organic papers
o116
A. Abdul Ajeeset al. C25H28O8 DOI: 101107/S1600536801000733 Acta Cryst.(2001). E57, o116±o117 Acta Crystallographica Section EStructure Reports
Online ISSN 1600-5368
Tricoccin R6
A. Abdul Ajees,aK. Sekar,bS.
Parthasarathy,a* H. Schenk,cB.
Epedand A. Mondond
aDepartment of Crystallography and Biophysics,
University of Madras, Guindy Campus, Chennai 600 025, India,bBioinformatics Centre, Raman Building, Indian Institute of Science, Bangalore 560 012, India,cLaboratory Voor Kristallografie, Nieuwe Achtergracht 166, 1018, WU, Amsterdam, The Netherlands, anddInstitute of Organic Chemistry, University of Kiel, D-2300 Kiel, Olshausenstrasse Be 40-60, Germany
Correspondence e-mail: [email protected]
Key indicators Single-crystal X-ray study T= 293 K
Mean(C±C) = 0.004 AÊ Rfactor = 0.033 wRfactor = 0.092 Data-to-parameter ratio = 8.0
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2001 International Union of Crystallography Printed in Great Britain ± all rights reserved
The X-ray crystal structure of the title compound, C25H28O8,
has been determined. In the structure, both the terminal ®ve-membered rings (A and F) are planar. The fused ®ve-membered ringsCandEare in envelope conformations, and ringB is in a slightly distorted half-chair conformation. The six-membered ringDis in a slightly distorted sofa conforma-tion. The structure is stabilized by OÐH O hydrogen bonds and CÐH O and intramolecular inter-actions.
Comment
The molecular structure of tricoccin R6, (I), is shown in Fig. 1. The bond geometry conforms to expectations. The puckering parameters evaluated using PARST97 (Nardelli, 1995) show that (i) both the terminal ®ve-membered rings (A andF) are planar, (ii) the fused ®ve-membered ringBis in a slightly distorted half-chair conformation, and ringsCandE are in envelope conformations [q2 = 0.334 (2) AÊ, '2 =
ÿ119.7 (4)for ringB, q
2= 0.440 (2) AÊ,'2=ÿ134.7 (3)for
ringC, andq2= 0.129 (2) AÊ,'2= 151.2 (11)for ringE]. The
six-membered ringDhas a slightly distorted sofa conforma-tion [q2 = 0.369 (3), q3 = 0.364 (3), QT = 0.519 (2) AÊ, '2 =
63.0 (4)]. Fig. 2 shows the packing diagram of the molecules.
The structure is stabilized by intermolecular OÐH O hydrogen bonds and CÐH O inter- and intramolecular interactions (see Table 1).
Experimental
The title compound was isolated fromCneorum tricoccinL., a shrub native to coastal areas of the western Mediterranean with hairless leaves, yellow blossoms and red fruits (Herz et al., 1983). It was crystallized from ethanol/acetone.
Crystal data C25H28O8
Mr= 456.47
Orthorhombic,P212121
a= 7.224 (2) AÊ b= 15.521 (2) AÊ c= 20.404 (1) AÊ V= 2287.8 (7) AÊ3
Z= 4
Dx= 1.325 Mg mÿ3
CuKradiation Cell parameters from 25
re¯ections
= 20±30 = 0.82 mmÿ1
T= 293 (2) K
Section from needle, colourless 0.250.250.20 mm
Data collection
Enraf±Nonius CAD-4 diffract-ometer
!/2scans
2417 measured re¯ections 2417 independent re¯ections 2171 re¯ections withI> 2(I)
max= 69.9
h= 0!8 k= 0!18 l= 0!24
3 standard re¯ections frequency: 120 min intensity decay: <1%
Re®nement Re®nement onF2
R[F2> 2(F2)] = 0.033
wR(F2) = 0.092
S= 1.04 2417 re¯ections 303 parameters
H-atom parameters constrained w= 1/[2(F
o2) + (0.0539P)2 + 0.3026P]
whereP= (Fo2+ 2Fc2)/3
(/)max= 0.001
max= 0.19 e AÊÿ3
min=ÿ0.17 e AÊÿ3
Extinction correction:SHELXL97 Extinction coef®cient: 0.0078 (4) Absolute structure: Flack (1983) Flack parameter = 0.2 (2)
Table 1
Hydrogen-bonding geometry (AÊ,).
DÐH A DÐH H A D A DÐH A
C28ÐH28C O32 0.96 2.41 2.894 (4) 111 O26ÐH26 O25i 0.82 2.00 2.805 (2) 169 C23ÐH23 O31ii 0.93 2.43 3.283 (3) 152
Symmetry codes: (i)xÿ1
2;12ÿy;2ÿz; (ii) 2ÿx;yÿ12;52ÿz.
The data set contains no Friedel pairs.
Data collection: CAD-4 Software (Enraf±Nonius, 1989); cell re®nement: SDP (Frenz, 1978); data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to re®ne structure:SHELXL97 (Sheldrick, 1997); molecular graphics:ORTEPIII (Johnson & Burnett, 1998); software used to prepare material for publication:SHELXL97 andPARST97 (Nardelli, 1995).
References
Enraf±Nonius (1989).CAD-4Software. Version 5.0. Enraf±Nonius, Delft, The Netherlands.
Flack, H. D. (1983).Acta Cryst.A39, 876±881.
Frenz, B. A. (1978).The Enraf±Nonius CAD-4SDP±a Real-Time System for Concurrent X-ray Data Collection and Crystal Structure Solution. Computing in Crystallography, edited by H. Schenk, R. Olthof-Hazekamp, H. van Koningsveld & G. C. Bassi, pp. 64±71. Delft University Press. Herz, W., Grisebach, H. & Kirby, G. W. (1983). Progress in the Chemistry of
Organic Natural Products, Vol. 44, pp. 101±187. Wien, New York: Springer Verlag.
Johnson, C. K. & Burnett, M. N. (1998).ORTEPIII. University of Glasgow, Scotland.
Nardelli, M. (1995).J. Appl. Cryst.28, 659.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. Release 97±2. University of GoÈttingen, Germany.
Figure 1
supporting information
sup-1
Acta Cryst. (2001). E57, o116–o117
supporting information
Acta Cryst. (2001). E57, o116–o117 [doi:10.1107/S1600536801000733]
Tricoccin R6
A. Abdul Ajees, K. Sekar, S. Parthasarathy, H. Schenk, B. Epe and A. Mondon
S1. Comment
The molecular structure of tricoccin R6, (I), is shown in Fig. 1. The bond geometry conforms to expectations. The
puckering parameters evaluated using PARST97 (Nardelli, 1995) show that (i) both the terminal five-membered rings (A
and F) are planar, (ii) the fused five-membered ring B is in a slightly distorted half-chair conformation, and rings C and E
are in envelope conformations [q2 = 0.334 (2) Å, φ2 = -119.7 (4)° for ring B, q2 = 0.440 (2) Å, φ2 = -134.7 (3)° for ring C,
and q2 = 0.129 (2) Å, φ2 = 151.2 (11)° for ring E]. The six-membered ring D has a slightly distorted sofa conformation [q2
= 0.369 (3), q3 = 0.364 (3), QT = 0.519 (2) Å, φ2 = 63.0 (4)°]. Fig. 2 shows the packing diagram of the molecules. The
structure is stabilized by intermolecular O—H···O hydrogen bonds and C—H—O inter- and intramolecular interactions
(see Table 1).
S2. Experimental
The title compound was isolated from Cneorum tricoccin L., a shrub native to coastal areas of the western Mediterranean
with hairless leaves, yellow blossoms and red fruits (Herz et al., 1983). It was crystallized from ethanol/acetone.
S3. Refinement
[image:3.610.113.485.444.633.2]The data set contains no Friedel pairs.
Figure 1
Figure 2
Packing diagram of the title compound viewed along the b axis.
(I)
Crystal data
C25H28O8
Mr = 456.47
Orthorhombic, P212121
a = 7.224 (2) Å
b = 15.521 (2) Å
c = 20.404 (1) Å
V = 2287.8 (7) Å3
Z = 4
F(000) = 968
Dx = 1.325 Mg m−3
Cu Kα radiation, λ = 1.54180 Å Cell parameters from 25 reflections
θ = 20–30°
µ = 0.82 mm−1
T = 293 K Needle, colourless 0.25 × 0.25 × 0.20 mm
Data collection
Enraf-Nonius CAD-4 diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
ω/2θ scans
2417 measured reflections 2417 independent reflections 2171 reflections with I > 2σ(I)
Rint = 0.000
θmax = 69.9°, θmin = 3.6°
h = 0→8
k = 0→18
l = 0→24
3 standard reflections every 120 min intensity decay: <1%
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.033
wR(F2) = 0.092
S = 1.04 2417 reflections 303 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier
Hydrogen site location: inferred from neighbouring sites
H-atom parameters constrained
w = 1/[σ2(F
o2) + (0.0539P)2 + 0.3026P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001
Δρmax = 0.19 e Å−3
Δρmin = −0.17 e Å−3
Extinction correction: SHELXL07, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
supporting information
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Acta Cryst. (2001). E57, o116–o117
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.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq
C1 −0.0011 (4) 0.44829 (18) 0.91298 (12) 0.0514 (6)
H1 −0.0884 0.4147 0.9347 0.062*
C2 0.0661 (5) 0.43112 (18) 0.85488 (13) 0.0582 (7)
H2 0.0317 0.3849 0.8286 0.070*
C3 0.2029 (5) 0.49599 (17) 0.83820 (12) 0.0576 (7)
C4 0.3046 (4) 0.58439 (16) 1.03575 (12) 0.0522 (6)
C5 0.1881 (4) 0.51129 (15) 1.00390 (10) 0.0421 (5)
H5 0.0954 0.4942 1.0364 0.051*
C6 0.3230 (4) 0.43608 (14) 0.99777 (11) 0.0427 (5)
H6A 0.2593 0.3813 1.0019 0.051*
H6B 0.3879 0.4377 0.9562 0.051*
C7 0.4547 (4) 0.45026 (14) 1.05433 (11) 0.0408 (5)
C8 0.6596 (3) 0.34735 (13) 1.10470 (10) 0.0355 (5)
C9 0.5305 (3) 0.39130 (15) 1.15372 (10) 0.0396 (5)
H9 0.5905 0.4432 1.1710 0.047*
C10 0.0822 (4) 0.52963 (15) 0.93978 (11) 0.0445 (5)
C11 0.4825 (4) 0.33158 (17) 1.20975 (11) 0.0469 (6)
H11A 0.4279 0.2790 1.1928 0.056*
H11B 0.3931 0.3590 1.2384 0.056*
C12 0.6596 (4) 0.31011 (19) 1.24852 (11) 0.0518 (6)
H12A 0.6800 0.3555 1.2804 0.062*
H12B 0.6384 0.2572 1.2727 0.062*
C13 0.8365 (3) 0.29927 (14) 1.20829 (10) 0.0372 (5)
C14 0.8410 (3) 0.32540 (13) 1.13677 (10) 0.0357 (5)
C15 0.9635 (4) 0.26286 (16) 1.10388 (11) 0.0441 (5)
O16 1.0349 (3) 0.20671 (11) 1.14794 (8) 0.0543 (5)
C17 0.9415 (4) 0.21545 (14) 1.21156 (10) 0.0417 (5)
H17 0.8513 0.1686 1.2155 0.050*
C18 0.9432 (4) 0.37711 (14) 1.18752 (10) 0.0406 (5)
H18A 1.0772 0.3734 1.1879 0.049*
H18B 0.8935 0.4331 1.1991 0.049*
C19 −0.0644 (5) 0.6001 (2) 0.94640 (15) 0.0669 (8)
H19A −0.0058 0.6533 0.9584 0.100*
H19B −0.1519 0.5841 0.9796 0.100*
C20 1.0822 (3) 0.20472 (14) 1.26463 (11) 0.0414 (5)
C21 1.1910 (5) 0.13015 (17) 1.27584 (14) 0.0588 (7)
H21 1.1909 0.0798 1.2511 0.071*
C22 1.1283 (4) 0.26077 (17) 1.31191 (12) 0.0503 (6)
H22 1.0786 0.3158 1.3163 0.060*
C23 1.2935 (5) 0.14616 (19) 1.32873 (16) 0.0681 (8)
H23 1.3781 0.1079 1.3469 0.082*
O24 1.2571 (3) 0.22641 (13) 1.35249 (9) 0.0662 (6)
O25 1.0044 (3) 0.25932 (14) 1.04679 (8) 0.0633 (6)
O26 0.5807 (3) 0.26671 (11) 1.08654 (7) 0.0492 (4)
H26 0.5599 0.2665 1.0470 0.074*
O27 0.3774 (2) 0.41558 (11) 1.11359 (8) 0.0493 (4)
C28 0.3810 (6) 0.65439 (18) 0.99111 (18) 0.0801 (11)
H28A 0.4712 0.6877 1.0145 0.120*
H28B 0.2818 0.6912 0.9771 0.120*
H28C 0.4380 0.6284 0.9535 0.120*
C29 0.2061 (6) 0.6227 (3) 1.09453 (17) 0.0929 (13)
H29A 0.1845 0.5784 1.1265 0.139*
H29B 0.0900 0.6468 1.0809 0.139*
H29C 0.2816 0.6671 1.1135 0.139*
C30 0.6516 (3) 0.41203 (15) 1.04874 (11) 0.0422 (5)
H30A 0.6693 0.3838 1.0068 0.051*
H30B 0.7450 0.4564 1.0540 0.051*
O31 0.4710 (3) 0.54090 (10) 1.05931 (8) 0.0506 (4)
O32 0.2099 (3) 0.55420 (10) 0.88795 (8) 0.0519 (5)
O33 0.3017 (4) 0.50316 (15) 0.79069 (10) 0.0880 (8)
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
C1 0.0454 (14) 0.0577 (15) 0.0513 (13) −0.0012 (12) −0.0097 (12) 0.0012 (11)
C2 0.0699 (18) 0.0536 (14) 0.0509 (14) 0.0031 (15) −0.0113 (15) −0.0073 (12)
C3 0.085 (2) 0.0476 (13) 0.0404 (12) 0.0124 (15) 0.0016 (14) 0.0050 (10)
C4 0.0616 (15) 0.0431 (12) 0.0518 (13) 0.0092 (13) −0.0173 (13) −0.0084 (11)
C5 0.0481 (13) 0.0423 (12) 0.0359 (10) 0.0025 (11) −0.0040 (11) 0.0025 (9)
C6 0.0530 (14) 0.0347 (10) 0.0405 (11) 0.0000 (11) −0.0110 (11) 0.0019 (9)
C7 0.0464 (13) 0.0373 (11) 0.0387 (11) −0.0018 (10) −0.0062 (11) 0.0041 (9)
C8 0.0409 (12) 0.0371 (10) 0.0285 (9) −0.0033 (10) −0.0042 (9) −0.0004 (8)
C9 0.0400 (12) 0.0466 (12) 0.0321 (10) 0.0032 (10) −0.0028 (10) 0.0032 (9)
C10 0.0500 (14) 0.0450 (12) 0.0386 (11) 0.0064 (12) −0.0053 (11) 0.0028 (9)
C11 0.0436 (13) 0.0609 (15) 0.0361 (11) 0.0058 (12) 0.0078 (10) 0.0085 (11)
C12 0.0503 (14) 0.0744 (16) 0.0306 (10) 0.0073 (14) 0.0034 (11) 0.0076 (11)
C13 0.0433 (12) 0.0420 (11) 0.0263 (9) 0.0028 (10) −0.0035 (9) 0.0001 (8)
C14 0.0420 (12) 0.0392 (10) 0.0260 (9) 0.0022 (10) 0.0003 (9) −0.0009 (8)
C15 0.0516 (14) 0.0482 (12) 0.0325 (10) 0.0086 (12) −0.0049 (11) −0.0062 (10)
O16 0.0690 (12) 0.0543 (10) 0.0397 (8) 0.0241 (10) −0.0051 (9) −0.0084 (7)
supporting information
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Acta Cryst. (2001). E57, o116–o117
C19 0.0720 (19) 0.0659 (17) 0.0626 (16) 0.0297 (17) −0.0152 (16) −0.0024 (14)
C20 0.0440 (12) 0.0425 (11) 0.0378 (11) −0.0012 (11) −0.0032 (11) 0.0081 (9)
C21 0.0704 (18) 0.0452 (13) 0.0610 (16) 0.0073 (14) −0.0120 (16) 0.0076 (11)
C22 0.0542 (15) 0.0527 (13) 0.0441 (12) 0.0013 (13) −0.0103 (12) 0.0048 (10)
C23 0.070 (2) 0.0601 (16) 0.0739 (19) 0.0127 (17) −0.0188 (18) 0.0142 (15)
O24 0.0727 (13) 0.0695 (12) 0.0564 (10) 0.0022 (11) −0.0275 (11) 0.0063 (10)
O25 0.0757 (13) 0.0805 (13) 0.0338 (8) 0.0208 (12) 0.0058 (9) −0.0108 (8)
O26 0.0654 (11) 0.0465 (9) 0.0357 (8) −0.0133 (9) −0.0100 (8) −0.0013 (7)
O27 0.0399 (8) 0.0663 (10) 0.0418 (8) 0.0062 (9) −0.0021 (7) 0.0143 (8)
C28 0.097 (3) 0.0426 (14) 0.101 (2) −0.0143 (17) −0.037 (2) 0.0130 (15)
C29 0.087 (2) 0.107 (3) 0.086 (2) 0.030 (2) −0.024 (2) −0.054 (2)
C30 0.0431 (12) 0.0481 (12) 0.0353 (10) −0.0009 (11) −0.0013 (10) 0.0075 (10)
O31 0.0581 (11) 0.0396 (8) 0.0541 (9) −0.0007 (8) −0.0170 (9) −0.0033 (7)
O32 0.0704 (12) 0.0416 (8) 0.0438 (8) 0.0012 (9) 0.0013 (9) 0.0082 (7)
O33 0.131 (2) 0.0753 (13) 0.0579 (12) 0.0085 (16) 0.0324 (15) 0.0096 (10)
Geometric parameters (Å, º)
C1—C2 1.309 (4) C12—H12B 0.970
C1—C10 1.501 (4) C13—C18 1.494 (3)
C1—H1 0.930 C13—C17 1.507 (3)
C2—C3 1.452 (4) C13—C14 1.515 (3)
C2—H2 0.930 C14—C15 1.475 (3)
C3—O33 1.209 (3) C14—C18 1.504 (3)
C3—O32 1.360 (3) C15—O25 1.203 (3)
C4—O31 1.460 (3) C15—O16 1.354 (3)
C4—C29 1.516 (4) O16—C17 1.469 (3)
C4—C28 1.521 (4) C17—C20 1.494 (3)
C4—C5 1.555 (3) C17—H17 0.980
C5—C6 1.526 (3) C18—H18A 0.970
C5—C10 1.542 (3) C18—H18B 0.970
C5—H5 0.980 C19—H19A 0.960
C6—C7 1.512 (3) C19—H19B 0.960
C6—H6A 0.970 C19—H19C 0.960
C6—H6B 0.970 C20—C22 1.341 (3)
C7—O31 1.415 (3) C20—C21 1.418 (3)
C7—O27 1.437 (3) C21—C23 1.332 (4)
C7—C30 1.546 (4) C21—H21 0.930
C8—O26 1.424 (3) C22—O24 1.355 (3)
C8—C14 1.504 (3) C22—H22 0.930
C8—C30 1.521 (3) C23—O24 1.362 (4)
C8—C9 1.528 (3) C23—H23 0.930
C9—O27 1.427 (3) O26—H26 0.820
C9—C11 1.512 (3) C28—H28A 0.960
C9—H9 0.980 C28—H28B 0.960
C10—O32 1.455 (3) C28—H28C 0.960
C10—C19 1.528 (4) C29—H29A 0.960
C11—H11A 0.970 C29—H29C 0.960
C11—H11B 0.970 C30—H30A 0.970
C12—C13 1.528 (3) C30—H30B 0.970
C12—H12A 0.970
C2—C1—C10 110.6 (3) C18—C13—C12 119.6 (2)
C2—C1—H1 124.7 C17—C13—C12 119.5 (2)
C10—C1—H1 124.7 C14—C13—C12 120.4 (2)
C1—C2—C3 108.9 (2) C15—C14—C18 111.7 (2)
C1—C2—H2 125.6 C15—C14—C8 118.29 (18)
C3—C2—H2 125.6 C18—C14—C8 127.33 (19)
O33—C3—O32 121.0 (3) C15—C14—C13 105.96 (18)
O33—C3—C2 130.8 (3) C18—C14—C13 59.34 (14)
O32—C3—C2 108.1 (2) C8—C14—C13 117.5 (2)
O31—C4—C29 107.9 (2) O25—C15—O16 121.3 (2)
O31—C4—C28 103.2 (3) O25—C15—C14 128.2 (2)
C29—C4—C28 111.3 (3) O16—C15—C14 110.48 (18)
O31—C4—C5 104.23 (18) C15—O16—C17 110.62 (17)
C29—C4—C5 111.3 (3) O16—C17—C20 108.5 (2)
C28—C4—C5 117.9 (2) O16—C17—C13 105.76 (17)
C6—C5—C10 112.87 (18) C20—C17—C13 118.06 (19)
C6—C5—C4 104.30 (19) O16—C17—H17 108.0
C10—C5—C4 119.2 (2) C20—C17—H17 108.0
C6—C5—H5 106.6 C13—C17—H17 108.0
C10—C5—H5 106.6 C13—C18—C14 60.70 (14)
C4—C5—H5 106.6 C13—C18—H18A 117.7
C7—C6—C5 103.17 (18) C14—C18—H18A 117.7
C7—C6—H6A 111.1 C13—C18—H18B 117.7
C5—C6—H6A 111.1 C14—C18—H18B 117.7
C7—C6—H6B 111.1 H18A—C18—H18B 114.8
C5—C6—H6B 111.1 C10—C19—H19A 109.5
H6A—C6—H6B 109.1 C10—C19—H19B 109.5
O31—C7—O27 110.14 (19) H19A—C19—H19B 109.5
O31—C7—C6 104.60 (18) C10—C19—H19C 109.5
O27—C7—C6 110.07 (19) H19A—C19—H19C 109.5
O31—C7—C30 108.1 (2) H19B—C19—H19C 109.5
O27—C7—C30 106.03 (17) C22—C20—C21 106.0 (2)
C6—C7—C30 117.8 (2) C22—C20—C17 128.2 (2)
O26—C8—C14 105.23 (17) C21—C20—C17 125.8 (2)
O26—C8—C30 111.68 (17) C23—C21—C20 106.7 (3)
C14—C8—C30 120.60 (19) C23—C21—H21 126.7
O26—C8—C9 108.57 (19) C20—C21—H21 126.7
C14—C8—C9 110.38 (16) C20—C22—O24 110.8 (2)
C30—C8—C9 100.00 (17) C20—C22—H22 124.6
O27—C9—C11 114.72 (19) O24—C22—H22 124.6
O27—C9—C8 102.44 (16) C21—C23—O24 110.6 (3)
C11—C9—C8 111.17 (19) C21—C23—H23 124.7
supporting information
sup-7
Acta Cryst. (2001). E57, o116–o117
C11—C9—H9 109.4 C22—O24—C23 106.0 (2)
C8—C9—H9 109.4 C8—O26—H26 109.5
O32—C10—C1 102.12 (18) C9—O27—C7 106.29 (17)
O32—C10—C19 108.4 (2) C4—C28—H28A 109.5
C1—C10—C19 110.9 (2) C4—C28—H28B 109.5
O32—C10—C5 110.5 (2) H28A—C28—H28B 109.5
C1—C10—C5 110.65 (19) C4—C28—H28C 109.5
C19—C10—C5 113.6 (2) H28A—C28—H28C 109.5
C9—C11—C12 109.3 (2) H28B—C28—H28C 109.5
C9—C11—H11A 109.8 C4—C29—H29A 109.5
C12—C11—H11A 109.8 C4—C29—H29B 109.5
C9—C11—H11B 109.8 H29A—C29—H29B 109.5
C12—C11—H11B 109.8 C4—C29—H29C 109.5
H11A—C11—H11B 108.3 H29A—C29—H29C 109.5
C13—C12—C11 116.26 (17) H29B—C29—H29C 109.5
C13—C12—H12A 108.2 C8—C30—C7 103.46 (19)
C11—C12—H12A 108.2 C8—C30—H30A 111.1
C13—C12—H12B 108.2 C7—C30—H30A 111.1
C11—C12—H12B 108.2 C8—C30—H30B 111.1
H12A—C12—H12B 107.4 C7—C30—H30B 111.1
C18—C13—C17 116.8 (2) H30A—C30—H30B 109.0
C18—C13—C14 59.95 (14) C7—O31—C4 111.55 (19)
C17—C13—C14 105.25 (18) C3—O32—C10 110.2 (2)
C10—C1—C2—C3 2.0 (3) C8—C14—C15—O25 45.0 (4)
C1—C2—C3—O33 177.4 (3) C13—C14—C15—O25 179.3 (3)
C1—C2—C3—O32 −2.0 (3) C18—C14—C15—O16 60.4 (3)
O31—C4—C5—C6 −13.5 (2) C8—C14—C15—O16 −136.7 (2)
C29—C4—C5—C6 −129.6 (2) C13—C14—C15—O16 −2.4 (3)
C28—C4—C5—C6 100.1 (3) O25—C15—O16—C17 −170.9 (3)
O31—C4—C5—C10 −140.6 (2) C14—C15—O16—C17 10.7 (3)
C29—C4—C5—C10 103.4 (3) C15—O16—C17—C20 −142.1 (2)
C28—C4—C5—C10 −26.9 (4) C15—O16—C17—C13 −14.5 (3)
C10—C5—C6—C7 160.3 (2) C18—C13—C17—O16 −51.5 (2)
C4—C5—C6—C7 29.4 (2) C14—C13—C17—O16 12.2 (2)
C5—C6—C7—O31 −35.1 (2) C12—C13—C17—O16 151.3 (2)
C5—C6—C7—O27 83.2 (2) C18—C13—C17—C20 70.2 (3)
C5—C6—C7—C30 −155.1 (2) C14—C13—C17—C20 133.8 (2)
O26—C8—C9—O27 −71.4 (2) C12—C13—C17—C20 −87.0 (3)
C14—C8—C9—O27 173.78 (17) C17—C13—C18—C14 92.8 (2)
C30—C8—C9—O27 45.7 (2) C12—C13—C18—C14 −110.1 (2)
O26—C8—C9—C11 51.6 (2) C15—C14—C18—C13 −96.2 (2)
C14—C8—C9—C11 −63.2 (2) C8—C14—C18—C13 102.8 (2)
C30—C8—C9—C11 168.69 (19) O16—C17—C20—C22 121.1 (3)
C2—C1—C10—O32 −1.2 (3) C13—C17—C20—C22 0.9 (4)
C2—C1—C10—C19 114.1 (3) O16—C17—C20—C21 −60.9 (3)
C2—C1—C10—C5 −118.8 (3) C13—C17—C20—C21 178.8 (2)
C4—C5—C10—O32 60.5 (3) C17—C20—C21—C23 −178.1 (3)
C6—C5—C10—C1 50.0 (3) C21—C20—C22—O24 −0.6 (3)
C4—C5—C10—C1 172.9 (2) C17—C20—C22—O24 177.6 (2)
C6—C5—C10—C19 175.5 (2) C20—C21—C23—O24 0.2 (4)
C4—C5—C10—C19 −61.6 (3) C20—C22—O24—C23 0.7 (3)
O27—C9—C11—C12 179.6 (2) C21—C23—O24—C22 −0.5 (4)
C8—C9—C11—C12 63.9 (3) C11—C9—O27—C7 −163.94 (19)
C9—C11—C12—C13 −36.9 (3) C8—C9—O27—C7 −43.4 (2)
C11—C12—C13—C18 81.8 (3) O31—C7—O27—C9 −93.8 (2)
C11—C12—C13—C17 −121.6 (2) C6—C7—O27—C9 151.35 (19)
C11—C12—C13—C14 11.3 (4) C30—C7—O27—C9 22.9 (2)
O26—C8—C14—C15 46.8 (2) O26—C8—C30—C7 83.8 (2)
C30—C8—C14—C15 −80.4 (3) C14—C8—C30—C7 −151.90 (19)
C9—C8—C14—C15 163.8 (2) C9—C8—C30—C7 −30.9 (2)
O26—C8—C14—C18 −153.3 (2) O31—C7—C30—C8 124.71 (19)
C30—C8—C14—C18 79.4 (3) O27—C7—C30—C8 6.6 (2)
C9—C8—C14—C18 −36.3 (3) C6—C7—C30—C8 −117.1 (2)
O26—C8—C14—C13 −82.3 (2) O27—C7—O31—C4 −90.2 (2)
C30—C8—C14—C13 150.39 (19) C6—C7—O31—C4 28.0 (3)
C9—C8—C14—C13 34.6 (3) C30—C7—O31—C4 154.34 (19)
C18—C13—C14—C15 106.1 (2) C29—C4—O31—C7 109.4 (3)
C17—C13—C14—C15 −6.3 (3) C28—C4—O31—C7 −132.6 (2)
C12—C13—C14—C15 −145.0 (2) C5—C4—O31—C7 −8.9 (3)
C17—C13—C14—C18 −112.5 (2) O33—C3—O32—C10 −178.3 (3)
C12—C13—C14—C18 108.8 (2) C2—C3—O32—C10 1.2 (3)
C18—C13—C14—C8 −119.1 (2) C1—C10—O32—C3 −0.1 (3)
C17—C13—C14—C8 128.4 (2) C19—C10—O32—C3 −117.2 (2)
C12—C13—C14—C8 −10.3 (3) C5—C10—O32—C3 117.7 (2)
C18—C14—C15—O25 −117.9 (3)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
C28—H28C···O32 0.96 2.41 2.894 (4) 111
O26—H26···O25i 0.82 2.00 2.805 (2) 169
C23—H23···O31ii 0.93 2.43 3.283 (3) 152
