Pseudopolymorphism in brucine: brucine–water (1/2), the third crystal hydrate of brucine

The structure of a third pseudopolymorphic hydrate of brucine, brucine–water (1/2) [systematic name: 2,3-dimethoxy­strychnidin-10-one–water (1/2)], C₂₃H₂₆N₂O₄·2H₂O, has been determined at 130 K. The asymmetric unit comprises two independent brucine mol­ecules and four water mol­ecules of solvation. The four water mol­ecules form uncommon cyclic hydrogen-bonded homomolecular R₄⁴(8) tetra­mer rings, which then form primary hydrogen-bonded chain substructures extending down the 2₁ screw axis in the unit cell. The two brucine mol­ecules are linked peripherally to these substructures by either single O—H...N_brucine or asymmetric three-centre O—H...O_brucine hydrogen bonds.

S1. Comment

The common crystalline form of the alkaloid brucine is a tetrahydrate [brucine–water (1/4)], and we have completed the structure determination of this and another pseudopolymorphic hydrate, brucine–water (1/5.25), obtained from the attempted preparation of a brucine adduct with urea (Smith et al., 2006a). Other crystallographically characterized brucine pseudopolymorphs include anhydrous brucine, brucine–acetone (1/1) and brucine–2-propanol–water (1/1/2) (Bialońska & Ciunik, 2004a), and brucine–ethanol–water (1/1/2) (Glover et al., 1985). The 2-propanol–water and ethanol–water solvates are isomorphous.

In a number of these solvate structures, as well as in the proton-transfer compounds of brucine, it has been recognized (Gould & Walkinshaw, 1984; Bialońska & Ciunik, 2004b; Smith et al., 2006a,b) that the brucine species form regular undulating parallel or antiparallel host sheet substructures, accommodating the guest molecules in the interstitial cavities. Thus, molecules of solvation are similarly incorporated and associated through hydrogen bonding. In the orthorhombic P2₁2₁2₁ or monoclinic P2₁ examples, the presence of a ca 12.5 Å unit-cell repeat along a crystallographic 2₁ screw axis was reasonably indicative of this characteristic substructure, e.g. in brucine–2-propanol–water (1/1/2) (12.37 Å; Bialońska & Ciunik, 2004a) and brucine–ethanol–water (1/1/2) (12.34 Å; Glover et al., 1985) (both P2₁2₁2₁), or in the proton-transfer example brucinium-D-glucuronate (12.7 Å; P2₁; Dijksma et al., 1998). In examples where the ca 12.5 Å/P2₁ cell parameter/space group combination is not found, the characteristic structuring is usually absent, e.g. brucine–acetone (1/1) (7.14 Å; P2₁) in the present set of brucine solvates (see Table 1); brucine–water (1/4) (11.53 Å; P2₁2₁2₁), in which the structure is present, is the exception. On the basis of this generalization, the structure of the monoclinic dihydrate, brucine–water (1/2), (I), obtained from the attempted preparation of a brucine–diethanolamine adduct in 95% ethanol, was not expected to have the structuring (with b ca 7.45 Å; P2₁). This structuring was in fact found, distinguishing the structure from those of brucine–water (1/4) and brucine–water (1/5.25) (Smith et al., 2006a).

In (I), the asymmetric unit comprises two independent brucine molecules and four water molecules of solvation. The two brucine molecules (A and B) (Fig. 1) have the overall Cahn–Ingold–Prelog absolute configuration [C7(R), C8(S), C12(S), C13(R), C14(R), C16(S)] as found in strychnine (Peerdeman, 1956). Because of the rigid nature of the brucine molecular cage, both molecules, as expected, are conformationally identical, including the methoxy substituents at C2 and C3, which in all brucine structures lie essentially in the plane of the benzene ring. In the efflorescent brucine–water (1/5.25) structure, the asymmetric unit also comprises two independent brucine molecules together with 10.5 molecules of solvent water, some of these having split-occupancy sites. However, unlike this structure, in which one set of brucine molecules form the common undulating sheet substructure, in (I) there is no such structuring. Instead, the water molecules dominate the structure assembly, forming uncommon cyclic hydrogen-bonded tetramer units (graph set R₄⁴; Etter et al., 1990; Bernstein et al., 1995) (Figs. 2 and 3). These are analogous to the cyclic water pentamer units found in the structure of brucinium L-glycerate 4.75-hydrate (Białońska et al., 2005). In (I), O—H···O—H···O associations (O4W—H42W···O3Wⁱ; symmetry code as in Table 2) link the tetramers into chain structures which form down the 2₁ screw axis in the unit cell (Fig. 2).

The brucine molecules are linked peripherally to these water structures by hydrogen bonds; there is a single linear interaction with a nitrogen acceptor of a B molecule (O2W—H22W···N19Bⁱ), as well as an asymmetric three-centred interaction with the carbonyl O acceptor of an A molecule [O2W—H12W···O25A and O3W^vii—H32W···O25A; symmetry code: (vii) x + 1, y + 1/2, −z]. The second carbonyl O atom of molecule B (O25B) and atom N19A of molecule A are unassociated except for some weak C—H···O and C—H···N interactions. Unlike the structures of both of the other brucine hydrates (Smith et al., 2006a) there are no water-O-–H···O(methoxy) interactions in (I).

It can be assumed that formation of different pseudopolymorphic solvates of brucine depends not only upon solvent composition (Bernstein, 1987; Kumar et al., 1999) but, in the case of the pure hydrates, also upon the presence of additional non-incorporated but structure-influencing solute components, e.g. diethanolamine in the case of (I) and urea in brucine–water (1/5.25).

S2. Experimental

Brucine dihydrate (I) was obtained from the attempted preparation of a 1:1 brucine–diethanolamine adduct by refluxing 0.1 mmol quantities of brucine tetrahydrate and diethanolamine in 40 ml of 50% ethanol–water for 10 min. Colourless prismatic crystals were obtained after total room-temperature evaporation of the solvent.

S3. Refinement

H atoms potentially involved in hydrogen-bonding interactions were generally located by difference Fourier methods. Some of the H atoms on the water molecules could not be located and were included in the refinement at calculated sites dictated by the assumed hydrogen-bonding geometry, and their positional and isotropic displacement parameters were refined. However, because of the poor reflection–parameter ratio, these were fixed in the final refinement cycles. Brucine H atoms were included at calculated positions [C—H (aromatic) = 0.95 Å and C—H (aliphatic) = 0.98–1.00 Å] and treated as riding, with U_iso(H) values of 1.2U_eq(C). The absolute configuration determined for the parent strychnine (Peerdeman, 1956) was invoked. Friedel pairs were averaged for the data used in the refinement.

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Figures

	Fig. 1. The molecular configuration and atom numbering scheme for the two brucine molecules (A and B) and the four water molecules of solvation in the asymmetric unit in (I). The hydrogen bonding in the cyclic R4^4 tetrameric water units and the intra-unit hydrogen bonds are shown as dashed lines. Non-H atoms are shown as 40% probability displacement ellipsoids.
	Fig. 2. A perspective view of the intermolecular hydrogen-bonding in the water chain structure of (I), extending approximately down the b axial direction. Non-associative H atoms have been omitted. [Symmetry code (vii): −x + 1, y + 1/2, −z. [+x in the text?] For other symmetry codes, see Table 1.]
	Fig. 3. The infinite hydrogen-bonded water chain extension, viewed perpendicular to the (vertical) 21 screw axial direction.

2,3-dimethoxystrychnidin-10-one–water (1/2)

Crystal data

C23H26N2O4·2H2O	F(000) = 920
Mr = 430.49	Dx = 1.385 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2247 reflections
a = 15.178 (2) Å	θ = 2.2–22.5°
b = 7.4496 (12) Å	µ = 0.10 mm^−1
c = 19.751 (3) Å	T = 130 K
β = 112.397 (3)°	Needle prism, colourless
V = 2064.8 (5) Å^3	0.50 × 0.15 × 0.10 mm
Z = 4

Data collection

Bruker SMART CCD detector diffractometer	3072 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.064
Graphite monochromator	θmax = 25.0°, θmin = 1.1°
ϕ and ω scans	h = −18→17
9011 measured reflections	k = −8→8
3936 independent reflections	l = −23→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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.090	H-atom parameters constrained
S = 0.87	w = 1/[σ^2(Fo^2) + (0.0228P)^2] where P = (Fo^2 + 2Fc^2)/3
3936 reflections	(Δ/σ)max = 0.002
559 parameters	Δρmax = 0.20 e Å^−3
1 restraint	Δρmin = −0.21 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O2A	1.02901 (14)	0.6054 (3)	−0.07255 (11)	0.0278 (8)
O3A	0.84653 (14)	0.6008 (3)	−0.11663 (11)	0.0262 (8)
O24A	0.89307 (14)	0.4467 (3)	0.33436 (11)	0.0252 (8)
O25A	0.71927 (14)	0.5297 (3)	0.08191 (11)	0.0277 (8)
N9A	0.87634 (16)	0.5975 (4)	0.14129 (13)	0.0201 (8)
N19A	1.18956 (17)	0.6083 (4)	0.30024 (13)	0.0219 (8)
C1A	1.0496 (2)	0.6113 (4)	0.05644 (16)	0.0215 (11)
C2A	0.9942 (2)	0.6073 (5)	−0.01760 (16)	0.0207 (10)
C3A	0.8943 (2)	0.6041 (5)	−0.04229 (16)	0.0207 (11)
C4A	0.8489 (2)	0.6043 (4)	0.00704 (16)	0.0206 (10)
C5A	0.9064 (2)	0.6047 (5)	0.08094 (16)	0.0207 (10)
C6A	1.0040 (2)	0.6103 (4)	0.10623 (16)	0.0213 (11)
C7A	1.0475 (2)	0.6250 (4)	0.18871 (16)	0.0196 (10)
C8A	0.9613 (2)	0.5765 (4)	0.21021 (15)	0.0175 (10)
C10A	0.7902 (2)	0.5392 (5)	0.13894 (17)	0.0224 (11)
C11A	0.7898 (2)	0.4914 (5)	0.21251 (17)	0.0242 (11)
C12A	0.8733 (2)	0.3764 (5)	0.26255 (16)	0.0220 (11)
C13A	0.9569 (2)	0.3862 (4)	0.23659 (16)	0.0199 (10)
C14A	1.0543 (2)	0.3124 (4)	0.28679 (16)	0.0206 (11)
C15A	1.1177 (2)	0.3172 (4)	0.24164 (17)	0.0229 (11)
C16A	1.1374 (2)	0.5116 (4)	0.22927 (16)	0.0217 (11)
C17A	1.0842 (2)	0.8149 (5)	0.21584 (16)	0.0239 (11)
C18A	1.1437 (2)	0.7862 (4)	0.29657 (17)	0.0245 (11)
C20A	1.1964 (2)	0.5033 (5)	0.36549 (16)	0.0226 (11)
C21A	1.1029 (2)	0.4183 (4)	0.35748 (16)	0.0202 (10)
C22A	1.0629 (2)	0.4356 (5)	0.40620 (17)	0.0229 (11)
C23A	0.9668 (2)	0.3560 (5)	0.39307 (17)	0.0276 (11)
C25A	1.1299 (2)	0.5944 (5)	−0.05027 (17)	0.0268 (11)
C26A	0.7466 (2)	0.5770 (5)	−0.14394 (16)	0.0301 (13)
O2B	0.71802 (15)	−0.0587 (3)	0.19592 (11)	0.0260 (8)
O3B	0.84818 (15)	−0.1165 (3)	0.32365 (12)	0.0278 (8)
O24B	0.60877 (15)	0.7364 (3)	0.50260 (12)	0.0273 (8)
O25B	0.84595 (14)	0.3222 (3)	0.51311 (11)	0.0251 (8)
N9B	0.69484 (17)	0.3340 (3)	0.42709 (13)	0.0193 (9)
N19B	0.41355 (17)	0.5391 (4)	0.25021 (14)	0.0228 (9)
C1B	0.6343 (2)	0.1541 (4)	0.24436 (17)	0.0196 (10)
C2B	0.7080 (2)	0.0353 (4)	0.25201 (17)	0.0186 (10)
C3B	0.7796 (2)	0.0041 (4)	0.32181 (17)	0.0182 (10)
C4B	0.7794 (2)	0.0950 (4)	0.38260 (16)	0.0198 (10)
C5B	0.7068 (2)	0.2209 (4)	0.37289 (16)	0.0171 (10)
C6B	0.6350 (2)	0.2479 (4)	0.30590 (17)	0.0185 (10)
C7B	0.5589 (2)	0.3681 (4)	0.31311 (17)	0.0192 (10)
C8B	0.6103 (2)	0.4507 (4)	0.39112 (16)	0.0164 (10)
C10B	0.7676 (2)	0.3941 (4)	0.48820 (16)	0.0204 (11)
C11B	0.7442 (2)	0.5541 (4)	0.52529 (17)	0.0253 (11)
C12B	0.6824 (2)	0.7034 (5)	0.47523 (17)	0.0220 (11)
C13B	0.6464 (2)	0.6430 (4)	0.39494 (17)	0.0203 (11)
C14B	0.5769 (2)	0.7654 (4)	0.33695 (17)	0.0205 (11)
C15B	0.5661 (2)	0.6852 (4)	0.26260 (17)	0.0224 (11)
C16B	0.5125 (2)	0.5098 (4)	0.25234 (16)	0.0201 (10)
C17B	0.4715 (2)	0.2578 (5)	0.30893 (18)	0.0239 (11)
C18B	0.3953 (2)	0.4014 (4)	0.29790 (18)	0.0248 (11)
C20B	0.3987 (2)	0.7222 (5)	0.27247 (19)	0.0279 (11)
C21B	0.4788 (2)	0.7803 (4)	0.34072 (18)	0.0209 (11)
C22B	0.4674 (2)	0.8357 (5)	0.40075 (19)	0.0283 (11)
C23B	0.5489 (2)	0.8864 (5)	0.46998 (18)	0.0291 (12)
C25B	0.6519 (2)	−0.0183 (5)	0.12299 (17)	0.0356 (14)
C26B	0.9178 (2)	−0.1624 (5)	0.39351 (17)	0.0277 (11)
O1W	0.6147 (2)	0.3133 (5)	−0.05011 (18)	0.0588 (14)
O2W	0.6881 (2)	0.0167 (5)	−0.09986 (19)	0.0549 (13)
O4W	0.5606 (4)	−0.2384 (7)	−0.0802 (2)	0.0764 (17)
O3W	0.4750 (2)	0.0684 (7)	−0.0524 (2)	0.0790 (15)
H1A	1.11720	0.61470	0.07320	0.0260*
H4A	0.78140	0.60420	−0.00920	0.0250*
H8A	0.95770	0.66410	0.24750	0.0210*
H12A	0.85190	0.24880	0.26060	0.0260*
H13A	0.93710	0.31010	0.19150	0.0240*
H14A	1.04650	0.18500	0.29940	0.0250*
H16A	1.17830	0.51350	0.19980	0.0260*
H22A	1.09560	0.49970	0.45030	0.0280*
H25A	1.15420	0.49510	−0.01560	0.0400*
H26A	1.15890	0.70720	−0.02670	0.0400*
H27A	1.14590	0.57340	−0.09320	0.0400*
H28A	0.71680	0.68270	−0.13210	0.0450*
H29A	0.73130	0.47030	−0.12150	0.0450*
H30A	0.72240	0.56140	−0.19720	0.0450*
H31A	1.12340	0.86280	0.18980	0.0290*
H32A	1.03070	0.89830	0.20900	0.0290*
H33A	1.19240	0.88170	0.31540	0.0300*
H34A	1.10300	0.78610	0.32560	0.0300*
H35A	1.21770	0.58300	0.40880	0.0270*
H36A	1.24490	0.40800	0.37400	0.0270*
H37A	1.17840	0.25360	0.26820	0.0270*
H38A	1.08490	0.25650	0.19400	0.0270*
H39A	0.72980	0.42640	0.20480	0.0290*
H40A	0.78870	0.60420	0.23870	0.0290*
H41A	0.96700	0.22720	0.38080	0.0330*
H42A	0.95370	0.36540	0.43830	0.0330*
H1B	0.58420	0.17140	0.19800	0.0230*
H4B	0.82700	0.07290	0.42970	0.0240*
H8B	0.56720	0.44240	0.41870	0.0200*
H12B	0.72180	0.81440	0.48130	0.0260*
H13B	0.70430	0.63560	0.38250	0.0240*
H14B	0.60540	0.88800	0.34150	0.0250*
H16B	0.50730	0.45690	0.20440	0.0240*
H22B	0.40450	0.84360	0.39980	0.0340*
H25B	0.65540	0.10980	0.11310	0.0540*
H26B	0.58710	−0.04850	0.11860	0.0540*
H27B	0.66830	−0.08890	0.08750	0.0540*
H28B	0.88640	−0.21720	0.42350	0.0410*
H29B	0.95170	−0.05390	0.41780	0.0410*
H30B	0.96330	−0.24780	0.38730	0.0410*
H31B	0.45220	0.17290	0.26720	0.0290*
H32B	0.48420	0.18980	0.35480	0.0290*
H33B	0.33070	0.34980	0.27390	0.0290*
H34B	0.40110	0.45440	0.34540	0.0290*
H35B	0.33830	0.72570	0.28070	0.0330*
H36B	0.39280	0.80710	0.23240	0.0330*
H37B	0.53080	0.76950	0.22280	0.0270*
H38B	0.62970	0.66430	0.26100	0.0270*
H39B	0.80500	0.60880	0.55810	0.0310*
H40B	0.71100	0.50990	0.55650	0.0310*
H41B	0.58730	0.98100	0.45900	0.0350*
H42B	0.52340	0.93650	0.50530	0.0350*
H11W	0.570	0.234	−0.045	0.10*
H12W	0.646	0.362	−0.008	0.11*
H21W	0.668	0.115	−0.082	0.10*
H22W	0.666	0.024	−0.142	0.09*
H41W	0.601	−0.185	−0.080	0.10*
H42W	0.572	−0.292	−0.047	0.09*
H31W	0.490	−0.031	−0.061	0.11*
H32W	0.413	0.055	−0.062	0.10*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2A	0.0204 (12)	0.0464 (15)	0.0181 (12)	0.0003 (12)	0.0092 (10)	0.0021 (12)
O3A	0.0209 (12)	0.0389 (15)	0.0179 (12)	−0.0030 (12)	0.0065 (10)	−0.0004 (12)
O24A	0.0227 (12)	0.0339 (15)	0.0212 (13)	0.0000 (11)	0.0107 (10)	−0.0013 (12)
O25A	0.0149 (12)	0.0452 (16)	0.0208 (13)	−0.0032 (11)	0.0042 (10)	−0.0020 (12)
N9A	0.0145 (14)	0.0269 (16)	0.0185 (14)	−0.0022 (13)	0.0060 (11)	−0.0005 (14)
N19A	0.0200 (14)	0.0276 (16)	0.0184 (14)	−0.0043 (14)	0.0078 (12)	0.0005 (14)
C1A	0.0162 (17)	0.026 (2)	0.0225 (18)	−0.0015 (16)	0.0077 (14)	0.0018 (17)
C2A	0.0224 (17)	0.0222 (19)	0.0203 (18)	−0.0032 (16)	0.0114 (15)	0.0021 (16)
C3A	0.0249 (18)	0.022 (2)	0.0148 (17)	−0.0008 (16)	0.0073 (14)	0.0010 (16)
C4A	0.0182 (17)	0.0208 (19)	0.0221 (18)	−0.0015 (16)	0.0068 (14)	0.0031 (17)
C5A	0.0213 (18)	0.0208 (19)	0.0215 (17)	−0.0010 (16)	0.0099 (14)	0.0037 (17)
C6A	0.0216 (18)	0.023 (2)	0.0186 (17)	−0.0010 (16)	0.0070 (14)	0.0012 (17)
C7A	0.0182 (17)	0.023 (2)	0.0202 (17)	−0.0063 (15)	0.0101 (14)	0.0006 (16)
C8A	0.0181 (17)	0.0198 (19)	0.0158 (16)	−0.0004 (15)	0.0079 (14)	−0.0033 (15)
C10A	0.0194 (18)	0.023 (2)	0.0265 (19)	−0.0018 (15)	0.0108 (16)	−0.0023 (17)
C11A	0.0190 (17)	0.028 (2)	0.030 (2)	−0.0041 (16)	0.0142 (15)	−0.0031 (17)
C12A	0.0221 (18)	0.026 (2)	0.0193 (18)	−0.0057 (16)	0.0096 (14)	−0.0007 (16)
C13A	0.0181 (17)	0.024 (2)	0.0177 (17)	−0.0031 (15)	0.0068 (14)	−0.0053 (15)
C14A	0.0239 (18)	0.0189 (19)	0.0208 (18)	−0.0026 (15)	0.0104 (15)	0.0015 (16)
C15A	0.0206 (18)	0.028 (2)	0.0197 (18)	0.0037 (15)	0.0073 (15)	0.0014 (16)
C16A	0.0164 (17)	0.032 (2)	0.0187 (18)	−0.0047 (16)	0.0091 (14)	−0.0033 (16)
C17A	0.0196 (18)	0.031 (2)	0.0205 (19)	−0.0025 (16)	0.0070 (15)	0.0043 (17)
C18A	0.0236 (18)	0.026 (2)	0.0232 (19)	−0.0077 (16)	0.0080 (15)	−0.0017 (17)
C20A	0.0239 (18)	0.027 (2)	0.0173 (18)	−0.0006 (16)	0.0082 (14)	0.0016 (16)
C21A	0.0222 (18)	0.0179 (19)	0.0178 (17)	0.0039 (15)	0.0047 (14)	0.0048 (16)
C22A	0.0244 (18)	0.026 (2)	0.0155 (17)	0.0010 (16)	0.0044 (14)	−0.0012 (16)
C23A	0.029 (2)	0.036 (2)	0.0204 (19)	−0.0018 (17)	0.0124 (16)	0.0050 (18)
C25A	0.0215 (18)	0.034 (2)	0.0271 (19)	0.0020 (17)	0.0117 (15)	0.0028 (18)
C26A	0.0187 (18)	0.047 (3)	0.0209 (18)	−0.0011 (18)	0.0033 (15)	−0.0031 (19)
O2B	0.0265 (13)	0.0310 (14)	0.0198 (13)	0.0049 (11)	0.0081 (10)	−0.0048 (12)
O3B	0.0225 (13)	0.0320 (15)	0.0277 (13)	0.0083 (11)	0.0083 (11)	−0.0028 (12)
O24B	0.0271 (13)	0.0308 (14)	0.0278 (13)	0.0043 (11)	0.0147 (11)	0.0000 (12)
O25B	0.0180 (12)	0.0313 (14)	0.0224 (13)	0.0015 (11)	0.0036 (10)	−0.0014 (11)
N9B	0.0160 (14)	0.0196 (16)	0.0218 (15)	0.0008 (12)	0.0067 (12)	0.0000 (13)
N19B	0.0156 (14)	0.0207 (16)	0.0321 (17)	0.0018 (12)	0.0090 (12)	0.0012 (14)
C1B	0.0166 (17)	0.0201 (19)	0.0196 (18)	−0.0002 (14)	0.0042 (14)	0.0055 (15)
C2B	0.0193 (17)	0.0163 (18)	0.0220 (18)	−0.0029 (15)	0.0100 (15)	−0.0023 (15)
C3B	0.0133 (16)	0.0160 (18)	0.0280 (19)	−0.0019 (14)	0.0109 (14)	−0.0021 (16)
C4B	0.0148 (16)	0.0220 (19)	0.0210 (17)	−0.0001 (15)	0.0049 (14)	0.0064 (17)
C5B	0.0141 (16)	0.0181 (19)	0.0201 (18)	−0.0033 (14)	0.0078 (14)	0.0005 (15)
C6B	0.0148 (17)	0.0156 (18)	0.0244 (19)	−0.0029 (15)	0.0068 (14)	0.0002 (16)
C7B	0.0158 (17)	0.0196 (19)	0.0224 (18)	0.0004 (14)	0.0075 (14)	0.0035 (16)
C8B	0.0157 (16)	0.0157 (18)	0.0201 (17)	0.0047 (14)	0.0094 (14)	0.0034 (15)
C10B	0.0192 (18)	0.023 (2)	0.0194 (18)	−0.0010 (16)	0.0078 (15)	0.0091 (16)
C11B	0.0237 (18)	0.025 (2)	0.0236 (19)	−0.0011 (16)	0.0049 (15)	−0.0007 (17)
C12B	0.0205 (18)	0.022 (2)	0.0257 (19)	−0.0020 (15)	0.0114 (15)	−0.0020 (16)
C13B	0.0138 (17)	0.023 (2)	0.0267 (19)	−0.0006 (15)	0.0107 (15)	0.0003 (16)
C14B	0.0202 (18)	0.0169 (19)	0.0262 (19)	−0.0005 (15)	0.0110 (15)	0.0022 (16)
C15B	0.0209 (18)	0.023 (2)	0.0237 (19)	0.0045 (15)	0.0090 (15)	0.0039 (16)
C16B	0.0160 (17)	0.023 (2)	0.0191 (17)	0.0009 (15)	0.0042 (14)	0.0021 (16)
C17B	0.0152 (17)	0.025 (2)	0.0263 (19)	−0.0024 (16)	0.0021 (15)	0.0010 (17)
C18B	0.0143 (17)	0.026 (2)	0.031 (2)	−0.0010 (15)	0.0053 (15)	0.0029 (17)
C20B	0.0214 (19)	0.024 (2)	0.039 (2)	0.0057 (16)	0.0122 (17)	0.0068 (18)
C21B	0.0209 (18)	0.0136 (19)	0.0299 (19)	0.0015 (15)	0.0117 (15)	0.0051 (16)
C22B	0.0244 (19)	0.026 (2)	0.040 (2)	0.0080 (16)	0.0184 (17)	0.0031 (18)
C23B	0.031 (2)	0.029 (2)	0.031 (2)	0.0078 (18)	0.0161 (17)	−0.0019 (18)
C25B	0.037 (2)	0.047 (3)	0.020 (2)	0.001 (2)	0.0077 (17)	−0.0068 (19)
C26B	0.0208 (19)	0.025 (2)	0.033 (2)	0.0069 (16)	0.0055 (16)	−0.0022 (18)
O1W	0.058 (2)	0.073 (3)	0.049 (2)	−0.0112 (19)	0.0245 (18)	−0.0113 (19)
O2W	0.0350 (17)	0.091 (3)	0.0295 (19)	0.0044 (17)	0.0020 (15)	−0.011 (2)
O3W	0.0388 (19)	0.097 (3)	0.098 (3)	−0.017 (2)	0.0224 (19)	0.002 (3)
O4W	0.085 (3)	0.068 (3)	0.065 (3)	−0.024 (3)	0.016 (2)	0.016 (2)

Geometric parameters (Å, º)

O2A—C2A	1.376 (4)	C15A—H38A	0.9900
O2A—C25A	1.425 (4)	C16A—H16A	1.0000
O3A—C3A	1.368 (4)	C17A—H32A	0.9900
O3A—C26A	1.414 (4)	C17A—H31A	0.9900
O24A—C12A	1.432 (4)	C18A—H34A	0.9900
O24A—C23A	1.437 (4)	C18A—H33A	0.9900
O25A—C10A	1.228 (4)	C20A—H35A	0.9900
O2B—C2B	1.367 (4)	C20A—H36A	0.9900
O2B—C25B	1.439 (4)	C22A—H22A	0.9500
O3B—C3B	1.365 (4)	C23A—H41A	0.9900
O3B—C26B	1.424 (4)	C23A—H42A	0.9900
O24B—C23B	1.430 (4)	C25A—H25A	0.9800
O24B—C12B	1.436 (4)	C25A—H26A	0.9800
O25B—C10B	1.224 (4)	C25A—H27A	0.9800
O1W—H12W	0.87	C26A—H30A	0.9800
O1W—H11W	0.93	C26A—H28A	0.9800
O2W—H21W	0.91	C26A—H29A	0.9800
O2W—H22W	0.77	C1B—C2B	1.389 (4)
O3W—H32W	0.89	C1B—C6B	1.399 (4)
O3W—H31W	0.81	C2B—C3B	1.412 (4)
O4W—H41W	0.73	C3B—C4B	1.380 (4)
O4W—H42W	0.73	C4B—C5B	1.403 (4)
N9A—C10A	1.362 (4)	C5B—C6B	1.371 (4)
N9A—C5A	1.431 (4)	C6B—C7B	1.511 (5)
N9A—C8A	1.484 (4)	C7B—C8B	1.564 (4)
N19A—C16A	1.505 (4)	C7B—C16B	1.551 (4)
N19A—C20A	1.477 (4)	C7B—C17B	1.536 (5)
N19A—C18A	1.486 (4)	C8B—C13B	1.525 (4)
N9B—C10B	1.364 (4)	C10B—C11B	1.511 (4)
N9B—C8B	1.487 (4)	C11B—C12B	1.545 (5)
N9B—C5B	1.427 (4)	C12B—C13B	1.535 (4)
N19B—C20B	1.477 (5)	C13B—C14B	1.528 (4)
N19B—C16B	1.502 (4)	C14B—C15B	1.535 (4)
N19B—C18B	1.488 (4)	C14B—C21B	1.523 (5)
C1A—C2A	1.382 (4)	C15B—C16B	1.512 (4)
C1A—C6A	1.402 (4)	C17B—C18B	1.529 (5)
C2A—C3A	1.405 (5)	C20B—C21B	1.495 (5)
C3A—C4A	1.391 (4)	C21B—C22B	1.328 (5)
C4A—C5A	1.386 (4)	C22B—C23B	1.501 (5)
C5A—C6A	1.372 (5)	C1B—H1B	0.9500
C6A—C7A	1.511 (4)	C4B—H4B	0.9500
C7A—C17A	1.540 (5)	C8B—H8B	1.0000
C7A—C8A	1.564 (5)	C11B—H40B	0.9900
C7A—C16A	1.544 (4)	C11B—H39B	0.9900
C8A—C13A	1.521 (4)	C12B—H12B	1.0000
C10A—C11A	1.498 (4)	C13B—H13B	1.0000
C11A—C12A	1.537 (5)	C14B—H14B	1.0000
C12A—C13A	1.541 (5)	C15B—H38B	0.9900
C13A—C14A	1.534 (4)	C15B—H37B	0.9900
C14A—C21A	1.527 (4)	C16B—H16B	1.0000
C14A—C15A	1.542 (5)	C17B—H31B	0.9900
C15A—C16A	1.517 (4)	C17B—H32B	0.9900
C17A—C18A	1.519 (4)	C18B—H33B	0.9900
C20A—C21A	1.506 (5)	C18B—H34B	0.9900
C21A—C22A	1.325 (4)	C20B—H35B	0.9900
C22A—C23A	1.503 (5)	C20B—H36B	0.9900
C1A—H1A	0.9500	C22B—H22B	0.9500
C4A—H4A	0.9500	C23B—H42B	0.9900
C8A—H8A	1.0000	C23B—H41B	0.9900
C11A—H40A	0.9900	C25B—H26B	0.9800
C11A—H39A	0.9900	C25B—H27B	0.9800
C12A—H12A	1.0000	C25B—H25B	0.9800
C13A—H13A	1.0000	C26B—H29B	0.9800
C14A—H14A	1.0000	C26B—H30B	0.9800
C15A—H37A	0.9900	C26B—H28B	0.9800
C2A—O2A—C25A	116.6 (2)	O2A—C25A—H27A	109.00
C3A—O3A—C26A	117.7 (2)	O2A—C25A—H25A	109.00
C12A—O24A—C23A	115.6 (2)	H26A—C25A—H27A	109.00
C2B—O2B—C25B	117.0 (3)	H25A—C25A—H26A	110.00
C3B—O3B—C26B	117.4 (2)	H25A—C25A—H27A	109.00
C12B—O24B—C23B	114.6 (2)	H29A—C26A—H30A	109.00
H11W—O1W—H12W	109	H28A—C26A—H30A	109.00
H21W—O2W—H22W	107	O3A—C26A—H28A	110.00
H31W—O3W—H32W	102	O3A—C26A—H29A	109.00
C5A—N9A—C8A	109.1 (2)	H28A—C26A—H29A	109.00
C5A—N9A—C10A	126.2 (3)	O3A—C26A—H30A	109.00
C8A—N9A—C10A	119.0 (3)	C2B—C1B—C6B	119.0 (3)
C16A—N19A—C20A	113.4 (3)	O2B—C2B—C1B	124.9 (3)
C18A—N19A—C20A	113.0 (2)	O2B—C2B—C3B	115.2 (3)
C16A—N19A—C18A	108.1 (2)	C1B—C2B—C3B	120.0 (3)
H41W—O4W—H42W	113	C2B—C3B—C4B	120.9 (3)
C8B—N9B—C10B	119.4 (2)	O3B—C3B—C2B	115.5 (3)
C5B—N9B—C10B	124.5 (3)	O3B—C3B—C4B	123.7 (3)
C5B—N9B—C8B	108.7 (2)	C3B—C4B—C5B	118.1 (3)
C16B—N19B—C18B	107.9 (2)	N9B—C5B—C4B	127.6 (3)
C16B—N19B—C20B	113.0 (3)	N9B—C5B—C6B	110.8 (3)
C18B—N19B—C20B	111.2 (2)	C4B—C5B—C6B	121.6 (3)
C2A—C1A—C6A	118.6 (3)	C1B—C6B—C5B	120.4 (3)
O2A—C2A—C1A	125.0 (3)	C1B—C6B—C7B	128.7 (3)
O2A—C2A—C3A	114.5 (3)	C5B—C6B—C7B	110.6 (3)
C1A—C2A—C3A	120.6 (3)	C6B—C7B—C16B	117.9 (3)
C2A—C3A—C4A	120.9 (3)	C6B—C7B—C17B	110.7 (3)
O3A—C3A—C2A	115.7 (3)	C6B—C7B—C8B	102.4 (2)
O3A—C3A—C4A	123.4 (3)	C16B—C7B—C17B	101.2 (3)
C3A—C4A—C5A	117.2 (3)	C8B—C7B—C16B	113.8 (2)
N9A—C5A—C6A	109.9 (3)	C8B—C7B—C17B	111.1 (3)
N9A—C5A—C4A	127.2 (3)	C7B—C8B—C13B	117.0 (2)
C4A—C5A—C6A	122.9 (3)	N9B—C8B—C13B	107.3 (2)
C5A—C6A—C7A	111.3 (3)	N9B—C8B—C7B	104.9 (2)
C1A—C6A—C7A	128.8 (3)	O25B—C10B—C11B	121.5 (3)
C1A—C6A—C5A	119.9 (3)	N9B—C10B—C11B	115.3 (3)
C6A—C7A—C17A	113.2 (2)	O25B—C10B—N9B	123.2 (3)
C6A—C7A—C16A	117.2 (3)	C10B—C11B—C12B	117.1 (3)
C6A—C7A—C8A	102.1 (2)	O24B—C12B—C11B	104.6 (2)
C8A—C7A—C16A	113.5 (2)	O24B—C12B—C13B	114.7 (3)
C8A—C7A—C17A	110.3 (2)	C11B—C12B—C13B	109.9 (3)
C16A—C7A—C17A	101.0 (2)	C8B—C13B—C14B	113.0 (3)
N9A—C8A—C13A	106.0 (2)	C12B—C13B—C14B	118.2 (3)
C7A—C8A—C13A	117.3 (3)	C8B—C13B—C12B	107.8 (3)
N9A—C8A—C7A	104.5 (2)	C15B—C14B—C21B	109.0 (3)
O25A—C10A—N9A	123.0 (3)	C13B—C14B—C15B	106.0 (2)
O25A—C10A—C11A	123.3 (3)	C13B—C14B—C21B	114.5 (3)
N9A—C10A—C11A	113.7 (3)	C14B—C15B—C16B	108.7 (3)
C10A—C11A—C12A	116.7 (3)	N19B—C16B—C15B	111.1 (3)
C11A—C12A—C13A	110.0 (3)	C7B—C16B—C15B	115.0 (3)
O24A—C12A—C13A	115.1 (3)	N19B—C16B—C7B	106.0 (2)
O24A—C12A—C11A	104.1 (3)	C7B—C17B—C18B	103.0 (3)
C8A—C13A—C14A	113.5 (3)	N19B—C18B—C17B	105.0 (3)
C12A—C13A—C14A	118.7 (3)	N19B—C20B—C21B	111.8 (3)
C8A—C13A—C12A	107.9 (3)	C14B—C21B—C20B	114.2 (3)
C13A—C14A—C15A	106.1 (2)	C20B—C21B—C22B	123.9 (3)
C15A—C14A—C21A	109.1 (3)	C14B—C21B—C22B	121.9 (3)
C13A—C14A—C21A	114.6 (3)	C21B—C22B—C23B	123.3 (3)
C14A—C15A—C16A	108.7 (2)	O24B—C23B—C22B	112.1 (3)
N19A—C16A—C15A	111.9 (2)	C6B—C1B—H1B	121.00
N19A—C16A—C7A	105.6 (2)	C2B—C1B—H1B	120.00
C7A—C16A—C15A	114.6 (3)	C3B—C4B—H4B	121.00
C7A—C17A—C18A	103.2 (3)	C5B—C4B—H4B	121.00
N19A—C18A—C17A	104.9 (2)	C13B—C8B—H8B	109.00
N19A—C20A—C21A	112.4 (2)	C7B—C8B—H8B	109.00
C14A—C21A—C20A	114.9 (3)	N9B—C8B—H8B	109.00
C14A—C21A—C22A	121.3 (3)	C10B—C11B—H40B	108.00
C20A—C21A—C22A	123.8 (3)	C12B—C11B—H39B	108.00
C21A—C22A—C23A	121.3 (3)	C10B—C11B—H39B	108.00
O24A—C23A—C22A	111.1 (3)	C12B—C11B—H40B	108.00
C6A—C1A—H1A	121.00	H39B—C11B—H40B	107.00
C2A—C1A—H1A	121.00	O24B—C12B—H12B	109.00
C3A—C4A—H4A	121.00	C13B—C12B—H12B	109.00
C5A—C4A—H4A	121.00	C11B—C12B—H12B	109.00
C13A—C8A—H8A	110.00	C8B—C13B—H13B	106.00
C7A—C8A—H8A	110.00	C12B—C13B—H13B	106.00
N9A—C8A—H8A	110.00	C14B—C13B—H13B	106.00
C12A—C11A—H39A	108.00	C21B—C14B—H14B	109.00
C10A—C11A—H39A	108.00	C13B—C14B—H14B	109.00
C12A—C11A—H40A	108.00	C15B—C14B—H14B	109.00
H39A—C11A—H40A	107.00	C14B—C15B—H38B	110.00
C10A—C11A—H40A	108.00	C16B—C15B—H37B	110.00
C11A—C12A—H12A	109.00	C16B—C15B—H38B	110.00
C13A—C12A—H12A	109.00	C14B—C15B—H37B	110.00
O24A—C12A—H12A	109.00	H37B—C15B—H38B	108.00
C12A—C13A—H13A	105.00	N19B—C16B—H16B	108.00
C8A—C13A—H13A	105.00	C7B—C16B—H16B	108.00
C14A—C13A—H13A	105.00	C15B—C16B—H16B	108.00
C15A—C14A—H14A	109.00	C7B—C17B—H32B	111.00
C21A—C14A—H14A	109.00	C18B—C17B—H31B	111.00
C13A—C14A—H14A	109.00	C7B—C17B—H31B	111.00
C14A—C15A—H38A	110.00	H31B—C17B—H32B	109.00
C14A—C15A—H37A	110.00	C18B—C17B—H32B	111.00
C16A—C15A—H38A	110.00	C17B—C18B—H34B	111.00
C16A—C15A—H37A	110.00	C17B—C18B—H33B	111.00
H37A—C15A—H38A	108.00	N19B—C18B—H33B	111.00
C15A—C16A—H16A	108.00	H33B—C18B—H34B	109.00
C7A—C16A—H16A	108.00	N19B—C18B—H34B	111.00
N19A—C16A—H16A	108.00	N19B—C20B—H35B	109.00
C18A—C17A—H31A	111.00	N19B—C20B—H36B	109.00
C7A—C17A—H32A	111.00	C21B—C20B—H35B	109.00
C7A—C17A—H31A	111.00	C21B—C20B—H36B	109.00
C18A—C17A—H32A	111.00	H35B—C20B—H36B	108.00
H31A—C17A—H32A	109.00	C23B—C22B—H22B	118.00
H33A—C18A—H34A	109.00	C21B—C22B—H22B	118.00
C17A—C18A—H33A	111.00	O24B—C23B—H41B	109.00
C17A—C18A—H34A	111.00	O24B—C23B—H42B	109.00
N19A—C18A—H33A	111.00	H41B—C23B—H42B	108.00
N19A—C18A—H34A	111.00	C22B—C23B—H41B	109.00
N19A—C20A—H35A	109.00	C22B—C23B—H42B	109.00
C21A—C20A—H35A	109.00	O2B—C25B—H26B	110.00
C21A—C20A—H36A	109.00	O2B—C25B—H27B	109.00
H35A—C20A—H36A	108.00	H25B—C25B—H26B	110.00
N19A—C20A—H36A	109.00	H25B—C25B—H27B	109.00
C21A—C22A—H22A	119.00	O2B—C25B—H25B	109.00
C23A—C22A—H22A	119.00	H26B—C25B—H27B	109.00
O24A—C23A—H42A	109.00	H28B—C26B—H30B	109.00
O24A—C23A—H41A	109.00	H29B—C26B—H30B	109.00
C22A—C23A—H41A	109.00	H28B—C26B—H29B	109.00
H41A—C23A—H42A	108.00	O3B—C26B—H28B	109.00
C22A—C23A—H42A	109.00	O3B—C26B—H29B	110.00
O2A—C25A—H26A	109.00	O3B—C26B—H30B	109.00
C25A—O2A—C2A—C1A	4.5 (5)	C7A—C8A—C13A—C14A	40.0 (3)
C25A—O2A—C2A—C3A	−175.3 (3)	O25A—C10A—C11A—C12A	135.3 (4)
C26A—O3A—C3A—C2A	173.0 (3)	N9A—C10A—C11A—C12A	−45.8 (4)
C26A—O3A—C3A—C4A	−7.0 (5)	C10A—C11A—C12A—O24A	142.5 (3)
C23A—O24A—C12A—C11A	177.3 (3)	C10A—C11A—C12A—C13A	18.7 (4)
C23A—O24A—C12A—C13A	−62.3 (4)	C11A—C12A—C13A—C8A	37.3 (3)
C12A—O24A—C23A—C22A	88.8 (3)	O24A—C12A—C13A—C8A	−79.9 (3)
C25B—O2B—C2B—C3B	−174.2 (3)	C11A—C12A—C13A—C14A	168.1 (3)
C25B—O2B—C2B—C1B	6.0 (4)	O24A—C12A—C13A—C14A	51.0 (4)
C26B—O3B—C3B—C2B	−175.4 (3)	C8A—C13A—C14A—C15A	−59.4 (3)
C26B—O3B—C3B—C4B	6.2 (4)	C8A—C13A—C14A—C21A	61.1 (3)
C12B—O24B—C23B—C22B	86.4 (3)	C12A—C13A—C14A—C15A	172.3 (3)
C23B—O24B—C12B—C13B	−66.8 (4)	C12A—C13A—C14A—C21A	−67.3 (4)
C23B—O24B—C12B—C11B	172.7 (2)	C21A—C14A—C15A—C16A	−55.6 (3)
C8A—N9A—C5A—C6A	−6.7 (4)	C15A—C14A—C21A—C20A	1.4 (4)
C5A—N9A—C10A—O25A	−19.8 (6)	C13A—C14A—C21A—C20A	−117.4 (3)
C10A—N9A—C5A—C4A	19.8 (6)	C13A—C14A—C21A—C22A	61.0 (4)
C10A—N9A—C5A—C6A	−159.5 (3)	C13A—C14A—C15A—C16A	68.4 (3)
C5A—N9A—C8A—C7A	15.3 (3)	C15A—C14A—C21A—C22A	179.8 (3)
C5A—N9A—C8A—C13A	−109.3 (3)	C14A—C15A—C16A—C7A	−59.0 (3)
C10A—N9A—C8A—C7A	170.3 (3)	C14A—C15A—C16A—N19A	61.1 (3)
C10A—N9A—C8A—C13A	45.7 (4)	C7A—C17A—C18A—N19A	36.1 (3)
C8A—N9A—C5A—C4A	172.6 (3)	N19A—C20A—C21A—C14A	50.5 (4)
C8A—N9A—C10A—C11A	11.0 (4)	N19A—C20A—C21A—C22A	−127.8 (3)
C5A—N9A—C10A—C11A	161.4 (3)	C20A—C21A—C22A—C23A	176.5 (3)
C8A—N9A—C10A—O25A	−170.1 (3)	C14A—C21A—C22A—C23A	−1.7 (5)
C16A—N19A—C18A—C17A	−16.3 (3)	C21A—C22A—C23A—O24A	−68.2 (4)
C18A—N19A—C16A—C7A	−9.9 (3)	C6B—C1B—C2B—O2B	−177.1 (3)
C18A—N19A—C16A—C15A	−135.2 (3)	C6B—C1B—C2B—C3B	3.1 (5)
C20A—N19A—C16A—C7A	116.2 (3)	C2B—C1B—C6B—C5B	−0.9 (5)
C20A—N19A—C16A—C15A	−9.1 (4)	C2B—C1B—C6B—C7B	−173.1 (3)
C20A—N19A—C18A—C17A	−142.6 (3)	O2B—C2B—C3B—O3B	−0.6 (4)
C16A—N19A—C20A—C21A	−46.0 (4)	O2B—C2B—C3B—C4B	177.9 (3)
C18A—N19A—C20A—C21A	77.5 (3)	C1B—C2B—C3B—O3B	179.2 (3)
C5B—N9B—C8B—C7B	12.2 (3)	C1B—C2B—C3B—C4B	−2.3 (5)
C5B—N9B—C8B—C13B	−112.8 (3)	O3B—C3B—C4B—C5B	177.5 (3)
C10B—N9B—C8B—C7B	163.4 (3)	C2B—C3B—C4B—C5B	−0.8 (5)
C10B—N9B—C8B—C13B	38.4 (4)	C3B—C4B—C5B—N9B	−177.5 (3)
C8B—N9B—C5B—C4B	177.7 (3)	C3B—C4B—C5B—C6B	3.2 (5)
C8B—N9B—C5B—C6B	−2.9 (3)	N9B—C5B—C6B—C1B	178.2 (3)
C10B—N9B—C5B—C4B	28.3 (5)	N9B—C5B—C6B—C7B	−8.3 (4)
C10B—N9B—C5B—C6B	−152.3 (3)	C4B—C5B—C6B—C1B	−2.3 (5)
C8B—N9B—C10B—C11B	15.5 (4)	C4B—C5B—C6B—C7B	171.2 (3)
C5B—N9B—C10B—O25B	−20.0 (5)	C1B—C6B—C7B—C8B	−172.0 (3)
C5B—N9B—C10B—C11B	161.9 (3)	C1B—C6B—C7B—C16B	−46.3 (5)
C8B—N9B—C10B—O25B	−166.4 (3)	C1B—C6B—C7B—C17B	69.5 (4)
C18B—N19B—C16B—C7B	−8.9 (3)	C5B—C6B—C7B—C8B	15.1 (3)
C18B—N19B—C16B—C15B	−134.4 (3)	C5B—C6B—C7B—C16B	140.9 (3)
C20B—N19B—C16B—C7B	114.5 (3)	C5B—C6B—C7B—C17B	−103.3 (3)
C18B—N19B—C20B—C21B	75.1 (3)	C6B—C7B—C8B—N9B	−16.0 (3)
C20B—N19B—C16B—C15B	−11.0 (3)	C6B—C7B—C8B—C13B	102.7 (3)
C16B—N19B—C18B—C17B	−16.9 (3)	C16B—C7B—C8B—N9B	−144.3 (3)
C20B—N19B—C18B—C17B	−141.4 (3)	C16B—C7B—C8B—C13B	−25.7 (4)
C16B—N19B—C20B—C21B	−46.4 (4)	C17B—C7B—C8B—N9B	102.2 (3)
C2A—C1A—C6A—C5A	0.3 (5)	C17B—C7B—C8B—C13B	−139.1 (3)
C2A—C1A—C6A—C7A	−176.0 (3)	C6B—C7B—C16B—N19B	151.6 (3)
C6A—C1A—C2A—C3A	0.6 (5)	C6B—C7B—C16B—C15B	−85.4 (3)
C6A—C1A—C2A—O2A	−179.1 (3)	C8B—C7B—C16B—N19B	−88.5 (3)
C1A—C2A—C3A—O3A	179.8 (3)	C8B—C7B—C16B—C15B	34.5 (4)
C1A—C2A—C3A—C4A	−0.2 (5)	C17B—C7B—C16B—N19B	30.7 (3)
O2A—C2A—C3A—O3A	−0.4 (5)	C17B—C7B—C16B—C15B	153.7 (3)
O2A—C2A—C3A—C4A	179.6 (3)	C6B—C7B—C17B—C18B	−166.5 (3)
O3A—C3A—C4A—C5A	178.9 (3)	C8B—C7B—C17B—C18B	80.5 (3)
C2A—C3A—C4A—C5A	−1.1 (5)	C16B—C7B—C17B—C18B	−40.6 (3)
C3A—C4A—C5A—N9A	−177.2 (3)	N9B—C8B—C13B—C12B	−69.7 (3)
C3A—C4A—C5A—C6A	2.0 (5)	N9B—C8B—C13B—C14B	157.9 (2)
C4A—C5A—C6A—C1A	−1.6 (5)	C7B—C8B—C13B—C12B	173.0 (3)
C4A—C5A—C6A—C7A	175.2 (3)	C7B—C8B—C13B—C14B	40.5 (4)
N9A—C5A—C6A—C1A	177.7 (3)	O25B—C10B—C11B—C12B	141.5 (3)
N9A—C5A—C6A—C7A	−5.4 (4)	N9B—C10B—C11B—C12B	−40.3 (4)
C1A—C6A—C7A—C8A	−169.1 (3)	C10B—C11B—C12B—O24B	130.8 (3)
C1A—C6A—C7A—C16A	−44.6 (4)	C10B—C11B—C12B—C13B	7.3 (4)
C1A—C6A—C7A—C17A	72.4 (4)	O24B—C12B—C13B—C8B	−72.2 (3)
C5A—C6A—C7A—C17A	−104.1 (3)	O24B—C12B—C13B—C14B	57.5 (4)
C5A—C6A—C7A—C8A	14.4 (3)	C11B—C12B—C13B—C8B	45.3 (3)
C5A—C6A—C7A—C16A	138.9 (3)	C11B—C12B—C13B—C14B	174.9 (3)
C17A—C7A—C16A—N19A	31.4 (3)	C8B—C13B—C14B—C15B	−61.2 (3)
C8A—C7A—C17A—C18A	79.1 (3)	C8B—C13B—C14B—C21B	59.0 (3)
C17A—C7A—C16A—C15A	155.0 (3)	C12B—C13B—C14B—C15B	171.6 (3)
C6A—C7A—C17A—C18A	−167.3 (3)	C12B—C13B—C14B—C21B	−68.2 (4)
C8A—C7A—C16A—C15A	37.0 (3)	C13B—C14B—C15B—C16B	69.3 (3)
C6A—C7A—C8A—N9A	−17.3 (3)	C21B—C14B—C15B—C16B	−54.4 (3)
C6A—C7A—C8A—C13A	99.8 (3)	C13B—C14B—C21B—C20B	−120.8 (3)
C16A—C7A—C8A—N9A	−144.3 (2)	C13B—C14B—C21B—C22B	57.4 (4)
C16A—C7A—C8A—C13A	−27.2 (3)	C15B—C14B—C21B—C20B	−2.3 (4)
C17A—C7A—C8A—N9A	103.2 (3)	C15B—C14B—C21B—C22B	176.0 (3)
C17A—C7A—C8A—C13A	−139.7 (3)	C14B—C15B—C16B—N19B	62.8 (3)
C6A—C7A—C16A—N19A	154.8 (3)	C14B—C15B—C16B—C7B	−57.5 (3)
C6A—C7A—C16A—C15A	−81.6 (3)	C7B—C17B—C18B—N19B	36.3 (3)
C8A—C7A—C16A—N19A	−86.7 (3)	N19B—C20B—C21B—C14B	54.1 (4)
C16A—C7A—C17A—C18A	−41.2 (3)	N19B—C20B—C21B—C22B	−124.1 (3)
C7A—C8A—C13A—C12A	173.7 (2)	C14B—C21B—C22B—C23B	−0.7 (5)
N9A—C8A—C13A—C12A	−70.0 (3)	C20B—C21B—C22B—C23B	177.4 (3)
N9A—C8A—C13A—C14A	156.3 (2)	C21B—C22B—C23B—O24B	−65.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11W···O3W	0.93	1.86	2.785 (6)	170
O1W—H12W···O25A	0.87	2.11	2.960 (4)	168
O2W—H21W···O1W	0.91	1.90	2.815 (5)	175
O2W—H22W···N19B^i	0.77	2.02	2.781 (4)	170
O3W—H31W···O4W	0.81	2.00	2.785 (7)	164
O3W—H32W···O25A^i	0.89	1.90	2.794 (4)	179
O4W—H41W···O2W	0.73	2.13	2.843 (7)	164
O4W—H42W···O3W^i	0.73	2.55	3.210 (6)	151
C4A—H4A···O25A	0.95	2.39	2.930 (4)	115
C4B—H4B···O25B	0.95	2.43	2.923 (4)	112
C22A—H22A···O25B^ii	0.95	2.57	3.327 (4)	137
C26B—H30B···O24A^iii	0.98	2.56	3.107 (4)	115
C17A—H31A···O3A^iv	0.99	2.44	3.324 (4)	149
C20B—H35B···N19A^v	0.99	2.58	3.525 (4)	159
C15A—H38A···O3A^vi	0.99	2.44	3.164 (4)	129

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