catena-Poly[[[bis­(2-pyridone-κO)sodium]-di-μ-2-pyridone-κ⁴O:O] tetra­fluoro­borate]

In the title compound, [Na(C₅H₅NO)₄]BF₄, each Na⁺ ion, lying on an inversion centre, is octa­hedrally coordinated by four bridging and two terminal pyridone ligands, creating a cationic coordination polymer chain with tetra­fluoro­borate anions occupying the spaces between the chains.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.065
• wR factor = 0.147
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         B1

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

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

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

catena-Poly[[[bis(2-pyridone-κO)sodium]-di-µ-2-pyridone-κ⁴O:O] tetrafluoroborate]

Crystal data

[Na(C5H5NO)4]BF4	F(000) = 1008
Mr = 490.20	Dx = 1.471 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5374 reflections
a = 7.2259 (12) Å	θ = 2.4–25.8°
b = 13.521 (2) Å	µ = 0.14 mm^−1
c = 22.655 (4) Å	T = 173 K
β = 90.322 (4)°	Needle, colourless
V = 2213.5 (6) Å^3	0.42 × 0.06 × 0.06 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	5053 independent reflections
Radiation source: fine-focus sealed tube	3175 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.076
Detector resolution: 8.2 pixels mm^-1	θmax = 27.5°, θmin = 1.8°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −17→17
Tmin = 0.849, Tmax = 0.992	l = −29→29
22997 measured reflections

Refinement

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0576P)^2 + 1.6958P] where P = (Fo^2 + 2Fc^2)/3
5053 reflections	(Δ/σ)max < 0.001
326 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

Experimental. IR (cm^-1, powder film), 1643 s (C=O), 1612 s (pyridine), 1051 (BF₄). NMR (δ, MeOD) 1H, 7.59 (m, 1H, pyridine), 7.43 (d, 1H, 3J_HH = 6.0 Hz, pyridine), 6.53 (d, 1H, 3J_HH = 9.5 Hz, pyridine). 13C{1H}, 164.5 (C=O), 142.5, 134.7, 119.5, 107.3. 11B{1H} -2.1 (s). MS - ESI⁺: 337, [{Na₃(py)(BF₄)₂}⁺, 64%], 323 [{Na₂(py)₂(BF₄)}⁺, 19%], 228 [{Na₂(py)(BF₄)}⁺, 20%].

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 (Ų)

	x	y	z	Uiso*/Ueq
Na1	0.5000	0.5000	0.5000	0.0224 (3)
Na2	1.0000	0.5000	0.5000	0.0224 (3)
N1	0.7078 (3)	0.26795 (18)	0.50276 (11)	0.0225 (5)
N2	0.8010 (3)	0.54131 (18)	0.63781 (10)	0.0222 (5)
N3	0.6512 (3)	0.53176 (19)	0.35073 (10)	0.0252 (6)
N4	0.8359 (3)	0.73546 (17)	0.45411 (11)	0.0228 (5)
O1	0.7366 (3)	0.40894 (14)	0.44876 (8)	0.0253 (5)
O2	0.7592 (2)	0.59717 (14)	0.54430 (8)	0.0240 (4)
O3	0.4839 (3)	0.60875 (14)	0.42137 (8)	0.0255 (4)
O4	1.0096 (3)	0.60781 (14)	0.42057 (8)	0.0248 (4)
B1	0.1599 (5)	0.5219 (3)	0.13962 (16)	0.0315 (8)
C1	0.7660 (3)	0.3165 (2)	0.45319 (12)	0.0212 (6)
C2	0.8577 (4)	0.2569 (2)	0.41096 (13)	0.0275 (7)
H2	0.8982	0.2856	0.3750	0.033*
C3	0.8887 (4)	0.1583 (2)	0.42137 (14)	0.0342 (7)
H3	0.9515	0.1196	0.3928	0.041*
C4	0.8284 (4)	0.1140 (2)	0.47383 (14)	0.0332 (7)
H4	0.8505	0.0458	0.4811	0.040*
C5	0.7383 (4)	0.1701 (2)	0.51377 (13)	0.0274 (7)
H5A	0.6962	0.1414	0.5495	0.033*
C6	0.7405 (4)	0.6117 (2)	0.59910 (12)	0.0209 (6)
C7	0.6605 (4)	0.6979 (2)	0.62504 (13)	0.0272 (7)
H7	0.6153	0.7495	0.6005	0.033*
C8	0.6486 (4)	0.7065 (2)	0.68517 (13)	0.0331 (7)
H8A	0.5966	0.7646	0.7019	0.040*
C9	0.7122 (4)	0.6308 (2)	0.72221 (13)	0.0321 (7)
H9	0.7035	0.6369	0.7639	0.039*
C10	0.7863 (4)	0.5487 (2)	0.69771 (12)	0.0273 (7)
H10	0.8282	0.4961	0.7222	0.033*
C11	0.5393 (3)	0.6075 (2)	0.36883 (12)	0.0216 (6)
C12	0.4955 (4)	0.6789 (2)	0.32485 (13)	0.0301 (7)
H12	0.4197	0.7340	0.3345	0.036*
C13	0.5614 (4)	0.6691 (3)	0.26902 (14)	0.0386 (8)
H13	0.5288	0.7169	0.2401	0.046*
C14	0.6762 (4)	0.5902 (3)	0.25320 (14)	0.0400 (8)
H14	0.7224	0.5841	0.2142	0.048*
C15	0.7192 (4)	0.5228 (2)	0.29519 (13)	0.0330 (7)
H15	0.7976	0.4687	0.2858	0.040*
C16	0.9436 (3)	0.6932 (2)	0.41155 (12)	0.0213 (6)
C17	0.9722 (4)	0.7520 (2)	0.36032 (13)	0.0283 (7)
H17	1.0474	0.7274	0.3294	0.034*
C18	0.8935 (4)	0.8427 (2)	0.35505 (14)	0.0345 (8)
H18	0.9135	0.8804	0.3203	0.041*
C19	0.7830 (4)	0.8818 (2)	0.40024 (14)	0.0311 (7)
H19	0.7280	0.9454	0.3965	0.037*
C20	0.7570 (4)	0.8267 (2)	0.44908 (13)	0.0287 (7)
H20	0.6830	0.8516	0.4803	0.034*
H1N	0.663 (4)	0.302 (2)	0.5289 (14)	0.036 (10)*
H2N	0.844 (4)	0.486 (2)	0.6223 (13)	0.030 (9)*
H3N	0.680 (4)	0.489 (2)	0.3767 (13)	0.023 (8)*
H4N	0.804 (4)	0.699 (2)	0.4844 (14)	0.035 (9)*
F1	0.3086 (3)	0.55499 (16)	0.17229 (9)	0.0569 (6)
F2	0.1460 (3)	0.41937 (14)	0.14367 (9)	0.0479 (5)
F3	0.0019 (3)	0.56367 (18)	0.16124 (14)	0.0921 (10)
F4	0.1815 (3)	0.54898 (16)	0.08153 (9)	0.0665 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Na1	0.0252 (8)	0.0223 (8)	0.0198 (8)	0.0038 (6)	0.0026 (6)	−0.0003 (6)
Na2	0.0266 (8)	0.0204 (8)	0.0203 (8)	0.0027 (6)	0.0030 (6)	0.0014 (6)
N1	0.0244 (13)	0.0209 (13)	0.0222 (13)	0.0018 (10)	0.0002 (10)	−0.0016 (11)
N2	0.0273 (13)	0.0193 (13)	0.0199 (12)	0.0010 (10)	0.0023 (10)	−0.0036 (10)
N3	0.0256 (13)	0.0321 (15)	0.0180 (12)	0.0034 (11)	−0.0028 (10)	0.0009 (11)
N4	0.0254 (13)	0.0182 (13)	0.0249 (13)	0.0006 (10)	0.0028 (10)	0.0028 (11)
O1	0.0303 (11)	0.0209 (11)	0.0245 (11)	0.0025 (8)	0.0016 (8)	0.0001 (8)
O2	0.0307 (11)	0.0229 (11)	0.0183 (10)	−0.0009 (8)	0.0020 (8)	0.0015 (8)
O3	0.0292 (11)	0.0271 (11)	0.0202 (10)	0.0006 (9)	0.0036 (8)	−0.0011 (9)
O4	0.0323 (11)	0.0177 (10)	0.0244 (10)	0.0036 (9)	0.0025 (8)	0.0014 (8)
B1	0.0316 (19)	0.031 (2)	0.0315 (19)	−0.0048 (15)	0.0041 (15)	−0.0032 (16)
C1	0.0183 (13)	0.0238 (16)	0.0216 (14)	−0.0001 (11)	−0.0030 (11)	−0.0015 (12)
C2	0.0266 (15)	0.0285 (17)	0.0273 (16)	−0.0018 (13)	0.0014 (12)	−0.0067 (13)
C3	0.0312 (16)	0.0312 (18)	0.0403 (19)	0.0063 (14)	−0.0014 (14)	−0.0159 (15)
C4	0.0388 (17)	0.0164 (15)	0.0443 (19)	0.0076 (13)	−0.0102 (15)	−0.0051 (14)
C5	0.0301 (16)	0.0217 (16)	0.0304 (17)	−0.0051 (12)	−0.0063 (13)	0.0033 (13)
C6	0.0213 (14)	0.0195 (14)	0.0218 (14)	−0.0049 (11)	0.0035 (11)	−0.0003 (12)
C7	0.0299 (16)	0.0229 (16)	0.0288 (16)	0.0008 (12)	0.0006 (12)	−0.0036 (13)
C8	0.0376 (18)	0.0288 (17)	0.0331 (17)	0.0043 (14)	0.0075 (14)	−0.0110 (14)
C9	0.0389 (18)	0.0381 (19)	0.0195 (15)	0.0013 (14)	0.0048 (13)	−0.0042 (14)
C10	0.0296 (16)	0.0314 (17)	0.0209 (15)	−0.0034 (13)	−0.0006 (12)	0.0048 (13)
C11	0.0173 (13)	0.0232 (15)	0.0243 (15)	−0.0027 (11)	−0.0013 (11)	−0.0021 (12)
C12	0.0275 (15)	0.0314 (17)	0.0312 (17)	−0.0002 (13)	−0.0022 (13)	0.0061 (14)
C13	0.0407 (19)	0.049 (2)	0.0257 (17)	−0.0044 (16)	−0.0012 (14)	0.0163 (15)
C14	0.0340 (18)	0.067 (2)	0.0194 (16)	−0.0051 (17)	0.0055 (13)	0.0012 (16)
C15	0.0244 (15)	0.047 (2)	0.0275 (16)	0.0042 (14)	0.0047 (12)	−0.0095 (15)
C16	0.0191 (13)	0.0182 (15)	0.0265 (15)	−0.0052 (11)	−0.0027 (11)	−0.0008 (12)
C17	0.0311 (16)	0.0283 (17)	0.0255 (16)	−0.0004 (13)	0.0028 (12)	0.0048 (13)
C18	0.0422 (19)	0.0288 (18)	0.0327 (17)	−0.0046 (14)	−0.0035 (14)	0.0146 (14)
C19	0.0328 (16)	0.0170 (15)	0.0435 (19)	0.0024 (13)	−0.0069 (14)	0.0012 (14)
C20	0.0267 (15)	0.0207 (16)	0.0386 (18)	0.0045 (12)	−0.0030 (13)	−0.0016 (14)
F1	0.0578 (13)	0.0642 (14)	0.0486 (13)	−0.0279 (11)	−0.0175 (10)	0.0052 (11)
F2	0.0651 (13)	0.0323 (11)	0.0463 (12)	−0.0076 (9)	−0.0088 (10)	0.0009 (9)
F3	0.0482 (14)	0.0694 (17)	0.159 (3)	−0.0045 (12)	0.0378 (15)	−0.0532 (18)
F4	0.1094 (19)	0.0534 (14)	0.0367 (12)	−0.0151 (13)	−0.0104 (12)	0.0058 (10)

Geometric parameters (Å, º)

Na1—O1	2.4099 (18)	B1—F2	1.392 (4)
Na1—O1^i	2.4100 (18)	C1—C2	1.418 (4)
Na1—O2	2.4940 (19)	C2—C3	1.372 (4)
Na1—O2^i	2.4941 (19)	C2—H2	0.9500
Na1—O3	2.3122 (19)	C3—C4	1.402 (4)
Na1—O3^i	2.3123 (19)	C3—H3	0.9500
Na1—Na2	3.6129 (6)	C4—C5	1.351 (4)
Na1—Na2^ii	3.6130 (6)	C4—H4	0.9500
Na2—O1	2.5422 (19)	C5—H5A	0.9500
Na2—O1^iii	2.5422 (19)	C6—C7	1.429 (4)
Na2—O2	2.4043 (18)	C7—C8	1.370 (4)
Na2—O2^iii	2.4043 (18)	C7—H7	0.9500
Na2—O4^iii	2.3172 (19)	C8—C9	1.400 (4)
Na2—O4	2.3172 (19)	C8—H8A	0.9500
Na2—Na1^iv	3.6129 (6)	C9—C10	1.353 (4)
N1—C5	1.364 (4)	C9—H9	0.9500
N1—C1	1.369 (3)	C10—H10	0.9500
N1—H1N	0.81 (3)	C11—C12	1.422 (4)
N2—C10	1.366 (3)	C12—C13	1.361 (4)
N2—C6	1.364 (4)	C12—H12	0.9500
N2—H2N	0.88 (3)	C13—C14	1.399 (5)
N3—C15	1.359 (4)	C13—H13	0.9500
N3—C11	1.369 (4)	C14—C15	1.352 (5)
N3—H3N	0.85 (3)	C14—H14	0.9500
N4—C20	1.363 (4)	C15—H15	0.9500
N4—C16	1.367 (3)	C16—C17	1.423 (4)
N4—H4N	0.88 (3)	C17—C18	1.357 (4)
O1—C1	1.272 (3)	C17—H17	0.9500
O2—C6	1.265 (3)	C18—C19	1.405 (4)
O3—C11	1.258 (3)	C18—H18	0.9500
O4—C16	1.266 (3)	C19—C20	1.348 (4)
B1—F3	1.367 (4)	C19—H19	0.9500
B1—F1	1.376 (4)	C20—H20	0.9500
B1—F4	1.376 (4)
O3—Na1—O3^i	180.00 (9)	C6—O2—Na2	125.17 (17)
O3—Na1—O1	89.22 (6)	C6—O2—Na1	113.11 (15)
O3^i—Na1—O1	90.78 (6)	Na1—O2—Na2	95.04 (6)
O3—Na1—O1^i	90.78 (6)	C11—O3—Na1	134.86 (18)
O3^i—Na1—O1^i	89.22 (6)	C16—O4—Na2	133.36 (17)
O1—Na1—O1^i	180.00 (8)	F3—B1—F1	108.9 (3)
O3—Na1—O2	90.53 (6)	F3—B1—F4	109.4 (3)
O3^i—Na1—O2	89.47 (6)	F1—B1—F4	109.6 (3)
O1—Na1—O2	85.98 (6)	F3—B1—F2	109.1 (3)
O1^i—Na1—O2	94.02 (6)	F1—B1—F2	110.2 (3)
O3—Na1—O2^i	89.47 (6)	F4—B1—F2	109.7 (3)
O3^i—Na1—O2^i	90.53 (6)	O1—C1—N1	118.9 (2)
O1—Na1—O2^i	94.02 (6)	O1—C1—C2	125.7 (3)
O1^i—Na1—O2^i	85.98 (6)	N1—C1—C2	115.3 (3)
O2—Na1—O2^i	180.0	C3—C2—C1	120.9 (3)
O3—Na1—Na2	92.63 (5)	C3—C2—H2	119.6
O3^i—Na1—Na2	87.37 (5)	C1—C2—H2	119.6
O1—Na1—Na2	44.60 (5)	C2—C3—C4	120.6 (3)
O1^i—Na1—Na2	135.40 (5)	C2—C3—H3	119.7
O2—Na1—Na2	41.52 (4)	C4—C3—H3	119.7
O2^i—Na1—Na2	138.48 (4)	C5—C4—C3	118.8 (3)
O3—Na1—Na2^ii	87.37 (5)	C5—C4—H4	120.6
O3^i—Na1—Na2^ii	92.63 (5)	C3—C4—H4	120.6
O1—Na1—Na2^ii	135.40 (5)	C4—C5—N1	120.0 (3)
O1^i—Na1—Na2^ii	44.60 (5)	C4—C5—H5A	120.0
O2—Na1—Na2^ii	138.48 (4)	N1—C5—H5A	120.0
O2^i—Na1—Na2^ii	41.52 (4)	O2—C6—N2	119.1 (2)
Na2—Na1—Na2^ii	180.0	O2—C6—C7	125.2 (3)
O4^iii—Na2—O4	180.00 (9)	N2—C6—C7	115.7 (2)
O4^iii—Na2—O2	89.69 (6)	C8—C7—C6	120.4 (3)
O4—Na2—O2	90.31 (6)	C8—C7—H7	119.8
O4^iii—Na2—O2^iii	90.31 (6)	C6—C7—H7	119.8
O4—Na2—O2^iii	89.70 (6)	C7—C8—C9	120.7 (3)
O2—Na2—O2^iii	180.00 (7)	C7—C8—H8A	119.6
O4^iii—Na2—O1	91.39 (6)	C9—C8—H8A	119.6
O4—Na2—O1	88.61 (6)	C10—C9—C8	118.9 (3)
O2—Na2—O1	85.04 (6)	C10—C9—H9	120.5
O2^iii—Na2—O1	94.96 (6)	C8—C9—H9	120.5
O4^iii—Na2—O1^iii	88.61 (6)	C9—C10—N2	120.0 (3)
O4—Na2—O1^iii	91.39 (6)	C9—C10—H10	120.0
O2—Na2—O1^iii	94.96 (6)	N2—C10—H10	120.0
O2^iii—Na2—O1^iii	85.04 (6)	O3—C11—N3	119.0 (3)
O1—Na2—O1^iii	180.0	O3—C11—C12	125.6 (3)
O4^iii—Na2—Na1^iv	91.97 (5)	N3—C11—C12	115.3 (3)
O4—Na2—Na1^iv	88.03 (5)	C13—C12—C11	120.5 (3)
O2—Na2—Na1^iv	136.56 (4)	C13—C12—H12	119.8
O2^iii—Na2—Na1^iv	43.44 (4)	C11—C12—H12	119.8
O1—Na2—Na1^iv	138.27 (4)	C12—C13—C14	121.6 (3)
O1^iii—Na2—Na1^iv	41.73 (4)	C12—C13—H13	119.2
O4^iii—Na2—Na1	88.03 (5)	C14—C13—H13	119.2
O4—Na2—Na1	91.97 (5)	C15—C14—C13	117.9 (3)
O2—Na2—Na1	43.44 (4)	C15—C14—H14	121.1
O2^iii—Na2—Na1	136.56 (4)	C13—C14—H14	121.1
O1—Na2—Na1	41.73 (4)	C14—C15—N3	120.6 (3)
O1^iii—Na2—Na1	138.27 (4)	C14—C15—H15	119.7
Na1^iv—Na2—Na1	180.0	N3—C15—H15	119.7
C5—N1—C1	124.4 (3)	O4—C16—N4	118.9 (2)
C5—N1—H1N	118 (2)	O4—C16—C17	125.8 (3)
C1—N1—H1N	117 (2)	N4—C16—C17	115.3 (2)
C10—N2—C6	124.2 (3)	C18—C17—C16	121.0 (3)
C10—N2—H2N	119 (2)	C18—C17—H17	119.5
C6—N2—H2N	117 (2)	C16—C17—H17	119.5
C15—N3—C11	124.1 (3)	C17—C18—C19	121.0 (3)
C15—N3—H3N	119.3 (19)	C17—C18—H18	119.5
C11—N3—H3N	116.6 (19)	C19—C18—H18	119.5
C20—N4—C16	123.9 (3)	C20—C19—C18	118.2 (3)
C20—N4—H4N	117 (2)	C20—C19—H19	120.9
C16—N4—H4N	118 (2)	C18—C19—H19	120.9
C1—O1—Na1	125.66 (16)	C19—C20—N4	120.6 (3)
C1—O1—Na2	108.37 (16)	C19—C20—H20	119.7
Na1—O1—Na2	93.66 (6)	N4—C20—H20	119.7
O3—Na1—Na2—O4^iii	179.47 (7)	O3—Na1—O2—C6	134.85 (18)
O3^i—Na1—Na2—O4^iii	−0.53 (7)	O3^i—Na1—O2—C6	−45.15 (18)
O1—Na1—Na2—O4^iii	−94.31 (8)	O1—Na1—O2—C6	−135.97 (18)
O1^i—Na1—Na2—O4^iii	85.69 (8)	O1^i—Na1—O2—C6	44.03 (18)
O2—Na1—Na2—O4^iii	91.64 (8)	Na2—Na1—O2—C6	−131.8 (2)
O2^i—Na1—Na2—O4^iii	−88.36 (8)	Na2^ii—Na1—O2—C6	48.2 (2)
O3—Na1—Na2—O4	−0.53 (7)	O3—Na1—O2—Na2	−93.36 (6)
O3^i—Na1—Na2—O4	179.47 (7)	O3^i—Na1—O2—Na2	86.64 (6)
O1—Na1—Na2—O4	85.69 (8)	O1—Na1—O2—Na2	−4.18 (6)
O1^i—Na1—Na2—O4	−94.31 (8)	O1^i—Na1—O2—Na2	175.82 (6)
O2—Na1—Na2—O4	−88.36 (8)	Na2^ii—Na1—O2—Na2	180.0
O2^i—Na1—Na2—O4	91.64 (8)	O1—Na1—O3—C11	15.4 (2)
O3—Na1—Na2—O2	87.84 (8)	O1^i—Na1—O3—C11	−164.6 (2)
O3^i—Na1—Na2—O2	−92.16 (8)	O2—Na1—O3—C11	101.3 (2)
O1—Na1—Na2—O2	174.06 (9)	O2^i—Na1—O3—C11	−78.7 (2)
O1^i—Na1—Na2—O2	−5.95 (9)	Na2—Na1—O3—C11	59.9 (2)
O2^i—Na1—Na2—O2	180.0	Na2^ii—Na1—O3—C11	−120.1 (2)
O3—Na1—Na2—O2^iii	−92.17 (8)	O2—Na2—O4—C16	13.2 (2)
O3^i—Na1—Na2—O2^iii	87.84 (8)	O2^iii—Na2—O4—C16	−166.8 (2)
O1—Na1—Na2—O2^iii	−5.94 (9)	O1—Na2—O4—C16	98.2 (2)
O1^i—Na1—Na2—O2^iii	174.05 (9)	O1^iii—Na2—O4—C16	−81.8 (2)
O2—Na1—Na2—O2^iii	180.0	Na1^iv—Na2—O4—C16	−123.4 (2)
O2^i—Na1—Na2—O2^iii	0.0	Na1—Na2—O4—C16	56.6 (2)
O3—Na1—Na2—O1	−86.22 (8)	Na1—O1—C1—N1	−23.0 (3)
O3^i—Na1—Na2—O1	93.78 (8)	Na2—O1—C1—N1	85.7 (2)
O1^i—Na1—Na2—O1	180.0	Na1—O1—C1—C2	157.7 (2)
O2—Na1—Na2—O1	−174.06 (9)	Na2—O1—C1—C2	−93.6 (3)
O2^i—Na1—Na2—O1	5.94 (9)	C5—N1—C1—O1	−177.1 (2)
O3—Na1—Na2—O1^iii	93.78 (8)	C5—N1—C1—C2	2.3 (4)
O3^i—Na1—Na2—O1^iii	−86.22 (8)	O1—C1—C2—C3	177.4 (3)
O1—Na1—Na2—O1^iii	180.0	N1—C1—C2—C3	−1.9 (4)
O1^i—Na1—Na2—O1^iii	0.0	C1—C2—C3—C4	0.7 (4)
O2—Na1—Na2—O1^iii	5.95 (9)	C2—C3—C4—C5	0.4 (5)
O2^i—Na1—Na2—O1^iii	−174.05 (9)	C3—C4—C5—N1	−0.2 (4)
O3—Na1—O1—C1	−149.7 (2)	C1—N1—C5—C4	−1.3 (4)
O3^i—Na1—O1—C1	30.3 (2)	Na2—O2—C6—N2	−29.1 (3)
O2—Na1—O1—C1	119.7 (2)	Na1—O2—C6—N2	85.5 (2)
O2^i—Na1—O1—C1	−60.3 (2)	Na2—O2—C6—C7	150.4 (2)
Na2—Na1—O1—C1	115.8 (2)	Na1—O2—C6—C7	−94.9 (3)
Na2^ii—Na1—O1—C1	−64.2 (2)	C10—N2—C6—O2	−179.3 (2)
O3—Na1—O1—Na2	94.54 (7)	C10—N2—C6—C7	1.1 (4)
O3^i—Na1—O1—Na2	−85.46 (7)	O2—C6—C7—C8	−179.3 (3)
O2—Na1—O1—Na2	3.95 (6)	N2—C6—C7—C8	0.2 (4)
O2^i—Na1—O1—Na2	−176.05 (6)	C6—C7—C8—C9	−0.8 (4)
Na2^ii—Na1—O1—Na2	180.0	C7—C8—C9—C10	0.2 (5)
O4^iii—Na2—O1—C1	−44.09 (17)	C8—C9—C10—N2	1.1 (4)
O4—Na2—O1—C1	135.91 (17)	C6—N2—C10—C9	−1.8 (4)
O2—Na2—O1—C1	−133.66 (17)	Na1—O3—C11—N3	−7.7 (4)
O2^iii—Na2—O1—C1	46.34 (17)	Na1—O3—C11—C12	172.15 (19)
Na1^iv—Na2—O1—C1	50.44 (19)	C15—N3—C11—O3	−180.0 (3)
Na1—Na2—O1—C1	−129.56 (19)	C15—N3—C11—C12	0.2 (4)
O4^iii—Na2—O1—Na1	85.47 (6)	O3—C11—C12—C13	−179.0 (3)
O4—Na2—O1—Na1	−94.53 (6)	N3—C11—C12—C13	0.8 (4)
O2—Na2—O1—Na1	−4.10 (6)	C11—C12—C13—C14	−1.2 (5)
O2^iii—Na2—O1—Na1	175.90 (6)	C12—C13—C14—C15	0.5 (5)
Na1^iv—Na2—O1—Na1	180.0	C13—C14—C15—N3	0.5 (5)
O4^iii—Na2—O2—C6	35.5 (2)	C11—N3—C15—C14	−0.8 (5)
O4—Na2—O2—C6	−144.5 (2)	Na2—O4—C16—N4	−3.1 (4)
O1—Na2—O2—C6	126.9 (2)	Na2—O4—C16—C17	176.24 (19)
O1^iii—Na2—O2—C6	−53.1 (2)	C20—N4—C16—O4	−179.7 (2)
Na1^iv—Na2—O2—C6	−57.0 (2)	C20—N4—C16—C17	0.9 (4)
Na1—Na2—O2—C6	123.0 (2)	O4—C16—C17—C18	179.6 (3)
O4^iii—Na2—O2—Na1	−87.46 (7)	N4—C16—C17—C18	−1.0 (4)
O4—Na2—O2—Na1	92.54 (7)	C16—C17—C18—C19	0.6 (5)
O1—Na2—O2—Na1	3.97 (6)	C17—C18—C19—C20	0.0 (5)
O1^iii—Na2—O2—Na1	−176.03 (6)	C18—C19—C20—N4	−0.1 (4)
Na1^iv—Na2—O2—Na1	180.0	C16—N4—C20—C19	−0.3 (4)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3^i	0.82 (3)	1.97 (3)	2.772 (3)	168 (3)
N2—H2N···O4^iii	0.88 (3)	1.92 (3)	2.776 (3)	163 (3)
N3—H3N···O1	0.85 (3)	2.00 (3)	2.838 (3)	169 (3)
N4—H4N···O2	0.87 (3)	1.96 (3)	2.827 (3)	169 (3)

Symmetry codes: (i) −x+1, −y+1, −z+1; (iii) −x+2, −y+1, −z+1.