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Acta Cryst. (2006). B62, 843-849
https://doi.org/10.1107/S0108768106019616
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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

R. Kingsford-Adaboh, B. Dittrich, C. B. Hübschle, W. S. K. Gbewonyo, H. Okamoto, M. Kimura and H. Ishida
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.
Keywords: invariom structure refinement; electrostatic potential; electron-density distribution.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768106019616/sn5034sup1.cif
Contains datablocks 4-O-Methyl, O,O-Dimethyl, 5-O-Dimethyl

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106019616/sn50341sup2.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106019616/sn50342sup3.hkl
Contains datablock 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106019616/sn50343sup4.hkl
Contains datablock 3

CCDC references: 624349; 624350; 624351

Computing details top

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 top
[Figure 1]
[Figure 2]
(4-O-Methyl) top
Crystal data top
C21H18O5F(000) = 736
Mr = 350.35Dx = 1.387 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6416 reflections
a = 8.3670 (2) Åθ = 2.4–35.5°
b = 8.4724 (2) ŵ = 0.10 mm−1
c = 23.6852 (5) ÅT = 90 K
β = 92.514 (1)°Plate-like, pale yellow
V = 1677.39 (7) Å30.25 × 0.10 × 0.06 mm
Z = 4
Data collection top
CCD area detector
diffractometer		7659 independent reflections
Radiation source: fine-focus sealed tube5021 reflections with > 2σ(F)
Graphite monochromatorRint = 0.071
Detector resolution: 8.366 pixels mm-1θmax = 35.5°, θmin = 1.7°
phi and ω scansh = −13→13
Absorption correction: empirical (using intensity measurements)
SADABS by G. Sheldrick (Blessing, 1995)		k = −12→13
Tmin = 0.976, Tmax = 0.994l = −35→38
47225 measured reflections
Refinement top
Refinement on F0 restraints
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.030 w1 = 1/[s2(Fo)]
wR(F2) = 0.021(Δ/σ)max < 0.001
S = 1.14Δρmax = 0.32 e Å−3
5021 reflectionsΔρmin = −0.18 e Å−3
307 parameters
Crystal data top
C21H18O5V = 1677.39 (7) Å3
Mr = 350.35Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.3670 (2) ŵ = 0.10 mm−1
b = 8.4724 (2) ÅT = 90 K
c = 23.6852 (5) Å0.25 × 0.10 × 0.06 mm
β = 92.514 (1)°
Data collection top
CCD area detector
diffractometer		7659 independent reflections
Absorption correction: empirical (using intensity measurements)
SADABS by G. Sheldrick (Blessing, 1995)		5021 reflections with > 2σ(F)
Tmin = 0.976, Tmax = 0.994Rint = 0.071
47225 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.021All H-atom parameters refined
S = 1.14Δρmax = 0.32 e Å−3
5021 reflectionsΔρmin = −0.18 e Å−3
307 parameters
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<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)0.2710.020 (2)
H(1)1.3710 (10)0.4950 (10)−0.0090.047 (3)
H(2)1.2070 (10)0.6160 (10)−0.0310.041 (3)
H(3)1.1730 (10)0.4300 (10)00.046 (3)
H(4)1.4740 (10)0.7260 (10)0.0570.049 (3)
H(5)1.3080 (10)0.8360 (10)0.0320.035 (3)
H(6)1.3420 (10)0.8050 (10)0.1050.045 (3)
H(7)1.4240 (10)0.4390 (10)0.0990.033 (3)
H(8)1.2629 (9)0.3700 (10)0.1812 (3)0.026 (2)
H(10)0.4320 (10)0.7980 (10)0.210.028 (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)0.3280.024 (2)
H(15)0.2620 (10)0.6380 (10)0.2530.028 (2)
H(16)−0.0550 (10)0.5130 (10)0.40.039 (3)
H(17)−0.0350 (10)0.7210 (10)0.410.044 (3)
H(18)−0.0570 (10)0.5990 (10)0.4690.033 (3)
DUM10.871090.594830.3268800
DUM20.685460.652860.2107700
DUM31.171950.576950.1070800
DUM40.087220.623020.3835900
DUM51.16220.554320.1063300
DUM60.922390.595170.1591500
DUM70.365670.615510.3492300
DUM80.361910.615180.350600
DUM90.363790.613810.350700
DUM100.363780.616880.3491400
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
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) top
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) top
Crystal data top
C22H20O5F(000) = 768
Mr = 364.38Dx = 1.356 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3689 reflections
a = 9.0604 (7) Åθ = 2.2–31.6°
b = 19.0147 (14) ŵ = 0.10 mm−1
c = 10.5963 (8) ÅT = 90 K
β = 101.333 (2)°Plate-like, colorless
V = 1789.9 (2) Å30.15 × 0.12 × 0.08 mm
Z = 4
Data collection top
CCD area detector
diffractometer		8631 independent reflections
Radiation source: fine-focus sealed tube5234 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.066
Detector resolution: 8.333 pixels mm-1θmax = 36.3°, θmin = 2.1°
phi and ω scansh = −14→15
Absorption correction: empirical (using intensity measurements)
SADABS by Sheldrick (Blessing, 1995)		k = −31→30
Tmin = 0.978, Tmax = 0.990l = −17→17
29061 measured reflections
Refinement top
Refinement on F0 restraints
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.043 w1 = 1/[s2(Fo)]
wR(F2) = 0.028(Δ/σ)max = 0.0004
S = 1.30Δρmax = 0.29 e Å−3
5234 reflectionsΔρmin = −0.27 e Å−3
324 parameters
Crystal data top
C22H20O5V = 1789.9 (2) Å3
Mr = 364.38Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.0604 (7) ŵ = 0.10 mm−1
b = 19.0147 (14) ÅT = 90 K
c = 10.5963 (8) Å0.15 × 0.12 × 0.08 mm
β = 101.333 (2)°
Data collection top
CCD area detector
diffractometer		8631 independent reflections
Absorption correction: empirical (using intensity measurements)
SADABS by Sheldrick (Blessing, 1995)		5234 reflections with I > 2σ(I)
Tmin = 0.978, Tmax = 0.990Rint = 0.066
29061 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.028All H-atom parameters refined
S = 1.30Δρmax = 0.29 e Å−3
5234 reflectionsΔρmin = −0.27 e Å−3
324 parameters
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<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)
DUM10.775981.071940.0541700
DUM20.60230.892480.1653600
DUM30.630.76680.177800
DUM40.665870.83369−0.0862400
DUM50.607710.49025−0.1315400
DUM60.706511.077860.0604400
DUM70.67790.95507−0.0061200
DUM80.712890.60871−0.0709200
DUM90.711530.60673−0.0704400
DUM100.713420.60734−0.070100
DUM110.7110.6081−0.0712500
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
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) top
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) top
Crystal data top
C52H52O10F(000) = 1776
Mr = 836.94Dx = 1.250 Mg m−3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 8567 reflections
a = 11.9602 (3) Åθ = 2.3–35.4°
b = 18.6249 (5) ŵ = 0.09 mm−1
c = 19.9648 (5) ÅT = 120 K
V = 4447.3 (2) Å3Prismatic, colorless
Z = 40.31 × 0.30 × 0.21 mm
Data collection top
CCD area detector
diffractometer		10408 independent reflections
Radiation source: fine-focus sealed tube8668 reflections with > 2σ(F)
Graphite monochromatorRint = 0.063
phi and ω scansθmax = 35.5°, θmin = 1.5°
Absorption correction: empirical (using intensity measurements)
SADABS by Sheldrick (Blessing 1995)		h = −19→19
Tmin = 0.974, Tmax = 0.982k = −30→30
114385 measured reflectionsl = −28→32
Refinement top
Refinement on F0 restraints
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.029 w1 = 1/[s2(Fo)]
wR(F2) = 0.021(Δ/σ)max = 0.0002
S = 1.59Δρmax = 0.33 e Å−3
8668 reflectionsΔρmin = −0.18 e Å−3
764 parameters
Crystal data top
C52H52O10V = 4447.3 (2) Å3
Mr = 836.94Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 11.9602 (3) ŵ = 0.09 mm−1
b = 18.6249 (5) ÅT = 120 K
c = 19.9648 (5) Å0.31 × 0.30 × 0.21 mm
Data collection top
CCD area detector
diffractometer		10408 independent reflections
Absorption correction: empirical (using intensity measurements)
SADABS by Sheldrick (Blessing 1995)		8668 reflections with > 2σ(F)
Tmin = 0.974, Tmax = 0.982Rint = 0.063
114385 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0290 restraints
wR(F2) = 0.021All H-atom parameters refined
S = 1.59Δρmax = 0.33 e Å−3
8668 reflectionsΔρmin = −0.18 e Å−3
764 parameters
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
O(1A)−0.180820.12520.056130.028
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)
DUM1−0.060740.128030.0324400
DUM20.040660.148750.1420300
DUM3−0.007430.293560.0687100
DUM4−0.194610.18657−0.1242300
DUM50.269460.340020.3510500
DUM61.023940.450760.3470100
DUM70.967550.456280.2241400
DUM80.771850.394340.3088800
DUM90.924860.44250.529500
DUM100.652510.37621−0.0151800
DUM11−0.226520.19539−0.1165800
DUM12−0.11080.23812−0.0242200
DUM130.114990.314020.2703300
DUM140.116380.313590.2720400
DUM150.114960.313730.2716100
DUM160.116410.313890.2707600
DUM170.96460.426120.5236100
DUM180.868990.413930.4160500
DUM190.706210.424740.0990200
DUM200.706070.42530.0967100
DUM210.706450.425860.0973600
DUM220.705830.424180.0983700
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
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) top
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)

Experimental details

(4-O-Methyl)(O,O-Dimethyl)(5-O-Dimethyl)
Crystal data
Chemical formulaC21H18O5C22H20O5C52H52O10
Mr350.35364.38836.94
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/nOrthorhombic, Pna21
Temperature (K)9090120
a, b, c (Å)8.3670 (2), 8.4724 (2), 23.6852 (5)9.0604 (7), 19.0147 (14), 10.5963 (8)11.9602 (3), 18.6249 (5), 19.9648 (5)
α, β, γ (°)90, 92.514 (1), 9090, 101.333 (2), 9090, 90, 90
V (Å3)1677.39 (7)1789.9 (2)4447.3 (2)
Z444
Radiation typeMo KαMo KαMo Kα
µ (mm−1)0.100.100.09
Crystal size (mm)0.25 × 0.10 × 0.060.15 × 0.12 × 0.080.31 × 0.30 × 0.21
Data collection
DiffractometerCCD area detector
diffractometer		CCD area detector
diffractometer		CCD area detector
diffractometer
Absorption correctionEmpirical (using intensity measurements)
SADABS by G. Sheldrick (Blessing, 1995)		Empirical (using intensity measurements)
SADABS by Sheldrick (Blessing, 1995)		Empirical (using intensity measurements)
SADABS by Sheldrick (Blessing 1995)
Tmin, Tmax0.976, 0.9940.978, 0.9900.974, 0.982
No. of measured, independent and
observed reflections		47225, 7659, 5021 [ > 2σ(F)]29061, 8631, 5234 [I > 2σ(I)]114385, 10408, 8668 [ > 2σ(F)]
Rint0.0710.0660.063
(sin θ/λ)max (Å−1)0.8170.8330.818
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.021, 1.14 0.043, 0.028, 1.30 0.029, 0.021, 1.59
No. of reflections502152348668
No. of parameters307324764
H-atom treatmentAll H-atom parameters refinedAll H-atom parameters refinedAll H-atom parameters refined
Δρmax, Δρmin (e Å−3)0.32, −0.180.29, −0.270.33, −0.18

Computer programs: Bruker SMART, Bruker SAINT, SADABS, SHELXS97 (Sheldrick, 1990), Koritsanszky et al., (2003).

Selected geometric parameters (Å, º) for (O,O-Dimethyl) top
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)
Selected geometric parameters (Å, º) for (5-O-Dimethyl) top
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)
 

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