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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2339.
Published online 2008 November 13. doi:  10.1107/S1600536808035319
PMCID: PMC2959988

4-Des­oxy-4β-[(5-meth­oxy-1H-indol-3-yl)oxalylamino]podophyllotoxin methanol solvate

Abstract

The main mol­ecule of the title solvate, C33H30N2O10·CH3OH, is a new anti­tumor agent, which shows cytotoxicity against MDR cancer cell lines. It has been synthesized by coupling 4β-amino­podophyllotoxin with (5-meth­oxy-1H-indol-3-yl)glyoxyl chloride and structurally characterized. There are two crystallographically independent mol­ecules in the asymmetric unit, which differ in the dihedral angles between the aromatic rings. The dihedral angles between the benzene ring of the benzo[d][1,3]dioxole and the benzene ring of the 5-meth­oxy-1H-indole are 85.08 (3) and 76.88 (3)° and reflect the main conformational difference between the two independent mol­ecules. The asymmetric unit is completed with two methanol solvent mol­ecules, one of which is disordered over two positions, with occupancies close to 0.5.

Related literature

For related preparation and anti­tumor activity, see: Yu et al. (2008 [triangle]); Knaack et al. (2001 [triangle]); Zhou et al. (1991 [triangle]); Zhu et al. (1999 [triangle]); Chen et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2339-scheme1.jpg

Experimental

Crystal data

  • C33H30N2O10·CH4O
  • M r = 646.63
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2339-efi1.jpg
  • a = 12.228 (2) Å
  • b = 9.8360 (16) Å
  • c = 26.667 (5) Å
  • β = 95.58 (3)°
  • V = 3192.2 (9) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 113 (2) K
  • 0.24 × 0.22 × 0.12 mm

Data collection

  • Rigaku Saturn CCD area-detector diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 [triangle]) T min = 0.976, T max = 0.988
  • 22853 measured reflections
  • 7730 independent reflections
  • 6754 reflections with I > 2σ(I)
  • R int = 0.045

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.127
  • S = 1.03
  • 7730 reflections
  • 893 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.73 e Å−3
  • Δρmin = −0.27 e Å−3

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 global, I. DOI: 10.1107/S1600536808035319/bh2197sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035319/bh2197Isup2.hkl

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

Acknowledgments

This work was supported by the Great Program of Science Foundation of Tianjin (06YFJZJCO2700), the Program of Science Foundation of Tianjin (08JCYBJC070000) and the National Natural Science Foundation of China (No. 30873363).

supplementary crystallographic information

Comment

Podophyllotoxins are a particularly instructive class of compounds for consideration in the design and synthesis of potential anticancer agents based upon natural products prototypes. We present here the crystal structure of the title compound (Fig. 1), which can be used as a precursor for antitumor molecules. In the crystal structure, two crystallographically independent molecules are found in the asymmetric unit. The mean planes for the three benzene rings of benzo[d][1,3]dioxole (ring A), 3,4,5-trimethoxyphenyl (ring B) and 5-methoxy-1H-indole (ring C), form dihedral angles A/B = 88.00 (3) and 83.26 (3)°, B/C = 44.66 (3) and 50.01 (4)°, and A/C = 85.08 (3)/76.88 (3)°, respectively. This makes clear that the main difference between conformations in both independent molecules arises from A and C rings (dihedral angles differ by more than 8°), while the podophyllotoxin core structure remains more or less rigid.

Experimental

4β-Aminopodophyllotoxin (1.0 mmol), 5-methoxy-indol-3-yl-glyoxyl chloride (1.0 mmol) and Et3N (2.0 mmol) were dissolved in dry dichloromethane. The mixture was stirred at room temperature for 36 h., and then extracted with dichloromethane after 30 ml water was added. The organic phase was dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel using petroleum ether/ethyl acetate as eluent. Single crystals suitable for X-ray diffraction were prepared by evaporation of a methanol solution of the product.

Refinement

In absence of significant anomalous dispersion effects, Friedel pairs were merged. The absolute configuration was assigned by reference to the known configuration of the starting material. One methanol molecule is disordered over two positions, and corresponding site occupation factors were refined to 0.522 (5) and 0.478 (5). All H atoms of N—H groups were located in a difference map and refined freely. All H atoms for O—H groups were placed in idealized positions, with O—H bond lengths of 0.84 Å. Other H atoms were positioned geometrically and refined using a riding model, with C—H bond lengths in the range 0.95–0.99 Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl).

Figures

Fig. 1.
The molecular structure of the main molecules, with atom labels and 50% probability displacement ellipsoids for non-H atoms. The crystal is a methanol solvate, with a 1:1 composition with respect to the main molecule. Solvent molecules were omitted.

Crystal data

C33H30N2O10·CH4OF000 = 1360
Mr = 646.63Dx = 1.345 Mg m3
Monoclinic, P21Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 8161 reflections
a = 12.228 (2) Åθ = 1.7–27.5º
b = 9.8360 (16) ŵ = 0.10 mm1
c = 26.667 (5) ÅT = 113 (2) K
β = 95.58 (3)ºPlate, yellow
V = 3192.2 (9) Å30.24 × 0.22 × 0.12 mm
Z = 4

Data collection

Rigaku Saturn CCD area-detector diffractometer7730 independent reflections
Radiation source: rotating anode6754 reflections with I > 2σ(I)
Monochromator: confocalRint = 0.045
Detector resolution: 7.31 pixels mm-1θmax = 27.5º
T = 113(2) Kθmin = 1.5º
ω and [var phi] scansh = −15→15
Absorption correction: multi-scan(CrystalClear; Rigaku/MSC, 2005)k = −12→11
Tmin = 0.976, Tmax = 0.988l = −31→34
22853 measured reflections

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.047  w = 1/[σ2(Fo2) + (0.0825P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.127(Δ/σ)max = 0.001
S = 1.03Δρmax = 0.73 e Å3
7730 reflectionsΔρmin = −0.27 e Å3
893 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0201 (14)
Secondary atom site location: difference Fourier map

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
O10.9709 (2)0.2102 (3)0.43373 (9)0.0355 (6)
O20.83051 (16)0.5566 (2)0.29071 (8)0.0237 (5)
O30.56989 (19)0.5637 (3)0.22380 (9)0.0430 (7)
O40.7776 (2)1.1791 (3)0.23313 (9)0.0381 (6)
O50.89806 (19)1.2324 (3)0.17487 (9)0.0344 (6)
O60.74319 (19)0.4426 (2)0.07044 (9)0.0318 (5)
O70.8771 (2)0.5210 (2)0.02670 (9)0.0338 (5)
O80.51000 (18)1.0135 (3)−0.01957 (8)0.0303 (5)
O90.59367 (17)0.9543 (2)−0.10683 (8)0.0251 (5)
O100.79144 (17)0.8430 (3)−0.10779 (8)0.0285 (5)
O111.10961 (19)0.6741 (2)0.06729 (8)0.0293 (5)
O120.96392 (17)0.7624 (2)0.23470 (8)0.0252 (5)
O131.0023 (2)1.0455 (3)0.31461 (8)0.0324 (5)
O140.45644 (19)0.9379 (3)0.28103 (9)0.0392 (6)
O150.39852 (17)0.7404 (3)0.31787 (9)0.0350 (6)
O161.05011 (18)0.7382 (3)0.45386 (8)0.0312 (5)
O170.97883 (19)0.5355 (2)0.47195 (8)0.0296 (5)
O180.59318 (19)0.8892 (2)0.55775 (8)0.0273 (5)
O190.61900 (16)0.6673 (2)0.61567 (7)0.0238 (5)
O200.7020 (2)0.4377 (2)0.58168 (8)0.0319 (5)
N10.5534 (2)0.3107 (3)0.34849 (10)0.0280 (6)
H10.490 (3)0.275 (4)0.3584 (14)0.034*
N20.7327 (2)0.6542 (3)0.20608 (9)0.0229 (5)
H20.812 (3)0.671 (4)0.2177 (13)0.027*
N31.2084 (2)1.0934 (3)0.19960 (10)0.0249 (6)
H3A1.252 (3)1.166 (4)0.2089 (14)0.030*
N40.8928 (2)0.8590 (3)0.31837 (9)0.0212 (5)
H4A0.865 (3)0.788 (4)0.3026 (13)0.025*
C11.0619 (3)0.2694 (4)0.41211 (13)0.0358 (8)
H1A1.06010.24240.37670.054*
H1B1.13060.23790.43040.054*
H1C1.05760.36870.41440.054*
C20.8683 (3)0.2420 (3)0.41280 (12)0.0261 (7)
C30.7839 (3)0.1797 (3)0.43615 (12)0.0294 (7)
H30.80150.12540.46530.035*
C40.6750 (3)0.1962 (3)0.41739 (12)0.0292 (7)
H40.61730.15320.43290.035*
C50.6535 (3)0.2779 (3)0.37513 (11)0.0242 (6)
C60.5696 (3)0.3946 (3)0.31033 (11)0.0262 (7)
H60.51340.43010.28690.031*
C70.6824 (2)0.4218 (3)0.31032 (11)0.0216 (6)
C80.7367 (2)0.3440 (3)0.35189 (10)0.0200 (6)
C90.8474 (2)0.3262 (3)0.37056 (11)0.0232 (6)
H90.90520.36930.35520.028*
C100.7340 (2)0.5197 (3)0.28133 (10)0.0202 (6)
C110.6682 (2)0.5823 (3)0.23466 (11)0.0252 (7)
C120.6859 (2)0.7245 (3)0.16045 (11)0.0238 (6)
H120.60600.74000.16340.029*
C130.6968 (2)0.6420 (3)0.11236 (11)0.0227 (6)
H130.64320.67940.08510.027*
C140.6835 (3)0.4872 (4)0.11279 (13)0.0305 (7)
H14A0.71630.44790.14500.037*
H14B0.60510.46100.10750.037*
C150.8175 (3)0.5382 (3)0.05986 (12)0.0268 (7)
C160.8111 (2)0.6562 (3)0.09543 (10)0.0211 (6)
H160.86420.63680.12550.025*
C170.8347 (2)0.8009 (3)0.07850 (10)0.0195 (6)
H170.91440.80650.07320.023*
C180.8143 (2)0.8956 (3)0.12187 (11)0.0209 (6)
C190.8700 (2)1.0211 (3)0.12473 (11)0.0236 (6)
H190.91811.04610.10040.028*
C200.8522 (2)1.1066 (3)0.16423 (12)0.0254 (6)
C210.8708 (3)1.2608 (4)0.22494 (13)0.0362 (8)
H21A0.93341.23810.24990.043*
H21B0.85311.35840.22840.043*
C220.7809 (3)1.0735 (3)0.19899 (12)0.0278 (7)
C230.7237 (2)0.9546 (4)0.19687 (11)0.0260 (7)
H230.67330.93440.22080.031*
C240.7416 (2)0.8628 (3)0.15812 (10)0.0222 (6)
C250.7684 (2)0.8429 (3)0.02942 (10)0.0196 (6)
C260.6673 (2)0.9084 (3)0.02973 (11)0.0225 (6)
H260.63830.92710.06080.027*
C270.6086 (2)0.9465 (3)−0.01582 (11)0.0225 (6)
C280.6521 (2)0.9191 (3)−0.06129 (11)0.0233 (6)
C290.7545 (2)0.8577 (3)−0.06123 (11)0.0213 (6)
C300.8123 (2)0.8184 (3)−0.01594 (11)0.0226 (6)
H300.88160.7748−0.01600.027*
C310.4672 (3)1.0519 (5)0.02636 (14)0.0418 (9)
H31A0.45440.97020.04600.063*
H31B0.39781.10080.01870.063*
H31C0.52021.11090.04590.063*
C320.6137 (3)1.0929 (4)−0.12153 (14)0.0344 (8)
H32A0.58771.1554−0.09670.052*
H32B0.57441.1109−0.15470.052*
H32C0.69271.1063−0.12320.052*
C330.9057 (3)0.8143 (5)−0.10879 (13)0.0363 (8)
H33A0.94910.8824−0.08880.054*
H33B0.92450.8170−0.14370.054*
H33C0.92180.7237−0.09460.054*
C341.1325 (3)0.6781 (4)0.01564 (12)0.0318 (7)
H34A1.11130.76700.00120.048*
H34B1.09060.6066−0.00320.048*
H34C1.21120.66340.01360.048*
C351.1422 (2)0.7832 (3)0.09760 (11)0.0228 (6)
C361.2157 (2)0.8833 (3)0.08386 (12)0.0256 (6)
H361.24490.87790.05220.031*
C371.2456 (3)0.9898 (3)0.11633 (12)0.0268 (7)
H371.29591.05750.10760.032*
C381.1995 (2)0.9946 (3)0.16239 (11)0.0235 (6)
C391.1422 (2)1.0624 (3)0.23537 (11)0.0220 (6)
H391.13371.11590.26440.026*
C401.0877 (2)0.9400 (3)0.22359 (11)0.0208 (6)
C411.1253 (2)0.8955 (3)0.17615 (11)0.0196 (6)
C421.0986 (2)0.7857 (3)0.14365 (11)0.0214 (6)
H421.05170.71480.15300.026*
C431.0061 (2)0.8723 (3)0.24936 (10)0.0206 (6)
C440.9674 (2)0.9361 (3)0.29783 (10)0.0216 (6)
C450.8387 (2)0.9029 (3)0.36257 (10)0.0218 (6)
H450.84021.00440.36440.026*
C460.8942 (2)0.8449 (3)0.41195 (11)0.0221 (6)
H460.85860.88600.44060.027*
C471.0178 (3)0.8571 (4)0.42313 (12)0.0289 (7)
H47A1.05420.85670.39160.035*
H47B1.03750.94200.44180.035*
C480.9684 (3)0.6421 (3)0.45032 (11)0.0254 (7)
C490.8766 (2)0.6920 (3)0.41273 (11)0.0216 (6)
H490.89440.65810.37910.026*
C500.7568 (2)0.6525 (3)0.41697 (10)0.0210 (6)
H500.74860.55580.40570.025*
C510.6837 (2)0.7376 (3)0.37934 (10)0.0208 (6)
C520.5740 (2)0.6926 (3)0.36810 (11)0.0235 (6)
H520.54840.61290.38340.028*
C530.5061 (2)0.7661 (3)0.33488 (12)0.0257 (7)
C540.3728 (4)0.8367 (6)0.2790 (2)0.0734 (17)
H54A0.30100.87960.28320.088*
H54B0.36730.79060.24580.088*
C550.5417 (3)0.8846 (4)0.31276 (12)0.0284 (7)
C560.6461 (2)0.9325 (3)0.32251 (11)0.0247 (6)
H560.66911.01400.30760.030*
C570.7191 (2)0.8550 (3)0.35611 (10)0.0203 (6)
C580.7206 (2)0.6588 (3)0.47014 (11)0.0202 (6)
C590.6749 (2)0.7768 (3)0.48856 (11)0.0216 (6)
H590.66640.85540.46790.026*
C600.6418 (2)0.7796 (3)0.53700 (11)0.0197 (6)
C610.6544 (2)0.6648 (3)0.56788 (11)0.0207 (6)
C620.6964 (2)0.5457 (3)0.54896 (11)0.0212 (6)
C630.7300 (2)0.5425 (3)0.50054 (11)0.0235 (6)
H630.75950.46120.48810.028*
C640.5741 (3)1.0045 (3)0.52584 (13)0.0303 (7)
H64A0.64461.04260.51820.045*
H64B0.53311.07320.54290.045*
H64C0.53150.97700.49450.045*
C650.7057 (3)0.6693 (6)0.65580 (12)0.0495 (12)
H65A0.75800.59630.65080.074*
H65B0.67480.65590.68800.074*
H65C0.74350.75720.65610.074*
C660.6889 (3)0.3055 (3)0.55972 (13)0.0300 (7)
H66A0.62290.30400.53580.045*
H66B0.68160.23820.58630.045*
H66C0.75340.28370.54210.045*
O210.3925 (2)0.2634 (4)0.18772 (15)0.0800 (13)
H210.38690.32510.16590.120*
C670.4991 (4)0.2072 (5)0.19056 (18)0.0584 (13)
H67A0.55360.27960.19740.088*
H67B0.51030.16310.15850.088*
H67C0.50750.13990.21780.088*
O220.1884 (6)0.3747 (4)0.24506 (19)0.0478 (17)0.522 (5)
H220.13010.39320.25790.072*0.522 (5)
C680.2343 (10)0.4948 (7)0.2278 (3)0.065 (3)0.522 (5)
H68A0.18540.57150.23280.097*0.522 (5)
H68B0.24370.48590.19190.097*0.522 (5)
H68C0.30600.51080.24670.097*0.522 (5)
O230.0596 (3)0.4971 (5)0.3106 (2)0.0326 (13)0.478 (5)
H23A0.07920.48530.28160.049*0.478 (5)
C690.1315 (5)0.5923 (8)0.3374 (3)0.0304 (16)0.478 (5)
H69A0.13700.67430.31690.046*0.478 (5)
H69B0.20450.55160.34440.046*0.478 (5)
H69C0.10240.61640.36910.046*0.478 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0363 (13)0.0429 (14)0.0266 (13)0.0155 (12)0.0001 (10)0.0051 (10)
O20.0213 (10)0.0284 (11)0.0208 (11)−0.0039 (9)−0.0014 (8)0.0040 (9)
O30.0254 (11)0.0656 (19)0.0363 (14)−0.0155 (12)−0.0068 (10)0.0265 (13)
O40.0387 (13)0.0425 (15)0.0340 (14)−0.0010 (12)0.0082 (10)−0.0162 (12)
O50.0371 (13)0.0304 (12)0.0361 (14)−0.0064 (11)0.0060 (10)−0.0111 (11)
O60.0366 (12)0.0269 (12)0.0304 (12)−0.0036 (11)−0.0037 (10)−0.0030 (10)
O70.0407 (13)0.0297 (13)0.0307 (13)0.0034 (11)0.0017 (10)−0.0055 (10)
O80.0249 (11)0.0442 (14)0.0213 (11)0.0112 (10)−0.0004 (8)−0.0018 (10)
O90.0253 (10)0.0310 (12)0.0175 (10)−0.0014 (10)−0.0055 (8)0.0018 (9)
O100.0259 (11)0.0428 (13)0.0172 (11)0.0039 (10)0.0034 (8)−0.0004 (10)
O110.0388 (12)0.0294 (12)0.0207 (11)−0.0006 (10)0.0074 (9)−0.0050 (9)
O120.0261 (10)0.0260 (11)0.0244 (11)−0.0060 (9)0.0068 (8)−0.0036 (9)
O130.0405 (13)0.0311 (12)0.0271 (12)−0.0126 (11)0.0110 (10)−0.0063 (10)
O140.0284 (12)0.0488 (16)0.0386 (14)0.0029 (12)−0.0063 (10)0.0109 (12)
O150.0224 (11)0.0519 (16)0.0297 (12)−0.0015 (11)−0.0033 (9)0.0046 (11)
O160.0275 (11)0.0417 (13)0.0235 (12)−0.0037 (11)−0.0026 (9)0.0051 (10)
O170.0359 (12)0.0297 (12)0.0229 (11)0.0067 (10)0.0019 (9)0.0017 (10)
O180.0383 (12)0.0229 (11)0.0221 (11)0.0075 (10)0.0099 (9)0.0011 (9)
O190.0262 (10)0.0305 (11)0.0155 (10)0.0048 (9)0.0063 (8)0.0044 (9)
O200.0516 (14)0.0228 (11)0.0225 (11)0.0046 (11)0.0091 (10)0.0051 (9)
N10.0249 (13)0.0355 (16)0.0239 (14)−0.0089 (12)0.0031 (10)0.0049 (11)
N20.0196 (12)0.0315 (14)0.0170 (12)−0.0044 (11)−0.0013 (9)0.0077 (11)
N30.0254 (12)0.0260 (14)0.0231 (13)−0.0092 (12)0.0013 (10)0.0005 (10)
N40.0240 (12)0.0241 (13)0.0161 (12)−0.0037 (11)0.0043 (9)−0.0018 (10)
C10.0304 (17)0.046 (2)0.0301 (18)0.0113 (16)−0.0041 (13)−0.0047 (16)
C20.0342 (16)0.0246 (15)0.0193 (15)0.0072 (14)0.0015 (12)−0.0019 (12)
C30.0482 (19)0.0238 (16)0.0170 (15)0.0076 (15)0.0075 (13)0.0025 (12)
C40.0441 (18)0.0257 (17)0.0188 (15)−0.0033 (15)0.0088 (13)0.0027 (12)
C50.0305 (15)0.0228 (15)0.0197 (15)−0.0030 (13)0.0039 (12)0.0003 (12)
C60.0257 (15)0.0341 (17)0.0186 (15)−0.0069 (14)0.0016 (11)0.0053 (13)
C70.0228 (14)0.0240 (15)0.0181 (14)−0.0034 (13)0.0022 (11)0.0013 (11)
C80.0291 (15)0.0165 (13)0.0149 (13)−0.0001 (12)0.0041 (11)−0.0022 (11)
C90.0262 (14)0.0200 (15)0.0237 (15)0.0009 (13)0.0042 (12)−0.0033 (12)
C100.0197 (13)0.0250 (15)0.0161 (13)−0.0026 (12)0.0032 (10)−0.0014 (11)
C110.0256 (14)0.0327 (17)0.0164 (14)−0.0040 (13)−0.0014 (11)0.0047 (12)
C120.0220 (14)0.0313 (16)0.0174 (14)−0.0017 (13)−0.0018 (11)0.0056 (12)
C130.0226 (14)0.0270 (16)0.0176 (14)−0.0034 (12)−0.0034 (11)0.0043 (12)
C140.0326 (16)0.0294 (17)0.0283 (17)−0.0092 (14)−0.0035 (13)0.0062 (14)
C150.0291 (15)0.0239 (15)0.0261 (16)0.0025 (14)−0.0048 (12)−0.0012 (13)
C160.0217 (13)0.0251 (15)0.0158 (14)−0.0011 (12)−0.0021 (11)0.0003 (11)
C170.0186 (13)0.0243 (15)0.0155 (13)0.0008 (12)0.0011 (10)−0.0017 (11)
C180.0214 (13)0.0237 (15)0.0171 (14)0.0025 (12)−0.0004 (11)0.0012 (11)
C190.0228 (14)0.0256 (16)0.0228 (15)0.0012 (13)0.0034 (11)0.0012 (12)
C200.0238 (14)0.0262 (15)0.0257 (16)0.0005 (13)0.0007 (12)−0.0015 (12)
C210.0429 (19)0.0313 (18)0.0336 (19)−0.0021 (16)0.0002 (15)−0.0104 (15)
C220.0292 (16)0.0317 (18)0.0227 (16)0.0057 (14)0.0023 (12)−0.0073 (13)
C230.0262 (15)0.0341 (18)0.0185 (15)0.0001 (14)0.0059 (11)0.0024 (13)
C240.0209 (13)0.0307 (16)0.0146 (13)0.0008 (13)−0.0001 (10)0.0013 (12)
C250.0225 (13)0.0193 (14)0.0165 (13)0.0008 (12)−0.0006 (10)0.0010 (11)
C260.0221 (13)0.0251 (15)0.0203 (14)0.0006 (12)0.0021 (11)0.0021 (12)
C270.0190 (13)0.0268 (16)0.0214 (14)0.0001 (12)0.0003 (11)0.0016 (12)
C280.0242 (14)0.0257 (15)0.0189 (14)0.0008 (13)−0.0036 (11)0.0006 (12)
C290.0241 (14)0.0241 (15)0.0161 (13)0.0006 (13)0.0039 (10)−0.0029 (11)
C300.0195 (13)0.0256 (16)0.0222 (15)0.0008 (12)−0.0006 (11)−0.0008 (12)
C310.0315 (18)0.065 (3)0.0295 (18)0.0187 (19)0.0044 (14)−0.0022 (18)
C320.0369 (18)0.0341 (19)0.0296 (18)−0.0012 (15)−0.0102 (14)0.0079 (14)
C330.0264 (16)0.060 (2)0.0233 (17)0.0033 (17)0.0080 (12)−0.0068 (16)
C340.0459 (19)0.0319 (17)0.0177 (15)0.0054 (16)0.0036 (13)−0.0037 (13)
C350.0236 (14)0.0237 (15)0.0211 (15)0.0034 (13)0.0020 (11)−0.0009 (12)
C360.0262 (15)0.0294 (17)0.0221 (15)0.0008 (13)0.0067 (12)0.0020 (13)
C370.0271 (15)0.0299 (16)0.0244 (16)−0.0056 (14)0.0078 (12)0.0037 (13)
C380.0220 (14)0.0267 (15)0.0217 (15)−0.0021 (12)0.0019 (11)0.0022 (12)
C390.0203 (13)0.0276 (16)0.0177 (14)−0.0021 (12)0.0003 (10)0.0015 (12)
C400.0208 (13)0.0240 (15)0.0168 (13)−0.0014 (12)−0.0014 (10)0.0012 (11)
C410.0156 (12)0.0231 (15)0.0204 (14)0.0018 (11)0.0025 (10)0.0019 (11)
C420.0180 (13)0.0259 (15)0.0202 (15)0.0014 (12)0.0019 (10)0.0015 (12)
C430.0217 (13)0.0247 (15)0.0156 (13)−0.0017 (12)0.0021 (10)−0.0007 (11)
C440.0225 (13)0.0266 (15)0.0154 (13)−0.0004 (13)0.0009 (10)−0.0002 (12)
C450.0261 (14)0.0243 (15)0.0158 (14)−0.0039 (12)0.0063 (11)−0.0011 (11)
C460.0248 (14)0.0271 (15)0.0152 (14)−0.0017 (13)0.0054 (11)0.0000 (11)
C470.0296 (16)0.0368 (18)0.0199 (15)−0.0076 (15)−0.0001 (12)0.0021 (13)
C480.0251 (14)0.0316 (18)0.0200 (15)0.0035 (13)0.0041 (11)−0.0053 (13)
C490.0214 (14)0.0276 (16)0.0159 (14)0.0001 (12)0.0019 (11)−0.0037 (11)
C500.0255 (14)0.0217 (15)0.0160 (14)0.0001 (12)0.0024 (11)−0.0005 (11)
C510.0241 (14)0.0257 (15)0.0129 (13)0.0001 (13)0.0042 (11)−0.0038 (11)
C520.0241 (14)0.0275 (16)0.0196 (15)−0.0009 (13)0.0059 (11)−0.0009 (12)
C530.0216 (14)0.0338 (17)0.0220 (15)−0.0028 (13)0.0041 (11)−0.0039 (13)
C540.045 (2)0.072 (3)0.096 (4)−0.017 (2)−0.029 (2)0.045 (3)
C550.0277 (15)0.0354 (18)0.0212 (15)0.0058 (14)−0.0026 (12)0.0018 (13)
C560.0309 (15)0.0264 (16)0.0173 (14)−0.0005 (14)0.0051 (11)0.0001 (12)
C570.0217 (13)0.0249 (15)0.0143 (13)−0.0004 (12)0.0023 (10)−0.0035 (11)
C580.0209 (13)0.0212 (14)0.0189 (14)−0.0041 (12)0.0029 (11)−0.0007 (11)
C590.0251 (14)0.0201 (14)0.0193 (14)−0.0004 (12)0.0010 (11)0.0020 (11)
C600.0169 (12)0.0225 (15)0.0196 (14)0.0013 (12)0.0018 (10)−0.0039 (12)
C610.0188 (13)0.0277 (15)0.0159 (13)−0.0012 (12)0.0036 (10)0.0002 (12)
C620.0235 (14)0.0200 (14)0.0200 (14)0.0000 (12)0.0012 (11)0.0048 (12)
C630.0264 (15)0.0207 (14)0.0234 (15)0.0010 (13)0.0024 (11)−0.0017 (12)
C640.0374 (17)0.0230 (16)0.0319 (18)0.0067 (14)0.0108 (14)0.0035 (13)
C650.0361 (18)0.099 (4)0.0131 (16)0.017 (2)−0.0003 (13)−0.0042 (19)
C660.0288 (16)0.0245 (16)0.0369 (19)0.0046 (14)0.0040 (13)0.0034 (14)
O210.0418 (16)0.083 (3)0.109 (3)−0.0281 (18)−0.0256 (17)0.069 (2)
C670.051 (2)0.062 (3)0.060 (3)−0.007 (2)−0.011 (2)0.027 (2)
O220.095 (5)0.017 (2)0.034 (3)−0.002 (3)0.022 (3)−0.0010 (19)
C680.141 (10)0.025 (4)0.031 (4)−0.021 (5)0.019 (5)−0.005 (3)
O230.0067 (19)0.039 (3)0.053 (3)0.0004 (19)0.0034 (19)0.008 (2)
C690.022 (3)0.040 (4)0.030 (4)0.005 (3)0.005 (3)−0.009 (3)

Geometric parameters (Å, °)

O1—C21.359 (4)C26—C271.400 (4)
O1—C11.426 (5)C26—H260.9500
O2—C101.236 (3)C27—C281.397 (4)
O3—C111.223 (4)C28—C291.390 (4)
O4—C221.384 (4)C29—C301.393 (4)
O4—C211.428 (4)C30—H300.9500
O5—C201.377 (4)C31—H31A0.9800
O5—C211.435 (4)C31—H31B0.9800
O6—C151.356 (4)C31—H31C0.9800
O6—C141.470 (4)C32—H32A0.9800
O7—C151.212 (4)C32—H32B0.9800
O8—C271.370 (4)C32—H32C0.9800
O8—C311.429 (4)C33—H33A0.9800
O9—C281.392 (3)C33—H33B0.9800
O9—C321.446 (4)C33—H33C0.9800
O10—C291.369 (3)C34—H34A0.9800
O10—C331.428 (4)C34—H34B0.9800
O11—C351.379 (4)C34—H34C0.9800
O11—C341.432 (4)C35—C421.386 (4)
O12—C431.244 (4)C35—C361.405 (4)
O13—C441.226 (4)C36—C371.386 (5)
O14—C551.380 (4)C36—H360.9500
O14—C541.425 (5)C37—C381.401 (4)
O15—C531.373 (4)C37—H370.9500
O15—C541.417 (5)C38—C411.404 (4)
O16—C481.372 (4)C39—C401.397 (4)
O16—C471.460 (4)C39—H390.9500
O17—C481.198 (4)C40—C431.430 (4)
O18—C601.373 (4)C40—C411.455 (4)
O18—C641.423 (4)C41—C421.404 (4)
O19—C611.385 (3)C42—H420.9500
O19—C651.431 (4)C43—C441.551 (4)
O20—C621.372 (4)C45—C571.530 (4)
O20—C661.429 (4)C45—C461.532 (4)
N1—C61.339 (4)C45—H451.0000
N1—C51.391 (4)C46—C471.516 (4)
N1—H10.92 (4)C46—C491.520 (4)
N2—C111.349 (4)C46—H461.0000
N2—C121.467 (4)C47—H47A0.9900
N2—H21.00 (4)C47—H47B0.9900
N3—C391.345 (4)C48—C491.512 (4)
N3—C381.386 (4)C49—C501.530 (4)
N3—H3A0.91 (4)C49—H491.0000
N4—C441.344 (4)C50—C581.527 (4)
N4—C451.471 (4)C50—C511.528 (4)
N4—H4A0.87 (4)C50—H501.0000
C1—H1A0.9800C51—C571.399 (4)
C1—H1B0.9800C51—C521.416 (4)
C1—H1C0.9800C52—C531.361 (4)
C2—C31.398 (5)C52—H520.9500
C2—C91.402 (4)C53—C551.395 (5)
C3—C41.386 (5)C54—H54A0.9900
C3—H30.9500C54—H54B0.9900
C4—C51.388 (4)C55—C561.362 (4)
C4—H40.9500C56—C571.423 (4)
C5—C81.402 (4)C56—H560.9500
C6—C71.406 (4)C58—C591.397 (4)
C6—H60.9500C58—C631.400 (4)
C7—C101.421 (4)C59—C601.391 (4)
C7—C81.453 (4)C59—H590.9500
C8—C91.407 (4)C60—C611.397 (4)
C9—H90.9500C61—C621.393 (4)
C10—C111.543 (4)C62—C631.393 (4)
C12—C241.525 (5)C63—H630.9500
C12—C131.534 (4)C64—H64A0.9800
C12—H121.0000C64—H64B0.9800
C13—C161.517 (4)C64—H64C0.9800
C13—C141.531 (5)C65—H65A0.9800
C13—H131.0000C65—H65B0.9800
C14—H14A0.9900C65—H65C0.9800
C14—H14B0.9900C66—H66A0.9800
C15—C161.506 (4)C66—H66B0.9800
C16—C171.529 (4)C66—H66C0.9800
C16—H161.0000O21—C671.411 (6)
C17—C181.524 (4)O21—H210.8400
C17—C251.528 (4)C67—H67A0.9800
C17—H171.0000C67—H67B0.9800
C18—C191.408 (4)C67—H67C0.9800
C18—C241.412 (4)O22—C681.405 (7)
C19—C201.382 (4)O22—H220.8400
C19—H190.9500C68—H68A0.9800
C20—C221.372 (5)C68—H68B0.9800
C21—H21A0.9900C68—H68C0.9800
C21—H21B0.9900O23—C691.428 (7)
C22—C231.361 (5)O23—H23A0.8400
C23—C241.406 (4)C69—H69A0.9800
C23—H230.9500C69—H69B0.9800
C25—C301.391 (4)C69—H69C0.9800
C25—C261.395 (4)
C2—O1—C1117.7 (3)H33A—C33—H33C109.5
C22—O4—C21104.3 (2)H33B—C33—H33C109.5
C20—O5—C21103.9 (3)O11—C34—H34A109.5
C15—O6—C14110.2 (2)O11—C34—H34B109.5
C27—O8—C31117.2 (2)H34A—C34—H34B109.5
C28—O9—C32112.6 (2)O11—C34—H34C109.5
C29—O10—C33116.6 (2)H34A—C34—H34C109.5
C35—O11—C34118.0 (3)H34B—C34—H34C109.5
C55—O14—C54104.8 (3)O11—C35—C42114.7 (3)
C53—O15—C54104.9 (3)O11—C35—C36123.3 (3)
C48—O16—C47110.9 (2)C42—C35—C36122.0 (3)
C60—O18—C64115.9 (2)C37—C36—C35120.3 (3)
C61—O19—C65114.4 (2)C37—C36—H36119.9
C62—O20—C66116.6 (2)C35—C36—H36119.9
C6—N1—C5110.1 (3)C36—C37—C38117.9 (3)
C6—N1—H1130 (2)C36—C37—H37121.0
C5—N1—H1120 (2)C38—C37—H37121.0
C11—N2—C12120.9 (2)N3—C38—C37129.8 (3)
C11—N2—H2121 (2)N3—C38—C41107.9 (2)
C12—N2—H2118 (2)C37—C38—C41122.1 (3)
C39—N3—C38109.7 (3)N3—C39—C40110.1 (3)
C39—N3—H3A111 (2)N3—C39—H39125.0
C38—N3—H3A138 (2)C40—C39—H39125.0
C44—N4—C45122.5 (3)C39—C40—C43129.3 (3)
C44—N4—H4A121 (2)C39—C40—C41105.7 (3)
C45—N4—H4A116 (2)C43—C40—C41124.9 (3)
O1—C1—H1A109.5C38—C41—C42119.4 (3)
O1—C1—H1B109.5C38—C41—C40106.6 (3)
H1A—C1—H1B109.5C42—C41—C40133.9 (3)
O1—C1—H1C109.5C35—C42—C41118.2 (3)
H1A—C1—H1C109.5C35—C42—H42120.9
H1B—C1—H1C109.5C41—C42—H42120.9
O1—C2—C3114.1 (3)O12—C43—C40122.7 (3)
O1—C2—C9123.8 (3)O12—C43—C44117.6 (3)
C3—C2—C9122.1 (3)C40—C43—C44119.7 (3)
C4—C3—C2120.9 (3)O13—C44—N4125.0 (3)
C4—C3—H3119.6O13—C44—C43122.4 (3)
C2—C3—H3119.6N4—C44—C43112.7 (3)
C3—C4—C5117.4 (3)N4—C45—C57108.6 (2)
C3—C4—H4121.3N4—C45—C46112.6 (2)
C5—C4—H4121.3C57—C45—C46108.7 (2)
C4—C5—N1129.6 (3)N4—C45—H45109.0
C4—C5—C8122.6 (3)C57—C45—H45109.0
N1—C5—C8107.8 (3)C46—C45—H45109.0
N1—C6—C7109.6 (3)C47—C46—C49102.4 (3)
N1—C6—H6125.2C47—C46—C45119.3 (2)
C7—C6—H6125.2C49—C46—C45109.2 (2)
C6—C7—C10128.1 (3)C47—C46—H46108.5
C6—C7—C8105.9 (3)C49—C46—H46108.5
C10—C7—C8125.3 (3)C45—C46—H46108.5
C5—C8—C9120.0 (3)O16—C47—C46104.9 (2)
C5—C8—C7106.5 (3)O16—C47—H47A110.8
C9—C8—C7133.4 (3)C46—C47—H47A110.8
C2—C9—C8116.9 (3)O16—C47—H47B110.8
C2—C9—H9121.6C46—C47—H47B110.8
C8—C9—H9121.6H47A—C47—H47B108.8
O2—C10—C7123.7 (3)O17—C48—O16121.8 (3)
O2—C10—C11117.3 (3)O17—C48—C49129.8 (3)
C7—C10—C11119.0 (2)O16—C48—C49108.1 (3)
O3—C11—N2124.1 (3)C48—C49—C46103.5 (2)
O3—C11—C10123.7 (3)C48—C49—C50121.5 (3)
N2—C11—C10112.1 (2)C46—C49—C50113.0 (3)
N2—C12—C24108.4 (2)C48—C49—H49105.9
N2—C12—C13112.7 (3)C46—C49—H49105.9
C24—C12—C13111.3 (2)C50—C49—H49105.9
N2—C12—H12108.1C58—C50—C51112.5 (2)
C24—C12—H12108.1C58—C50—C49115.1 (2)
C13—C12—H12108.1C51—C50—C49108.4 (2)
C16—C13—C14101.3 (3)C58—C50—H50106.8
C16—C13—C12110.9 (2)C51—C50—H50106.8
C14—C13—C12120.1 (3)C49—C50—H50106.8
C16—C13—H13108.0C57—C51—C52119.5 (3)
C14—C13—H13108.0C57—C51—C50123.8 (3)
C12—C13—H13108.0C52—C51—C50116.7 (3)
O6—C14—C13103.3 (3)C53—C52—C51118.4 (3)
O6—C14—H14A111.1C53—C52—H52120.8
C13—C14—H14A111.1C51—C52—H52120.8
O6—C14—H14B111.1C52—C53—O15128.4 (3)
C13—C14—H14B111.1C52—C53—C55121.6 (3)
H14A—C14—H14B109.1O15—C53—C55110.0 (3)
O7—C15—O6121.2 (3)O15—C54—O14109.4 (3)
O7—C15—C16129.7 (3)O15—C54—H54A109.8
O6—C15—C16109.1 (3)O14—C54—H54A109.8
C15—C16—C13102.8 (2)O15—C54—H54B109.8
C15—C16—C17120.6 (2)O14—C54—H54B109.8
C13—C16—C17112.3 (2)H54A—C54—H54B108.3
C15—C16—H16106.8C56—C55—O14128.6 (3)
C13—C16—H16106.8C56—C55—C53122.2 (3)
C17—C16—H16106.8O14—C55—C53109.2 (3)
C18—C17—C25111.9 (2)C55—C56—C57117.0 (3)
C18—C17—C16107.2 (2)C55—C56—H56121.5
C25—C17—C16113.9 (2)C57—C56—H56121.5
C18—C17—H17107.9C51—C57—C56121.2 (3)
C25—C17—H17107.9C51—C57—C45122.6 (3)
C16—C17—H17107.9C56—C57—C45116.1 (3)
C19—C18—C24119.8 (3)C59—C58—C63119.2 (3)
C19—C18—C17117.5 (3)C59—C58—C50121.5 (3)
C24—C18—C17122.7 (3)C63—C58—C50119.3 (3)
C20—C19—C18117.6 (3)C60—C59—C58120.4 (3)
C20—C19—H19121.2C60—C59—H59119.8
C18—C19—H19121.2C58—C59—H59119.8
C22—C20—O5110.3 (3)O18—C60—C59124.5 (3)
C22—C20—C19121.9 (3)O18—C60—C61115.1 (2)
O5—C20—C19127.8 (3)C59—C60—C61120.4 (3)
O4—C21—O5107.1 (3)O19—C61—C62120.4 (3)
O4—C21—H21A110.3O19—C61—C60120.2 (3)
O5—C21—H21A110.3C62—C61—C60119.3 (3)
O4—C21—H21B110.3O20—C62—C63124.8 (3)
O5—C21—H21B110.3O20—C62—C61114.7 (3)
H21A—C21—H21B108.6C63—C62—C61120.5 (3)
C23—C22—C20122.2 (3)C62—C63—C58120.2 (3)
C23—C22—O4128.6 (3)C62—C63—H63119.9
C20—C22—O4109.1 (3)C58—C63—H63119.9
C22—C23—C24117.8 (3)O18—C64—H64A109.5
C22—C23—H23121.1O18—C64—H64B109.5
C24—C23—H23121.1H64A—C64—H64B109.5
C23—C24—C18120.6 (3)O18—C64—H64C109.5
C23—C24—C12116.2 (3)H64A—C64—H64C109.5
C18—C24—C12123.0 (3)H64B—C64—H64C109.5
C30—C25—C26120.2 (3)O19—C65—H65A109.5
C30—C25—C17118.7 (3)O19—C65—H65B109.5
C26—C25—C17121.1 (3)H65A—C65—H65B109.5
C25—C26—C27119.9 (3)O19—C65—H65C109.5
C25—C26—H26120.1H65A—C65—H65C109.5
C27—C26—H26120.1H65B—C65—H65C109.5
O8—C27—C28115.8 (3)O20—C66—H66A109.5
O8—C27—C26124.4 (3)O20—C66—H66B109.5
C28—C27—C26119.7 (3)H66A—C66—H66B109.5
C29—C28—O9119.7 (3)O20—C66—H66C109.5
C29—C28—C27120.1 (3)H66A—C66—H66C109.5
O9—C28—C27120.2 (3)H66B—C66—H66C109.5
O10—C29—C28114.9 (3)C67—O21—H21109.5
O10—C29—C30124.9 (3)O21—C67—H67A109.5
C28—C29—C30120.1 (3)O21—C67—H67B109.5
C25—C30—C29120.0 (3)H67A—C67—H67B109.5
C25—C30—H30120.0O21—C67—H67C109.5
C29—C30—H30120.0H67A—C67—H67C109.5
O8—C31—H31A109.5H67B—C67—H67C109.5
O8—C31—H31B109.5C68—O22—H22109.5
H31A—C31—H31B109.5O22—C68—H68A109.5
O8—C31—H31C109.5O22—C68—H68B109.5
H31A—C31—H31C109.5H68A—C68—H68B109.5
H31B—C31—H31C109.5O22—C68—H68C109.5
O9—C32—H32A109.5H68A—C68—H68C109.5
O9—C32—H32B109.5H68B—C68—H68C109.5
H32A—C32—H32B109.5C69—O23—H23A109.5
O9—C32—H32C109.5O23—C69—H69A109.5
H32A—C32—H32C109.5O23—C69—H69B109.5
H32B—C32—H32C109.5H69A—C69—H69B109.5
O10—C33—H33A109.5O23—C69—H69C109.5
O10—C33—H33B109.5H69A—C69—H69C109.5
H33A—C33—H33B109.5H69B—C69—H69C109.5
O10—C33—H33C109.5
C1—O1—C2—C3179.9 (3)C34—O11—C35—C42167.5 (3)
C1—O1—C2—C91.9 (5)C34—O11—C35—C36−13.8 (4)
O1—C2—C3—C4−176.4 (3)O11—C35—C36—C37−179.5 (3)
C9—C2—C3—C41.7 (5)C42—C35—C36—C37−0.9 (5)
C2—C3—C4—C5−0.8 (5)C35—C36—C37—C38−0.7 (5)
C3—C4—C5—N1179.4 (3)C39—N3—C38—C37174.3 (3)
C3—C4—C5—C8−0.9 (5)C39—N3—C38—C41−1.1 (3)
C6—N1—C5—C4179.1 (3)C36—C37—C38—N3−174.6 (3)
C6—N1—C5—C8−0.6 (4)C36—C37—C38—C410.2 (5)
C5—N1—C6—C7−0.4 (4)C38—N3—C39—C400.9 (3)
N1—C6—C7—C10−170.1 (3)N3—C39—C40—C43−176.5 (3)
N1—C6—C7—C81.2 (4)N3—C39—C40—C41−0.3 (3)
C4—C5—C8—C91.6 (5)N3—C38—C41—C42177.7 (3)
N1—C5—C8—C9−178.7 (3)C37—C38—C41—C421.9 (4)
C4—C5—C8—C7−178.4 (3)N3—C38—C41—C400.9 (3)
N1—C5—C8—C71.3 (3)C37—C38—C41—C40−174.9 (3)
C6—C7—C8—C5−1.5 (3)C39—C40—C41—C38−0.4 (3)
C10—C7—C8—C5170.1 (3)C43—C40—C41—C38176.1 (3)
C6—C7—C8—C9178.4 (3)C39—C40—C41—C42−176.6 (3)
C10—C7—C8—C9−9.9 (5)C43—C40—C41—C42−0.1 (5)
O1—C2—C9—C8176.9 (3)O11—C35—C42—C41−178.3 (2)
C3—C2—C9—C8−1.0 (5)C36—C35—C42—C413.0 (4)
C5—C8—C9—C2−0.6 (4)C38—C41—C42—C35−3.5 (4)
C7—C8—C9—C2179.4 (3)C40—C41—C42—C35172.4 (3)
C6—C7—C10—O2164.5 (3)C39—C40—C43—O12−179.9 (3)
C8—C7—C10—O2−5.2 (5)C41—C40—C43—O124.6 (5)
C6—C7—C10—C11−16.9 (5)C39—C40—C43—C44−0.1 (5)
C8—C7—C10—C11173.3 (3)C41—C40—C43—C44−175.7 (3)
C12—N2—C11—O34.4 (5)C45—N4—C44—O134.0 (5)
C12—N2—C11—C10−178.7 (3)C45—N4—C44—C43−175.8 (2)
O2—C10—C11—O3−173.4 (3)O12—C43—C44—O13−178.4 (3)
C7—C10—C11—O38.0 (5)C40—C43—C44—O131.9 (4)
O2—C10—C11—N29.7 (4)O12—C43—C44—N41.4 (4)
C7—C10—C11—N2−168.9 (3)C40—C43—C44—N4−178.4 (3)
C11—N2—C12—C24139.2 (3)C44—N4—C45—C57142.7 (3)
C11—N2—C12—C13−97.3 (3)C44—N4—C45—C46−96.9 (3)
N2—C12—C13—C16−80.5 (3)N4—C45—C46—C4749.4 (4)
C24—C12—C13—C1641.5 (3)C57—C45—C46—C47169.7 (3)
N2—C12—C13—C1437.2 (4)N4—C45—C46—C49−67.7 (3)
C24—C12—C13—C14159.1 (3)C57—C45—C46—C4952.6 (3)
C15—O6—C14—C1322.4 (3)C48—O16—C47—C4616.5 (3)
C16—C13—C14—O6−34.4 (3)C49—C46—C47—O16−29.1 (3)
C12—C13—C14—O6−156.9 (2)C45—C46—C47—O16−149.7 (3)
C14—O6—C15—O7178.7 (3)C47—O16—C48—O17178.7 (3)
C14—O6—C15—C16−0.3 (3)C47—O16—C48—C493.6 (3)
O7—C15—C16—C13159.0 (3)O17—C48—C49—C46163.3 (3)
O6—C15—C16—C13−22.1 (3)O16—C48—C49—C46−22.1 (3)
O7—C15—C16—C1733.1 (5)O17—C48—C49—C5035.2 (5)
O6—C15—C16—C17−148.0 (3)O16—C48—C49—C50−150.2 (3)
C14—C13—C16—C1534.0 (3)C47—C46—C49—C4830.8 (3)
C12—C13—C16—C15162.6 (2)C45—C46—C49—C48158.1 (2)
C14—C13—C16—C17165.1 (2)C47—C46—C49—C50164.0 (2)
C12—C13—C16—C17−66.3 (3)C45—C46—C49—C50−68.6 (3)
C15—C16—C17—C18176.5 (2)C48—C49—C50—C5843.4 (4)
C13—C16—C17—C1855.1 (3)C46—C49—C50—C58−80.4 (3)
C15—C16—C17—C2552.3 (4)C48—C49—C50—C51170.5 (3)
C13—C16—C17—C25−69.1 (3)C46—C49—C50—C5146.6 (3)
C25—C17—C18—C19−79.5 (3)C58—C50—C51—C57112.6 (3)
C16—C17—C18—C19155.0 (2)C49—C50—C51—C57−15.9 (4)
C25—C17—C18—C2499.6 (3)C58—C50—C51—C52−67.4 (3)
C16—C17—C18—C24−25.9 (4)C49—C50—C51—C52164.1 (3)
C24—C18—C19—C201.3 (4)C57—C51—C52—C53−0.2 (4)
C17—C18—C19—C20−179.5 (3)C50—C51—C52—C53179.7 (3)
C21—O5—C20—C2213.3 (3)C51—C52—C53—O15178.7 (3)
C21—O5—C20—C19−167.6 (3)C51—C52—C53—C55−1.2 (5)
C18—C19—C20—C22−1.7 (4)C54—O15—C53—C52−172.0 (4)
C18—C19—C20—O5179.3 (3)C54—O15—C53—C557.9 (4)
C22—O4—C21—O522.7 (3)C53—O15—C54—O14−13.2 (5)
C20—O5—C21—O4−22.1 (3)C55—O14—C54—O1513.4 (5)
O5—C20—C22—C23179.4 (3)C54—O14—C55—C56170.9 (4)
C19—C20—C22—C230.2 (5)C54—O14—C55—C53−8.3 (4)
O5—C20—C22—O40.8 (4)C52—C53—C55—C560.9 (5)
C19—C20—C22—O4−178.4 (3)O15—C53—C55—C56−179.0 (3)
C21—O4—C22—C23166.9 (3)C52—C53—C55—O14−179.8 (3)
C21—O4—C22—C20−14.6 (3)O15—C53—C55—O140.3 (4)
C20—C22—C23—C241.6 (5)O14—C55—C56—C57−178.3 (3)
O4—C22—C23—C24179.9 (3)C53—C55—C56—C570.8 (5)
C22—C23—C24—C18−1.9 (4)C52—C51—C57—C561.9 (4)
C22—C23—C24—C12173.4 (3)C50—C51—C57—C56−178.0 (3)
C19—C18—C24—C230.5 (4)C52—C51—C57—C45−174.3 (3)
C17—C18—C24—C23−178.7 (3)C50—C51—C57—C455.7 (4)
C19—C18—C24—C12−174.5 (3)C55—C56—C57—C51−2.2 (4)
C17—C18—C24—C126.3 (4)C55—C56—C57—C45174.3 (3)
N2—C12—C24—C23−64.3 (3)N4—C45—C57—C5198.9 (3)
C13—C12—C24—C23171.3 (3)C46—C45—C57—C51−23.9 (4)
N2—C12—C24—C18110.9 (3)N4—C45—C57—C56−77.5 (3)
C13—C12—C24—C18−13.5 (4)C46—C45—C57—C56159.7 (3)
C18—C17—C25—C30148.3 (3)C51—C50—C58—C59−34.1 (4)
C16—C17—C25—C30−90.0 (3)C49—C50—C58—C5990.9 (3)
C18—C17—C25—C26−29.8 (4)C51—C50—C58—C63143.9 (3)
C16—C17—C25—C2691.9 (3)C49—C50—C58—C63−91.2 (3)
C30—C25—C26—C271.5 (4)C63—C58—C59—C601.6 (4)
C17—C25—C26—C27179.6 (3)C50—C58—C59—C60179.5 (3)
C31—O8—C27—C28−175.5 (3)C64—O18—C60—C591.7 (4)
C31—O8—C27—C262.8 (5)C64—O18—C60—C61−176.6 (3)
C25—C26—C27—O8−178.6 (3)C58—C59—C60—O18−178.0 (3)
C25—C26—C27—C28−0.3 (5)C58—C59—C60—C610.3 (4)
C32—O9—C28—C29−93.1 (3)C65—O19—C61—C6275.3 (4)
C32—O9—C28—C2786.4 (4)C65—O19—C61—C60−108.7 (4)
O8—C27—C28—C29176.7 (3)O18—C60—C61—O19−0.1 (4)
C26—C27—C28—C29−1.7 (5)C59—C60—C61—O19−178.6 (3)
O8—C27—C28—O9−2.7 (4)O18—C60—C61—C62175.9 (2)
C26—C27—C28—O9178.8 (3)C59—C60—C61—C62−2.5 (4)
C33—O10—C29—C28164.1 (3)C66—O20—C62—C63−31.8 (4)
C33—O10—C29—C30−14.8 (5)C66—O20—C62—C61149.0 (3)
O9—C28—C29—O103.0 (4)O19—C61—C62—O20−1.9 (4)
C27—C28—C29—O10−176.5 (3)C60—C61—C62—O20−177.9 (3)
O9—C28—C29—C30−178.1 (3)O19—C61—C62—C63178.8 (3)
C27—C28—C29—C302.5 (5)C60—C61—C62—C632.8 (4)
C26—C25—C30—C29−0.8 (5)O20—C62—C63—C58180.0 (3)
C17—C25—C30—C29−178.9 (3)C61—C62—C63—C58−0.8 (4)
O10—C29—C30—C25177.6 (3)C59—C58—C63—C62−1.4 (4)
C28—C29—C30—C25−1.3 (5)C50—C58—C63—C62−179.3 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2197).

References

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