organic compounds
Acta Crystallographica Section E Experimental
Structure Reports
Crystal data
Online
C20H16O5 V = 1603.13 (7) Å
3
ISSN 1600-5368 Mr = 336.34 Z = 4
Monoclinic, P21=c Mo K radiation
a = 13.8333 (3) Å  = 0.10 mm1
Alpinumisoflavone b = 5.92699 (17) Å T = 93 (2) K
c = 19.8352 (4) Å 0.53  0.45  0.43 mm
 = 99.6806 (7)

Jerry Joe Ebow Kingsley Harrison,a Youhei Tabuchi,b
Hiroyuki Ishidab and Robert Kingsford-Adaboha* Data collection
Rigaku R-AXIS RAPIDII 30574 measured reflections
aDepartment of Chemistry, Faculty of Science, University of Ghana, Box LG56 diffractometer 4676 independent reflections
Legon, Accra, Ghana, and bDepartment of Chemistry, Faculty of Science, Okayama Absorption correction: multi-scan 4296 reflections with I > 2
(I)
University, Okayama 700-8530, Japan (ABSCOR; Higashi, 1995) Rint = 0.036
T = 0.771, T = 0.958
Correspondence e-mail: kadabohs@ug.edu.gh min max
Received 16 January 2008; accepted 11 March 2008 Refinement
R[F 2 > 2
(F 2)] = 0.042 H atoms treated by a mixture of
Key indicators: single-crystal X-ray study; T = 93 K; mean 
(C–C) = 0.001 Å; R factor = wR(F 2) = 0.123 independent and constrained
0.043; wR factor = 0.124; data-to-parameter ratio = 19.7. S = 1.04 refinement
4676 reflections 
 = 0.51 e Å3max
237 parameters 
 3min = 0.26 e Å
The title compound, C20H16O5, {systematic name: 5-hydroxy-
7-(4-hydroxyphenyl)-2,2-dimethyl-2H,6H-benzo[1,2-b:5,4-b0]-
Table 1
dipyran-6-one}, was obtained by demethylation of the Hydrogen-bond geometry (Å, 
).
biologically active related compound, 4-O-methylalpinumiso-
flavone. The molecular structure of the title compound is D—H  A D—H H  A D  A D—H  A
characterized by a fused tricyclic system that contains an O2—H2O  O3 0.92 (2) 1.76 (2) 2.6023 (10) 152.2 (17)
i
approximately planar benzopyrone ring fragment. The six O5—H5O  O3 0.871 (18) 1.943 (18) 2.7823 (10) 161.4 (17)
membered pyran ring adopts a half-chair conformation. Both Symmetry code: (i) x; y þ 12;z þ 12.
ring systems show an out-of-plane twist. The dihedral angle
between the mean plane of the benzopyrone system and the Data collection: PROCESS-AUTO (Rigaku/MSC, 2004); cell
benzene ring is 54.29 (3)
. The molecules are linked by O— refinement: PROCESS-AUTO ; data reduction: CrystalStructure
H  O hydrogen bonds, forming a molecular tape running (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97
(Sheldrick, 2008); program(s) used to refine structure: SHELXL97
along the b axis.
(Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997);
software used to prepare material for publication: CrystalStructure
Related literature and PLATON (Spek, 2003).
For related compounds, see: Kingsford-Adaboh et al. (2001,
This work was supported by the Japanese Society for the
2006). For ring puckering analysis, see: Cremer & Pople
Promotion of Science (JSPS) Research Program and RK-A
(1975).
thanks the JSPS for the postdoctoral fellowship awarded.
Supplementary data and figures for this paper are available from the
IUCr electronic archives (Reference: FB2087).
References
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Kingsford-Adaboh, R., Ahiano, E., Dittrich, B., Okamoto, H., Kimura, M. &
Ishida, H. (2006). Cryst. Res. Technol. 41, 726–733.
Kingsford-Adaboh, R., Osei-Fosu, P., Asomaning, W. A., Weber, M. & Luger,
P. (2001). Cryst. Res. Technol. 36, 107–115.
Rigaku/MSC (2004). CrystalStructure and PROCESS-AUTO. Rigaku/MSC,
The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.
Acta Cryst. (2008). E64, o713 doi:10.1107/S1600536808006867 Harrison et al. o713
supporting information
supporting information
Acta Cryst. (2008). E64, o713    [doi:10.1107/S1600536808006867]
Alpinumisoflavone
Jerry Joe Ebow Kingsley Harrison, Youhei Tabuchi, Hiroyuki Ishida and Robert Kingsford-
Adaboh
S1. Comment 
The 4-O-methylalpinumisoflavone, O,O-dimethylalpinumisoflavone and 5-O-methyl-4-O-(3-methylbut-2-en-1-
yl)alpinumisoflavone are some of the solvent-extracted compounds from the rootbark and seeds of Milletia thonningii 
whose crystal structures have been studied for obtaining fundamental information on their chemical and biological 
properties (Kingsford-Adaboh et al., 2001, 2006). These compounds have shown considerable brine shrimp lethality 
(Kingsford-Adaboh et al., 2006).
In the present work, single crystals of alpinumisoflavone suitable for X-ray diffraction were obtained by demethylation 
of 4-O-methylalpinumisoflavone using cold BCl3. The crystals isolated from the crude extract were usually of poor 
quality. Therefore we decided to modify 4-O-methylalpinumisoflavone chemically by demethylation (Scheme 2) hoping 
that a new compound would yield crystals of a better quality. This turned to be true. The molecular structure of the title 
compound differs from 4-O-methylalpinumisoflavone only in the replacement of the methoxy group by the hydroxyl on 
the benzene ring D.
The molecular structure of the title compound is characterized by a tricyclic fused ring system, A/B/C, and a benzene 
ring D (Fig. 1). The benzopyrone ring fragment, B/C, is planar and it is twisted out of plane with respect to the benzene 
ring D. The outer six-membered ring A is deformed into a half-chair conformation, with Cremer & Pople (1975) 
parameters q2, q3 and φ2 of 0.2342 (9), -0.1148 (9) Å and 220.4 (2)°, respectively.
The presence of the hydroxyl group proximal to the keto group on the ring C permits the formation of a relatively 
stronger intramolecular O—H···O hydrogen bond (Table 1). This distance is comparable to the intramolecular contact 
distance equal to 1.724 (17) Å in 4-O-methylalpinumisoflavone which is the closest related compound in the studied 
series (Kingsford-Adaboh et al., 2001, 2006). The corresponding distances observed in other members of the series are 
longer (ca 2.3 Å; Kingsford-Adaboh et al., 2006).
The observed intramolecular contact is affected by the coplanar arrangement between the hydroxyl and the carbonyl 
groups in the pertinent part of the molecule. This is demonstrated by the observed torsion angle C9—C8—C7—O2 = 
-1.19 (13)° in the title structure. The largest deviation from the coplanarity in the series is observed in O,O-dimethyl-
alpinumisoflavone with the corresponding angle equal to -12.83 (18)° (Kingsford-Adaboh et al., 2001). The 
intermolecular O—H···O hydrogen bond (Table 1), where the terminal OH group of the benzene ring D serves as a proton 
donor to the carbonyl oxygen atom, is observed to play an important role in the molecular bonding in the crystal structure 
(Tab. 1, Fig. 2).
Acta Cryst. (2008). E64, o713    sup-1
supporting information
S2. Experimental 
Alpinumisoflavone was obtained from the demethylation of 4-O-methylalpinumisoflavone. Solvent extraction of 4-O-
methylalpinumisoflavone from the pulverized root bark of Milletia thonningii followed similar procedure as described in 
our earlier work (Kingsford-Adaboh et al., 2001). A cold solution of BCl3 in chloroform (-78 °C) was added slowly to 
about 15 ml of a chloroform solution of 4-O-methylalpinumisoflavone (200 mg, 0.571 mmol) cooled to -78 °C using dry 
ice and acetone mixture. The solution was stirred for about 10 min under argon atmosphere. 30 ml of water was added 
slowly and the resulting yellowish mixture was extracted with chloroform three times. The combined extracts were 
washed with water twice and then dried over anhydrous sodium sulphate. After evaporation of the solvent under vacuum, 
the residue was chromatographed on a silica gel using petroleum ether and ethylacetate mixture in the ratio of between 
8/1 and 5/1 as the mobile phase. The product was recrystallized from acetonitrile. The demethylation yield (159.6 mg 
about 80%, m.p. 486 K). The product was confirmed by 13C NMR spectra of both the reactants and the product.)
S3. Refinement 
All the H atoms were located in the difference Fourier map. The H atoms that have been attached to the C atoms were 
constrained in idealized geometry while the hydroxyl H atoms were freely isotropically refined. Cmethyl—H= 0.98 Å 
allowing for rotation around the C—C bond with Uiso(Hmethyl) = 1.5Ueq(Cmethyl). Caryl—H = 0.95 Å with Uiso(Haryl) = 
1.2Ueq(Caryl).
Figure 1
The molecular structure of the title compound. The displacement ellipsoids are drawn at the 50% probability level. 
Acta Cryst. (2008). E64, o713    sup-2
supporting information
Figure 2
Crystal packing viewed on the a-c plane. Hydrogen bonds are shown as broken lines. 
5-hydroxy-7-(4-hydroxyphenyl)-2,2- dimethyl-2H,6H-benzo[1,2 - b:5,4 - b′]dipyran-6-one 
Crystal data 
C20H16O5 F(000) = 704.00
Mr = 336.34 Dx = 1.393 Mg m−3
Monoclinic, P21/c Melting point: 486 K
Hall symbol: -P 2ybc Mo Kα radiation, λ = 0.71075 Å
a = 13.8333 (3) Å Cell parameters from 27371 reflections
b = 5.92699 (17) Å θ = 3.0–30.0°
c = 19.8352 (4) Å µ = 0.10 mm−1
β = 99.6806 (7)° T = 93 K
V = 1603.13 (7) Å3 Block, yellow
Z = 4 0.53 × 0.45 × 0.43 mm
Acta Cryst. (2008). E64, o713    sup-3
supporting information
Data collection 
Rigaku R-AXIS RAPIDII 4676 independent reflections
diffractometer 4296 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm-1 Rint = 0.036
ω scans θmax = 30.0°, θmin = 3.3°
Absorption correction: multi-scan h = −19→17
(ABSCOR; Higashi, 1995) k = −8→8
Tmin = 0.771, Tmax = 0.958 l = −27→27
30574 measured reflections
Refinement 
Refinement on F2 Secondary atom site location: difference Fourier 
Least-squares matrix: full map
R[F2 > 2σ(F2)] = 0.042 Hydrogen site location: difference Fourier map
wR(F2) = 0.123 H atoms treated by a mixture of independent 
S = 1.04 and constrained refinement
4676 reflections w = 1/[σ2(F 2o ) + (0.0785P)2 + 0.3851P] 
237 parameters where P = (F 2o  + 2F 2c )/3
0 restraints (Δ/σ)max < 0.001
54 constraints Δρ −3max = 0.51 e Å
Primary atom site location: structure-invariant Δρ −3min = −0.26 e Å
direct methods Extinction correction: SHELXL, 
Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Extinction coefficient: 0.015 (2)
Special details 
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full 
covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and 
torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. 
An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, 
conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used 
only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 
are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
Although there were present diffractions that violated the space-group-systematic absences the average I/σ values for h0l 
with l = 2n and for l =2n+1 were 25.6 and 0.8, respectively. This indicates presence of the c glide plane. Thus we selected 
P21/c. We have also refined the structure with P21. All atoms except H completely fit to the c and i symmetries. The 
reflections that should be absent for P21/c might be accidentally observed. Probably some of them were diffractions from 
small ice particles (frost) generated in the X-ray beam path.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) 
x y z Uiso*/Ueq
O1 0.70895 (5) 0.49566 (11) 0.41410 (3) 0.01881 (15)
O2 0.42098 (5) 0.04434 (11) 0.39657 (4) 0.02165 (16)
O3 0.26668 (5) 0.18561 (11) 0.31384 (3) 0.02019 (15)
O4 0.42341 (4) 0.74216 (11) 0.27339 (3) 0.01861 (15)
O5 −0.12257 (5) 0.49357 (12) 0.12202 (4) 0.02212 (16)
C1 0.74810 (9) 0.50860 (18) 0.53739 (5) 0.0300 (2)
H1A 0.7776 0.6578 0.5344 0.045*
H1B 0.7814 0.4307 0.5784 0.045*
H1C 0.6784 0.5257 0.5401 0.045*
C2 0.86499 (7) 0.3562 (2) 0.46408 (6) 0.0312 (2)
Acta Cryst. (2008). E64, o713    sup-4
supporting information
H2A 0.8685 0.2740 0.4217 0.047*
H2B 0.9035 0.2764 0.5028 0.047*
H2C 0.8915 0.5086 0.4611 0.047*
C3 0.75883 (6) 0.37155 (15) 0.47438 (4) 0.01759 (17)
C4 0.71488 (7) 0.14234 (16) 0.47920 (5) 0.0231 (2)
H4 0.7539 0.0268 0.5033 0.028*
C5 0.62256 (7) 0.09525 (16) 0.45064 (5) 0.02201 (19)
H5 0.5948 −0.0474 0.4580 0.026*
C6 0.56482 (6) 0.26353 (14) 0.40815 (4) 0.01600 (17)
C7 0.46669 (6) 0.23138 (14) 0.37950 (4) 0.01593 (17)
C8 0.41581 (6) 0.38972 (14) 0.33266 (4) 0.01501 (16)
C9 0.31511 (6) 0.35590 (14) 0.30076 (4) 0.01544 (16)
C10 0.27298 (6) 0.53058 (15) 0.25305 (4) 0.01599 (16)
C11 0.32922 (6) 0.71046 (16) 0.24342 (4) 0.01798 (17)
H11 0.3000 0.8244 0.2130 0.022*
C12 0.46784 (6) 0.58219 (14) 0.31783 (4) 0.01550 (17)
C13 0.56476 (6) 0.62234 (15) 0.34640 (4) 0.01663 (17)
H13 0.5977 0.7550 0.3357 0.020*
C14 0.61209 (6) 0.46139 (15) 0.39122 (4) 0.01554 (16)
C15 0.16979 (6) 0.52188 (15) 0.21756 (4) 0.01598 (17)
C16 0.13347 (6) 0.33720 (15) 0.17706 (4) 0.01859 (18)
H16 0.1757 0.2145 0.1715 0.022*
C17 0.03611 (7) 0.33194 (16) 0.14484 (5) 0.01923 (18)
H17 0.0121 0.2060 0.1174 0.023*
C18 −0.02636 (6) 0.51134 (15) 0.15274 (4) 0.01714 (17)
C19 0.00911 (6) 0.69858 (15) 0.19145 (5) 0.01829 (17)
H19 −0.0328 0.8227 0.1959 0.022*
C20 0.10686 (6) 0.70239 (15) 0.22366 (4) 0.01783 (17)
H20 0.1311 0.8300 0.2502 0.021*
H2O 0.3584 (15) 0.054 (3) 0.3729 (10) 0.057 (5)*
H5O −0.1591 (13) 0.580 (3) 0.1428 (9) 0.046 (4)*
Atomic displacement parameters (Å2) 
U11 U22 U33 U12 U13 U23
O1 0.0133 (3) 0.0231 (3) 0.0186 (3) −0.0020 (2) −0.0014 (2) 0.0047 (2)
O2 0.0188 (3) 0.0184 (3) 0.0268 (3) −0.0039 (2) 0.0009 (3) 0.0060 (2)
O3 0.0156 (3) 0.0197 (3) 0.0251 (3) −0.0029 (2) 0.0029 (2) 0.0019 (2)
O4 0.0145 (3) 0.0206 (3) 0.0195 (3) −0.0014 (2) −0.0006 (2) 0.0063 (2)
O5 0.0133 (3) 0.0288 (4) 0.0226 (3) 0.0034 (2) −0.0018 (2) −0.0033 (3)
C1 0.0459 (6) 0.0234 (5) 0.0193 (4) 0.0037 (4) 0.0018 (4) −0.0028 (3)
C2 0.0159 (4) 0.0492 (7) 0.0277 (5) 0.0032 (4) 0.0010 (4) 0.0116 (4)
C3 0.0160 (4) 0.0206 (4) 0.0149 (3) 0.0002 (3) −0.0010 (3) 0.0012 (3)
C4 0.0228 (4) 0.0178 (4) 0.0258 (4) 0.0007 (3) −0.0043 (4) 0.0024 (3)
C5 0.0217 (4) 0.0165 (4) 0.0253 (4) −0.0008 (3) −0.0031 (3) 0.0030 (3)
C6 0.0156 (4) 0.0158 (4) 0.0162 (4) 0.0000 (3) 0.0013 (3) 0.0007 (3)
C7 0.0157 (4) 0.0154 (4) 0.0170 (4) −0.0010 (3) 0.0035 (3) 0.0006 (3)
C8 0.0126 (3) 0.0173 (4) 0.0153 (3) 0.0000 (3) 0.0027 (3) 0.0006 (3)
Acta Cryst. (2008). E64, o713    sup-5
supporting information
C9 0.0131 (3) 0.0179 (4) 0.0157 (3) 0.0001 (3) 0.0036 (3) −0.0012 (3)
C10 0.0129 (3) 0.0194 (4) 0.0156 (3) 0.0011 (3) 0.0022 (3) −0.0005 (3)
C11 0.0139 (4) 0.0219 (4) 0.0175 (4) 0.0009 (3) 0.0008 (3) 0.0025 (3)
C12 0.0149 (4) 0.0174 (4) 0.0144 (3) 0.0008 (3) 0.0027 (3) 0.0020 (3)
C13 0.0147 (4) 0.0182 (4) 0.0169 (4) −0.0017 (3) 0.0023 (3) 0.0022 (3)
C14 0.0135 (3) 0.0185 (4) 0.0145 (3) −0.0008 (3) 0.0020 (3) −0.0005 (3)
C15 0.0126 (3) 0.0197 (4) 0.0155 (3) 0.0014 (3) 0.0020 (3) 0.0000 (3)
C16 0.0158 (4) 0.0200 (4) 0.0196 (4) 0.0036 (3) 0.0020 (3) −0.0027 (3)
C17 0.0167 (4) 0.0213 (4) 0.0188 (4) 0.0019 (3) 0.0006 (3) −0.0037 (3)
C18 0.0135 (4) 0.0219 (4) 0.0157 (3) 0.0018 (3) 0.0015 (3) 0.0007 (3)
C19 0.0154 (4) 0.0193 (4) 0.0203 (4) 0.0035 (3) 0.0033 (3) −0.0008 (3)
C20 0.0153 (4) 0.0188 (4) 0.0195 (4) 0.0007 (3) 0.0032 (3) −0.0024 (3)
Geometric parameters (Å, º) 
O1—C14 1.3558 (10) C6—C7 1.3937 (11)
O1—C3 1.4728 (10) C6—C14 1.4105 (12)
O2—C7 1.3474 (10) C7—C8 1.4210 (11)
O2—H2O 0.92 (2) C8—C12 1.4062 (11)
O3—C9 1.2623 (10) C8—C9 1.4438 (11)
O4—C11 1.3512 (10) C9—C10 1.4565 (12)
O4—C12 1.3680 (10) C10—C11 1.3522 (12)
O5—C18 1.3714 (10) C10—C15 1.4824 (11)
O5—H5O 0.871 (18) C11—H11 0.9500
C1—C3 1.5186 (13) C12—C13 1.3856 (11)
C1—H1A 0.9800 C13—C14 1.3904 (12)
C1—H1B 0.9800 C13—H13 0.9500
C1—H1C 0.9800 C15—C20 1.3973 (11)
C2—C3 1.5190 (13) C15—C16 1.4001 (12)
C2—H2A 0.9800 C16—C17 1.3907 (11)
C2—H2B 0.9800 C16—H16 0.9500
C2—H2C 0.9800 C17—C18 1.3956 (12)
C3—C4 1.4980 (13) C17—H17 0.9500
C4—C5 1.3366 (12) C18—C19 1.3911 (12)
C4—H4 0.9500 C19—C20 1.3952 (11)
C5—C6 1.4549 (12) C19—H19 0.9500
C5—H5 0.9500 C20—H20 0.9500
C14—O1—C3 119.91 (7) O3—C9—C8 121.81 (8)
C7—O2—H2O 105.4 (12) O3—C9—C10 122.26 (7)
C11—O4—C12 118.85 (7) C8—C9—C10 115.93 (7)
C18—O5—H5O 110.0 (12) C11—C10—C9 118.38 (8)
C3—C1—H1A 109.5 C11—C10—C15 119.43 (8)
C3—C1—H1B 109.5 C9—C10—C15 122.13 (7)
H1A—C1—H1B 109.5 O4—C11—C10 125.64 (8)
C3—C1—H1C 109.5 O4—C11—H11 117.2
H1A—C1—H1C 109.5 C10—C11—H11 117.2
H1B—C1—H1C 109.5 O4—C12—C13 116.33 (7)
Acta Cryst. (2008). E64, o713    sup-6
supporting information
C3—C2—H2A 109.5 O4—C12—C8 120.45 (7)
C3—C2—H2B 109.5 C13—C12—C8 123.22 (8)
H2A—C2—H2B 109.5 C12—C13—C14 117.57 (8)
C3—C2—H2C 109.5 C12—C13—H13 121.2
H2A—C2—H2C 109.5 C14—C13—H13 121.2
H2B—C2—H2C 109.5 O1—C14—C13 116.35 (7)
O1—C3—C4 111.41 (7) O1—C14—C6 121.10 (7)
O1—C3—C1 107.68 (7) C13—C14—C6 122.37 (8)
C4—C3—C1 109.62 (8) C20—C15—C16 118.66 (8)
O1—C3—C2 104.61 (7) C20—C15—C10 119.76 (8)
C4—C3—C2 111.49 (8) C16—C15—C10 121.57 (7)
C1—C3—C2 111.90 (9) C17—C16—C15 120.50 (8)
C5—C4—C3 122.11 (8) C17—C16—H16 119.7
C5—C4—H4 118.9 C15—C16—H16 119.7
C3—C4—H4 118.9 C16—C17—C18 120.10 (8)
C4—C5—C6 119.65 (8) C16—C17—H17 120.0
C4—C5—H5 120.2 C18—C17—H17 120.0
C6—C5—H5 120.2 O5—C18—C19 122.17 (8)
C7—C6—C14 118.38 (8) O5—C18—C17 117.68 (8)
C7—C6—C5 123.00 (8) C19—C18—C17 120.14 (8)
C14—C6—C5 118.46 (8) C18—C19—C20 119.37 (8)
O2—C7—C6 118.43 (8) C18—C19—H19 120.3
O2—C7—C8 120.39 (7) C20—C19—H19 120.3
C6—C7—C8 121.18 (8) C19—C20—C15 121.19 (8)
C12—C8—C7 117.25 (7) C19—C20—H20 119.4
C12—C8—C9 120.73 (7) C15—C20—H20 119.4
C7—C8—C9 122.02 (8)
C14—O1—C3—C4 31.87 (11) C11—O4—C12—C8 −0.83 (12)
C14—O1—C3—C1 −88.36 (10) C7—C8—C12—O4 −179.76 (7)
C14—O1—C3—C2 152.45 (8) C9—C8—C12—O4 0.74 (12)
O1—C3—C4—C5 −24.52 (13) C7—C8—C12—C13 0.13 (13)
C1—C3—C4—C5 94.56 (11) C9—C8—C12—C13 −179.37 (8)
C2—C3—C4—C5 −140.97 (10) O4—C12—C13—C14 −179.35 (7)
C3—C4—C5—C6 5.75 (15) C8—C12—C13—C14 0.76 (13)
C4—C5—C6—C7 −176.66 (9) C3—O1—C14—C13 163.91 (7)
C4—C5—C6—C14 7.97 (14) C3—O1—C14—C6 −20.89 (12)
C14—C6—C7—O2 −178.87 (7) C12—C13—C14—O1 174.83 (7)
C5—C6—C7—O2 5.75 (13) C12—C13—C14—C6 −0.31 (13)
C14—C6—C7—C8 1.94 (13) C7—C6—C14—O1 −175.92 (7)
C5—C6—C7—C8 −173.44 (8) C5—C6—C14—O1 −0.33 (12)
O2—C7—C8—C12 179.31 (7) C7—C6—C14—C13 −1.02 (13)
C6—C7—C8—C12 −1.51 (12) C5—C6—C14—C13 174.57 (8)
O2—C7—C8—C9 −1.19 (13) C11—C10—C15—C20 −53.12 (12)
C6—C7—C8—C9 177.98 (7) C9—C10—C15—C20 124.00 (9)
C12—C8—C9—O3 −179.25 (8) C11—C10—C15—C16 126.14 (9)
C7—C8—C9—O3 1.27 (13) C9—C10—C15—C16 −56.74 (12)
C12—C8—C9—C10 0.40 (12) C20—C15—C16—C17 −1.39 (13)
Acta Cryst. (2008). E64, o713    sup-7
supporting information
C7—C8—C9—C10 −179.08 (7) C10—C15—C16—C17 179.35 (8)
O3—C9—C10—C11 178.22 (8) C15—C16—C17—C18 −0.07 (14)
C8—C9—C10—C11 −1.43 (12) C16—C17—C18—O5 −177.52 (8)
O3—C9—C10—C15 1.07 (13) C16—C17—C18—C19 1.62 (14)
C8—C9—C10—C15 −178.58 (7) O5—C18—C19—C20 177.44 (8)
C12—O4—C11—C10 −0.31 (13) C17—C18—C19—C20 −1.67 (13)
C9—C10—C11—O4 1.47 (14) C18—C19—C20—C15 0.18 (13)
C15—C10—C11—O4 178.70 (8) C16—C15—C20—C19 1.34 (13)
C11—O4—C12—C13 179.27 (7) C10—C15—C20—C19 −179.39 (8)
Hydrogen-bond geometry (Å, º) 
D—H···A D—H H···A D···A D—H···A
O2—H2O···O3 0.92 (2) 1.76 (2) 2.6023 (10) 152.2 (17)
O5—H5O···O3i 0.871 (18) 1.943 (18) 2.7823 (10) 161.4 (17)
Symmetry code: (i) −x, y+1/2, −z+1/2.
Acta Cryst. (2008). E64, o713    sup-8