9-O-Ethyl-berberrubinium iodide monohydrate.

IN THE TITLE COMPOUND (SYSTEMATIC NAME: 9-eth-oxy-10-meth-oxy-5,6-dihydro-1,3-dioxolo[4,5-g]isoquinolino-[3,2-a]isoquin-olin-7-ium iodide monohydrate), 2C(21)H(20)NO(4) (+)·2I(-)·H(2)O, two independent mol-ecules pack in the unit cell, where interactions between the molecules are stabilized by weak inter-molecular π-π stacking inter-actions [centroid-centroid distances in the range 3.571 (4) to 3.815 (4)Å]. Inter-molecular C-H⋯O inter-actions are also observed. The iodide anions are disordered with occupancy ratios of 0.94 (1):0.06 (1) and 0.91 (1):0.09 (1). The cationic molecule is planar in structure with a small torsion resulting from the dihydropyridine ring.

Related literature

For the synthesis of the title compound, see: Iwasa et al. (1997 ▶). The title compound is a derivative of the natural product berberine. For the anti-parasitic activity of berberine and its derivatives, see: Nkwengoua et al. (2009 ▶); Acero et al. (1995 ▶); Ghosh et al. (1985 ▶); Wright et al. (2000 ▶); Iwasa et al. (1998 ▶); Sheng et al. 1997 ▶); McCall et al. (1994 ▶). For a related structure, see: Chen et al. (2009 ▶). For the Chebychev weighting scheme, see: Prince (1982 ▶); Watkin (1994 ▶).

Experimental

Crystal data

2C21H20NO4 +·2I−·H2O

M = 972.61

Triclinic,

a = 11.036 (3) Å

b = 13.449 (4) Å

c = 14.086 (4) Å

α = 80.442 (6)°

β = 71.121 (5)°

γ = 76.875 (5)°

V = 1916.8 (9) Å3

Z = 2

Mo Kα radiation

μ = 1.70 mm−1

T = 93 K

1.00 × 0.10 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID II image plate diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.469, T max = 0.712

50086 measured reflections

8751 independent reflections

4563 reflections with I > 2.0σ(I)

R int = 0.101

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.195

S = 0.96

8751 reflections

502 parameters

12 restraints

All H-atom parameters refined

Δρmax = 1.75 e Å−3

Δρmin = −2.26 e Å−3

Data collection: CrystalClear (Rigaku, 2009 ▶); cell refinement: HKL-2000 (Otwinowski & Minor, 1997 ▶); data reduction: CrystalClear; program(s) used to solve structure: CrystalStructure (Rigaku, 2009 ▶) and SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: CAMERON (Watkin et al., 1996 ▶); software used to prepare material for publication: CRYSTALS.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810036664/jj2056sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810036664/jj2056Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

2C21H20NO4+·2I−·H2O	Z = 2
Mr = 972.61	F(000) = 972
Triclinic, P1	Dx = 1.685 Mg m−3
Hall symbol: -P 1	Melting point: 257 K
a = 11.036 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.449 (4) Å	Cell parameters from 50086 reflections
c = 14.086 (4) Å	θ = 3–27.5°
α = 80.442 (6)°	µ = 1.70 mm−1
β = 71.121 (5)°	T = 93 K
γ = 76.875 (5)°	Needle, yellow
V = 1916.8 (9) Å3	1.00 × 0.10 × 0.10 mm

Rigaku R-AXIS RAPID II image plate diffractometer	8751 independent reflections
Radiation source: Mo sealed tube	4563 reflections with I > 2.0σ(I)
graphite	Rint = 0.101
Detector resolution: 10 pixels mm-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −14→14
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −17→17
Tmin = 0.469, Tmax = 0.712	l = −18→18
50086 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.195	All H-atom parameters refined
S = 0.96	Method, part 1, Chebychev polynomial, (Watkin, 1994; Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)] where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)2]2 Ai are: 4.85 6.23 1.54
8751 reflections	(Δ/σ)max = 0.001
502 parameters	Δρmax = 1.75 e Å−3
12 restraints	Δρmin = −2.26 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1A	0.7061 (5)	0.4522 (4)	0.7015 (4)	0.0527
C1A	0.5927 (8)	0.5331 (6)	0.7096 (6)	0.0517
O2A	0.5226 (6)	0.5086 (4)	0.6480 (4)	0.0577
C2A	0.5222 (8)	0.3441 (6)	0.5954 (6)	0.0554
C3A	0.5468 (8)	0.1682 (6)	0.5415 (6)	0.0552
C4A	0.5678 (7)	0.0617 (6)	0.5900 (6)	0.0511
N1A	0.7020 (5)	0.0278 (4)	0.5983 (4)	0.0413
C5A	0.7560 (7)	−0.0722 (5)	0.5920 (5)	0.0413
C6A	0.9343 (6)	−0.2175 (5)	0.6016 (5)	0.0401
C7A	1.0547 (7)	−0.2531 (5)	0.6186 (5)	0.0436
C8A	1.1203 (6)	−0.1848 (5)	0.6375 (5)	0.0417
C9A	1.0685 (7)	−0.0817 (5)	0.6410 (5)	0.0440
C10A	0.8835 (6)	0.0610 (5)	0.6336 (5)	0.0398
C11A	0.7418 (7)	0.2722 (5)	0.6670 (5)	0.0462
C12A	0.6771 (7)	0.3709 (5)	0.6694 (5)	0.0437
C13A	0.5686 (7)	0.4057 (6)	0.6358 (6)	0.0490
C14A	0.5878 (7)	0.2405 (5)	0.5902 (5)	0.0438
C15A	0.8781 (6)	−0.1118 (5)	0.6061 (4)	0.0392
C16A	0.9456 (6)	−0.0429 (5)	0.6270 (5)	0.0411
C17A	0.7628 (6)	0.0966 (5)	0.6204 (4)	0.0378
C18A	0.6934 (6)	0.2049 (5)	0.6268 (5)	0.0406
O3A	1.1012 (5)	−0.3557 (4)	0.6163 (4)	0.0471
O4A	0.8648 (5)	−0.2821 (3)	0.5852 (3)	0.0428
C19A	1.2226 (8)	−0.3942 (5)	0.6361 (6)	0.0497
C20A	0.9150 (8)	−0.3152 (6)	0.4853 (5)	0.0531
C21A	0.8288 (9)	−0.3797 (7)	0.4743 (7)	0.0662
O1B	0.7780 (5)	−0.4304 (3)	0.8199 (4)	0.0481
C1B	0.8993 (7)	−0.5023 (5)	0.7914 (6)	0.0507
O2B	0.9851 (5)	−0.4741 (4)	0.8366 (4)	0.0528
C2B	0.9914 (7)	−0.3031 (6)	0.8764 (5)	0.0471
C3B	0.9793 (7)	−0.1200 (5)	0.9045 (5)	0.0463
C4B	0.8775 (7)	−0.0374 (5)	0.9633 (6)	0.0468
N1B	0.7687 (5)	−0.0013 (4)	0.9196 (4)	0.0390
C5B	0.7139 (7)	0.0966 (5)	0.9225 (5)	0.0442
C6B	0.5421 (7)	0.2398 (5)	0.8997 (5)	0.0433
C7B	0.4229 (6)	0.2745 (5)	0.8790 (5)	0.0423
C8B	0.3624 (6)	0.2055 (5)	0.8563 (5)	0.0412
C9B	0.4177 (6)	0.1029 (5)	0.8509 (5)	0.0399
C10B	0.6057 (6)	−0.0366 (5)	0.8629 (4)	0.0368
C11B	0.7373 (6)	−0.2504 (5)	0.8535 (5)	0.0415
C12B	0.8119 (6)	−0.3468 (5)	0.8398 (5)	0.0407
C13B	0.9343 (7)	−0.3723 (5)	0.8522 (5)	0.0449
C14B	0.9186 (6)	−0.2035 (5)	0.8885 (5)	0.0433
C15B	0.5975 (6)	0.1356 (5)	0.8969 (5)	0.0399
C16B	0.5391 (6)	0.0654 (5)	0.8706 (4)	0.0363
C17B	0.7212 (6)	−0.0725 (5)	0.8861 (4)	0.0371
C18B	0.7938 (6)	−0.1769 (5)	0.8779 (5)	0.0400
O4B	0.6121 (5)	0.3048 (4)	0.9131 (4)	0.0498
O3B	0.3732 (5)	0.3765 (4)	0.8823 (4)	0.0489
C19B	0.2472 (8)	0.4115 (6)	0.8666 (7)	0.0569
C20B	0.5681 (9)	0.3468 (11)	1.0051 (8)	0.0893
C21B	0.6740 (9)	0.3896 (8)	1.0199 (6)	0.0634
O5	1.2817 (6)	0.0700 (5)	0.6183 (4)	0.0635
I1A	1.02838 (5)	0.19860 (3)	0.80552 (4)	0.0447	0.9379
I1A'	1.1037 (7)	0.1783 (5)	0.7437 (6)	0.0447	0.0621
I1B	1.39483 (6)	−0.16491 (4)	0.75430 (5)	0.0520	0.9057
I1B'	1.4616 (6)	−0.1882 (4)	0.7030 (5)	0.0520	0.0943
H1A	0.6187	0.5993	0.6853	0.0619*
H2A	0.5380	0.5327	0.7790	0.0618*
H3A	0.4499	0.3682	0.5718	0.0661*
H4A	0.5966	0.1695	0.4707	0.0661*
H5A	0.4542	0.1889	0.5483	0.0663*
H6A	0.5042	0.0590	0.6571	0.0612*
H7A	0.5560	0.0157	0.5490	0.0607*
H8A	0.7107	−0.1157	0.5775	0.0495*
H9A	1.2018	−0.2098	0.6474	0.0498*
H10A	1.1145	−0.0368	0.6524	0.0527*
H11A	0.9261	0.1064	0.6479	0.0480*
H12A	0.8143	0.2501	0.6909	0.0558*
H13A	1.2430	−0.4679	0.6357	0.0750*
H14A	1.2168	−0.3759	0.7007	0.0748*
H15A	1.2896	−0.3646	0.5852	0.0749*
H16A	1.0021	−0.3568	0.4784	0.0636*
H17A	0.9200	−0.2562	0.4342	0.0642*
H18A	0.8548	−0.3958	0.4057	0.0992*
H19A	0.8354	−0.4422	0.5184	0.0988*
H20A	0.7397	−0.3432	0.4928	0.0989*
H1B	0.8849	−0.5716	0.8167	0.0610*
H2B	0.9354	−0.4972	0.7183	0.0609*
H3B	1.0747	−0.3211	0.8837	0.0571*
H4B	1.0408	−0.1494	0.9427	0.0559*
H5B	1.0244	−0.0878	0.8384	0.0558*
H6B	0.8441	−0.0668	1.0323	0.0558*
H7B	0.9172	0.0200	0.9622	0.0559*
H8B	0.7535	0.1410	0.9415	0.0528*
H9B	0.2816	0.2301	0.8448	0.0488*
H10B	0.3754	0.0586	0.8342	0.0478*
H11B	0.5706	−0.0817	0.8411	0.0439*
H12B	0.6540	−0.2340	0.8465	0.0500*
H13B	0.2236	0.4843	0.8700	0.0849*
H14B	0.1834	0.3776	0.9178	0.0848*
H15B	0.2506	0.3966	0.8011	0.0848*
H16B	0.5428	0.2942	1.0590	0.1070*
H17B	0.4937	0.4011	1.0052	0.1071*
H18B	0.6422	0.4194	1.0829	0.0951*
H19B	0.7468	0.3356	1.0206	0.0951*
H20B	0.6997	0.4413	0.9653	0.0949*
H21	1.2190	0.0950	0.6740	0.0941*
H22	1.2916	0.0105	0.6502	0.0944*

	U11	U22	U33	U12	U13	U23
O1A	0.058 (3)	0.040 (2)	0.063 (3)	−0.006 (2)	−0.024 (2)	−0.005 (2)
C1A	0.055 (4)	0.042 (3)	0.061 (4)	−0.003 (3)	−0.022 (3)	−0.010 (3)
O2A	0.065 (3)	0.045 (3)	0.069 (3)	0.000 (2)	−0.028 (3)	−0.019 (2)
C2A	0.059 (4)	0.055 (4)	0.062 (4)	−0.004 (3)	−0.033 (4)	−0.015 (3)
C3A	0.055 (4)	0.059 (4)	0.059 (4)	−0.011 (3)	−0.022 (3)	−0.013 (3)
C4A	0.044 (3)	0.053 (4)	0.065 (4)	−0.019 (3)	−0.024 (3)	−0.002 (3)
N1A	0.045 (3)	0.043 (3)	0.041 (3)	−0.013 (2)	−0.016 (2)	−0.006 (2)
C5A	0.048 (3)	0.045 (3)	0.038 (3)	−0.018 (3)	−0.017 (3)	−0.004 (2)
C6A	0.048 (3)	0.038 (3)	0.040 (3)	−0.011 (3)	−0.015 (3)	−0.009 (2)
C7A	0.052 (4)	0.042 (3)	0.041 (3)	−0.012 (3)	−0.017 (3)	−0.005 (2)
C8A	0.043 (3)	0.046 (3)	0.041 (3)	−0.010 (3)	−0.018 (3)	−0.003 (3)
C9A	0.052 (4)	0.048 (3)	0.041 (3)	−0.018 (3)	−0.018 (3)	−0.009 (3)
C10A	0.041 (3)	0.044 (3)	0.041 (3)	−0.006 (3)	−0.020 (3)	−0.010 (2)
C11A	0.055 (4)	0.041 (3)	0.050 (4)	−0.017 (3)	−0.022 (3)	−0.001 (3)
C12A	0.051 (4)	0.045 (3)	0.038 (3)	−0.016 (3)	−0.014 (3)	−0.004 (2)
C13A	0.052 (4)	0.048 (4)	0.050 (4)	−0.004 (3)	−0.018 (3)	−0.013 (3)
C14A	0.044 (3)	0.043 (3)	0.048 (3)	−0.006 (3)	−0.016 (3)	−0.011 (3)
C15A	0.048 (3)	0.042 (3)	0.032 (3)	−0.013 (3)	−0.013 (2)	−0.006 (2)
C16A	0.047 (3)	0.046 (3)	0.033 (3)	−0.015 (3)	−0.013 (3)	−0.003 (2)
C17A	0.041 (3)	0.042 (3)	0.035 (3)	−0.009 (2)	−0.014 (2)	−0.007 (2)
C18A	0.042 (3)	0.046 (3)	0.037 (3)	−0.010 (3)	−0.015 (3)	−0.006 (2)
O3A	0.053 (3)	0.040 (2)	0.055 (3)	−0.007 (2)	−0.024 (2)	−0.008 (2)
O4A	0.051 (3)	0.041 (2)	0.044 (2)	−0.016 (2)	−0.017 (2)	−0.0088 (18)
C19A	0.058 (4)	0.038 (3)	0.058 (4)	−0.002 (3)	−0.027 (3)	−0.008 (3)
C20A	0.054 (4)	0.068 (5)	0.046 (4)	−0.016 (3)	−0.016 (3)	−0.019 (3)
C21A	0.067 (5)	0.075 (5)	0.066 (5)	−0.034 (4)	−0.009 (4)	−0.027 (4)
O1B	0.046 (2)	0.033 (2)	0.071 (3)	−0.0049 (19)	−0.026 (2)	−0.011 (2)
C1B	0.046 (4)	0.038 (3)	0.068 (4)	0.000 (3)	−0.021 (3)	−0.011 (3)
O2B	0.056 (3)	0.039 (2)	0.070 (3)	0.001 (2)	−0.026 (3)	−0.020 (2)
C2B	0.045 (3)	0.054 (4)	0.046 (3)	−0.002 (3)	−0.017 (3)	−0.017 (3)
C3B	0.042 (3)	0.050 (4)	0.053 (4)	−0.006 (3)	−0.019 (3)	−0.015 (3)
C4B	0.050 (4)	0.043 (3)	0.058 (4)	−0.004 (3)	−0.030 (3)	−0.013 (3)
N1B	0.035 (2)	0.044 (3)	0.047 (3)	−0.010 (2)	−0.021 (2)	−0.007 (2)
C5B	0.049 (4)	0.041 (3)	0.050 (3)	−0.014 (3)	−0.020 (3)	−0.007 (3)
C6B	0.047 (3)	0.039 (3)	0.048 (3)	−0.011 (3)	−0.017 (3)	−0.008 (3)
C7B	0.042 (3)	0.041 (3)	0.044 (3)	−0.006 (3)	−0.012 (3)	−0.010 (3)
C8B	0.042 (3)	0.042 (3)	0.043 (3)	−0.005 (3)	−0.017 (3)	−0.008 (2)
C9B	0.042 (3)	0.044 (3)	0.042 (3)	−0.012 (3)	−0.020 (3)	−0.008 (2)
C10B	0.040 (3)	0.039 (3)	0.039 (3)	−0.010 (2)	−0.018 (2)	−0.008 (2)
C11B	0.044 (3)	0.034 (3)	0.050 (3)	−0.008 (2)	−0.019 (3)	−0.003 (2)
C12B	0.042 (3)	0.035 (3)	0.049 (3)	−0.012 (2)	−0.015 (3)	−0.005 (2)
C13B	0.049 (4)	0.042 (3)	0.047 (3)	−0.002 (3)	−0.020 (3)	−0.009 (3)
C14B	0.042 (3)	0.051 (4)	0.044 (3)	−0.011 (3)	−0.017 (3)	−0.012 (3)
C15B	0.044 (3)	0.041 (3)	0.040 (3)	−0.012 (3)	−0.016 (3)	−0.007 (2)
C16B	0.033 (3)	0.042 (3)	0.037 (3)	−0.009 (2)	−0.010 (2)	−0.009 (2)
C17B	0.039 (3)	0.042 (3)	0.037 (3)	−0.011 (2)	−0.016 (2)	−0.008 (2)
C18B	0.043 (3)	0.041 (3)	0.041 (3)	−0.010 (3)	−0.017 (3)	−0.006 (2)
O4B	0.054 (3)	0.045 (2)	0.055 (3)	−0.017 (2)	−0.012 (2)	−0.017 (2)
O3B	0.053 (3)	0.036 (2)	0.062 (3)	−0.004 (2)	−0.024 (2)	−0.008 (2)
C19B	0.062 (5)	0.045 (4)	0.071 (5)	0.001 (3)	−0.035 (4)	−0.010 (3)
C20B	0.062 (5)	0.154 (11)	0.070 (6)	−0.041 (6)	−0.002 (4)	−0.068 (7)
C21B	0.062 (5)	0.092 (6)	0.049 (4)	−0.036 (5)	−0.019 (4)	−0.010 (4)
O5	0.060 (3)	0.081 (4)	0.054 (3)	−0.023 (3)	−0.017 (3)	−0.006 (3)
I1A	0.0507 (3)	0.0426 (2)	0.0484 (3)	−0.01080 (19)	−0.0248 (2)	−0.00267 (18)
I1A'	0.0507 (3)	0.0426 (2)	0.0484 (3)	−0.01080 (19)	−0.0248 (2)	−0.00267 (18)
I1B	0.0614 (3)	0.0476 (3)	0.0631 (3)	−0.0168 (2)	−0.0366 (3)	−0.0039 (2)
I1B'	0.0614 (3)	0.0476 (3)	0.0631 (3)	−0.0168 (2)	−0.0366 (3)	−0.0039 (2)

O1A—C1A	1.446 (9)	O1B—C12B	1.358 (7)
O1A—C12A	1.386 (8)	C1B—O2B	1.441 (9)
C1A—O2A	1.450 (9)	C1B—H1B	0.971
C1A—H1A	0.972	C1B—H2B	0.972
C1A—H2A	0.968	O2B—C13B	1.382 (8)
O2A—C13A	1.381 (9)	C2B—C13B	1.374 (10)
C2A—C13A	1.345 (10)	C2B—C14B	1.404 (10)
C2A—C14A	1.419 (10)	C2B—H3B	0.930
C2A—H3A	0.934	C3B—C4B	1.523 (10)
C3A—C4A	1.483 (11)	C3B—C14B	1.511 (9)
C3A—C14A	1.497 (10)	C3B—H4B	0.975
C3A—H4A	0.969	C3B—H5B	0.982
C3A—H5A	0.974	C4B—N1B	1.472 (8)
C4A—N1A	1.485 (9)	C4B—H6B	0.971
C4A—H6A	0.978	C4B—H7B	0.967
C4A—H7A	0.967	N1B—C5B	1.319 (8)
N1A—C5A	1.347 (9)	N1B—C17B	1.398 (7)
N1A—C17A	1.383 (8)	C5B—C15B	1.409 (9)
C5A—C15A	1.396 (9)	C5B—H8B	0.932
C5A—H8A	0.935	C6B—C7B	1.399 (9)
C6A—C7A	1.390 (9)	C6B—C15B	1.398 (9)
C6A—C15A	1.420 (9)	C6B—O4B	1.362 (8)
C6A—O4A	1.370 (7)	C7B—C8B	1.388 (9)
C7A—C8A	1.396 (9)	C7B—O3B	1.359 (8)
C7A—O3A	1.360 (8)	C8B—C9B	1.379 (9)
C8A—C9A	1.376 (10)	C8B—H9B	0.934
C8A—H9A	0.933	C9B—C16B	1.420 (8)
C9A—C16A	1.403 (9)	C9B—H10B	0.934
C9A—H10A	0.933	C10B—C16B	1.406 (8)
C10A—C16A	1.414 (9)	C10B—C17B	1.379 (8)
C10A—C17A	1.371 (8)	C10B—H11B	0.925
C10A—H11A	0.930	C11B—C12B	1.375 (9)
C11A—C12A	1.357 (10)	C11B—C18B	1.419 (8)
C11A—C18A	1.418 (9)	C11B—H12B	0.930
C11A—H12A	0.935	C12B—C13B	1.377 (9)
C12A—C13A	1.383 (10)	C14B—C18B	1.393 (9)
C14A—C18A	1.381 (9)	C15B—C16B	1.410 (8)
C15A—C16A	1.429 (8)	C17B—C18B	1.452 (9)
C17A—C18A	1.486 (9)	O4B—C20B	1.395 (9)
O3A—C19A	1.421 (9)	O3B—C19B	1.439 (9)
O4A—C20A	1.441 (8)	C19B—H13B	0.959
C19A—H13A	0.966	C19B—H14B	0.966
C19A—H14A	0.960	C19B—H15B	0.963
C19A—H15A	0.957	C20B—C21B	1.497 (11)
C20A—C21A	1.481 (10)	C20B—H16B	0.963
C20A—H16A	0.980	C20B—H17B	0.967
C20A—H17A	0.978	C21B—H18B	0.961
C21A—H18A	0.962	C21B—H19B	0.955
C21A—H19A	0.962	C21B—H20B	0.962
C21A—H20A	0.967	O5—H21	0.916
O1B—C1B	1.443 (8)	O5—H22	0.852
C1A—O1A—C12A	105.6 (5)	O1B—C1B—O2B	106.1 (5)
O1A—C1A—O2A	105.9 (5)	O1B—C1B—H1B	109.9
O1A—C1A—H1A	110.5	O2B—C1B—H1B	110.5
O2A—C1A—H1A	110.8	O1B—C1B—H2B	109.9
O1A—C1A—H2A	109.7	O2B—C1B—H2B	110.6
O2A—C1A—H2A	109.2	H1B—C1B—H2B	109.7
H1A—C1A—H2A	110.6	C1B—O2B—C13B	104.1 (5)
C1A—O2A—C13A	105.2 (5)	C13B—C2B—C14B	116.8 (6)
C13A—C2A—C14A	117.2 (7)	C13B—C2B—H3B	121.8
C13A—C2A—H3A	121.7	C14B—C2B—H3B	121.4
C14A—C2A—H3A	121.1	C4B—C3B—C14B	111.8 (6)
C4A—C3A—C14A	111.6 (6)	C4B—C3B—H4B	107.8
C4A—C3A—H4A	109.2	C14B—C3B—H4B	109.7
C14A—C3A—H4A	109.2	C4B—C3B—H5B	108.5
C4A—C3A—H5A	107.5	C14B—C3B—H5B	108.9
C14A—C3A—H5A	109.6	H4B—C3B—H5B	110.2
H4A—C3A—H5A	109.8	C3B—C4B—N1B	111.1 (5)
C3A—C4A—N1A	112.0 (6)	C3B—C4B—H6B	108.1
C3A—C4A—H6A	108.0	N1B—C4B—H6B	109.0
N1A—C4A—H6A	110.1	C3B—C4B—H7B	109.5
C3A—C4A—H7A	108.9	N1B—C4B—H7B	109.1
N1A—C4A—H7A	107.2	H6B—C4B—H7B	110.0
H6A—C4A—H7A	110.7	C4B—N1B—C5B	117.3 (5)
C4A—N1A—C5A	117.7 (5)	C4B—N1B—C17B	119.2 (5)
C4A—N1A—C17A	119.8 (6)	C5B—N1B—C17B	123.3 (5)
C5A—N1A—C17A	122.2 (6)	N1B—C5B—C15B	121.7 (6)
N1A—C5A—C15A	121.4 (6)	N1B—C5B—H8B	119.1
N1A—C5A—H8A	119.0	C15B—C5B—H8B	119.2
C15A—C5A—H8A	119.6	C7B—C6B—C15B	118.8 (6)
C7A—C6A—C15A	119.2 (6)	C7B—C6B—O4B	122.5 (6)
C7A—C6A—O4A	122.1 (6)	C15B—C6B—O4B	118.5 (6)
C15A—C6A—O4A	118.7 (6)	C6B—C7B—C8B	119.7 (6)
C6A—C7A—C8A	120.0 (6)	C6B—C7B—O3B	116.6 (6)
C6A—C7A—O3A	116.2 (6)	C8B—C7B—O3B	123.7 (6)
C8A—C7A—O3A	123.8 (6)	C7B—C8B—C9B	122.1 (6)
C7A—C8A—C9A	121.9 (6)	C7B—C8B—H9B	118.2
C7A—C8A—H9A	118.8	C9B—C8B—H9B	119.8
C9A—C8A—H9A	119.3	C8B—C9B—C16B	119.6 (5)
C8A—C9A—C16A	120.0 (6)	C8B—C9B—H10B	120.1
C8A—C9A—H10A	120.7	C16B—C9B—H10B	120.3
C16A—C9A—H10A	119.3	C16B—C10B—C17B	122.9 (5)
C16A—C10A—C17A	122.2 (6)	C16B—C10B—H11B	118.5
C16A—C10A—H11A	118.6	C17B—C10B—H11B	118.6
C17A—C10A—H11A	119.2	C12B—C11B—C18B	117.0 (6)
C12A—C11A—C18A	116.5 (6)	C12B—C11B—H12B	121.4
C12A—C11A—H12A	121.4	C18B—C11B—H12B	121.5
C18A—C11A—H12A	122.1	C11B—C12B—O1B	128.0 (6)
O1A—C12A—C11A	128.2 (6)	C11B—C12B—C13B	121.7 (6)
O1A—C12A—C13A	109.0 (6)	O1B—C12B—C13B	110.1 (6)
C11A—C12A—C13A	122.8 (6)	O2B—C13B—C12B	109.4 (6)
C12A—C13A—O2A	110.2 (6)	O2B—C13B—C2B	127.9 (6)
C12A—C13A—C2A	122.0 (7)	C12B—C13B—C2B	122.6 (6)
O2A—C13A—C2A	127.8 (7)	C3B—C14B—C2B	120.1 (6)
C3A—C14A—C2A	120.7 (6)	C3B—C14B—C18B	118.4 (6)
C3A—C14A—C18A	118.5 (6)	C2B—C14B—C18B	121.3 (6)
C2A—C14A—C18A	120.8 (6)	C5B—C15B—C6B	120.5 (6)
C6A—C15A—C5A	121.7 (6)	C5B—C15B—C16B	117.5 (6)
C6A—C15A—C16A	120.2 (6)	C6B—C15B—C16B	122.0 (6)
C5A—C15A—C16A	118.2 (6)	C9B—C16B—C15B	117.9 (6)
C15A—C16A—C10A	117.8 (6)	C9B—C16B—C10B	123.8 (5)
C15A—C16A—C9A	118.7 (6)	C15B—C16B—C10B	118.3 (5)
C10A—C16A—C9A	123.4 (6)	N1B—C17B—C10B	116.0 (5)
N1A—C17A—C10A	118.1 (6)	N1B—C17B—C18B	119.4 (5)
N1A—C17A—C18A	117.6 (5)	C10B—C17B—C18B	124.6 (5)
C10A—C17A—C18A	124.3 (6)	C17B—C18B—C11B	118.4 (6)
C17A—C18A—C11A	118.5 (6)	C17B—C18B—C14B	121.0 (6)
C17A—C18A—C14A	120.8 (6)	C11B—C18B—C14B	120.5 (6)
C11A—C18A—C14A	120.7 (6)	C6B—O4B—C20B	117.1 (6)
C7A—O3A—C19A	117.2 (5)	C7B—O3B—C19B	116.7 (5)
C6A—O4A—C20A	113.4 (5)	O3B—C19B—H13B	108.7
O3A—C19A—H13A	109.4	O3B—C19B—H14B	109.9
O3A—C19A—H14A	109.1	H13B—C19B—H14B	109.9
H13A—C19A—H14A	110.2	O3B—C19B—H15B	109.9
O3A—C19A—H15A	109.5	H13B—C19B—H15B	109.2
H13A—C19A—H15A	109.3	H14B—C19B—H15B	109.2
H14A—C19A—H15A	109.3	O4B—C20B—C21B	110.0 (7)
O4A—C20A—C21A	108.7 (6)	O4B—C20B—H16B	109.3
O4A—C20A—H16A	107.8	C21B—C20B—H16B	109.6
C21A—C20A—H16A	109.0	O4B—C20B—H17B	109.0
O4A—C20A—H17A	110.6	C21B—C20B—H17B	109.4
C21A—C20A—H17A	110.7	H16B—C20B—H17B	109.5
H16A—C20A—H17A	109.9	C20B—C21B—H18B	109.3
C20A—C21A—H18A	109.8	C20B—C21B—H19B	109.1
C20A—C21A—H19A	109.2	H18B—C21B—H19B	109.7
H18A—C21A—H19A	109.5	C20B—C21B—H20B	109.1
C20A—C21A—H20A	109.4	H18B—C21B—H20B	109.8
H18A—C21A—H20A	109.9	H19B—C21B—H20B	109.7
H19A—C21A—H20A	109.1	H21—O5—H22	90.7
C1B—O1B—C12B	104.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C9A—H10A···O5	0.93	2.47	3.358 (11)	159
C21B—H20B···O1Bi	0.96	2.51	3.466 (11)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9A—H10A⋯O5	0.93	2.47	3.358 (11)	159
C21B—H20B⋯O1Bi	0.96	2.51	3.466 (11)	177

Symmetry code: (i) .