Two pseudopolymorphic hydrates of brucine: brucine-water (1/4) and brucine-water (1/5.25) at 130 K

The structures of two pseudopolymorphic hydrates of brucine, C₂₃H₂₆N₂O₄·4H₂O, (I), and C₂₃H₂₆N₂O₄·5.25H₂O, (II), have been determined at 130 K. In both (I) and (II) (which has two independent brucine mol­ecules together with 10.5 water mol­ecules of solvation in the asymmetric unit), the brucine mol­ecules form head-to-tail sheet substructures, which associate with the water mol­ecules in the inter­stitial cavities through hydrogen-bonding associations and, together with water-water associations, give three-dimensional framework structures.

S1. Comment

The commercially available form of the alkaloid brucine is a tetrahydrate, this being first reported by Groth (1919). The crystal structure of the anhydrous form (m.p. 451 K), readily obtained from the hydrate by heating at 373 K (O'Neil, 2001), has been reported recently (Bialońska & Ciunik, 2004a). Although the crystal cell data for the orthorhombic tetrahydrate have been reported (Eeles, 1953), its structure has not previously been determined. Reported along with the anhydrous brucine structure were the structures of two brucine solvate pseudopolymorphs (Bernstein, 1987; Kumar et al., 1999), brucine acetone solvate and brucine 2-propanol solvate dihydrate (Bialońska & Ciunik, 2004a). This 2-propanol solvate structure is isomorphous with the previously reported brucine ethanol solvate dihydrate structure (Glover et al., 1985). Molecular recognition has been demonstrated as being significant in dictating the selectivity shown by brucine for various molecules, including the classic Fischer-type resolved N-benzoyl-protected alanine enantiomers (Fischer, 1899; Gould & Walkinshaw, 1984) and the compound with an achiral molecule, brucinium 3-nitrobenzoate (Oshikawa et al., 2002), where no crystalline products were obtained with the ortho- or para-substituted benzoic acid isomers. With the brucine compounds generally, the brucine species commonly form regular undulating parallel or antiparallel host sheet substructures built from partially overlapping head-to-tail molecular associations (Gould & Walkinshaw, 1984; Dijksma, Gould, Parsons, Taylor & Walkinshaw, 1998; Bialońska & Ciunik, 2004b). The compatible guest species then may occupy the interstitial cavities, associating with the host sheets through hydrogen-bonding interactions. Molecules of solvation (commonly water) act in either a proton-donor/acceptor or a space-filling capacity.

The tetrahydrate, (I), obtained as minor clusters of well formed prismatic needles from the attempted preparation of a brucine–adenosine adduct in 50% ethanol–water, was confirmed from the cell parameters and space group as being the orthorhombic tetrahydrate reported by Eeles (1953) (a = 7.6 Å, b = 11.6 Å, c = 26.6 Å, Z = 4, space group P2₁2₁2₁). The second pseudopolymorphic hydrate, brucine 5.25-hydrate, (II), was similarly obtained, but in good yield, in an attempted preparation of a brucine–urea adduct in 50% ethanol–water. Initial diffraction data for (II), obtained at room temperature on a conventional four-circle diffractometer, provided a structure having an asymmetric unit comprising two ordered brucine molecules and 11 water molecules of solvation with varying occupancies in a centred monoclinic cell. The occupancies varied from ca 0.3–0.9, indicating significant solvate lability, although negligible crystal decay was evident from the intensity-standards change (0.25%) during the data collection period. This lability has also been observed in a number of recently determined brucine structures (Gould et al., 2002; Bialońska et al., 2005; Smith, Wermuth, Healy et al., 2005; Smith, Wermuth & White, 2005). Low-temperature [130 (2) K] data were therefore re-collected for (II), and later for (I), using a CCD-detector-equipped diffractometer, effectively resolving the problem.

The atom-numbering scheme for (I) is shown in Fig. 1, while Fig. 3 shows the presence of two independent brucine molecules (A and B) and 11 water molecules of solvation (one with an occupancy of 0.5) in the molecular repeating unit of (II). In addition, one of the water molecules in (II) is disordered over two approximately equal close sites [O10W with occupancy factor 0.543 (17), and O11W with occupancy factor 0.457 (17)]. The atom numbering for the brucine species in both (I) and (II) follows the original Robinson convention (Holmes, 1952) and both have the overall Cahn–Ingold–Prelog absolute configuration for the neutral brucine molecule (Eliel, 1962) [C7(R), C8(S), C12(S), C13(R), C14(R), C16(S)]. As expected, the rigid brucine molecules show negligible conformational variation, including the methoxy substituent groups, which are invariably anti-related and lie essentially in the plane of the benzene ring.

The brucine molecules in (I) form into the previously described undulating sheet substructures, which extend through the crystal along the b cell direction (Fig. 2). These are generated by the 2₁ screw operation along the c axis giving antiparallel sheet propagation along b, with a dimeric repeat in that direction of 11.53 Å (the a cell dimension). This value is significantly shorter than the common repeat of ca 12.5 Å found in a number of brucine structures, e.g. brucinium N-benzoylalinate–water (1/4.5) (antiparallel, 12.42 Å) (Gould & Walkinshaw, 1984); brucinium D-glucuronate trihydrate (parallel, 12.66 Å) and brucinium D-galacturonate monohydrate (antiparallel, 12.37 Å) (Dijksma, Gould, Parsons & Walkinshaw, 1998); the two brucinium cyanohydrin complexes (both antiparallel, 12.39 and 12.52 Å; Pinkerton et al., 1993), brucine 2-propanol solvate dihydrate (antiparallel, 12.37 Å; Biolońska & Ciunik, 2004a); and brucine ethanol solvate dihydrate (antiparallel, 12.34 Å; Glover et al., 1985). This shortening of the repeat interval parallels a contraction of the angle α [ca 87 ° in (I) but typically greater than 100°] between the lines drawn down the centre of the indole rings of adjacent brucine molecules in the head-to-tail interactive sequence (see Fig. 2).

In (II), the brucine substructure generated by the two independent molecules in the asymmetric unit differs significantly from that seen in (I) (Fig. 4). However, if the B molecules alone are considered, these do form into similar undulating sheet structures, which extend along the b cell direction with an approximate 12.2 Å dimer repeat (Fig. 5). In both (I) and (II), the intersheet cavities generated accommodate the water molecules of solvation, the overall structures being characterized by extensive hydrogen-bonding interactions (Tables 1 and 2). These involve all available proton donors and acceptors in water–brucine [both N19 and O25 (carbonyl) acceptors] and water–water interactions. In addition, there are unusual (for brucine) water–O(cage ether) interactions in both structures, viz. O4W—H···O24ⁱⁱⁱ [symmetry code; (iii) x + 1, y, z {sym code iv in Table 2?}] in (I) and O10W—H···O24A^vi [symmetry code; (vi) −x + 1, y, −z + 1] in (II). Additionally, in (II), there are water–O(methoxy) interactions, viz. O7W—H···O2B,O3B (symmetrical three-centred) and O9W—H···O3A (linear), also unusual for brucine and its compounds. In both pseudopolymorphs, three-dimensional framework structures are generated.

In the structure of (II), the molecular asymmetric unit comprises two brucine molecules and 11 water molecules [one of which (O12W) has half-occupancy], together with the previously mentioned, approximately equal, partially occupying disordered molecules O10W [0.543 (17)] and O11W [0.457 (17)]. The observation with (II) that there was no apparent physical crystal deterioration during the room-temperature conventional diffractometer data collection period indicates the stability of the basic brucine substructure, which is retained with some variation in the structure of the anhydrous form (Bialońska & Ciunik, 2004a) (where there are no interstitial species, hence only intersheet interactions), resulting in a larger angle (ca 123 °) between adjacent brucine molecules in the parallel-mode substructure. This gives a longer dimer repeat (12.7 Å), and compares with ca 115° in the N-benzoylalinate salt, ca 110° in the 2-propanol hydrate structure and ca 113° for the B-molecule chains in (II).

S2. Experimental

Brucine tetrahydrate, (I), was obtained as isolated clusters of well formed colourless prismatic needles [m.p. 378 K (literature) (Moffat, 1986; Buckingham, 1982)] from the attempted preparation of a brucine–adenosine adduct in 50% ethanol–water, after partial room-temperature evaporation. Hydrate (II) was obtained from an attempted preparation of a brucine–urea adduct in 50% ethanol–water, as large colourless prismatic crystals (m.p. 386.9–388.2 K).

S3. Refinement

H atoms potentially involved in hydrogen-bonding interactions were generally located by difference methods. However, a number of the H atoms of the water molecules of (II) could not be located and were included in the refinement at calculated sites dictated by the assumed hydrogen-bonding geometry. Because of the low reflection/refined parameter ratio, all water H atoms were constrained in the refinement. Brucine H atoms were included at calculated positions [C—H(aromatic) = 0.95 Å; C—H(aliphatic) = 0.96–0.99 Å] and treated as riding, with U_iso(H) values of 1.2U_eq(C), or 1.5U_eq(C) for methyl atoms. The atom-numbering scheme for brucine (Figs. 1 and 3) follows the original Robinson convention used for strychnine (Holmes, 1952). The absolute configuration determined for the parent strychnine (Peerdeman, 1956) was invoked.

Computing details

For both compounds, data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 1999). Program(s) used to solve structure: SHELXTL?? (Bruker, 1997) and WinGX (Farrugia, 1999) for (I); SHELXS97 (Sheldrick, 1997) and WinGX (Farrugia, 1999) for (II). Program(s) used to refine structure: SHELXTL?? and WinGX for (I); SHELXL97 (Sheldrick, 1997) and WinGX for (II). For both compounds, 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 brucine molecule and the four water molecules in the molecular repeating unit in (I). Non-H atoms are shown as 40% probability displacement ellipsoids.
	Fig. 2. A perspective view of the packing of (I), viewed down the approximate a axial direction. The angle (α) between the lines through the centre of the indole rings in the brucine repeat unit is also shown. Hydrogen-bonding associations are shown as broken lines. [Symmetry codes: (v) x − 1, y, z.; (vi) −x + 1, y + 1/2; −z + 3/2. For other codes, see Table 1.]
	Fig. 3. The molecular configuration and atom-numbering scheme for the two independent brucine molecules (A and B) and the 11 water molecules in the molecular repeating unit in (II). Water molecule O12W has 50% occupancy, while molecules O10W and O11W represent disordered portions of another water molecule (occupancy factors both ca 1/2). Non-H atoms are shown as 30% probability displacement ellipsoids.
	Fig. 4. A perspective view of the partial packing of (II), viewed down the approximate c axial direction, showing brucine–water and water–water hydrogen-bonding interactions. [Symmetry code: (x) x + 1/2, −y − 1/2, z. For other codes, see Table 2.]
	Fig. 5. A similar view of the unit cell in (II), showing the brucine B-molecules only and their propagation down the b axial direction.

(I) 2,3-dimethoxystrychnidin-10-one–water (1/4)

Crystal data

C23H26N2O4·4H2O	Dx = 1.343 Mg m^−3
Mr = 466.52	Melting point: 378 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2584 reflections
a = 7.555 (2) Å	θ = 2.7–20.5°
b = 11.531 (3) Å	µ = 0.10 mm^−1
c = 26.492 (8) Å	T = 130 K
V = 2307.9 (11) Å^3	Plate, colourless
Z = 4	0.50 × 0.25 × 0.05 mm
F(000) = 1000

Data collection

Bruker CCD area-detector diffractometer	1727 reflections with F^2 > 2σ(F^2)
Radiation source: sealed tube	Rint = 0.066
Graphite monochromator	θmax = 25.0°, θmin = 1.9°
ϕ and ω scans	h = −8→8
11874 measured reflections	k = −12→13
2346 independent reflections	l = −31→30

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.084	w = 1/[σ^2(Fo^2) + (0.0319P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.89	(Δ/σ)max = 0.002
2346 reflections	Δρmax = 0.17 e Å^−3
301 parameters	Δρmin = −0.21 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0025 (4)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'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
O2	0.7477 (2)	0.30126 (13)	0.79247 (6)	0.0503 (6)
O3	0.7110 (2)	0.46433 (14)	0.85768 (6)	0.0530 (6)
O24	0.7409 (2)	0.96359 (14)	0.61067 (6)	0.0561 (7)
O25	0.7655 (3)	0.86338 (14)	0.78146 (6)	0.0645 (7)
N9	0.6837 (2)	0.74540 (16)	0.71731 (7)	0.0406 (7)
N19	0.6581 (3)	0.55296 (18)	0.56471 (7)	0.0461 (7)
C1	0.7115 (3)	0.43496 (19)	0.72192 (8)	0.0420 (8)
C2	0.7241 (3)	0.4104 (2)	0.77320 (8)	0.0413 (8)
C3	0.7103 (3)	0.4997 (2)	0.80812 (8)	0.0400 (8)
C4	0.6974 (3)	0.6137 (2)	0.79334 (8)	0.0423 (9)
C5	0.6930 (3)	0.6359 (2)	0.74165 (8)	0.0386 (8)
C6	0.6942 (3)	0.5489 (2)	0.70686 (8)	0.0386 (8)
C7	0.6600 (3)	0.5946 (2)	0.65435 (8)	0.0384 (8)
C8	0.6880 (3)	0.72724 (19)	0.66128 (8)	0.0382 (8)
C10	0.7422 (3)	0.8479 (2)	0.73614 (9)	0.0460 (9)
C11	0.7725 (4)	0.9429 (2)	0.69842 (9)	0.0550 (10)
C12	0.8507 (3)	0.9086 (2)	0.64756 (9)	0.0481 (9)
C13	0.8616 (3)	0.7780 (2)	0.64338 (8)	0.0399 (8)
C14	0.9271 (3)	0.7242 (2)	0.59389 (8)	0.0429 (9)
C15	0.9504 (3)	0.5948 (2)	0.60391 (9)	0.0465 (9)
C16	0.7700 (3)	0.5416 (2)	0.61134 (8)	0.0421 (8)
C17	0.4734 (3)	0.5677 (2)	0.63640 (8)	0.0450 (9)
C18	0.4814 (3)	0.5920 (2)	0.58021 (8)	0.0483 (9)
C20	0.7364 (4)	0.6311 (2)	0.52679 (8)	0.0550 (9)
C21	0.8017 (3)	0.7412 (2)	0.54957 (8)	0.0472 (9)
C22	0.7489 (4)	0.8441 (2)	0.53495 (9)	0.0554 (10)
C23	0.8046 (4)	0.9546 (2)	0.55952 (10)	0.0681 (11)
C25	0.7779 (4)	0.2107 (2)	0.75690 (10)	0.0583 (10)
C26	0.6924 (4)	0.5508 (2)	0.89554 (9)	0.0636 (10)
O1W	0.7698 (4)	0.8312 (2)	0.96851 (11)	0.0913 (11)
O2W	0.4091 (4)	0.8217 (2)	0.96011 (8)	0.0733 (10)
O3W	0.9264 (4)	0.8149 (2)	0.87513 (10)	0.0823 (11)
O4W	1.2627 (4)	0.7149 (2)	0.87513 (9)	0.0867 (10)
H1	0.714900	0.374300	0.697700	0.0500*
H4	0.691800	0.674800	0.817400	0.0510*
H8	0.589600	0.769300	0.645600	0.0460*
H11A	0.850400	0.999800	0.713700	0.0660*
H11B	0.660000	0.980900	0.692300	0.0660*
H12	0.970400	0.940700	0.645000	0.0580*
H13	0.948800	0.754600	0.668800	0.0480*
H14	1.042400	0.757800	0.585300	0.0520*
H15A	1.009600	0.558300	0.575600	0.0560*
H15B	1.022100	0.583100	0.633900	0.0560*
H16	0.785800	0.458800	0.618400	0.0510*
H17A	0.442900	0.487400	0.642900	0.0540*
H17B	0.387400	0.617500	0.652900	0.0540*
H18A	0.390100	0.549200	0.562400	0.0580*
H18B	0.466300	0.674100	0.573500	0.0580*
H20A	0.648200	0.648900	0.501300	0.0660*
H20B	0.834000	0.591800	0.510200	0.0660*
H22	0.670300	0.848600	0.507000	0.0660*
H23A	0.932800	0.959100	0.559600	0.0820*
H23B	0.759900	1.019500	0.540000	0.0820*
H25A	0.879500	0.229200	0.736700	0.0880*
H25B	0.676100	0.202600	0.735500	0.0880*
H25C	0.798500	0.139200	0.774500	0.0880*
H26A	0.585700	0.594000	0.889700	0.0950*
H26B	0.792200	0.602300	0.894400	0.0950*
H26C	0.686900	0.514600	0.928100	0.0950*
H11W	0.821	0.776	0.9867	0.108*
H12W	0.825	0.819	0.9381	0.108*
H21W	0.519	0.817	0.9610	0.088*
H22W	0.396	0.896	0.9541	0.088*
H31W	0.875	0.830	0.8450	0.098*
H32W	1.034	0.783	0.8750	0.098*
H41W	1.267	0.637	0.8764	0.103*
H42W	1.301	0.749	0.9018	0.103*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0672 (12)	0.0455 (10)	0.0383 (10)	0.0018 (9)	−0.0016 (9)	0.0047 (8)
O3	0.0680 (12)	0.0617 (11)	0.0293 (9)	0.0032 (9)	0.0022 (9)	0.0044 (8)
O24	0.0710 (13)	0.0496 (10)	0.0476 (11)	0.0050 (10)	−0.0022 (10)	0.0089 (8)
O25	0.0954 (15)	0.0593 (11)	0.0389 (11)	0.0046 (11)	−0.0102 (10)	−0.0111 (9)
N9	0.0505 (13)	0.0415 (12)	0.0299 (10)	0.0040 (10)	−0.0029 (9)	−0.0022 (9)
N19	0.0577 (14)	0.0523 (13)	0.0283 (11)	−0.0039 (11)	−0.0041 (10)	−0.0013 (10)
C1	0.0492 (15)	0.0445 (14)	0.0323 (13)	−0.0012 (12)	−0.0020 (12)	−0.0024 (11)
C2	0.0405 (15)	0.0453 (14)	0.0380 (14)	0.0008 (12)	−0.0011 (11)	0.0037 (12)
C3	0.0393 (15)	0.0546 (15)	0.0261 (12)	0.0021 (11)	0.0009 (11)	0.0039 (11)
C4	0.0484 (16)	0.0469 (15)	0.0315 (14)	0.0029 (11)	−0.0022 (11)	−0.0046 (11)
C5	0.0393 (14)	0.0441 (14)	0.0323 (14)	0.0032 (11)	−0.0010 (11)	0.0028 (11)
C6	0.0386 (14)	0.0483 (14)	0.0288 (13)	−0.0017 (12)	−0.0022 (11)	−0.0005 (11)
C7	0.0442 (15)	0.0428 (13)	0.0281 (13)	0.0009 (11)	−0.0007 (11)	0.0003 (11)
C8	0.0401 (14)	0.0474 (14)	0.0270 (12)	0.0011 (11)	−0.0052 (10)	−0.0006 (11)
C10	0.0517 (16)	0.0450 (15)	0.0414 (15)	0.0072 (13)	−0.0066 (12)	−0.0062 (12)
C11	0.0711 (19)	0.0414 (14)	0.0525 (17)	0.0029 (14)	−0.0010 (14)	−0.0016 (13)
C12	0.0507 (16)	0.0446 (15)	0.0490 (16)	−0.0018 (12)	−0.0062 (13)	0.0026 (13)
C13	0.0404 (14)	0.0453 (14)	0.0341 (14)	−0.0003 (11)	−0.0066 (11)	0.0023 (12)
C14	0.0402 (15)	0.0508 (16)	0.0378 (14)	−0.0036 (12)	0.0039 (11)	−0.0007 (12)
C15	0.0483 (16)	0.0572 (16)	0.0341 (14)	0.0048 (13)	−0.0011 (12)	−0.0066 (13)
C16	0.0510 (16)	0.0426 (13)	0.0328 (13)	0.0034 (13)	−0.0067 (12)	−0.0040 (11)
C17	0.0476 (16)	0.0534 (16)	0.0339 (14)	−0.0058 (12)	−0.0015 (11)	−0.0008 (12)
C18	0.0485 (18)	0.0613 (17)	0.0351 (14)	−0.0062 (13)	−0.0085 (12)	0.0005 (14)
C20	0.0645 (18)	0.0695 (17)	0.0309 (14)	−0.0109 (15)	−0.0017 (13)	0.0007 (13)
C21	0.0531 (16)	0.0580 (17)	0.0306 (13)	−0.0046 (14)	0.0011 (12)	0.0043 (12)
C22	0.0615 (19)	0.0668 (19)	0.0378 (15)	−0.0052 (15)	−0.0014 (13)	0.0107 (13)
C23	0.093 (2)	0.0628 (18)	0.0485 (17)	−0.0073 (18)	0.0048 (17)	0.0177 (15)
C25	0.076 (2)	0.0502 (15)	0.0486 (16)	0.0010 (15)	−0.0002 (15)	0.0000 (13)
C26	0.086 (2)	0.0751 (19)	0.0297 (14)	0.0098 (17)	0.0013 (14)	−0.0026 (14)
O1W	0.105 (2)	0.105 (2)	0.0638 (16)	0.0385 (16)	0.0042 (15)	0.0019 (14)
O2W	0.085 (2)	0.0634 (16)	0.0714 (16)	0.0016 (13)	−0.0037 (13)	0.0150 (11)
O3W	0.082 (2)	0.113 (2)	0.0520 (15)	−0.0097 (16)	−0.0094 (14)	0.0028 (14)
O4W	0.123 (2)	0.0616 (15)	0.0756 (16)	0.0151 (15)	−0.0245 (15)	−0.0026 (13)

Geometric parameters (Å, º)

O2—C2	1.370 (3)	C13—C14	1.533 (3)
O2—C25	1.425 (3)	C14—C15	1.526 (3)
O3—C3	1.375 (3)	C14—C21	1.521 (3)
O3—C26	1.421 (3)	C15—C16	1.508 (3)
O24—C12	1.430 (3)	C17—C18	1.516 (3)
O24—C23	1.442 (3)	C20—C21	1.490 (3)
O25—C10	1.227 (3)	C21—C22	1.310 (3)
O1W—H11W	0.89	C22—C23	1.491 (3)
O1W—H12W	0.92	C1—H1	0.9500
O2W—H21W	0.83	C4—H4	0.9500
O2W—H22W	0.88	C8—H8	0.9800
O3W—H31W	0.90	C11—H11B	0.9699
O3W—H32W	0.89	C11—H11A	0.9699
O4W—H41W	0.90	C12—H12	0.9795
O4W—H42W	0.86	C13—H13	0.9800
N9—C8	1.499 (3)	C14—H14	0.9802
N9—C10	1.357 (3)	C15—H15B	0.9710
N9—C5	1.420 (3)	C15—H15A	0.9694
N19—C16	1.503 (3)	C16—H16	0.9802
N19—C18	1.467 (3)	C17—H17A	0.9696
N19—C20	1.473 (3)	C17—H17B	0.9711
C1—C2	1.391 (3)	C18—H18A	0.9706
C1—C6	1.379 (3)	C18—H18B	0.9700
C2—C3	1.388 (3)	C20—H20A	0.9706
C3—C4	1.375 (3)	C20—H20B	0.9707
C4—C5	1.393 (3)	C22—H22	0.9501
C5—C6	1.362 (3)	C23—H23B	0.9703
C6—C7	1.510 (3)	C23—H23A	0.9699
C7—C8	1.555 (3)	C25—H25B	0.9600
C7—C16	1.537 (3)	C25—H25C	0.9599
C7—C17	1.520 (3)	C25—H25A	0.9597
C8—C13	1.512 (3)	C26—H26B	0.9602
C10—C11	1.500 (3)	C26—H26C	0.9592
C11—C12	1.523 (3)	C26—H26A	0.9602
C12—C13	1.512 (3)
C2—O2—C25	116.60 (17)	C2—C1—H1	121
C3—O3—C26	117.74 (18)	C3—C4—H4	121
C12—O24—C23	114.63 (18)	C5—C4—H4	121
H11W—O1W—H12W	100	C13—C8—H8	109.47
H21W—O2W—H22W	100	C7—C8—H8	109.48
H31W—O3W—H32W	118	N9—C8—H8	109.52
H41W—O4W—H42W	114	C10—C11—H11B	107.91
C5—N9—C8	108.93 (17)	C12—C11—H11A	108.02
C5—N9—C10	126.28 (19)	C10—C11—H11A	107.97
C8—N9—C10	118.59 (18)	C12—C11—H11B	108.02
C16—N19—C18	107.97 (17)	H11A—C11—H11B	107.21
C18—N19—C20	111.62 (19)	O24—C12—H12	108.70
C16—N19—C20	112.8 (2)	C13—C12—H12	108.72
C2—C1—C6	118.9 (2)	C11—C12—H12	108.73
O2—C2—C1	124.1 (2)	C8—C13—H13	105.13
O2—C2—C3	116.29 (19)	C12—C13—H13	105.10
C1—C2—C3	119.6 (2)	C14—C13—H13	105.03
C2—C3—C4	121.6 (2)	C21—C14—H14	108.86
O3—C3—C2	114.6 (2)	C13—C14—H14	109.00
O3—C3—C4	123.8 (2)	C15—C14—H14	108.93
C3—C4—C5	117.2 (2)	C14—C15—H15B	110.04
N9—C5—C4	127.7 (2)	C16—C15—H15A	109.97
N9—C5—C6	110.37 (19)	C16—C15—H15B	109.94
C4—C5—C6	122.0 (2)	C14—C15—H15A	110.07
C1—C6—C5	120.4 (2)	H15A—C15—H15B	108.38
C1—C6—C7	128.0 (2)	N19—C16—H16	108.08
C5—C6—C7	111.4 (2)	C7—C16—H16	108.16
C6—C7—C16	116.85 (19)	C15—C16—H16	108.13
C6—C7—C17	112.07 (18)	C7—C17—H17B	111.05
C6—C7—C8	102.20 (17)	C18—C17—H17A	111.12
C16—C7—C17	100.86 (17)	C7—C17—H17A	111.09
C8—C7—C16	113.90 (18)	H17A—C17—H17B	109.01
C8—C7—C17	111.34 (19)	C18—C17—H17B	111.06
C7—C8—C13	117.49 (19)	C17—C18—H18B	110.83
N9—C8—C13	105.97 (17)	C17—C18—H18A	110.80
N9—C8—C7	104.56 (17)	N19—C18—H18A	110.76
O25—C10—C11	121.6 (2)	H18A—C18—H18B	108.88
N9—C10—C11	116.2 (2)	N19—C18—H18B	110.80
O25—C10—N9	122.2 (2)	N19—C20—H20A	109.15
C10—C11—C12	117.3 (2)	N19—C20—H20B	109.16
O24—C12—C11	105.33 (18)	C21—C20—H20A	109.21
O24—C12—C13	115.03 (19)	C21—C20—H20B	109.25
C11—C12—C13	110.15 (19)	H20A—C20—H20B	107.77
C8—C13—C14	113.05 (18)	C23—C22—H22	118
C12—C13—C14	118.90 (19)	C21—C22—H22	118
C8—C13—C12	108.37 (18)	O24—C23—H23A	109.11
C15—C14—C21	109.40 (19)	O24—C23—H23B	109.22
C13—C14—C15	106.52 (18)	H23A—C23—H23B	107.91
C13—C14—C21	114.02 (19)	C22—C23—H23A	109.17
C14—C15—C16	108.44 (19)	C22—C23—H23B	109.15
N19—C16—C15	111.46 (18)	O2—C25—H25B	109.48
C7—C16—C15	115.08 (19)	O2—C25—H25C	109.52
N19—C16—C7	105.70 (18)	H25A—C25—H25B	109.46
C7—C17—C18	103.45 (18)	H25A—C25—H25C	109.40
N19—C18—C17	104.73 (18)	O2—C25—H25A	109.51
N19—C20—C21	112.20 (18)	H25B—C25—H25C	109.46
C14—C21—C20	114.15 (19)	H26A—C26—H26C	109.53
C20—C21—C22	123.4 (2)	H26B—C26—H26C	109.36
C14—C21—C22	122.3 (2)	H26A—C26—H26B	109.47
C21—C22—C23	124.0 (2)	O3—C26—H26A	109.47
O24—C23—C22	112.2 (2)	O3—C26—H26B	109.51
C6—C1—H1	121	O3—C26—H26C	109.49
C25—O2—C2—C1	6.3 (3)	C1—C6—C7—C8	−170.5 (2)
C25—O2—C2—C3	−174.5 (2)	C5—C6—C7—C16	139.7 (2)
C26—O3—C3—C2	−178.3 (2)	C8—C7—C16—C15	34.9 (3)
C26—O3—C3—C4	1.8 (3)	C6—C7—C8—C13	101.8 (2)
C23—O24—C12—C13	−66.0 (2)	C6—C7—C8—N9	−15.3 (2)
C23—O24—C12—C11	172.52 (19)	C17—C7—C16—N19	30.8 (2)
C12—O24—C23—C22	84.9 (3)	C6—C7—C16—C15	−84.0 (3)
C10—N9—C8—C13	41.1 (2)	C6—C7—C16—N19	152.51 (19)
C5—N9—C10—C11	160.9 (2)	C8—C7—C17—C18	80.1 (2)
C10—N9—C5—C6	−154.5 (2)	C16—C7—C17—C18	−41.1 (2)
C8—N9—C5—C6	−2.9 (2)	C17—C7—C16—C15	154.22 (19)
C10—N9—C8—C7	165.90 (18)	C17—C7—C8—C13	−138.34 (19)
C8—N9—C10—O25	−169.8 (2)	C16—C7—C8—C13	−25.1 (3)
C5—N9—C10—O25	−20.7 (3)	C6—C7—C17—C18	−166.13 (18)
C5—N9—C8—C13	−112.94 (19)	C17—C7—C8—N9	104.56 (19)
C5—N9—C8—C7	11.8 (2)	C8—C7—C16—N19	−88.6 (2)
C8—N9—C10—C11	11.7 (3)	C16—C7—C8—N9	−142.21 (18)
C10—N9—C5—C4	26.6 (3)	C7—C8—C13—C14	38.8 (3)
C8—N9—C5—C4	178.2 (2)	N9—C8—C13—C12	−70.8 (2)
C18—N19—C16—C15	−134.6 (2)	N9—C8—C13—C14	155.15 (18)
C20—N19—C16—C15	−10.7 (3)	C7—C8—C13—C12	172.83 (18)
C20—N19—C16—C7	115.0 (2)	O25—C10—C11—C12	143.4 (2)
C16—N19—C20—C21	−46.1 (3)	N9—C10—C11—C12	−38.2 (3)
C16—N19—C18—C17	−17.1 (2)	C10—C11—C12—C13	7.0 (3)
C20—N19—C18—C17	−141.62 (19)	C10—C11—C12—O24	131.6 (2)
C18—N19—C16—C7	−8.9 (2)	O24—C12—C13—C14	57.8 (3)
C18—N19—C20—C21	75.7 (3)	O24—C12—C13—C8	−73.1 (2)
C2—C1—C6—C7	−173.2 (2)	C11—C12—C13—C14	176.6 (2)
C6—C1—C2—C3	3.2 (3)	C11—C12—C13—C8	45.8 (2)
C6—C1—C2—O2	−177.7 (2)	C8—C13—C14—C15	−59.8 (2)
C2—C1—C6—C5	1.3 (3)	C12—C13—C14—C21	−67.8 (3)
C1—C2—C3—C4	−4.9 (3)	C12—C13—C14—C15	171.47 (19)
C1—C2—C3—O3	175.2 (2)	C8—C13—C14—C21	61.0 (3)
O2—C2—C3—C4	175.9 (2)	C13—C14—C15—C16	68.8 (2)
O2—C2—C3—O3	−4.0 (3)	C15—C14—C21—C20	−1.0 (3)
C2—C3—C4—C5	2.0 (3)	C13—C14—C21—C22	56.2 (3)
O3—C3—C4—C5	−178.1 (2)	C13—C14—C21—C20	−120.1 (2)
C3—C4—C5—C6	2.6 (3)	C21—C14—C15—C16	−54.9 (2)
C3—C4—C5—N9	−178.7 (2)	C15—C14—C21—C22	175.3 (2)
N9—C5—C6—C1	176.8 (2)	C14—C15—C16—N19	62.4 (2)
C4—C5—C6—C1	−4.2 (4)	C14—C15—C16—C7	−57.9 (2)
C4—C5—C6—C7	171.1 (2)	C7—C17—C18—N19	36.8 (2)
N9—C5—C6—C7	−7.9 (3)	N19—C20—C21—C22	−123.4 (3)
C5—C6—C7—C8	14.6 (2)	N19—C20—C21—C14	52.9 (3)
C5—C6—C7—C17	−104.7 (2)	C14—C21—C22—C23	0.1 (4)
C1—C6—C7—C16	−45.4 (3)	C20—C21—C22—C23	176.0 (2)
C1—C6—C7—C17	70.2 (3)	C21—C22—C23—O24	−65.2 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11W···O2W^i	0.89	1.92	2.791 (4)	166
O1W—H12W···O3W	0.92	1.84	2.749 (4)	172
O2W—H21W···O1W	0.83	1.91	2.736 (4)	170
O2W—H22W···N19^ii	0.88	1.92	2.793 (3)	173
O3W—H31W···O25	0.90	1.91	2.819 (4)	179
O3W—H32W···O4W	0.89	1.90	2.790 (4)	180
O4W—H41W···O24^iii	0.90	2.03	2.922 (3)	172
O4W—H42W···O2W^iv	0.86	1.94	2.794 (3)	175
C4—H4···O25	0.95	2.45	2.942 (3)	113
C12—H12···O3^v	0.98	2.42	3.376 (3)	164
C13—H13···O2^v	0.98	2.57	3.417 (3)	145
C23—H23B···O1W^vi	0.97	2.57	3.497 (4)	160

Symmetry codes: (i) x+1/2, −y+3/2, −z+2; (ii) −x+1, y+1/2, −z+3/2; (iii) −x+2, y−1/2, −z+3/2; (iv) x+1, y, z; (v) −x+2, y+1/2, −z+3/2; (vi) −x+3/2, −y+2, z−1/2.

(II) 2,3-dimethoxystrychnidin-10-one–water (1/5.25)

Crystal data

C23H26N2O4·5.25H2O	F(000) = 2100
Mr = 489.0	Dx = 1.352 Mg m^−3
Monoclinic, C2	Melting point = 386.9–388.2 K
Hall symbol: C 2y	Mo Kα radiation, λ = 0.71073 Å
a = 23.351 (5) Å	Cell parameters from 4189 reflections
b = 12.200 (3) Å	θ = 2.2–24.9°
c = 16.972 (4) Å	µ = 0.10 mm^−1
β = 96.202 (4)°	T = 130 K
V = 4806.7 (19) Å^3	Block, colourless
Z = 8	0.35 × 0.30 × 0.15 mm

Data collection

Bruker CCD area-detector diffractometer	3673 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.098
Graphite monochromator	θmax = 25.0°, θmin = 1.2°
ϕ and ω scans	h = −19→27
12710 measured reflections	k = −14→10
4461 independent reflections	l = −18→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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.173	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0961P)^2] where P = (Fo^2 + 2Fc^2)/3
4461 reflections	(Δ/σ)max < 0.001
621 parameters	Δρmax = 0.49 e Å^−3
1 restraint	Δρmin = −0.28 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	Occ. (<1)
O2A	0.66197 (11)	0.8034 (3)	0.66734 (18)	0.0293 (10)
O3A	0.69393 (11)	0.6156 (3)	0.61548 (18)	0.0303 (10)
O24A	0.34016 (12)	0.3818 (3)	0.6117 (2)	0.0419 (11)
O25A	0.53763 (12)	0.3316 (3)	0.59137 (18)	0.0284 (10)
N9A	0.49108 (13)	0.4934 (3)	0.5970 (2)	0.0218 (10)
N19A	0.37116 (14)	0.7752 (4)	0.6561 (2)	0.0300 (13)
C1A	0.56105 (16)	0.7481 (4)	0.6565 (2)	0.0222 (14)
C2A	0.61882 (16)	0.7276 (4)	0.6497 (2)	0.0250 (14)
C3A	0.63596 (17)	0.6260 (4)	0.6219 (2)	0.0244 (14)
C4A	0.59596 (16)	0.5420 (4)	0.6032 (2)	0.0246 (14)
C5A	0.53884 (17)	0.5645 (4)	0.6123 (2)	0.0219 (12)
C6A	0.52138 (16)	0.6649 (4)	0.6377 (2)	0.0200 (13)
C7A	0.45627 (17)	0.6728 (4)	0.6289 (2)	0.0229 (14)
C8A	0.43812 (16)	0.5516 (4)	0.6166 (2)	0.0231 (14)
C10A	0.49262 (17)	0.3835 (4)	0.5966 (2)	0.0232 (14)
C11A	0.43610 (18)	0.3265 (4)	0.6010 (3)	0.0320 (16)
C12A	0.39531 (19)	0.3776 (4)	0.6568 (3)	0.0333 (16)
C13A	0.41828 (17)	0.4894 (4)	0.6868 (2)	0.0264 (14)
C14A	0.38127 (18)	0.5605 (4)	0.7361 (3)	0.0321 (14)
C15A	0.41861 (19)	0.6590 (5)	0.7659 (3)	0.0340 (14)
C16A	0.42779 (17)	0.7322 (4)	0.6959 (2)	0.0257 (14)
C17A	0.43385 (16)	0.7438 (4)	0.5574 (2)	0.0241 (14)
C18A	0.37043 (17)	0.7579 (4)	0.5700 (3)	0.0280 (14)
C20A	0.32041 (18)	0.7253 (5)	0.6867 (3)	0.0362 (16)
C21A	0.32541 (18)	0.6017 (5)	0.6918 (3)	0.0339 (16)
C22A	0.2858 (2)	0.5352 (5)	0.6558 (3)	0.0430 (18)
C23A	0.2931 (2)	0.4139 (6)	0.6555 (4)	0.058 (2)
C25A	0.6442 (2)	0.9088 (4)	0.6926 (3)	0.0371 (16)
C35A	0.71252 (18)	0.5163 (5)	0.5822 (3)	0.0394 (16)
O2B	0.28224 (12)	0.3245 (3)	0.89254 (19)	0.0308 (10)
O3B	0.37311 (11)	0.4351 (3)	0.93204 (18)	0.0311 (10)
O24B	0.16629 (12)	1.0279 (2)	0.87679 (17)	0.0253 (9)
O25B	0.34302 (12)	0.8480 (3)	0.9298 (2)	0.0392 (11)
N9B	0.25425 (13)	0.7727 (3)	0.9201 (2)	0.0218 (10)
N19B	0.06358 (15)	0.6815 (3)	0.8528 (2)	0.0309 (11)
C1B	0.22109 (17)	0.4869 (4)	0.8879 (2)	0.0232 (12)
C2B	0.27380 (17)	0.4349 (4)	0.8994 (2)	0.0237 (12)
C3B	0.32370 (17)	0.4970 (4)	0.9218 (2)	0.0233 (12)
C4B	0.32186 (17)	0.6091 (4)	0.9309 (2)	0.0246 (12)
C5B	0.26790 (17)	0.6594 (4)	0.9174 (2)	0.0211 (11)
C6B	0.21859 (16)	0.5993 (4)	0.8960 (2)	0.0216 (12)
C7B	0.16561 (18)	0.6706 (4)	0.8930 (2)	0.0230 (12)
C8B	0.19119 (16)	0.7878 (4)	0.8950 (2)	0.0213 (11)
C10B	0.29032 (18)	0.8585 (4)	0.9155 (3)	0.0268 (14)
C11B	0.26285 (18)	0.9668 (4)	0.8935 (3)	0.0272 (12)
C12B	0.20644 (17)	0.9685 (4)	0.8364 (3)	0.0241 (12)
C13B	0.18793 (16)	0.8504 (4)	0.8161 (2)	0.0225 (12)
C14B	0.13126 (17)	0.8308 (4)	0.7637 (3)	0.0264 (14)
C15B	0.12846 (18)	0.7087 (4)	0.7473 (2)	0.0263 (14)
C16B	0.11913 (17)	0.6488 (4)	0.8232 (3)	0.0255 (12)
C17B	0.13219 (17)	0.6512 (4)	0.9639 (3)	0.0256 (12)
C18B	0.07485 (18)	0.7062 (4)	0.9384 (3)	0.0320 (14)
C20B	0.03512 (18)	0.7742 (4)	0.8083 (3)	0.0323 (16)
C21B	0.07687 (18)	0.8666 (4)	0.8006 (3)	0.0278 (14)
C22B	0.06973 (18)	0.9670 (4)	0.8277 (3)	0.0279 (14)
C23B	0.11398 (19)	1.0560 (4)	0.8286 (3)	0.0314 (14)
C25B	0.2321 (2)	0.2600 (4)	0.8713 (3)	0.0374 (16)
C35B	0.42553 (17)	0.4914 (4)	0.9559 (3)	0.0325 (14)
O1W	0.6484 (2)	0.0550 (4)	0.5114 (4)	0.0613 (19)
O2W	0.49287 (19)	0.9980 (4)	0.6762 (3)	0.0571 (16)
O3W	0.4147 (2)	1.0180 (5)	0.8868 (4)	0.097 (2)
O4W	0.37374 (16)	0.9997 (4)	0.6499 (3)	0.0527 (16)
O5W	0.0821 (3)	0.3143 (6)	0.9213 (4)	0.110 (3)
O6W	0.54313 (14)	0.1107 (3)	0.5622 (2)	0.0380 (11)
O7W	0.38624 (17)	0.2253 (4)	0.8330 (3)	0.0563 (16)
O8W	0.01780 (14)	0.4773 (3)	0.8362 (2)	0.0461 (11)
O9W	0.80135 (19)	0.6254 (5)	0.7281 (3)	0.0723 (19)
O10W	0.7225 (4)	0.2403 (8)	0.4861 (7)	0.058 (4)	0.543 (17)
O11W	0.6978 (4)	0.2595 (8)	0.5432 (6)	0.071 (4)	0.457 (17)
O12W	0.5000 (9)	0.6918 (8)	0.9719 (9)	0.083 (7)	0.500
H1A	0.54890	0.81770	0.67360	0.0270*
H4A	0.60740	0.47260	0.58500	0.0290*
H8A	0.40770	0.54630	0.57040	0.0280*
H11A	0.44420	0.24990	0.61800	0.0380*
H11B	0.41550	0.32380	0.54690	0.0380*
H12A	0.39310	0.32780	0.70320	0.0400*
H13A	0.45420	0.47310	0.72250	0.0320*
H14A	0.37180	0.51700	0.78300	0.0380*
H15A	0.39920	0.70080	0.80540	0.0410*
H15B	0.45620	0.63310	0.79180	0.0410*
H16A	0.45250	0.79570	0.71530	0.0310*
H17A	0.45400	0.81530	0.55820	0.0290*
H17B	0.43820	0.70610	0.50670	0.0290*
H18A	0.35340	0.82180	0.54010	0.0330*
H18B	0.34800	0.69150	0.55290	0.0330*
H20A	0.31630	0.75530	0.74000	0.0430*
H20B	0.28540	0.74500	0.65140	0.0430*
H22A	0.25170	0.56600	0.62930	0.0520*
H23A	0.30050	0.38720	0.71070	0.0690*
H23B	0.25700	0.37950	0.63130	0.0690*
H25D	0.62400	0.90050	0.74000	0.0550*
H25E	0.61840	0.94270	0.65020	0.0550*
H25F	0.67820	0.95550	0.70510	0.0550*
H35A	0.69090	0.50450	0.53020	0.0590*
H35B	0.70570	0.45490	0.61730	0.0590*
H35C	0.75370	0.52120	0.57630	0.0590*
H1B	0.18690	0.44580	0.87450	0.0280*
H4B	0.35580	0.65040	0.94570	0.0290*
H8B	0.17360	0.83300	0.93530	0.0250*
H11C	0.29160	1.01200	0.86950	0.0320*
H11D	0.25500	1.00370	0.94320	0.0320*
H12B	0.21320	1.00830	0.78670	0.0290*
H13B	0.21890	0.81880	0.78660	0.0270*
H14B	0.13260	0.87050	0.71240	0.0320*
H15C	0.09640	0.69260	0.70590	0.0320*
H15D	0.16480	0.68390	0.72800	0.0320*
H16B	0.11790	0.56830	0.81210	0.0310*
H17C	0.15170	0.68550	1.01250	0.0300*
H17D	0.12720	0.57190	0.97350	0.0300*
H18C	0.04410	0.67580	0.96780	0.0380*
H18D	0.07740	0.78630	0.94750	0.0380*
H20C	0.00260	0.80070	0.83610	0.0390*
H20D	0.01940	0.74900	0.75490	0.0390*
H22B	0.03430	0.98360	0.84790	0.0340*
H23C	0.12270	1.07020	0.77380	0.0380*
H23D	0.09810	1.12420	0.84920	0.0380*
H25A	0.21490	0.28070	0.81820	0.0560*
H25B	0.20410	0.27280	0.90950	0.0560*
H25C	0.24260	0.18230	0.87180	0.0560*
H35D	0.42230	0.52990	1.00590	0.0490*
H35E	0.43310	0.54460	0.91500	0.0490*
H35F	0.45730	0.43860	0.96320	0.0490*
H11W	0.641	0.038	0.459	0.073*
H12W	0.622	0.050	0.528	0.073*
H21W	0.509	1.035	0.639	0.068*
H22W	0.459	1.007	0.660	0.068*
H31W	0.450	1.004	0.870	0.116*
H32W	0.392	0.964	0.901	0.116*
H41W	0.350	1.041	0.676	0.064*
H42W	0.363	0.927	0.652	0.064*
H51W	0.101	0.349	0.960	0.130*
H52W	0.061	0.367	0.894	0.130*
H61W	0.542	0.189	0.570	0.046*
H62W	0.544	0.102	0.514	0.046*
H71W	0.372	0.270	0.871	0.067*
H72W	0.396	0.157	0.851	0.067*
H81W	0.033	0.545	0.842	0.055*
H82W	0.009	0.484	0.783	0.055*
H91W	0.77200	0.64200	0.69400	0.086*
H92W	0.82800	0.68000	0.75000	0.086*
H13W	0.70000	0.18300	0.49400	0.070*	0.543
H14W	0.70200	0.28700	0.45300	0.070*	0.543
H15W	0.68200	0.19400	0.53300	0.085*	0.457
H16W	0.68700	0.29500	0.49900	0.085*	0.457
H17W	0.52800	0.73300	0.95500	0.096*	0.500
H18W	0.47700	0.72700	1.00200	0.096*	0.500

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2A	0.0193 (14)	0.0266 (19)	0.0417 (18)	−0.0061 (13)	0.0016 (12)	−0.0080 (14)
O3A	0.0127 (13)	0.036 (2)	0.0422 (18)	0.0003 (13)	0.0036 (12)	−0.0040 (15)
O24A	0.0160 (15)	0.042 (2)	0.067 (2)	−0.0100 (14)	0.0020 (15)	0.0060 (18)
O25A	0.0236 (15)	0.0228 (18)	0.0382 (17)	−0.0004 (13)	0.0008 (12)	0.0003 (14)
N9A	0.0142 (16)	0.022 (2)	0.0296 (18)	−0.0008 (14)	0.0046 (13)	0.0006 (16)
N19A	0.0198 (17)	0.036 (3)	0.035 (2)	0.0072 (16)	0.0066 (15)	−0.0017 (18)
C1A	0.0186 (19)	0.025 (3)	0.023 (2)	−0.0014 (17)	0.0022 (15)	−0.0028 (18)
C2A	0.019 (2)	0.030 (3)	0.025 (2)	−0.0044 (18)	−0.0015 (16)	−0.0029 (19)
C3A	0.019 (2)	0.029 (3)	0.026 (2)	−0.0025 (18)	0.0056 (16)	0.0000 (18)
C4A	0.021 (2)	0.027 (3)	0.026 (2)	0.0007 (18)	0.0035 (16)	−0.0038 (18)
C5A	0.021 (2)	0.024 (2)	0.020 (2)	−0.0008 (17)	−0.0015 (15)	0.0007 (18)
C6A	0.0140 (19)	0.026 (3)	0.0206 (19)	0.0005 (17)	0.0053 (15)	0.0002 (18)
C7A	0.020 (2)	0.025 (3)	0.024 (2)	0.0013 (17)	0.0039 (16)	0.0001 (18)
C8A	0.017 (2)	0.024 (3)	0.028 (2)	0.0050 (18)	0.0008 (16)	0.0033 (19)
C10A	0.022 (2)	0.023 (3)	0.024 (2)	0.0013 (19)	0.0004 (16)	0.0028 (18)
C11A	0.026 (2)	0.028 (3)	0.041 (3)	−0.010 (2)	−0.0002 (19)	0.008 (2)
C12A	0.028 (2)	0.030 (3)	0.042 (3)	−0.001 (2)	0.004 (2)	0.012 (2)
C13A	0.020 (2)	0.031 (3)	0.028 (2)	0.0027 (19)	0.0011 (16)	0.008 (2)
C14A	0.026 (2)	0.037 (3)	0.035 (2)	0.000 (2)	0.0114 (18)	0.005 (2)
C15A	0.027 (2)	0.048 (3)	0.028 (2)	0.006 (2)	0.0078 (18)	0.000 (2)
C16A	0.019 (2)	0.029 (3)	0.029 (2)	0.0035 (18)	0.0021 (16)	−0.0034 (19)
C17A	0.023 (2)	0.022 (3)	0.027 (2)	−0.0001 (18)	0.0018 (16)	−0.0026 (19)
C18A	0.021 (2)	0.029 (3)	0.033 (2)	0.0010 (19)	−0.0017 (17)	0.006 (2)
C20A	0.018 (2)	0.051 (3)	0.041 (3)	0.008 (2)	0.0102 (18)	0.007 (2)
C21A	0.020 (2)	0.046 (3)	0.038 (3)	0.001 (2)	0.0136 (19)	0.005 (2)
C22A	0.020 (2)	0.055 (4)	0.056 (3)	0.004 (2)	0.013 (2)	0.014 (3)
C23A	0.029 (3)	0.059 (4)	0.088 (4)	−0.008 (3)	0.017 (3)	0.016 (4)
C25A	0.028 (2)	0.032 (3)	0.052 (3)	−0.008 (2)	0.007 (2)	−0.010 (2)
C35A	0.019 (2)	0.043 (3)	0.057 (3)	0.000 (2)	0.008 (2)	−0.012 (3)
O2B	0.0258 (15)	0.0138 (17)	0.0512 (19)	0.0018 (13)	−0.0026 (13)	−0.0030 (14)
O3B	0.0189 (14)	0.032 (2)	0.0416 (18)	0.0053 (14)	−0.0006 (12)	0.0015 (15)
O24B	0.0262 (15)	0.0183 (17)	0.0307 (16)	0.0044 (12)	0.0006 (12)	−0.0027 (13)
O25B	0.0207 (16)	0.025 (2)	0.070 (2)	−0.0024 (14)	−0.0041 (15)	0.0084 (17)
N9B	0.0179 (16)	0.019 (2)	0.0273 (18)	0.0009 (14)	−0.0028 (13)	0.0015 (15)
N19B	0.0224 (18)	0.032 (2)	0.038 (2)	0.0007 (16)	0.0013 (15)	−0.0009 (18)
C1B	0.021 (2)	0.023 (2)	0.025 (2)	−0.0009 (17)	−0.0003 (16)	−0.0001 (18)
C2B	0.026 (2)	0.016 (2)	0.028 (2)	0.0018 (18)	−0.0016 (17)	0.0007 (18)
C3B	0.026 (2)	0.017 (2)	0.026 (2)	0.0047 (18)	−0.0009 (16)	0.0041 (18)
C4B	0.022 (2)	0.024 (2)	0.027 (2)	−0.0034 (18)	−0.0008 (16)	0.0038 (19)
C5B	0.023 (2)	0.019 (2)	0.0214 (19)	0.0002 (17)	0.0026 (16)	0.0001 (17)
C6B	0.018 (2)	0.021 (2)	0.026 (2)	−0.0017 (17)	0.0030 (16)	0.0005 (18)
C7B	0.024 (2)	0.015 (2)	0.030 (2)	0.0012 (17)	0.0028 (17)	0.0006 (18)
C8B	0.0154 (18)	0.019 (2)	0.029 (2)	0.0015 (16)	−0.0003 (16)	−0.0022 (17)
C10B	0.027 (2)	0.022 (3)	0.031 (2)	−0.0057 (19)	0.0012 (18)	0.0042 (19)
C11B	0.029 (2)	0.018 (2)	0.034 (2)	−0.0018 (18)	0.0008 (18)	0.0003 (19)
C12B	0.025 (2)	0.016 (2)	0.032 (2)	0.0005 (17)	0.0064 (17)	0.0037 (18)
C13B	0.021 (2)	0.022 (2)	0.025 (2)	0.0030 (17)	0.0043 (16)	0.0043 (18)
C14B	0.025 (2)	0.024 (3)	0.030 (2)	0.0029 (18)	0.0017 (17)	0.0028 (19)
C15B	0.022 (2)	0.031 (3)	0.025 (2)	0.0041 (18)	−0.0020 (16)	−0.0048 (19)
C16B	0.021 (2)	0.019 (2)	0.036 (2)	0.0008 (17)	0.0005 (17)	−0.0077 (19)
C17B	0.025 (2)	0.016 (2)	0.036 (2)	−0.0032 (18)	0.0048 (18)	−0.0013 (19)
C18B	0.026 (2)	0.031 (3)	0.040 (2)	0.003 (2)	0.0078 (19)	0.001 (2)
C20B	0.020 (2)	0.030 (3)	0.045 (3)	0.0027 (19)	−0.0054 (19)	−0.005 (2)
C21B	0.024 (2)	0.031 (3)	0.027 (2)	0.0025 (19)	−0.0035 (17)	0.0003 (19)
C22B	0.023 (2)	0.028 (3)	0.032 (2)	0.0074 (19)	−0.0008 (17)	0.001 (2)
C23B	0.035 (2)	0.024 (3)	0.034 (2)	0.007 (2)	−0.0017 (19)	−0.001 (2)
C25B	0.034 (2)	0.019 (3)	0.056 (3)	0.000 (2)	−0.010 (2)	−0.004 (2)
C35B	0.022 (2)	0.038 (3)	0.037 (2)	0.002 (2)	0.0005 (18)	0.007 (2)
O11W	0.080 (7)	0.055 (6)	0.071 (7)	−0.041 (5)	−0.021 (6)	0.011 (5)
O10W	0.057 (6)	0.043 (6)	0.070 (9)	0.023 (4)	−0.010 (5)	0.007 (5)
O1W	0.043 (3)	0.050 (3)	0.090 (4)	0.003 (2)	0.003 (2)	−0.010 (3)
O2W	0.038 (2)	0.065 (3)	0.068 (3)	−0.005 (2)	0.005 (2)	0.014 (2)
O3W	0.074 (3)	0.055 (3)	0.175 (6)	0.006 (3)	0.071 (3)	0.022 (4)
O4W	0.042 (2)	0.041 (3)	0.076 (3)	0.0009 (18)	0.0102 (19)	−0.002 (2)
O5W	0.115 (5)	0.078 (5)	0.122 (5)	0.044 (4)	−0.052 (4)	−0.045 (4)
O6W	0.0409 (19)	0.026 (2)	0.045 (2)	0.0034 (16)	−0.0045 (15)	−0.0007 (17)
O7W	0.066 (3)	0.049 (3)	0.058 (2)	0.012 (2)	0.025 (2)	−0.002 (2)
O8W	0.0348 (18)	0.037 (2)	0.067 (2)	−0.0065 (16)	0.0075 (16)	0.0001 (19)
O9W	0.065 (3)	0.075 (4)	0.077 (3)	0.013 (2)	0.008 (2)	−0.007 (3)
O12W	0.092 (6)	0.040 (5)	0.12 (1)	−0.025 (7)	−0.071 (14)	0.004 (7)

Geometric parameters (Å, º)

O2A—C2A	1.377 (5)	C12A—H12A	1.0000
O2A—C25A	1.431 (6)	C13A—H13A	1.0000
O3A—C3A	1.376 (5)	C14A—H14A	1.0000
O3A—C35A	1.424 (7)	C15A—H15A	0.9900
O24A—C12A	1.426 (6)	C15A—H15B	0.9900
O24A—C23A	1.446 (6)	C16A—H16A	1.0000
O25A—C10A	1.238 (5)	C17A—H17A	0.9900
O2B—C2B	1.368 (6)	C17A—H17B	0.9900
O2B—C25B	1.424 (6)	C18A—H18A	0.9900
O3B—C3B	1.374 (5)	C18A—H18B	0.9900
O3B—C35B	1.424 (5)	C20A—H20B	0.9900
O24B—C23B	1.436 (5)	C20A—H20A	0.9900
O24B—C12B	1.419 (5)	C22A—H22A	0.9500
O25B—C10B	1.235 (5)	C23A—H23B	0.9900
O10W—H13W	0.89	C23A—H23A	0.9900
O10W—H14W	0.90	C25A—H25D	0.9800
O11W—H16W	0.88	C25A—H25E	0.9800
O11W—H15W	0.89	C25A—H25F	0.9800
O1W—H11W	0.91	C35A—H35A	0.9800
O1W—H12W	0.71	C35A—H35B	0.9800
O2W—H22W	0.82	C35A—H35C	0.9800
O2W—H21W	0.89	C1B—C6B	1.380 (7)
N9A—C10A	1.341 (6)	C1B—C2B	1.380 (6)
N9A—C8A	1.494 (5)	C2B—C3B	1.407 (6)
N9A—C5A	1.415 (5)	C3B—C4B	1.378 (7)
N19A—C16A	1.512 (5)	C4B—C5B	1.398 (6)
N19A—C20A	1.476 (6)	C5B—C6B	1.380 (6)
N19A—C18A	1.475 (6)	C6B—C7B	1.509 (6)
O3W—H31W	0.92	C7B—C16B	1.541 (6)
O3W—H32W	0.90	C7B—C17B	1.522 (6)
N9B—C10B	1.351 (6)	C7B—C8B	1.549 (7)
N9B—C8B	1.499 (5)	C8B—C13B	1.536 (5)
N9B—C5B	1.420 (6)	C10B—C11B	1.498 (7)
N19B—C16B	1.495 (5)	C11B—C12B	1.549 (6)
N19B—C18B	1.479 (6)	C12B—C13B	1.533 (7)
N19B—C20B	1.477 (6)	C13B—C14B	1.531 (6)
O4W—H41W	0.90	C14B—C15B	1.516 (7)
O4W—H42W	0.92	C14B—C21B	1.539 (6)
O5W—H52W	0.90	C15B—C16B	1.517 (6)
O5W—H51W	0.86	C17B—C18B	1.518 (6)
O6W—H61W	0.97	C20B—C21B	1.505 (7)
O6W—H62W	0.83	C21B—C22B	1.325 (7)
O7W—H72W	0.91	C22B—C23B	1.498 (7)
O7W—H71W	0.93	C1B—H1B	0.9500
C1A—C2A	1.389 (5)	C4B—H4B	0.9500
C1A—C6A	1.388 (6)	C8B—H8B	1.0000
C2A—C3A	1.400 (7)	O9W—H91W	0.87
C3A—C4A	1.400 (6)	O9W—H92W	0.96
C4A—C5A	1.387 (6)	C11B—H11D	0.9900
C5A—C6A	1.375 (7)	C11B—H11C	0.9900
C6A—C7A	1.515 (5)	C12B—H12B	1.0000
C7A—C17A	1.536 (6)	C13B—H13B	1.0000
C7A—C8A	1.546 (7)	C14B—H14B	1.0000
C7A—C16A	1.557 (6)	C15B—H15D	0.9900
C8A—C13A	1.526 (5)	C15B—H15C	0.9900
C10A—C11A	1.501 (6)	C16B—H16B	1.0000
C11A—C12A	1.545 (7)	C17B—H17C	0.9900
C12A—C13A	1.532 (7)	C17B—H17D	0.9900
C13A—C14A	1.535 (6)	C18B—H18D	0.9900
C14A—C15A	1.538 (7)	C18B—H18C	0.9900
C14A—C21A	1.519 (7)	C20B—H20C	0.9900
C15A—C16A	1.520 (7)	C20B—H20D	0.9900
C17A—C18A	1.529 (6)	C22B—H22B	0.9500
C20A—C21A	1.514 (9)	C23B—H23C	0.9900
C21A—C22A	1.329 (7)	C23B—H23D	0.9900
C22A—C23A	1.490 (10)	C25B—H25B	0.9800
C1A—H1A	0.9500	C25B—H25A	0.9800
C4A—H4A	0.9500	C25B—H25C	0.9800
C8A—H8A	1.0000	C35B—H35F	0.9800
O8W—H82W	0.91	C35B—H35D	0.9800
O8W—H81W	0.90	C35B—H35E	0.9800
C11A—H11A	0.9900	O12W—H17W	0.90
C11A—H11B	0.9900	O12W—H18W	0.89
C2A—O2A—C25A	116.1 (3)	C22A—C23A—H23B	109.00
C3A—O3A—C35A	117.0 (3)	H25D—C25A—H25E	110.00
C12A—O24A—C23A	115.2 (4)	H25D—C25A—H25F	109.00
C2B—O2B—C25B	116.3 (3)	O2A—C25A—H25F	109.00
C3B—O3B—C35B	117.1 (4)	O2A—C25A—H25E	110.00
C12B—O24B—C23B	114.4 (3)	H25E—C25A—H25F	109.00
H13W—O10W—H14W	108	O2A—C25A—H25D	109.00
H15W—O11W—H16W	102	H35B—C35A—H35C	110.00
H11W—O1W—H12W	107	O3A—C35A—H35B	109.00
H21W—O2W—H22W	99	O3A—C35A—H35C	109.00
C5A—N9A—C8A	108.8 (3)	H35A—C35A—H35C	109.00
C5A—N9A—C10A	126.4 (3)	O3A—C35A—H35A	109.00
C8A—N9A—C10A	120.0 (3)	H35A—C35A—H35B	109.00
C16A—N19A—C20A	113.4 (4)	C2B—C1B—C6B	119.3 (4)
C18A—N19A—C20A	111.5 (4)	O2B—C2B—C1B	125.1 (4)
C16A—N19A—C18A	108.0 (3)	C1B—C2B—C3B	119.4 (4)
H31W—O3W—H32W	122	O2B—C2B—C3B	115.5 (4)
C8B—N9B—C10B	119.2 (4)	O3B—C3B—C2B	113.4 (4)
C5B—N9B—C10B	127.5 (3)	O3B—C3B—C4B	124.6 (4)
C5B—N9B—C8B	109.1 (3)	C2B—C3B—C4B	122.0 (4)
C16B—N19B—C18B	108.4 (3)	C3B—C4B—C5B	117.1 (4)
C16B—N19B—C20B	113.0 (3)	N9B—C5B—C4B	128.6 (4)
C18B—N19B—C20B	111.6 (4)	C4B—C5B—C6B	121.4 (4)
H41W—O4W—H42W	110	N9B—C5B—C6B	110.0 (4)
H51W—O5W—H52W	105	C1B—C6B—C7B	127.8 (4)
H61W—O6W—H62W	105	C5B—C6B—C7B	111.1 (4)
H71W—O7W—H72W	114	C1B—C6B—C5B	120.7 (4)
C2A—C1A—C6A	118.6 (4)	C6B—C7B—C17B	111.9 (3)
O2A—C2A—C1A	123.8 (4)	C6B—C7B—C8B	102.6 (3)
C1A—C2A—C3A	120.2 (4)	C6B—C7B—C16B	115.7 (3)
O2A—C2A—C3A	116.0 (3)	C8B—C7B—C16B	114.5 (3)
C2A—C3A—C4A	121.1 (4)	C8B—C7B—C17B	110.8 (3)
O3A—C3A—C2A	115.3 (4)	C16B—C7B—C17B	101.7 (3)
O3A—C3A—C4A	123.6 (4)	N9B—C8B—C7B	104.9 (3)
C3A—C4A—C5A	117.1 (4)	N9B—C8B—C13B	105.3 (3)
N9A—C5A—C4A	127.4 (4)	C7B—C8B—C13B	117.2 (3)
N9A—C5A—C6A	110.4 (3)	O25B—C10B—N9B	121.5 (4)
C4A—C5A—C6A	122.2 (4)	N9B—C10B—C11B	116.4 (4)
C1A—C6A—C5A	120.7 (4)	O25B—C10B—C11B	122.1 (4)
C5A—C6A—C7A	110.8 (4)	C10B—C11B—C12B	118.7 (4)
C1A—C6A—C7A	127.9 (4)	O24B—C12B—C13B	113.8 (3)
C6A—C7A—C8A	102.1 (4)	C11B—C12B—C13B	109.2 (4)
C6A—C7A—C16A	117.5 (3)	O24B—C12B—C11B	105.4 (4)
C8A—C7A—C16A	114.3 (3)	C12B—C13B—C14B	118.8 (4)
C8A—C7A—C17A	111.6 (3)	C8B—C13B—C12B	106.6 (3)
C6A—C7A—C17A	111.5 (3)	C8B—C13B—C14B	112.8 (3)
C16A—C7A—C17A	100.3 (3)	C13B—C14B—C21B	114.8 (4)
N9A—C8A—C13A	105.4 (3)	C15B—C14B—C21B	109.4 (4)
C7A—C8A—C13A	118.2 (3)	C13B—C14B—C15B	106.1 (4)
N9A—C8A—C7A	105.3 (3)	C14B—C15B—C16B	109.0 (4)
O25A—C10A—N9A	122.3 (4)	N19B—C16B—C15B	111.5 (4)
O25A—C10A—C11A	121.6 (4)	C7B—C16B—C15B	114.6 (4)
N9A—C10A—C11A	116.0 (4)	N19B—C16B—C7B	105.1 (4)
C10A—C11A—C12A	116.6 (4)	C7B—C17B—C18B	102.6 (4)
O24A—C12A—C13A	114.2 (4)	N19B—C18B—C17B	104.4 (4)
C11A—C12A—C13A	110.2 (4)	N19B—C20B—C21B	111.0 (4)
O24A—C12A—C11A	105.4 (4)	C14B—C21B—C22B	123.0 (4)
C12A—C13A—C14A	119.1 (4)	C14B—C21B—C20B	113.2 (4)
C8A—C13A—C12A	107.9 (3)	C20B—C21B—C22B	123.7 (4)
C8A—C13A—C14A	112.4 (4)	C21B—C22B—C23B	124.1 (4)
C15A—C14A—C21A	109.3 (4)	O24B—C23B—C22B	112.1 (4)
C13A—C14A—C15A	106.8 (4)	C2B—C1B—H1B	120.00
C13A—C14A—C21A	114.9 (4)	C6B—C1B—H1B	120.00
C14A—C15A—C16A	109.0 (4)	C3B—C4B—H4B	121.00
C7A—C16A—C15A	113.9 (4)	C5B—C4B—H4B	121.00
N19A—C16A—C15A	111.3 (3)	C13B—C8B—H8B	110.00
N19A—C16A—C7A	104.9 (3)	N9B—C8B—H8B	110.00
C7A—C17A—C18A	101.9 (3)	C7B—C8B—H8B	110.00
N19A—C18A—C17A	104.3 (3)	H91W—O9W—H92W	122
N19A—C20A—C21A	111.8 (4)	C12B—C11B—H11D	108.00
C14A—C21A—C20A	114.5 (4)	H11C—C11B—H11D	107.00
C14A—C21A—C22A	122.9 (5)	C12B—C11B—H11C	108.00
C20A—C21A—C22A	122.4 (5)	C10B—C11B—H11C	108.00
C21A—C22A—C23A	122.3 (5)	C10B—C11B—H11D	108.00
O24A—C23A—C22A	111.4 (5)	C11B—C12B—H12B	109.00
C6A—C1A—H1A	121.00	O24B—C12B—H12B	109.00
C2A—C1A—H1A	121.00	C13B—C12B—H12B	109.00
C5A—C4A—H4A	121.00	C8B—C13B—H13B	106.00
C3A—C4A—H4A	121.00	C12B—C13B—H13B	106.00
C13A—C8A—H8A	109.00	C14B—C13B—H13B	106.00
C7A—C8A—H8A	109.00	C15B—C14B—H14B	109.00
N9A—C8A—H8A	109.00	C21B—C14B—H14B	109.00
H81W—O8W—H82W	94	C13B—C14B—H14B	109.00
C10A—C11A—H11A	108.00	C16B—C15B—H15C	110.00
C12A—C11A—H11A	108.00	C14B—C15B—H15C	110.00
C10A—C11A—H11B	108.00	C14B—C15B—H15D	110.00
C12A—C11A—H11B	108.00	H15C—C15B—H15D	108.00
H11A—C11A—H11B	107.00	C16B—C15B—H15D	110.00
O24A—C12A—H12A	109.00	C15B—C16B—H16B	108.00
C11A—C12A—H12A	109.00	C7B—C16B—H16B	109.00
C13A—C12A—H12A	109.00	N19B—C16B—H16B	108.00
C12A—C13A—H13A	105.00	C7B—C17B—H17C	111.00
C14A—C13A—H13A	105.00	C7B—C17B—H17D	111.00
C8A—C13A—H13A	105.00	C18B—C17B—H17C	111.00
C15A—C14A—H14A	109.00	H17C—C17B—H17D	109.00
C13A—C14A—H14A	109.00	C18B—C17B—H17D	111.00
C21A—C14A—H14A	109.00	N19B—C18B—H18C	111.00
C16A—C15A—H15A	110.00	N19B—C18B—H18D	111.00
C16A—C15A—H15B	110.00	C17B—C18B—H18D	111.00
H15A—C15A—H15B	108.00	H18C—C18B—H18D	109.00
C14A—C15A—H15B	110.00	C17B—C18B—H18C	111.00
C14A—C15A—H15A	110.00	C21B—C20B—H20D	109.00
N19A—C16A—H16A	109.00	H20C—C20B—H20D	108.00
C15A—C16A—H16A	109.00	C21B—C20B—H20C	110.00
C7A—C16A—H16A	109.00	N19B—C20B—H20C	109.00
C7A—C17A—H17B	111.00	N19B—C20B—H20D	109.00
C7A—C17A—H17A	111.00	C21B—C22B—H22B	118.00
H17A—C17A—H17B	109.00	C23B—C22B—H22B	118.00
C18A—C17A—H17A	111.00	O24B—C23B—H23C	109.00
C18A—C17A—H17B	111.00	O24B—C23B—H23D	109.00
C17A—C18A—H18A	111.00	H23C—C23B—H23D	108.00
C17A—C18A—H18B	111.00	C22B—C23B—H23C	109.00
H18A—C18A—H18B	109.00	C22B—C23B—H23D	109.00
N19A—C18A—H18A	111.00	O2B—C25B—H25A	110.00
N19A—C18A—H18B	111.00	H25A—C25B—H25B	109.00
N19A—C20A—H20A	109.00	O2B—C25B—H25B	109.00
H20A—C20A—H20B	108.00	O2B—C25B—H25C	110.00
C21A—C20A—H20A	109.00	H25B—C25B—H25C	109.00
C21A—C20A—H20B	109.00	H25A—C25B—H25C	110.00
N19A—C20A—H20B	109.00	O3B—C35B—H35F	110.00
C21A—C22A—H22A	119.00	O3B—C35B—H35E	109.00
C23A—C22A—H22A	119.00	H35E—C35B—H35F	109.00
O24A—C23A—H23B	109.00	H35D—C35B—H35E	109.00
H23A—C23A—H23B	108.00	H35D—C35B—H35F	109.00
C22A—C23A—H23A	109.00	O3B—C35B—H35D	109.00
O24A—C23A—H23A	109.00	H17W—O12W—H18W	115
C25A—O2A—C2A—C1A	−1.1 (5)	C7A—C8A—C13A—C12A	172.6 (3)
C25A—O2A—C2A—C3A	177.5 (4)	O25A—C10A—C11A—C12A	142.0 (4)
C35A—O3A—C3A—C2A	−175.7 (4)	N9A—C10A—C11A—C12A	−39.4 (5)
C35A—O3A—C3A—C4A	4.9 (5)	C10A—C11A—C12A—C13A	9.1 (6)
C23A—O24A—C12A—C13A	−66.6 (5)	C10A—C11A—C12A—O24A	132.8 (4)
C23A—O24A—C12A—C11A	172.3 (4)	C11A—C12A—C13A—C8A	43.9 (5)
C12A—O24A—C23A—C22A	88.3 (5)	O24A—C12A—C13A—C8A	−74.6 (4)
C25B—O2B—C2B—C1B	0.4 (5)	C11A—C12A—C13A—C14A	173.6 (4)
C25B—O2B—C2B—C3B	178.9 (3)	O24A—C12A—C13A—C14A	55.1 (5)
C35B—O3B—C3B—C4B	1.9 (5)	C12A—C13A—C14A—C21A	−65.7 (5)
C35B—O3B—C3B—C2B	−179.1 (3)	C8A—C13A—C14A—C21A	61.9 (5)
C12B—O24B—C23B—C22B	87.3 (5)	C12A—C13A—C14A—C15A	173.0 (4)
C23B—O24B—C12B—C11B	169.4 (3)	C8A—C13A—C14A—C15A	−59.4 (5)
C23B—O24B—C12B—C13B	−71.0 (5)	C15A—C14A—C21A—C20A	0.8 (6)
C5A—N9A—C8A—C7A	11.3 (4)	C13A—C14A—C21A—C22A	56.5 (6)
C8A—N9A—C5A—C6A	−1.9 (4)	C15A—C14A—C21A—C22A	176.5 (5)
C10A—N9A—C5A—C6A	−156.9 (4)	C13A—C14A—C15A—C16A	69.1 (5)
C8A—N9A—C5A—C4A	178.9 (4)	C21A—C14A—C15A—C16A	−55.7 (5)
C5A—N9A—C8A—C13A	−114.3 (3)	C13A—C14A—C21A—C20A	−119.1 (5)
C10A—N9A—C8A—C7A	168.2 (3)	C14A—C15A—C16A—C7A	−57.6 (5)
C10A—N9A—C5A—C4A	24.0 (6)	C14A—C15A—C16A—N19A	60.7 (5)
C5A—N9A—C10A—O25A	−17.5 (6)	C7A—C17A—C18A—N19A	40.7 (4)
C5A—N9A—C10A—C11A	163.8 (4)	N19A—C20A—C21A—C14A	51.8 (5)
C10A—N9A—C8A—C13A	42.6 (4)	N19A—C20A—C21A—C22A	−123.9 (5)
C8A—N9A—C10A—C11A	11.3 (5)	C20A—C21A—C22A—C23A	175.0 (5)
C8A—N9A—C10A—O25A	−170.0 (3)	C14A—C21A—C22A—C23A	−0.4 (8)
C16A—N19A—C18A—C17A	−19.9 (5)	C21A—C22A—C23A—O24A	−65.8 (7)
C16A—N19A—C20A—C21A	−47.5 (5)	C2B—C1B—C6B—C7B	−174.3 (3)
C20A—N19A—C16A—C15A	−7.8 (6)	C6B—C1B—C2B—C3B	2.2 (5)
C20A—N19A—C16A—C7A	115.8 (4)	C6B—C1B—C2B—O2B	−179.4 (3)
C18A—N19A—C16A—C15A	−131.8 (4)	C2B—C1B—C6B—C5B	−1.7 (5)
C18A—N19A—C16A—C7A	−8.2 (5)	C1B—C2B—C3B—C4B	−1.6 (5)
C18A—N19A—C20A—C21A	74.6 (5)	C1B—C2B—C3B—O3B	179.4 (3)
C20A—N19A—C18A—C17A	−145.1 (4)	O2B—C2B—C3B—C4B	179.9 (3)
C10B—N9B—C5B—C4B	19.1 (6)	O2B—C2B—C3B—O3B	0.8 (5)
C8B—N9B—C5B—C4B	175.5 (3)	C2B—C3B—C4B—C5B	0.4 (5)
C10B—N9B—C5B—C6B	−159.0 (4)	O3B—C3B—C4B—C5B	179.4 (3)
C10B—N9B—C8B—C7B	169.7 (4)	C3B—C4B—C5B—C6B	0.1 (5)
C8B—N9B—C10B—O25B	−174.5 (4)	C3B—C4B—C5B—N9B	−177.8 (3)
C5B—N9B—C8B—C13B	−113.2 (4)	N9B—C5B—C6B—C1B	178.8 (3)
C5B—N9B—C8B—C7B	11.1 (4)	C4B—C5B—C6B—C1B	0.6 (5)
C8B—N9B—C5B—C6B	−2.6 (4)	C4B—C5B—C6B—C7B	174.3 (3)
C5B—N9B—C10B—O25B	−20.2 (7)	N9B—C5B—C6B—C7B	−7.5 (4)
C8B—N9B—C10B—C11B	6.5 (6)	C5B—C6B—C7B—C8B	13.8 (4)
C10B—N9B—C8B—C13B	45.4 (5)	C5B—C6B—C7B—C17B	−105.1 (4)
C5B—N9B—C10B—C11B	160.8 (4)	C1B—C6B—C7B—C16B	−47.6 (5)
C20B—N19B—C16B—C15B	−7.9 (5)	C1B—C6B—C7B—C17B	68.1 (5)
C20B—N19B—C16B—C7B	116.7 (4)	C1B—C6B—C7B—C8B	−173.0 (3)
C18B—N19B—C16B—C15B	−132.2 (4)	C5B—C6B—C7B—C16B	139.2 (4)
C16B—N19B—C20B—C21B	−49.1 (5)	C8B—C7B—C16B—C15B	33.7 (5)
C18B—N19B—C20B—C21B	73.4 (5)	C6B—C7B—C8B—C13B	101.9 (4)
C16B—N19B—C18B—C17B	−18.7 (5)	C6B—C7B—C8B—N9B	−14.4 (3)
C18B—N19B—C16B—C7B	−7.6 (5)	C17B—C7B—C16B—N19B	30.5 (5)
C20B—N19B—C18B—C17B	−143.8 (4)	C6B—C7B—C16B—C15B	−85.4 (5)
C2A—C1A—C6A—C5A	−0.5 (5)	C6B—C7B—C16B—N19B	151.9 (4)
C6A—C1A—C2A—C3A	2.1 (5)	C8B—C7B—C17B—C18B	80.3 (4)
C6A—C1A—C2A—O2A	−179.4 (3)	C16B—C7B—C17B—C18B	−41.8 (4)
C2A—C1A—C6A—C7A	−170.2 (3)	C17B—C7B—C16B—C15B	153.2 (4)
O2A—C2A—C3A—O3A	−0.3 (5)	C17B—C7B—C8B—C13B	−138.5 (4)
C1A—C2A—C3A—C4A	−2.3 (5)	C16B—C7B—C8B—C13B	−24.2 (5)
C1A—C2A—C3A—O3A	178.3 (3)	C6B—C7B—C17B—C18B	−165.8 (4)
O2A—C2A—C3A—C4A	179.0 (3)	C17B—C7B—C8B—N9B	105.2 (4)
O3A—C3A—C4A—C5A	−179.8 (3)	C8B—C7B—C16B—N19B	−89.0 (4)
C2A—C3A—C4A—C5A	0.9 (5)	C16B—C7B—C8B—N9B	−140.6 (3)
C3A—C4A—C5A—N9A	179.8 (3)	C7B—C8B—C13B—C14B	38.6 (5)
C3A—C4A—C5A—C6A	0.7 (5)	N9B—C8B—C13B—C12B	−73.2 (4)
C4A—C5A—C6A—C1A	−0.9 (6)	N9B—C8B—C13B—C14B	154.7 (4)
N9A—C5A—C6A—C1A	179.9 (3)	C7B—C8B—C13B—C12B	170.7 (3)
C4A—C5A—C6A—C7A	170.4 (3)	O25B—C10B—C11B—C12B	148.2 (5)
N9A—C5A—C6A—C7A	−8.8 (4)	N9B—C10B—C11B—C12B	−32.8 (6)
C5A—C6A—C7A—C16A	141.0 (4)	C10B—C11B—C12B—C13B	2.8 (6)
C5A—C6A—C7A—C8A	15.2 (4)	C10B—C11B—C12B—O24B	125.4 (4)
C5A—C6A—C7A—C17A	−104.1 (4)	O24B—C12B—C13B—C14B	59.3 (5)
C1A—C6A—C7A—C17A	66.4 (5)	O24B—C12B—C13B—C8B	−69.4 (4)
C1A—C6A—C7A—C8A	−174.3 (3)	C11B—C12B—C13B—C14B	176.8 (4)
C1A—C6A—C7A—C16A	−48.5 (6)	C11B—C12B—C13B—C8B	48.1 (4)
C6A—C7A—C8A—C13A	101.9 (4)	C8B—C13B—C14B—C15B	−60.3 (4)
C17A—C7A—C8A—C13A	−138.8 (3)	C12B—C13B—C14B—C21B	−65.1 (5)
C8A—C7A—C16A—C15A	35.0 (5)	C12B—C13B—C14B—C15B	174.0 (3)
C16A—C7A—C17A—C18A	−44.4 (4)	C8B—C13B—C14B—C21B	60.7 (5)
C17A—C7A—C16A—N19A	32.6 (4)	C13B—C14B—C15B—C16B	69.8 (4)
C17A—C7A—C8A—N9A	103.9 (3)	C15B—C14B—C21B—C20B	−1.8 (5)
C6A—C7A—C16A—C15A	−84.6 (5)	C13B—C14B—C21B—C22B	54.7 (7)
C6A—C7A—C8A—N9A	−15.4 (3)	C13B—C14B—C21B—C20B	−120.9 (5)
C16A—C7A—C8A—N9A	−143.3 (3)	C21B—C14B—C15B—C16B	−54.5 (5)
C6A—C7A—C16A—N19A	153.5 (4)	C15B—C14B—C21B—C22B	173.8 (5)
C8A—C7A—C17A—C18A	77.0 (4)	C14B—C15B—C16B—N19B	61.4 (4)
C6A—C7A—C17A—C18A	−169.5 (4)	C14B—C15B—C16B—C7B	−57.8 (5)
C17A—C7A—C16A—C15A	154.5 (3)	C7B—C17B—C18B—N19B	37.8 (4)
C16A—C7A—C8A—C13A	−26.0 (5)	N19B—C20B—C21B—C22B	−120.8 (5)
C8A—C7A—C16A—N19A	−86.9 (4)	N19B—C20B—C21B—C14B	54.7 (5)
N9A—C8A—C13A—C12A	−70.2 (4)	C14B—C21B—C22B—C23B	−2.3 (8)
N9A—C8A—C13A—C14A	156.4 (3)	C20B—C21B—C22B—C23B	172.8 (5)
C7A—C8A—C13A—C14A	39.2 (5)	C21B—C22B—C23B—O24B	−61.6 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11W···O4W^i	0.91	1.90	2.813 (8)	179
O1W—H12W···O6W	0.71	2.12	2.776 (6)	154
O2W—H21W···O6W^ii	0.89	1.85	2.739 (6)	179
O2W—H22W···O4W	0.82	1.98	2.769 (6)	162
O3W—H31W···O8W^iii	0.92	1.77	2.688 (6)	179
O3W—H32W···O25B	0.90	1.92	2.811 (7)	179
O4W—H41W···O9W^iv	0.90	1.83	2.731 (7)	179
O4W—H42W···N19A	0.92	1.86	2.742 (7)	158
O5W—H51W···O25B^v	0.86	2.16	2.942 (8)	150
O5W—H52W···O8W	0.91	1.89	2.798 (8)	179
O6W—H61W···O25A	0.97	1.78	2.746 (5)	176
O6W—H62W···O6W^vi	0.83	2.29	2.756 (5)	116
O7W—H71W···O2B	0.93	2.27	2.986 (5)	133
O7W—H71W···O3B	0.93	2.26	3.096 (6)	148
O7W—H72W···O3W^vii	0.91	1.84	2.746 (8)	179
O8W—H81W···N19B	0.90	1.81	2.714 (5)	180
O8W—H82W···O2W^viii	0.91	1.82	2.727 (6)	179
O9W—H91W···O3A	0.87	2.16	2.987 (6)	158
O9W—H92W···O7W^iii	0.96	1.93	2.797 (7)	149
O10W—H13W···O1W	0.89	2.01	2.907 (11)	179
O10W—H14W···O24A^vi	0.90	1.81	2.711 (11)	179
O11W—H15W···O1W	0.89	1.89	2.777 (11)	179
O11W—H16W···O24A^vi	0.88	2.19	3.069 (11)	179
O12W—H17W···O5W^iii	0.90	1.75	2.646 (19)	179
O12W—H18W···O5W^ix	0.89	2.26	3.154 (19)	179
C1A—H1A···O2W	0.95	2.56	3.472 (7)	160
C4A—H4A···O25A	0.95	2.38	2.903 (6)	114
C4B—H4B···O25B	0.95	2.44	2.957 (6)	114
C8B—H8B···O24B	1.00	2.58	2.996 (5)	105
C12A—H12A···O7W	1.00	2.55	3.546 (7)	172
C23A—H23B···O2A^viii	0.99	2.54	3.371 (6)	141
C35B—H35E···O12W	0.98	2.50	2.996 (15)	111

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