Bis{bis-[1-meth-oxy-2-(2-meth-oxy-eth-oxy)ethane-κ(3) O,O',O'']sodium} 1,1,2,2-tetra-phenyl-ethane-1,2-diide.

Crystals of the title salt, [Na(C6H14O3)2]2(C26H20), were grown from a tetra-hydro-furan/diglyme/Et2O solvent mixture [diglyme is 1-meth-oxy-2-(2-meth-oxy-eth-oxy)ethane]. The cations and dianion are separated in the crystal structure, unlike in the other three structurally characterized dialkali metal tetra-phenyl-ethyl-ene salts. The asymmetric unit contains one [Na(diglyme)2](+) cation and one half of the [Ph2CCPh2](2-) dianion. The latter lies on a twofold rotation axis. C-C bond-length redistribution displays that excessive electron density of the dianion is predominantly located at the C atoms of a former double bond and at all eight ortho positions. The studied crystal was a twin, with the ratio of two major components being 0.2143 (9):0.7857 (9). The twin operation is a twofold rotation around the a axis.

Related literature

For the crystal structure of free tetra­phenyl­ethyl­enide, see: Hua et al. (2007 ▶). For the preparation and reactivity of disodiumtetra­phenyl­ethyl­ene, see: Schlenk & Bergmann (1928 ▶). For UV–VIS data, see: Roberts & Szwarc (1965 ▶). For 1H and 13C{1H} NMR spectra, see: Roitershtein et al. (1998 ▶). For crystal structures of related alkali-metal tetra­phenyl­ethyl­ene salts, see: Bock et al. (1989 ▶, 1996 ▶); Minyaev et al. (2007 ▶). For crystal structures of hetero- and homoleptic d- and f-metal complexes with the tetra­phenyl­ethilene dianion, see: Roitershtein et al. (1998 ▶, 2004 ▶, 2007 ▶); Minyaev et al. (2007 ▶).

Experimental

Crystal data

[Na(C6H14O3)2]2(C26H20)

M = 915.08

Monoclinic,

a = 10.048 (2) Å

b = 24.165 (5) Å

c = 20.978 (4) Å

β = 92.92 (3)°

V = 5087.0 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 123 K

0.50 × 0.30 × 0.20 mm

Data collection

Siemens SMART Platform CCD diffractometer

Absorption correction: multi-scan (TWINABS; Bruker, 2003 ▶) T min = 0.657, T max = 0.746

6286 measured reflections

6286 independent reflections

5347 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.115

S = 1.06

6286 reflections

294 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: CELL_NOW (Sheldrick, 2003 ▶) and SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS2012 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL2012 (Sheldrick, 2008 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814012823/pj2012sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814012823/pj2012Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814012823/pj2012Isup3.cdx

CCDC reference: 1006312

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Na(C6H14O3)2]2(C26H20)	F(000) = 1976
Mr = 915.08	Dx = 1.195 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.048 (2) Å	Cell parameters from 4057 reflections
b = 24.165 (5) Å	θ = 2.2–28.2°
c = 20.978 (4) Å	µ = 0.10 mm−1
β = 92.92 (3)°	T = 123 K
V = 5087.0 (18) Å3	Block, red
Z = 4	0.50 × 0.30 × 0.20 mm

Siemens SMART Platform CCD diffractometer	6286 independent reflections
Radiation source: normal-focus sealed tube	5347 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.0
area detector, ω scans per phi	θmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan (TWINABS; Bruker, 2003)	h = −13→13
Tmin = 0.657, Tmax = 0.746	k = 0→32
6286 measured reflections	l = 0→27

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0435P)2 + 4.6083P] where P = (Fo2 + 2Fc2)/3
6286 reflections	(Δ/σ)max < 0.001
294 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Experimental. moisture and air sensitive

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. Refined as a 2-component twin. BASF=0.214

	x	y	z	Uiso*/Ueq
C1	0.42755 (17)	0.13927 (7)	0.25769 (8)	0.0214 (3)
C2	0.38922 (17)	0.17452 (7)	0.30886 (8)	0.0219 (3)
C3	0.47563 (19)	0.21800 (7)	0.33076 (8)	0.0251 (4)
H3	0.5576	0.2228	0.3108	0.030*
C4	0.4459 (2)	0.25360 (8)	0.37973 (9)	0.0326 (4)
H4	0.5062	0.2825	0.3915	0.039*
C5	0.3292 (2)	0.24769 (9)	0.41196 (9)	0.0379 (5)
H5	0.3084	0.2723	0.4453	0.045*
C6	0.2442 (2)	0.20449 (9)	0.39376 (9)	0.0346 (4)
H6	0.1654	0.1990	0.4162	0.042*
C7	0.27099 (19)	0.16925 (8)	0.34386 (8)	0.0273 (4)
H7	0.2091	0.1407	0.3325	0.033*
C8	0.33820 (18)	0.10525 (7)	0.21972 (8)	0.0221 (3)
C9	0.3903 (2)	0.06401 (7)	0.17867 (9)	0.0276 (4)
H9	0.4842	0.0598	0.1779	0.033*
C10	0.3100 (2)	0.03023 (8)	0.14016 (9)	0.0343 (4)
H10	0.3500	0.0033	0.1142	0.041*
C11	0.1720 (2)	0.03466 (9)	0.13839 (10)	0.0383 (5)
H11	0.1170	0.0109	0.1124	0.046*
C12	0.1172 (2)	0.07532 (9)	0.17626 (10)	0.0344 (5)
H12	0.0232	0.0797	0.1751	0.041*
C13	0.19548 (19)	0.10935 (8)	0.21528 (9)	0.0271 (4)
H13	0.1535	0.1365	0.2401	0.032*
Na1	0.19803 (8)	0.37669 (3)	0.10184 (3)	0.03106 (18)
C14	0.0899 (3)	0.25199 (9)	0.14723 (13)	0.0545 (7)
H14A	0.1255	0.2159	0.1610	0.082*
H14B	0.0679	0.2512	0.1012	0.082*
H14C	0.0093	0.2601	0.1700	0.082*
O1	0.18706 (16)	0.29378 (6)	0.16114 (6)	0.0393 (4)
C15	0.2176 (2)	0.29889 (11)	0.22790 (10)	0.0453 (6)
H15A	0.2590	0.2644	0.2448	0.054*
H15B	0.1352	0.3058	0.2506	0.054*
C16	0.3109 (2)	0.34577 (12)	0.23745 (10)	0.0499 (6)
H16A	0.3346	0.3508	0.2835	0.060*
H16B	0.3936	0.3387	0.2151	0.060*
O2	0.24528 (15)	0.39425 (7)	0.21202 (7)	0.0409 (4)
C17	0.3210 (3)	0.44350 (13)	0.21969 (12)	0.0576 (7)
H17A	0.4123	0.4375	0.2055	0.069*
H17B	0.3271	0.4546	0.2652	0.069*
C18	0.2538 (3)	0.48737 (10)	0.18068 (13)	0.0573 (7)
H18A	0.1606	0.4918	0.1930	0.069*
H18B	0.3006	0.5231	0.1876	0.069*
O3	0.25612 (17)	0.47153 (6)	0.11525 (8)	0.0458 (4)
C19	0.2039 (4)	0.51249 (11)	0.07319 (17)	0.0764 (9)
H19A	0.2505	0.5475	0.0817	0.115*
H19B	0.1086	0.5173	0.0796	0.115*
H19C	0.2161	0.5011	0.0290	0.115*
C20	0.4897 (3)	0.40361 (14)	0.03195 (17)	0.0767 (10)
H20A	0.5734	0.3834	0.0282	0.115*
H20B	0.4985	0.4292	0.0681	0.115*
H20C	0.4692	0.4245	−0.0074	0.115*
O4	0.38983 (16)	0.36721 (7)	0.04155 (8)	0.0476 (4)
C21	0.3632 (3)	0.32886 (12)	−0.00971 (13)	0.0573 (7)
H21A	0.3594	0.2908	0.0076	0.069*
H21B	0.4365	0.3303	−0.0395	0.069*
C22	0.2354 (2)	0.34211 (10)	−0.04470 (10)	0.0403 (5)
H22A	0.2401	0.3792	−0.0646	0.048*
H22B	0.2160	0.3145	−0.0788	0.048*
O5	0.13343 (14)	0.34110 (6)	0.00064 (6)	0.0321 (3)
C23	0.01609 (19)	0.36844 (9)	−0.02316 (9)	0.0316 (4)
H23A	−0.0179	0.3510	−0.0635	0.038*
H23B	0.0353	0.4079	−0.0317	0.038*
C24	−0.0849 (2)	0.36364 (10)	0.02655 (10)	0.0368 (5)
H24A	−0.1696	0.3812	0.0111	0.044*
H24B	−0.1026	0.3242	0.0355	0.044*
O6	−0.03470 (15)	0.39049 (6)	0.08320 (7)	0.0360 (3)
C25	−0.1223 (3)	0.38392 (10)	0.13393 (11)	0.0484 (6)
H25A	−0.2067	0.4028	0.1230	0.073*
H25B	−0.0813	0.4000	0.1731	0.073*
H25C	−0.1390	0.3444	0.1407	0.073*

	U11	U22	U33	U12	U13	U23
C1	0.0197 (8)	0.0234 (8)	0.0211 (8)	0.0002 (7)	0.0015 (6)	0.0031 (6)
C2	0.0211 (8)	0.0239 (8)	0.0205 (8)	0.0045 (7)	0.0005 (6)	0.0062 (6)
C3	0.0286 (9)	0.0264 (9)	0.0203 (8)	0.0018 (7)	0.0025 (7)	0.0014 (7)
C4	0.0408 (11)	0.0292 (10)	0.0277 (9)	0.0020 (8)	−0.0006 (8)	−0.0026 (8)
C5	0.0461 (13)	0.0394 (11)	0.0286 (10)	0.0145 (10)	0.0071 (9)	−0.0055 (8)
C6	0.0293 (10)	0.0475 (12)	0.0279 (9)	0.0123 (9)	0.0088 (8)	0.0050 (8)
C7	0.0239 (9)	0.0338 (9)	0.0242 (8)	0.0032 (7)	0.0025 (7)	0.0055 (7)
C8	0.0246 (9)	0.0210 (8)	0.0207 (8)	−0.0023 (7)	−0.0001 (7)	0.0072 (6)
C9	0.0327 (10)	0.0241 (9)	0.0257 (9)	−0.0016 (7)	−0.0008 (7)	0.0023 (7)
C10	0.0478 (12)	0.0259 (9)	0.0287 (9)	−0.0052 (9)	−0.0019 (9)	−0.0007 (7)
C11	0.0459 (13)	0.0334 (10)	0.0344 (10)	−0.0174 (9)	−0.0115 (9)	0.0032 (8)
C12	0.0259 (10)	0.0419 (11)	0.0346 (10)	−0.0100 (9)	−0.0060 (8)	0.0123 (9)
C13	0.0257 (9)	0.0286 (9)	0.0266 (9)	−0.0013 (7)	−0.0006 (7)	0.0073 (7)
Na1	0.0402 (4)	0.0287 (4)	0.0236 (3)	0.0006 (3)	−0.0053 (3)	−0.0037 (3)
C14	0.086 (2)	0.0275 (11)	0.0514 (14)	−0.0008 (12)	0.0215 (14)	−0.0041 (10)
O1	0.0509 (9)	0.0384 (8)	0.0292 (7)	0.0107 (7)	0.0063 (7)	0.0061 (6)
C15	0.0422 (13)	0.0667 (15)	0.0274 (10)	0.0218 (12)	0.0066 (9)	0.0130 (10)
C16	0.0314 (12)	0.0934 (19)	0.0245 (10)	0.0162 (12)	−0.0013 (8)	0.0027 (11)
O2	0.0330 (8)	0.0578 (9)	0.0316 (7)	0.0016 (7)	−0.0030 (6)	−0.0143 (7)
C17	0.0473 (14)	0.0851 (19)	0.0401 (12)	−0.0176 (14)	−0.0006 (11)	−0.0301 (13)
C18	0.0553 (15)	0.0454 (13)	0.0728 (17)	−0.0110 (12)	0.0181 (14)	−0.0372 (13)
O3	0.0510 (10)	0.0311 (7)	0.0546 (9)	0.0033 (7)	−0.0039 (8)	−0.0116 (7)
C19	0.093 (2)	0.0369 (14)	0.099 (2)	0.0093 (15)	0.008 (2)	0.0144 (15)
C20	0.075 (2)	0.0665 (19)	0.092 (2)	−0.0355 (16)	0.0292 (18)	−0.0306 (17)
O4	0.0354 (8)	0.0539 (10)	0.0535 (10)	−0.0069 (7)	0.0021 (7)	−0.0270 (8)
C21	0.0390 (13)	0.0708 (18)	0.0615 (16)	0.0057 (12)	−0.0025 (12)	−0.0355 (14)
C22	0.0356 (12)	0.0547 (13)	0.0308 (10)	0.0024 (10)	0.0043 (8)	−0.0084 (9)
O5	0.0291 (7)	0.0430 (8)	0.0240 (6)	0.0017 (6)	0.0002 (5)	−0.0018 (6)
C23	0.0302 (10)	0.0405 (11)	0.0237 (9)	−0.0031 (8)	−0.0026 (7)	0.0000 (8)
C24	0.0314 (11)	0.0467 (12)	0.0325 (10)	−0.0039 (9)	0.0025 (8)	−0.0009 (9)
O6	0.0396 (8)	0.0414 (8)	0.0277 (7)	0.0008 (6)	0.0075 (6)	−0.0005 (6)
C25	0.0632 (16)	0.0432 (12)	0.0411 (12)	0.0041 (11)	0.0258 (12)	0.0012 (10)

C1—C1i	1.507 (3)	C15—H15A	0.9900
C1—C2	1.438 (2)	C15—H15B	0.9900
C1—C8	1.429 (2)	C16—O2	1.434 (3)
C2—C3	1.424 (3)	C16—H16A	0.9900
C2—C7	1.434 (3)	C16—H16B	0.9900
C3—C4	1.384 (3)	O2—C17	1.417 (3)
C3—H3	0.9500	C17—C18	1.481 (4)
C4—C5	1.390 (3)	C17—H17A	0.9900
C4—H4	0.9500	C17—H17B	0.9900
C5—C6	1.390 (3)	C18—O3	1.426 (3)
C5—H5	0.9500	C18—H18A	0.9900
C6—C7	1.387 (3)	C18—H18B	0.9900
C6—H6	0.9500	O3—C19	1.410 (3)
C7—H7	0.9500	C19—H19A	0.9800
C8—C9	1.433 (3)	C19—H19B	0.9800
C8—C13	1.436 (3)	C19—H19C	0.9800
C9—C10	1.380 (3)	C20—O4	1.357 (3)
C9—H9	0.9500	C20—H20A	0.9800
C10—C11	1.389 (3)	C20—H20B	0.9800
C10—H10	0.9500	C20—H20C	0.9800
C11—C12	1.394 (3)	O4—C21	1.434 (3)
C11—H11	0.9500	C21—C22	1.481 (3)
C12—C13	1.378 (3)	C21—H21A	0.9900
C12—H12	0.9500	C21—H21B	0.9900
C13—H13	0.9500	C22—O5	1.434 (2)
Na1—O5	2.3510 (16)	C22—H22A	0.9900
Na1—O1	2.3639 (16)	C22—H22B	0.9900
Na1—O4	2.3694 (19)	O5—C23	1.420 (2)
Na1—O2	2.3742 (16)	C23—C24	1.496 (3)
Na1—O6	2.3747 (18)	C23—H23A	0.9900
Na1—O3	2.3781 (17)	C23—H23B	0.9900
Na1—C16	3.100 (2)	C24—O6	1.424 (3)
Na1—C23	3.126 (2)	C24—H24A	0.9900
C14—O1	1.425 (3)	C24—H24B	0.9900
C14—H14A	0.9800	O6—C25	1.424 (3)
C14—H14B	0.9800	C25—H25A	0.9800
C14—H14C	0.9800	C25—H25B	0.9800
O1—C15	1.424 (3)	C25—H25C	0.9800
C15—C16	1.478 (4)
C8—C1—C2	124.90 (16)	O2—C16—Na1	47.30 (8)
C8—C1—C1i	117.83 (15)	C15—C16—Na1	81.98 (12)
C2—C1—C1i	117.26 (15)	O2—C16—H16A	110.2
C3—C2—C7	114.07 (16)	C15—C16—H16A	110.2
C3—C2—C1	119.72 (15)	Na1—C16—H16A	157.5
C7—C2—C1	126.15 (16)	O2—C16—H16B	110.2
C4—C3—C2	123.15 (17)	C15—C16—H16B	110.2
C4—C3—H3	118.4	Na1—C16—H16B	83.3
C2—C3—H3	118.4	H16A—C16—H16B	108.5
C3—C4—C5	121.09 (19)	C17—O2—C16	114.22 (19)
C3—C4—H4	119.5	C17—O2—Na1	109.88 (13)
C5—C4—H4	119.5	C16—O2—Na1	106.35 (12)
C4—C5—C6	117.74 (18)	O2—C17—C18	108.2 (2)
C4—C5—H5	121.1	O2—C17—H17A	110.1
C6—C5—H5	121.1	C18—C17—H17A	110.1
C7—C6—C5	121.88 (19)	O2—C17—H17B	110.1
C7—C6—H6	119.1	C18—C17—H17B	110.1
C5—C6—H6	119.1	H17A—C17—H17B	108.4
C6—C7—C2	122.00 (18)	O3—C18—C17	108.06 (19)
C6—C7—H7	119.0	O3—C18—H18A	110.1
C2—C7—H7	119.0	C17—C18—H18A	110.1
C1—C8—C9	119.78 (16)	O3—C18—H18B	110.1
C1—C8—C13	126.40 (17)	C17—C18—H18B	110.1
C9—C8—C13	113.75 (16)	H18A—C18—H18B	108.4
C10—C9—C8	122.88 (19)	C19—O3—C18	112.9 (2)
C10—C9—H9	118.6	C19—O3—Na1	121.42 (17)
C8—C9—H9	118.6	C18—O3—Na1	110.89 (14)
C9—C10—C11	121.5 (2)	O3—C19—H19A	109.5
C9—C10—H10	119.2	O3—C19—H19B	109.5
C11—C10—H10	119.2	H19A—C19—H19B	109.5
C10—C11—C12	117.48 (18)	O3—C19—H19C	109.5
C10—C11—H11	121.3	H19A—C19—H19C	109.5
C12—C11—H11	121.3	H19B—C19—H19C	109.5
C13—C12—C11	121.95 (19)	O4—C20—H20A	109.5
C13—C12—H12	119.0	O4—C20—H20B	109.5
C11—C12—H12	119.0	H20A—C20—H20B	109.5
C12—C13—C8	122.37 (19)	O4—C20—H20C	109.5
C12—C13—H13	118.8	H20A—C20—H20C	109.5
C8—C13—H13	118.8	H20B—C20—H20C	109.5
O5—Na1—O1	98.46 (6)	C20—O4—C21	114.7 (2)
O5—Na1—O4	71.18 (6)	C20—O4—Na1	130.10 (17)
O1—Na1—O4	105.07 (7)	C21—O4—Na1	109.70 (14)
O5—Na1—O2	167.64 (6)	O4—C21—C22	110.8 (2)
O1—Na1—O2	69.60 (6)	O4—C21—H21A	109.5
O4—Na1—O2	114.15 (7)	C22—C21—H21A	109.5
O5—Na1—O6	71.24 (6)	O4—C21—H21B	109.5
O1—Na1—O6	97.69 (6)	C22—C21—H21B	109.5
O4—Na1—O6	138.30 (6)	H21A—C21—H21B	108.1
O2—Na1—O6	106.35 (6)	O5—C22—C21	107.37 (18)
O5—Na1—O3	120.94 (6)	O5—C22—H22A	110.2
O1—Na1—O3	140.56 (6)	C21—C22—H22A	110.2
O4—Na1—O3	87.41 (6)	O5—C22—H22B	110.2
O2—Na1—O3	71.15 (6)	C21—C22—H22B	110.2
O6—Na1—O3	96.77 (6)	H22A—C22—H22B	108.5
O5—Na1—C16	144.27 (7)	C23—O5—C22	111.57 (15)
O1—Na1—C16	48.50 (7)	C23—O5—Na1	109.48 (11)
O4—Na1—C16	101.37 (7)	C22—O5—Na1	114.77 (12)
O2—Na1—C16	26.35 (6)	O5—C23—C24	107.43 (16)
O6—Na1—C16	119.74 (6)	O5—C23—Na1	45.17 (8)
O3—Na1—C16	92.73 (7)	C24—C23—Na1	78.98 (11)
O5—Na1—C23	25.36 (5)	O5—C23—H23A	110.2
O1—Na1—C23	110.27 (6)	C24—C23—H23A	110.2
O4—Na1—C23	90.17 (6)	Na1—C23—H23A	154.8
O2—Na1—C23	155.18 (6)	O5—C23—H23B	110.2
O6—Na1—C23	48.84 (5)	C24—C23—H23B	110.2
O3—Na1—C23	106.88 (6)	Na1—C23—H23B	88.8
C16—Na1—C23	157.75 (7)	H23A—C23—H23B	108.5
O1—C14—H14A	109.5	O6—C24—C23	108.80 (17)
O1—C14—H14B	109.5	O6—C24—H24A	109.9
H14A—C14—H14B	109.5	C23—C24—H24A	109.9
O1—C14—H14C	109.5	O6—C24—H24B	109.9
H14A—C14—H14C	109.5	C23—C24—H24B	109.9
H14B—C14—H14C	109.5	H24A—C24—H24B	108.3
C15—O1—C14	111.96 (18)	C24—O6—C25	111.52 (18)
C15—O1—Na1	115.51 (14)	C24—O6—Na1	112.19 (12)
C14—O1—Na1	122.87 (14)	C25—O6—Na1	120.14 (14)
O1—C15—C16	107.65 (18)	O6—C25—H25A	109.5
O1—C15—H15A	110.2	O6—C25—H25B	109.5
C16—C15—H15A	110.2	H25A—C25—H25B	109.5
O1—C15—H15B	110.2	O6—C25—H25C	109.5
C16—C15—H15B	110.2	H25A—C25—H25C	109.5
H15A—C15—H15B	108.5	H25B—C25—H25C	109.5
O2—C16—C15	107.43 (17)
C8—C1—C2—C3	−161.55 (16)	C14—O1—C15—C16	−175.81 (19)
C1i—C1—C2—C3	17.1 (2)	Na1—O1—C15—C16	−28.6 (2)
C8—C1—C2—C7	21.4 (3)	O1—C15—C16—O2	59.8 (2)
C1i—C1—C2—C7	−159.90 (15)	O1—C15—C16—Na1	19.41 (14)
C7—C2—C3—C4	−2.6 (2)	C15—C16—O2—C17	177.87 (18)
C1—C2—C3—C4	−179.96 (17)	Na1—C16—O2—C17	−121.37 (18)
C2—C3—C4—C5	1.8 (3)	C15—C16—O2—Na1	−60.75 (18)
C3—C4—C5—C6	0.6 (3)	C16—O2—C17—C18	169.02 (18)
C4—C5—C6—C7	−2.1 (3)	Na1—O2—C17—C18	49.6 (2)
C5—C6—C7—C2	1.3 (3)	O2—C17—C18—O3	−64.0 (3)
C3—C2—C7—C6	1.1 (2)	C17—C18—O3—C19	−175.3 (2)
C1—C2—C7—C6	178.24 (17)	C17—C18—O3—Na1	44.6 (2)
C2—C1—C8—C9	−167.86 (16)	C20—O4—C21—C22	−108.3 (3)
C1i—C1—C8—C9	13.5 (2)	Na1—O4—C21—C22	48.4 (3)
C2—C1—C8—C13	15.4 (3)	O4—C21—C22—O5	−57.4 (3)
C1i—C1—C8—C13	−163.26 (15)	C21—C22—O5—C23	162.93 (18)
C1—C8—C9—C10	−179.18 (17)	C21—C22—O5—Na1	37.7 (2)
C13—C8—C9—C10	−2.1 (2)	C22—O5—C23—C24	178.34 (17)
C8—C9—C10—C11	0.7 (3)	Na1—O5—C23—C24	−53.51 (18)
C9—C10—C11—C12	1.1 (3)	C22—O5—C23—Na1	−128.15 (18)
C10—C11—C12—C13	−1.4 (3)	O5—C23—C24—O6	61.5 (2)
C11—C12—C13—C8	−0.1 (3)	Na1—C23—C24—O6	26.01 (14)
C1—C8—C13—C12	178.66 (17)	C23—C24—O6—C25	−175.77 (18)
C9—C8—C13—C12	1.8 (2)	C23—C24—O6—Na1	−37.7 (2)

Table 1

Selected bond lengths (Å)

C1—C1i	1.507 (3)
C1—C2	1.438 (2)
C1—C8	1.429 (2)
C2—C3	1.424 (3)
C2—C7	1.434 (3)
C3—C4	1.384 (3)
C4—C5	1.390 (3)
C5—C6	1.390 (3)
C6—C7	1.387 (3)
C8—C9	1.433 (3)
C8—C13	1.436 (3)
C9—C10	1.380 (3)
C10—C11	1.389 (3)
C11—C12	1.394 (3)
C12—C13	1.378 (3)

Symmetry code: (i) .