A threefold superstructure of the anti-epileptic drug phenytoin sodium as a mixed methanol solvate hydrate

Phenytoin sodium, a salt of 5,5-di­phenyl­imidazolidine-2,4-dione, or phenytoin, is commercially available in various dosage forms for its anti-­epileptic properties to treat and prevent seizures. The title compound, poly[aqua­tris­(μ₃-4,4-diphenyl-2,5-dioxoimidazolidin-1-ido)tri­methano­ltrisodium(I)], [Na₃(C₁₅H₁₁N₂O₂)₃(CH₄O)₃(H₂O)_1.08]_n, a methanol solvate and hydrate of phenytoin sodium, forms a modulated crystal structure that consists of a supercell made up of three close-to-identical repeat units. Each of the basic fragments consists of one phenytoin anion, a sodium cation, and either a methanol, or a methanol and a water mol­ecule coordinated to the sodium ion, yielding a formula unit of Na(C₁₅H₁₁N₂O₂)(CH₃OH)_x(H₂O)_y for each of the three segments (x, y = 0 or 1; x + y = 1 or 2). Modulation along the b axis is introduced due to the presence or absence of water or methanol mol­ecules at sodium and by the alternating torsion angles of one of the two phenytoin phenyl rings. Individual segments within the asymmetric unit are linked by covalent Na—O and Na—N bonds, with each sodium ion coordinated to one anionic amide N atom and three keto O atoms. The Na—N and one of the Na—O bonds connect (C₁₅H₁₁N₂O₂)·Na units along the modulation direction, creating an infinite [(C₁₅H₁₁N₂O₂)·Na] chain that is further stabilized by intra­molecular N—H...O hydrogen bonding parallel to [010]. The second Na—O bond connects this chain with a symmetry-equivalent copy of itself created by a screw-axis operation, yielding double strands of [(C₁₅H₁₁N₂O₂)·Na] chains. Two of these double strands, propagating in opposite directions, constitute the content of the unit cell. Neighboring double strands are connected with each other to form layers perpendicular to the a axis, tethered together via O—H...O hydrogen bonds involving the water and methanol mol­ecules. In addition to modulation, each of the repeat units also exhibits disorder of the modulated segments. Phenyl rings of each repeat unit are rotationally disordered, and sodium-coordinated methanol and water mol­ecules are also positionally disordered and/or partially occupied. The solvated structure reported here, while not matching the patterns reported for any of the known forms of phenytoin sodium, does provide a first insight into the complications and complexities involved in resolving the structure of anhydrous phenytoin sodium.

Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015, 2018) and SHELXLE (Hübschle et al., 2011).

Poly[aquatris(µ₃-4,4-diphenyl-2,5-dioxoimidazolidin-1-ido)trimethanoltrisodium(I)]

Crystal data

[Na3(C15H11N2O2)3(CH4O)3(H2O)1.08]	F(000) = 1963
Mr = 938.33	Dx = 1.372 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 15.9687 (3) Å	Cell parameters from 9888 reflections
b = 18.7065 (4) Å	θ = 2.9–80.1°
c = 15.8249 (4) Å	µ = 1.05 mm^−1
β = 106.0770 (12)°	T = 150 K
V = 4542.31 (17) Å^3	Rod, colourless
Z = 4	0.21 × 0.15 × 0.13 mm

Data collection

Bruker D8 Quest CMOS diffractometer	9389 independent reflections
Radiation source: sealed tube X-ray source	7343 reflections with I > 2σ(I)
Triumph curved graphite crystal monochromator	Rint = 0.048
ω and phi scans	θmax = 80.4°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −18→20
Tmin = 0.653, Tmax = 0.754	k = −21→23
30401 measured reflections	l = −19→20

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)] = 0.051	Hydrogen site location: mixed
wR(F^2) = 0.158	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0899P)^2 + 1.3413P] where P = (Fo^2 + 2Fc^2)/3
9389 reflections	(Δ/σ)max = 0.003
892 parameters	Δρmax = 0.59 e Å^−3
856 restraints	Δρmin = −0.43 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The compound crystallizes as a three-fold superstructure with modulation along the b-axis of the unit cell. Modulation is induced by the presence or absence of a water molecule coordinated to sodium opposite of coordinated methanol. In the major disordered moiety, water is present for one of the three sodium ions (Na1B), but not the other two (Na1A, Na1C). The presence or absence of the water molecule induces modulation for the neighboring methanol molecules and for one of the two phenyl rings of each phenytoin anion. Disorder is observed due to occasional presence of water molecules at Na1A and Na1C, causing equal occupancy disorder for the methanol molecules and phenyl rings. The major methanol molecules at Na1B are in addition disordered over two moieties.

Chemically equivalent disordered moieties were restrained to have similar geometries. ADPs of overlapping Na ions were constrained to be identical. ADPS of overlapping ipso carbon atoms of disordered phenyl rings were also were constrained to be identical. Uij components of ADPs for disordered atoms closer to each other than 2.0 Angstrom were restrained to be similar. Occupancies were set to match the major occupancy ratio (for absence or presence of water at Na1B). Independent refinement of occupancies yielded occupancy rates within one percent of the constrained identical values. Atom C4F was restrained to lie within a plane formed by its three direct neighbors. Subject to these conditions the occupancy ratio refined to 0.9195 (12) to 0.0805 (12). The additional methanol disorder rates refined to 0.525 (3) (for O3B and C16B) and 0.395 (3) (for O3E and C16E).

Water and methanol H atom positions were initially refined. O-H and H···H distances were restrained to 0.84 (2) and 1.36 (2) Angstrom, respectively, and H···C distances to 1.90 (2) Angstrom, while a mild damping factor was applied. Water H atom H4D was further restrained to have a minimum distance of 2.60 (2) Angstrom from sodium atom Na1D. Amine H atom positions were refined and N-H distances restrained to 0.88 (2) Angstroms. H atoms attached to carbon atoms were positioned geometrically and constrained to ride on their parent atoms, with carbon hydrogen bond distances of 0.95 Angstrom for and aromatic C-H and 0.98 Angstrom for aliphatic CH3 moieties, respectively. Methyl H atoms were allowed to rotate but not to tip to best fit the experimental electron density. Uiso(H) values were set to a multiple of Ueq(C) with 1.5 for CH3 and OH, and 1.2 for C-H and N-H units, respectively.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1A	−0.22185 (10)	0.84730 (7)	0.31194 (9)	0.0293 (3)
O2A	−0.08620 (9)	1.04258 (7)	0.24194 (9)	0.0282 (3)
Na1A	−0.04353 (6)	0.83195 (5)	0.29569 (6)	0.0234 (2)	0.9195 (12)
O3A	0.03758 (12)	0.85895 (10)	0.44144 (11)	0.0381 (4)	0.9195 (12)
H3A	0.0200 (19)	0.8683 (16)	0.4872 (16)	0.057*	0.9195 (12)
C16A	0.1041 (2)	0.80614 (16)	0.46492 (18)	0.0490 (7)	0.9195 (12)
H16A	0.078148	0.759918	0.472327	0.073*	0.9195 (12)
H16B	0.146498	0.819775	0.520204	0.073*	0.9195 (12)
H16C	0.133592	0.802346	0.418385	0.073*	0.9195 (12)
Na1D	−0.0480 (8)	0.8281 (7)	0.2639 (7)	0.0234 (2)	0.0805 (12)
O3D	0.0159 (18)	0.8058 (13)	0.4238 (12)	0.059 (4)	0.0805 (12)
H3D	−0.01 (2)	0.801 (12)	0.463 (18)	0.089*	0.0805 (12)
C16D	0.074 (2)	0.7492 (18)	0.4240 (19)	0.066 (5)	0.0805 (12)
H16J	0.041540	0.703992	0.414210	0.100*	0.0805 (12)
H16K	0.118176	0.747608	0.480868	0.100*	0.0805 (12)
H16L	0.102024	0.756551	0.377008	0.100*	0.0805 (12)
O4D	−0.0850 (18)	0.8221 (12)	0.1002 (11)	0.055 (6)	0.0805 (12)
H4C	−0.059179	0.800237	0.068339	0.083*	0.0805 (12)
H4D	−0.135695	0.810372	0.100506	0.083*	0.0805 (12)
N1A	−0.13639 (10)	0.93176 (8)	0.27151 (10)	0.0230 (3)
N2A	−0.21442 (10)	1.03116 (7)	0.27918 (10)	0.0208 (3)
H2A	−0.2206 (16)	1.0769 (9)	0.2873 (14)	0.025*
C1A	−0.20602 (11)	0.91003 (9)	0.29605 (11)	0.0196 (3)
C2A	−0.14166 (11)	1.00456 (9)	0.26287 (11)	0.0207 (3)
C3A	−0.26596 (11)	0.97456 (8)	0.30203 (11)	0.0179 (3)
C4A	−0.2786 (3)	0.9823 (2)	0.39449 (19)	0.0195 (4)	0.9195 (12)
C5A	−0.27495 (13)	1.04987 (10)	0.43294 (12)	0.0229 (4)	0.9195 (12)
H5A	−0.261869	1.090600	0.403056	0.027*	0.9195 (12)
C6A	−0.29039 (15)	1.05787 (11)	0.51511 (13)	0.0291 (4)	.9195 (12)
H6A	−0.287564	1.103961	0.540952	0.035*	0.9195 (12)
C7A	−0.30977 (17)	0.99889 (13)	0.55900 (14)	0.0301 (5)	.9195 (12)
H7A	−0.319212	1.004226	0.615354	0.036*	0.9195 (12)
C8A	−0.3153 (3)	0.93268 (14)	0.5206 (2)	0.0338 (7)	0.9195 (12)
H8A	−0.329883	0.892240	0.550001	0.041*	0.9195 (12)
C9A	−0.29953 (19)	0.92436 (13)	0.43864 (17)	0.0311 (6)	0.9195 (12)
H9A	−0.303268	0.878158	0.412933	0.037*	0.9195 (12)
C4D	−0.271 (4)	0.992 (3)	0.396 (2)	0.0195 (4)	0.0805 (12)
C5D	−0.2138 (17)	1.0396 (12)	0.4525 (12)	0.029 (3)	0.0805 (12)
H5D	−0.174446	1.067782	0.431232	0.035*	0.0805 (12)
C6D	−0.2150 (17)	1.0451 (13)	0.5404 (13)	0.037 (3)	0.0805 (12)
H6D	−0.180221	1.080512	0.576858	0.044*	0.0805 (12)
C7D	−0.266 (2)	0.9999 (14)	0.5757 (16)	0.034 (3)	0.0805 (12)
H7D	−0.265542	1.003700	0.635732	0.041*	0.0805 (12)
C8D	−0.316 (3)	0.950 (2)	0.522 (2)	0.028 (3)	0.0805 (12)
H8D	−0.353332	0.919887	0.544095	0.034*	0.0805 (12)
C9D	−0.314 (2)	0.9438 (16)	0.4339 (19)	0.029 (3)	0.0805 (12)
H9D	−0.343208	0.904726	0.399728	0.034*	0.0805 (12)
C10A	−0.35586 (11)	0.96743 (9)	0.23469 (11)	0.0208 (3)
C11A	−0.39119 (14)	1.02382 (11)	0.17866 (12)	0.0302 (4)
H11A	−0.359040	1.066888	0.181342	0.036*
C12A	−0.47350 (15)	1.01765 (14)	0.11851 (14)	0.0397 (5)
H12A	−0.496883	1.056455	0.080589	0.048*
C13A	−0.52092 (14)	0.95543 (15)	0.11400 (14)	0.0412 (5)
H13A	−0.576675	0.951192	0.072806	0.049*
C14A	−0.48688 (14)	0.89924 (13)	0.16976 (14)	0.0369 (5)
H14A	−0.519466	0.856405	0.167078	0.044*
C15A	−0.40482 (13)	0.90532 (11)	0.22991 (12)	0.0284 (4)
H15A	−0.382075	0.866532	0.268125	0.034*
C1B	−0.19529 (12)	0.57597 (9)	0.29081 (11)	0.0215 (3)
O1B	−0.21687 (10)	0.51230 (7)	0.28965 (10)	0.0331 (3)
O2B	−0.06212 (9)	0.71289 (8)	0.27546 (11)	0.0348 (3)
Na1B	−0.0401 (17)	0.4894 (14)	0.2734 (8)	0.0312 (7)	0.525 (3)
O3B	0.0467 (3)	0.4570 (2)	0.4253 (3)	0.0617 (10)	0.525 (3)
H3B	0.034 (7)	0.4856 (12)	0.461 (4)	0.093*	0.525 (3)
C16B	0.0343 (8)	0.3829 (4)	0.4577 (7)	0.073 (2)	0.525 (3)
H16D	−0.025028	0.366386	0.429069	0.109*	0.525 (3)
H16E	0.043582	0.383999	0.521506	0.109*	0.525 (3)
H16F	0.076348	0.350151	0.443390	0.109*	0.525 (3)
O4B	−0.08921 (12)	0.49394 (9)	0.10696 (12)	0.0394 (4)	0.9195 (12)
H4A	−0.0716 (19)	0.4679 (17)	0.0707 (19)	0.059*	0.9195 (12)
H4B	−0.1448 (11)	0.4934 (18)	0.089 (2)	0.059*	0.9195 (12)
Na1E	−0.046 (2)	0.4911 (18)	0.2685 (10)	0.0312 (7)	0.395 (3)
O3E	−0.0147 (3)	0.4634 (3)	0.4291 (3)	0.0479 (11)	0.395 (3)
H3E	0.016 (3)	0.5017 (14)	0.439 (7)	0.072*	0.395 (3)
C16E	0.0422 (11)	0.4048 (6)	0.4694 (9)	0.074 (3)	0.395 (3)
H16M	0.066077	0.382094	0.425331	0.112*	0.395 (3)
H16N	0.008831	0.369537	0.492552	0.112*	0.395 (3)
H16O	0.089963	0.423259	0.517578	0.112*	0.395 (3)
Na1F	−0.045 (2)	0.5005 (17)	0.2798 (17)	0.0312 (7)	0.0806 (12)
O3F	0.0348 (16)	0.5135 (14)	0.4385 (17)	0.058 (4)	0.0806 (12)
H3F	0.011541	0.504884	0.479160	0.087*	0.0806 (12)
C16F	0.1202 (18)	0.478 (2)	0.462 (2)	0.067 (4)	0.0806 (12)
H16P	0.117018	0.434761	0.426030	0.101*	0.0806 (12)
H16Q	0.136630	0.465151	0.524110	0.101*	0.0806 (12)
H16R	0.163920	0.510593	0.450242	0.101*	0.0806 (12)
N1B	−0.12039 (10)	0.59983 (8)	0.27872 (11)	0.0254 (3)
N2B	−0.19749 (10)	0.69736 (7)	0.29575 (10)	0.0213 (3)
H2B	−0.2054 (16)	0.7432 (9)	0.3033 (14)	0.026*
C2B	−0.12222 (12)	0.67301 (10)	0.28295 (12)	0.0236 (4)
C3B	−0.25291 (11)	0.63895 (8)	0.30648 (10)	0.0173 (3)
C4B	−0.2652 (4)	0.6370 (2)	0.3995 (2)	0.0208 (5)	0.9195 (12)
C5B	−0.27158 (16)	0.70137 (12)	0.44051 (14)	0.0287 (4)	0.9195 (12)
H5B	−0.267131	0.745064	0.411474	0.034*	0.9195 (12)
C6B	−0.28446 (17)	0.70251 (13)	0.52387 (14)	0.0363 (5)	0.9195 (12)
H6B	−0.288208	0.746935	0.551673	0.044*	0.9195 (12)
C7B	−0.29184 (19)	0.63937 (16)	0.56642 (16)	0.0367 (6)	0.9195 (12)
H7B	−0.300985	0.640226	0.623231	0.044*	0.9195 (12)
C8B	−0.2858 (2)	0.57517 (16)	0.52595 (16)	0.0413 (6)	0.9195 (12)
H8B	−0.290725	0.531614	0.555101	0.050*	0.9195 (12)
C9B	−0.27266 (17)	0.57365 (12)	0.44242 (14)	0.0328 (5)	0.9195 (12)
H9B	−0.268793	0.529119	0.414874	0.039*	0.9195 (12)
C4E	−0.262 (5)	0.648 (3)	0.401 (2)	0.0208 (5)	0.0805 (12)
C5E	−0.220 (2)	0.7043 (13)	0.4532 (13)	0.033 (3)	0.0805 (12)
H5E	−0.190917	0.739952	0.428736	0.040*	0.0805 (12)
C6E	−0.2186 (19)	0.7083 (13)	0.5423 (14)	0.040 (3)	0.0805 (12)
H6E	−0.184146	0.743077	0.580232	0.048*	0.0805 (12)
C7E	−0.269 (2)	0.6604 (17)	0.5730 (17)	0.036 (3)	0.0805 (12)
H7E	−0.270411	0.664095	0.632437	0.043*	0.0805 (12)
C8E	−0.3167 (19)	0.6075 (16)	0.5215 (14)	0.031 (2)	0.0805 (12)
H8E	−0.347588	0.573079	0.545298	0.038*	0.0805 (12)
C9E	−0.3184 (17)	0.6062 (13)	0.4317 (13)	0.030 (2)	0.0805 (12)
H9E	−0.358522	0.575824	0.392218	0.036*	0.0805 (12)
C10B	−0.34214 (11)	0.63911 (9)	0.23828 (11)	0.0194 (3)
C11B	−0.37004 (13)	0.69898 (10)	0.18562 (12)	0.0251 (4)
H11B	−0.333672	0.739963	0.192108	0.030*
C12B	−0.45139 (14)	0.69881 (12)	0.12333 (13)	0.0325 (4)
H12B	−0.470116	0.739660	0.087392	0.039*
C13B	−0.50464 (13)	0.63964 (13)	0.11377 (13)	0.0350 (5)
H13B	−0.559308	0.639290	0.070313	0.042*
C14B	−0.47841 (13)	0.58073 (12)	0.16753 (14)	0.0329 (4)
H14B	−0.515736	0.540419	0.161908	0.040*
C15B	−0.39747 (12)	0.58048 (10)	0.22979 (12)	0.0259 (4)
H15B	−0.379879	0.540021	0.266733	0.031*
O1C	−0.22169 (9)	0.17992 (7)	0.31179 (9)	0.0265 (3)
O2C	−0.07230 (9)	0.37029 (7)	0.25019 (9)	0.0287 (3)
Na1C	−0.04591 (14)	0.15758 (9)	0.27014 (11)	0.0251 (3)	0.9195 (12)
O3C	0.03227 (12)	0.12920 (10)	0.41849 (11)	0.0387 (4)	0.9195 (12)
H3C	0.0498 (18)	0.0838 (8)	0.418 (2)	0.058*	0.9195 (12)
C16C	0.1057 (2)	0.1734 (3)	0.4470 (3)	0.0624 (9)	0.9195 (12)
H16G	0.146201	0.163794	0.411798	0.094*	0.9195 (12)
H16H	0.134689	0.163645	0.509090	0.094*	0.9195 (12)
H16I	0.087556	0.223592	0.440092	0.094*	0.9195 (12)
Na1G	−0.0467 (19)	0.1684 (14)	0.2817 (15)	0.0251 (3)	0.0805 (12)
O3G	0.0328 (15)	0.1823 (14)	0.4319 (13)	0.053 (3)	0.0805 (12)
H3G	0.021732	0.144233	0.454796	0.079*	0.0805 (12)
C16G	0.1221 (18)	0.187 (3)	0.433 (3)	0.056 (4)	0.0805 (12)
H16S	0.126672	0.207565	0.377749	0.084*	0.0805 (12)
H16T	0.147507	0.138429	0.439603	0.084*	0.0805 (12)
H16U	0.153683	0.216438	0.482409	0.084*	0.0805 (12)
O4G	−0.084 (2)	0.1525 (15)	0.096 (2)	0.073 (8)	0.0805 (12)
H4E	−0.138193	0.157072	0.079289	0.110*	0.0805 (12)
H4F	−0.059860	0.116547	0.080201	0.110*	0.0805 (12)
N1C	−0.12862 (10)	0.26102 (8)	0.27679 (10)	0.0228 (3)
N2C	−0.20533 (10)	0.36235 (8)	0.27755 (10)	0.0217 (3)
H2C	−0.2108 (16)	0.4086 (9)	0.2834 (15)	0.026*
C1C	−0.20148 (11)	0.24179 (9)	0.29722 (10)	0.0182 (3)
C2C	−0.13106 (11)	0.33393 (9)	0.26684 (11)	0.0208 (3)
C3C	−0.25863 (11)	0.30822 (8)	0.30218 (10)	0.0171 (3)
C4C	−0.26416 (17)	0.31824 (14)	0.39694 (14)	0.0198 (4)	0.9195 (12)
C5C	−0.21286 (17)	0.36924 (12)	0.45144 (14)	0.0315 (5)	0.9195 (12)
H5C	−0.176043	0.399539	0.429368	0.038*	0.9195 (12)
C6C	−0.21540 (19)	0.37595 (13)	0.53857 (15)	0.0397 (5)	0.9195 (12)
H6C	−0.180142	0.410877	0.575458	0.048*	0.9195 (12)
C7C	−0.26855 (18)	0.33244 (15)	0.57173 (15)	0.0346 (6)	0.9195 (12)
H7C	−0.269216	0.336850	0.631348	0.041*	0.9195 (12)
C8C	−0.32084 (16)	0.28236 (15)	0.51754 (15)	0.0316 (5)	0.9195 (12)
H8C	−0.358507	0.252892	0.539528	0.038*	0.9195 (12)
C9C	−0.31819 (15)	0.27515 (13)	0.43040 (13)	0.0249 (4)	0.9195 (12)
H9C	−0.353798	0.240355	0.393625	0.030*	0.9195 (12)
C4F	−0.2706 (16)	0.3131 (13)	0.3957 (11)	0.0198 (4)	0.0805 (12)
C5F	−0.266 (2)	0.3778 (11)	0.4380 (14)	0.030 (3)	0.0805 (12)
H5F	−0.248469	0.418954	0.411969	0.035*	0.0805 (12)
C6F	−0.286 (2)	0.3851 (12)	0.5188 (14)	0.037 (2)	0.0805 (12)
H6F	−0.291133	0.430950	0.542563	0.044*	0.0805 (12)
C7F	−0.298 (3)	0.3243 (13)	0.5622 (18)	0.035 (3)	0.0805 (12)
H7F	−0.304381	0.327677	0.619943	0.042*	0.0805 (12)
C8F	−0.300 (2)	0.2589 (13)	0.5234 (16)	0.032 (3)	0.0805 (12)
H8F	−0.311016	0.217233	0.553094	0.038*	0.0805 (12)
C9F	−0.287 (2)	0.2532 (13)	0.4399 (15)	0.028 (3)	0.0805 (12)
H9F	−0.290178	0.207570	0.413035	0.034*	0.0805 (12)
C10C	−0.34880 (11)	0.30258 (9)	0.23559 (11)	0.0190 (3)
C11C	−0.38427 (13)	0.36272 (11)	0.18654 (12)	0.0269 (4)
H11C	−0.352440	0.406282	0.195110	0.032*
C12C	−0.46558 (14)	0.35972 (12)	0.12530 (13)	0.0340 (4)
H12C	−0.488474	0.400909	0.091697	0.041*
C13C	−0.51320 (14)	0.29717 (13)	0.11312 (13)	0.0355 (5)
H13C	−0.568715	0.295226	0.071129	0.043*
C14C	−0.47987 (13)	0.23735 (12)	0.16218 (13)	0.0328 (4)
H14C	−0.512889	0.194409	0.154453	0.039*
C15C	−0.39782 (12)	0.23987 (10)	0.22307 (12)	0.0253 (4)
H15C	−0.375169	0.198444	0.256289	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0400 (8)	0.0135 (6)	0.0370 (7)	0.0012 (5)	0.0153 (6)	0.0012 (5)
O2A	0.0244 (6)	0.0250 (6)	0.0413 (7)	−0.0025 (5)	0.0191 (6)	−0.0007 (5)
Na1A	0.0219 (4)	0.0189 (4)	0.0318 (5)	0.0018 (3)	0.0115 (4)	0.0016 (4)
O3A	0.0419 (9)	0.0405 (9)	0.0322 (8)	0.0094 (8)	0.0108 (7)	0.0026 (7)
C16A	0.0489 (15)	0.0499 (15)	0.0402 (13)	0.0178 (12)	−0.0008 (11)	0.0011 (11)
Na1D	0.0219 (4)	0.0189 (4)	0.0318 (5)	0.0018 (3)	0.0115 (4)	0.0016 (4)
O3D	0.063 (6)	0.051 (6)	0.054 (6)	0.004 (6)	−0.001 (6)	−0.003 (6)
C16D	0.067 (8)	0.060 (8)	0.060 (7)	0.010 (7)	−0.003 (7)	0.002 (7)
O4D	0.071 (16)	0.046 (12)	0.039 (11)	−0.007 (12)	−0.002 (10)	0.005 (9)
N1A	0.0217 (7)	0.0178 (7)	0.0308 (7)	0.0035 (6)	0.0094 (6)	−0.0018 (6)
N2A	0.0243 (7)	0.0109 (6)	0.0337 (8)	0.0005 (5)	0.0188 (6)	0.0009 (5)
C1A	0.0241 (8)	0.0141 (7)	0.0211 (7)	0.0034 (6)	0.0069 (6)	−0.0006 (6)
C2A	0.0209 (8)	0.0195 (8)	0.0236 (8)	0.0002 (6)	0.0094 (6)	−0.0005 (6)
C3A	0.0229 (8)	0.0118 (7)	0.0222 (7)	0.0000 (6)	0.0116 (6)	0.0006 (6)
C4A	0.0219 (13)	0.0176 (16)	0.0215 (8)	−0.0021 (8)	0.0100 (7)	−0.0018 (7)
C5A	0.0273 (10)	0.0198 (9)	0.0237 (9)	0.0018 (7)	0.0106 (7)	−0.0001 (7)
C6A	0.0368 (11)	0.0258 (10)	0.0263 (9)	0.0034 (8)	0.0115 (8)	−0.0050 (7)
C7A	0.0334 (11)	0.0368 (12)	0.0237 (10)	−0.0013 (10)	0.0138 (9)	−0.0012 (8)
C8A	0.0473 (13)	0.0320 (16)	0.0278 (10)	−0.0102 (15)	0.0199 (9)	0.0004 (10)
C9A	0.0474 (15)	0.0236 (12)	0.0270 (10)	−0.0102 (11)	0.0181 (10)	−0.0020 (9)
C4D	0.0219 (13)	0.0176 (16)	0.0215 (8)	−0.0021 (8)	0.0100 (7)	−0.0018 (7)
C5D	0.036 (4)	0.025 (4)	0.027 (4)	−0.001 (4)	0.009 (4)	−0.002 (4)
C6D	0.042 (5)	0.034 (5)	0.035 (5)	0.000 (4)	0.011 (4)	−0.004 (4)
C7D	0.042 (5)	0.034 (5)	0.029 (5)	0.000 (5)	0.013 (5)	−0.004 (4)
C8D	0.037 (5)	0.030 (5)	0.026 (5)	−0.003 (5)	0.022 (4)	0.001 (5)
C9D	0.035 (5)	0.025 (5)	0.028 (5)	−0.003 (5)	0.012 (4)	−0.006 (5)
C10A	0.0227 (8)	0.0227 (8)	0.0210 (7)	0.0025 (7)	0.0124 (6)	−0.0013 (6)
C11A	0.0354 (10)	0.0304 (10)	0.0253 (9)	0.0076 (8)	0.0092 (8)	0.0047 (7)
C12A	0.0380 (11)	0.0520 (13)	0.0271 (10)	0.0157 (10)	0.0057 (8)	0.0030 (9)
C13A	0.0277 (10)	0.0649 (15)	0.0294 (10)	0.0067 (10)	0.0053 (8)	−0.0103 (10)
C14A	0.0277 (10)	0.0508 (13)	0.0350 (10)	−0.0092 (9)	0.0132 (8)	−0.0106 (9)
C15A	0.0271 (9)	0.0316 (10)	0.0289 (9)	−0.0037 (8)	0.0116 (7)	−0.0011 (7)
C1B	0.0261 (8)	0.0144 (8)	0.0247 (8)	0.0037 (7)	0.0084 (7)	0.0006 (6)
O1B	0.0379 (8)	0.0134 (6)	0.0492 (8)	0.0012 (5)	0.0142 (6)	−0.0003 (5)
O2B	0.0283 (7)	0.0255 (7)	0.0608 (9)	−0.0020 (6)	0.0294 (7)	−0.0018 (6)
Na1B	0.028 (2)	0.0160 (13)	0.0567 (11)	0.0002 (14)	0.0237 (12)	−0.0033 (10)
O3B	0.059 (2)	0.066 (2)	0.056 (2)	0.005 (2)	0.0095 (18)	−0.0101 (18)
C16B	0.061 (4)	0.061 (4)	0.072 (4)	0.001 (3)	−0.020 (3)	−0.012 (3)
O4B	0.0317 (8)	0.0340 (9)	0.0496 (10)	−0.0035 (7)	0.0064 (7)	−0.0032 (7)
Na1E	0.028 (2)	0.0160 (13)	0.0567 (11)	0.0002 (14)	0.0237 (12)	−0.0033 (10)
O3E	0.045 (2)	0.054 (2)	0.042 (2)	0.008 (2)	0.0067 (18)	−0.0032 (19)
C16E	0.070 (4)	0.081 (5)	0.055 (4)	0.010 (5)	−0.010 (4)	0.001 (4)
Na1F	0.028 (2)	0.0160 (13)	0.0567 (11)	0.0002 (14)	0.0237 (12)	−0.0033 (10)
O3F	0.058 (6)	0.059 (6)	0.046 (6)	0.002 (6)	−0.005 (6)	−0.013 (6)
C16F	0.065 (6)	0.071 (7)	0.057 (6)	0.003 (6)	0.001 (6)	−0.007 (6)
N1B	0.0258 (7)	0.0179 (7)	0.0361 (8)	0.0041 (6)	0.0145 (6)	−0.0031 (6)
N2B	0.0218 (7)	0.0119 (7)	0.0361 (8)	−0.0007 (5)	0.0179 (6)	−0.0013 (5)
C2B	0.0224 (8)	0.0214 (8)	0.0316 (9)	0.0011 (7)	0.0153 (7)	−0.0024 (7)
C3B	0.0224 (8)	0.0114 (7)	0.0216 (7)	−0.0021 (6)	0.0116 (6)	−0.0005 (5)
C4B	0.0185 (8)	0.0245 (18)	0.0216 (8)	−0.0023 (12)	0.0094 (7)	0.0005 (8)
C5B	0.0373 (12)	0.0265 (10)	0.0266 (10)	0.0048 (9)	0.0160 (9)	−0.0004 (7)
C6B	0.0468 (13)	0.0405 (12)	0.0270 (10)	0.0062 (10)	0.0192 (9)	−0.0020 (9)
C7B	0.0406 (15)	0.0495 (17)	0.0247 (10)	−0.0006 (11)	0.0169 (10)	0.0033 (10)
C8B	0.0557 (15)	0.0401 (13)	0.0333 (12)	−0.0064 (12)	0.0211 (11)	0.0097 (10)
C9B	0.0473 (13)	0.0256 (10)	0.0292 (10)	−0.0070 (10)	0.0167 (9)	0.0018 (8)
C4E	0.0185 (8)	0.0245 (18)	0.0216 (8)	−0.0023 (12)	0.0094 (7)	0.0005 (8)
C5E	0.039 (5)	0.033 (5)	0.028 (4)	0.002 (5)	0.010 (4)	−0.002 (4)
C6E	0.048 (5)	0.038 (5)	0.034 (5)	0.002 (5)	0.014 (4)	−0.001 (4)
C7E	0.046 (5)	0.040 (5)	0.028 (5)	0.000 (5)	0.021 (4)	0.002 (5)
C8E	0.042 (4)	0.036 (4)	0.026 (4)	−0.004 (4)	0.024 (4)	0.006 (4)
C9E	0.038 (4)	0.029 (4)	0.027 (4)	−0.005 (4)	0.013 (4)	0.001 (4)
C10B	0.0213 (8)	0.0200 (8)	0.0203 (7)	0.0006 (6)	0.0114 (6)	−0.0015 (6)
C11B	0.0292 (9)	0.0243 (9)	0.0241 (8)	0.0031 (7)	0.0112 (7)	0.0016 (6)
C12B	0.0319 (10)	0.0398 (11)	0.0253 (9)	0.0116 (9)	0.0073 (8)	0.0023 (8)
C13B	0.0239 (9)	0.0512 (13)	0.0288 (9)	0.0064 (9)	0.0057 (7)	−0.0083 (9)
C14B	0.0248 (9)	0.0391 (11)	0.0369 (10)	−0.0061 (8)	0.0118 (8)	−0.0093 (8)
C15B	0.0244 (8)	0.0248 (9)	0.0306 (9)	−0.0030 (7)	0.0110 (7)	−0.0007 (7)
O1C	0.0356 (7)	0.0139 (6)	0.0314 (7)	0.0003 (5)	0.0116 (6)	0.0017 (5)
O2C	0.0241 (6)	0.0268 (7)	0.0413 (7)	−0.0055 (5)	0.0194 (6)	−0.0012 (5)
Na1C	0.0232 (4)	0.0160 (8)	0.0406 (7)	0.0018 (5)	0.0165 (5)	0.0005 (4)
O3C	0.0411 (9)	0.0363 (9)	0.0386 (9)	0.0056 (7)	0.0109 (7)	−0.0016 (7)
C16C	0.0515 (19)	0.076 (3)	0.0538 (19)	−0.0146 (17)	0.0053 (15)	−0.0018 (16)
Na1G	0.0232 (4)	0.0160 (8)	0.0406 (7)	0.0018 (5)	0.0165 (5)	0.0005 (4)
O3G	0.047 (6)	0.054 (6)	0.052 (6)	−0.005 (6)	0.006 (5)	−0.001 (5)
C16G	0.051 (6)	0.057 (6)	0.053 (6)	−0.005 (6)	0.005 (6)	−0.004 (6)
O4G	0.075 (19)	0.052 (15)	0.079 (19)	−0.006 (14)	0.000 (15)	−0.002 (13)
N1C	0.0213 (7)	0.0192 (7)	0.0304 (7)	0.0018 (6)	0.0112 (6)	−0.0021 (6)
N2C	0.0220 (7)	0.0120 (7)	0.0364 (8)	−0.0013 (5)	0.0168 (6)	0.0019 (5)
C1C	0.0217 (8)	0.0136 (7)	0.0197 (7)	0.0025 (6)	0.0064 (6)	−0.0001 (6)
C2C	0.0208 (8)	0.0193 (8)	0.0245 (8)	−0.0006 (6)	0.0101 (6)	−0.0012 (6)
C3C	0.0214 (8)	0.0113 (7)	0.0218 (7)	−0.0003 (6)	0.0114 (6)	0.0019 (5)
C4C	0.0201 (8)	0.0194 (8)	0.0213 (7)	0.0016 (7)	0.0080 (6)	−0.0017 (6)
C5C	0.0368 (12)	0.0285 (10)	0.0284 (10)	−0.0089 (9)	0.0078 (9)	−0.0043 (8)
C6C	0.0543 (14)	0.0349 (12)	0.0278 (10)	−0.0055 (11)	0.0077 (10)	−0.0093 (9)
C7C	0.0440 (15)	0.0375 (12)	0.0224 (10)	0.0112 (11)	0.0095 (10)	−0.0013 (9)
C8C	0.0339 (12)	0.0390 (13)	0.0269 (10)	0.0056 (10)	0.0168 (9)	0.0035 (9)
C9C	0.0242 (9)	0.0290 (10)	0.0240 (9)	−0.0010 (8)	0.0105 (8)	−0.0006 (8)
C4F	0.0201 (8)	0.0194 (8)	0.0213 (7)	0.0016 (7)	0.0080 (6)	−0.0017 (6)
C5F	0.039 (4)	0.027 (4)	0.024 (4)	0.000 (4)	0.011 (4)	−0.002 (4)
C6F	0.046 (4)	0.037 (4)	0.028 (4)	0.002 (4)	0.013 (4)	−0.005 (4)
C7F	0.044 (5)	0.037 (5)	0.027 (5)	0.002 (5)	0.014 (5)	−0.002 (4)
C8F	0.038 (5)	0.035 (5)	0.027 (5)	−0.002 (5)	0.016 (4)	0.000 (5)
C9F	0.032 (5)	0.031 (5)	0.024 (4)	−0.004 (4)	0.013 (4)	0.002 (4)
C10C	0.0205 (8)	0.0199 (8)	0.0203 (7)	0.0013 (6)	0.0116 (6)	0.0010 (6)
C11C	0.0282 (9)	0.0286 (9)	0.0261 (9)	0.0041 (7)	0.0113 (7)	0.0050 (7)
C12C	0.0310 (10)	0.0445 (12)	0.0269 (9)	0.0118 (9)	0.0086 (8)	0.0082 (8)
C13C	0.0258 (9)	0.0548 (13)	0.0257 (9)	0.0058 (9)	0.0065 (7)	−0.0054 (9)
C14C	0.0263 (9)	0.0406 (11)	0.0326 (10)	−0.0062 (8)	0.0100 (8)	−0.0082 (8)
C15C	0.0240 (8)	0.0265 (9)	0.0273 (9)	−0.0025 (7)	0.0103 (7)	0.0004 (7)

Geometric parameters (Å, º)

O1A—C1A	1.241 (2)	C16E—H16O	0.9800
O1A—Na1A	2.9433 (17)	Na1F—N1B	2.21 (3)
O2A—C2A	1.250 (2)	Na1F—O3F	2.495 (17)
O2A—Na1C^i	2.254 (2)	Na1F—O2C	2.49 (3)
O2A—Na1B^ii	2.32 (3)	O3F—C16F	1.469 (15)
O2A—Na1F^ii	2.36 (4)	O3F—H3F	0.8423
O2A—Na1E^ii	2.36 (4)	C16F—H16P	0.9800
O2A—Na1G^i	2.47 (3)	C16F—H16Q	0.9800
Na1A—O2B	2.2580 (17)	C16F—H16R	0.9800
Na1A—O2C^ii	2.2817 (16)	N1B—C2B	1.371 (2)
Na1A—N1A	2.3488 (17)	N2B—C2B	1.352 (2)
Na1A—O3A	2.3661 (19)	N2B—C3B	1.445 (2)
Na1A—C1A	2.9790 (19)	N2B—H2B	0.881 (16)
Na1A—C16A	3.077 (3)	C2B—Na1C^ii	3.041 (3)
Na1A—Na1B^ii	3.53 (3)	C3B—C10B	1.531 (2)
Na1A—Na1C^ii	3.819 (2)	C3B—C4B	1.538 (3)
O3A—C16A	1.423 (3)	C3B—C4E	1.553 (14)
O3A—H3A	0.864 (17)	C4B—C5B	1.385 (4)
C16A—H16A	0.9800	C4B—C9B	1.387 (4)
C16A—H16B	0.9800	C5B—C6B	1.390 (3)
C16A—H16C	0.9800	C5B—H5B	0.9500
Na1D—O2C^ii	2.144 (13)	C6B—C7B	1.381 (4)
Na1D—O2B	2.179 (13)	C6B—H6B	0.9500
Na1D—N1A	2.422 (13)	C7B—C8B	1.377 (4)
Na1D—O3D	2.487 (17)	C7B—H7B	0.9500
Na1D—O4D	2.495 (18)	C8B—C9B	1.395 (3)
Na1D—C2C^ii	3.032 (13)	C8B—H8B	0.9500
Na1D—C16D	3.106 (18)	C9B—H9B	0.9500
Na1D—C1A	3.113 (13)	C4E—C9E	1.379 (18)
Na1D—Na1F^ii	3.70 (3)	C4E—C5E	1.391 (18)
Na1D—H4D	2.5982	C5E—C6E	1.407 (17)
O3D—C16D	1.406 (19)	C5E—H5E	0.9500
O3D—H3D	0.84 (2)	C6E—C7E	1.379 (18)
C16D—H16J	0.9800	C6E—H6E	0.9500
C16D—H16K	0.9800	C7E—C8E	1.371 (18)
C16D—H16L	0.9800	C7E—H7E	0.9500
O4D—H4C	0.8402	C8E—C9E	1.414 (17)
O4D—H4D	0.8410	C8E—H8E	0.9500
N1A—C1A	1.338 (2)	C9E—H9E	0.9500
N1A—C2A	1.369 (2)	C10B—C15B	1.391 (2)
N2A—C2A	1.353 (2)	C10B—C11B	1.393 (2)
N2A—C3A	1.447 (2)	C11B—C12B	1.396 (3)
N2A—H2A	0.874 (16)	C11B—H11B	0.9500
C1A—C3A	1.560 (2)	C12B—C13B	1.378 (3)
C2A—Na1B^ii	3.12 (3)	C12B—H12B	0.9500
C3A—C10A	1.539 (2)	C13B—C14B	1.384 (3)
C3A—C4A	1.538 (3)	C13B—H13B	0.9500
C3A—C4D	1.551 (15)	C14B—C15B	1.391 (3)
C4A—C9A	1.380 (3)	C14B—H14B	0.9500
C4A—C5A	1.397 (4)	C15B—H15B	0.9500
C5A—C6A	1.397 (3)	O1C—C1C	1.240 (2)
C5A—H5A	0.9500	O1C—Na1G	2.97 (3)
C6A—C7A	1.384 (3)	O2C—C2C	1.245 (2)
C6A—H6A	0.9500	Na1C—N1C	2.361 (2)
C7A—C8A	1.371 (3)	Na1C—O3C	2.393 (2)
C7A—H7A	0.9500	Na1C—C1C	3.070 (2)
C8A—C9A	1.397 (3)	O3C—C16C	1.403 (4)
C8A—H8A	0.9500	O3C—H3C	0.896 (17)
C9A—H9A	0.9500	C16C—H16G	0.9800
C4D—C9D	1.372 (18)	C16C—H16H	0.9800
C4D—C5D	1.400 (19)	C16C—H16I	0.9800
C5D—C6D	1.400 (17)	Na1G—N1C	2.16 (3)
C5D—H5D	0.9500	Na1G—O3G	2.379 (18)
C6D—C7D	1.393 (18)	Na1G—O4G	2.85 (4)
C6D—H6D	0.9500	Na1G—C1C	2.90 (3)
C7D—C8D	1.362 (19)	O3G—C16G	1.424 (17)
C7D—H7D	0.9500	O3G—H3G	0.8387
C8D—C9D	1.412 (18)	C16G—H16S	0.9800
C8D—H8D	0.9500	C16G—H16T	0.9800
C9D—H9D	0.9500	C16G—H16U	0.9800
C10A—C15A	1.391 (3)	O4G—H4E	0.8405
C10A—C11A	1.393 (3)	O4G—H4F	0.8425
C11A—C12A	1.398 (3)	N1C—C1C	1.340 (2)
C11A—H11A	0.9500	N1C—C2C	1.372 (2)
C12A—C13A	1.380 (4)	N2C—C2C	1.352 (2)
C12A—H12A	0.9500	N2C—C3C	1.444 (2)
C13A—C14A	1.383 (4)	N2C—H2C	0.876 (16)
C13A—H13A	0.9500	C1C—C3C	1.557 (2)
C14A—C15A	1.395 (3)	C3C—C10C	1.535 (2)
C14A—H14A	0.9500	C3C—C4C	1.538 (3)
C15A—H15A	0.9500	C3C—C4F	1.546 (14)
C1B—O1B	1.239 (2)	C4C—C9C	1.388 (3)
C1B—N1B	1.339 (2)	C4C—C5C	1.391 (3)
C1B—C3B	1.556 (2)	C5C—C6C	1.396 (3)
C1B—Na1F	2.83 (3)	C5C—H5C	0.9500
C1B—Na1E	2.97 (4)	C6C—C7C	1.380 (4)
C1B—Na1B	3.04 (3)	C6C—H6C	0.9500
O1B—Na1F	2.79 (4)	C7C—C8C	1.383 (4)
O1B—Na1E	2.87 (4)	C7C—H7C	0.9500
O1B—Na1B	2.94 (3)	C8C—C9C	1.398 (3)
O2B—C2B	1.247 (2)	C8C—H8C	0.9500
O2B—Na1C^ii	2.293 (3)	C9C—H9C	0.9500
O2B—Na1G^ii	2.32 (3)	C4F—C5F	1.376 (17)
Na1B—O2C	2.29 (3)	C4F—C9F	1.386 (17)
Na1B—N1B	2.44 (3)	C5F—C6F	1.408 (17)
Na1B—O3B	2.495 (10)	C5F—H5F	0.9500
Na1B—O4B	2.533 (11)	C6F—C7F	1.368 (18)
Na1B—Na1C^ii	3.58 (3)	C6F—H6F	0.9500
O3B—C16B	1.510 (9)	C7F—C8F	1.365 (18)
O3B—H3B	0.84 (2)	C7F—H7F	0.9500
C16B—H16D	0.9800	C8F—C9F	1.396 (17)
C16B—H16E	0.9800	C8F—H8F	0.9500
C16B—H16F	0.9800	C9F—H9F	0.9500
O4B—H4A	0.858 (17)	C10C—C15C	1.394 (2)
O4B—H4B	0.854 (18)	C10C—C11C	1.395 (2)
Na1E—O2C	2.30 (4)	C11C—C12C	1.390 (3)
Na1E—N1B	2.39 (4)	C11C—H11C	0.9500
Na1E—O3E	2.506 (13)	C12C—C13C	1.380 (3)
Na1E—Na1G^ii	3.80 (4)	C12C—H12C	0.9500
Na1E—H3E	2.61 (11)	C13C—C14C	1.382 (3)
O3E—C16E	1.453 (12)	C13C—H13C	0.9500
O3E—H3E	0.86 (2)	C14C—C15C	1.396 (3)
C16E—H16M	0.9800	C14C—H14C	0.9500
C16E—H16N	0.9800	C15C—H15C	0.9500
C1A—O1A—Na1A	79.53 (11)	N1B—Na1E—H3E	85.3 (15)
C2A—O2A—Na1C^i	132.44 (13)	O1B—Na1E—H3E	88 (2)
C2A—O2A—Na1B^ii	118.9 (7)	C1B—Na1E—H3E	85.6 (18)
Na1C^i—O2A—Na1B^ii	102.8 (6)	Na1G^ii—Na1E—H3E	95.3 (12)
C2A—O2A—Na1F^ii	125.1 (7)	C16E—O3E—Na1E	121.7 (10)
Na1C^i—O2A—Na1F^ii	97.5 (7)	C16E—O3E—H3E	107 (2)
C2A—O2A—Na1E^ii	119.8 (9)	Na1E—O3E—H3E	87 (7)
Na1C^i—O2A—Na1E^ii	101.1 (8)	O3E—C16E—H16M	109.5
C2A—O2A—Na1G^i	128.6 (7)	O3E—C16E—H16N	109.5
Na1B^ii—O2A—Na1G^i	105.5 (9)	H16M—C16E—H16N	109.5
O2B—Na1A—O2C^ii	110.56 (6)	O3E—C16E—H16O	109.5
O2B—Na1A—N1A	135.13 (7)	H16M—C16E—H16O	109.5
O2C^ii—Na1A—N1A	103.25 (6)	H16N—C16E—H16O	109.5
O2B—Na1A—O3A	111.33 (7)	N1B—Na1F—O2A^iii	102.8 (14)
O2C^ii—Na1A—O3A	88.28 (7)	N1B—Na1F—O3F	93.0 (10)
N1A—Na1A—O3A	98.02 (6)	O2A^iii—Na1F—O3F	83.4 (12)
O2B—Na1A—O1A	90.93 (5)	N1B—Na1F—O2C	139.0 (16)
O2C^ii—Na1A—O1A	152.41 (6)	O2A^iii—Na1F—O2C	114.4 (12)
O3A—Na1A—O1A	100.11 (6)	O3F—Na1F—O2C	107.4 (13)
O2B—Na1A—C1A	113.80 (6)	N1B—Na1F—O1B	52.8 (7)
O2C^ii—Na1A—C1A	129.03 (6)	O2A^iii—Na1F—O1B	155.3 (14)
O3A—Na1A—C1A	97.78 (6)	O3F—Na1F—O1B	100.0 (12)
O2B—Na1A—C16A	90.44 (8)	O2C—Na1F—O1B	88.1 (12)
O2C^ii—Na1A—C16A	80.38 (8)	O2A^iii—Na1F—C1B	130.3 (13)
N1A—Na1A—C16A	124.30 (7)	O3F—Na1F—C1B	95.5 (11)
O3A—Na1A—C16A	26.41 (7)	O2C—Na1F—C1B	113.2 (14)
O1A—Na1A—C16A	117.78 (7)	N1B—Na1F—Na1D^iii	168.1 (10)
C1A—Na1A—C16A	122.22 (7)	O2A^iii—Na1F—Na1D^iii	80.9 (9)
O2B—Na1A—Na1B^ii	145.6 (3)	O1B—Na1F—Na1D^iii	122.1 (11)
N1A—Na1A—Na1B^ii	64.0 (4)	C1B—Na1F—Na1D^iii	147.1 (13)
O3A—Na1A—Na1B^ii	88.38 (16)	C16F—O3F—Na1F	112.9 (16)
O1A—Na1A—Na1B^ii	113.8 (4)	C16F—O3F—H3F	107.3
C1A—Na1A—Na1B^ii	89.8 (4)	Na1F—O3F—H3F	122.6
C16A—Na1A—Na1B^ii	97.8 (3)	O3F—C16F—H16P	109.5
O2C^ii—Na1A—Na1C^ii	77.55 (5)	O3F—C16F—H16Q	109.5
N1A—Na1A—Na1C^ii	154.33 (6)	H16P—C16F—H16Q	109.5
O3A—Na1A—Na1C^ii	107.64 (6)	O3F—C16F—H16R	109.5
O1A—Na1A—Na1C^ii	123.44 (5)	H16P—C16F—H16R	109.5
C1A—Na1A—Na1C^ii	144.19 (5)	H16Q—C16F—H16R	109.5
C16A—Na1A—Na1C^ii	81.32 (6)	C1B—N1B—C2B	107.09 (14)
Na1B^ii—Na1A—Na1C^ii	115.2 (4)	C1B—N1B—Na1F	102.9 (10)
C16A—O3A—Na1A	105.90 (15)	C2B—N1B—Na1F	149.1 (10)
C16A—O3A—H3A	108.4 (16)	C1B—N1B—Na1E	102.0 (9)
Na1A—O3A—H3A	130 (2)	C2B—N1B—Na1E	150.7 (9)
O3A—C16A—H16A	109.5	C1B—N1B—Na1B	102.8 (6)
Na1A—C16A—H16A	89.7	C2B—N1B—Na1B	149.7 (7)
O3A—C16A—H16B	109.5	C2B—N2B—C3B	111.19 (14)
Na1A—C16A—H16B	155.4	C2B—N2B—H2B	121.0 (16)
H16A—C16A—H16B	109.5	C3B—N2B—H2B	127.3 (16)
O3A—C16A—H16C	109.5	O2B—C2B—N2B	123.52 (16)
Na1A—C16A—H16C	76.6	O2B—C2B—N1B	124.42 (16)
H16A—C16A—H16C	109.5	N2B—C2B—N1B	112.05 (15)
H16B—C16A—H16C	109.5	O2B—C2B—Na1C^ii	43.01 (9)
O2C^ii—Na1D—O2B	119.3 (6)	N2B—C2B—Na1C^ii	164.35 (13)
O2C^ii—Na1D—N1A	105.2 (5)	N1B—C2B—Na1C^ii	81.92 (10)
O2B—Na1D—N1A	135.4 (6)	N2B—C3B—C10B	113.36 (14)
O2C^ii—Na1D—O3D	92.3 (8)	N2B—C3B—C4B	112.01 (15)
O2B—Na1D—O3D	76.8 (7)	C10B—C3B—C4B	109.5 (3)
N1A—Na1D—O3D	99.4 (7)	N2B—C3B—C4E	104.7 (9)
O2C^ii—Na1D—O4D	82.5 (8)	C10B—C3B—C4E	111 (3)
O2B—Na1D—O4D	92.5 (7)	N2B—C3B—C1B	98.36 (13)
N1A—Na1D—O4D	96.5 (7)	C10B—C3B—C1B	111.41 (13)
O3D—Na1D—O4D	164.0 (10)	C4B—C3B—C1B	111.8 (3)
O2B—Na1D—C2C^ii	100.0 (4)	C4E—C3B—C1B	117 (3)
N1A—Na1D—C2C^ii	124.6 (5)	C5B—C4B—C9B	119.04 (19)
O3D—Na1D—C2C^ii	91.7 (8)	C5B—C4B—C3B	118.2 (3)
O4D—Na1D—C2C^ii	78.3 (8)	C9B—C4B—C3B	122.7 (2)
O2C^ii—Na1D—C16D	83.3 (10)	C4B—C5B—C6B	120.5 (2)
O2B—Na1D—C16D	61.2 (8)	C4B—C5B—H5B	119.8
N1A—Na1D—C16D	125.6 (7)	C6B—C5B—H5B	119.8
O4D—Na1D—C16D	137.8 (10)	C7B—C6B—C5B	120.3 (2)
C2C^ii—Na1D—C16D	75.1 (9)	C7B—C6B—H6B	119.8
O2C^ii—Na1D—C1A	128.7 (5)	C5B—C6B—H6B	119.8
O2B—Na1D—C1A	111.4 (5)	C8B—C7B—C6B	119.5 (2)
N1A—Na1D—C1A	24.09 (14)	C8B—C7B—H7B	120.2
O3D—Na1D—C1A	92.2 (7)	C6B—C7B—H7B	120.2
O4D—Na1D—C1A	102.8 (8)	C7B—C8B—C9B	120.4 (2)
C2C^ii—Na1D—C1A	148.4 (5)	C7B—C8B—H8B	119.8
C16D—Na1D—C1A	117.0 (7)	C9B—C8B—H8B	119.8
O2B—Na1D—Na1F^ii	159.2 (8)	C4B—C9B—C8B	120.2 (2)
N1A—Na1D—Na1F^ii	65.3 (7)	C4B—C9B—H9B	119.9
C2C^ii—Na1D—Na1F^ii	59.4 (7)	C8B—C9B—H9B	119.9
C1A—Na1D—Na1F^ii	89.3 (7)	C9E—C4E—C5E	118.7 (16)
O2C^ii—Na1D—H4D	101.3	C9E—C4E—C3B	121.4 (17)
O2B—Na1D—H4D	85.3	C5E—C4E—C3B	119.7 (16)
N1A—Na1D—H4D	89.5	C4E—C5E—C6E	120.3 (18)
O3D—Na1D—H4D	161.3	C4E—C5E—H5E	119.9
O4D—Na1D—H4D	18.9	C6E—C5E—H5E	119.9
C2C^ii—Na1D—H4D	96.8	C7E—C6E—C5E	118.2 (19)
C16D—Na1D—H4D	142.6	C7E—C6E—H6E	120.9
C1A—Na1D—H4D	89.3	C5E—C6E—H6E	120.9
Na1F^ii—Na1D—H4D	93.4	C8E—C7E—C6E	122.8 (19)
C16D—O3D—Na1D	102.3 (13)	C8E—C7E—H7E	118.6
C16D—O3D—H3D	113 (3)	C6E—C7E—H7E	118.6
Na1D—O3D—H3D	128 (10)	C7E—C8E—C9E	117.5 (18)
O3D—C16D—Na1D	51.5 (10)	C7E—C8E—H8E	121.2
O3D—C16D—H16J	109.5	C9E—C8E—H8E	121.2
Na1D—C16D—H16J	95.6	C4E—C9E—C8E	120.8 (18)
O3D—C16D—H16K	109.5	C4E—C9E—H9E	119.6
Na1D—C16D—H16K	153.4	C8E—C9E—H9E	119.6
H16J—C16D—H16K	109.5	C15B—C10B—C11B	119.12 (17)
O3D—C16D—H16L	109.5	C15B—C10B—C3B	120.58 (15)
Na1D—C16D—H16L	68.3	C11B—C10B—C3B	120.28 (16)
H16J—C16D—H16L	109.5	C10B—C11B—C12B	120.08 (18)
H16K—C16D—H16L	109.5	C10B—C11B—H11B	120.0
Na1D—O4D—H4C	129.0	C12B—C11B—H11B	120.0
Na1D—O4D—H4D	87.5	C13B—C12B—C11B	120.29 (19)
H4C—O4D—H4D	120.6	C13B—C12B—H12B	119.9
C1A—N1A—C2A	107.34 (14)	C11B—C12B—H12B	119.9
C1A—N1A—Na1A	104.43 (11)	C12B—C13B—C14B	119.96 (18)
C2A—N1A—Na1A	145.65 (12)	C12B—C13B—H13B	120.0
C1A—N1A—Na1D	108.3 (3)	C14B—C13B—H13B	120.0
C2A—N1A—Na1D	144.3 (3)	C13B—C14B—C15B	120.10 (19)
C2A—N2A—C3A	110.88 (14)	C13B—C14B—H14B	119.9
C2A—N2A—H2A	121.7 (16)	C15B—C14B—H14B	119.9
C3A—N2A—H2A	125.7 (16)	C10B—C15B—C14B	120.41 (18)
O1A—C1A—N1A	125.33 (16)	C10B—C15B—H15B	119.8
O1A—C1A—C3A	123.83 (16)	C14B—C15B—H15B	119.8
N1A—C1A—C3A	110.84 (14)	C1C—O1C—Na1G	74.5 (6)
O1A—C1A—Na1A	76.30 (10)	C2C—O2C—Na1D^iii	124.7 (4)
C3A—C1A—Na1A	158.30 (11)	C2C—O2C—Na1A^iii	128.36 (12)
O1A—C1A—Na1D	77.7 (3)	C2C—O2C—Na1B	130.2 (7)
C3A—C1A—Na1D	158.5 (3)	Na1A^iii—O2C—Na1B	101.0 (7)
O2A—C2A—N2A	123.38 (16)	C2C—O2C—Na1E	129.3 (9)
O2A—C2A—N1A	124.34 (16)	C2C—O2C—Na1F	126.5 (9)
N2A—C2A—N1A	112.28 (15)	Na1D^iii—O2C—Na1F	105.5 (9)
N2A—C2A—Na1B^ii	163.6 (5)	O2A^iv—Na1C—O2B^iii	124.52 (8)
N1A—C2A—Na1B^ii	83.9 (5)	O2A^iv—Na1C—N1C	131.17 (11)
N2A—C3A—C10A	112.11 (14)	O2B^iii—Na1C—N1C	97.07 (9)
N2A—C3A—C4A	113.74 (15)	O2A^iv—Na1C—O3C	91.45 (9)
C10A—C3A—C4A	108.9 (2)	O2B^iii—Na1C—O3C	100.09 (10)
N2A—C3A—C4D	105.5 (11)	N1C—Na1C—O3C	106.52 (7)
C10A—C3A—C4D	113 (2)	O2A^iv—Na1C—C2B^iii	105.14 (7)
N2A—C3A—C1A	98.63 (13)	O2B^iii—Na1C—C2B^iii	21.78 (5)
C10A—C3A—C1A	111.19 (13)	N1C—Na1C—C2B^iii	118.82 (9)
C4A—C3A—C1A	112.0 (3)	O3C—Na1C—C2B^iii	91.80 (8)
C4D—C3A—C1A	115 (3)	O2A^iv—Na1C—C1C	108.64 (9)
C9A—C4A—C5A	118.50 (19)	O2B^iii—Na1C—C1C	121.39 (8)
C9A—C4A—C3A	121.4 (3)	O3C—Na1C—C1C	101.50 (7)
C5A—C4A—C3A	119.9 (2)	C2B^iii—Na1C—C1C	143.16 (8)
C6A—C5A—C4A	120.35 (19)	O2B^iii—Na1C—Na1B^iii	88.5 (5)
C6A—C5A—H5A	119.8	N1C—Na1C—Na1B^iii	168.3 (3)
C4A—C5A—H5A	119.8	O3C—Na1C—Na1B^iii	82.5 (2)
C7A—C6A—C5A	120.23 (19)	C2B^iii—Na1C—Na1B^iii	67.3 (5)
C7A—C6A—H6A	119.9	C1C—Na1C—Na1B^iii	147.9 (4)
C5A—C6A—H6A	119.9	O2A^iv—Na1C—Na1A^iii	150.31 (7)
C8A—C7A—C6A	119.6 (2)	N1C—Na1C—Na1A^iii	64.43 (6)
C8A—C7A—H7A	120.2	O3C—Na1C—Na1A^iii	108.91 (7)
C6A—C7A—H7A	120.2	C2B^iii—Na1C—Na1A^iii	54.42 (5)
C7A—C8A—C9A	120.4 (2)	C1C—Na1C—Na1A^iii	88.74 (5)
C7A—C8A—H8A	119.8	Na1B^iii—Na1C—Na1A^iii	120.4 (5)
C9A—C8A—H8A	119.8	C16C—O3C—Na1C	110.32 (19)
C4A—C9A—C8A	120.9 (2)	C16C—O3C—H3C	109.1 (17)
C4A—C9A—H9A	119.5	Na1C—O3C—H3C	106 (2)
C8A—C9A—H9A	119.5	O3C—C16C—H16G	109.5
C9D—C4D—C5D	117 (2)	O3C—C16C—H16H	109.5
C9D—C4D—C3A	116 (2)	H16G—C16C—H16H	109.5
C5D—C4D—C3A	123 (2)	O3C—C16C—H16I	109.5
C4D—C5D—C6D	119.5 (16)	H16G—C16C—H16I	109.5
C4D—C5D—H5D	120.3	H16H—C16C—H16I	109.5
C6D—C5D—H5D	120.3	N1C—Na1G—O2B^iii	102.1 (12)
C7D—C6D—C5D	121.6 (18)	N1C—Na1G—O3G	95.7 (10)
C7D—C6D—H6D	119.2	O2B^iii—Na1G—O3G	95.8 (11)
C5D—C6D—H6D	119.2	N1C—Na1G—O2A^iv	130.2 (13)
C8D—C7D—C6D	118.3 (18)	O2B^iii—Na1G—O2A^iv	114.0 (10)
C8D—C7D—H7D	120.8	N1C—Na1G—O4G	95.5 (11)
C6D—C7D—H7D	120.8	O2B^iii—Na1G—O4G	66.4 (9)
C7D—C8D—C9D	120 (2)	O3G—Na1G—O4G	160.6 (16)
C7D—C8D—H8D	120.0	O2A^iv—Na1G—O4G	70.9 (8)
C9D—C8D—H8D	120.0	N1C—Na1G—C1C	25.9 (4)
C4D—C9D—C8D	122 (2)	O2B^iii—Na1G—C1C	127.6 (11)
C4D—C9D—H9D	119.1	O3G—Na1G—C1C	95.5 (10)
C8D—C9D—H9D	119.1	O2A^iv—Na1G—C1C	108.0 (11)
C15A—C10A—C11A	118.39 (18)	O4G—Na1G—C1C	101.5 (10)
C15A—C10A—C3A	120.85 (16)	N1C—Na1G—O1C	50.2 (6)
C11A—C10A—C3A	120.74 (16)	O2B^iii—Na1G—O1C	151.0 (12)
C10A—C11A—C12A	120.6 (2)	O3G—Na1G—O1C	95.6 (10)
C10A—C11A—H11A	119.7	O2A^iv—Na1G—O1C	85.7 (9)
C12A—C11A—H11A	119.7	O4G—Na1G—O1C	103.8 (10)
C13A—C12A—C11A	120.3 (2)	N1C—Na1G—Na1E^iii	163.5 (10)
C13A—C12A—H12A	119.9	O2B^iii—Na1G—Na1E^iii	81.7 (9)
C11A—C12A—H12A	119.9	O2A^iv—Na1G—Na1E^iii	37.1 (6)
C12A—C13A—C14A	119.7 (2)	C1C—Na1G—Na1E^iii	145.2 (11)
C12A—C13A—H13A	120.2	O1C—Na1G—Na1E^iii	122.3 (10)
C14A—C13A—H13A	120.2	C16G—O3G—Na1G	105.9 (19)
C13A—C14A—C15A	120.2 (2)	C16G—O3G—H3G	111.9
C13A—C14A—H14A	119.9	Na1G—O3G—H3G	102.7
C15A—C14A—H14A	119.9	O3G—C16G—H16S	109.5
C10A—C15A—C14A	120.86 (19)	O3G—C16G—H16T	109.5
C10A—C15A—H15A	119.6	H16S—C16G—H16T	109.5
C14A—C15A—H15A	119.6	O3G—C16G—H16U	109.5
O1B—C1B—N1B	125.04 (16)	H16S—C16G—H16U	109.5
O1B—C1B—C3B	123.78 (16)	H16T—C16G—H16U	109.5
N1B—C1B—C3B	111.18 (14)	Na1G—O4G—H4E	102.1
O1B—C1B—Na1F	75.8 (8)	Na1G—O4G—H4F	113.7
C3B—C1B—Na1F	159.4 (7)	H4E—O4G—H4F	120.2
O1B—C1B—Na1E	73.4 (7)	C1C—N1C—C2C	107.18 (14)
N1B—C1B—Na1E	51.8 (7)	C1C—N1C—Na1G	109.5 (9)
C3B—C1B—Na1E	162.6 (7)	C2C—N1C—Na1G	143.1 (9)
O1B—C1B—Na1B	73.5 (5)	C1C—N1C—Na1C	108.94 (12)
N1B—C1B—Na1B	51.8 (5)	C2C—N1C—Na1C	143.88 (13)
C3B—C1B—Na1B	162.1 (5)	C2C—N2C—C3C	111.17 (14)
C1B—O1B—Na1F	78.7 (7)	C2C—N2C—H2C	121.2 (16)
C1B—O1B—Na1E	82.2 (7)	C3C—N2C—H2C	125.4 (16)
C1B—O1B—Na1B	82.6 (5)	O1C—C1C—N1C	125.68 (16)
C2B—O2B—Na1D	134.4 (4)	O1C—C1C—C3C	123.32 (15)
C2B—O2B—Na1A	130.63 (12)	N1C—C1C—C3C	110.99 (14)
C2B—O2B—Na1C^ii	115.22 (12)	O1C—C1C—Na1G	81.1 (6)
Na1A—O2B—Na1C^ii	114.13 (7)	C3C—C1C—Na1G	155.3 (6)
C2B—O2B—Na1G^ii	120.1 (7)	O1C—C1C—Na1C	79.01 (11)
Na1A—O2B—Na1G^ii	109.0 (7)	N1C—C1C—Na1C	46.68 (9)
O2C—Na1B—O2A^iii	124.2 (12)	C3C—C1C—Na1C	157.67 (12)
O2C—Na1B—N1B	136.9 (12)	O2C—C2C—N2C	123.39 (16)
O2A^iii—Na1B—N1B	96.9 (9)	O2C—C2C—N1C	124.63 (16)
O2C—Na1B—O3B	87.6 (6)	N2C—C2C—N1C	111.98 (15)
O2A^iii—Na1B—O3B	86.4 (7)	N2C—C2C—Na1D^iii	158.9 (3)
N1B—Na1B—O3B	109.2 (8)	N1C—C2C—Na1D^iii	89.1 (3)
O2C—Na1B—O4B	82.8 (7)	N2C—C3C—C10C	111.96 (13)
O2A^iii—Na1B—O4B	84.5 (6)	N2C—C3C—C4C	112.03 (15)
N1B—Na1B—O4B	89.6 (5)	C10C—C3C—C4C	112.44 (15)
O3B—Na1B—O4B	160.0 (13)	N2C—C3C—C4F	117.1 (9)
O2C—Na1B—O1B	88.7 (9)	C10C—C3C—C4F	108.7 (9)
O2A^iii—Na1B—O1B	146.2 (11)	N2C—C3C—C1C	98.54 (13)
O3B—Na1B—O1B	104.0 (7)	C10C—C3C—C1C	111.23 (13)
O4B—Na1B—O1B	93.3 (6)	C4C—C3C—C1C	109.83 (15)
O2C—Na1B—C1B	112.4 (10)	C4F—C3C—C1C	109.0 (10)
O2A^iii—Na1B—C1B	122.4 (10)	C9C—C4C—C5C	118.91 (19)
O3B—Na1B—C1B	107.0 (8)	C9C—C4C—C3C	120.71 (19)
O4B—Na1B—C1B	92.9 (6)	C5C—C4C—C3C	120.3 (2)
O2C—Na1B—C2A^iii	103.7 (10)	C4C—C5C—C6C	120.1 (2)
N1B—Na1B—C2A^iii	116.9 (9)	C4C—C5C—H5C	120.0
O3B—Na1B—C2A^iii	84.4 (7)	C6C—C5C—H5C	120.0
O4B—Na1B—C2A^iii	80.9 (6)	C7C—C6C—C5C	120.8 (2)
O1B—Na1B—C2A^iii	165.4 (8)	C7C—C6C—H6C	119.6
C1B—Na1B—C2A^iii	142.3 (9)	C5C—C6C—H6C	119.6
O2A^iii—Na1B—Na1A^iii	84.9 (8)	C6C—C7C—C8C	119.5 (2)
N1B—Na1B—Na1A^iii	164.3 (4)	C6C—C7C—H7C	120.2
O3B—Na1B—Na1A^iii	86.5 (7)	C8C—C7C—H7C	120.2
O4B—Na1B—Na1A^iii	75.0 (6)	C7C—C8C—C9C	119.9 (2)
O1B—Na1B—Na1A^iii	127.2 (8)	C7C—C8C—H8C	120.0
C1B—Na1B—Na1A^iii	149.5 (9)	C9C—C8C—H8C	120.0
C2A^iii—Na1B—Na1A^iii	64.4 (5)	C4C—C9C—C8C	120.8 (2)
O2C—Na1B—Na1C^ii	154.8 (9)	C4C—C9C—H9C	119.6
N1B—Na1B—Na1C^ii	59.8 (5)	C8C—C9C—H9C	119.6
O3B—Na1B—Na1C^ii	105.0 (8)	C5F—C4F—C9F	117.2 (15)
O4B—Na1B—Na1C^ii	78.2 (5)	C5F—C4F—C3C	120.9 (17)
O1B—Na1B—Na1C^ii	108.6 (7)	C9F—C4F—C3C	121.9 (17)
C1B—Na1B—Na1C^ii	85.1 (6)	C4F—C5F—C6F	122.1 (16)
C2A^iii—Na1B—Na1C^ii	57.2 (4)	C4F—C5F—H5F	119.0
Na1A^iii—Na1B—Na1C^ii	118.4 (7)	C6F—C5F—H5F	119.0
C16B—O3B—Na1B	117.4 (7)	C7F—C6F—C5F	118.3 (18)
C16B—O3B—H3B	106 (2)	C7F—C6F—H6F	120.8
Na1B—O3B—H3B	108 (6)	C5F—C6F—H6F	120.8
O3B—C16B—H16D	109.5	C8F—C7F—C6F	121 (2)
O3B—C16B—H16E	109.5	C8F—C7F—H7F	119.7
H16D—C16B—H16E	109.5	C6F—C7F—H7F	119.7
O3B—C16B—H16F	109.5	C7F—C8F—C9F	120.0 (19)
H16D—C16B—H16F	109.5	C7F—C8F—H8F	120.0
H16E—C16B—H16F	109.5	C9F—C8F—H8F	120.0
Na1B—O4B—H4A	128 (2)	C4F—C9F—C8F	121.1 (17)
Na1B—O4B—H4B	110 (2)	C4F—C9F—H9F	119.4
H4A—O4B—H4B	106 (2)	C8F—C9F—H9F	119.4
O2C—Na1E—O2A^iii	121.9 (16)	C15C—C10C—C11C	118.32 (17)
O2C—Na1E—N1B	140.1 (17)	C15C—C10C—C3C	122.61 (15)
O2A^iii—Na1E—N1B	97.4 (12)	C11C—C10C—C3C	119.06 (16)
O2C—Na1E—O3E	84.4 (8)	C12C—C11C—C10C	120.82 (19)
O2A^iii—Na1E—O3E	103.0 (10)	C12C—C11C—H11C	119.6
N1B—Na1E—O3E	94.0 (11)	C10C—C11C—H11C	119.6
O2C—Na1E—O1B	90.1 (12)	C13C—C12C—C11C	120.27 (19)
O2A^iii—Na1E—O1B	147.9 (15)	C13C—C12C—H12C	119.9
N1B—Na1E—O1B	50.5 (7)	C11C—C12C—H12C	119.9
O3E—Na1E—O1B	80.6 (9)	C12C—C13C—C14C	119.78 (19)
O2C—Na1E—C1B	114.4 (14)	C12C—C13C—H13C	120.1
O2A^iii—Na1E—C1B	123.5 (13)	C14C—C13C—H13C	120.1
O3E—Na1E—C1B	86.0 (9)	C13C—C14C—C15C	120.2 (2)
O2C—Na1E—Na1G^ii	154.0 (13)	C13C—C14C—H14C	119.9
N1B—Na1E—Na1G^ii	60.0 (8)	C15C—C14C—H14C	119.9
O1B—Na1E—Na1G^ii	109.9 (11)	C10C—C15C—C14C	120.63 (18)
C1B—Na1E—Na1G^ii	86.0 (9)	C10C—C15C—H15C	119.7
O2C—Na1E—H3E	102.0 (8)	C14C—C15C—H15C	119.7
O2A^iii—Na1E—H3E	87.2 (18)
Na1A—O1A—C1A—N1A	9.09 (16)	Na1B—C1B—C3B—C10B	138.2 (7)
Na1A—O1A—C1A—C3A	−171.08 (16)	O1B—C1B—C3B—C4B	65.2 (3)
C2A—N1A—C1A—O1A	−178.36 (17)	N1B—C1B—C3B—C4B	−115.0 (2)
Na1A—N1A—C1A—O1A	−11.6 (2)	Na1B—C1B—C3B—C4B	−98.8 (7)
Na1D—N1A—C1A—O1A	0.0 (3)	O1B—C1B—C3B—C4E	71.6 (15)
C2A—N1A—C1A—C3A	1.80 (19)	N1B—C1B—C3B—C4E	−108.5 (15)
Na1A—N1A—C1A—C3A	168.55 (10)	Na1E—C1B—C3B—C4E	−97.3 (17)
Na1D—N1A—C1A—C3A	−179.9 (3)	N2B—C3B—C4B—C5B	37.0 (6)
C2A—N1A—C1A—Na1A	−166.75 (17)	C10B—C3B—C4B—C5B	−89.7 (4)
C2A—N1A—C1A—Na1D	−178.3 (3)	C1B—C3B—C4B—C5B	146.3 (4)
Na1C^i—O2A—C2A—N2A	27.4 (3)	N2B—C3B—C4B—C9B	−145.0 (4)
Na1B^ii—O2A—C2A—N2A	175.4 (3)	C10B—C3B—C4B—C9B	88.3 (5)
Na1F^ii—O2A—C2A—N2A	176.5 (7)	C1B—C3B—C4B—C9B	−35.7 (5)
Na1E^ii—O2A—C2A—N2A	172.9 (4)	C9B—C4B—C5B—C6B	0.6 (7)
Na1G^i—O2A—C2A—N2A	29.2 (8)	C3B—C4B—C5B—C6B	178.7 (3)
Na1C^i—O2A—C2A—N1A	−152.93 (15)	C4B—C5B—C6B—C7B	−0.6 (5)
Na1B^ii—O2A—C2A—N1A	−5.0 (3)	C5B—C6B—C7B—C8B	0.4 (4)
Na1F^ii—O2A—C2A—N1A	−3.8 (8)	C6B—C7B—C8B—C9B	−0.2 (5)
Na1E^ii—O2A—C2A—N1A	−7.5 (4)	C5B—C4B—C9B—C8B	−0.4 (7)
Na1G^i—O2A—C2A—N1A	−151.2 (7)	C3B—C4B—C9B—C8B	−178.4 (4)
Na1C^i—O2A—C2A—Na1B^ii	−148.0 (3)	C7B—C8B—C9B—C4B	0.2 (5)
C3A—N2A—C2A—O2A	−179.82 (16)	N2B—C3B—C4E—C9E	173 (6)
C3A—N2A—C2A—N1A	0.5 (2)	C10B—C3B—C4E—C9E	51 (7)
C3A—N2A—C2A—Na1B^ii	−169.2 (9)	C1B—C3B—C4E—C9E	−79 (7)
C1A—N1A—C2A—O2A	178.85 (17)	N2B—C3B—C4E—C5E	−1 (7)
Na1A—N1A—C2A—O2A	22.0 (3)	C10B—C3B—C4E—C5E	−124 (6)
Na1D—N1A—C2A—O2A	1.6 (5)	C1B—C3B—C4E—C5E	107 (6)
C1A—N1A—C2A—N2A	−1.5 (2)	C9E—C4E—C5E—C6E	13 (9)
Na1A—N1A—C2A—N2A	−158.30 (16)	C3B—C4E—C5E—C6E	−172 (4)
Na1D—N1A—C2A—N2A	−178.7 (5)	C4E—C5E—C6E—C7E	−7 (6)
C1A—N1A—C2A—Na1B^ii	175.6 (2)	C5E—C6E—C7E—C8E	3 (6)
Na1A—N1A—C2A—Na1B^ii	18.8 (3)	C6E—C7E—C8E—C9E	−4 (6)
C2A—N2A—C3A—C10A	−116.61 (16)	C5E—C4E—C9E—C8E	−15 (9)
C2A—N2A—C3A—C4A	119.3 (3)	C3B—C4E—C9E—C8E	170 (5)
C2A—N2A—C3A—C4D	119 (3)	C7E—C8E—C9E—C4E	11 (6)
C2A—N2A—C3A—C1A	0.54 (17)	N2B—C3B—C10B—C15B	169.05 (15)
O1A—C1A—C3A—N2A	178.70 (16)	C4B—C3B—C10B—C15B	−65.0 (2)
N1A—C1A—C3A—N2A	−1.44 (17)	C4E—C3B—C10B—C15B	−74 (2)
Na1A—C1A—C3A—N2A	22.8 (3)	C1B—C3B—C10B—C15B	59.2 (2)
Na1D—C1A—C3A—N2A	−1.7 (6)	N2B—C3B—C10B—C11B	−12.9 (2)
O1A—C1A—C3A—C10A	−63.4 (2)	C4B—C3B—C10B—C11B	113.0 (2)
N1A—C1A—C3A—C10A	116.41 (15)	C4E—C3B—C10B—C11B	105 (2)
Na1A—C1A—C3A—C10A	140.6 (3)	C1B—C3B—C10B—C11B	−122.70 (16)
Na1D—C1A—C3A—C10A	116.2 (6)	C15B—C10B—C11B—C12B	−2.1 (3)
O1A—C1A—C3A—C4A	58.7 (2)	C3B—C10B—C11B—C12B	179.82 (16)
N1A—C1A—C3A—C4A	−121.49 (18)	C10B—C11B—C12B—C13B	0.2 (3)
Na1A—C1A—C3A—C4A	−97.3 (3)	C11B—C12B—C13B—C14B	1.6 (3)
O1A—C1A—C3A—C4D	67.1 (13)	C12B—C13B—C14B—C15B	−1.5 (3)
N1A—C1A—C3A—C4D	−113.1 (13)	C11B—C10B—C15B—C14B	2.1 (3)
N2A—C3A—C4A—C9A	−158.3 (4)	C3B—C10B—C15B—C14B	−179.79 (16)
C10A—C3A—C4A—C9A	75.9 (5)	C13B—C14B—C15B—C10B	−0.3 (3)
C1A—C3A—C4A—C9A	−47.5 (5)	Na1G—O1C—C1C—N1C	2.8 (4)
N2A—C3A—C4A—C5A	26.2 (5)	Na1G—O1C—C1C—C3C	−176.2 (4)
C10A—C3A—C4A—C5A	−99.7 (4)	C2C—N1C—C1C—O1C	−179.42 (16)
C1A—C3A—C4A—C5A	136.9 (4)	Na1G—N1C—C1C—O1C	−3.9 (6)
C9A—C4A—C5A—C6A	1.3 (6)	Na1C—N1C—C1C—O1C	1.1 (2)
C3A—C4A—C5A—C6A	177.0 (3)	C2C—N1C—C1C—C3C	−0.40 (18)
C4A—C5A—C6A—C7A	−0.2 (4)	Na1G—N1C—C1C—C3C	175.2 (6)
C5A—C6A—C7A—C8A	−1.2 (4)	Na1C—N1C—C1C—C3C	−179.84 (11)
C6A—C7A—C8A—C9A	1.4 (5)	C2C—N1C—C1C—Na1G	−175.6 (6)
C5A—C4A—C9A—C8A	−1.0 (6)	C2C—N1C—C1C—Na1C	179.44 (18)
C3A—C4A—C9A—C8A	−176.7 (3)	Na1D^iii—O2C—C2C—N2C	178.3 (4)
C7A—C8A—C9A—C4A	−0.3 (6)	Na1A^iii—O2C—C2C—N2C	−167.07 (13)
N2A—C3A—C4D—C9D	−177 (5)	Na1B—O2C—C2C—N2C	21.8 (4)
C10A—C3A—C4D—C9D	60 (6)	Na1E—O2C—C2C—N2C	18.6 (5)
C1A—C3A—C4D—C9D	−70 (6)	Na1F—O2C—C2C—N2C	21.9 (7)
N2A—C3A—C4D—C5D	−18 (7)	Na1D^iii—O2C—C2C—N1C	−1.5 (4)
C10A—C3A—C4D—C5D	−141 (5)	Na1A^iii—O2C—C2C—N1C	13.2 (3)
C1A—C3A—C4D—C5D	90 (6)	Na1B—O2C—C2C—N1C	−158.0 (4)
C9D—C4D—C5D—C6D	−12 (8)	Na1E—O2C—C2C—N1C	−161.2 (5)
C3A—C4D—C5D—C6D	−171 (4)	Na1F—O2C—C2C—N1C	−157.9 (7)
C4D—C5D—C6D—C7D	6 (6)	Na1F—O2C—C2C—Na1D^iii	−156.3 (8)
C5D—C6D—C7D—C8D	−1 (5)	C3C—N2C—C2C—O2C	−176.03 (16)
C6D—C7D—C8D—C9D	2 (6)	C3C—N2C—C2C—N1C	3.8 (2)
C5D—C4D—C9D—C8D	14 (9)	C3C—N2C—C2C—Na1D^iii	−173.2 (6)
C3A—C4D—C9D—C8D	174 (4)	C1C—N1C—C2C—O2C	177.79 (17)
C7D—C8D—C9D—C4D	−9 (8)	Na1G—N1C—C2C—O2C	4.8 (10)
N2A—C3A—C10A—C15A	161.60 (15)	Na1C—N1C—C2C—O2C	−3.1 (3)
C4A—C3A—C10A—C15A	−71.7 (2)	C1C—N1C—C2C—N2C	−2.0 (2)
C4D—C3A—C10A—C15A	−79 (2)	Na1G—N1C—C2C—N2C	−175.0 (9)
C1A—C3A—C10A—C15A	52.3 (2)	Na1C—N1C—C2C—N2C	177.09 (16)
N2A—C3A—C10A—C11A	−20.2 (2)	C1C—N1C—C2C—Na1D^iii	176.9 (2)
C4A—C3A—C10A—C11A	106.6 (2)	C2C—N2C—C3C—C10C	−120.62 (15)
C4D—C3A—C10A—C11A	99 (2)	C2C—N2C—C3C—C4C	112.00 (18)
C1A—C3A—C10A—C11A	−129.52 (17)	C2C—N2C—C3C—C4F	112.9 (11)
C15A—C10A—C11A—C12A	−0.7 (3)	C2C—N2C—C3C—C1C	−3.53 (17)
C3A—C10A—C11A—C12A	−178.94 (17)	O1C—C1C—C3C—N2C	−178.58 (16)
C10A—C11A—C12A—C13A	0.1 (3)	N1C—C1C—C3C—N2C	2.37 (17)
C11A—C12A—C13A—C14A	0.4 (3)	Na1G—C1C—C3C—N2C	10.5 (11)
C12A—C13A—C14A—C15A	−0.3 (3)	Na1C—C1C—C3C—N2C	2.1 (3)
C11A—C10A—C15A—C14A	0.8 (3)	O1C—C1C—C3C—C10C	−60.9 (2)
C3A—C10A—C15A—C14A	179.04 (17)	N1C—C1C—C3C—C10C	120.02 (15)
C13A—C14A—C15A—C10A	−0.3 (3)	Na1G—C1C—C3C—C10C	128.2 (10)
N1B—C1B—O1B—Na1F	6.9 (5)	Na1C—C1C—C3C—C10C	119.7 (3)
C3B—C1B—O1B—Na1F	−173.2 (5)	O1C—C1C—C3C—C4C	64.2 (2)
N1B—C1B—O1B—Na1E	3.6 (3)	N1C—C1C—C3C—C4C	−114.85 (17)
C3B—C1B—O1B—Na1E	−176.6 (3)	Na1C—C1C—C3C—C4C	−115.2 (3)
N1B—C1B—O1B—Na1B	5.3 (3)	O1C—C1C—C3C—C4F	58.8 (10)
C3B—C1B—O1B—Na1B	−174.9 (3)	N1C—C1C—C3C—C4F	−120.2 (9)
O1B—C1B—N1B—C2B	178.70 (18)	Na1G—C1C—C3C—C4F	−112.0 (14)
C3B—C1B—N1B—C2B	−1.2 (2)	N2C—C3C—C4C—C9C	174.6 (2)
Na1F—C1B—N1B—C2B	−172.5 (7)	C10C—C3C—C4C—C9C	47.5 (3)
Na1E—C1B—N1B—C2B	−176.9 (4)	C1C—C3C—C4C—C9C	−77.0 (3)
Na1B—C1B—N1B—C2B	−174.9 (3)	N2C—C3C—C4C—C5C	−7.5 (3)
O1B—C1B—N1B—Na1F	−8.8 (7)	C10C—C3C—C4C—C5C	−134.6 (2)
C3B—C1B—N1B—Na1F	171.3 (6)	C1C—C3C—C4C—C5C	101.0 (3)
O1B—C1B—N1B—Na1E	−4.4 (4)	C9C—C4C—C5C—C6C	0.8 (4)
C3B—C1B—N1B—Na1E	175.7 (4)	C3C—C4C—C5C—C6C	−177.2 (2)
O1B—C1B—N1B—Na1B	−6.4 (4)	C4C—C5C—C6C—C7C	−0.1 (4)
C3B—C1B—N1B—Na1B	173.7 (3)	C5C—C6C—C7C—C8C	−1.0 (4)
Na1D—O2B—C2B—N2B	−7.8 (5)	C6C—C7C—C8C—C9C	1.3 (4)
Na1A—O2B—C2B—N2B	8.5 (3)	C5C—C4C—C9C—C8C	−0.4 (4)
Na1C^ii—O2B—C2B—N2B	−169.46 (15)	C3C—C4C—C9C—C8C	177.6 (2)
Na1G^ii—O2B—C2B—N2B	−164.1 (6)	C7C—C8C—C9C—C4C	−0.6 (4)
Na1D—O2B—C2B—N1B	171.8 (4)	N2C—C3C—C4F—C5F	28 (2)
Na1A—O2B—C2B—N1B	−171.88 (14)	C10C—C3C—C4F—C5F	−100.3 (17)
Na1C^ii—O2B—C2B—N1B	10.1 (3)	C1C—C3C—C4F—C5F	138.4 (17)
Na1G^ii—O2B—C2B—N1B	15.5 (6)	N2C—C3C—C4F—C9F	−153.0 (16)
Na1A—O2B—C2B—Na1C^ii	178.0 (2)	C10C—C3C—C4F—C9F	78.9 (19)
C3B—N2B—C2B—O2B	−177.05 (17)	C1C—C3C—C4F—C9F	−42 (2)
C3B—N2B—C2B—N1B	3.3 (2)	C9F—C4F—C5F—C6F	−6 (3)
C3B—N2B—C2B—Na1C^ii	155.4 (4)	C3C—C4F—C5F—C6F	173 (3)
C1B—N1B—C2B—O2B	179.13 (19)	C4F—C5F—C6F—C7F	10 (4)
Na1F—N1B—C2B—O2B	13.6 (14)	C5F—C6F—C7F—C8F	−8 (5)
Na1E—N1B—C2B—O2B	5.4 (8)	C6F—C7F—C8F—C9F	3 (6)
Na1B—N1B—C2B—O2B	9.1 (6)	C5F—C4F—C9F—C8F	1 (3)
C1B—N1B—C2B—N2B	−1.3 (2)	C3C—C4F—C9F—C8F	−178 (3)
Na1F—N1B—C2B—N2B	−166.8 (14)	C7F—C8F—C9F—C4F	1 (5)
Na1E—N1B—C2B—N2B	−175.0 (7)	N2C—C3C—C10C—C15C	153.65 (16)
Na1B—N1B—C2B—N2B	−171.3 (5)	C4C—C3C—C10C—C15C	−79.2 (2)
C1B—N1B—C2B—Na1C^ii	−173.92 (13)	C4F—C3C—C10C—C15C	−75.5 (10)
Na1B—N1B—C2B—Na1C^ii	16.0 (6)	C1C—C3C—C10C—C15C	44.5 (2)
C2B—N2B—C3B—C10B	−121.26 (16)	N2C—C3C—C10C—C11C	−27.6 (2)
C2B—N2B—C3B—C4B	114.2 (3)	C4C—C3C—C10C—C11C	99.60 (19)
C2B—N2B—C3B—C4E	118 (4)	C4F—C3C—C10C—C11C	103.3 (10)
C2B—N2B—C3B—C1B	−3.53 (18)	C1C—C3C—C10C—C11C	−136.74 (15)
O1B—C1B—C3B—N2B	−177.01 (17)	C15C—C10C—C11C—C12C	−1.4 (3)
N1B—C1B—C3B—N2B	2.84 (18)	C3C—C10C—C11C—C12C	179.72 (16)
Na1F—C1B—C3B—N2B	22.0 (17)	C10C—C11C—C12C—C13C	1.0 (3)
Na1E—C1B—C3B—N2B	14.1 (9)	C11C—C12C—C13C—C14C	0.1 (3)
Na1B—C1B—C3B—N2B	19.0 (7)	C12C—C13C—C14C—C15C	−0.8 (3)
O1B—C1B—C3B—C10B	−57.8 (2)	C11C—C10C—C15C—C14C	0.7 (3)
N1B—C1B—C3B—C10B	122.05 (16)	C3C—C10C—C15C—C14C	179.52 (16)
Na1F—C1B—C3B—C10B	141.2 (17)	C13C—C14C—C15C—C10C	0.4 (3)
Na1E—C1B—C3B—C10B	133.3 (9)

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