Invariom structure refinement, electrostatic potential and toxicity of 4-O-methylalpinumiso­flavone, O,O-dimethylalpinumisoflavone and 5-O-methyl-4-O-(3-methylbut-2-en-1-yl)alpinum­isoflavone

The accurate X-ray single-crystal structures of the isoflavone compounds 4-O-methylalpinumisoflavone, O,O-dimethylalpinumisoflavone and 5-O-methyl-4-O-(3-methylbut-2-en-1-yl)alpinumisoflavone {alpinumisoflavone = 5-hydroxy-7-(4-hydroxyphenyl)-2,2-dimethyl-2H,6H-benzo[1,2-b:5,4-b']dipyran-6-one} from data sets measured at cryogenic temperature have been obtained from invariom modelling using theoretically predicted Hansen and Coppens multipole-model form factors, which describe the aspherical electron density distribution. Molecular dipole moments and electrostatic potentials obtained from invariom modelling are discussed and compared with results from ab initio theoretical calculations. All three studied compounds are solvent extracts of root bark or seed powder of Millettia thonningii (leguminosae), a plant molluscicide and cercaricide used in Franco West Africa as medication against various diseases. The compounds' toxicities to brine shrimp have been determined and their different potencies tentatively related to conformation differences, intramolecular contacts, dipole moments and electrostatic potential features.

Computing details

For all compounds, data collection: Bruker SMART; cell refinement: Bruker SMART. Data reduction: Bruker SAINT for 4-O-Methyl, O,O-Dimethyl; Bruker SAINT, SADABS for 5-O-Dimethyl. For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: Koritsanszky et al., (2003); molecular graphics: Koritsanszky et al., (2003); software used to prepare material for publication: Koritsanszky et al., (2003).

Figures

(4-O-Methyl)

Crystal data

C21H18O5	F(000) = 736
Mr = 350.35	Dx = 1.387 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6416 reflections
a = 8.3670 (2) Å	θ = 2.4–35.5°
b = 8.4724 (2) Å	µ = 0.10 mm^−1
c = 23.6852 (5) Å	T = 90 K
β = 92.514 (1)°	Plate-like, pale yellow
V = 1677.39 (7) Å^3	0.25 × 0.10 × 0.06 mm
Z = 4

Data collection

CCD area detector diffractometer	7659 independent reflections
Radiation source: fine-focus sealed tube	5021 reflections with > 2σ(F)
Graphite monochromator	Rint = 0.071
Detector resolution: 8.366 pixels mm^-1	θmax = 35.5°, θmin = 1.7°
phi and ω scans	h = −13→13
Absorption correction: empirical (using intensity measurements) SADABS by G. Sheldrick (Blessing, 1995)	k = −12→13
Tmin = 0.976, Tmax = 0.994	l = −35→38
47225 measured reflections

Refinement

Refinement on F	0 restraints
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.030	w1 = 1/[s^2(Fo)]
wR(F^2) = 0.021	(Δ/σ)max < 0.001
S = 1.14	Δρmax = 0.32 e Å^−3
5021 reflections	Δρmin = −0.18 e Å^−3
307 parameters

Special details

Geometry. The positions of the H atoms atoms were freely refined using invariom database pseudoatom parameters up to hexadecapoles. This procedure yields bond distances in better agreement with standard neutron results.

As local atomic site symmetry was employed for the multipole parameters, a local atomic coordinate system was necessary for ensuring the correct orientation of the aspherical electron density. Dummy atoms were therefore necessary in some cases.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O(1)	1.02958 (6)	0.38866 (6)	0.24177 (2)	0.015
O(2)	0.77989 (5)	0.45628 (6)	0.29736 (2)	0.015
O(3)	0.63127 (5)	0.74878 (6)	0.16839 (2)	0.014
O(4)	1.08493 (5)	0.65440 (6)	0.06660 (2)	0.02
O(5)	0.16107 (5)	0.59009 (6)	0.43879 (2)	0.018
C(1)	1.24933 (9)	0.53168 (11)	0.00103 (3)	0.022
C(2)	1.35060 (10)	0.75480 (10)	0.0637 (1)	0.024
C(3)	1.25051 (7)	0.60459 (8)	0.05985 (3)	0.014
C(4)	1.30702 (8)	0.48765 (9)	0.10395 (3)	0.018
C(5)	1.22254 (8)	0.44951 (9)	0.14854 (3)	0.016
C(6)	1.06672 (7)	0.52206 (8)	0.15600 (3)	0.012
C(7)	0.97486 (7)	0.49189 (8)	0.20247 (3)	0.011
C(8)	0.82558 (7)	0.56898 (8)	0.20857 (3)	0.011
C(9)	0.73334 (7)	0.54726 (8)	0.25802 (3)	0.011
C(10)	0.58320 (7)	0.63518 (8)	0.25875 (3)	0.012
C(11)	0.54354 (8)	0.72945 (8)	0.21387 (3)	0.013
C(12)	0.77315 (7)	0.67224 (8)	0.16527 (3)	0.012
C(13)	0.85998 (8)	0.70262 (8)	0.11789 (3)	0.013
C(14)	1.00637 (7)	0.62680 (8)	0.11382 (3)	0.013
C(15)	0.47183 (7)	0.62446 (8)	0.30601 (3)	0.012
C(16)	0.52746 (8)	0.60919 (8)	0.36253 (3)	0.014
C(17)	0.42124 (8)	0.60021 (8)	0.40577 (3)	0.015
C(18)	0.25576 (8)	0.60614 (8)	0.39382 (3)	0.014
C(19)	0.19838 (8)	0.62389 (8)	0.33796 (3)	0.015
C(20)	0.30649 (8)	0.63155 (8)	0.29484 (3)	0.014
C(21)	−0.00758 (9)	0.60693 (11)	0.42856 (4)	0.023
H(9)	0.9490 (10)	0.3900 (10)	0.271	0.020 (2)
H(1)	1.3710 (10)	0.4950 (10)	−0.009	0.047 (3)
H(2)	1.2070 (10)	0.6160 (10)	−0.031	0.041 (3)
H(3)	1.1730 (10)	0.4300 (10)	0	0.046 (3)
H(4)	1.4740 (10)	0.7260 (10)	0.057	0.049 (3)
H(5)	1.3080 (10)	0.8360 (10)	0.032	0.035 (3)
H(6)	1.3420 (10)	0.8050 (10)	0.105	0.045 (3)
H(7)	1.4240 (10)	0.4390 (10)	0.099	0.033 (3)
H(8)	1.2629 (9)	0.3700 (10)	0.1812 (3)	0.026 (2)
H(10)	0.4320 (10)	0.7980 (10)	0.21	0.028 (2)
H(11)	0.8159 (9)	0.7858 (10)	0.0846 (3)	0.024 (2)
H(12)	0.6554 (9)	0.6054 (10)	0.3728 (3)	0.021 (2)
H(13)	0.4624 (9)	0.5875 (10)	0.4498 (3)	0.025 (2)
H(14)	0.0710 (10)	0.6290 (10)	0.328	0.024 (2)
H(15)	0.2620 (10)	0.6380 (10)	0.253	0.028 (2)
H(16)	−0.0550 (10)	0.5130 (10)	0.4	0.039 (3)
H(17)	−0.0350 (10)	0.7210 (10)	0.41	0.044 (3)
H(18)	−0.0570 (10)	0.5990 (10)	0.469	0.033 (3)
DUM1	0.87109	0.59483	0.32688	0	0
DUM2	0.68546	0.65286	0.21077	0	0
DUM3	1.17195	0.57695	0.10708	0	0
DUM4	0.08722	0.62302	0.38359	0	0
DUM5	1.1622	0.55432	0.10633	0	0
DUM6	0.92239	0.59517	0.15915	0	0
DUM7	0.36567	0.61551	0.34923	0	0
DUM8	0.36191	0.61518	0.3506	0	0
DUM9	0.36379	0.61381	0.3507	0	0
DUM10	0.36378	0.61688	0.34914	0	0

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O(1)	0.0142 (2)	0.0141 (3)	0.0167 (2)	0.0024 (2)	−0.0011 (2)	0.0035 (2)
O(2)	0.0137 (2)	0.0174 (3)	0.0139 (2)	0.0031 (2)	0.0006 (2)	0.0065 (2)
O(3)	0.0137 (2)	0.0137 (3)	0.0148 (2)	0.0032 (2)	0.0007 (2)	0.0021 (2)
O(4)	0.0176 (2)	0.0253 (3)	0.0173 (3)	0.0085 (2)	0.0051 (2)	0.0069 (2)
O(5)	0.0169 (2)	0.0213 (3)	0.0159 (2)	0.0004 (2)	0.0034 (2)	−0.0001 (2)
C(1)	0.0210 (4)	0.0278 (5)	0.0184 (4)	0.0043 (3)	−0.0001 (3)	−0.0072 (3)
C(2)	0.0249 (4)	0.0184 (4)	0.0272 (4)	−0.0049 (3)	−0.0076 (3)	0.0034 (3)
C(3)	0.0131 (3)	0.0159 (4)	0.0145 (3)	0.0011 (3)	0.0023 (2)	0.0000 (3)
C(4)	0.0146 (3)	0.0191 (4)	0.0196 (4)	0.0052 (3)	0.0035 (3)	0.0039 (3)
C(5)	0.0132 (3)	0.0160 (4)	0.0188 (3)	0.0055 (3)	0.0017 (3)	0.0026 (3)
C(6)	0.0118 (3)	0.0118 (3)	0.0126 (3)	0.0022 (2)	0.0006 (2)	0.0011 (3)
C(7)	0.0109 (3)	0.0107 (3)	0.0127 (3)	0.0008 (2)	−0.0002 (2)	0.0004 (2)
C(8)	0.0109 (3)	0.0102 (3)	0.0118 (3)	0.0007 (2)	−0.0002 (2)	0.0009 (2)
C(9)	0.0113 (3)	0.0115 (3)	0.0115 (3)	0.0002 (2)	−0.0007 (2)	0.0016 (3)
C(10)	0.0115 (3)	0.0127 (3)	0.0114 (3)	0.0001 (2)	0.0021 (2)	0.0008 (3)
C(11)	0.0133 (3)	0.0132 (3)	0.0135 (3)	0.0029 (2)	0.0011 (2)	0.0016 (3)
C(12)	0.0118 (3)	0.0112 (3)	0.0116 (3)	0.0020 (2)	−0.0001 (2)	0.0009 (2)
C(13)	0.0136 (3)	0.0146 (3)	0.0121 (3)	0.0039 (2)	0.0020 (2)	0.0025 (3)
C(14)	0.0133 (3)	0.0125 (3)	0.0126 (3)	0.0024 (2)	0.0010 (2)	0.0009 (3)
C(15)	0.0107 (3)	0.0135 (3)	0.0116 (3)	−0.0010 (2)	0.0010 (2)	0.0004 (3)
C(16)	0.0128 (3)	0.0151 (3)	0.0128 (3)	−0.0008 (3)	−0.0005 (2)	−0.0004 (3)
C(17)	0.0140 (3)	0.0186 (4)	0.0123 (3)	−0.0003 (3)	−0.0002 (2)	−0.0008 (3)
C(18)	0.0133 (3)	0.0137 (3)	0.0135 (3)	−0.0001 (2)	0.0014 (2)	−0.0010 (3)
C(19)	0.0122 (3)	0.0189 (4)	0.0138 (3)	0.0000 (3)	0.0012 (2)	0.0004 (3)
C(20)	0.0114 (3)	0.0179 (4)	0.0135 (3)	0.0000 (2)	−0.0002 (2)	0.0005 (3)
C(21)	0.0169 (3)	0.0302 (5)	0.0223 (4)	0.0038 (3)	0.0069 (3)	0.0044 (4)

Geometric parameters (Å, º)

O(1)—C(7)	1.3431 (8)	C(7)—C(8)	1.4224 (9)
O(1)—H(9)	0.988 (9)	C(8)—C(9)	1.4423 (9)
O(2)—C(9)	1.2579 (7)	C(8)—C(12)	1.4037 (9)
O(3)—C(11)	1.3400 (8)	C(9)—C(10)	1.4613 (9)
O(3)—C(12)	1.3575 (7)	C(10)—C(11)	1.3589 (9)
O(4)—C(14)	1.3424 (8)	C(10)—C(15)	1.4903 (9)
O(5)—C(18)	1.3619 (8)	C(11)—H(10)	1.097 (9)
O(5)—C(21)	1.4283 (9)	C(12)—C(13)	1.3875 (9)
C(1)—C(3)	1.5235 (10)	C(13)—C(14)	1.3901 (9)
C(1)—H(1)	1.100 (10)	C(13)—H(11)	1.107 (8)
C(1)—H(2)	1.094 (10)	C(15)—C(16)	1.4041 (9)
C(1)—H(3)	1.072 (11)	C(15)—C(20)	1.3983 (9)
C(2)—C(3)	1.5238 (10)	C(16)—C(17)	1.3872 (9)
C(2)—H(4)	1.081 (10)	C(16)—H(12)	1.088 (8)
C(2)—H(5)	1.073 (10)	C(17)—C(18)	1.4019 (9)
C(2)—H(6)	1.076 (10)	C(17)—H(13)	1.088 (8)
C(3)—C(4)	1.5010 (10)	C(18)—C(19)	1.3955 (9)
C(4)—C(5)	1.3359 (10)	C(19)—C(20)	1.3952 (9)
C(4)—H(7)	1.076 (9)	C(19)—H(14)	1.085 (8)
C(5)—C(6)	1.4591 (9)	C(20)—H(15)	1.045 (8)
C(5)—H(8)	1.069 (9)	C(21)—H(16)	1.104 (10)
C(6)—C(7)	1.3935 (9)	C(21)—H(17)	1.082 (11)
C(6)—C(14)	1.4128 (9)	C(21)—H(18)	1.059 (9)
C(7)—O(1)—H(9)	104.8 (5)	C(11)—C(10)—C(15)	118.95 (6)
C(11)—O(3)—C(12)	119.77 (5)	O(3)—C(11)—C(10)	125.25 (6)
C(18)—O(5)—C(21)	117.49 (5)	O(3)—C(11)—H(10)	111.5 (4)
C(3)—C(1)—H(1)	109.7 (5)	C(10)—C(11)—H(10)	123.2 (4)
C(3)—C(1)—H(2)	111.0 (5)	O(3)—C(12)—C(8)	120.26 (6)
C(3)—C(1)—H(3)	109.06 (14)	O(3)—C(12)—C(13)	116.46 (6)
H(1)—C(1)—H(2)	108.5 (7)	C(8)—C(12)—C(13)	123.28 (6)
H(1)—C(1)—H(3)	108.5 (7)	C(12)—C(13)—C(14)	117.67 (6)
H(2)—C(1)—H(3)	109.5 (7)	C(12)—C(13)—H(11)	121.6 (4)
C(3)—C(2)—H(4)	109.3 (6)	C(14)—C(13)—H(11)	120.8 (4)
C(3)—C(2)—H(5)	109.1 (5)	O(4)—C(14)—C(6)	121.71 (6)
C(3)—C(2)—H(6)	108.9 (5)	O(4)—C(14)—C(13)	116.25 (6)
H(4)—C(2)—H(5)	109.4 (7)	C(6)—C(14)—C(13)	122.01 (6)
H(4)—C(2)—H(6)	108.6 (7)	C(10)—C(15)—C(16)	121.99 (6)
H(5)—C(2)—H(6)	111.5 (7)	C(10)—C(15)—C(20)	120.09 (6)
C(1)—C(3)—C(2)	112.05 (6)	C(16)—C(15)—C(20)	117.91 (6)
C(1)—C(3)—C(4)	110.97 (6)	C(15)—C(16)—C(17)	120.84 (6)
C(2)—C(3)—C(4)	110.70 (6)	C(15)—C(16)—H(12)	119.9 (4)
C(3)—C(4)—C(5)	123.25 (6)	C(17)—C(16)—H(12)	119.3 (4)
C(3)—C(4)—H(7)	116.4 (5)	C(16)—C(17)—C(18)	120.53 (6)
C(5)—C(4)—H(7)	120.3 (5)	C(16)—C(17)—H(13)	121.7 (4)
C(4)—C(5)—C(6)	120.03 (6)	C(18)—C(17)—H(13)	117.7 (4)
C(4)—C(5)—H(8)	124.2 (4)	O(5)—C(18)—C(17)	116.21 (6)
C(6)—C(5)—H(8)	115.7 (4)	O(5)—C(18)—C(19)	124.37 (6)
C(5)—C(6)—C(7)	123.03 (6)	C(17)—C(18)—C(19)	119.40 (6)
C(5)—C(6)—C(14)	118.20 (6)	C(18)—C(19)—C(20)	119.46 (6)
C(7)—C(6)—C(14)	118.77 (6)	C(18)—C(19)—H(14)	120.6 (4)
O(1)—C(7)—C(6)	118.94 (6)	C(20)—C(19)—H(14)	120.16 (12)
O(1)—C(7)—C(8)	120.19 (6)	C(15)—C(20)—C(19)	121.83 (6)
C(6)—C(7)—C(8)	120.88 (6)	C(15)—C(20)—H(15)	119.1 (4)
C(7)—C(8)—C(9)	121.83 (6)	C(19)—C(20)—H(15)	119.0 (4)
C(7)—C(8)—C(12)	117.36 (6)	O(5)—C(21)—H(16)	110.9 (5)
C(9)—C(8)—C(12)	120.77 (6)	O(5)—C(21)—H(17)	110.5 (5)
O(2)—C(9)—C(8)	121.36 (6)	O(5)—C(21)—H(18)	105.4 (5)
O(2)—C(9)—C(10)	122.82 (6)	H(16)—C(21)—H(17)	109.1 (7)
C(8)—C(9)—C(10)	115.82 (6)	H(16)—C(21)—H(18)	110.9 (7)
C(9)—C(10)—C(11)	118.09 (6)	H(17)—C(21)—H(18)	110.1 (7)
C(9)—C(10)—C(15)	122.96 (6)

(O,O-Dimethyl)

Crystal data

C22H20O5	F(000) = 768
Mr = 364.38	Dx = 1.356 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3689 reflections
a = 9.0604 (7) Å	θ = 2.2–31.6°
b = 19.0147 (14) Å	µ = 0.10 mm^−1
c = 10.5963 (8) Å	T = 90 K
β = 101.333 (2)°	Plate-like, colorless
V = 1789.9 (2) Å^3	0.15 × 0.12 × 0.08 mm
Z = 4

Data collection

CCD area detector diffractometer	8631 independent reflections
Radiation source: fine-focus sealed tube	5234 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.066
Detector resolution: 8.333 pixels mm^-1	θmax = 36.3°, θmin = 2.1°
phi and ω scans	h = −14→15
Absorption correction: empirical (using intensity measurements) SADABS by Sheldrick (Blessing, 1995)	k = −31→30
Tmin = 0.978, Tmax = 0.990	l = −17→17
29061 measured reflections

Refinement

Refinement on F	0 restraints
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.043	w1 = 1/[s^2(Fo)]
wR(F^2) = 0.028	(Δ/σ)max = 0.0004
S = 1.30	Δρmax = 0.29 e Å^−3
5234 reflections	Δρmin = −0.27 e Å^−3
324 parameters

Special details

Geometry. The positions of the H atoms atoms were freely refined using invariom database pseudoatom parameters up to hexadecapoles. This procedure yields bond distances in better agreement with standard neutron results.

As local atomic site symmetry was employed for the multipole parameters, a local atomic coordinate system was necessary for ensuring the correct orientation of the aspherical electron density. Dummy atoms were therefore necessary in some cases.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O(1)	0.68549 (7)	1.09157 (3)	−0.06942 (6)	0.019
O(2)	0.74664 (7)	0.91221 (3)	0.24714 (6)	0.018
O(3)	0.78319 (7)	0.77658 (3)	0.14572 (7)	0.021
O(4)	0.61429 (7)	0.85964 (3)	−0.20908 (6)	0.018
O(5)	0.75398 (7)	0.46379 (3)	−0.06885 (7)	0.021
C(1)	0.70470 (10)	1.21220 (10)	−0.02020 (10)	0.027
C(2)	0.93600 (10)	1.13610 (10)	0.00950 (10)	0.026
C(3)	0.77140 (10)	1.1408 (1)	0.02290 (10)	0.02
C(4)	0.75440 (10)	1.12290 (10)	0.15780 (10)	0.021
C(5)	0.73600 (10)	1.0561 (1)	0.19040 (10)	0.019
C(6)	0.71960 (10)	1.0009 (1)	0.09180 (10)	0.016
C(7)	0.71940 (10)	0.9296 (1)	0.12030 (10)	0.016
C(8)	0.62950 (10)	0.87510 (10)	0.29220 (10)	0.022
C(9)	0.69427 (9)	0.87807 (4)	0.02050 (9)	0.015
C(10)	0.72480 (10)	0.8024 (1)	0.04130 (10)	0.016
C(11)	0.68170 (10)	0.7591 (1)	−0.07530 (10)	0.016
C(12)	0.62730 (10)	0.7897 (1)	−0.18950 (10)	0.017
C(13)	0.65280 (10)	0.9036 (1)	−0.10590 (10)	0.016
C(14)	0.65090 (10)	0.9747 (1)	−0.13750 (10)	0.017
C(15)	0.69010 (10)	1.0227 (1)	−0.03810 (10)	0.016
C(16)	0.69650 (10)	0.6811 (1)	−0.06950 (10)	0.016
C(17)	0.83050 (10)	0.6490 (1)	−0.00690 (10)	0.019
C(18)	0.84690 (10)	0.5766 (1)	−0.00840 (10)	0.02
C(19)	0.72790 (10)	0.5344 (1)	−0.07190 (10)	0.018
C(20)	0.59380 (10)	0.5655 (1)	−0.13370 (10)	0.019
C(21)	0.57930 (10)	0.6385 (1)	−0.13190 (10)	0.018
C(22)	0.63370 (10)	0.41960 (10)	−0.12850 (10)	0.026
H(1)	0.7690 (10)	1.2540 (10)	0.0350 (10)	0.045 (4)
H(2)	0.7070 (10)	1.2230 (10)	−0.1210 (10)	0.047 (4)
H(3)	0.5890 (10)	1.2160 (10)	−0.0100 (10)	0.037 (4)
H(4)	1.0020 (10)	1.1720 (10)	0.0750 (10)	0.044 (4)
H(5)	0.9480 (10)	1.1490 (10)	−0.0900 (10)	0.049 (4)
H(6)	0.9780 (10)	1.0850 (10)	0.0340 (10)	0.034 (3)
H(7)	0.7660 (10)	1.1640 (10)	0.2270 (10)	0.035 (3)
H(8)	0.7270 (10)	1.0410 (10)	0.2860 (10)	0.027 (3)
H(9)	0.645 (2)	0.8790 (10)	0.393 (2)	0.058 (4)
H(10)	0.524 (2)	0.8970 (10)	0.259 (2)	0.084 (6)
H(11)	0.622 (2)	0.8250 (10)	0.264 (2)	0.091 (6)
H(12)	0.5910 (10)	0.7630 (10)	−0.2790 (10)	0.030 (3)
H(13)	0.6230 (10)	0.9910 (10)	−0.2350 (10)	0.028 (3)
H(14)	0.9230 (10)	0.6820 (10)	0.0420 (10)	0.030 (3)
H(15)	0.9500 (10)	0.5530 (10)	0.0370 (10)	0.030 (3)
H(19)	0.5070 (10)	0.5280 (10)	−0.1860 (10)	0.024 (3)
H(20)	0.4750 (10)	0.6620 (10)	−0.1790 (10)	0.027 (3)
H(16)	0.6770 (10)	0.3670 (10)	−0.1130 (10)	0.048 (4)
H(17)	0.6000 (10)	0.4310 (10)	−0.2300 (10)	0.032 (3)
H(18)	0.5380 (10)	0.4260 (10)	−0.0850 (10)	0.038 (4)
DUM1	0.77598	1.07194	0.05417	0	0
DUM2	0.6023	0.89248	0.16536	0	0
DUM3	0.63	0.7668	0.1778	0	0
DUM4	0.66587	0.83369	−0.08624	0	0
DUM5	0.60771	0.49025	−0.13154	0	0
DUM6	0.70651	1.07786	0.06044	0	0
DUM7	0.6779	0.95507	−0.00612	0	0
DUM8	0.71289	0.60871	−0.07092	0	0
DUM9	0.71153	0.60673	−0.07044	0	0
DUM10	0.71342	0.60734	−0.0701	0	0
DUM11	0.711	0.6081	−0.07125	0	0

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O(1)	0.0180 (3)	0.0193 (3)	0.0201 (4)	0.0004 (2)	0.0032 (3)	−0.0003 (3)
O(2)	0.0167 (3)	0.0233 (3)	0.0132 (3)	−0.0008 (3)	0.0006 (3)	−0.0021 (3)
O(3)	0.0275 (4)	0.0197 (3)	0.0136 (4)	0.0041 (3)	−0.0033 (3)	−0.0002 (3)
O(4)	0.0204 (4)	0.0202 (3)	0.0131 (4)	0.0010 (3)	0.0016 (3)	−0.0014 (3)
O(5)	0.0250 (4)	0.0201 (3)	0.0182 (4)	0.0048 (3)	0.0031 (3)	0.0016 (3)
C(1)	0.0246 (6)	0.0194 (5)	0.0352 (7)	−0.0005 (4)	0.0048 (5)	−0.0009 (5)
C(2)	0.0170 (5)	0.0322 (6)	0.0289 (7)	−0.0017 (4)	0.0063 (5)	0.0001 (5)
C(3)	0.0151 (5)	0.0193 (4)	0.0242 (6)	−0.0013 (3)	0.0043 (4)	−0.0023 (4)
C(4)	0.0198 (5)	0.0209 (5)	0.0221 (6)	−0.0019 (4)	0.0059 (4)	−0.0053 (4)
C(5)	0.0182 (5)	0.0213 (5)	0.0174 (5)	−0.0013 (4)	0.0048 (4)	−0.0065 (4)
C(6)	0.0136 (4)	0.0200 (4)	0.0146 (5)	0.0007 (3)	0.0031 (4)	−0.0025 (4)
C(7)	0.0132 (4)	0.0184 (4)	0.0143 (5)	0.0003 (3)	0.0022 (4)	−0.0020 (4)
C(8)	0.0212 (5)	0.0286 (6)	0.0159 (6)	−0.0005 (4)	0.0053 (5)	0.0026 (4)
C(9)	0.0135 (4)	0.0188 (4)	0.0119 (5)	0.0006 (3)	0.0014 (4)	−0.0013 (3)
C(10)	0.0144 (4)	0.0183 (4)	0.0132 (5)	0.0007 (3)	0.0014 (4)	−0.0016 (4)
C(11)	0.0156 (4)	0.0155 (4)	0.0148 (5)	0.0005 (3)	0.0016 (4)	−0.0020 (4)
C(12)	0.0189 (5)	0.0198 (5)	0.0125 (5)	0.0008 (4)	0.0003 (4)	−0.0011 (4)
C(13)	0.0147 (4)	0.0186 (4)	0.0127 (5)	0.0003 (3)	0.0021 (4)	−0.0007 (4)
C(14)	0.0178 (5)	0.0183 (4)	0.0145 (5)	0.0011 (3)	0.0034 (4)	0.0004 (4)
C(15)	0.0128 (4)	0.0194 (4)	0.0153 (5)	0.0005 (3)	0.0027 (4)	−0.0009 (4)
C(16)	0.0134 (4)	0.0172 (4)	0.0164 (5)	0.0022 (3)	0.0012 (4)	−0.0013 (4)
C(17)	0.0149 (5)	0.0221 (5)	0.0185 (5)	0.0031 (4)	−0.0007 (4)	−0.0029 (4)
C(18)	0.0181 (5)	0.0229 (5)	0.0169 (5)	0.0056 (4)	0.0001 (4)	−0.0014 (4)
C(19)	0.0192 (5)	0.0193 (4)	0.0140 (5)	0.0034 (4)	0.0031 (4)	0.0000 (4)
C(20)	0.0188 (5)	0.0170 (4)	0.0196 (5)	0.0005 (4)	0.0010 (4)	0.0007 (4)
C(21)	0.0146 (5)	0.0186 (4)	0.0184 (5)	0.0006 (3)	−0.0012 (4)	0.0005 (4)
C(22)	0.0281 (6)	0.0221 (5)	0.0264 (7)	0.0005 (4)	0.0086 (5)	0.0009 (4)

Geometric parameters (Å, º)

O(1)—C(15)	1.3498 (10)	C(8)—H(10)	1.035 (18)
O(2)—C(7)	1.3590 (11)	C(8)—H(11)	1.000 (17)
O(3)—C(10)	1.2312 (11)	C(9)—C(10)	1.4733 (12)
O(4)—C(12)	1.3469 (11)	C(9)—C(13)	1.4041 (13)
O(4)—C(13)	1.3661 (11)	C(10)—C(11)	1.4724 (13)
O(5)—C(19)	1.3623 (10)	C(11)—C(12)	1.3461 (13)
O(5)—C(22)	1.4217 (12)	C(11)—C(16)	1.490 (2)
C(1)—C(3)	1.5193 (13)	C(12)—H(12)	1.070 (12)
C(1)—H(1)	1.087 (13)	C(13)—C(14)	1.393 (2)
C(1)—H(2)	1.087 (15)	C(14)—C(15)	1.3852 (13)
C(1)—H(3)	1.082 (13)	C(14)—H(13)	1.055 (12)
C(2)—C(3)	1.5291 (14)	C(16)—C(17)	1.4033 (12)
C(2)—H(4)	1.074 (13)	C(16)—C(21)	1.3938 (12)
C(2)—H(5)	1.104 (15)	C(17)—C(18)	1.386 (2)
C(2)—H(6)	1.057 (12)	C(17)—H(14)	1.092 (11)
C(3)—C(4)	1.5064 (15)	C(18)—C(19)	1.4043 (13)
C(4)—C(5)	1.336 (2)	C(18)—H(15)	1.067 (11)
C(4)—H(7)	1.066 (12)	C(19)—C(20)	1.3936 (12)
C(5)—C(6)	1.4674 (13)	C(20)—C(21)	1.395 (2)
C(5)—H(8)	1.070 (12)	C(20)—H(19)	1.122 (10)
C(6)—C(7)	1.390 (2)	C(21)—H(20)	1.078 (11)
C(6)—C(15)	1.4119 (13)	C(22)—H(16)	1.072 (13)
C(7)—C(9)	1.4259 (12)	C(22)—H(17)	1.082 (13)
C(8)—H(9)	1.048 (17)	C(22)—H(18)	1.072 (14)
C(12)—O(4)—C(13)	118.67 (8)	C(10)—C(11)—C(16)	121.00 (8)
C(19)—O(5)—C(22)	117.20 (7)	C(12)—C(11)—C(16)	118.85 (9)
C(3)—C(1)—H(1)	110.9 (6)	O(4)—C(12)—C(11)	124.80 (9)
C(3)—C(1)—H(2)	111.9 (7)	O(4)—C(12)—H(12)	109.4 (6)
C(3)—C(1)—H(3)	111.6 (6)	C(11)—C(12)—H(12)	125.7 (6)
H(1)—C(1)—H(2)	106.3 (9)	O(4)—C(13)—C(9)	122.04 (8)
H(1)—C(1)—H(3)	108.7 (9)	O(4)—C(13)—C(14)	114.36 (8)
H(2)—C(1)—H(3)	107.2 (9)	C(9)—C(13)—C(14)	123.58 (9)
C(3)—C(2)—H(4)	109.2 (7)	C(13)—C(14)—C(15)	117.85 (9)
C(3)—C(2)—H(5)	110.9 (7)	C(13)—C(14)—H(13)	120.0 (6)
C(3)—C(2)—H(6)	109.9 (7)	C(15)—C(14)—H(13)	122.1 (6)
H(4)—C(2)—H(5)	109.3 (9)	O(1)—C(15)—C(6)	120.99 (8)
H(4)—C(2)—H(6)	107.7 (9)	O(1)—C(15)—C(14)	117.45 (9)
H(5)—C(2)—H(6)	109.9 (9)	C(6)—C(15)—C(14)	121.29 (8)
C(1)—C(3)—C(2)	111.26 (9)	C(11)—C(16)—C(17)	121.00 (8)
C(1)—C(3)—C(4)	112.27 (9)	C(11)—C(16)—C(21)	120.26 (8)
C(2)—C(3)—C(4)	110.96 (9)	C(17)—C(16)—C(21)	118.67 (8)
C(3)—C(4)—C(5)	120.16 (9)	C(16)—C(17)—C(18)	120.74 (9)
C(3)—C(4)—H(7)	117.8 (6)	C(16)—C(17)—H(14)	119.4 (6)
C(5)—C(4)—H(7)	121.9 (6)	C(18)—C(17)—H(14)	119.9 (6)
C(4)—C(5)—C(6)	119.71 (10)	C(17)—C(18)—C(19)	119.96 (9)
C(4)—C(5)—H(8)	122.6 (6)	C(17)—C(18)—H(15)	120.2 (6)
C(6)—C(5)—H(8)	117.7 (6)	C(19)—C(18)—H(15)	119.8 (6)
C(5)—C(6)—C(7)	123.19 (9)	O(5)—C(19)—C(18)	115.99 (8)
C(5)—C(6)—C(15)	117.27 (8)	O(5)—C(19)—C(20)	124.11 (8)
C(7)—C(6)—C(15)	119.31 (8)	C(18)—C(19)—C(20)	119.90 (8)
O(2)—C(7)—C(6)	116.34 (8)	C(19)—C(20)—C(21)	119.49 (9)
O(2)—C(7)—C(9)	122.57 (8)	C(19)—C(20)—H(19)	114.9 (5)
C(6)—C(7)—C(9)	121.08 (9)	C(21)—C(20)—H(19)	125.5 (5)
H(9)—C(8)—H(10)	104.2 (12)	C(16)—C(21)—C(20)	121.24 (9)
H(9)—C(8)—H(11)	111.3 (12)	C(16)—C(21)—H(20)	120.0 (5)
H(10)—C(8)—H(11)	106.3 (12)	C(20)—C(21)—H(20)	118.8 (5)
C(7)—C(9)—C(10)	124.18 (8)	O(5)—C(22)—H(16)	105.0 (7)
C(7)—C(9)—C(13)	116.33 (8)	O(5)—C(22)—H(17)	111.5 (6)
C(10)—C(9)—C(13)	119.14 (8)	O(5)—C(22)—H(18)	110.7 (6)
O(3)—C(10)—C(9)	123.97 (8)	H(16)—C(22)—H(17)	110.8 (9)
O(3)—C(10)—C(11)	121.84 (8)	H(16)—C(22)—H(18)	110.4 (9)
C(9)—C(10)—C(11)	114.19 (8)	H(17)—C(22)—H(18)	108.4 (9)
C(10)—C(11)—C(12)	120.15 (8)

(5-O-Dimethyl)

Crystal data

C52H52O10	F(000) = 1776
Mr = 836.94	Dx = 1.250 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 8567 reflections
a = 11.9602 (3) Å	θ = 2.3–35.4°
b = 18.6249 (5) Å	µ = 0.09 mm^−1
c = 19.9648 (5) Å	T = 120 K
V = 4447.3 (2) Å^3	Prismatic, colorless
Z = 4	0.31 × 0.30 × 0.21 mm

Data collection

CCD area detector diffractometer	10408 independent reflections
Radiation source: fine-focus sealed tube	8668 reflections with > 2σ(F)
Graphite monochromator	Rint = 0.063
phi and ω scans	θmax = 35.5°, θmin = 1.5°
Absorption correction: empirical (using intensity measurements) SADABS by Sheldrick (Blessing 1995)	h = −19→19
Tmin = 0.974, Tmax = 0.982	k = −30→30
114385 measured reflections	l = −28→32

Refinement

Refinement on F	0 restraints
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.029	w1 = 1/[s^2(Fo)]
wR(F^2) = 0.021	(Δ/σ)max = 0.0002
S = 1.59	Δρmax = 0.33 e Å^−3
8668 reflections	Δρmin = −0.18 e Å^−3
764 parameters

Special details

Geometry. The positions of the H atoms atoms were freely refined using invariom database pseudoatom parameters up to hexadecapoles. This procedure yields bond distances in better agreement with standard neutron results.

As local atomic site symmetry was employed for the multipole parameters, a local atomic coordinate system was necessary for ensuring the correct orientation of the aspherical electron density. Dummy atoms were therefore necessary in some cases.

The coordinates of atom O(1 A) were kept fixed to provide an origin for the space group.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O(1A)	−0.18082	0.1252	0.05613	0.028
O(2A)	−0.06297 (6)	0.19068 (4)	0.15913 (5)	0.028
O(3A)	0.02915 (6)	0.34507 (4)	0.02485 (5)	0.027
O(4A)	−0.18961 (7)	0.25760 (4)	−0.14854 (5)	0.031
O(5A)	0.18883 (6)	0.32327 (4)	0.40191 (5)	0.029
O(1B)	0.99170 (6)	0.52699 (4)	0.36400 (5)	0.026
O(2B)	0.87410 (7)	0.50555 (4)	0.24591 (5)	0.033
O(3B)	0.70955 (6)	0.34243 (4)	0.33975 (5)	0.023
O(4B)	0.89903 (6)	0.36799 (4)	0.54250 (5)	0.029
O(5B)	0.67082 (7)	0.44789 (4)	−0.03743 (5)	0.032
C(1A)	−0.13790 (10)	0.16530 (10)	−0.22530 (10)	0.048
C(2A)	−0.3200 (2)	0.23230 (10)	−0.23360 (10)	0.069
C(3A)	−0.23660 (10)	0.19800 (10)	−0.18610 (10)	0.033
C(4A)	−0.28780 (10)	0.14230 (10)	−0.14140 (10)	0.035
C(5A)	−0.26105 (9)	0.13652 (7)	−0.07672 (7)	0.033
C(6A)	−0.18224 (8)	0.18739 (6)	−0.04674 (6)	0.025
C(7A)	−0.14313 (8)	0.18183 (5)	0.01861 (6)	0.023
C(8A)	−0.09850 (10)	0.07140 (10)	0.07000 (10)	0.033
C(9A)	−0.07122 (8)	0.23485 (5)	0.04695 (6)	0.02
C(10A)	−0.03685 (8)	0.23669 (5)	0.11778 (6)	0.021
C(11A)	0.03224 (8)	0.29874 (5)	0.13619 (6)	0.02
C(12A)	0.06065 (9)	0.34754 (6)	0.08950 (6)	0.024
C(13A)	−0.03898 (8)	0.29106 (5)	0.00410 (6)	0.022
C(14A)	−0.07480 (9)	0.29748 (6)	−0.06211 (6)	0.025
C(15A)	−0.14769 (8)	0.24626 (6)	−0.08657 (6)	0.025
C(16A)	0.07430 (8)	0.30722 (5)	0.20576 (6)	0.02
C(17A)	0.00388 (8)	0.29595 (5)	0.26112 (6)	0.022
C(18A)	0.04454 (8)	0.30276 (5)	0.32565 (6)	0.023
C(19A)	0.15701 (8)	0.32039 (5)	0.33661 (6)	0.023
C(20A)	0.22756 (9)	0.33279 (6)	0.28205 (6)	0.023
C(21A)	0.18550 (8)	0.32614 (5)	0.21709 (6)	0.021
C(22A)	0.30120 (10)	0.34290 (10)	0.41640 (10)	0.029
C(23A)	0.31360 (10)	0.33710 (10)	0.49060 (10)	0.03
C(24A)	0.40740 (10)	0.32470 (10)	0.52410 (10)	0.032
C(25A)	0.4077 (2)	0.32300 (10)	0.59920 (10)	0.046
C(26A)	0.51930 (10)	0.31320 (10)	0.49210 (10)	0.054
C(1B)	0.9941 (2)	0.37090 (10)	0.64650 (10)	0.047
C(2B)	0.84230 (10)	0.45950 (10)	0.62030 (10)	0.042
C(3B)	0.94210 (10)	0.41780 (10)	0.59270 (10)	0.029
C(4B)	1.02682 (9)	0.46809 (6)	0.56291 (7)	0.03
C(5B)	1.02819 (9)	0.48351 (6)	0.49754 (7)	0.028
C(6B)	0.94540 (8)	0.45005 (5)	0.45326 (6)	0.022
C(7B)	0.92961 (8)	0.47054 (5)	0.38697 (6)	0.021
C(8B)	1.08600 (10)	0.50720 (10)	0.32400 (10)	0.036
C(9B)	0.84952 (8)	0.43614 (5)	0.34508 (6)	0.019
C(10B)	0.82822 (8)	0.45517 (5)	0.27458 (6)	0.021
C(11B)	0.74724 (8)	0.40859 (5)	0.23991 (6)	0.019
C(12B)	0.69248 (8)	0.35727 (5)	0.27443 (6)	0.021
C(13B)	0.78900 (8)	0.37955 (5)	0.37423 (6)	0.019
C(14B)	0.80436 (8)	0.35673 (6)	0.44023 (6)	0.023
C(15B)	0.88177 (8)	0.39265 (6)	0.47935 (6)	0.023
C(16B)	0.72582 (8)	0.41719 (5)	0.16706 (6)	0.019
C(17B)	0.70572 (8)	0.48509 (5)	0.13898 (6)	0.023
C(18B)	0.68614 (9)	0.49260 (6)	0.07104 (6)	0.025
C(19B)	0.68653 (8)	0.43282 (6)	0.02881 (6)	0.022
C(20B)	0.70414 (8)	0.36457 (6)	0.05586 (6)	0.023
C(21B)	0.72411 (8)	0.35762 (5)	0.12445 (6)	0.021
C(22B)	0.63680 (10)	0.39130 (10)	−0.08140 (10)	0.029
C(23B)	0.63172 (9)	0.42070 (7)	−0.15122 (6)	0.03
C(24B)	0.56025 (9)	0.47010 (6)	−0.17346 (6)	0.031
C(25B)	0.56280 (10)	0.49630 (10)	−0.24450 (10)	0.048
C(26B)	0.47090 (10)	0.50330 (10)	−0.13040 (10)	0.043
H(1A)	−0.106 (2)	0.2070 (10)	−0.2600 (10)	0.073 (6)
H(2A)	−0.183 (2)	0.1280 (10)	−0.2530 (10)	0.068 (5)
H(3A)	−0.074 (2)	0.1380 (10)	−0.1890 (10)	0.082 (6)
H(4A)	−0.3780 (10)	0.2470 (10)	−0.1970 (10)	0.038 (4)
H(5A)	−0.352 (2)	0.1850 (10)	−0.2620 (10)	0.101 (7)
H(6A)	−0.281 (2)	0.2810 (10)	−0.2620 (10)	0.099 (7)
H(7A)	−0.3440 (10)	0.1090 (10)	−0.1630 (10)	0.052 (4)
H(8A)	−0.2940 (10)	0.0950 (10)	−0.0460 (10)	0.048 (4)
H(9A)	−0.089 (2)	0.0420 (10)	0.0300 (10)	0.068 (5)
H(10A)	−0.130 (2)	0.0410 (10)	0.1050 (10)	0.077 (6)
H(11A)	−0.022 (2)	0.0920 (10)	0.0810 (10)	0.063 (5)
H(12A)	0.1120 (10)	0.3930 (10)	0.1010 (10)	0.038 (4)
H(13A)	−0.0490 (10)	0.3420 (10)	−0.0920 (10)	0.029 (3)
H(14A)	−0.0800 (10)	0.2820 (10)	0.2540 (10)	0.029 (3)
H(15A)	−0.0050 (10)	0.2930 (10)	0.3680 (10)	0.035 (3)
H(16A)	0.3130 (10)	0.3470 (10)	0.2890 (10)	0.036 (4)
H(17A)	0.2420 (10)	0.3340 (10)	0.1790 (10)	0.035 (3)
H(18A)	0.3110 (10)	0.3990 (10)	0.4000 (10)	0.050 (4)
H(19A)	0.3590 (10)	0.3080 (10)	0.3910 (10)	0.046 (4)
H(20A)	0.2380 (10)	0.3450 (10)	0.5180 (10)	0.046 (4)
H(21A)	0.457 (2)	0.3630 (10)	0.6190 (10)	0.082 (7)
H(22A)	0.441 (2)	0.276 (2)	0.6160 (10)	0.098 (7)
H(23A)	0.323 (2)	0.3280 (10)	0.6150 (10)	0.066 (6)
H(24A)	0.5210 (10)	0.3130 (10)	0.4380 (10)	0.057 (5)
H(25A)	0.549 (2)	0.2630 (10)	0.5030 (10)	0.082 (7)
H(26A)	0.577 (2)	0.3510 (10)	0.5110 (10)	0.084 (7)
H(1B)	0.9310 (10)	0.3330 (10)	0.6700 (10)	0.058 (5)
H(2B)	1.0210 (10)	0.4070 (10)	0.6820 (10)	0.061 (5)
H(3B)	1.058 (2)	0.3410 (10)	0.6230 (10)	0.061 (5)
H(4B)	0.8100 (10)	0.4910 (10)	0.5810 (10)	0.055 (5)
H(5B)	0.868 (2)	0.4970 (10)	0.6580 (10)	0.060 (5)
H(6B)	0.7810 (10)	0.4240 (10)	0.6410 (10)	0.051 (4)
H(7B)	1.0860 (10)	0.4930 (10)	0.5990 (10)	0.047 (4)
H(8B)	1.0860 (10)	0.5220 (10)	0.4760 (10)	0.043 (4)
H(9B)	1.147 (2)	0.4850 (10)	0.3570 (10)	0.056 (5)
H(10B)	1.111 (2)	0.5520 (10)	0.3030 (10)	0.069 (5)
H(11B)	1.0660 (10)	0.4680 (10)	0.2900 (10)	0.060 (5)
H(12B)	0.6320 (10)	0.3240 (10)	0.2520 (10)	0.033 (3)
H(13B)	0.7570 (10)	0.3140 (10)	0.4590 (10)	0.043 (4)
H(14B)	0.7070 (10)	0.5340 (10)	0.1710 (10)	0.031 (3)
H(15B)	0.6710 (10)	0.5440 (10)	0.0500 (10)	0.037 (3)
H(16B)	0.7030 (10)	0.3200 (10)	0.0230 (10)	0.033 (3)
H(17B)	0.7420 (10)	0.3040 (10)	0.1440 (10)	0.031 (3)
H(18B)	0.5530 (10)	0.3720 (10)	−0.0620 (10)	0.047 (4)
H(19B)	0.6960 (10)	0.3480 (10)	−0.0790 (10)	0.058 (5)
H(20B)	0.6900 (10)	0.4020 (10)	−0.1880 (10)	0.052 (4)
H(21B)	0.629 (2)	0.4730 (10)	−0.2720 (10)	0.065 (5)
H(22B)	0.573 (2)	0.5540 (10)	−0.2470 (10)	0.082 (6)
H(23B)	0.487 (2)	0.4860 (10)	−0.2680 (10)	0.074 (6)
H(24B)	0.468 (2)	0.4860 (10)	−0.0820 (10)	0.088 (7)
H(25B)	0.384 (2)	0.4910 (10)	−0.1530 (10)	0.079 (6)
H(26B)	0.478 (2)	0.5600 (10)	−0.1270 (10)	0.090 (7)
DUM1	−0.06074	0.12803	0.03244	0	0
DUM2	0.04066	0.14875	0.14203	0	0
DUM3	−0.00743	0.29356	0.06871	0	0
DUM4	−0.19461	0.18657	−0.12423	0	0
DUM5	0.26946	0.34002	0.35105	0	0
DUM6	1.02394	0.45076	0.34701	0	0
DUM7	0.96755	0.45628	0.22414	0	0
DUM8	0.77185	0.39434	0.30888	0	0
DUM9	0.92486	0.4425	0.5295	0	0
DUM10	0.65251	0.37621	−0.01518	0	0
DUM11	−0.22652	0.19539	−0.11658	0	0
DUM12	−0.1108	0.23812	−0.02422	0	0
DUM13	0.11499	0.31402	0.27033	0	0
DUM14	0.11638	0.31359	0.27204	0	0
DUM15	0.11496	0.31373	0.27161	0	0
DUM16	0.11641	0.31389	0.27076	0	0
DUM17	0.9646	0.42612	0.52361	0	0
DUM18	0.86899	0.41393	0.41605	0	0
DUM19	0.70621	0.42474	0.09902	0	0
DUM20	0.70607	0.4253	0.09671	0	0
DUM21	0.70645	0.42586	0.09736	0	0
DUM22	0.70583	0.42418	0.09837	0	0

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O(1A)	0.0228 (4)	0.0264 (4)	0.0349 (4)	−0.0074 (3)	0.0052 (3)	−0.0028 (3)
O(2A)	0.0311 (4)	0.0257 (4)	0.0280 (4)	−0.0090 (3)	0.0035 (3)	0.0032 (3)
O(3A)	0.0310 (4)	0.0223 (4)	0.0264 (3)	−0.0075 (3)	−0.0044 (3)	0.0024 (3)
O(4A)	0.0336 (4)	0.0327 (4)	0.0278 (4)	−0.0023 (3)	−0.0051 (3)	−0.0065 (3)
O(5A)	0.0302 (4)	0.0325 (4)	0.0236 (3)	−0.0039 (3)	0.0009 (3)	−0.0036 (3)
O(1B)	0.0247 (3)	0.0202 (4)	0.0328 (4)	−0.0053 (3)	−0.0031 (3)	0.0013 (3)
O(2B)	0.0404 (4)	0.0305 (4)	0.0290 (4)	−0.0187 (3)	−0.0072 (3)	0.0102 (3)
O(3B)	0.0255 (3)	0.0219 (3)	0.0218 (3)	−0.0066 (3)	0.0004 (3)	0.0006 (3)
O(4B)	0.0358 (4)	0.0262 (4)	0.0253 (3)	−0.0036 (3)	−0.0082 (3)	0.0017 (3)
O(5B)	0.0423 (5)	0.0299 (4)	0.0229 (3)	−0.0047 (3)	−0.0060 (3)	−0.0001 (3)
C(1A)	0.0740 (10)	0.0380 (10)	0.0340 (10)	0.0020 (10)	0.0140 (10)	−0.0070 (10)
C(2A)	0.0740 (10)	0.0460 (10)	0.0860 (10)	0.0040 (10)	−0.0530 (10)	−0.0080 (10)
C(3A)	0.0387 (6)	0.0303 (6)	0.0312 (5)	0.0047 (5)	−0.0124 (5)	−0.0103 (4)
C(4A)	0.0298 (6)	0.0377 (7)	0.0390 (6)	−0.0074 (5)	−0.0024 (5)	−0.0159 (5)
C(5A)	0.0273 (5)	0.0358 (6)	0.0363 (6)	−0.0118 (5)	0.0031 (5)	−0.0140 (5)
C(6A)	0.0202 (5)	0.0252 (5)	0.0283 (5)	−0.0031 (4)	0.0016 (4)	−0.0078 (4)
C(7A)	0.0180 (4)	0.0221 (5)	0.0280 (5)	−0.0029 (4)	0.0027 (4)	−0.0048 (4)
C(8A)	0.0358 (7)	0.0226 (5)	0.0401 (6)	−0.0045 (5)	0.0058 (5)	0.0012 (5)
C(9A)	0.0182 (4)	0.0182 (5)	0.0250 (4)	−0.0019 (3)	0.0012 (3)	−0.0014 (3)
C(10A)	0.0188 (4)	0.0198 (5)	0.0253 (5)	−0.0015 (3)	0.0023 (4)	−0.0008 (4)
C(11A)	0.0195 (4)	0.0196 (5)	0.0204 (4)	−0.0009 (3)	−0.0011 (3)	−0.0007 (3)
C(12A)	0.0278 (5)	0.0197 (5)	0.0250 (5)	−0.0059 (4)	−0.0031 (4)	0.0020 (4)
C(13A)	0.0220 (4)	0.0197 (5)	0.0242 (5)	−0.0022 (4)	−0.0013 (4)	−0.0004 (4)
C(14A)	0.0273 (5)	0.0243 (5)	0.0238 (5)	−0.0026 (4)	−0.0027 (4)	−0.0022 (4)
C(15A)	0.0229 (5)	0.0250 (5)	0.0264 (5)	−0.0010 (4)	−0.0002 (4)	−0.0059 (4)
C(16A)	0.0172 (4)	0.0203 (5)	0.0216 (4)	0.0007 (3)	0.0007 (3)	−0.0008 (3)
C(17A)	0.0166 (4)	0.0246 (5)	0.0258 (5)	0.0020 (4)	0.0026 (4)	−0.0004 (4)
C(18A)	0.0214 (5)	0.0252 (5)	0.0234 (5)	0.0018 (4)	0.0046 (4)	−0.0006 (4)
C(19A)	0.0229 (5)	0.0218 (5)	0.0229 (4)	−0.0002 (4)	0.0018 (4)	−0.0020 (4)
C(20A)	0.0213 (5)	0.0259 (5)	0.0226 (5)	−0.0027 (4)	0.0011 (4)	−0.0016 (4)
C(21A)	0.0188 (4)	0.0226 (5)	0.0228 (4)	−0.0013 (4)	0.0017 (4)	−0.0010 (4)
C(22A)	0.0321 (6)	0.0326 (6)	0.0233 (5)	−0.0025 (5)	−0.0027 (4)	−0.0033 (4)
C(23A)	0.0372 (6)	0.0310 (6)	0.0221 (5)	−0.0004 (5)	−0.0007 (4)	−0.0066 (4)
C(24A)	0.0464 (7)	0.0263 (5)	0.0242 (5)	0.0069 (5)	−0.0025 (5)	−0.0024 (4)
C(25A)	0.0730 (10)	0.0420 (10)	0.0240 (10)	0.0130 (10)	−0.0080 (10)	−0.0010 (10)
C(26A)	0.0452 (8)	0.0798 (12)	0.0365 (7)	0.0199 (8)	−0.0071 (6)	−0.0104 (8)
C(1B)	0.0750 (10)	0.0290 (10)	0.0370 (10)	0.0010 (10)	−0.0290 (10)	0.0000 (10)
C(2B)	0.0494 (8)	0.0339 (7)	0.0416 (7)	0.0005 (6)	0.0107 (6)	−0.0024 (6)
C(3B)	0.0395 (6)	0.0237 (5)	0.0251 (5)	0.0021 (5)	−0.0095 (4)	−0.0013 (4)
C(4B)	0.0306 (6)	0.0300 (6)	0.0304 (5)	−0.0010 (4)	−0.0105 (4)	−0.0057 (4)
C(5B)	0.0239 (5)	0.0282 (6)	0.0313 (5)	−0.0041 (4)	−0.0081 (4)	−0.0045 (4)
C(6B)	0.0194 (4)	0.0202 (5)	0.0268 (5)	−0.0013 (4)	−0.0045 (4)	−0.0016 (4)
C(7B)	0.0192 (4)	0.0177 (4)	0.0246 (5)	−0.0020 (4)	−0.0025 (3)	−0.0008 (4)
C(8B)	0.0257 (6)	0.0338 (7)	0.0489 (7)	−0.0056 (5)	0.0051 (5)	0.0076 (6)
C(9B)	0.0188 (4)	0.0156 (4)	0.0220 (4)	−0.0021 (3)	−0.0009 (3)	0.0009 (3)
C(10B)	0.0222 (4)	0.0182 (4)	0.0222 (4)	−0.0048 (4)	−0.0018 (3)	0.0021 (3)
C(11B)	0.0211 (4)	0.0186 (4)	0.0173 (4)	−0.0014 (3)	−0.0010 (3)	0.0004 (3)
C(12B)	0.0223 (5)	0.0194 (4)	0.0216 (4)	−0.0062 (4)	−0.0003 (4)	−0.0006 (3)
C(13B)	0.0205 (4)	0.0182 (4)	0.0195 (4)	−0.0029 (3)	−0.0003 (3)	0.0002 (3)
C(14B)	0.0253 (5)	0.0218 (5)	0.0209 (4)	−0.0047 (4)	−0.0016 (4)	0.0014 (4)
C(15B)	0.0236 (5)	0.0214 (5)	0.0231 (4)	−0.0015 (4)	−0.0032 (4)	0.0003 (4)
C(16B)	0.0201 (4)	0.0174 (4)	0.0192 (4)	0.0003 (3)	−0.0006 (3)	0.0004 (3)
C(17B)	0.0288 (5)	0.0171 (5)	0.0223 (4)	0.0012 (4)	−0.0017 (4)	−0.0006 (4)
C(18B)	0.0328 (5)	0.0188 (5)	0.0236 (5)	0.0006 (4)	−0.0043 (4)	0.0005 (4)
C(19B)	0.0236 (4)	0.0218 (5)	0.0210 (4)	−0.0001 (4)	−0.0017 (4)	−0.0008 (4)
C(20B)	0.0252 (5)	0.0204 (5)	0.0220 (4)	0.0022 (4)	−0.0001 (4)	−0.0030 (4)
C(21B)	0.0239 (5)	0.0182 (5)	0.0217 (4)	0.0016 (4)	−0.0001 (3)	−0.0007 (4)
C(22B)	0.0343 (6)	0.0299 (6)	0.0242 (5)	0.0057 (5)	−0.0051 (4)	−0.0039 (4)
C(23B)	0.0272 (5)	0.0404 (6)	0.0225 (5)	0.0026 (5)	−0.0024 (4)	−0.0040 (4)
C(24B)	0.0302 (6)	0.0373 (6)	0.0252 (5)	−0.0037 (5)	−0.0040 (4)	0.0024 (4)
C(25B)	0.0554 (9)	0.0576 (10)	0.0296 (6)	−0.0130 (8)	−0.0124 (6)	0.0112 (6)
C(26B)	0.0399 (8)	0.0447 (8)	0.0449 (8)	0.0135 (6)	−0.0015 (6)	0.0042 (6)

Geometric parameters (Å, º)

O(1A)—C(7A)	1.3700 (11)	C(25A)—H(21A)	1.03 (2)
O(2A)—C(10A)	1.2301 (12)	C(25A)—H(22A)	1.03 (3)
O(3A)—C(12A)	1.3454 (12)	C(25A)—H(23A)	1.07 (2)
O(3A)—C(13A)	1.3593 (12)	C(26A)—H(24A)	1.073 (18)
O(4A)—C(15A)	1.3515 (12)	C(26A)—H(25A)	1.02 (2)
O(5A)—C(19A)	1.3592 (12)	C(26A)—H(26A)	1.06 (2)
O(5A)—C(22A)	1.4228 (14)	C(1B)—C(3B)	1.5176 (16)
O(1B)—C(7B)	1.3665 (12)	C(1B)—H(1B)	1.132 (19)
O(2B)—C(10B)	1.2285 (12)	C(1B)—H(2B)	1.030 (19)
O(3B)—C(12B)	1.3486 (11)	C(1B)—H(3B)	1.05 (2)
O(3B)—C(13B)	1.3620 (11)	C(2B)—C(3B)	1.5277 (18)
O(4B)—C(15B)	1.3578 (12)	C(2B)—H(4B)	1.060 (18)
O(5B)—C(19B)	1.3649 (11)	C(2B)—H(5B)	1.081 (19)
C(1A)—H(1A)	1.11 (2)	C(2B)—H(6B)	1.072 (19)
C(1A)—H(2A)	1.03 (2)	C(3B)—C(4B)	1.5019 (17)
C(1A)—H(3A)	1.17 (2)	C(4B)—C(5B)	1.3364 (16)
C(2A)—C(3A)	1.5172 (19)	C(4B)—H(7B)	1.119 (16)
C(2A)—H(4A)	1.038 (16)	C(5B)—C(6B)	1.4664 (14)
C(2A)—H(5A)	1.12 (3)	C(5B)—H(8B)	1.087 (16)
C(2A)—H(6A)	1.17 (3)	C(6B)—C(7B)	1.3902 (14)
C(3A)—C(4A)	1.4997 (18)	C(6B)—C(15B)	1.4119 (14)
C(4A)—C(5A)	1.3348 (18)	C(7B)—C(9B)	1.4239 (13)
C(4A)—H(7A)	1.009 (17)	C(8B)—H(9B)	1.072 (18)
C(5A)—C(6A)	1.4645 (15)	C(8B)—H(10B)	0.98 (2)
C(5A)—H(8A)	1.057 (17)	C(8B)—H(11B)	1.03 (2)
C(6A)—C(7A)	1.3900 (14)	C(9B)—C(10B)	1.4737 (13)
C(6A)—C(15A)	1.4160 (15)	C(9B)—C(13B)	1.4048 (13)
C(7A)—C(9A)	1.4264 (13)	C(10B)—C(11B)	1.4730 (13)
C(8A)—H(9A)	0.97 (2)	C(11B)—C(12B)	1.3482 (13)
C(8A)—H(10A)	0.98 (2)	C(11B)—C(16B)	1.4854 (13)
C(8A)—H(11A)	1.03 (2)	C(12B)—H(12B)	1.053 (14)
C(9A)—C(10A)	1.4730 (14)	C(13B)—C(14B)	1.3967 (13)
C(9A)—C(13A)	1.4059 (14)	C(14B)—C(15B)	1.3838 (14)
C(10A)—C(11A)	1.4674 (14)	C(14B)—H(13B)	1.051 (16)
C(11A)—C(12A)	1.3456 (14)	C(16B)—C(17B)	1.4040 (14)
C(11A)—C(16A)	1.4857 (13)	C(16B)—C(21B)	1.3983 (13)
C(12A)—H(12A)	1.072 (16)	C(17B)—C(18B)	1.3836 (14)
C(13A)—C(14A)	1.3946 (14)	C(17B)—H(14B)	1.110 (14)
C(14A)—C(15A)	1.3816 (15)	C(18B)—C(19B)	1.3966 (14)
C(14A)—H(13A)	1.071 (14)	C(18B)—H(15B)	1.065 (15)
C(16A)—C(17A)	1.4055 (13)	C(19B)—C(20B)	1.3971 (14)
C(16A)—C(21A)	1.3943 (13)	C(20B)—C(21B)	1.3961 (14)
C(17A)—C(18A)	1.3827 (14)	C(20B)—H(16B)	1.058 (15)
C(17A)—H(14A)	1.044 (14)	C(21B)—H(17B)	1.097 (15)
C(18A)—C(19A)	1.4018 (14)	C(22B)—C(23B)	1.4993 (16)
C(18A)—H(15A)	1.052 (14)	C(22B)—H(18B)	1.129 (16)
C(19A)—C(20A)	1.3971 (14)	C(22B)—H(19B)	1.073 (19)
C(20A)—C(21A)	1.3966 (14)	C(23B)—C(24B)	1.3320 (16)
C(20A)—H(16A)	1.067 (15)	C(23B)—H(20B)	1.068 (17)
C(21A)—H(17A)	1.023 (14)	C(24B)—C(25B)	1.5009 (17)
C(22A)—C(23A)	1.4919 (15)	C(24B)—C(26B)	1.5047 (18)
C(22A)—H(18A)	1.094 (18)	C(25B)—H(21B)	1.06 (2)
C(22A)—H(19A)	1.070 (17)	C(25B)—H(22B)	1.08 (2)
C(23A)—C(24A)	1.3268 (17)	C(25B)—H(23B)	1.05 (2)
C(23A)—H(20A)	1.071 (16)	C(26B)—H(24B)	1.01 (2)
C(24A)—C(25A)	1.5002 (16)	C(26B)—H(25B)	1.15 (2)
C(24A)—C(26A)	1.498 (2)	C(26B)—H(26B)	1.06 (2)
C(12A)—O(3A)—C(13A)	119.04 (8)	C(3B)—C(1B)—H(1B)	112.1 (9)
C(19A)—O(5A)—C(22A)	118.03 (8)	C(3B)—C(1B)—H(2B)	103.6 (10)
C(12B)—O(3B)—C(13B)	119.36 (8)	C(3B)—C(1B)—H(3B)	106.8 (10)
H(1A)—C(1A)—H(2A)	108.2 (15)	H(1B)—C(1B)—H(2B)	109.7 (13)
H(1A)—C(1A)—H(3A)	117.7 (14)	H(1B)—C(1B)—H(3B)	109.9 (14)
H(2A)—C(1A)—H(3A)	112.6 (15)	H(2B)—C(1B)—H(3B)	114.6 (14)
C(3A)—C(2A)—H(4A)	96.3 (9)	C(3B)—C(2B)—H(4B)	107.3 (9)
C(3A)—C(2A)—H(5A)	102.1 (12)	C(3B)—C(2B)—H(5B)	111.5 (10)
C(3A)—C(2A)—H(6A)	111.4 (11)	C(3B)—C(2B)—H(6B)	110.8 (9)
H(4A)—C(2A)—H(5A)	109.1 (15)	H(4B)—C(2B)—H(5B)	106.0 (14)
H(4A)—C(2A)—H(6A)	113.7 (15)	H(4B)—C(2B)—H(6B)	112.2 (12)
H(5A)—C(2A)—H(6A)	120.8 (17)	H(5B)—C(2B)—H(6B)	108.9 (13)
C(2A)—C(3A)—C(4A)	113.20 (13)	C(1B)—C(3B)—C(2B)	110.91 (11)
C(3A)—C(4A)—C(5A)	122.26 (11)	C(1B)—C(3B)—C(4B)	111.29 (11)
C(3A)—C(4A)—H(7A)	116.5 (9)	C(2B)—C(3B)—C(4B)	110.64 (10)
C(5A)—C(4A)—H(7A)	121.3 (9)	C(3B)—C(4B)—C(5B)	121.90 (10)
C(4A)—C(5A)—C(6A)	119.85 (12)	C(3B)—C(4B)—H(7B)	115.7 (8)
C(4A)—C(5A)—H(8A)	121.4 (8)	C(5B)—C(4B)—H(7B)	122.4 (8)
C(6A)—C(5A)—H(8A)	118.7 (8)	C(4B)—C(5B)—C(6B)	119.29 (10)
C(5A)—C(6A)—C(7A)	123.51 (10)	C(4B)—C(5B)—H(8B)	122.1 (7)
C(5A)—C(6A)—C(15A)	117.34 (10)	C(6B)—C(5B)—H(8B)	118.6 (7)
C(7A)—C(6A)—C(15A)	119.12 (9)	C(5B)—C(6B)—C(7B)	123.31 (9)
O(1A)—C(7A)—C(6A)	117.38 (8)	C(5B)—C(6B)—C(15B)	117.60 (9)
O(1A)—C(7A)—C(9A)	120.96 (8)	C(7B)—C(6B)—C(15B)	119.06 (9)
C(6A)—C(7A)—C(9A)	121.58 (9)	O(1B)—C(7B)—C(6B)	117.18 (8)
H(9A)—C(8A)—H(10A)	108.1 (16)	O(1B)—C(7B)—C(9B)	120.97 (8)
H(9A)—C(8A)—H(11A)	106.9 (14)	C(6B)—C(7B)—C(9B)	121.81 (9)
H(10A)—C(8A)—H(11A)	113.7 (15)	H(9B)—C(8B)—H(10B)	112.9 (14)
C(7A)—C(9A)—C(10A)	124.41 (9)	H(9B)—C(8B)—H(11B)	107.0 (13)
C(7A)—C(9A)—C(13A)	116.06 (8)	H(10B)—C(8B)—H(11B)	113.2 (14)
C(10A)—C(9A)—C(13A)	119.36 (8)	C(7B)—C(9B)—C(10B)	124.69 (8)
O(2A)—C(10A)—C(9A)	123.86 (9)	C(7B)—C(9B)—C(13B)	116.16 (8)
O(2A)—C(10A)—C(11A)	121.57 (9)	C(10B)—C(9B)—C(13B)	119.15 (8)
C(9A)—C(10A)—C(11A)	114.57 (8)	O(2B)—C(10B)—C(9B)	123.47 (9)
C(10A)—C(11A)—C(12A)	120.05 (9)	O(2B)—C(10B)—C(11B)	121.64 (9)
C(10A)—C(11A)—C(16A)	120.56 (8)	C(9B)—C(10B)—C(11B)	114.89 (8)
C(12A)—C(11A)—C(16A)	119.36 (9)	C(10B)—C(11B)—C(12B)	119.78 (8)
O(3A)—C(12A)—C(11A)	124.81 (9)	C(10B)—C(11B)—C(16B)	120.66 (8)
O(3A)—C(12A)—H(12A)	113.3 (7)	C(12B)—C(11B)—C(16B)	119.55 (8)
C(11A)—C(12A)—H(12A)	121.9 (7)	O(3B)—C(12B)—C(11B)	124.48 (9)
O(3A)—C(13A)—C(9A)	122.01 (8)	O(3B)—C(12B)—H(12B)	112.8 (7)
O(3A)—C(13A)—C(14A)	114.17 (9)	C(11B)—C(12B)—H(12B)	122.7 (7)
C(9A)—C(13A)—C(14A)	123.81 (9)	O(3B)—C(13B)—C(9B)	122.07 (8)
C(13A)—C(14A)—C(15A)	118.02 (10)	O(3B)—C(13B)—C(14B)	114.47 (8)
C(13A)—C(14A)—H(13A)	120.0 (7)	C(9B)—C(13B)—C(14B)	123.46 (9)
C(15A)—C(14A)—H(13A)	121.9 (7)	C(13B)—C(14B)—C(15B)	118.25 (9)
O(4A)—C(15A)—C(6A)	121.80 (9)	C(13B)—C(14B)—H(13B)	120.4 (8)
O(4A)—C(15A)—C(14A)	116.73 (10)	C(15B)—C(14B)—H(13B)	121.4 (8)
C(6A)—C(15A)—C(14A)	121.34 (10)	O(4B)—C(15B)—C(6B)	121.12 (9)
C(11A)—C(16A)—C(17A)	121.10 (8)	O(4B)—C(15B)—C(14B)	117.53 (9)
C(11A)—C(16A)—C(21A)	120.10 (8)	C(6B)—C(15B)—C(14B)	121.24 (9)
C(17A)—C(16A)—C(21A)	118.80 (8)	C(11B)—C(16B)—C(17B)	121.16 (8)
C(16A)—C(17A)—C(18A)	120.55 (9)	C(11B)—C(16B)—C(21B)	120.85 (8)
C(16A)—C(17A)—H(14A)	119.8 (7)	C(17B)—C(16B)—C(21B)	117.99 (8)
C(18A)—C(17A)—H(14A)	119.6 (7)	C(16B)—C(17B)—C(18B)	120.76 (9)
C(17A)—C(18A)—C(19A)	120.29 (9)	C(16B)—C(17B)—H(14B)	120.4 (7)
C(17A)—C(18A)—H(15A)	122.9 (7)	C(18B)—C(17B)—H(14B)	118.9 (7)
C(19A)—C(18A)—H(15A)	116.7 (7)	C(17B)—C(18B)—C(19B)	120.72 (9)
O(5A)—C(19A)—C(18A)	115.33 (8)	C(17B)—C(18B)—H(15B)	120.9 (7)
O(5A)—C(19A)—C(20A)	124.90 (9)	C(19B)—C(18B)—H(15B)	118.4 (7)
C(18A)—C(19A)—C(20A)	119.77 (9)	O(5B)—C(19B)—C(18B)	114.87 (9)
C(19A)—C(20A)—C(21A)	119.46 (9)	O(5B)—C(19B)—C(20B)	125.62 (9)
C(19A)—C(20A)—H(16A)	121.6 (7)	C(18B)—C(19B)—C(20B)	119.50 (9)
C(21A)—C(20A)—H(16A)	119.0 (7)	C(19B)—C(20B)—C(21B)	119.30 (9)
C(16A)—C(21A)—C(20A)	121.11 (9)	C(19B)—C(20B)—H(16B)	118.4 (7)
C(16A)—C(21A)—H(17A)	123.1 (8)	C(21B)—C(20B)—H(16B)	122.3 (7)
C(20A)—C(21A)—H(17A)	115.7 (8)	C(16B)—C(21B)—C(20B)	121.72 (9)
O(5A)—C(22A)—C(23A)	106.08 (9)	C(16B)—C(21B)—H(17B)	120.3 (7)
O(5A)—C(22A)—H(18A)	106.6 (8)	C(20B)—C(21B)—H(17B)	117.9 (7)
O(5A)—C(22A)—H(19A)	111.1 (8)	C(23B)—C(22B)—H(18B)	113.6 (8)
C(23A)—C(22A)—H(18A)	110.6 (8)	C(23B)—C(22B)—H(19B)	109.8 (9)
C(23A)—C(22A)—H(19A)	111.1 (8)	H(18B)—C(22B)—H(19B)	109.5 (12)
H(18A)—C(22A)—H(19A)	111.2 (11)	C(22B)—C(23B)—C(24B)	126.06 (10)
C(22A)—C(23A)—C(24A)	126.62 (11)	C(22B)—C(23B)—H(20B)	118.9 (8)
C(22A)—C(23A)—H(20A)	114.9 (8)	C(24B)—C(23B)—H(20B)	115.0 (8)
C(24A)—C(23A)—H(20A)	118.5 (8)	C(23B)—C(24B)—C(25B)	121.75 (12)
C(23A)—C(24A)—C(25A)	120.61 (12)	C(23B)—C(24B)—C(26B)	123.29 (10)
C(23A)—C(24A)—C(26A)	124.48 (10)	C(25B)—C(24B)—C(26B)	114.95 (12)
C(25A)—C(24A)—C(26A)	114.90 (12)	C(24B)—C(25B)—H(21B)	112.5 (10)
C(24A)—C(25A)—H(21A)	112.3 (12)	C(24B)—C(25B)—H(22B)	111.8 (11)
C(24A)—C(25A)—H(22A)	110.7 (12)	C(24B)—C(25B)—H(23B)	110.6 (11)
C(24A)—C(25A)—H(23A)	107.4 (10)	H(21B)—C(25B)—H(22B)	106.8 (15)
H(21A)—C(25A)—H(22A)	105.5 (17)	H(21B)—C(25B)—H(23B)	109.8 (15)
H(21A)—C(25A)—H(23A)	110.9 (16)	H(22B)—C(25B)—H(23B)	104.9 (16)
H(22A)—C(25A)—H(23A)	110.0 (17)	C(24B)—C(26B)—H(24B)	115.3 (13)
C(24A)—C(26A)—H(24A)	116.2 (9)	C(24B)—C(26B)—H(25B)	109.5 (10)
C(24A)—C(26A)—H(25A)	110.2 (12)	C(24B)—C(26B)—H(26B)	113.1 (12)
C(24A)—C(26A)—H(26A)	109.1 (12)	H(24B)—C(26B)—H(25B)	105.8 (16)
H(24A)—C(26A)—H(25A)	102.4 (15)	H(24B)—C(26B)—H(26B)	105.4 (16)
H(24A)—C(26A)—H(26A)	110.7 (15)	H(25B)—C(26B)—H(26B)	107.3 (15)
H(25A)—C(26A)—H(26A)	107.7 (16)