Tris(1,2-di­methoxy­ethane-O,O')­sodium penta­phenyl­cyclo­pentadienide

The title compound, [Na(C₄H₁₀O₂)₃](C₃₅H₂₅), is the first penta­phenyl­cyclo­pentadienide salt with an isolated anion. Solvent-separated sodium cations and penta­phenyl­cyclo­pentadienide anions alternate with each other in stacks parallel to the b axis and are arranged in segregated stacks along the a direction.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.051
• wR factor = 0.152
• Data-to-parameter ratio = 14.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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S1. Comment

Since 1973 (Ban et al., 1973) well over 40 complexes containing η-bonds between the pentaphenylcyclopentadienide anion and metal cations have been crystallized. Their structural properties are largely determined by the extended substituents of the cyclopentadienyl ligand. Here, the structure of the first pentaphenylcyclopentadienide anion salt, (I), with an isolated cation is reported.

In the title compound, (I), the isolated anions and solvent-separated metal cations alternate with each other in stacks along the b axis and are arranged in segregated stacks along the a axis (Fig. 2). The six Na⁺···O contacts range between 2.3098 (18) and 2.4254 (17) Å. The planar five-membered ring of the cyclopentadienide anion exhibits bond lengths and angles from 1.408 (2) to 1.423 (2) Å and from 107.21 (14) to 108.61 (14)°. The exocyclic bond lengths to the phenyl substituents of 1.467 (2) and 1.482 (2) Å are in accordance with the literature (Baghdadi et al., 1992) and the same applies for bond lengths and angles within the phenyl rings. The torsion between the phenyl groups and the cyclopentadienyl ring of 33.3 (3) to 62.0 (3)° excludes considerable π-delocalization of the negative charge into the substituents.

S2. Experimental

A metal mirror from 170 mg (7.4 mmol) sodium is generated in a Schlenk trap by heating at 10^-4 mbar 70 mg (0.16 mmol) pentaphenylcyclopentadiene and 3 ml dimethoxyethane are added. After 2 d, the solution is covered with 10 ml n-hexane and colourless prisms of (I) grow on the bottom of the vessel.

S3. Refinement

All H atoms were located from the difference map and placed on idealized positions using a riding model with phenyl C—H = 0.95 Å, methylene C—H = 0.99 Å and methyl C—H = 0.98 Å. The torsion of the methyl H atoms and the isotropic displacement parameters of all H atoms were refined.

Computing details

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1990); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The structure of (I) showing 50% probability displacement ellipsoides and a partial atom-labelling scheme. H atoms have been omitted for clarity.
	Fig. 2. View of the crystal packing of (I) down the b axis.

Tris(1,2-dimethoxyethane-O,O')sodium pentaphenylcyclopentadienide

Crystal data

[Na(C4H10O2)3](C35H25)	Z = 2
Mr = 738.90	F(000) = 792
Triclinic, P1	Dx = 1.163 Mg m^−3
a = 10.222 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.594 (2) Å	Cell parameters from 96 reflections
c = 17.301 (3) Å	θ = 9–19.5°
α = 79.050 (11)°	µ = 0.08 mm^−1
β = 85.982 (14)°	T = 150 K
γ = 74.883 (9)°	Prism, colorless
V = 2110.5 (5) Å^3	0.58 × 0.52 × 0.44 mm

Data collection

Siemens P4 four-circle diffractometer	Rint = 0.031
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 1.9°
Graphite monochromator	h = −1→12
ω scans	k = −14→14
8706 measured reflections	l = −20→20
7352 independent reflections	4 standard reflections every 100 reflections
6096 reflections with I > 2σ(I)	intensity decay: <5%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.152	w = 1/[σ^2(Fo^2) + (0.0859P)^2 + 0.6487P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
7352 reflections	Δρmax = 0.41 e Å^−3
494 parameters	Δρmin = −0.46 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0111 (17)

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 (Ų)

	x	y	z	Uiso*/Ueq
Na1	0.81310 (7)	0.78781 (6)	0.23102 (4)	0.0359 (2)
C1	1.18030 (16)	0.72813 (14)	0.66651 (10)	0.0247 (4)
C2	1.04458 (16)	0.76684 (14)	0.69165 (10)	0.0250 (4)
C3	1.04034 (17)	0.75374 (14)	0.77496 (10)	0.0256 (4)
C4	1.17544 (17)	0.70634 (14)	0.80103 (10)	0.0261 (4)
C5	1.26136 (16)	0.68980 (14)	0.73476 (10)	0.0255 (4)
C11	1.22970 (17)	0.73484 (14)	0.58447 (10)	0.0265 (4)
C12	1.35116 (18)	0.76451 (15)	0.56145 (11)	0.0326 (4)
H12	1.4019	0.7805	0.5998	0.039*
C13	1.3993 (2)	0.77124 (19)	0.48489 (12)	0.0435 (5)
H13	1.4833	0.7898	0.4714	0.052*
C14	1.3262 (2)	0.7513 (2)	0.42764 (13)	0.0517 (6)
H14	1.3587	0.7570	0.3746	0.062*
C15	1.2053 (2)	0.7229 (2)	0.44840 (12)	0.0475 (5)
H15	1.1541	0.7092	0.4093	0.057*
C16	1.15818 (19)	0.71411 (17)	0.52521 (11)	0.0345 (4)
H16	1.0753	0.6935	0.5383	0.041*
C21	0.92624 (16)	0.81110 (14)	0.63989 (10)	0.0263 (4)
C22	0.91300 (19)	0.90790 (16)	0.58419 (11)	0.0340 (4)
H22	0.9834	0.9456	0.5772	0.041*
C23	0.7987 (2)	0.95066 (18)	0.53845 (12)	0.0447 (5)
H23	0.7911	1.0172	0.5006	0.054*
C24	0.6959 (2)	0.8966 (2)	0.54801 (13)	0.0502 (6)
H24	0.6165	0.9266	0.5176	0.060*
C25	0.7087 (2)	0.7992 (2)	0.60168 (13)	0.0454 (5)
H25	0.6392	0.7607	0.6074	0.055*
C26	0.82235 (18)	0.75716 (17)	0.64728 (11)	0.0347 (4)
H26	0.8297	0.6900	0.6845	0.042*
C31	0.91656 (17)	0.77595 (15)	0.82416 (10)	0.0276 (4)
C32	0.80321 (19)	0.86387 (16)	0.79946 (11)	0.0339 (4)
H32	0.8099	0.9152	0.7523	0.041*
C33	0.6818 (2)	0.87768 (19)	0.84198 (12)	0.0428 (5)
H33	0.6066	0.9373	0.8233	0.051*
C34	0.6693 (2)	0.8057 (2)	0.91117 (12)	0.0448 (5)
H34	0.5853	0.8139	0.9395	0.054*
C35	0.7809 (2)	0.72164 (19)	0.93863 (11)	0.0399 (5)
H35	0.7744	0.6731	0.9872	0.048*
C36	0.90224 (18)	0.70722 (16)	0.89628 (11)	0.0322 (4)
H36	0.9778	0.6491	0.9167	0.039*
C41	1.22033 (17)	0.68238 (15)	0.88358 (10)	0.0288 (4)
C42	1.2026 (2)	0.76793 (18)	0.92623 (12)	0.0409 (5)
H42	1.1575	0.8419	0.9029	0.049*
C43	1.2493 (2)	0.7479 (2)	1.00212 (13)	0.0504 (6)
H43	1.2377	0.8083	1.0297	0.061*
C44	1.3122 (2)	0.6417 (2)	1.03775 (12)	0.0479 (5)
H44	1.3436	0.6281	1.0900	0.057*
C45	1.3294 (2)	0.55487 (19)	0.99715 (12)	0.0433 (5)
H45	1.3720	0.4808	1.0216	0.052*
C46	1.28463 (19)	0.57545 (17)	0.92066 (11)	0.0352 (4)
H46	1.2983	0.5150	0.8930	0.042*
C51	1.40755 (17)	0.63423 (14)	0.73677 (10)	0.0264 (4)
C52	1.49551 (18)	0.65777 (16)	0.78529 (10)	0.0303 (4)
H52	1.4613	0.7129	0.8172	0.036*
C53	1.63187 (18)	0.60251 (17)	0.78797 (11)	0.0364 (4)
H53	1.6893	0.6192	0.8223	0.044*
C54	1.68474 (18)	0.52372 (17)	0.74130 (12)	0.0390 (5)
H54	1.7782	0.4857	0.7434	0.047*
C55	1.60023 (19)	0.50055 (16)	0.69128 (13)	0.0389 (5)
H55	1.6361	0.4477	0.6578	0.047*
C56	1.46365 (18)	0.55413 (15)	0.68981 (11)	0.0331 (4)
H56	1.4066	0.5360	0.6560	0.040*
C61	0.7961 (4)	0.6778 (3)	0.42306 (16)	0.0812 (9)
H61A	0.7540	0.6245	0.4579	0.122*
H61B	0.7398	0.7539	0.4227	0.122*
H61C	0.8864	0.6715	0.4421	0.122*
O61	0.80792 (16)	0.65402 (13)	0.34549 (9)	0.0518 (4)
C62	0.8953 (3)	0.5478 (2)	0.33995 (16)	0.0616 (7)
H62A	0.8614	0.4888	0.3754	0.074*
H62B	0.9873	0.5442	0.3566	0.074*
C63	0.9012 (3)	0.52863 (18)	0.25800 (15)	0.0556 (6)
H63A	0.9620	0.4544	0.2541	0.067*
H63B	0.8097	0.5304	0.2416	0.067*
O62	0.95052 (15)	0.61344 (12)	0.20852 (9)	0.0455 (4)
C64	0.9849 (3)	0.5890 (2)	0.13174 (15)	0.0591 (6)
H64A	1.0092	0.6531	0.0979	0.089*
H64B	0.9071	0.5739	0.1098	0.089*
H64C	1.0620	0.5232	0.1345	0.089*
C71	0.5987 (3)	0.9964 (2)	0.31228 (16)	0.0636 (7)
H71A	0.5354	0.9578	0.2972	0.095*
H71B	0.5673	1.0768	0.2921	0.095*
H71C	0.6031	0.9838	0.3698	0.095*
O71	0.72891 (16)	0.95463 (14)	0.28018 (11)	0.0584 (5)
C72	0.8286 (3)	0.9967 (2)	0.30462 (18)	0.0634 (7)
H72A	0.8391	0.9716	0.3622	0.076*
H72B	0.7986	1.0794	0.2945	0.076*
C73	0.9591 (3)	0.9628 (2)	0.2660 (2)	0.0691 (8)
H73A	0.9591	1.0128	0.2144	0.083*
H73B	1.0295	0.9735	0.2982	0.083*
O72	0.99428 (17)	0.85452 (16)	0.25396 (13)	0.0680 (5)
C74	1.1262 (2)	0.8186 (3)	0.22443 (18)	0.0660 (7)
H74A	1.1446	0.7394	0.2204	0.099*
H74B	1.1909	0.8284	0.2600	0.099*
H74C	1.1355	0.8628	0.1722	0.099*
C81	0.5254 (3)	0.7170 (2)	0.22133 (16)	0.0607 (7)
H81A	0.5516	0.6853	0.2759	0.091*
H81B	0.5523	0.6583	0.1892	0.091*
H81C	0.4270	0.7478	0.2194	0.091*
O81	0.59123 (14)	0.80355 (13)	0.19155 (8)	0.0447 (4)
C82	0.5658 (2)	0.8468 (2)	0.11125 (13)	0.0490 (5)
H82A	0.4691	0.8871	0.1044	0.059*
H82B	0.5860	0.7850	0.0809	0.059*
C83	0.6526 (2)	0.9243 (2)	0.08196 (14)	0.0496 (5)
H83A	0.6351	0.9565	0.0257	0.060*
H83B	0.6324	0.9863	0.1121	0.060*
O82	0.78962 (15)	0.86315 (12)	0.09142 (8)	0.0458 (4)
C84	0.8801 (3)	0.9130 (2)	0.04076 (15)	0.0547 (6)
H84A	0.9730	0.8670	0.0496	0.082*
H84B	0.8734	0.9878	0.0516	0.082*
H84C	0.8567	0.9187	−0.0141	0.082*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Na1	0.0337 (4)	0.0319 (4)	0.0429 (4)	−0.0071 (3)	−0.0030 (3)	−0.0097 (3)
C1	0.0201 (8)	0.0267 (8)	0.0281 (8)	−0.0058 (7)	−0.0015 (6)	−0.0065 (7)
C2	0.0199 (8)	0.0271 (8)	0.0279 (8)	−0.0056 (6)	−0.0020 (6)	−0.0047 (7)
C3	0.0211 (8)	0.0268 (8)	0.0281 (9)	−0.0043 (7)	−0.0015 (7)	−0.0052 (7)
C4	0.0216 (8)	0.0285 (8)	0.0282 (9)	−0.0045 (7)	−0.0029 (7)	−0.0068 (7)
C5	0.0191 (8)	0.0276 (8)	0.0303 (9)	−0.0047 (7)	−0.0023 (6)	−0.0073 (7)
C11	0.0223 (8)	0.0271 (8)	0.0288 (9)	−0.0035 (7)	0.0004 (7)	−0.0057 (7)
C12	0.0250 (9)	0.0370 (10)	0.0347 (10)	−0.0063 (7)	0.0009 (7)	−0.0066 (8)
C13	0.0320 (10)	0.0541 (13)	0.0436 (11)	−0.0123 (9)	0.0108 (9)	−0.0088 (10)
C14	0.0507 (13)	0.0713 (15)	0.0321 (11)	−0.0139 (12)	0.0145 (10)	−0.0143 (10)
C15	0.0447 (12)	0.0697 (15)	0.0324 (10)	−0.0143 (11)	0.0000 (9)	−0.0199 (10)
C16	0.0285 (9)	0.0449 (11)	0.0320 (9)	−0.0096 (8)	0.0000 (7)	−0.0112 (8)
C21	0.0198 (8)	0.0324 (9)	0.0261 (8)	−0.0034 (7)	−0.0002 (6)	−0.0084 (7)
C22	0.0315 (10)	0.0371 (10)	0.0312 (9)	−0.0059 (8)	−0.0027 (7)	−0.0040 (8)
C23	0.0426 (12)	0.0461 (12)	0.0345 (10)	0.0045 (9)	−0.0082 (9)	0.0003 (9)
C24	0.0294 (11)	0.0714 (15)	0.0415 (12)	0.0049 (10)	−0.0144 (9)	−0.0097 (11)
C25	0.0238 (10)	0.0707 (15)	0.0447 (12)	−0.0131 (9)	−0.0052 (8)	−0.0143 (11)
C26	0.0261 (9)	0.0434 (11)	0.0348 (10)	−0.0106 (8)	−0.0031 (7)	−0.0043 (8)
C31	0.0230 (9)	0.0325 (9)	0.0290 (9)	−0.0061 (7)	−0.0020 (7)	−0.0104 (7)
C32	0.0279 (9)	0.0403 (10)	0.0309 (9)	−0.0029 (8)	0.0008 (7)	−0.0081 (8)
C33	0.0249 (10)	0.0595 (13)	0.0401 (11)	0.0032 (9)	−0.0011 (8)	−0.0187 (10)
C34	0.0271 (10)	0.0745 (15)	0.0342 (10)	−0.0098 (10)	0.0072 (8)	−0.0202 (10)
C35	0.0375 (11)	0.0582 (13)	0.0273 (9)	−0.0171 (9)	0.0041 (8)	−0.0108 (9)
C36	0.0270 (9)	0.0400 (10)	0.0307 (9)	−0.0072 (8)	−0.0014 (7)	−0.0106 (8)
C41	0.0184 (8)	0.0385 (10)	0.0287 (9)	−0.0056 (7)	−0.0006 (7)	−0.0062 (7)
C42	0.0414 (11)	0.0430 (11)	0.0362 (10)	−0.0013 (9)	−0.0079 (9)	−0.0122 (9)
C43	0.0514 (13)	0.0643 (15)	0.0368 (11)	−0.0065 (11)	−0.0079 (10)	−0.0207 (10)
C44	0.0387 (11)	0.0760 (16)	0.0269 (10)	−0.0126 (11)	−0.0079 (8)	−0.0039 (10)
C45	0.0333 (11)	0.0530 (12)	0.0376 (11)	−0.0087 (9)	−0.0083 (8)	0.0067 (9)
C46	0.0287 (10)	0.0387 (10)	0.0366 (10)	−0.0071 (8)	−0.0037 (8)	−0.0034 (8)
C51	0.0212 (8)	0.0283 (8)	0.0289 (9)	−0.0058 (7)	−0.0009 (7)	−0.0033 (7)
C52	0.0236 (9)	0.0366 (10)	0.0310 (9)	−0.0079 (7)	−0.0011 (7)	−0.0057 (7)
C53	0.0232 (9)	0.0484 (11)	0.0364 (10)	−0.0109 (8)	−0.0041 (7)	−0.0006 (8)
C54	0.0190 (9)	0.0401 (11)	0.0511 (12)	−0.0027 (8)	0.0011 (8)	0.0009 (9)
C55	0.0284 (10)	0.0324 (10)	0.0526 (12)	−0.0016 (8)	0.0060 (8)	−0.0104 (9)
C56	0.0253 (9)	0.0339 (10)	0.0410 (10)	−0.0056 (7)	−0.0017 (8)	−0.0106 (8)
C61	0.087 (2)	0.101 (2)	0.0514 (16)	−0.0161 (18)	0.0102 (15)	−0.0160 (15)
O61	0.0529 (9)	0.0504 (9)	0.0482 (9)	−0.0100 (7)	0.0012 (7)	−0.0041 (7)
C62	0.0674 (17)	0.0439 (13)	0.0641 (16)	−0.0067 (12)	−0.0076 (13)	0.0053 (11)
C63	0.0618 (15)	0.0313 (11)	0.0740 (16)	−0.0114 (10)	−0.0068 (12)	−0.0084 (11)
O62	0.0449 (8)	0.0352 (7)	0.0574 (9)	−0.0082 (6)	0.0024 (7)	−0.0149 (7)
C64	0.0567 (15)	0.0559 (14)	0.0648 (15)	−0.0046 (12)	0.0038 (12)	−0.0267 (12)
C71	0.0483 (14)	0.0703 (17)	0.0668 (16)	0.0085 (12)	−0.0055 (12)	−0.0301 (13)
O71	0.0468 (9)	0.0526 (9)	0.0824 (12)	−0.0058 (7)	−0.0006 (8)	−0.0383 (9)
C72	0.0684 (17)	0.0580 (15)	0.0800 (18)	−0.0280 (13)	0.0101 (14)	−0.0392 (14)
C73	0.0689 (18)	0.0592 (15)	0.096 (2)	−0.0291 (14)	0.0045 (15)	−0.0385 (15)
O72	0.0409 (9)	0.0678 (11)	0.1100 (15)	−0.0196 (8)	0.0065 (9)	−0.0467 (11)
C74	0.0397 (13)	0.0850 (19)	0.0766 (18)	−0.0125 (13)	0.0018 (12)	−0.0283 (15)
C81	0.0436 (13)	0.0827 (18)	0.0616 (15)	−0.0293 (13)	0.0079 (11)	−0.0115 (13)
O81	0.0379 (8)	0.0600 (9)	0.0394 (8)	−0.0159 (7)	0.0014 (6)	−0.0123 (7)
C82	0.0387 (12)	0.0640 (14)	0.0420 (12)	−0.0057 (10)	−0.0053 (9)	−0.0122 (10)
C83	0.0450 (12)	0.0494 (12)	0.0453 (12)	0.0016 (10)	−0.0040 (10)	−0.0037 (10)
O82	0.0406 (8)	0.0472 (8)	0.0445 (8)	−0.0073 (7)	0.0047 (6)	−0.0027 (7)
C84	0.0573 (15)	0.0534 (14)	0.0580 (14)	−0.0249 (11)	0.0130 (11)	−0.0111 (11)

Geometric parameters (Å, º)

Na1—O72	2.3098 (18)	C32—C33	1.385 (3)
Na1—O71	2.3477 (16)	C33—C34	1.377 (3)
Na1—O61	2.3512 (17)	C34—C35	1.380 (3)
Na1—O81	2.3623 (16)	C35—C36	1.383 (3)
Na1—O62	2.3636 (16)	C41—C42	1.386 (3)
Na1—O82	2.4254 (17)	C41—C46	1.388 (3)
Na1—C63	3.103 (2)	C42—C43	1.384 (3)
Na1—C83	3.120 (2)	C43—C44	1.370 (3)
C1—C2	1.412 (2)	C44—C45	1.376 (3)
C1—C5	1.423 (2)	C45—C46	1.386 (3)
C1—C11	1.467 (2)	C51—C52	1.393 (3)
C2—C3	1.418 (2)	C51—C56	1.397 (3)
C2—C21	1.479 (2)	C52—C53	1.386 (3)
C3—C4	1.422 (2)	C53—C54	1.375 (3)
C3—C31	1.469 (2)	C54—C55	1.383 (3)
C4—C5	1.408 (2)	C55—C56	1.383 (3)
C4—C41	1.482 (2)	C61—O61	1.420 (3)
C5—C51	1.475 (2)	O61—C62	1.418 (3)
C11—C12	1.399 (2)	C62—C63	1.477 (4)
C11—C16	1.400 (3)	C63—O62	1.415 (3)
C12—C13	1.375 (3)	O62—C64	1.420 (3)
C13—C14	1.378 (3)	C71—O71	1.414 (3)
C14—C15	1.380 (3)	O71—C72	1.388 (3)
C15—C16	1.376 (3)	C72—C73	1.447 (4)
C21—C22	1.385 (3)	C73—O72	1.369 (3)
C21—C26	1.389 (3)	O72—C74	1.399 (3)
C22—C23	1.386 (3)	C81—O81	1.424 (3)
C23—C24	1.379 (3)	O81—C82	1.408 (3)
C24—C25	1.373 (3)	C82—C83	1.482 (3)
C25—C26	1.379 (3)	C83—O82	1.415 (3)
C31—C36	1.399 (3)	O82—C84	1.413 (3)
C31—C32	1.404 (3)
O72—Na1—O71	71.55 (6)	C25—C24—C23	119.73 (18)
O72—Na1—O61	101.77 (8)	C24—C25—C26	120.1 (2)
O71—Na1—O61	101.13 (7)	C25—C26—C21	121.31 (19)
O72—Na1—O81	155.17 (7)	C36—C31—C32	116.19 (16)
O71—Na1—O81	88.29 (6)	C36—C31—C3	121.93 (16)
O61—Na1—O81	96.12 (6)	C32—C31—C3	121.80 (16)
O72—Na1—O62	94.10 (6)	C33—C32—C31	121.72 (18)
O71—Na1—O62	162.57 (7)	C34—C33—C32	120.62 (19)
O61—Na1—O62	71.51 (6)	C33—C34—C35	118.83 (18)
O81—Na1—O62	107.93 (6)	C34—C35—C36	120.76 (19)
O72—Na1—O82	98.57 (7)	C35—C36—C31	121.75 (18)
O71—Na1—O82	98.87 (7)	C42—C41—C46	117.23 (17)
O61—Na1—O82	155.07 (7)	C42—C41—C4	120.57 (17)
O81—Na1—O82	69.68 (5)	C46—C41—C4	122.18 (16)
O62—Na1—O82	92.89 (6)	C43—C42—C41	121.4 (2)
O72—Na1—C63	109.18 (7)	C44—C43—C42	120.5 (2)
O71—Na1—C63	150.25 (8)	C43—C44—C45	119.38 (19)
O61—Na1—C63	49.15 (6)	C44—C45—C46	120.0 (2)
O81—Na1—C63	95.53 (7)	C45—C46—C41	121.50 (19)
O62—Na1—C63	25.73 (6)	C52—C51—C56	116.95 (16)
O82—Na1—C63	110.14 (7)	C52—C51—C5	122.28 (16)
O72—Na1—C83	112.95 (8)	C56—C51—C5	120.77 (15)
O71—Na1—C83	83.33 (7)	C53—C52—C51	121.44 (18)
O61—Na1—C83	144.41 (7)	C54—C53—C52	120.54 (18)
O81—Na1—C83	48.44 (6)	C53—C54—C55	119.19 (17)
O62—Na1—C83	112.03 (6)	C56—C55—C54	120.20 (18)
O82—Na1—C83	25.90 (5)	C55—C56—C51	121.64 (18)
C63—Na1—C83	120.79 (7)	C62—O61—C61	113.0 (2)
C2—C1—C5	107.71 (14)	C62—O61—Na1	112.86 (14)
C2—C1—C11	125.86 (15)	C61—O61—Na1	124.05 (18)
C5—C1—C11	126.26 (15)	O61—C62—C63	109.8 (2)
C1—C2—C3	108.61 (14)	O62—C63—C62	108.69 (19)
C1—C2—C21	125.69 (15)	O62—C63—Na1	46.49 (9)
C3—C2—C21	125.69 (15)	C62—C63—Na1	79.42 (13)
C2—C3—C4	107.21 (14)	C63—O62—C64	112.10 (18)
C2—C3—C31	125.38 (15)	C63—O62—Na1	107.78 (13)
C4—C3—C31	127.19 (15)	C64—O62—Na1	122.61 (14)
C5—C4—C3	108.56 (15)	C72—O71—C71	113.70 (19)
C5—C4—C41	125.27 (15)	C72—O71—Na1	113.99 (14)
C3—C4—C41	126.13 (15)	C71—O71—Na1	128.58 (16)
C4—C5—C1	107.91 (14)	O71—C72—C73	113.9 (2)
C4—C5—C51	125.61 (15)	O72—C73—C72	115.1 (2)
C1—C5—C51	126.31 (15)	C73—O72—C74	114.8 (2)
C12—C11—C16	116.53 (16)	C73—O72—Na1	114.19 (16)
C12—C11—C1	120.96 (16)	C74—O72—Na1	124.87 (16)
C16—C11—C1	122.51 (16)	C82—O81—C81	112.25 (18)
C13—C12—C11	121.89 (18)	C82—O81—Na1	115.29 (12)
C12—C13—C14	120.32 (19)	C81—O81—Na1	119.95 (14)
C13—C14—C15	119.11 (19)	O81—C82—C83	108.94 (18)
C16—C15—C14	120.7 (2)	O82—C83—C82	108.10 (18)
C15—C16—C11	121.47 (18)	O82—C83—Na1	48.47 (9)
C22—C21—C26	117.77 (16)	C82—C83—Na1	80.51 (12)
C22—C21—C2	121.91 (16)	C84—O82—C83	113.08 (18)
C26—C21—C2	120.30 (16)	C84—O82—Na1	127.61 (15)
C21—C22—C23	121.07 (19)	C83—O82—Na1	105.62 (12)
C24—C23—C22	120.0 (2)
C5—C1—C2—C3	0.41 (19)	C4—C3—C31—C36	−33.3 (3)
C11—C1—C2—C3	−175.10 (16)	C2—C3—C31—C32	−35.9 (3)
C5—C1—C2—C21	−178.24 (16)	C4—C3—C31—C32	150.23 (18)
C11—C1—C2—C21	6.3 (3)	C36—C31—C32—C33	−3.6 (3)
C1—C2—C3—C4	−0.01 (19)	C3—C31—C32—C33	173.16 (18)
C21—C2—C3—C4	178.64 (16)	C31—C32—C33—C34	1.0 (3)
C1—C2—C3—C31	−174.90 (16)	C32—C33—C34—C35	1.9 (3)
C21—C2—C3—C31	3.7 (3)	C33—C34—C35—C36	−2.1 (3)
C2—C3—C4—C5	−0.40 (19)	C34—C35—C36—C31	−0.6 (3)
C31—C3—C4—C5	174.37 (16)	C32—C31—C36—C35	3.3 (3)
C2—C3—C4—C41	177.26 (16)	C3—C31—C36—C35	−173.38 (17)
C31—C3—C4—C41	−8.0 (3)	C5—C4—C41—C42	116.1 (2)
C3—C4—C5—C1	0.66 (19)	C3—C4—C41—C42	−61.2 (3)
C41—C4—C5—C1	−177.03 (16)	C5—C4—C41—C46	−62.0 (3)
C3—C4—C5—C51	−174.90 (16)	C3—C4—C41—C46	120.7 (2)
C41—C4—C5—C51	7.4 (3)	C46—C41—C42—C43	1.2 (3)
C2—C1—C5—C4	−0.65 (19)	C4—C41—C42—C43	−177.06 (19)
C11—C1—C5—C4	174.83 (16)	C41—C42—C43—C44	−1.4 (4)
C2—C1—C5—C51	174.86 (16)	C42—C43—C44—C45	0.4 (4)
C11—C1—C5—C51	−9.7 (3)	C43—C44—C45—C46	0.7 (3)
C2—C1—C11—C12	138.31 (18)	C44—C45—C46—C41	−0.9 (3)
C5—C1—C11—C12	−36.4 (3)	C42—C41—C46—C45	0.0 (3)
C2—C1—C11—C16	−40.6 (3)	C4—C41—C46—C45	178.17 (17)
C5—C1—C11—C16	144.70 (18)	C4—C5—C51—C52	−45.6 (3)
C16—C11—C12—C13	−1.0 (3)	C1—C5—C51—C52	139.67 (18)
C1—C11—C12—C13	179.97 (18)	C4—C5—C51—C56	133.90 (19)
C11—C12—C13—C14	1.6 (3)	C1—C5—C51—C56	−40.8 (3)
C12—C13—C14—C15	−0.9 (4)	C56—C51—C52—C53	−1.3 (3)
C13—C14—C15—C16	−0.2 (4)	C5—C51—C52—C53	178.21 (17)
C14—C15—C16—C11	0.8 (3)	C51—C52—C53—C54	1.2 (3)
C12—C11—C16—C15	−0.1 (3)	C52—C53—C54—C55	0.3 (3)
C1—C11—C16—C15	178.82 (19)	C53—C54—C55—C56	−1.6 (3)
C1—C2—C21—C22	−63.7 (2)	C54—C55—C56—C51	1.5 (3)
C3—C2—C21—C22	117.9 (2)	C52—C51—C56—C55	0.0 (3)
C1—C2—C21—C26	117.8 (2)	C5—C51—C56—C55	−179.53 (17)
C3—C2—C21—C26	−60.6 (2)	C61—O61—C62—C63	179.4 (2)
C26—C21—C22—C23	1.2 (3)	O61—C62—C63—O62	59.7 (3)
C2—C21—C22—C23	−177.28 (17)	C62—C63—O62—C64	168.2 (2)
C21—C22—C23—C24	−0.1 (3)	C71—O71—C72—C73	−174.2 (3)
C22—C23—C24—C25	−1.4 (3)	O71—C72—C73—O72	−39.3 (4)
C23—C24—C25—C26	1.7 (3)	C72—C73—O72—C74	−173.5 (3)
C24—C25—C26—C21	−0.5 (3)	C81—O81—C82—C83	−172.01 (19)
C22—C21—C26—C25	−1.0 (3)	O81—C82—C83—O82	60.6 (2)
C2—C21—C26—C25	177.57 (18)	C82—C83—O82—C84	157.50 (19)
C2—C3—C31—C36	140.62 (18)