C7	1.363 (8)
N1—O5	1.156 (6)	C6—H6	0.9300
N1—O6	1.236 (10)	C7—C8	1.371 (7)
N1—O6'	1.320 (15)	C7—H7	0.9300
N1—C5	1.466 (7)	C8—H8	0.9300
N2—O12	1.204 (7)	C9—C11	1.509 (8)
N2—O11	1.209 (7)	C10—C12	1.527 (8)
N2—C13	1.458 (8)	C11—C16	1.378 (8)
O1—C1	1.263 (6)	C11—C12	1.414 (8)
O1—Na2ⁱⁱⁱ	2.312 (4)	C12—C13	1.387 (8)
O1—Na4ⁱⁱⁱ	2.437 (4)	C13—C14	1.382 (8)
O2—C1	1.253 (6)	C14—C15	1.359 (10)
O2—Na1ⁱⁱ	2.357 (4)	C14—H14A	0.9300
O2—Na4ⁱⁱⁱ	2.563 (4)	C15—C16	1.379 (10)
O3—C2	1.250 (6)	C15—H15A	0.9300
O3—Na2ⁱⁱⁱ	2.474 (4)	C16—H16	0.9300
O4—C2	1.257 (6)

O2—Na1—O8ⁱ	159.75 (16)	C2—O4—Na2	106.5 (3)
O2—Na1—O2ⁱⁱ	82.43 (13)	Na3^viii—O4—Na2	93.63 (14)
O8ⁱ—Na1—O2ⁱⁱ	95.74 (14)	C2—O4—Na4	89.2 (3)
O2—Na1—O8	94.71 (14)	Na3^viii—O4—Na4	133.50 (16)
O8ⁱ—Na1—O8	95.73 (14)	Na2—O4—Na4	88.06 (12)
O2ⁱⁱ—Na1—O8	153.10 (16)	C9—O7—Na3	167.2 (4)
O2—Na1—O10	112.15 (17)	C9—O8—Na1ⁱ	139.0 (4)
O8ⁱ—Na1—O10	87.46 (16)	C9—O8—Na1	134.7 (4)
O2ⁱⁱ—Na1—O10	82.65 (15)	Na1ⁱ—O8—Na1	84.27 (14)
O8—Na1—O10	73.64 (15)	C10—O9—Na1ⁱ	105.9 (4)
O2—Na1—O9ⁱ	87.49 (15)	C10—O9—Na4^ix	161.6 (4)
O8ⁱ—Na1—O9ⁱ	74.31 (15)	Na1ⁱ—O9—Na4^ix	91.05 (16)
O2ⁱⁱ—Na1—O9ⁱ	111.21 (16)	C10—O10—Na4^x	149.5 (4)
O8—Na1—O9ⁱ	95.30 (16)	C10—O10—Na1	111.7 (4)
O10—Na1—O9ⁱ	157.80 (19)	Na4^x—O10—Na1	97.44 (19)
O1ⁱⁱⁱ—Na2—O1	93.04 (13)	N2—O11—Na3^x	148.5 (4)
O1ⁱⁱⁱ—Na2—O13	96.65 (14)	Na2—O13—Na2^iv	96.95 (14)
O1—Na2—O13	163.33 (16)	Na2—O13—H13A	94.9
O1ⁱⁱⁱ—Na2—O13^iv	162.13 (16)	Na2^iv—O13—H13A	94.7
O1—Na2—O13^iv	91.84 (14)	Na2—O13—H13B	144.8
O13—Na2—O13^iv	83.05 (14)	Na2^iv—O13—H13B	106.7
O1ⁱⁱⁱ—Na2—O3ⁱⁱⁱ	75.90 (13)	H13A—O13—H13B	108.4
O1—Na2—O3ⁱⁱⁱ	86.70 (13)	Na3—O14—H14B	139.6
O13—Na2—O3ⁱⁱⁱ	108.79 (15)	Na3—O14—H14C	107.4
O13^iv—Na2—O3ⁱⁱⁱ	87.24 (14)	H14B—O14—H14C	108.1
O1ⁱⁱⁱ—Na2—O4	88.52 (13)	Na4—O15—H15B	91.7
O1—Na2—O4	78.00 (12)	Na4—O15—H15C	97.8
O13—Na2—O4	88.70 (14)	H15B—O15—H15C	107.9
O13^iv—Na2—O4	109.32 (14)	O2—C1—O1	123.1 (4)
O3ⁱⁱⁱ—Na2—O4	157.58 (14)	O2—C1—C3	118.4 (4)
O7—Na3—O3	94.91 (15)	O1—C1—C3	118.4 (4)
O7—Na3—O4^v	95.67 (15)	O2—C1—Na4ⁱⁱⁱ	64.5 (3)
O3—Na3—O4^v	140.24 (16)	O1—C1—Na4ⁱⁱⁱ	58.8 (2)
O7—Na3—O14	101.1 (2)	C3—C1—Na4ⁱⁱⁱ	174.0 (3)
O3—Na3—O14	110.0 (2)	O3—C2—O4	125.2 (4)
O4^v—Na3—O14	105.3 (2)	O3—C2—C4	118.1 (4)
O7—Na3—O11^vi	171.5 (2)	O4—C2—C4	116.7 (4)
O3—Na3—O11^vi	84.59 (17)	O3—C2—Na4	60.6 (2)
O4^v—Na3—O11^vi	90.07 (16)	O4—C2—Na4	65.3 (2)
O14—Na3—O11^vi	71.2 (2)	C4—C2—Na4	172.4 (3)
O10^vi—Na4—O1ⁱⁱⁱ	105.27 (16)	O3—C2—Na2	103.5 (3)
O10^vi—Na4—O15	93.48 (18)	O4—C2—Na2	50.4 (2)
O1ⁱⁱⁱ—Na4—O15	161.21 (19)	C4—C2—Na2	114.3 (3)
O10^vi—Na4—O3	97.84 (18)	Na4—C2—Na2	72.89 (12)
O1ⁱⁱⁱ—Na4—O3	82.68 (13)	C4—C3—C8	119.3 (4)
O15—Na4—O3	96.15 (17)	C4—C3—C1	122.5 (4)
O10^vi—Na4—O2ⁱⁱⁱ	81.22 (15)	C8—C3—C1	118.2 (4)
O1ⁱⁱⁱ—Na4—O2ⁱⁱⁱ	52.44 (11)	C5—C4—C3	117.1 (4)
O15—Na4—O2ⁱⁱⁱ	131.77 (18)	C5—C4—C2	120.5 (4)
O3—Na4—O2ⁱⁱⁱ	132.08 (14)	C3—C4—C2	122.4 (4)
O10^vi—Na4—O4	147.23 (18)	C4—C5—C6	123.7 (5)
O1ⁱⁱⁱ—Na4—O4	82.10 (12)	C4—C5—N1	120.4 (4)
O15—Na4—O4	82.72 (16)	C6—C5—N1	116.0 (5)
O3—Na4—O4	50.71 (12)	C7—C6—C5	118.0 (5)
O2ⁱⁱⁱ—Na4—O4	124.99 (14)	C7—C6—H6	121.0
O10^vi—Na4—O9^vii	121.48 (18)	C5—C6—H6	121.0
O1ⁱⁱⁱ—Na4—O9^vii	103.59 (15)	C6—C7—C8	120.2 (5)
O15—Na4—O9^vii	64.33 (17)	C6—C7—H7	119.9
O3—Na4—O9^vii	135.66 (16)	C8—C7—H7	119.9
O2ⁱⁱⁱ—Na4—O9^vii	77.88 (14)	C7—C8—C3	121.7 (5)
O4—Na4—O9^vii	86.19 (14)	C7—C8—H8	119.1
O5—N1—O6	115.1 (7)	C3—C8—H8	119.1
O5—N1—O6'	118.7 (8)	O8—C9—O7	123.9 (5)
O6—N1—O6'	51.1 (8)	O8—C9—C11	119.2 (5)
O5—N1—C5	121.9 (5)	O7—C9—C11	116.9 (5)
O6—N1—C5	118.6 (6)	O10—C10—O9	127.4 (6)
O6'—N1—C5	111.5 (7)	O10—C10—C12	116.0 (6)
O12—N2—O11	121.3 (6)	O9—C10—C12	116.6 (5)
O12—N2—C13	118.4 (6)	O10—C10—Na1ⁱ	99.6 (4)
O11—N2—C13	120.3 (5)	O9—C10—Na1ⁱ	51.2 (3)
C1—O1—Na2ⁱⁱⁱ	132.4 (3)	C12—C10—Na1ⁱ	120.5 (3)
C1—O1—Na2	137.6 (3)	C16—C11—C12	119.3 (6)
Na2ⁱⁱⁱ—O1—Na2	86.96 (13)	C16—C11—C9	119.4 (5)
C1—O1—Na4ⁱⁱⁱ	94.9 (3)	C12—C11—C9	121.3 (5)
Na2ⁱⁱⁱ—O1—Na4ⁱⁱⁱ	97.15 (14)	C13—C12—C11	116.9 (5)
Na2—O1—Na4ⁱⁱⁱ	94.76 (14)	C13—C12—C10	122.3 (5)
C1—O2—Na1	133.0 (3)	C11—C12—C10	120.8 (5)
C1—O2—Na1ⁱⁱ	127.2 (3)	C14—C13—C12	122.8 (6)
Na1—O2—Na1ⁱⁱ	97.57 (13)	C14—C13—N2	117.2 (6)
C1—O2—Na4ⁱⁱⁱ	89.3 (3)	C12—C13—N2	119.9 (5)
Na1—O2—Na4ⁱⁱⁱ	100.56 (15)	C15—C14—C13	119.4 (6)
Na1ⁱⁱ—O2—Na4ⁱⁱⁱ	95.93 (14)	C15—C14—H14A	120.3
C2—O3—Na3	135.0 (3)	C13—C14—H14A	120.3
C2—O3—Na2ⁱⁱⁱ	110.4 (3)	C14—C15—C16	119.5 (6)
Na3—O3—Na2ⁱⁱⁱ	94.88 (14)	C14—C15—H15A	120.3
C2—O3—Na4	94.0 (3)	C16—C15—H15A	120.3
Na3—O3—Na4	124.18 (16)	C11—C16—C15	122.0 (6)
Na2ⁱⁱⁱ—O3—Na4	88.46 (12)	C11—C16—H16	119.0
C2—O4—Na3^viii	133.8 (3)	C15—C16—H16	119.0

O1ⁱⁱⁱ—Na2—O1—C1	160.4 (5)	Na1ⁱⁱ—O2—C1—C3	77.2 (5)
O13—Na2—O1—C1	34.9 (8)	Na4ⁱⁱⁱ—O2—C1—C3	174.1 (4)
O13^iv—Na2—O1—C1	−36.8 (5)	Na2ⁱⁱⁱ—O1—C1—O2	−99.4 (5)
O3ⁱⁱⁱ—Na2—O1—C1	−123.9 (5)	Na2—O1—C1—O2	107.5 (5)
O4—Na2—O1—C1	72.6 (5)	Na4ⁱⁱⁱ—O1—C1—O2	5.0 (5)
C2—Na2—O1—C1	81.8 (5)	Na2ⁱⁱⁱ—O1—C1—C3	81.9 (5)
O1ⁱⁱⁱ—Na2—O1—Na2ⁱⁱⁱ	0.0	Na2—O1—C1—C3	−71.3 (6)
O13—Na2—O1—Na2ⁱⁱⁱ	−125.5 (5)	Na4ⁱⁱⁱ—O1—C1—C3	−173.8 (4)
O13^iv—Na2—O1—Na2ⁱⁱⁱ	162.80 (15)	Na3—O3—C2—O4	160.6 (3)
O3ⁱⁱⁱ—Na2—O1—Na2ⁱⁱⁱ	75.68 (12)	Na2ⁱⁱⁱ—O3—C2—O4	−79.4 (5)
O4—Na2—O1—Na2ⁱⁱⁱ	−87.84 (12)	Na4—O3—C2—O4	10.4 (5)
C2—Na2—O1—Na2ⁱⁱⁱ	−78.63 (14)	Na3—O3—C2—C4	−21.3 (6)
O1ⁱⁱⁱ—Na2—O1—Na4ⁱⁱⁱ	−96.93 (14)	Na2ⁱⁱⁱ—O3—C2—C4	98.7 (4)
O13—Na2—O1—Na4ⁱⁱⁱ	137.5 (5)	Na4—O3—C2—C4	−171.5 (4)
O13^iv—Na2—O1—Na4ⁱⁱⁱ	65.87 (15)	Na3^viii—O4—C2—O3	−170.1 (3)
O3ⁱⁱⁱ—Na2—O1—Na4ⁱⁱⁱ	−21.25 (13)	Na2—O4—C2—O3	77.8 (5)
O4—Na2—O1—Na4ⁱⁱⁱ	175.23 (14)	Na4—O4—C2—O3	−10.0 (5)
C2—Na2—O1—Na4ⁱⁱⁱ	−175.56 (18)	Na3^viii—O4—C2—C4	11.7 (6)
O8ⁱ—Na1—O2—C1	−110.5 (6)	Na2—O4—C2—C4	−100.4 (4)
O2ⁱⁱ—Na1—O2—C1	163.4 (5)	Na4—O4—C2—C4	171.9 (4)
O8—Na1—O2—C1	10.3 (5)	O10^vi—Na4—C2—O3	−18.2 (3)
O10—Na1—O2—C1	84.6 (5)	O1ⁱⁱⁱ—Na4—C2—O3	86.0 (3)
O9ⁱ—Na1—O2—C1	−84.8 (5)	O15—Na4—C2—O3	−110.6 (3)
O8ⁱ—Na1—O2—Na1ⁱⁱ	86.1 (4)	O2ⁱⁱⁱ—Na4—C2—O3	94.5 (3)
O2ⁱⁱ—Na1—O2—Na1ⁱⁱ	0.0	O4—Na4—C2—O3	170.6 (4)
O8—Na1—O2—Na1ⁱⁱ	−153.09 (16)	O9^vii—Na4—C2—O3	−171.8 (3)
O10—Na1—O2—Na1ⁱⁱ	−78.85 (17)	C1ⁱⁱⁱ—Na4—C2—O3	88.3 (3)
O9ⁱ—Na1—O2—Na1ⁱⁱ	111.79 (16)	O10^vi—Na4—C2—O4	171.2 (3)
C10ⁱ—Na1—O2—Na1ⁱⁱ	119.93 (16)	O1ⁱⁱⁱ—Na4—C2—O4	−84.6 (3)
O8ⁱ—Na1—O2—Na4ⁱⁱⁱ	−11.5 (5)	O15—Na4—C2—O4	78.8 (3)
O2ⁱⁱ—Na1—O2—Na4ⁱⁱⁱ	−97.52 (16)	O3—Na4—C2—O4	−170.6 (4)
O8—Na1—O2—Na4ⁱⁱⁱ	109.39 (15)	O2ⁱⁱⁱ—Na4—C2—O4	−76.2 (3)
O10—Na1—O2—Na4ⁱⁱⁱ	−176.37 (14)	O9^vii—Na4—C2—O4	17.6 (3)
O9ⁱ—Na1—O2—Na4ⁱⁱⁱ	14.27 (16)	O10^vi—Na4—C2—C4	64 (2)
O7—Na3—O3—C2	59.7 (4)	O1ⁱⁱⁱ—Na4—C2—C4	168 (2)
O4^v—Na3—O3—C2	164.7 (4)	O15—Na4—C2—C4	−28 (2)
O14—Na3—O3—C2	−44.0 (5)	O3—Na4—C2—C4	82 (2)
O11^vi—Na3—O3—C2	−111.7 (4)	O2ⁱⁱⁱ—Na4—C2—C4	177 (2)
O7—Na3—O3—Na2ⁱⁱⁱ	−65.70 (16)	O4—Na4—C2—C4	−107 (2)
O4^v—Na3—O3—Na2ⁱⁱⁱ	39.3 (3)	O9^vii—Na4—C2—C4	−89 (2)
O14—Na3—O3—Na2ⁱⁱⁱ	−169.41 (19)	O10^vi—Na4—C2—Na2	−135.11 (17)
O11^vi—Na3—O3—Na2ⁱⁱⁱ	122.85 (15)	O1ⁱⁱⁱ—Na4—C2—Na2	−30.95 (11)
O7—Na3—O3—Na4	−157.15 (19)	O15—Na4—C2—Na2	132.50 (17)
O4^v—Na3—O3—Na4	−52.2 (3)	O3—Na4—C2—Na2	−116.9 (3)
O14—Na3—O3—Na4	99.1 (2)	O2ⁱⁱⁱ—Na4—C2—Na2	−22.5 (2)
O11^vi—Na3—O3—Na4	31.4 (2)	O4—Na4—C2—Na2	53.7 (2)
O10^vi—Na4—O3—C2	164.5 (3)	O9^vii—Na4—C2—Na2	71.27 (15)
O1ⁱⁱⁱ—Na4—O3—C2	−91.0 (3)	O1ⁱⁱⁱ—Na2—C2—O3	−20.1 (3)
O15—Na4—O3—C2	70.2 (3)	O1—Na2—C2—O3	78.8 (3)
O2ⁱⁱⁱ—Na4—O3—C2	−110.2 (3)	O13—Na2—C2—O3	−114.2 (3)
O4—Na4—O3—C2	−5.2 (3)	O13^iv—Na2—C2—O3	153.7 (3)
O9^vii—Na4—O3—C2	11.0 (4)	O3ⁱⁱⁱ—Na2—C2—O3	40.3 (4)
O10^vi—Na4—O3—Na3	9.7 (2)	O4—Na2—C2—O3	−124.8 (5)
O1ⁱⁱⁱ—Na4—O3—Na3	114.2 (2)	O1ⁱⁱⁱ—Na2—C2—O4	104.7 (3)
O15—Na4—O3—Na3	−84.7 (2)	O1—Na2—C2—O4	−156.4 (3)
O2ⁱⁱⁱ—Na4—O3—Na3	94.9 (2)	O13—Na2—C2—O4	10.5 (3)
O4—Na4—O3—Na3	−160.0 (2)	O13^iv—Na2—C2—O4	−81.5 (3)
O9^vii—Na4—O3—Na3	−143.8 (2)	O3ⁱⁱⁱ—Na2—C2—O4	165.1 (3)
O10^vi—Na4—O3—Na2ⁱⁱⁱ	−85.14 (15)	O1ⁱⁱⁱ—Na2—C2—C4	−149.8 (3)
O1ⁱⁱⁱ—Na4—O3—Na2ⁱⁱⁱ	19.36 (13)	O1—Na2—C2—C4	−50.9 (3)
O15—Na4—O3—Na2ⁱⁱⁱ	−179.53 (17)	O13—Na2—C2—C4	116.1 (3)
O2ⁱⁱⁱ—Na4—O3—Na2ⁱⁱⁱ	0.1 (2)	O13^iv—Na2—C2—C4	24.0 (3)
O4—Na4—O3—Na2ⁱⁱⁱ	105.12 (15)	O3ⁱⁱⁱ—Na2—C2—C4	−89.4 (3)
O9^vii—Na4—O3—Na2ⁱⁱⁱ	121.3 (2)	O4—Na2—C2—C4	105.5 (4)
C1ⁱⁱⁱ—Na4—O3—Na2ⁱⁱⁱ	9.97 (16)	O1ⁱⁱⁱ—Na2—C2—Na4	32.96 (12)
C2—Na4—O3—Na2ⁱⁱⁱ	110.3 (3)	O1—Na2—C2—Na4	131.83 (17)
O1ⁱⁱⁱ—Na2—O4—C2	−73.5 (3)	O13—Na2—C2—Na4	−61.18 (16)
O1—Na2—O4—C2	19.9 (3)	O13^iv—Na2—C2—Na4	−153.27 (14)
O13—Na2—O4—C2	−170.2 (3)	O3ⁱⁱⁱ—Na2—C2—Na4	93.33 (19)
O13^iv—Na2—O4—C2	107.6 (3)	O4—Na2—C2—Na4	−71.7 (3)
O3ⁱⁱⁱ—Na2—O4—C2	−28.0 (5)	O2—C1—C3—C4	178.1 (4)
O1ⁱⁱⁱ—Na2—O4—Na3^viii	148.55 (13)	O1—C1—C3—C4	−3.1 (7)
O1—Na2—O4—Na3^viii	−118.03 (14)	O2—C1—C3—C8	−4.0 (7)
O13—Na2—O4—Na3^viii	51.86 (14)	O1—C1—C3—C8	174.9 (4)
O13^iv—Na2—O4—Na3^viii	−30.31 (16)	C8—C3—C4—C5	−1.1 (7)
O3ⁱⁱⁱ—Na2—O4—Na3^viii	−166.0 (3)	C1—C3—C4—C5	176.8 (4)
C2—Na2—O4—Na3^viii	−138.0 (3)	C8—C3—C4—C2	−179.1 (4)
O1ⁱⁱⁱ—Na2—O4—Na4	15.07 (13)	C1—C3—C4—C2	−1.1 (7)
O1—Na2—O4—Na4	108.50 (13)	O3—C2—C4—C5	97.5 (5)
O13—Na2—O4—Na4	−81.61 (13)	O4—C2—C4—C5	−84.2 (6)
O13^iv—Na2—O4—Na4	−163.78 (13)	O3—C2—C4—C3	−84.6 (6)
O3ⁱⁱⁱ—Na2—O4—Na4	60.5 (4)	O4—C2—C4—C3	93.7 (5)
C2—Na2—O4—Na4	88.6 (3)	C3—C4—C5—C6	1.1 (8)
O10^vi—Na4—O4—C2	−13.9 (4)	C2—C4—C5—C6	179.1 (5)
O1ⁱⁱⁱ—Na4—O4—C2	92.1 (3)	C3—C4—C5—N1	−178.9 (5)
O15—Na4—O4—C2	−99.0 (3)	C2—C4—C5—N1	−0.8 (7)
O3—Na4—O4—C2	5.2 (2)	O5—N1—C5—C4	−16.7 (9)
O2ⁱⁱⁱ—Na4—O4—C2	124.1 (3)	O6—N1—C5—C4	−171.9 (10)
O9^vii—Na4—O4—C2	−163.6 (3)	O6'—N1—C5—C4	131.8 (11)
C1ⁱⁱⁱ—Na4—O4—C2	105.6 (3)	O5—N1—C5—C6	163.4 (6)
O10^vi—Na4—O4—Na3^viii	146.4 (3)	O6—N1—C5—C6	8.1 (12)
O1ⁱⁱⁱ—Na4—O4—Na3^viii	−107.6 (2)	O6'—N1—C5—C6	−48.2 (12)
O15—Na4—O4—Na3^viii	61.3 (2)	C4—C5—C6—C7	−0.2 (9)
O3—Na4—O4—Na3^viii	165.4 (3)	N1—C5—C6—C7	179.8 (5)
O2ⁱⁱⁱ—Na4—O4—Na3^viii	−75.6 (3)	C5—C6—C7—C8	−0.7 (8)
O9^vii—Na4—O4—Na3^viii	−3.3 (2)	C6—C7—C8—C3	0.7 (8)
C1ⁱⁱⁱ—Na4—O4—Na3^viii	−94.1 (2)	C4—C3—C8—C7	0.3 (7)
C2—Na4—O4—Na3^viii	160.3 (4)	C1—C3—C8—C7	−177.8 (5)
O10^vi—Na4—O4—Na2	−120.4 (3)	Na1ⁱ—O8—C9—O7	100.8 (6)
O1ⁱⁱⁱ—Na4—O4—Na2	−14.41 (13)	Na1—O8—C9—O7	−101.8 (6)
O15—Na4—O4—Na2	154.48 (18)	Na1ⁱ—O8—C9—C11	−80.0 (7)
O3—Na4—O4—Na2	−101.40 (15)	Na1—O8—C9—C11	77.5 (6)
O2ⁱⁱⁱ—Na4—O4—Na2	17.56 (19)	Na3—O7—C9—O8	177.4 (14)
O9^vii—Na4—O4—Na2	89.89 (13)	Na3—O7—C9—C11	−2 (2)
O3—Na3—O7—C9	−102.8 (17)	Na4^x—O10—C10—O9	117.5 (8)
O4^v—Na3—O7—C9	115.6 (17)	Na1—O10—C10—O9	−80.8 (7)
O14—Na3—O7—C9	8.8 (18)	Na4^x—O10—C10—C12	−63.6 (10)
O11^vi—Na3—O7—C9	−16 (3)	Na1—O10—C10—C12	98.1 (5)
O2—Na1—O8—C9	32.0 (5)	Na1ⁱ—O9—C10—O10	69.8 (7)
O8ⁱ—Na1—O8—C9	−165.3 (5)	Na4^ix—O9—C10—O10	−86.9 (14)
O2ⁱⁱ—Na1—O8—C9	−50.5 (7)	Na1ⁱ—O9—C10—C12	−109.1 (4)
O10—Na1—O8—C9	−79.7 (5)	Na4^ix—O9—C10—C12	94.2 (13)
O9ⁱ—Na1—O8—C9	119.9 (5)	O8—C9—C11—C16	−177.7 (5)
O2—Na1—O8—Na1ⁱ	−162.62 (15)	O7—C9—C11—C16	1.6 (7)
O8ⁱ—Na1—O8—Na1ⁱ	0.0	O8—C9—C11—C12	1.6 (7)
O2ⁱⁱ—Na1—O8—Na1ⁱ	114.8 (3)	O7—C9—C11—C12	−179.1 (5)
O10—Na1—O8—Na1ⁱ	85.65 (16)	C16—C11—C12—C13	1.8 (8)
O9ⁱ—Na1—O8—Na1ⁱ	−74.71 (15)	C9—C11—C12—C13	−177.5 (5)
O2—Na1—O10—C10	−105.2 (5)	C16—C11—C12—C10	−177.7 (5)
O8ⁱ—Na1—O10—C10	80.0 (5)	C9—C11—C12—C10	3.0 (8)
O2ⁱⁱ—Na1—O10—C10	176.1 (5)	O10—C10—C12—C13	88.0 (7)
O8—Na1—O10—C10	−16.8 (4)	O9—C10—C12—C13	−92.9 (7)
O9ⁱ—Na1—O10—C10	45.6 (7)	O10—C10—C12—C11	−92.5 (6)
O2—Na1—O10—Na4^x	65.52 (19)	O9—C10—C12—C11	86.5 (7)
O8ⁱ—Na1—O10—Na4^x	−109.31 (18)	C11—C12—C13—C14	−0.7 (9)
O2ⁱⁱ—Na1—O10—Na4^x	−13.19 (16)	C10—C12—C13—C14	178.8 (6)
O8—Na1—O10—Na4^x	154.0 (2)	C11—C12—C13—N2	179.9 (5)
O9ⁱ—Na1—O10—Na4^x	−143.7 (4)	C10—C12—C13—N2	−0.7 (9)
O12—N2—O11—Na3^x	6.4 (14)	O12—N2—C13—C14	7.1 (9)
O1ⁱⁱⁱ—Na2—O13—Na2^iv	162.01 (16)	O11—N2—C13—C14	−171.5 (6)
O1—Na2—O13—Na2^iv	−72.9 (5)	O12—N2—C13—C12	−173.4 (6)
O13^iv—Na2—O13—Na2^iv	0.0	O11—N2—C13—C12	8.0 (9)
O3ⁱⁱⁱ—Na2—O13—Na2^iv	84.68 (16)	C12—C13—C14—C15	−1.2 (10)
O4—Na2—O13—Na2^iv	−109.64 (15)	N2—C13—C14—C15	178.3 (6)
Na1—O2—C1—O1	99.1 (5)	C13—C14—C15—C16	1.8 (10)
Na1ⁱⁱ—O2—C1—O1	−101.6 (5)	C12—C11—C16—C15	−1.2 (9)
Na4ⁱⁱⁱ—O2—C1—O1	−4.7 (5)	C9—C11—C16—C15	178.1 (5)
Na1—O2—C1—C3	−82.1 (5)	C14—C15—C16—C11	−0.6 (10)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13A···O7ⁱⁱⁱ	0.85	1.94	2.789 (6)	180
O13—H13A···O8ⁱⁱⁱ	0.85	2.51	3.049 (5)	123
O13—H13B···O10^vii	0.85	2.13	2.980 (6)	180
O13—H13B···O9^vii	0.85	2.63	3.186 (6)	125
O14—H14B···O6^xi	0.85	1.93	2.782 (13)	179
O14—H14B···O6′^xi	0.85	1.97	2.722 (15)	147
O14—H14C···O6′^v	0.85	1.45	2.29 (2)	166
O14—H14C···N1^v	0.85	2.27	3.078 (10)	160
O14—H14C···O6^v	0.85	2.55	3.388 (18)	171
O15—H15B···O5	0.85	2.13	2.951 (7)	162
O15—H15C···O9^vii	0.85	2.29	2.782 (8)	117
O15—H15C···O11^vii	0.85	2.48	3.302 (8)	163

Symmetry codes: (iii) −x+1, −y+1, −z+1; (v) x−1, y, z; (vii) x+1, y+1, z; (xi) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Na₄(C₈H₃NO₆)₂(H₂O)₃]
M_r	564.24
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	6.6871 (8), 10.6193 (15), 14.582 (2)
α, β, γ (°)	82.065 (1), 83.428 (1), 89.371 (2)
V (Å³)	1018.8 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.44 × 0.38 × 0.17

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.905, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	5276, 3514, 2272
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.208, 1.04
No. of reflections	3514
No. of parameters	344
No. of restraints	162
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.76, −0.69

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Na1—O2	2.323 (4)	Na3—O7	2.270 (4)
Na1—O8ⁱ	2.354 (4)	Na3—O3	2.358 (4)
Na1—O2ⁱⁱ	2.357 (4)	Na3—O4^v	2.390 (4)
Na1—O8	2.374 (4)	Na3—O14	2.419 (7)
Na1—O10	2.502 (5)	Na3—O11^vi	2.488 (5)
Na1—O9ⁱ	2.511 (5)	Na4—O10^vi	2.363 (5)
Na2—O1ⁱⁱⁱ	2.312 (4)	Na4—O1ⁱⁱⁱ	2.437 (4)
Na2—O1	2.320 (4)	Na4—O15	2.448 (6)
Na2—O13	2.326 (4)	Na4—O3	2.546 (4)
Na2—O13^iv	2.353 (4)	Na4—O2ⁱⁱⁱ	2.563 (4)
Na2—O3ⁱⁱⁱ	2.474 (4)	Na4—O4	2.647 (4)
Na2—O4	2.475 (4)	Na4—O9^vii	2.755 (6)

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