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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): m1509–m1510.
Published online 2010 November 6. doi:  10.1107/S1600536810044600
PMCID: PMC3011426

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

Abstract

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.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-66-m1509-scheme1.jpg

Experimental

Crystal data

  • [Na4(C8H3NO6)2(H2O)3]
  • M r = 564.24
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1509-efi1.jpg
  • a = 6.6871 (8) Å
  • b = 10.6193 (15) Å
  • c = 14.582 (2) Å
  • α = 82.065 (1)°
  • β = 83.428 (1)°
  • γ = 89.371 (2)°
  • V = 1018.8 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.23 mm−1
  • T = 298 K
  • 0.44 × 0.38 × 0.17 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2002 [triangle]) T min = 0.905, T max = 0.962
  • 5276 measured reflections
  • 3514 independent reflections
  • 2272 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

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

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

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810044600/hb5692sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044600/hb5692Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by the Scientific Research Foundation of Northwest A&F University (grant No. Z111020828).

supplementary crystallographic information

Comment

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 NaI ions, two 3-Nitrobenzene-1,2-dicarboxylato and three coordinated water molecules in the asymmetric unit. Only one independent NaI 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 Na1I and Na2I ions could be described as distorted octahedral arrangements with coordination number of 6, all the coordinated atoms are oxygen atoms. For Na1I center, all the six oxygen atoms come from carboxylate groups. For Na2I center, four oxygen atoms come from carboxylate groups, two of them come from coordinated water molecules. The coordination numbers of Na3I and Na4I ions are 5 and 7, and the geometries around them could be described as distorted trigonal bipyramid and moncapped octahedron prism arrangements. Around Na3I center, three oxygen atoms come from carboxylate groups, one is nitro oxygen atom, and the last comes from coordinated water molecule. Concerning Na4I 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.

Experimental

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.

Figures

Fig. 1.
Coordination environment of NaI 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) ...
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.

Crystal data

[Na4(C8H3NO6)2(H2O)3]Z = 2
Mr = 564.24F(000) = 572
Triclinic, P1Dx = 1.839 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.6871 (8) ÅCell parameters from 1631 reflections
b = 10.6193 (15) Åθ = 2.8–28.2°
c = 14.582 (2) ŵ = 0.23 mm1
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

Bruker SMART CCD diffractometer3514 independent reflections
Radiation source: fine-focus sealed tube2272 reflections with I > 2σ(I)
graphiteRint = 0.026
phi and ω scansθmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2002)h = −7→7
Tmin = 0.905, Tmax = 0.962k = −11→12
5276 measured reflectionsl = −17→14

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.208H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.1154P)2 + 0.9421P] where P = (Fo2 + 2Fc2)/3
3514 reflections(Δ/σ)max < 0.001
344 parametersΔρmax = 0.76 e Å3
162 restraintsΔρmin = −0.69 e Å3

Special details

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)

xyzUiso*/UeqOcc. (<1)
Na10.2359 (3)0.00241 (17)0.50423 (14)0.0330 (5)
Na20.7386 (3)0.50445 (17)0.49820 (13)0.0302 (5)
Na30.0578 (3)0.5315 (2)0.28461 (17)0.0479 (6)
Na40.5016 (4)0.7672 (2)0.37516 (15)0.0522 (7)
N10.6311 (9)0.5233 (5)0.1143 (3)0.0533 (14)
N20.1544 (9)−0.1646 (5)0.1478 (4)0.0556 (14)
O10.5149 (5)0.3531 (3)0.4692 (2)0.0299 (8)
O20.5038 (5)0.1449 (3)0.4694 (2)0.0335 (8)
O30.3758 (5)0.5587 (3)0.3345 (2)0.0328 (8)
O40.7092 (5)0.5666 (3)0.3304 (2)0.0324 (8)
O50.5745 (9)0.6168 (4)0.1406 (3)0.0703 (13)
O60.645 (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)
O70.0464 (6)0.3179 (4)0.3283 (3)0.0511 (10)
O80.0225 (6)0.1255 (3)0.4077 (3)0.0434 (9)
O9−0.1331 (8)−0.1086 (4)0.3542 (3)0.0583 (11)
O100.1955 (8)−0.1197 (4)0.3725 (3)0.0644 (11)
O110.0978 (9)−0.2416 (5)0.2146 (3)0.0735 (13)
O120.2147 (11)−0.1972 (6)0.0737 (4)0.104 (2)
O131.0048 (6)0.6475 (3)0.4843 (3)0.0438 (10)
H13A0.98970.65830.54140.053*
H13B1.05950.71390.45260.053*
O140.0893 (12)0.5436 (6)0.1167 (5)0.116 (2)
H14B0.17130.52300.07240.139*
H14C−0.02900.54120.10090.139*
O150.6276 (9)0.8569 (5)0.2156 (4)0.0861 (16)
H15B0.58520.79320.19390.103*
H15C0.75250.84650.22010.103*
C10.5209 (7)0.2562 (4)0.4276 (3)0.0250 (10)
C20.5488 (7)0.5173 (4)0.3145 (3)0.0235 (10)
C30.5542 (7)0.2752 (4)0.3225 (3)0.0256 (11)
C40.5689 (7)0.3952 (4)0.2700 (3)0.0224 (10)
C50.6096 (8)0.4004 (5)0.1743 (3)0.0328 (12)
C60.6326 (9)0.2933 (5)0.1290 (4)0.0418 (14)
H60.65950.30090.06450.050*
C70.6145 (8)0.1769 (5)0.1820 (4)0.0384 (13)
H70.62760.10360.15350.046*
C80.5770 (8)0.1676 (5)0.2771 (4)0.0320 (12)
H80.56640.08750.31240.038*
C90.0500 (8)0.1990 (5)0.3334 (4)0.0368 (13)
C100.0487 (11)−0.0812 (5)0.3305 (4)0.0437 (15)
C110.0931 (8)0.1445 (5)0.2430 (4)0.0379 (13)
C120.0976 (8)0.0117 (5)0.2412 (4)0.0376 (13)
C130.1464 (9)−0.0290 (6)0.1550 (4)0.0448 (14)
C140.1874 (10)0.0541 (7)0.0734 (4)0.0580 (18)
H14A0.22190.02320.01710.070*
C150.1767 (11)0.1815 (7)0.0762 (5)0.0615 (19)
H15A0.20030.23830.02150.074*
C160.1308 (9)0.2257 (6)0.1606 (5)0.0510 (16)
H160.12520.31290.16210.061*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Na10.0312 (11)0.0249 (11)0.0412 (12)−0.0031 (8)−0.0024 (9)0.0004 (9)
Na20.0293 (11)0.0276 (11)0.0333 (11)−0.0011 (8)−0.0008 (8)−0.0051 (8)
Na30.0333 (13)0.0374 (13)0.0668 (16)−0.0031 (10)−0.0023 (11)0.0127 (11)
Na40.0914 (19)0.0293 (12)0.0323 (12)0.0099 (12)0.0022 (12)0.0002 (9)
N10.092 (4)0.037 (3)0.026 (3)−0.010 (3)0.010 (3)−0.001 (2)
N20.070 (4)0.059 (4)0.038 (3)0.009 (3)−0.004 (3)−0.008 (3)
O10.0361 (18)0.0217 (16)0.0308 (16)−0.0013 (13)−0.0004 (14)−0.0032 (13)
O20.0379 (19)0.0186 (16)0.0406 (19)−0.0014 (14)−0.0009 (15)0.0050 (14)
O30.0352 (18)0.0261 (16)0.0368 (18)0.0034 (14)−0.0020 (14)−0.0061 (14)
O40.0358 (18)0.0217 (16)0.0388 (18)−0.0050 (14)0.0000 (14)−0.0046 (13)
O50.108 (3)0.043 (2)0.052 (2)0.008 (2)0.010 (2)0.004 (2)
O60.135 (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)
O70.052 (2)0.034 (2)0.064 (2)0.0012 (17)−0.0030 (19)0.0017 (17)
O80.052 (2)0.0327 (18)0.0437 (19)−0.0015 (16)−0.0045 (16)0.0015 (16)
O90.082 (3)0.041 (2)0.048 (2)−0.010 (2)0.006 (2)−0.0049 (17)
O100.090 (3)0.051 (2)0.049 (2)0.024 (2)−0.009 (2)−0.0013 (18)
O110.114 (3)0.049 (2)0.053 (2)0.011 (2)0.008 (2)−0.004 (2)
O120.171 (5)0.081 (4)0.057 (3)0.001 (4)0.020 (3)−0.025 (3)
O130.042 (2)0.0249 (18)0.062 (2)−0.0068 (16)0.0022 (18)−0.0012 (17)
O140.143 (5)0.094 (4)0.099 (4)0.000 (4)0.020 (4)−0.002 (3)
O150.088 (4)0.057 (3)0.111 (4)−0.003 (3)−0.002 (3)−0.008 (3)
C10.020 (2)0.024 (3)0.031 (3)0.0011 (19)−0.0023 (19)−0.002 (2)
C20.029 (3)0.015 (2)0.025 (2)−0.004 (2)0.002 (2)−0.0002 (18)
C30.019 (2)0.028 (3)0.030 (3)−0.001 (2)−0.0028 (19)−0.004 (2)
C40.021 (2)0.022 (2)0.024 (2)−0.0027 (19)0.0006 (19)−0.0054 (19)
C50.038 (3)0.029 (3)0.030 (3)−0.004 (2)0.001 (2)−0.003 (2)
C60.056 (4)0.042 (3)0.028 (3)0.001 (3)0.002 (3)−0.011 (2)
C70.043 (3)0.036 (3)0.039 (3)−0.002 (2)−0.003 (3)−0.018 (3)
C80.031 (3)0.023 (3)0.044 (3)0.000 (2)−0.007 (2)−0.011 (2)
C90.024 (3)0.030 (3)0.057 (4)−0.004 (2)−0.006 (2)−0.003 (3)
C100.069 (4)0.029 (3)0.033 (3)0.014 (3)−0.008 (3)−0.004 (2)
C110.026 (3)0.035 (3)0.048 (3)−0.004 (2)−0.003 (2)0.009 (2)
C120.031 (3)0.039 (3)0.041 (3)0.001 (2)−0.005 (2)0.003 (2)
C130.047 (4)0.047 (4)0.039 (3)0.000 (3)−0.005 (3)0.001 (3)
C140.061 (4)0.075 (5)0.035 (4)−0.008 (4)−0.005 (3)0.004 (3)
C150.064 (5)0.063 (5)0.050 (4)−0.018 (4)−0.007 (3)0.020 (3)
C160.044 (4)0.045 (4)0.059 (4)−0.010 (3)−0.007 (3)0.011 (3)

Geometric parameters (Å, °)

Na1—O22.323 (4)O4—Na3viii2.390 (4)
Na1—O8i2.354 (4)O7—C91.255 (6)
Na1—O2ii2.357 (4)O8—C91.240 (7)
Na1—O82.374 (4)O8—Na1i2.354 (4)
Na1—O102.502 (5)O9—C101.252 (8)
Na1—O9i2.511 (5)O9—Na1i2.511 (5)
Na2—O1iii2.312 (4)O9—Na4ix2.755 (6)
Na2—O12.320 (4)O10—C101.251 (7)
Na2—O132.326 (4)O10—Na4x2.363 (5)
Na2—O13iv2.353 (4)O11—Na3x2.488 (5)
Na2—O3iii2.474 (4)O13—Na2iv2.353 (4)
Na2—O42.475 (4)O13—H13A0.8498
Na3—O72.270 (4)O13—H13B0.8500
Na3—O32.358 (4)O14—H14B0.8500
Na3—O4v2.390 (4)O14—H14C0.8500
Na3—O142.419 (7)O15—H15B0.8500
Na3—O11vi2.488 (5)O15—H15C0.8500
Na4—O10vi2.363 (5)C1—C31.509 (7)
Na4—O1iii2.437 (4)C2—C41.526 (6)
Na4—O152.448 (6)C3—C41.391 (7)
Na4—O32.546 (4)C3—C81.396 (7)
Na4—O2iii2.563 (4)C4—C51.385 (7)
Na4—O42.647 (4)C5—C61.390 (7)
Na4—O9vii2.755 (6)C6—C71.363 (8)
N1—O51.156 (6)C6—H60.9300
N1—O61.236 (10)C7—C81.371 (7)
N1—O6'1.320 (15)C7—H70.9300
N1—C51.466 (7)C8—H80.9300
N2—O121.204 (7)C9—C111.509 (8)
N2—O111.209 (7)C10—C121.527 (8)
N2—C131.458 (8)C11—C161.378 (8)
O1—C11.263 (6)C11—C121.414 (8)
O1—Na2iii2.312 (4)C12—C131.387 (8)
O1—Na4iii2.437 (4)C13—C141.382 (8)
O2—C11.253 (6)C14—C151.359 (10)
O2—Na1ii2.357 (4)C14—H14A0.9300
O2—Na4iii2.563 (4)C15—C161.379 (10)
O3—C21.250 (6)C15—H15A0.9300
O3—Na2iii2.474 (4)C16—H160.9300
O4—C21.257 (6)
O2—Na1—O8i159.75 (16)C2—O4—Na2106.5 (3)
O2—Na1—O2ii82.43 (13)Na3viii—O4—Na293.63 (14)
O8i—Na1—O2ii95.74 (14)C2—O4—Na489.2 (3)
O2—Na1—O894.71 (14)Na3viii—O4—Na4133.50 (16)
O8i—Na1—O895.73 (14)Na2—O4—Na488.06 (12)
O2ii—Na1—O8153.10 (16)C9—O7—Na3167.2 (4)
O2—Na1—O10112.15 (17)C9—O8—Na1i139.0 (4)
O8i—Na1—O1087.46 (16)C9—O8—Na1134.7 (4)
O2ii—Na1—O1082.65 (15)Na1i—O8—Na184.27 (14)
O8—Na1—O1073.64 (15)C10—O9—Na1i105.9 (4)
O2—Na1—O9i87.49 (15)C10—O9—Na4ix161.6 (4)
O8i—Na1—O9i74.31 (15)Na1i—O9—Na4ix91.05 (16)
O2ii—Na1—O9i111.21 (16)C10—O10—Na4x149.5 (4)
O8—Na1—O9i95.30 (16)C10—O10—Na1111.7 (4)
O10—Na1—O9i157.80 (19)Na4x—O10—Na197.44 (19)
O1iii—Na2—O193.04 (13)N2—O11—Na3x148.5 (4)
O1iii—Na2—O1396.65 (14)Na2—O13—Na2iv96.95 (14)
O1—Na2—O13163.33 (16)Na2—O13—H13A94.9
O1iii—Na2—O13iv162.13 (16)Na2iv—O13—H13A94.7
O1—Na2—O13iv91.84 (14)Na2—O13—H13B144.8
O13—Na2—O13iv83.05 (14)Na2iv—O13—H13B106.7
O1iii—Na2—O3iii75.90 (13)H13A—O13—H13B108.4
O1—Na2—O3iii86.70 (13)Na3—O14—H14B139.6
O13—Na2—O3iii108.79 (15)Na3—O14—H14C107.4
O13iv—Na2—O3iii87.24 (14)H14B—O14—H14C108.1
O1iii—Na2—O488.52 (13)Na4—O15—H15B91.7
O1—Na2—O478.00 (12)Na4—O15—H15C97.8
O13—Na2—O488.70 (14)H15B—O15—H15C107.9
O13iv—Na2—O4109.32 (14)O2—C1—O1123.1 (4)
O3iii—Na2—O4157.58 (14)O2—C1—C3118.4 (4)
O7—Na3—O394.91 (15)O1—C1—C3118.4 (4)
O7—Na3—O4v95.67 (15)O2—C1—Na4iii64.5 (3)
O3—Na3—O4v140.24 (16)O1—C1—Na4iii58.8 (2)
O7—Na3—O14101.1 (2)C3—C1—Na4iii174.0 (3)
O3—Na3—O14110.0 (2)O3—C2—O4125.2 (4)
O4v—Na3—O14105.3 (2)O3—C2—C4118.1 (4)
O7—Na3—O11vi171.5 (2)O4—C2—C4116.7 (4)
O3—Na3—O11vi84.59 (17)O3—C2—Na460.6 (2)
O4v—Na3—O11vi90.07 (16)O4—C2—Na465.3 (2)
O14—Na3—O11vi71.2 (2)C4—C2—Na4172.4 (3)
O10vi—Na4—O1iii105.27 (16)O3—C2—Na2103.5 (3)
O10vi—Na4—O1593.48 (18)O4—C2—Na250.4 (2)
O1iii—Na4—O15161.21 (19)C4—C2—Na2114.3 (3)
O10vi—Na4—O397.84 (18)Na4—C2—Na272.89 (12)
O1iii—Na4—O382.68 (13)C4—C3—C8119.3 (4)
O15—Na4—O396.15 (17)C4—C3—C1122.5 (4)
O10vi—Na4—O2iii81.22 (15)C8—C3—C1118.2 (4)
O1iii—Na4—O2iii52.44 (11)C5—C4—C3117.1 (4)
O15—Na4—O2iii131.77 (18)C5—C4—C2120.5 (4)
O3—Na4—O2iii132.08 (14)C3—C4—C2122.4 (4)
O10vi—Na4—O4147.23 (18)C4—C5—C6123.7 (5)
O1iii—Na4—O482.10 (12)C4—C5—N1120.4 (4)
O15—Na4—O482.72 (16)C6—C5—N1116.0 (5)
O3—Na4—O450.71 (12)C7—C6—C5118.0 (5)
O2iii—Na4—O4124.99 (14)C7—C6—H6121.0
O10vi—Na4—O9vii121.48 (18)C5—C6—H6121.0
O1iii—Na4—O9vii103.59 (15)C6—C7—C8120.2 (5)
O15—Na4—O9vii64.33 (17)C6—C7—H7119.9
O3—Na4—O9vii135.66 (16)C8—C7—H7119.9
O2iii—Na4—O9vii77.88 (14)C7—C8—C3121.7 (5)
O4—Na4—O9vii86.19 (14)C7—C8—H8119.1
O5—N1—O6115.1 (7)C3—C8—H8119.1
O5—N1—O6'118.7 (8)O8—C9—O7123.9 (5)
O6—N1—O6'51.1 (8)O8—C9—C11119.2 (5)
O5—N1—C5121.9 (5)O7—C9—C11116.9 (5)
O6—N1—C5118.6 (6)O10—C10—O9127.4 (6)
O6'—N1—C5111.5 (7)O10—C10—C12116.0 (6)
O12—N2—O11121.3 (6)O9—C10—C12116.6 (5)
O12—N2—C13118.4 (6)O10—C10—Na1i99.6 (4)
O11—N2—C13120.3 (5)O9—C10—Na1i51.2 (3)
C1—O1—Na2iii132.4 (3)C12—C10—Na1i120.5 (3)
C1—O1—Na2137.6 (3)C16—C11—C12119.3 (6)
Na2iii—O1—Na286.96 (13)C16—C11—C9119.4 (5)
C1—O1—Na4iii94.9 (3)C12—C11—C9121.3 (5)
Na2iii—O1—Na4iii97.15 (14)C13—C12—C11116.9 (5)
Na2—O1—Na4iii94.76 (14)C13—C12—C10122.3 (5)
C1—O2—Na1133.0 (3)C11—C12—C10120.8 (5)
C1—O2—Na1ii127.2 (3)C14—C13—C12122.8 (6)
Na1—O2—Na1ii97.57 (13)C14—C13—N2117.2 (6)
C1—O2—Na4iii89.3 (3)C12—C13—N2119.9 (5)
Na1—O2—Na4iii100.56 (15)C15—C14—C13119.4 (6)
Na1ii—O2—Na4iii95.93 (14)C15—C14—H14A120.3
C2—O3—Na3135.0 (3)C13—C14—H14A120.3
C2—O3—Na2iii110.4 (3)C14—C15—C16119.5 (6)
Na3—O3—Na2iii94.88 (14)C14—C15—H15A120.3
C2—O3—Na494.0 (3)C16—C15—H15A120.3
Na3—O3—Na4124.18 (16)C11—C16—C15122.0 (6)
Na2iii—O3—Na488.46 (12)C11—C16—H16119.0
C2—O4—Na3viii133.8 (3)C15—C16—H16119.0
O1iii—Na2—O1—C1160.4 (5)Na1ii—O2—C1—C377.2 (5)
O13—Na2—O1—C134.9 (8)Na4iii—O2—C1—C3174.1 (4)
O13iv—Na2—O1—C1−36.8 (5)Na2iii—O1—C1—O2−99.4 (5)
O3iii—Na2—O1—C1−123.9 (5)Na2—O1—C1—O2107.5 (5)
O4—Na2—O1—C172.6 (5)Na4iii—O1—C1—O25.0 (5)
C2—Na2—O1—C181.8 (5)Na2iii—O1—C1—C381.9 (5)
O1iii—Na2—O1—Na2iii0.0Na2—O1—C1—C3−71.3 (6)
O13—Na2—O1—Na2iii−125.5 (5)Na4iii—O1—C1—C3−173.8 (4)
O13iv—Na2—O1—Na2iii162.80 (15)Na3—O3—C2—O4160.6 (3)
O3iii—Na2—O1—Na2iii75.68 (12)Na2iii—O3—C2—O4−79.4 (5)
O4—Na2—O1—Na2iii−87.84 (12)Na4—O3—C2—O410.4 (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—C498.7 (4)
O13—Na2—O1—Na4iii137.5 (5)Na4—O3—C2—C4−171.5 (4)
O13iv—Na2—O1—Na4iii65.87 (15)Na3viii—O4—C2—O3−170.1 (3)
O3iii—Na2—O1—Na4iii−21.25 (13)Na2—O4—C2—O377.8 (5)
O4—Na2—O1—Na4iii175.23 (14)Na4—O4—C2—O3−10.0 (5)
C2—Na2—O1—Na4iii−175.56 (18)Na3viii—O4—C2—C411.7 (6)
O8i—Na1—O2—C1−110.5 (6)Na2—O4—C2—C4−100.4 (4)
O2ii—Na1—O2—C1163.4 (5)Na4—O4—C2—C4171.9 (4)
O8—Na1—O2—C110.3 (5)O10vi—Na4—C2—O3−18.2 (3)
O10—Na1—O2—C184.6 (5)O1iii—Na4—C2—O386.0 (3)
O9i—Na1—O2—C1−84.8 (5)O15—Na4—C2—O3−110.6 (3)
O8i—Na1—O2—Na1ii86.1 (4)O2iii—Na4—C2—O394.5 (3)
O2ii—Na1—O2—Na1ii0.0O4—Na4—C2—O3170.6 (4)
O8—Na1—O2—Na1ii−153.09 (16)O9vii—Na4—C2—O3−171.8 (3)
O10—Na1—O2—Na1ii−78.85 (17)C1iii—Na4—C2—O388.3 (3)
O9i—Na1—O2—Na1ii111.79 (16)O10vi—Na4—C2—O4171.2 (3)
C10i—Na1—O2—Na1ii119.93 (16)O1iii—Na4—C2—O4−84.6 (3)
O8i—Na1—O2—Na4iii−11.5 (5)O15—Na4—C2—O478.8 (3)
O2ii—Na1—O2—Na4iii−97.52 (16)O3—Na4—C2—O4−170.6 (4)
O8—Na1—O2—Na4iii109.39 (15)O2iii—Na4—C2—O4−76.2 (3)
O10—Na1—O2—Na4iii−176.37 (14)O9vii—Na4—C2—O417.6 (3)
O9i—Na1—O2—Na4iii14.27 (16)O10vi—Na4—C2—C464 (2)
O7—Na3—O3—C259.7 (4)O1iii—Na4—C2—C4168 (2)
O4v—Na3—O3—C2164.7 (4)O15—Na4—C2—C4−28 (2)
O14—Na3—O3—C2−44.0 (5)O3—Na4—C2—C482 (2)
O11vi—Na3—O3—C2−111.7 (4)O2iii—Na4—C2—C4177 (2)
O7—Na3—O3—Na2iii−65.70 (16)O4—Na4—C2—C4−107 (2)
O4v—Na3—O3—Na2iii39.3 (3)O9vii—Na4—C2—C4−89 (2)
O14—Na3—O3—Na2iii−169.41 (19)O10vi—Na4—C2—Na2−135.11 (17)
O11vi—Na3—O3—Na2iii122.85 (15)O1iii—Na4—C2—Na2−30.95 (11)
O7—Na3—O3—Na4−157.15 (19)O15—Na4—C2—Na2132.50 (17)
O4v—Na3—O3—Na4−52.2 (3)O3—Na4—C2—Na2−116.9 (3)
O14—Na3—O3—Na499.1 (2)O2iii—Na4—C2—Na2−22.5 (2)
O11vi—Na3—O3—Na431.4 (2)O4—Na4—C2—Na253.7 (2)
O10vi—Na4—O3—C2164.5 (3)O9vii—Na4—C2—Na271.27 (15)
O1iii—Na4—O3—C2−91.0 (3)O1iii—Na2—C2—O3−20.1 (3)
O15—Na4—O3—C270.2 (3)O1—Na2—C2—O378.8 (3)
O2iii—Na4—O3—C2−110.2 (3)O13—Na2—C2—O3−114.2 (3)
O4—Na4—O3—C2−5.2 (3)O13iv—Na2—C2—O3153.7 (3)
O9vii—Na4—O3—C211.0 (4)O3iii—Na2—C2—O340.3 (4)
O10vi—Na4—O3—Na39.7 (2)O4—Na2—C2—O3−124.8 (5)
O1iii—Na4—O3—Na3114.2 (2)O1iii—Na2—C2—O4104.7 (3)
O15—Na4—O3—Na3−84.7 (2)O1—Na2—C2—O4−156.4 (3)
O2iii—Na4—O3—Na394.9 (2)O13—Na2—C2—O410.5 (3)
O4—Na4—O3—Na3−160.0 (2)O13iv—Na2—C2—O4−81.5 (3)
O9vii—Na4—O3—Na3−143.8 (2)O3iii—Na2—C2—O4165.1 (3)
O10vi—Na4—O3—Na2iii−85.14 (15)O1iii—Na2—C2—C4−149.8 (3)
O1iii—Na4—O3—Na2iii19.36 (13)O1—Na2—C2—C4−50.9 (3)
O15—Na4—O3—Na2iii−179.53 (17)O13—Na2—C2—C4116.1 (3)
O2iii—Na4—O3—Na2iii0.1 (2)O13iv—Na2—C2—C424.0 (3)
O4—Na4—O3—Na2iii105.12 (15)O3iii—Na2—C2—C4−89.4 (3)
O9vii—Na4—O3—Na2iii121.3 (2)O4—Na2—C2—C4105.5 (4)
C1iii—Na4—O3—Na2iii9.97 (16)O1iii—Na2—C2—Na432.96 (12)
C2—Na4—O3—Na2iii110.3 (3)O1—Na2—C2—Na4131.83 (17)
O1iii—Na2—O4—C2−73.5 (3)O13—Na2—C2—Na4−61.18 (16)
O1—Na2—O4—C219.9 (3)O13iv—Na2—C2—Na4−153.27 (14)
O13—Na2—O4—C2−170.2 (3)O3iii—Na2—C2—Na493.33 (19)
O13iv—Na2—O4—C2107.6 (3)O4—Na2—C2—Na4−71.7 (3)
O3iii—Na2—O4—C2−28.0 (5)O2—C1—C3—C4178.1 (4)
O1iii—Na2—O4—Na3viii148.55 (13)O1—C1—C3—C4−3.1 (7)
O1—Na2—O4—Na3viii−118.03 (14)O2—C1—C3—C8−4.0 (7)
O13—Na2—O4—Na3viii51.86 (14)O1—C1—C3—C8174.9 (4)
O13iv—Na2—O4—Na3viii−30.31 (16)C8—C3—C4—C5−1.1 (7)
O3iii—Na2—O4—Na3viii−166.0 (3)C1—C3—C4—C5176.8 (4)
C2—Na2—O4—Na3viii−138.0 (3)C8—C3—C4—C2−179.1 (4)
O1iii—Na2—O4—Na415.07 (13)C1—C3—C4—C2−1.1 (7)
O1—Na2—O4—Na4108.50 (13)O3—C2—C4—C597.5 (5)
O13—Na2—O4—Na4−81.61 (13)O4—C2—C4—C5−84.2 (6)
O13iv—Na2—O4—Na4−163.78 (13)O3—C2—C4—C3−84.6 (6)
O3iii—Na2—O4—Na460.5 (4)O4—C2—C4—C393.7 (5)
C2—Na2—O4—Na488.6 (3)C3—C4—C5—C61.1 (8)
O10vi—Na4—O4—C2−13.9 (4)C2—C4—C5—C6179.1 (5)
O1iii—Na4—O4—C292.1 (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—C25.2 (2)O5—N1—C5—C4−16.7 (9)
O2iii—Na4—O4—C2124.1 (3)O6—N1—C5—C4−171.9 (10)
O9vii—Na4—O4—C2−163.6 (3)O6'—N1—C5—C4131.8 (11)
C1iii—Na4—O4—C2105.6 (3)O5—N1—C5—C6163.4 (6)
O10vi—Na4—O4—Na3viii146.4 (3)O6—N1—C5—C68.1 (12)
O1iii—Na4—O4—Na3viii−107.6 (2)O6'—N1—C5—C6−48.2 (12)
O15—Na4—O4—Na3viii61.3 (2)C4—C5—C6—C7−0.2 (9)
O3—Na4—O4—Na3viii165.4 (3)N1—C5—C6—C7179.8 (5)
O2iii—Na4—O4—Na3viii−75.6 (3)C5—C6—C7—C8−0.7 (8)
O9vii—Na4—O4—Na3viii−3.3 (2)C6—C7—C8—C30.7 (8)
C1iii—Na4—O4—Na3viii−94.1 (2)C4—C3—C8—C70.3 (7)
C2—Na4—O4—Na3viii160.3 (4)C1—C3—C8—C7−177.8 (5)
O10vi—Na4—O4—Na2−120.4 (3)Na1i—O8—C9—O7100.8 (6)
O1iii—Na4—O4—Na2−14.41 (13)Na1—O8—C9—O7−101.8 (6)
O15—Na4—O4—Na2154.48 (18)Na1i—O8—C9—C11−80.0 (7)
O3—Na4—O4—Na2−101.40 (15)Na1—O8—C9—C1177.5 (6)
O2iii—Na4—O4—Na217.56 (19)Na3—O7—C9—O8177.4 (14)
O9vii—Na4—O4—Na289.89 (13)Na3—O7—C9—C11−2(2)
O3—Na3—O7—C9−102.8 (17)Na4x—O10—C10—O9117.5 (8)
O4v—Na3—O7—C9115.6 (17)Na1—O10—C10—O9−80.8 (7)
O14—Na3—O7—C98.8 (18)Na4x—O10—C10—C12−63.6 (10)
O11vi—Na3—O7—C9−16 (3)Na1—O10—C10—C1298.1 (5)
O2—Na1—O8—C932.0 (5)Na1i—O9—C10—O1069.8 (7)
O8i—Na1—O8—C9−165.3 (5)Na4ix—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)Na4ix—O9—C10—C1294.2 (13)
O9i—Na1—O8—C9119.9 (5)O8—C9—C11—C16−177.7 (5)
O2—Na1—O8—Na1i−162.62 (15)O7—C9—C11—C161.6 (7)
O8i—Na1—O8—Na1i0.0O8—C9—C11—C121.6 (7)
O2ii—Na1—O8—Na1i114.8 (3)O7—C9—C11—C12−179.1 (5)
O10—Na1—O8—Na1i85.65 (16)C16—C11—C12—C131.8 (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—C1080.0 (5)C9—C11—C12—C103.0 (8)
O2ii—Na1—O10—C10176.1 (5)O10—C10—C12—C1388.0 (7)
O8—Na1—O10—C10−16.8 (4)O9—C10—C12—C13−92.9 (7)
O9i—Na1—O10—C1045.6 (7)O10—C10—C12—C11−92.5 (6)
O2—Na1—O10—Na4x65.52 (19)O9—C10—C12—C1186.5 (7)
O8i—Na1—O10—Na4x−109.31 (18)C11—C12—C13—C14−0.7 (9)
O2ii—Na1—O10—Na4x−13.19 (16)C10—C12—C13—C14178.8 (6)
O8—Na1—O10—Na4x154.0 (2)C11—C12—C13—N2179.9 (5)
O9i—Na1—O10—Na4x−143.7 (4)C10—C12—C13—N2−0.7 (9)
O12—N2—O11—Na3x6.4 (14)O12—N2—C13—C147.1 (9)
O1iii—Na2—O13—Na2iv162.01 (16)O11—N2—C13—C14−171.5 (6)
O1—Na2—O13—Na2iv−72.9 (5)O12—N2—C13—C12−173.4 (6)
O13iv—Na2—O13—Na2iv0.0O11—N2—C13—C128.0 (9)
O3iii—Na2—O13—Na2iv84.68 (16)C12—C13—C14—C15−1.2 (10)
O4—Na2—O13—Na2iv−109.64 (15)N2—C13—C14—C15178.3 (6)
Na1—O2—C1—O199.1 (5)C13—C14—C15—C161.8 (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—C15178.1 (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, °)

D—H···AD—HH···AD···AD—H···A
O13—H13A···O7iii0.851.942.789 (6)180
O13—H13A···O8iii0.852.513.049 (5)123
O13—H13B···O10vii0.852.132.980 (6)180
O13—H13B···O9vii0.852.633.186 (6)125
O14—H14B···O6xi0.851.932.782 (13)179
O14—H14B···O6'xi0.851.972.722 (15)147
O14—H14C···O6'v0.851.452.29 (2)166
O14—H14C···N1v0.852.273.078 (10)160
O14—H14C···O6v0.852.553.388 (18)171
O15—H15B···O50.852.132.951 (7)162
O15—H15C···O9vii0.852.292.782 (8)117
O15—H15C···O11vii0.852.483.302 (8)163

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5692).

References

  • Bruker (2002). SADABS, SAINT and SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Guo, M.-L. (2004). Acta Cryst. E60, m1684–m1685.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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