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Acta Cryst. (2011). E67, o360    [ doi:10.1107/S1600536811000316 ]

Triamcinolone acetonide acetate

X. Lu, G.-P. Tang, J.-M. Gu and X.-R. Hu

Abstract top

In the crystal structure of the title compound [systematic name: 2-(4b-fluoro-5-hydroxy-4a,6a,8,8-tetramethyl-2-oxo-2,4a,4b,5,6,6a,9a,10,10a,10b,11,12-dodecahydro-7,9-dioxapentaleno[2,1-a]phenanthren-6b-yl)-2-oxoethyl acetate], C26H33FO7, the molecules are connected by intermolecular O-H...O hydrogen bonds into an infinite supramolecular chain along the b axis. The molecular framework consists of five condensed rings, including three six-membered rings and two five-membered rings. The cyclohexa-2,5-dienone ring is nearly planar [maximum deviation = 0.013 (3) Å], while the cyclohexane rings adopt chair conformations. The two five-membered rings, viz. cyclopentane and 1,3-dioxolane, display envelope conformations.

Comment top

The glucocorticoid triamcinolone acetonide is clinically used for the treatment of suppression of inflammation in chronic inflammatory diseases such as asthma, rheumatiod arthritis, inflammatory bowel disease and autoimmune diseases (Barnes, 1998; Buttgereit, 2000; Uckermann et al., 2005). Triamcinolone acetonide acetate is another derivatives of triamcinolone, which has been used in therapy for several decades. Despite its great importance, no crystal structures of the title compound has been reported. But crystal structure of it's analogue compounds, triamcinolone diacetate chloroform solvate and triamcinole acetonide methanol solvate have been reported (Suitchlmezian et al., 2006 & Jess et al., 2006). In the title compound, the bond lengths and angles are in agreement with those reported for other triamcinolone derivatives (Suitchlmezian et al., 2006; Jess et al., 2006). and are within the expected ranges. The molecular framework consists of five condensed rings, including three six-membered rings and two five-membered rings. Atom O1 is coplanar with cyclohexa-1,4-diene ring (C8—C9—C10—C11—C12—C13), which is planar. Two central six-membered rings (C5—C6—C7—C8—C13—C14) and (C4—C5—C14—C15—C16—C17) are in chair conformation. Two five-membered rings display twisted envelope conformations. The respective r.m.s. deviations for four atoms C1/C2/C3/C17 and C1/C2/O6/O7 are 0.0359 Å, 0.0225Å respectively. The fifth atoms C4, C22 deviate from the above planes by 0.688 (4) Å, 0.458 (4)Å respectively. Hydroxy group and one of the carboxyl O atom are involved in the hydrogen- bonded network. Atom O2 from hydroxy group in the molecule at (x,y,z) act as hydrogen bond donor, to O1 atom of carboxyl group in the molecule (2 - x,-1/2 + y,2 - z). Crystal packing is influenced by this intermolecular hydrogen bond interaction that links the molecules into a chain propagating along b axis.

Related literature top

For applications of triamcinolone acetonide in medicine, see: Barnes (1998); Buttgereit (2000); Uckermann et al. (2005). For the crystal structures of related triamcinolone acetonide acetates, see: Suitchlmezian et al. (2006); Jess & Näther (2006).

Experimental top

The crude product of the title compound was supplied by Zhejiang Xianju Pharmaceutical Co., LTD. It was recrystallized from methanol solution, giving single crystals suitable for X-ray diffraction.

Refinement top

H atoms were placed in calculated positions with C—H = 0.93–0.98 and O—H = 0.82 Å, and included in the refinement in riding model with Uiso(H) = 1.2Ueq or 1.5Ueq(carrier atom).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 2006); cell refinement: PROCESS-AUTO (Rigaku, 2006); data reduction: CrystalStructure (Rigaku, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound (I) showing atom-labelling scheme and displacement ellipsoids at 50% probability level. H atoms are shown as small circles of arbitrary radii.
[Figure 2] Fig. 2. A chain of molecules linked through hydrogen-bonded interactions propagating along b axis. Hydrogen bonds are shown as dashed lines. [Symmetric code: (i)(2 - x,-1/2 + y,2 - z); (ii)(2 - x,1/2 + y,2 - z)]
2-(4b-Fluoro-5-hydroxy-4a,6a,8,8-tetramethyl-2-oxo- 2,4a,4b,5,6,6a,9a,10,10a,10b,11,12-dodecahydro-7,9-dioxa- pentaleno[2,1-a]phenanthren-6b-yl)-2-oxoethyl acetate top
Crystal data top
C26H33FO7F(000) = 508
Mr = 476.52Dx = 1.301 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 8589 reflections
a = 7.5460 (7) Åθ = 3.2–27.4°
b = 14.8102 (4) ŵ = 0.10 mm−1
c = 11.5773 (3) ÅT = 296 K
β = 109.905 (1)°Chunk, colorless
V = 1216.56 (12) Å30.38 × 0.33 × 0.26 mm
Z = 2
Data collection top
Rigaku R-AXIS RAPID/ZJUG
diffractometer		1866 reflections with I > 2σ(I)
Radiation source: rolling anodeRint = 0.027
graphiteθmax = 25.0°, θmin = 3.2°
Detector resolution: 10.00 pixels mm-1h = −8→8
ω scansk = −17→17
9347 measured reflectionsl = −13→13
2216 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0428P)2 + 0.6583P]
where P = (Fo2 + 2Fc2)/3
2216 reflections(Δ/σ)max < 0.001
308 parametersΔρmax = 0.18 e Å−3
1 restraintΔρmin = −0.21 e Å−3
Crystal data top
C26H33FO7V = 1216.56 (12) Å3
Mr = 476.52Z = 2
Monoclinic, P21Mo Kα radiation
a = 7.5460 (7) ŵ = 0.10 mm−1
b = 14.8102 (4) ÅT = 296 K
c = 11.5773 (3) Å0.38 × 0.33 × 0.26 mm
β = 109.905 (1)°
Data collection top
Rigaku R-AXIS RAPID/ZJUG
diffractometer		1866 reflections with I > 2σ(I)
9347 measured reflectionsRint = 0.027
2216 independent reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.100Δρmax = 0.18 e Å−3
S = 1.00Δρmin = −0.21 e Å−3
2216 reflectionsAbsolute structure: ?
308 parametersFlack parameter: ?
1 restraintRogers parameter: ?
Special details top

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) top
xyzUiso*/Ueq
F10.6313 (3)0.54106 (13)0.76554 (17)0.0388 (5)
O60.5255 (4)0.35878 (18)0.4342 (2)0.0425 (6)
O70.2113 (4)0.3480 (2)0.3882 (2)0.0580 (8)
O20.9010 (4)0.3514 (2)0.9117 (2)0.0498 (7)
H2010.99780.33030.90560.075*
O10.7606 (4)0.76945 (19)1.0779 (3)0.0558 (8)
O40.8680 (4)0.1362 (2)0.4470 (3)0.0638 (9)
O30.5322 (4)0.1277 (2)0.4898 (3)0.0582 (8)
O50.9888 (5)0.1500 (2)0.6510 (3)0.0728 (9)
C80.5342 (5)0.5590 (3)0.9699 (3)0.0407 (9)
C140.6558 (5)0.4623 (2)0.8393 (3)0.0322 (7)
C160.7704 (5)0.3720 (3)0.6873 (3)0.0376 (8)
H16A0.75560.41980.62750.045*
H16B0.87310.33360.68480.045*
C50.4670 (5)0.4121 (2)0.7923 (3)0.0336 (8)
H50.47380.36020.84610.040*
C70.3424 (5)0.5160 (3)0.9231 (4)0.0480 (10)
H7A0.24680.56130.91710.058*
H7B0.33340.47000.98050.058*
C130.6966 (5)0.4988 (2)0.9729 (3)0.0361 (8)
C170.5885 (5)0.3160 (2)0.6510 (3)0.0333 (8)
C90.5589 (5)0.6453 (3)1.0052 (3)0.0433 (9)
H90.45390.67891.00330.052*
C60.3070 (5)0.4733 (3)0.7971 (4)0.0425 (9)
H6A0.19150.43840.77480.051*
H6B0.28910.52100.73670.051*
C40.4318 (4)0.3771 (3)0.6626 (3)0.0339 (8)
H40.42590.43000.61040.041*
C100.7421 (5)0.6892 (3)1.0465 (3)0.0424 (9)
C110.9034 (5)0.6337 (3)1.0487 (4)0.0479 (10)
H111.02340.65901.07480.058*
C30.2545 (5)0.3219 (3)0.6011 (4)0.0450 (9)
H3A0.14270.35950.57880.054*
H3B0.24170.27350.65420.054*
C150.8226 (5)0.4144 (3)0.8163 (3)0.0368 (8)
H150.91910.46030.82290.044*
C120.8813 (5)0.5480 (3)1.0142 (3)0.0432 (9)
H120.98800.51601.01560.052*
C260.6145 (5)0.2300 (3)0.7297 (3)0.0430 (9)
H26A0.71400.19400.71940.065*
H26B0.49950.19590.70420.065*
H26C0.64640.24640.81460.065*
C190.7634 (7)0.2173 (3)0.4445 (4)0.0599 (11)
H19A0.72200.24200.36200.072*
H19B0.84530.26140.49890.072*
C10.5043 (6)0.2880 (3)0.5130 (3)0.0386 (8)
C20.2878 (5)0.2844 (3)0.4866 (3)0.0447 (9)
H20.23590.22350.46510.054*
C220.3498 (6)0.3674 (3)0.3347 (3)0.0502 (10)
C180.5929 (6)0.2019 (3)0.4831 (3)0.0438 (9)
C250.7128 (7)0.4231 (3)1.0695 (4)0.0530 (10)
H25A0.59680.38981.04710.080*
H25B0.73760.44991.14900.080*
H25C0.81400.38301.07200.080*
C240.3353 (8)0.3027 (4)0.2306 (4)0.0689 (14)
H24A0.43070.31680.19590.103*
H24B0.21320.30810.16850.103*
H24C0.35270.24190.26160.103*
C200.9797 (6)0.1098 (3)0.5594 (4)0.0568 (11)
C230.3293 (8)0.4648 (4)0.2940 (4)0.0709 (14)
H23A0.42230.47890.25720.106*
H23B0.34690.50320.36390.106*
H23C0.20570.47430.23520.106*
C211.0917 (8)0.0281 (4)0.5528 (6)0.0910 (18)
H21A1.05760.00870.46890.137*
H21B1.0658−0.01940.60120.137*
H21C1.22350.04250.58400.137*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0395 (11)0.0373 (12)0.0392 (11)−0.0020 (9)0.0130 (9)0.0066 (9)
O60.0465 (14)0.0450 (16)0.0341 (12)−0.0009 (12)0.0114 (11)0.0025 (12)
O70.0448 (15)0.077 (2)0.0448 (14)0.0049 (15)0.0062 (12)0.0030 (15)
O20.0450 (15)0.0604 (19)0.0387 (13)0.0179 (14)0.0076 (12)0.0010 (13)
O10.0597 (18)0.0436 (18)0.0664 (19)−0.0124 (14)0.0245 (15)−0.0184 (15)
O40.0615 (18)0.068 (2)0.0601 (18)0.0153 (16)0.0186 (15)−0.0178 (16)
O30.069 (2)0.0429 (18)0.0593 (17)−0.0048 (15)0.0181 (15)−0.0110 (14)
O50.082 (2)0.075 (2)0.0631 (19)−0.0134 (19)0.0274 (17)−0.0146 (19)
C80.039 (2)0.046 (2)0.043 (2)−0.0073 (17)0.0224 (16)−0.0088 (18)
C140.0344 (18)0.0307 (18)0.0322 (16)0.0007 (15)0.0123 (14)0.0025 (15)
C160.0355 (18)0.045 (2)0.0375 (18)−0.0023 (17)0.0195 (15)−0.0066 (17)
C50.0340 (17)0.0343 (19)0.0372 (17)−0.0021 (15)0.0183 (15)−0.0010 (15)
C70.039 (2)0.054 (3)0.062 (2)−0.0047 (19)0.032 (2)−0.013 (2)
C130.0371 (19)0.038 (2)0.0347 (18)−0.0003 (16)0.0142 (16)−0.0025 (15)
C170.0349 (18)0.0345 (19)0.0324 (16)−0.0015 (15)0.0140 (15)−0.0026 (15)
C90.0369 (19)0.047 (2)0.048 (2)−0.0009 (17)0.0170 (17)−0.0122 (18)
C60.0271 (17)0.050 (2)0.053 (2)−0.0051 (16)0.0169 (16)−0.0100 (19)
C40.0316 (17)0.0364 (19)0.0345 (17)−0.0037 (15)0.0122 (15)−0.0007 (15)
C100.042 (2)0.048 (3)0.0382 (19)−0.0085 (18)0.0159 (17)−0.0087 (18)
C110.0365 (19)0.057 (3)0.049 (2)−0.0062 (19)0.0123 (17)−0.013 (2)
C30.037 (2)0.048 (2)0.052 (2)−0.0076 (17)0.0171 (17)−0.0077 (18)
C150.0343 (18)0.038 (2)0.0406 (19)0.0000 (16)0.0163 (15)−0.0046 (16)
C120.0379 (19)0.053 (3)0.0385 (19)−0.0013 (18)0.0130 (16)−0.0100 (19)
C260.046 (2)0.042 (2)0.0373 (19)−0.0022 (18)0.0098 (17)−0.0018 (18)
C190.068 (3)0.057 (3)0.064 (3)0.011 (2)0.035 (2)−0.004 (2)
C10.0438 (19)0.038 (2)0.0345 (18)−0.0009 (17)0.0139 (16)−0.0025 (16)
C20.044 (2)0.045 (2)0.041 (2)−0.0104 (18)0.0103 (17)−0.0103 (17)
C220.048 (2)0.062 (3)0.0328 (18)0.006 (2)0.0041 (17)0.0013 (19)
C180.047 (2)0.041 (2)0.0375 (19)0.0025 (18)0.0079 (17)−0.0035 (17)
C250.066 (3)0.058 (3)0.038 (2)0.006 (2)0.0218 (19)0.0061 (19)
C240.079 (3)0.075 (3)0.045 (2)−0.001 (3)0.012 (2)−0.011 (2)
C200.047 (2)0.054 (3)0.069 (3)−0.008 (2)0.018 (2)−0.009 (2)
C230.084 (4)0.060 (3)0.055 (3)0.011 (3)0.004 (3)0.009 (2)
C210.080 (4)0.069 (4)0.123 (5)0.012 (3)0.033 (4)−0.008 (4)
Geometric parameters (Å, °) top
F1—C141.420 (4)C6—H6B0.9700
O6—C11.434 (4)C4—C31.523 (5)
O6—C221.436 (4)C4—H40.9800
O7—C221.414 (5)C10—C111.462 (6)
O7—C21.439 (5)C11—C121.325 (6)
O2—C151.412 (5)C11—H110.9300
O2—H2010.8200C3—C21.535 (5)
O1—C101.237 (5)C3—H3A0.9700
O4—C201.346 (5)C3—H3B0.9700
O4—C191.431 (5)C15—H150.9800
O3—C181.204 (5)C12—H120.9300
O5—C201.197 (5)C26—H26A0.9600
C8—C91.335 (5)C26—H26B0.9600
C8—C71.503 (5)C26—H26C0.9600
C8—C131.506 (5)C19—C181.516 (6)
C14—C51.533 (5)C19—H19A0.9700
C14—C151.545 (5)C19—H19B0.9700
C14—C131.567 (5)C1—C181.533 (5)
C16—C171.535 (5)C1—C21.557 (6)
C16—C151.542 (5)C2—H20.9800
C16—H16A0.9700C22—C231.509 (7)
C16—H16B0.9700C22—C241.514 (6)
C5—C41.523 (5)C25—H25A0.9600
C5—C61.526 (5)C25—H25B0.9600
C5—H50.9800C25—H25C0.9600
C7—C61.528 (5)C24—H24A0.9600
C7—H7A0.9700C24—H24B0.9600
C7—H7B0.9700C24—H24C0.9600
C13—C121.499 (5)C20—C211.493 (7)
C13—C251.559 (5)C23—H23A0.9600
C17—C41.531 (5)C23—H23B0.9600
C17—C261.539 (5)C23—H23C0.9600
C17—C11.561 (5)C21—H21A0.9600
C9—C101.453 (5)C21—H21B0.9600
C9—H90.9300C21—H21C0.9600
C6—H6A0.9700
C1—O6—C22107.6 (3)O2—C15—C16112.9 (3)
C22—O7—C2108.9 (3)O2—C15—C14108.5 (3)
C15—O2—H201109.5C16—C15—C14113.5 (3)
C20—O4—C19115.0 (3)O2—C15—H15107.2
C9—C8—C7122.2 (4)C16—C15—H15107.2
C9—C8—C13122.1 (3)C14—C15—H15107.2
C7—C8—C13115.7 (3)C11—C12—C13124.7 (4)
F1—C14—C5105.6 (3)C11—C12—H12117.6
F1—C14—C15102.7 (2)C13—C12—H12117.6
C5—C14—C15115.4 (3)C17—C26—H26A109.5
F1—C14—C13104.6 (3)C17—C26—H26B109.5
C5—C14—C13111.4 (3)H26A—C26—H26B109.5
C15—C14—C13115.5 (3)C17—C26—H26C109.5
C17—C16—C15113.3 (3)H26A—C26—H26C109.5
C17—C16—H16A108.9H26B—C26—H26C109.5
C15—C16—H16A108.9O4—C19—C18112.7 (4)
C17—C16—H16B108.9O4—C19—H19A109.1
C15—C16—H16B108.9C18—C19—H19A109.1
H16A—C16—H16B107.7O4—C19—H19B109.1
C4—C5—C6111.3 (3)C18—C19—H19B109.1
C4—C5—C14110.1 (2)H19A—C19—H19B107.8
C6—C5—C14110.5 (3)O6—C1—C18108.2 (3)
C4—C5—H5108.3O6—C1—C2103.8 (3)
C6—C5—H5108.3C18—C1—C2115.9 (3)
C14—C5—H5108.3O6—C1—C17111.3 (3)
C8—C7—C6110.7 (3)C18—C1—C17113.3 (3)
C8—C7—H7A109.5C2—C1—C17104.1 (3)
C6—C7—H7A109.5O7—C2—C3107.9 (3)
C8—C7—H7B109.5O7—C2—C1104.1 (3)
C6—C7—H7B109.5C3—C2—C1106.7 (3)
H7A—C7—H7B108.1O7—C2—H2112.5
C12—C13—C8112.4 (3)C3—C2—H2112.5
C12—C13—C25106.5 (3)C1—C2—H2112.5
C8—C13—C25107.9 (3)O7—C22—O6104.4 (3)
C12—C13—C14109.3 (3)O7—C22—C23108.6 (4)
C8—C13—C14107.2 (3)O6—C22—C23107.7 (4)
C25—C13—C14113.7 (3)O7—C22—C24110.8 (4)
C4—C17—C16107.5 (3)O6—C22—C24112.2 (4)
C4—C17—C26112.6 (3)C23—C22—C24112.7 (4)
C16—C17—C26111.3 (3)O3—C18—C19122.4 (4)
C4—C17—C1100.9 (3)O3—C18—C1122.7 (4)
C16—C17—C1116.0 (3)C19—C18—C1114.9 (4)
C26—C17—C1108.2 (3)C13—C25—H25A109.5
C8—C9—C10123.2 (4)C13—C25—H25B109.5
C8—C9—H9118.4H25A—C25—H25B109.5
C10—C9—H9118.4C13—C25—H25C109.5
C5—C6—C7113.4 (3)H25A—C25—H25C109.5
C5—C6—H6A108.9H25B—C25—H25C109.5
C7—C6—H6A108.9C22—C24—H24A109.5
C5—C6—H6B108.9C22—C24—H24B109.5
C7—C6—H6B108.9H24A—C24—H24B109.5
H6A—C6—H6B107.7C22—C24—H24C109.5
C3—C4—C5118.3 (3)H24A—C24—H24C109.5
C3—C4—C17102.9 (3)H24B—C24—H24C109.5
C5—C4—C17114.0 (3)O5—C20—O4122.7 (4)
C3—C4—H4107.0O5—C20—C21125.8 (5)
C5—C4—H4107.0O4—C20—C21111.4 (4)
C17—C4—H4107.0C22—C23—H23A109.5
O1—C10—C9121.8 (4)C22—C23—H23B109.5
O1—C10—C11121.7 (4)H23A—C23—H23B109.5
C9—C10—C11116.6 (3)C22—C23—H23C109.5
C12—C11—C10121.0 (4)H23A—C23—H23C109.5
C12—C11—H11119.5H23B—C23—H23C109.5
C10—C11—H11119.5C20—C21—H21A109.5
C4—C3—C2102.9 (3)C20—C21—H21B109.5
C4—C3—H3A111.2H21A—C21—H21B109.5
C2—C3—H3A111.2C20—C21—H21C109.5
C4—C3—H3B111.2H21A—C21—H21C109.5
C2—C3—H3B111.2H21B—C21—H21C109.5
H3A—C3—H3B109.1
F1—C14—C5—C467.2 (3)F1—C14—C15—O2161.5 (3)
C15—C14—C5—C4−45.5 (4)C5—C14—C15—O2−84.1 (3)
C13—C14—C5—C4−179.8 (3)C13—C14—C15—O248.3 (4)
F1—C14—C5—C6−56.1 (3)F1—C14—C15—C16−72.2 (4)
C15—C14—C5—C6−168.9 (3)C5—C14—C15—C1642.2 (4)
C13—C14—C5—C656.9 (4)C13—C14—C15—C16174.6 (3)
C9—C8—C7—C6125.6 (4)C10—C11—C12—C13−1.3 (6)
C13—C8—C7—C6−53.7 (5)C8—C13—C12—C112.3 (5)
C9—C8—C13—C12−2.4 (5)C25—C13—C12—C11−115.6 (4)
C7—C8—C13—C12176.9 (3)C14—C13—C12—C11121.2 (4)
C9—C8—C13—C25114.7 (4)C20—O4—C19—C18−77.7 (5)
C7—C8—C13—C25−66.0 (4)C22—O6—C1—C1899.8 (3)
C9—C8—C13—C14−122.5 (4)C22—O6—C1—C2−23.8 (4)
C7—C8—C13—C1456.8 (4)C22—O6—C1—C17−135.2 (3)
F1—C14—C13—C12−65.8 (3)C4—C17—C1—O678.1 (3)
C5—C14—C13—C12−179.5 (3)C16—C17—C1—O6−37.7 (4)
C15—C14—C13—C1246.3 (4)C26—C17—C1—O6−163.5 (3)
F1—C14—C13—C856.3 (3)C4—C17—C1—C18−159.7 (3)
C5—C14—C13—C8−57.4 (4)C16—C17—C1—C1884.5 (4)
C15—C14—C13—C8168.4 (3)C26—C17—C1—C18−41.3 (4)
F1—C14—C13—C25175.4 (3)C4—C17—C1—C2−33.0 (4)
C5—C14—C13—C2561.8 (4)C16—C17—C1—C2−148.8 (3)
C15—C14—C13—C25−72.5 (4)C26—C17—C1—C285.4 (3)
C15—C16—C17—C455.6 (4)C22—O7—C2—C3129.1 (3)
C15—C16—C17—C26−68.1 (4)C22—O7—C2—C116.0 (4)
C15—C16—C17—C1167.7 (3)C4—C3—C2—O7−90.1 (3)
C7—C8—C9—C10−177.7 (4)C4—C3—C2—C121.3 (4)
C13—C8—C9—C101.6 (6)O6—C1—C2—O74.9 (4)
C4—C5—C6—C7−175.6 (3)C18—C1—C2—O7−113.5 (3)
C14—C5—C6—C7−52.9 (4)C17—C1—C2—O7121.5 (3)
C8—C7—C6—C550.0 (5)O6—C1—C2—C3−109.0 (3)
C6—C5—C4—C3−59.5 (4)C18—C1—C2—C3132.6 (3)
C14—C5—C4—C3177.6 (3)C17—C1—C2—C37.5 (4)
C6—C5—C4—C17179.4 (3)C2—O7—C22—O6−31.0 (4)
C14—C5—C4—C1756.5 (4)C2—O7—C22—C23−145.7 (3)
C16—C17—C4—C3169.2 (3)C2—O7—C22—C2490.0 (4)
C26—C17—C4—C3−67.9 (4)C1—O6—C22—O734.3 (4)
C1—C17—C4—C347.2 (3)C1—O6—C22—C23149.6 (3)
C16—C17—C4—C5−61.5 (4)C1—O6—C22—C24−85.8 (4)
C26—C17—C4—C561.5 (4)O4—C19—C18—O3−14.4 (6)
C1—C17—C4—C5176.6 (3)O4—C19—C18—C1165.5 (3)
C8—C9—C10—O1179.5 (4)O6—C1—C18—O3−146.6 (4)
C8—C9—C10—C11−0.4 (6)C2—C1—C18—O3−30.6 (5)
O1—C10—C11—C12−179.7 (4)C17—C1—C18—O389.6 (5)
C9—C10—C11—C120.2 (6)O6—C1—C18—C1933.5 (4)
C5—C4—C3—C2−169.4 (3)C2—C1—C18—C19149.4 (3)
C17—C4—C3—C2−42.8 (4)C17—C1—C18—C19−90.4 (4)
C17—C16—C15—O276.4 (4)C19—O4—C20—O51.2 (6)
C17—C16—C15—C14−47.6 (4)C19—O4—C20—C21−176.7 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H201···O1i0.821.982.793 (4)169
Symmetry codes: (i) −x+2, y−1/2, −z+2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H201···O1i0.821.982.793 (4)169
Symmetry codes: (i) −x+2, y−1/2, −z+2.
Acknowledgements top

The project was supported by the Zhejiang Provincial Natural Science Foundation of China (J200801).

references
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