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

Owen, G.R.; Haddow, M.F.

doi:10.1107/S1600536806051567

Buy article online - an online subscription or single-article purchase is required to access this article.

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

G. R. Owen and M. F. Haddow

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.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806051567/kp2072sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806051567/kp2072Isup2.hkl Contains datablock I

CCDC reference: 633905

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (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

Computing details top

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] top

Crystal data top

[Na(C₅H₅NO)₄]BF₄	F(000) = 1008
M_r = 490.20	D_x = 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) Å³	0.42 × 0.06 × 0.06 mm
Z = 4

Data collection top

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

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) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0576P)² + 1.6958P] where P = (F_o² + 2F_c²)/3
5053 reflections	(Δ/σ)_max < 0.001
326 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
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) top

Na1—O1	2.4099 (18)	B1—F2	1.392 (4)
Na1—O1ⁱ	2.4100 (18)	C1—C2	1.418 (4)
Na1—O2	2.4940 (19)	C2—C3	1.372 (4)
Na1—O2ⁱ	2.4941 (19)	C2—H2	0.9500
Na1—O3	2.3122 (19)	C3—C4	1.402 (4)
Na1—O3ⁱ	2.3123 (19)	C3—H3	0.9500
Na1—Na2	3.6129 (6)	C4—C5	1.351 (4)
Na1—Na2ⁱⁱ	3.6130 (6)	C4—H4	0.9500
Na2—O1	2.5422 (19)	C5—H5A	0.9500
Na2—O1ⁱⁱⁱ	2.5422 (19)	C6—C7	1.429 (4)
Na2—O2	2.4043 (18)	C7—C8	1.370 (4)
Na2—O2ⁱⁱⁱ	2.4043 (18)	C7—H7	0.9500
Na2—O4ⁱⁱⁱ	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—O3ⁱ	180.00 (9)	C6—O2—Na2	125.17 (17)
O3—Na1—O1	89.22 (6)	C6—O2—Na1	113.11 (15)
O3ⁱ—Na1—O1	90.78 (6)	Na1—O2—Na2	95.04 (6)
O3—Na1—O1ⁱ	90.78 (6)	C11—O3—Na1	134.86 (18)
O3ⁱ—Na1—O1ⁱ	89.22 (6)	C16—O4—Na2	133.36 (17)
O1—Na1—O1ⁱ	180.00 (8)	F3—B1—F1	108.9 (3)
O3—Na1—O2	90.53 (6)	F3—B1—F4	109.4 (3)
O3ⁱ—Na1—O2	89.47 (6)	F1—B1—F4	109.6 (3)
O1—Na1—O2	85.98 (6)	F3—B1—F2	109.1 (3)
O1ⁱ—Na1—O2	94.02 (6)	F1—B1—F2	110.2 (3)
O3—Na1—O2ⁱ	89.47 (6)	F4—B1—F2	109.7 (3)
O3ⁱ—Na1—O2ⁱ	90.53 (6)	O1—C1—N1	118.9 (2)
O1—Na1—O2ⁱ	94.02 (6)	O1—C1—C2	125.7 (3)
O1ⁱ—Na1—O2ⁱ	85.98 (6)	N1—C1—C2	115.3 (3)
O2—Na1—O2ⁱ	180.0	C3—C2—C1	120.9 (3)
O3—Na1—Na2	92.63 (5)	C3—C2—H2	119.6
O3ⁱ—Na1—Na2	87.37 (5)	C1—C2—H2	119.6
O1—Na1—Na2	44.60 (5)	C2—C3—C4	120.6 (3)
O1ⁱ—Na1—Na2	135.40 (5)	C2—C3—H3	119.7
O2—Na1—Na2	41.52 (4)	C4—C3—H3	119.7
O2ⁱ—Na1—Na2	138.48 (4)	C5—C4—C3	118.8 (3)
O3—Na1—Na2ⁱⁱ	87.37 (5)	C5—C4—H4	120.6
O3ⁱ—Na1—Na2ⁱⁱ	92.63 (5)	C3—C4—H4	120.6
O1—Na1—Na2ⁱⁱ	135.40 (5)	C4—C5—N1	120.0 (3)
O1ⁱ—Na1—Na2ⁱⁱ	44.60 (5)	C4—C5—H5A	120.0
O2—Na1—Na2ⁱⁱ	138.48 (4)	N1—C5—H5A	120.0
O2ⁱ—Na1—Na2ⁱⁱ	41.52 (4)	O2—C6—N2	119.1 (2)
Na2—Na1—Na2ⁱⁱ	180.0	O2—C6—C7	125.2 (3)
O4ⁱⁱⁱ—Na2—O4	180.00 (9)	N2—C6—C7	115.7 (2)
O4ⁱⁱⁱ—Na2—O2	89.69 (6)	C8—C7—C6	120.4 (3)
O4—Na2—O2	90.31 (6)	C8—C7—H7	119.8
O4ⁱⁱⁱ—Na2—O2ⁱⁱⁱ	90.31 (6)	C6—C7—H7	119.8
O4—Na2—O2ⁱⁱⁱ	89.70 (6)	C7—C8—C9	120.7 (3)
O2—Na2—O2ⁱⁱⁱ	180.00 (7)	C7—C8—H8A	119.6
O4ⁱⁱⁱ—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
O2ⁱⁱⁱ—Na2—O1	94.96 (6)	C8—C9—H9	120.5
O4ⁱⁱⁱ—Na2—O1ⁱⁱⁱ	88.61 (6)	C9—C10—N2	120.0 (3)
O4—Na2—O1ⁱⁱⁱ	91.39 (6)	C9—C10—H10	120.0
O2—Na2—O1ⁱⁱⁱ	94.96 (6)	N2—C10—H10	120.0
O2ⁱⁱⁱ—Na2—O1ⁱⁱⁱ	85.04 (6)	O3—C11—N3	119.0 (3)
O1—Na2—O1ⁱⁱⁱ	180.0	O3—C11—C12	125.6 (3)
O4ⁱⁱⁱ—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
O2ⁱⁱⁱ—Na2—Na1^iv	43.44 (4)	C11—C12—H12	119.8
O1—Na2—Na1^iv	138.27 (4)	C12—C13—C14	121.6 (3)
O1ⁱⁱⁱ—Na2—Na1^iv	41.73 (4)	C12—C13—H13	119.2
O4ⁱⁱⁱ—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
O2ⁱⁱⁱ—Na2—Na1	136.56 (4)	C13—C14—H14	121.1
O1—Na2—Na1	41.73 (4)	C14—C15—N3	120.6 (3)
O1ⁱⁱⁱ—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—O4ⁱⁱⁱ	179.47 (7)	O3—Na1—O2—C6	134.85 (18)
O3ⁱ—Na1—Na2—O4ⁱⁱⁱ	−0.53 (7)	O3ⁱ—Na1—O2—C6	−45.15 (18)
O1—Na1—Na2—O4ⁱⁱⁱ	−94.31 (8)	O1—Na1—O2—C6	−135.97 (18)
O1ⁱ—Na1—Na2—O4ⁱⁱⁱ	85.69 (8)	O1ⁱ—Na1—O2—C6	44.03 (18)
O2—Na1—Na2—O4ⁱⁱⁱ	91.64 (8)	Na2—Na1—O2—C6	−131.8 (2)
O2ⁱ—Na1—Na2—O4ⁱⁱⁱ	−88.36 (8)	Na2ⁱⁱ—Na1—O2—C6	48.2 (2)
O3—Na1—Na2—O4	−0.53 (7)	O3—Na1—O2—Na2	−93.36 (6)
O3ⁱ—Na1—Na2—O4	179.47 (7)	O3ⁱ—Na1—O2—Na2	86.64 (6)
O1—Na1—Na2—O4	85.69 (8)	O1—Na1—O2—Na2	−4.18 (6)
O1ⁱ—Na1—Na2—O4	−94.31 (8)	O1ⁱ—Na1—O2—Na2	175.82 (6)
O2—Na1—Na2—O4	−88.36 (8)	Na2ⁱⁱ—Na1—O2—Na2	180.0
O2ⁱ—Na1—Na2—O4	91.64 (8)	O1—Na1—O3—C11	15.4 (2)
O3—Na1—Na2—O2	87.84 (8)	O1ⁱ—Na1—O3—C11	−164.6 (2)
O3ⁱ—Na1—Na2—O2	−92.16 (8)	O2—Na1—O3—C11	101.3 (2)
O1—Na1—Na2—O2	174.06 (9)	O2ⁱ—Na1—O3—C11	−78.7 (2)
O1ⁱ—Na1—Na2—O2	−5.95 (9)	Na2—Na1—O3—C11	59.9 (2)
O2ⁱ—Na1—Na2—O2	180.0	Na2ⁱⁱ—Na1—O3—C11	−120.1 (2)
O3—Na1—Na2—O2ⁱⁱⁱ	−92.17 (8)	O2—Na2—O4—C16	13.2 (2)
O3ⁱ—Na1—Na2—O2ⁱⁱⁱ	87.84 (8)	O2ⁱⁱⁱ—Na2—O4—C16	−166.8 (2)
O1—Na1—Na2—O2ⁱⁱⁱ	−5.94 (9)	O1—Na2—O4—C16	98.2 (2)
O1ⁱ—Na1—Na2—O2ⁱⁱⁱ	174.05 (9)	O1ⁱⁱⁱ—Na2—O4—C16	−81.8 (2)
O2—Na1—Na2—O2ⁱⁱⁱ	180.0	Na1^iv—Na2—O4—C16	−123.4 (2)
O2ⁱ—Na1—Na2—O2ⁱⁱⁱ	0.0	Na1—Na2—O4—C16	56.6 (2)
O3—Na1—Na2—O1	−86.22 (8)	Na1—O1—C1—N1	−23.0 (3)
O3ⁱ—Na1—Na2—O1	93.78 (8)	Na2—O1—C1—N1	85.7 (2)
O1ⁱ—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)
O2ⁱ—Na1—Na2—O1	5.94 (9)	C5—N1—C1—O1	−177.1 (2)
O3—Na1—Na2—O1ⁱⁱⁱ	93.78 (8)	C5—N1—C1—C2	2.3 (4)
O3ⁱ—Na1—Na2—O1ⁱⁱⁱ	−86.22 (8)	O1—C1—C2—C3	177.4 (3)
O1—Na1—Na2—O1ⁱⁱⁱ	180.0	N1—C1—C2—C3	−1.9 (4)
O1ⁱ—Na1—Na2—O1ⁱⁱⁱ	0.0	C1—C2—C3—C4	0.7 (4)
O2—Na1—Na2—O1ⁱⁱⁱ	5.95 (9)	C2—C3—C4—C5	0.4 (5)
O2ⁱ—Na1—Na2—O1ⁱⁱⁱ	−174.05 (9)	C3—C4—C5—N1	−0.2 (4)
O3—Na1—O1—C1	−149.7 (2)	C1—N1—C5—C4	−1.3 (4)
O3ⁱ—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)
O2ⁱ—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)
Na2ⁱⁱ—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)
O3ⁱ—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)
O2ⁱ—Na1—O1—Na2	−176.05 (6)	C6—C7—C8—C9	−0.8 (4)
Na2ⁱⁱ—Na1—O1—Na2	180.0	C7—C8—C9—C10	0.2 (5)
O4ⁱⁱⁱ—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)
O2ⁱⁱⁱ—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)
O4ⁱⁱⁱ—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)
O2ⁱⁱⁱ—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)
O4ⁱⁱⁱ—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)
O1ⁱⁱⁱ—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)
O4ⁱⁱⁱ—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)
O1ⁱⁱⁱ—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) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3ⁱ	0.82 (3)	1.97 (3)	2.772 (3)	168 (3)
N2—H2N···O4ⁱⁱⁱ	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.

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page