organic papers
o788
Suitchmezianet al. C25H31FO8CHCl3 doi:10.1107/S1600536806001711 Acta Cryst.(2006). E62, o788–o790
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368
Triamcinolone diacetate chloroform solvate
Viktor Suitchmezian, Inke Jess and Christian Na¨ther*
Institut fu¨r Anorganische Chemie, Christian-Albrechts-Universita¨t Kiel, Olshausenstrasse 40, D-24098 Kiel, Germany
Correspondence e-mail: cnaether@ac.uni-kiel.de
Key indicators
Single-crystal X-ray study T= 170 K
Mean(C–C) = 0.004 A˚ Rfactor = 0.047 wRfactor = 0.122
Data-to-parameter ratio = 17.7
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
Received 4 January 2006 Accepted 16 January 2006
#2006 International Union of Crystallography All rights reserved
In the crystal structure of the title compound, 16 ,21-diacetoxy-9-fluoro-11,17 -dihydroxy-1,4-pregnadiene-3,20-dione chloroform solvate, C25H31FO8CHCl3, the molecules
are connectedviaO—H O hydrogen bonding. Channels, in which the chloroform molecules are located, are formed in the direction of the crystallographicaaxis.
Comment
Triamcinolone diacetate, also known as 16,21-diacetoxy-9 -fluoro-11,17-dihydroxyl-1,4-pregnadiene-3,20-dione or 9 -fluoro-16-prednisolone-16,21-diacetate, belongs to the class of glucocorticoids which are adrenal cortical hormones.
Synthetic and natural glucocorticoids are amongst the most effective drugs against inflammatory and immune responses (Barnes, 1998; Buttgereit, 2000; Falkensteinet al., 2000). They are essential for chronic inflammatory disease therapy for multiple sclerosis, rheumatoid arthritis, allergic asthma and Morbus Crohn, and also for severe symptoms of psoriasis and allergic dermatitis. In the human body, glucocorticoids are a part of many catabolic processes. This is the reason why, in long-term treatment, glucocorticoids show some adverse effects, such as decomposition of skeletal muscles and skin atrophy. In some cases, a reallocation of adipose tissues (Cushing’s syndrome) and osteoporosis are observed. One very important glucocorticoid is triamcinolone, which has been used in therapy for several decades, mainly as the acet-onide and the diacetate. Despite their great importance, no crystal structures are available in the Cambridge Structural Database (CSD) for the diacetate or the pure triamcinolone (Allen, 2002; ConQuest Version 1.6, CSD Version 5.26 of November 2004). The acetonide has been structurally char-acterized only as a methanol solvate (Surcouf, 1979).
In the crystal structure of the title compound, (I) (Fig. 1), the molecules are connectedviaO—H O hydrogen bonding between the hydroxyl H atom at O2 and carbonyl atom O8, and between the hydroxyl H atom at O3 and carbonyl atom O1 (Fig. 2 and Table 1). The O O distances and O—H O angles show that these are strong interactions (Table 1). In the direction of the a axis, channels are formed in which the chloroform molecules are located (Fig. 2).
Experimental
The title compound was obtained from HPP (Hommel Pharmaceu-ticals Production GmbH, Germany) as an enantiopure compound and was recrystallized from chloroform. The homogeneity was confirmed by X-ray powder diffraction. The compound decomposes at room temperature within a few days.
Crystal data
C25H31FO8CHCl3
Mr= 597.87
Orthorhombic,P212121
a= 8.0465 (4) A˚
b= 14.5972 (7) A˚
c= 23.7454 (14) A˚
V= 2789.0 (3) A˚3
Z= 4
Dx= 1.424 Mg m 3
MoKradiation Cell parameters from 8000
reflections = 11.6–25
= 0.38 mm1
T= 170 (2) K Block, colourless 0.20.20.15 mm
Data collection
Stoe IPDS-1 diffractometer ’scans
Absorption correction: none 17821 measured reflections 6150 independent reflections 4683 reflections withI> 2(I)
Rint= 0.054 max= 27.1
h=10!8
k=18!16
l=30!30
Refinement
Refinement onF2
R[F2> 2(F2)] = 0.047
wR(F2) = 0.122
S= 1.03 6150 reflections 347 parameters
H-atom parameters constrained
w= 1/[2(F
o2) + (0.0585P)2
+ 1.0803P]
whereP= (Fo2+ 2Fc2)/3
(/)max< 0.001 max= 0.59 e A˚
3 min=0.45 e A˚ 3
Extinction correction:SHELXL97
Extinction coefficient: 0.0083 (12) Absolute structure: Flack (1983),
with 2672 Friedel pairs Flack parameter: 0.06 (8)
[image:2.610.314.566.71.289.2] [image:2.610.92.532.294.722.2]organic papers
Figure 1
View of the asymmetric unit of (I), showing the atom labelling scheme and with displacement ellipsoids drawn at the 50% probability level.
Figure 2
Table 1
Hydrogen-bond geometry (A˚ ,).
D—H A D—H H A D A D—H A
O2—H1O2 O8i
0.84 1.92 2.750 (3) 169
O3—H1O3 O1ii
0.84 1.95 2.747 (3) 157
Symmetry codes: (i)xþ1;yþ1 2;zþ
3 2; (ii)xþ
1 2;yþ
3 2;zþ1.
The H atoms were positioned with idealized geometry and were refined with fixed isotropic displacement parameters [Uiso(H) = 1.2Ueq(C)] using a riding model, with C—H = 0.95 A˚ for olefin, 1.00 A˚ for methine and 0.99 A˚ for methylene H atoms. The positions of the methyl (except C18 and C19) and hydroxy H atoms were idealized (C—H = 0.98 A˚ and O—H = 0.84 A˚), then refined with fixed isotropic displacement parameters [Uiso(H)= 1.5Ueq(C,O)] as rigid groups allowed to rotate but not tip. Although the absolute configuration was known in advance, it was additionally determined on the basis of anomalous scattering effects.
Data collection:IPDS Program Package(Stoe & Cie, 1998); cell refinement:IPDS Program Package; data reduction:IPDS Program Package; program(s) used to solve structure:SHELXS97(Sheldrick,
1997); program(s) used to refine structure:SHELXL97(Sheldrick, 1997); molecular graphics:XPinSHELXTL(Bruker, 1998); software used to prepare material for publication:CIFTABinSHELXTL.
This work was supported by the state of Schleswig– Holstein. We are very grateful to Professor Dr Wolfgang Bensch for financial support and the opportunity to use his experimental equipment.
References
Allen, F. H. (2002).Acta Cryst.B58, 380–388. Barnes, P. J. (1998).Clin. Sci.94, 557–572.
Bruker (1998). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA.
Buttgereit, F. (2000).Z. Rheumatol.59, 119–123.
Falkenstein, E., Tilmann, H. C., Christ, M., Feuring, M. & Wehling, M. (2000).
Pharmacol. Rev.52, 513–556.
Flack, H. D. (1983).Acta Cryst.A39, 876–881.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Go¨ttingen, Germany.
Stoe & Cie (1998). IPDS Program Package. Version 2.89. Stoe & Cie, Darmstadt, Germany.
Surcouf, E. (1979).Acta Cryst.B35, 2638–2641.
organic papers
o790
Suitchmezianet al. Csupporting information
sup-1 Acta Cryst. (2006). E62, o788–o790
supporting information
Acta Cryst. (2006). E62, o788–o790 [https://doi.org/10.1107/S1600536806001711]
Triamcinolone diacetate chloroform solvate
Viktor Suitchmezian, Inke Jess and Christian N
ä
ther
16α,21-diacetoxy-9α-fluoro-11β,17α-dihydroxy-1,4-pregnadiene-3,20-dione chloroform solvate
Crystal data
C25H31FO8·CHCl3 Mr = 597.87
Orthorhombic, P212121
Hall symbol: P 2ac 2ab
a = 8.0465 (4) Å
b = 14.5972 (7) Å
c = 23.7454 (14) Å
V = 2789.0 (3) Å3
Z = 4
F(000) = 1248
Dx = 1.424 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 8000 reflections
θ = 11.6–25°
µ = 0.38 mm−1
T = 170 K
Block, colourless 0.2 × 0.2 × 0.15 mm
Data collection
IPDS-1
diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
φ scans
17821 measured reflections 6150 independent reflections
4683 reflections with I > 2σ(I) Rint = 0.054
θmax = 27.1°, θmin = 2.7°
h = −10→8
k = −18→16
l = −30→30
Refinement
Refinement on F2
Least-squares matrix: full R[F2 > 2σ(F2)] = 0.047 wR(F2) = 0.122
S = 1.03
6150 reflections 347 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H-atom parameters constrained w = 1/[σ2(F
o2) + (0.0585P)2 + 1.0803P] where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001 Δρmax = 0.59 e Å−3 Δρmin = −0.45 e Å−3
Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 Extinction coefficient: 0.0083 (12) Absolute structure: Flack (1983) Absolute structure parameter: 0.06 (8)
Special details
supporting information
sup-2 Acta Cryst. (2006). E62, o788–o790
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
O1 −0.0183 (4) 0.97252 (17) 0.45783 (8) 0.0456 (7)
O2 0.1598 (3) 0.84146 (16) 0.72423 (8) 0.0290 (5)
H1O2 0.2269 0.8510 0.7507 0.043*
O3 0.5455 (2) 0.57657 (13) 0.65175 (7) 0.0202 (4)
H1O3 0.5024 0.5550 0.6224 0.030*
O4 0.4981 (3) 0.52941 (15) 0.79451 (7) 0.0287 (5)
O5 0.8104 (3) 0.60134 (14) 0.79262 (8) 0.0275 (5)
O6 0.6813 (4) 0.73584 (19) 0.79491 (11) 0.0570 (8)
O7 0.3769 (3) 0.42113 (13) 0.64608 (7) 0.0218 (4)
O8 0.5966 (3) 0.38785 (14) 0.69968 (8) 0.0303 (5)
F1 0.2131 (2) 0.77127 (11) 0.58201 (6) 0.0221 (4)
C1 −0.0230 (4) 0.9364 (2) 0.50524 (10) 0.0266 (7)
C2 0.0622 (4) 0.9803 (2) 0.55238 (11) 0.0281 (6)
H2 0.1179 1.0370 0.5467 0.034*
C3 0.0628 (4) 0.9421 (2) 0.60301 (11) 0.0257 (6)
H3 0.1189 0.9734 0.6325 0.031*
C4 −0.0190 (4) 0.85279 (19) 0.61684 (10) 0.0204 (6)
C5 0.1182 (4) 0.78061 (19) 0.63230 (10) 0.0184 (6)
C6 0.2486 (4) 0.81372 (19) 0.67543 (11) 0.0218 (6)
H6 0.3056 0.8688 0.6594 0.026*
C7 0.3805 (4) 0.7411 (2) 0.68746 (11) 0.0215 (6)
H7A 0.4530 0.7349 0.6540 0.026*
H7B 0.4505 0.7621 0.7192 0.026*
C8 0.3089 (3) 0.64724 (19) 0.70195 (10) 0.0181 (5)
C9 0.4345 (4) 0.56541 (19) 0.69759 (10) 0.0190 (5)
C10 0.3171 (3) 0.4810 (2) 0.68987 (10) 0.0202 (5)
H10 0.3042 0.4470 0.7261 0.024*
C11 0.1487 (4) 0.5187 (2) 0.66976 (12) 0.0240 (6)
H11A 0.1085 0.4850 0.6363 0.029*
H11B 0.0641 0.5146 0.6999 0.029*
C12 0.1872 (3) 0.61828 (19) 0.65535 (11) 0.0197 (5)
H12 0.2534 0.6167 0.6197 0.024*
C13 0.0456 (4) 0.68581 (18) 0.64507 (11) 0.0197 (5)
H13 −0.0228 0.6901 0.6801 0.024*
C14 −0.0660 (4) 0.6519 (2) 0.59694 (12) 0.0262 (6)
H14A 0.0048 0.6350 0.5645 0.031*
H14B −0.1251 0.5960 0.6095 0.031*
C15 −0.1946 (4) 0.7228 (2) 0.57750 (14) 0.0306 (7)
H15A −0.2489 0.7013 0.5425 0.037*
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sup-3 Acta Cryst. (2006). E62, o788–o790
C16 −0.1121 (4) 0.8130 (2) 0.56707 (11) 0.0238 (6)
C17 −0.1103 (4) 0.8522 (2) 0.51639 (11) 0.0267 (6)
H17 −0.1688 0.8234 0.4865 0.032*
C18 −0.1447 (4) 0.8721 (2) 0.66478 (12) 0.0333 (8)
H18A −0.2015 0.8152 0.6751 0.050*
H18B −0.2267 0.9172 0.6519 0.050*
H18C −0.0855 0.8964 0.6976 0.050*
C19 0.2264 (4) 0.6485 (2) 0.76054 (11) 0.0264 (6)
H19A 0.1813 0.5876 0.7690 0.040*
H19B 0.1363 0.6936 0.7608 0.040*
H19C 0.3093 0.6650 0.7890 0.040*
C20 0.5476 (4) 0.55670 (19) 0.74946 (10) 0.0205 (5)
C21 0.7262 (4) 0.5850 (2) 0.74056 (11) 0.0261 (6)
H21A 0.7850 0.5363 0.7195 0.031*
H21B 0.7292 0.6415 0.7175 0.031*
C22 0.7784 (4) 0.6843 (2) 0.81543 (12) 0.0317 (7)
C23 0.8769 (6) 0.7002 (3) 0.86730 (16) 0.0507 (11)
H23A 0.9478 0.6469 0.8746 0.076*
H23B 0.8015 0.7094 0.8992 0.076*
H23C 0.9463 0.7547 0.8624 0.076*
C24 0.5208 (4) 0.37819 (19) 0.65628 (11) 0.0245 (6)
C25 0.5737 (5) 0.3199 (2) 0.60850 (13) 0.0371 (8)
H25A 0.6830 0.2935 0.6166 0.056*
H25B 0.5803 0.3571 0.5742 0.056*
H25C 0.4928 0.2705 0.6030 0.056*
Cl1 0.75360 (18) 0.16996 (9) 0.50858 (5) 0.0702 (4)
Cl2 0.43668 (17) 0.10105 (11) 0.47032 (5) 0.0741 (4)
Cl3 0.56404 (19) 0.04954 (9) 0.57946 (5) 0.0718 (4)
C26 0.6164 (6) 0.0769 (3) 0.50941 (17) 0.0529 (10)
H26 0.6733 0.0229 0.4921 0.063*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
O1 0.082 (2) 0.0385 (13) 0.0167 (9) 0.0030 (14) −0.0052 (11) 0.0058 (9)
O2 0.0291 (12) 0.0355 (12) 0.0224 (9) 0.0079 (11) −0.0059 (8) −0.0120 (9)
O3 0.0188 (10) 0.0264 (10) 0.0155 (8) −0.0011 (9) 0.0042 (7) 0.0004 (7)
O4 0.0309 (11) 0.0395 (12) 0.0157 (8) −0.0026 (10) 0.0011 (8) 0.0043 (8)
O5 0.0278 (11) 0.0256 (11) 0.0292 (10) 0.0027 (9) −0.0103 (9) −0.0017 (8)
O6 0.076 (2) 0.0403 (15) 0.0551 (15) 0.0257 (15) −0.0329 (15) −0.0143 (12)
O7 0.0268 (11) 0.0192 (10) 0.0194 (8) 0.0018 (9) −0.0039 (7) 0.0008 (7)
O8 0.0336 (13) 0.0258 (11) 0.0316 (10) 0.0037 (10) −0.0097 (9) 0.0051 (9)
F1 0.0242 (9) 0.0244 (8) 0.0176 (7) 0.0001 (7) 0.0066 (6) −0.0035 (6)
C1 0.0377 (18) 0.0264 (14) 0.0159 (11) 0.0077 (14) −0.0023 (11) −0.0012 (10)
C2 0.0373 (17) 0.0251 (15) 0.0220 (12) −0.0019 (15) −0.0031 (12) −0.0003 (11)
C3 0.0357 (17) 0.0217 (13) 0.0197 (12) 0.0014 (14) −0.0078 (12) −0.0044 (10)
C4 0.0252 (15) 0.0199 (13) 0.0161 (11) 0.0041 (13) 0.0007 (10) −0.0022 (10)
supporting information
sup-4 Acta Cryst. (2006). E62, o788–o790
C6 0.0227 (15) 0.0197 (13) 0.0231 (12) 0.0001 (13) −0.0006 (11) −0.0027 (10)
C7 0.0198 (14) 0.0225 (14) 0.0221 (12) −0.0023 (12) 0.0009 (10) −0.0022 (10)
C8 0.0178 (13) 0.0201 (13) 0.0163 (11) 0.0005 (11) 0.0020 (10) 0.0002 (10)
C9 0.0208 (13) 0.0221 (13) 0.0140 (11) −0.0032 (12) 0.0040 (10) 0.0018 (10)
C10 0.0209 (13) 0.0228 (13) 0.0169 (11) −0.0007 (12) 0.0019 (10) 0.0001 (10)
C11 0.0192 (14) 0.0203 (13) 0.0325 (14) −0.0037 (12) −0.0014 (11) 0.0022 (11)
C12 0.0180 (13) 0.0204 (13) 0.0206 (12) −0.0018 (12) 0.0004 (10) 0.0001 (10)
C13 0.0171 (13) 0.0193 (13) 0.0226 (12) −0.0008 (12) −0.0008 (10) 0.0008 (10)
C14 0.0217 (15) 0.0238 (14) 0.0330 (14) 0.0011 (13) −0.0068 (12) −0.0016 (12)
C15 0.0224 (16) 0.0321 (16) 0.0372 (15) −0.0016 (14) −0.0083 (13) 0.0039 (13)
C16 0.0188 (14) 0.0250 (14) 0.0275 (13) 0.0048 (12) −0.0046 (11) −0.0028 (11)
C17 0.0343 (17) 0.0275 (15) 0.0184 (12) 0.0055 (14) −0.0105 (11) −0.0056 (11)
C18 0.0312 (18) 0.046 (2) 0.0230 (13) 0.0150 (16) 0.0029 (12) 0.0032 (13)
C19 0.0268 (16) 0.0310 (15) 0.0212 (12) 0.0019 (14) 0.0068 (11) −0.0010 (11)
C20 0.0208 (14) 0.0195 (13) 0.0211 (12) 0.0000 (12) 0.0012 (11) 0.0000 (10)
C21 0.0188 (14) 0.0336 (16) 0.0258 (13) −0.0017 (13) −0.0015 (11) −0.0034 (11)
C22 0.0341 (18) 0.0294 (17) 0.0316 (15) 0.0021 (15) −0.0049 (13) −0.0036 (12)
C23 0.066 (3) 0.044 (2) 0.0424 (19) 0.000 (2) −0.0219 (19) −0.0143 (16)
C24 0.0287 (16) 0.0181 (13) 0.0268 (13) 0.0004 (13) −0.0019 (12) 0.0052 (11)
C25 0.043 (2) 0.0351 (18) 0.0332 (15) 0.0094 (18) 0.0031 (15) −0.0038 (13)
Cl1 0.0775 (9) 0.0749 (8) 0.0581 (6) −0.0044 (7) 0.0235 (6) −0.0096 (5)
Cl2 0.0620 (7) 0.1045 (10) 0.0557 (6) 0.0281 (8) −0.0016 (5) 0.0062 (6)
Cl3 0.0846 (9) 0.0693 (7) 0.0616 (6) 0.0121 (7) 0.0006 (6) 0.0265 (5)
C26 0.054 (3) 0.051 (2) 0.054 (2) 0.020 (2) 0.0065 (18) −0.0024 (18)
Geometric parameters (Å, º)
O1—C1 1.244 (3) C11—C12 1.525 (4)
O2—C6 1.421 (3) C11—H11A 0.9900
O2—H1O2 0.8400 C11—H11B 0.9900
O3—C9 1.418 (3) C12—C13 1.527 (4)
O3—H1O3 0.8400 C12—H12 1.0000
O4—C20 1.209 (3) C13—C14 1.535 (4)
O5—C22 1.351 (4) C13—H13 1.0000
O5—C21 1.430 (3) C14—C15 1.534 (4)
O6—C22 1.189 (4) C14—H14A 0.9900
O7—C24 1.338 (4) C14—H14B 0.9900
O7—C10 1.441 (3) C15—C16 1.496 (4)
O8—C24 1.206 (3) C15—H15A 0.9900
F1—C5 1.424 (3) C15—H15B 0.9900
C1—C17 1.441 (5) C16—C17 1.332 (4)
C1—C2 1.461 (4) C17—H17 0.9500
C2—C3 1.326 (4) C18—H18A 0.9800
C2—H2 0.9500 C18—H18B 0.9800
C3—C4 1.497 (4) C18—H18C 0.9800
C3—H3 0.9500 C19—H19A 0.9800
C4—C16 1.515 (4) C19—H19B 0.9800
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sup-5 Acta Cryst. (2006). E62, o788–o790
C4—C5 1.570 (4) C20—C21 1.510 (4)
C5—C13 1.533 (4) C21—H21A 0.9900
C5—C6 1.544 (4) C21—H21B 0.9900
C6—C7 1.527 (4) C22—C23 1.483 (5)
C6—H6 1.0000 C23—H23A 0.9800
C7—C8 1.525 (4) C23—H23B 0.9800
C7—H7A 0.9900 C23—H23C 0.9800
C7—H7B 0.9900 C24—C25 1.480 (4)
C8—C12 1.537 (4) C25—H25A 0.9800
C8—C19 1.542 (3) C25—H25B 0.9800
C8—C9 1.568 (4) C25—H25C 0.9800
C9—C20 1.537 (4) Cl1—C26 1.750 (5)
C9—C10 1.563 (4) Cl2—C26 1.754 (5)
C10—C11 1.539 (4) Cl3—C26 1.762 (4)
C10—H10 1.0000 C26—H26 1.0000
C6—O2—H1O2 109.5 C12—C13—C14 110.4 (2)
C9—O3—H1O3 109.5 C5—C13—C14 111.5 (2)
C22—O5—C21 113.9 (2) C12—C13—H13 108.5
C24—O7—C10 116.3 (2) C5—C13—H13 108.5
O1—C1—C17 122.9 (3) C14—C13—H13 108.5
O1—C1—C2 119.6 (3) C15—C14—C13 113.7 (2)
C17—C1—C2 117.5 (2) C15—C14—H14A 108.8
C3—C2—C1 120.8 (3) C13—C14—H14A 108.8
C3—C2—H2 119.6 C15—C14—H14B 108.8
C1—C2—H2 119.6 C13—C14—H14B 108.8
C2—C3—C4 124.3 (3) H14A—C14—H14B 107.7
C2—C3—H3 117.8 C16—C15—C14 110.1 (3)
C4—C3—H3 117.8 C16—C15—H15A 109.6
C3—C4—C16 112.3 (2) C14—C15—H15A 109.6
C3—C4—C18 106.8 (2) C16—C15—H15B 109.6
C16—C4—C18 108.7 (3) C14—C15—H15B 109.6
C3—C4—C5 109.1 (2) H15A—C15—H15B 108.2
C16—C4—C5 105.8 (2) C17—C16—C15 122.1 (3)
C18—C4—C5 114.2 (2) C17—C16—C4 122.4 (3)
F1—C5—C13 106.5 (2) C15—C16—C4 115.3 (2)
F1—C5—C6 102.8 (2) C16—C17—C1 122.5 (3)
C13—C5—C6 114.2 (2) C16—C17—H17 118.8
F1—C5—C4 104.19 (19) C1—C17—H17 118.8
C13—C5—C4 112.6 (2) C4—C18—H18A 109.5
C6—C5—C4 115.0 (2) C4—C18—H18B 109.5
O2—C6—C7 113.3 (2) H18A—C18—H18B 109.5
O2—C6—C5 106.7 (2) C4—C18—H18C 109.5
C7—C6—C5 112.3 (2) H18A—C18—H18C 109.5
O2—C6—H6 108.1 H18B—C18—H18C 109.5
C7—C6—H6 108.1 C8—C19—H19A 109.5
C5—C6—H6 108.1 C8—C19—H19B 109.5
supporting information
sup-6 Acta Cryst. (2006). E62, o788–o790
C8—C7—H7A 108.8 C8—C19—H19C 109.5
C6—C7—H7A 108.8 H19A—C19—H19C 109.5
C8—C7—H7B 108.8 H19B—C19—H19C 109.5
C6—C7—H7B 108.8 O4—C20—C21 121.8 (2)
H7A—C7—H7B 107.7 O4—C20—C9 122.8 (3)
C7—C8—C12 109.0 (2) C21—C20—C9 115.4 (2)
C7—C8—C19 110.8 (2) O5—C21—C20 112.1 (2)
C12—C8—C19 112.3 (2) O5—C21—H21A 109.2
C7—C8—C9 115.2 (2) C20—C21—H21A 109.2
C12—C8—C9 98.8 (2) O5—C21—H21B 109.2
C19—C8—C9 110.2 (2) C20—C21—H21B 109.2
O3—C9—C20 104.6 (2) H21A—C21—H21B 107.9
O3—C9—C10 112.4 (2) O6—C22—O5 121.9 (3)
C20—C9—C10 112.8 (2) O6—C22—C23 126.3 (3)
O3—C9—C8 111.7 (2) O5—C22—C23 111.8 (3)
C20—C9—C8 113.1 (2) C22—C23—H23A 109.5
C10—C9—C8 102.6 (2) C22—C23—H23B 109.5
O7—C10—C11 106.7 (2) H23A—C23—H23B 109.5
O7—C10—C9 111.2 (2) C22—C23—H23C 109.5
C11—C10—C9 106.7 (2) H23A—C23—H23C 109.5
O7—C10—H10 110.7 H23B—C23—H23C 109.5
C11—C10—H10 110.7 O8—C24—O7 122.5 (3)
C9—C10—H10 110.7 O8—C24—C25 125.2 (3)
C12—C11—C10 103.4 (2) O7—C24—C25 112.3 (2)
C12—C11—H11A 111.1 C24—C25—H25A 109.5
C10—C11—H11A 111.1 C24—C25—H25B 109.5
C12—C11—H11B 111.1 H25A—C25—H25B 109.5
C10—C11—H11B 111.1 C24—C25—H25C 109.5
H11A—C11—H11B 109.1 H25A—C25—H25C 109.5
C11—C12—C13 120.0 (2) H25B—C25—H25C 109.5
C11—C12—C8 103.3 (2) Cl1—C26—Cl2 111.0 (2)
C13—C12—C8 114.4 (2) Cl1—C26—Cl3 109.7 (2)
C11—C12—H12 106.1 Cl2—C26—Cl3 110.3 (3)
C13—C12—H12 106.1 Cl1—C26—H26 108.6
C8—C12—H12 106.1 Cl2—C26—H26 108.6
C12—C13—C5 109.3 (2) Cl3—C26—H26 108.6
O1—C1—C2—C3 −178.2 (3) C10—C11—C12—C8 −38.6 (3)
C17—C1—C2—C3 2.0 (5) C7—C8—C12—C11 170.8 (2)
C1—C2—C3—C4 0.6 (5) C19—C8—C12—C11 −66.0 (3)
C2—C3—C4—C16 −3.3 (4) C9—C8—C12—C11 50.2 (2)
C2—C3—C4—C18 −122.4 (3) C7—C8—C12—C13 −57.1 (3)
C2—C3—C4—C5 113.7 (3) C19—C8—C12—C13 66.1 (3)
C3—C4—C5—F1 −63.0 (2) C9—C8—C12—C13 −177.7 (2)
C16—C4—C5—F1 58.1 (3) C11—C12—C13—C5 179.2 (2)
C18—C4—C5—F1 177.6 (2) C8—C12—C13—C5 55.6 (3)
C3—C4—C5—C13 −177.9 (2) C11—C12—C13—C14 −57.8 (3)
supporting information
sup-7 Acta Cryst. (2006). E62, o788–o790
C18—C4—C5—C13 62.6 (3) F1—C5—C13—C12 62.2 (3)
C3—C4—C5—C6 48.8 (3) C6—C5—C13—C12 −50.5 (3)
C16—C4—C5—C6 169.8 (2) C4—C5—C13—C12 175.8 (2)
C18—C4—C5—C6 −70.6 (3) F1—C5—C13—C14 −60.0 (3)
F1—C5—C6—O2 169.3 (2) C6—C5—C13—C14 −172.8 (2)
C13—C5—C6—O2 −75.8 (3) C4—C5—C13—C14 53.6 (3)
C4—C5—C6—O2 56.7 (3) C12—C13—C14—C15 −170.7 (2)
F1—C5—C6—C7 −66.1 (3) C5—C13—C14—C15 −49.1 (3)
C13—C5—C6—C7 48.9 (3) C13—C14—C15—C16 49.5 (3)
C4—C5—C6—C7 −178.6 (2) C14—C15—C16—C17 117.8 (3)
O2—C6—C7—C8 70.7 (3) C14—C15—C16—C4 −57.4 (3)
C5—C6—C7—C8 −50.3 (3) C3—C4—C16—C17 3.7 (4)
C6—C7—C8—C12 53.3 (3) C18—C4—C16—C17 121.7 (3)
C6—C7—C8—C19 −70.7 (3) C5—C4—C16—C17 −115.2 (3)
C6—C7—C8—C9 163.2 (2) C3—C4—C16—C15 179.0 (3)
C7—C8—C9—O3 −37.0 (3) C18—C4—C16—C15 −63.0 (3)
C12—C8—C9—O3 78.9 (2) C5—C4—C16—C15 60.1 (3)
C19—C8—C9—O3 −163.3 (2) C15—C16—C17—C1 −176.4 (3)
C7—C8—C9—C20 80.6 (3) C4—C16—C17—C1 −1.5 (5)
C12—C8—C9—C20 −163.5 (2) O1—C1—C17—C16 178.7 (3)
C19—C8—C9—C20 −45.7 (3) C2—C1—C17—C16 −1.6 (5)
C7—C8—C9—C10 −157.6 (2) O3—C9—C20—O4 −165.7 (3)
C12—C8—C9—C10 −41.7 (2) C10—C9—C20—O4 −43.3 (4)
C19—C8—C9—C10 76.0 (2) C8—C9—C20—O4 72.6 (3)
C24—O7—C10—C11 −177.6 (2) O3—C9—C20—C21 14.5 (3)
C24—O7—C10—C9 66.4 (3) C10—C9—C20—C21 136.9 (2)
O3—C9—C10—O7 15.1 (3) C8—C9—C20—C21 −107.2 (3)
C20—C9—C10—O7 −102.8 (2) C22—O5—C21—C20 −80.2 (3)
C8—C9—C10—O7 135.2 (2) O4—C20—C21—O5 −17.2 (4)
O3—C9—C10—C11 −100.8 (2) C9—C20—C21—O5 162.6 (2)
C20—C9—C10—C11 141.3 (2) C21—O5—C22—O6 4.0 (5)
C8—C9—C10—C11 19.3 (2) C21—O5—C22—C23 −176.3 (3)
O7—C10—C11—C12 −107.6 (2) C10—O7—C24—O8 0.6 (4)
C9—C10—C11—C12 11.3 (3) C10—O7—C24—C25 −178.8 (2)
C10—C11—C12—C13 −167.4 (2)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
O2—H1O2···O8i 0.84 1.92 2.750 (3) 169
O3—H1O3···O1ii 0.84 1.95 2.747 (3) 157
