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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3257.
Published online 2009 November 28. doi:  10.1107/S1600536809050612
PMCID: PMC2971900

4-Des­oxy-4β-(4-methoxy­carbonyl-1,2,3-triazol-1-yl)podophyllotoxin dichloro­methane solvate

Abstract

In the title compound {systematic name: methyl 1-[12-oxo-10-(3,4,5-trimethoxy­phen­yl)-4,6,13-trioxa­tetra­cyclo­[7.7.0.03,7.011,15]hexa­deca-1,3(7),8-trien-16-yl]-1H-1,2,3-triazole-4-carboxyl­ate dichloro­methane solvate}, C26H25N3O9·CH2Cl2, the tetra­hydro­furan ring and the six-membered ring fused to it both display envelope conformations.

Related literature

For similar structures of 4β-N-substituted-4-desoxypodo­phyllotoxin and derivatives, see: Bilal et al. (2008 [triangle]); Yu & Chen (2008 [triangle]); Van Maanen et al. (1988 [triangle]). For a review of the structures of azides and triazides, see: Bräse et al. (2005 [triangle]). For additional background to 1,3-dipolar azide–alkyne cycloaddition reactions, see: Hainsworth et al. (1985 [triangle]); Huisgen (1963 [triangle]); Jacobsen et al. (1988 [triangle]); Lee (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o3257-scheme1.jpg

Experimental

Crystal data

  • C26H25N3O9·CH2Cl2
  • M r = 608.42
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3257-efi1.jpg
  • a = 10.377 (2) Å
  • b = 12.639 (3) Å
  • c = 20.463 (4) Å
  • V = 2683.9 (10) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.30 mm−1
  • T = 113 K
  • 0.28 × 0.24 × 0.12 mm

Data collection

  • Rigaku Saturn CCD area-detector diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 [triangle]) T min = 0.920, T max = 0.965
  • 22515 measured reflections
  • 6397 independent reflections
  • 5768 reflections with I > 2σ(I)
  • R int = 0.036

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.079
  • S = 1.01
  • 6397 reflections
  • 374 parameters
  • H-atom parameters constrained
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.34 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2800 Friedel pairs
  • Flack parameter: 0.04 (4)

Data collection: CrystalClear (Rigaku/MSC, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809050612/vm2011sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050612/vm2011Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by the National Natural Science Foundation of China (No. 30873363), the Great Program of the Science Foundation of Tianjin (09ZCKFNC01200) and the Program of the Science Foundation of Tianjin (08JCYBJC070000).

supplementary crystallographic information

Comment

Podophyllotoxin derivatives such as Etoposide and Teniposide are in clinical use as antineoplastic agents. NK611, as well as NPF, GL-311 and TOP53 are presently under clinical trials. These podophyllotoxin ligands block the catalytic activity of DNA-topoisomerase II by stabilizing a cleavable enzyme DNA complex in which the DNA is cleaved and covalently linked to the enzyme (Hainsworth,1985). Its high toxicity has limited its application as a drug in cancer chemotherapy. Hence, extensive structure modifications have been performed since the 1950's. Meanwhile, click chemistry with copper-catalyzed Huisgen 1,3-dipolar azide-alkyne cycloaddition (CuAAC) producing 1,2,3-triazoles has exhibited increasing importance in organic chemistry due to the chemoselective nature and mild reaction conditions (Bräse, 2005). Moreover, as a functional group the 1,2,3-triazole ring has found widespread occurrence in a variety of fields. These advantages have stimulated us to couple the podophyllotoxin parent nucleus with 1,2,3-triazole to give potential anticancer candidates. Herein we report the crystal structure of the title compound (Fig.1), which can be used as a candidate for anti-tumor molecules. The asymmetric unit consists of the organic molecule and one dichloromethane molecule, C26H25N3O9.CH2Cl2. The configuration of this derivative is the same as found for podophyllotoxin, which is compatible with the mild reaction conditions. The compound contains three planar moieties: plane A consisting of atoms C10 to C22, plane B consisting of atoms C1 to C6, and the triazole ring as plane C. The dihedral angles between the planes A/B, B/C and A/C are 83.82 (6)°, 32.06 (8)° and 86.54 (7)°, respectively.

Experimental

The title compound was synthesized from natural product podophyllotoxin by copper-catalyzed Huisgen 1, 3-dipolar azide-alkyne cycloaddition. Crystals of the title compound suitable for crystal structure analysis were obtained from a dichloromethane solution by slowly evaporating the solvent.

Refinement

All H atoms were located in difference Fourier maps and refined independently with isotropic displacement parameters.

Figures

Fig. 1.
The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.

Crystal data

C26H25N3O9·CH2Cl2Dx = 1.506 Mg m3
Mr = 608.42Melting point = 212–213 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 9219 reflections
a = 10.377 (2) Åθ = 1.9–27.9°
b = 12.639 (3) ŵ = 0.30 mm1
c = 20.463 (4) ÅT = 113 K
V = 2683.9 (10) Å3Block, colorless
Z = 40.28 × 0.24 × 0.12 mm
F(000) = 1264

Data collection

Rigaku Saturn CCD area-detector diffractometer6397 independent reflections
Radiation source: rotating anode5768 reflections with I > 2σ(I)
confocalRint = 0.036
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 1.9°
ω and [var phi] scansh = −13→13
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)k = −12→16
Tmin = 0.920, Tmax = 0.965l = −26→26
22515 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.079w = 1/[σ2(Fo2) + (0.0476P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
6397 reflectionsΔρmax = 0.18 e Å3
374 parametersΔρmin = −0.34 e Å3
0 restraintsAbsolute structure: Flack (1983), 2800 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.04 (4)

Special details

Experimental. Both Cu+ and Cu2+ can be used as catalyst while combined with respective additives.
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)

xyzUiso*/Ueq
O10.81730 (11)0.46481 (8)−0.07929 (6)0.0222 (2)
O21.02230 (11)0.38471 (8)−0.13992 (5)0.0200 (2)
O31.07335 (11)0.17818 (9)−0.13872 (6)0.0242 (3)
O41.03010 (12)0.07454 (9)0.18541 (6)0.0279 (3)
O51.04059 (12)−0.10864 (9)0.17747 (6)0.0263 (3)
O60.49041 (12)−0.00212 (9)−0.11823 (6)0.0273 (3)
O70.50203 (13)0.17197 (9)−0.09864 (6)0.0313 (3)
O80.35597 (12)−0.14406 (9)0.20717 (6)0.0254 (3)
O90.30253 (11)−0.31101 (8)0.17946 (6)0.0242 (3)
N10.60318 (12)−0.17930 (9)0.04644 (6)0.0167 (3)
N20.56517 (13)−0.28046 (10)0.03289 (7)0.0234 (3)
N30.47699 (14)−0.30643 (10)0.07549 (6)0.0226 (3)
C10.78479 (14)0.18283 (11)−0.03338 (7)0.0162 (3)
C20.75602 (15)0.29059 (11)−0.03655 (7)0.0176 (3)
H20.68350.3180−0.01380.021*
C30.83415 (15)0.35759 (11)−0.07318 (8)0.0172 (3)
C40.93996 (15)0.31698 (12)−0.10722 (7)0.0165 (3)
C50.96690 (15)0.20875 (12)−0.10457 (7)0.0175 (3)
C60.88965 (15)0.14181 (12)−0.06738 (8)0.0178 (3)
H60.90850.0683−0.06520.021*
C70.72731 (16)0.51437 (13)−0.03645 (8)0.0261 (4)
H7A0.75490.50420.00890.039*
H7B0.64190.4828−0.04270.039*
H7C0.72320.5902−0.04620.039*
C80.98547 (17)0.40051 (14)−0.20675 (8)0.0245 (4)
H8A0.90160.4361−0.20840.037*
H8B0.97940.3319−0.22880.037*
H8C1.05020.4443−0.22870.037*
C91.09771 (18)0.06681 (13)−0.14314 (9)0.0279 (4)
H9A1.02240.0314−0.16200.042*
H9B1.11450.0384−0.09940.042*
H9C1.17290.0545−0.17110.042*
C100.70229 (15)0.11348 (11)0.01110 (7)0.0165 (3)
H100.65400.16230.04070.020*
C110.78712 (15)0.04464 (11)0.05453 (7)0.0161 (3)
C120.86601 (15)0.09890 (12)0.09961 (8)0.0192 (3)
H120.86370.17380.10290.023*
C130.94594 (15)0.03996 (12)0.13838 (8)0.0188 (3)
C141.09057 (17)−0.01795 (14)0.21149 (9)0.0278 (4)
H14A1.0721−0.02390.25880.033*
H14B1.1851−0.01350.20560.033*
C150.95192 (15)−0.06919 (12)0.13392 (8)0.0188 (3)
C160.87764 (15)−0.12393 (12)0.09064 (8)0.0181 (3)
H160.8828−0.19880.08750.022*
C170.79280 (14)−0.06537 (11)0.05070 (7)0.0156 (3)
C180.70594 (15)−0.13007 (11)0.00655 (7)0.0162 (3)
H180.7587−0.1880−0.01330.019*
C190.65391 (15)−0.06140 (11)−0.04854 (8)0.0174 (3)
H190.7265−0.0457−0.07920.021*
C200.53937 (17)−0.09906 (12)−0.08870 (8)0.0224 (3)
H20A0.5667−0.1503−0.12260.027*
H20B0.4734−0.1325−0.06050.027*
C210.52869 (16)0.08367 (13)−0.08212 (8)0.0224 (3)
C220.60149 (15)0.04366 (11)−0.02292 (7)0.0173 (3)
H220.53530.02580.01080.021*
C230.53786 (16)−0.14106 (12)0.09778 (7)0.0172 (3)
H230.5456−0.07310.11720.021*
C240.45700 (15)−0.22220 (12)0.11611 (8)0.0169 (3)
C250.36761 (15)−0.22017 (12)0.17193 (8)0.0192 (3)
C260.21945 (17)−0.31309 (14)0.23663 (8)0.0287 (4)
H26A0.1500−0.26130.23120.043*
H26B0.2700−0.29540.27560.043*
H26C0.1824−0.38390.24160.043*
Cl10.26269 (6)0.39288 (4)0.23482 (3)0.05616 (18)
Cl20.21387 (5)0.18814 (4)0.29584 (2)0.03992 (13)
C270.1834 (2)0.27027 (14)0.22719 (10)0.0343 (4)
H27A0.21340.23420.18700.041*
H27B0.08950.28230.22310.041*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0274 (6)0.0121 (5)0.0272 (6)0.0025 (4)0.0052 (5)0.0009 (4)
O20.0216 (6)0.0202 (6)0.0181 (5)−0.0065 (4)0.0010 (5)0.0023 (4)
O30.0228 (6)0.0206 (6)0.0293 (6)0.0030 (5)0.0106 (5)−0.0002 (5)
O40.0315 (7)0.0217 (6)0.0305 (7)−0.0010 (5)−0.0133 (6)−0.0014 (5)
O50.0284 (6)0.0208 (6)0.0297 (7)0.0024 (5)−0.0120 (5)0.0002 (5)
O60.0307 (7)0.0246 (6)0.0267 (6)−0.0017 (5)−0.0094 (5)0.0035 (5)
O70.0314 (7)0.0243 (6)0.0381 (7)0.0046 (5)−0.0067 (6)0.0088 (6)
O80.0291 (7)0.0228 (6)0.0241 (6)−0.0017 (5)0.0064 (5)−0.0022 (5)
O90.0249 (6)0.0238 (6)0.0239 (6)−0.0066 (5)0.0036 (5)0.0035 (5)
N10.0195 (6)0.0119 (6)0.0186 (6)−0.0005 (5)0.0004 (5)−0.0004 (5)
N20.0275 (8)0.0157 (7)0.0269 (8)−0.0054 (5)0.0019 (6)−0.0033 (6)
N30.0256 (8)0.0194 (7)0.0227 (7)−0.0059 (6)0.0025 (6)−0.0006 (6)
C10.0182 (7)0.0155 (7)0.0149 (7)−0.0014 (6)−0.0009 (6)−0.0006 (6)
C20.0177 (8)0.0168 (8)0.0184 (8)0.0011 (6)0.0010 (6)−0.0016 (6)
C30.0212 (8)0.0121 (7)0.0181 (8)0.0000 (6)−0.0037 (6)0.0006 (6)
C40.0175 (8)0.0178 (7)0.0141 (7)−0.0045 (6)−0.0001 (6)0.0016 (6)
C50.0162 (8)0.0215 (8)0.0148 (7)0.0009 (6)0.0015 (6)−0.0031 (6)
C60.0195 (8)0.0156 (7)0.0184 (8)0.0008 (6)−0.0006 (6)0.0002 (6)
C70.0264 (9)0.0177 (8)0.0342 (10)0.0026 (6)0.0033 (8)−0.0017 (7)
C80.0290 (9)0.0268 (9)0.0178 (8)0.0008 (7)0.0028 (7)0.0030 (7)
C90.0315 (9)0.0257 (9)0.0267 (9)0.0104 (7)0.0078 (8)0.0010 (7)
C100.0185 (8)0.0138 (7)0.0171 (8)0.0009 (6)0.0027 (6)0.0005 (6)
C110.0169 (8)0.0155 (7)0.0158 (7)−0.0005 (6)0.0042 (6)0.0007 (5)
C120.0212 (8)0.0157 (8)0.0206 (8)−0.0015 (6)0.0031 (6)0.0012 (6)
C130.0185 (8)0.0188 (8)0.0192 (8)−0.0038 (6)0.0015 (6)−0.0020 (6)
C140.0287 (9)0.0268 (9)0.0278 (9)0.0036 (7)−0.0089 (7)−0.0029 (7)
C150.0176 (8)0.0191 (8)0.0196 (8)0.0028 (6)0.0007 (6)0.0017 (6)
C160.0192 (8)0.0152 (8)0.0199 (8)0.0012 (6)0.0024 (6)0.0004 (6)
C170.0155 (7)0.0151 (7)0.0162 (7)0.0005 (5)0.0035 (6)0.0003 (5)
C180.0171 (8)0.0153 (7)0.0162 (7)−0.0009 (6)0.0036 (6)−0.0010 (6)
C190.0195 (8)0.0160 (8)0.0169 (8)−0.0006 (6)0.0023 (6)−0.0010 (6)
C200.0262 (9)0.0195 (8)0.0214 (8)−0.0008 (7)−0.0025 (7)0.0023 (6)
C210.0186 (8)0.0255 (9)0.0231 (8)−0.0017 (6)0.0006 (7)0.0041 (7)
C220.0172 (7)0.0152 (8)0.0194 (8)0.0004 (6)0.0037 (6)0.0026 (6)
C230.0204 (8)0.0164 (7)0.0148 (8)0.0011 (6)0.0003 (6)−0.0007 (6)
C240.0184 (8)0.0156 (7)0.0166 (8)−0.0006 (6)−0.0026 (6)0.0014 (6)
C250.0169 (8)0.0215 (8)0.0192 (8)−0.0009 (6)−0.0013 (7)0.0053 (6)
C260.0261 (9)0.0301 (9)0.0300 (9)−0.0017 (8)0.0072 (8)0.0105 (8)
Cl10.0722 (4)0.0437 (3)0.0526 (3)−0.0320 (3)0.0287 (3)−0.0187 (3)
Cl20.0490 (3)0.0366 (3)0.0342 (3)0.0004 (2)0.0064 (2)−0.0110 (2)
C270.0350 (11)0.0262 (9)0.0417 (11)−0.0044 (8)0.0050 (9)−0.0084 (8)

Geometric parameters (Å, °)

O1—C31.3722 (18)C9—H9A0.9800
O1—C71.4258 (19)C9—H9B0.9800
O2—C41.3823 (17)C9—H9C0.9800
O2—C81.4339 (19)C10—C111.524 (2)
O3—C51.3631 (19)C10—C221.535 (2)
O3—C91.433 (2)C10—H101.0000
O4—C131.3710 (19)C11—C171.394 (2)
O4—C141.430 (2)C11—C121.411 (2)
O5—C151.3747 (19)C12—C131.368 (2)
O5—C141.438 (2)C12—H120.9500
O6—C211.371 (2)C13—C151.384 (2)
O6—C201.4575 (19)C14—H14A0.9900
O7—C211.1985 (19)C14—H14B0.9900
O8—C251.2084 (19)C15—C161.363 (2)
O9—C251.3409 (19)C16—C171.411 (2)
O9—C261.454 (2)C16—H160.9500
N1—C231.340 (2)C17—C181.516 (2)
N1—N21.3664 (18)C18—C191.522 (2)
N1—C181.4800 (19)C18—H181.0000
N2—N31.3057 (19)C19—C201.521 (2)
N3—C241.367 (2)C19—C221.528 (2)
C1—C61.392 (2)C19—H191.0000
C1—C21.396 (2)C20—H20A0.9900
C1—C101.526 (2)C20—H20B0.9900
C2—C31.392 (2)C21—C221.515 (2)
C2—H20.9500C22—H221.0000
C3—C41.398 (2)C23—C241.377 (2)
C4—C51.397 (2)C23—H230.9500
C5—C61.392 (2)C24—C251.472 (2)
C6—H60.9500C26—H26A0.9800
C7—H7A0.9800C26—H26B0.9800
C7—H7B0.9800C26—H26C0.9800
C7—H7C0.9800Cl1—C271.7613 (19)
C8—H8A0.9800Cl2—C271.775 (2)
C8—H8B0.9800C27—H27A0.9900
C8—H8C0.9800C27—H27B0.9900
C3—O1—C7117.47 (12)O4—C14—O5108.23 (13)
C4—O2—C8112.53 (12)O4—C14—H14A110.1
C5—O3—C9116.98 (12)O5—C14—H14A110.1
C13—O4—C14106.31 (12)O4—C14—H14B110.1
C15—O5—C14105.43 (12)O5—C14—H14B110.1
C21—O6—C20109.90 (12)H14A—C14—H14B108.4
C25—O9—C26114.00 (12)C16—C15—O5128.01 (14)
C23—N1—N2110.51 (12)C16—C15—C13121.57 (15)
C23—N1—C18130.16 (12)O5—C15—C13110.42 (14)
N2—N1—C18119.31 (12)C15—C16—C17117.59 (14)
N3—N2—N1107.58 (12)C15—C16—H16121.2
N2—N3—C24108.46 (12)C17—C16—H16121.2
C6—C1—C2120.50 (14)C11—C17—C16121.13 (14)
C6—C1—C10121.51 (13)C11—C17—C18123.14 (14)
C2—C1—C10117.91 (13)C16—C17—C18115.68 (13)
C3—C2—C1119.62 (14)N1—C18—C17109.06 (12)
C3—C2—H2120.2N1—C18—C19113.12 (13)
C1—C2—H2120.2C17—C18—C19110.17 (12)
O1—C3—C2125.16 (14)N1—C18—H18108.1
O1—C3—C4114.67 (14)C17—C18—H18108.1
C2—C3—C4120.17 (14)C19—C18—H18108.1
O2—C4—C5120.10 (14)C20—C19—C18119.93 (12)
O2—C4—C3119.95 (13)C20—C19—C22100.32 (12)
C5—C4—C3119.81 (13)C18—C19—C22111.58 (13)
O3—C5—C6125.09 (14)C20—C19—H19108.1
O3—C5—C4114.81 (13)C18—C19—H19108.1
C6—C5—C4120.07 (14)C22—C19—H19108.1
C1—C6—C5119.82 (14)O6—C20—C19103.49 (12)
C1—C6—H6120.1O6—C20—H20A111.1
C5—C6—H6120.1C19—C20—H20A111.1
O1—C7—H7A109.5O6—C20—H20B111.1
O1—C7—H7B109.5C19—C20—H20B111.1
H7A—C7—H7B109.5H20A—C20—H20B109.0
O1—C7—H7C109.5O7—C21—O6121.17 (15)
H7A—C7—H7C109.5O7—C21—C22130.67 (15)
H7B—C7—H7C109.5O6—C21—C22108.15 (13)
O2—C8—H8A109.5C21—C22—C19101.14 (13)
O2—C8—H8B109.5C21—C22—C10120.70 (12)
H8A—C8—H8B109.5C19—C22—C10114.36 (13)
O2—C8—H8C109.5C21—C22—H22106.6
H8A—C8—H8C109.5C19—C22—H22106.6
H8B—C8—H8C109.5C10—C22—H22106.6
O3—C9—H9A109.5N1—C23—C24104.66 (13)
O3—C9—H9B109.5N1—C23—H23127.7
H9A—C9—H9B109.5C24—C23—H23127.7
O3—C9—H9C109.5N3—C24—C23108.78 (14)
H9A—C9—H9C109.5N3—C24—C25125.55 (14)
H9B—C9—H9C109.5C23—C24—C25125.63 (14)
C11—C10—C1110.59 (12)O8—C25—O9124.24 (15)
C11—C10—C22109.26 (12)O8—C25—C24122.69 (14)
C1—C10—C22116.22 (12)O9—C25—C24113.07 (14)
C11—C10—H10106.8O9—C26—H26A109.5
C1—C10—H10106.8O9—C26—H26B109.5
C22—C10—H10106.8H26A—C26—H26B109.5
C17—C11—C12119.80 (14)O9—C26—H26C109.5
C17—C11—C10124.14 (14)H26A—C26—H26C109.5
C12—C11—C10116.03 (12)H26B—C26—H26C109.5
C13—C12—C11117.78 (14)Cl1—C27—Cl2111.18 (11)
C13—C12—H12121.1Cl1—C27—H27A109.4
C11—C12—H12121.1Cl2—C27—H27A109.4
C12—C13—O4128.28 (14)Cl1—C27—H27B109.4
C12—C13—C15122.11 (15)Cl2—C27—H27B109.4
O4—C13—C15109.60 (14)H27A—C27—H27B108.0
C23—N1—N2—N3−0.34 (17)C13—C15—C16—C17−0.7 (2)
C18—N1—N2—N3178.32 (12)C12—C11—C17—C16−0.9 (2)
N1—N2—N3—C240.55 (17)C10—C11—C17—C16177.31 (13)
C6—C1—C2—C3−1.0 (2)C12—C11—C17—C18176.30 (13)
C10—C1—C2—C3175.82 (14)C10—C11—C17—C18−5.5 (2)
C7—O1—C3—C211.4 (2)C15—C16—C17—C111.2 (2)
C7—O1—C3—C4−168.31 (14)C15—C16—C17—C18−176.13 (14)
C1—C2—C3—O1−178.91 (14)C23—N1—C18—C1737.7 (2)
C1—C2—C3—C40.7 (2)N2—N1—C18—C17−140.67 (13)
C8—O2—C4—C592.48 (17)C23—N1—C18—C19−85.29 (18)
C8—O2—C4—C3−91.68 (17)N2—N1—C18—C1996.36 (15)
O1—C3—C4—O24.1 (2)C11—C17—C18—N1−103.10 (16)
C2—C3—C4—O2−175.64 (14)C16—C17—C18—N174.20 (16)
O1—C3—C4—C5179.91 (13)C11—C17—C18—C1921.6 (2)
C2—C3—C4—C50.2 (2)C16—C17—C18—C19−161.08 (13)
C9—O3—C5—C68.2 (2)N1—C18—C19—C20−41.98 (18)
C9—O3—C5—C4−173.77 (14)C17—C18—C19—C20−164.34 (13)
O2—C4—C5—O3−3.2 (2)N1—C18—C19—C2274.75 (15)
C3—C4—C5—O3−179.03 (14)C17—C18—C19—C22−47.60 (17)
O2—C4—C5—C6174.94 (14)C21—O6—C20—C19−22.57 (16)
C3—C4—C5—C6−0.9 (2)C18—C19—C20—O6160.39 (13)
C2—C1—C6—C50.3 (2)C22—C19—C20—O637.97 (14)
C10—C1—C6—C5−176.39 (14)C20—O6—C21—O7177.91 (16)
O3—C5—C6—C1178.54 (14)C20—O6—C21—C22−3.11 (17)
C4—C5—C6—C10.6 (2)O7—C21—C22—C19−153.98 (19)
C6—C1—C10—C1145.76 (19)O6—C21—C22—C1927.17 (16)
C2—C1—C10—C11−131.05 (14)O7—C21—C22—C10−26.7 (3)
C6—C1—C10—C22−79.53 (18)O6—C21—C22—C10154.47 (14)
C2—C1—C10—C22103.66 (16)C20—C19—C22—C21−38.84 (14)
C1—C10—C11—C17−114.25 (16)C18—C19—C22—C21−166.96 (12)
C22—C10—C11—C1714.9 (2)C20—C19—C22—C10−170.17 (13)
C1—C10—C11—C1263.98 (17)C18—C19—C22—C1061.71 (17)
C22—C10—C11—C12−166.88 (13)C11—C10—C22—C21−163.16 (13)
C17—C11—C12—C13−0.1 (2)C1—C10—C22—C21−37.2 (2)
C10—C11—C12—C13−178.42 (14)C11—C10—C22—C19−42.11 (17)
C11—C12—C13—O4−179.74 (15)C1—C10—C22—C1983.85 (16)
C11—C12—C13—C150.7 (2)N2—N1—C23—C24−0.01 (17)
C14—O4—C13—C12−179.90 (17)C18—N1—C23—C24−178.48 (15)
C14—O4—C13—C15−0.29 (18)N2—N3—C24—C23−0.56 (18)
C13—O4—C14—O50.88 (18)N2—N3—C24—C25−178.25 (14)
C15—O5—C14—O4−1.12 (18)N1—C23—C24—N30.34 (17)
C14—O5—C15—C16−179.58 (17)N1—C23—C24—C25178.03 (14)
C14—O5—C15—C130.96 (18)C26—O9—C25—O8−3.0 (2)
C12—C13—C15—C16−0.3 (3)C26—O9—C25—C24176.46 (13)
O4—C13—C15—C16−179.94 (14)N3—C24—C25—O8178.28 (16)
C12—C13—C15—O5179.20 (14)C23—C24—C25—O81.0 (3)
O4—C13—C15—O5−0.43 (19)N3—C24—C25—O9−1.2 (2)
O5—C15—C16—C17179.92 (15)C23—C24—C25—O9−178.50 (15)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: VM2011).

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