4-Des-oxy-4β-(4-methoxy-carbonyl-1,2,3-triazol-1-yl)podophyllotoxin dichloro-methane solvate.

In the title compound {systematic name: methyl 1-[12-oxo-10-(3,4,5-trimethoxy-phen-yl)-4,6,13-trioxa-tetra-cyclo-[7.7.0.0(3,7).0(11,15)]hexa-deca-1,3(7),8-trien-16-yl]-1H-1,2,3-triazole-4-carboxyl-ate dichloro-methane solvate}, C(26)H(25)N(3)O(9)·CH(2)Cl(2), the tetra-hydro-furan 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 ▶); Yu & Chen (2008 ▶); Van Maanen et al. (1988 ▶). For a review of the structures of azides and triazides, see: Bräse et al. (2005 ▶). For additional background to 1,3-dipolar azide–alkyne cycloaddition reactions, see: Hainsworth et al. (1985 ▶); Huisgen (1963 ▶); Jacobsen et al. (1988 ▶); Lee (2004 ▶).

Experimental

Crystal data

C26H25N3O9·CH2Cl2

M = 608.42

Orthorhombic,

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 ▶) 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 ▶), 2800 Friedel pairs

Flack parameter: 0.04 (4)

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

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

C26H25N3O9·CH2Cl2	Dx = 1.506 Mg m−3
Mr = 608.42	Melting point = 212–213 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9219 reflections
a = 10.377 (2) Å	θ = 1.9–27.9°
b = 12.639 (3) Å	µ = 0.30 mm−1
c = 20.463 (4) Å	T = 113 K
V = 2683.9 (10) Å3	Block, colorless
Z = 4	0.28 × 0.24 × 0.12 mm
F(000) = 1264

Rigaku Saturn CCD area-detector diffractometer	6397 independent reflections
Radiation source: rotating anode	5768 reflections with I > 2σ(I)
confocal	Rint = 0.036
Detector resolution: 7.31 pixels mm-1	θmax = 27.9°, θmin = 1.9°
ω and φ scans	h = −13→13
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −12→16
Tmin = 0.920, Tmax = 0.965	l = −26→26
22515 measured reflections

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

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.

	x	y	z	Uiso*/Ueq
O1	0.81730 (11)	0.46481 (8)	−0.07929 (6)	0.0222 (2)
O2	1.02230 (11)	0.38471 (8)	−0.13992 (5)	0.0200 (2)
O3	1.07335 (11)	0.17818 (9)	−0.13872 (6)	0.0242 (3)
O4	1.03010 (12)	0.07454 (9)	0.18541 (6)	0.0279 (3)
O5	1.04059 (12)	−0.10864 (9)	0.17747 (6)	0.0263 (3)
O6	0.49041 (12)	−0.00212 (9)	−0.11823 (6)	0.0273 (3)
O7	0.50203 (13)	0.17197 (9)	−0.09864 (6)	0.0313 (3)
O8	0.35597 (12)	−0.14406 (9)	0.20717 (6)	0.0254 (3)
O9	0.30253 (11)	−0.31101 (8)	0.17946 (6)	0.0242 (3)
N1	0.60318 (12)	−0.17930 (9)	0.04644 (6)	0.0167 (3)
N2	0.56517 (13)	−0.28046 (10)	0.03289 (7)	0.0234 (3)
N3	0.47699 (14)	−0.30643 (10)	0.07549 (6)	0.0226 (3)
C1	0.78479 (14)	0.18283 (11)	−0.03338 (7)	0.0162 (3)
C2	0.75602 (15)	0.29059 (11)	−0.03655 (7)	0.0176 (3)
H2	0.6835	0.3180	−0.0138	0.021*
C3	0.83415 (15)	0.35759 (11)	−0.07318 (8)	0.0172 (3)
C4	0.93996 (15)	0.31698 (12)	−0.10722 (7)	0.0165 (3)
C5	0.96690 (15)	0.20875 (12)	−0.10457 (7)	0.0175 (3)
C6	0.88965 (15)	0.14181 (12)	−0.06738 (8)	0.0178 (3)
H6	0.9085	0.0683	−0.0652	0.021*
C7	0.72731 (16)	0.51437 (13)	−0.03645 (8)	0.0261 (4)
H7A	0.7549	0.5042	0.0089	0.039*
H7B	0.6419	0.4828	−0.0427	0.039*
H7C	0.7232	0.5902	−0.0462	0.039*
C8	0.98547 (17)	0.40051 (14)	−0.20675 (8)	0.0245 (4)
H8A	0.9016	0.4361	−0.2084	0.037*
H8B	0.9794	0.3319	−0.2288	0.037*
H8C	1.0502	0.4443	−0.2287	0.037*
C9	1.09771 (18)	0.06681 (13)	−0.14314 (9)	0.0279 (4)
H9A	1.0224	0.0314	−0.1620	0.042*
H9B	1.1145	0.0384	−0.0994	0.042*
H9C	1.1729	0.0545	−0.1711	0.042*
C10	0.70229 (15)	0.11348 (11)	0.01110 (7)	0.0165 (3)
H10	0.6540	0.1623	0.0407	0.020*
C11	0.78712 (15)	0.04464 (11)	0.05453 (7)	0.0161 (3)
C12	0.86601 (15)	0.09890 (12)	0.09961 (8)	0.0192 (3)
H12	0.8637	0.1738	0.1029	0.023*
C13	0.94594 (15)	0.03996 (12)	0.13838 (8)	0.0188 (3)
C14	1.09057 (17)	−0.01795 (14)	0.21149 (9)	0.0278 (4)
H14A	1.0721	−0.0239	0.2588	0.033*
H14B	1.1851	−0.0135	0.2056	0.033*
C15	0.95192 (15)	−0.06919 (12)	0.13392 (8)	0.0188 (3)
C16	0.87764 (15)	−0.12393 (12)	0.09064 (8)	0.0181 (3)
H16	0.8828	−0.1988	0.0875	0.022*
C17	0.79280 (14)	−0.06537 (11)	0.05070 (7)	0.0156 (3)
C18	0.70594 (15)	−0.13007 (11)	0.00655 (7)	0.0162 (3)
H18	0.7587	−0.1880	−0.0133	0.019*
C19	0.65391 (15)	−0.06140 (11)	−0.04854 (8)	0.0174 (3)
H19	0.7265	−0.0457	−0.0792	0.021*
C20	0.53937 (17)	−0.09906 (12)	−0.08870 (8)	0.0224 (3)
H20A	0.5667	−0.1503	−0.1226	0.027*
H20B	0.4734	−0.1325	−0.0605	0.027*
C21	0.52869 (16)	0.08367 (13)	−0.08212 (8)	0.0224 (3)
C22	0.60149 (15)	0.04366 (11)	−0.02292 (7)	0.0173 (3)
H22	0.5353	0.0258	0.0108	0.021*
C23	0.53786 (16)	−0.14106 (12)	0.09778 (7)	0.0172 (3)
H23	0.5456	−0.0731	0.1172	0.021*
C24	0.45700 (15)	−0.22220 (12)	0.11611 (8)	0.0169 (3)
C25	0.36761 (15)	−0.22017 (12)	0.17193 (8)	0.0192 (3)
C26	0.21945 (17)	−0.31309 (14)	0.23663 (8)	0.0287 (4)
H26A	0.1500	−0.2613	0.2312	0.043*
H26B	0.2700	−0.2954	0.2756	0.043*
H26C	0.1824	−0.3839	0.2416	0.043*
Cl1	0.26269 (6)	0.39288 (4)	0.23482 (3)	0.05616 (18)
Cl2	0.21387 (5)	0.18814 (4)	0.29584 (2)	0.03992 (13)
C27	0.1834 (2)	0.27027 (14)	0.22719 (10)	0.0343 (4)
H27A	0.2134	0.2342	0.1870	0.041*
H27B	0.0895	0.2823	0.2231	0.041*

	U11	U22	U33	U12	U13	U23
O1	0.0274 (6)	0.0121 (5)	0.0272 (6)	0.0025 (4)	0.0052 (5)	0.0009 (4)
O2	0.0216 (6)	0.0202 (6)	0.0181 (5)	−0.0065 (4)	0.0010 (5)	0.0023 (4)
O3	0.0228 (6)	0.0206 (6)	0.0293 (6)	0.0030 (5)	0.0106 (5)	−0.0002 (5)
O4	0.0315 (7)	0.0217 (6)	0.0305 (7)	−0.0010 (5)	−0.0133 (6)	−0.0014 (5)
O5	0.0284 (6)	0.0208 (6)	0.0297 (7)	0.0024 (5)	−0.0120 (5)	0.0002 (5)
O6	0.0307 (7)	0.0246 (6)	0.0267 (6)	−0.0017 (5)	−0.0094 (5)	0.0035 (5)
O7	0.0314 (7)	0.0243 (6)	0.0381 (7)	0.0046 (5)	−0.0067 (6)	0.0088 (6)
O8	0.0291 (7)	0.0228 (6)	0.0241 (6)	−0.0017 (5)	0.0064 (5)	−0.0022 (5)
O9	0.0249 (6)	0.0238 (6)	0.0239 (6)	−0.0066 (5)	0.0036 (5)	0.0035 (5)
N1	0.0195 (6)	0.0119 (6)	0.0186 (6)	−0.0005 (5)	0.0004 (5)	−0.0004 (5)
N2	0.0275 (8)	0.0157 (7)	0.0269 (8)	−0.0054 (5)	0.0019 (6)	−0.0033 (6)
N3	0.0256 (8)	0.0194 (7)	0.0227 (7)	−0.0059 (6)	0.0025 (6)	−0.0006 (6)
C1	0.0182 (7)	0.0155 (7)	0.0149 (7)	−0.0014 (6)	−0.0009 (6)	−0.0006 (6)
C2	0.0177 (8)	0.0168 (8)	0.0184 (8)	0.0011 (6)	0.0010 (6)	−0.0016 (6)
C3	0.0212 (8)	0.0121 (7)	0.0181 (8)	0.0000 (6)	−0.0037 (6)	0.0006 (6)
C4	0.0175 (8)	0.0178 (7)	0.0141 (7)	−0.0045 (6)	−0.0001 (6)	0.0016 (6)
C5	0.0162 (8)	0.0215 (8)	0.0148 (7)	0.0009 (6)	0.0015 (6)	−0.0031 (6)
C6	0.0195 (8)	0.0156 (7)	0.0184 (8)	0.0008 (6)	−0.0006 (6)	0.0002 (6)
C7	0.0264 (9)	0.0177 (8)	0.0342 (10)	0.0026 (6)	0.0033 (8)	−0.0017 (7)
C8	0.0290 (9)	0.0268 (9)	0.0178 (8)	0.0008 (7)	0.0028 (7)	0.0030 (7)
C9	0.0315 (9)	0.0257 (9)	0.0267 (9)	0.0104 (7)	0.0078 (8)	0.0010 (7)
C10	0.0185 (8)	0.0138 (7)	0.0171 (8)	0.0009 (6)	0.0027 (6)	0.0005 (6)
C11	0.0169 (8)	0.0155 (7)	0.0158 (7)	−0.0005 (6)	0.0042 (6)	0.0007 (5)
C12	0.0212 (8)	0.0157 (8)	0.0206 (8)	−0.0015 (6)	0.0031 (6)	0.0012 (6)
C13	0.0185 (8)	0.0188 (8)	0.0192 (8)	−0.0038 (6)	0.0015 (6)	−0.0020 (6)
C14	0.0287 (9)	0.0268 (9)	0.0278 (9)	0.0036 (7)	−0.0089 (7)	−0.0029 (7)
C15	0.0176 (8)	0.0191 (8)	0.0196 (8)	0.0028 (6)	0.0007 (6)	0.0017 (6)
C16	0.0192 (8)	0.0152 (8)	0.0199 (8)	0.0012 (6)	0.0024 (6)	0.0004 (6)
C17	0.0155 (7)	0.0151 (7)	0.0162 (7)	0.0005 (5)	0.0035 (6)	0.0003 (5)
C18	0.0171 (8)	0.0153 (7)	0.0162 (7)	−0.0009 (6)	0.0036 (6)	−0.0010 (6)
C19	0.0195 (8)	0.0160 (8)	0.0169 (8)	−0.0006 (6)	0.0023 (6)	−0.0010 (6)
C20	0.0262 (9)	0.0195 (8)	0.0214 (8)	−0.0008 (7)	−0.0025 (7)	0.0023 (6)
C21	0.0186 (8)	0.0255 (9)	0.0231 (8)	−0.0017 (6)	0.0006 (7)	0.0041 (7)
C22	0.0172 (7)	0.0152 (8)	0.0194 (8)	0.0004 (6)	0.0037 (6)	0.0026 (6)
C23	0.0204 (8)	0.0164 (7)	0.0148 (8)	0.0011 (6)	0.0003 (6)	−0.0007 (6)
C24	0.0184 (8)	0.0156 (7)	0.0166 (8)	−0.0006 (6)	−0.0026 (6)	0.0014 (6)
C25	0.0169 (8)	0.0215 (8)	0.0192 (8)	−0.0009 (6)	−0.0013 (7)	0.0053 (6)
C26	0.0261 (9)	0.0301 (9)	0.0300 (9)	−0.0017 (8)	0.0072 (8)	0.0105 (8)
Cl1	0.0722 (4)	0.0437 (3)	0.0526 (3)	−0.0320 (3)	0.0287 (3)	−0.0187 (3)
Cl2	0.0490 (3)	0.0366 (3)	0.0342 (3)	0.0004 (2)	0.0064 (2)	−0.0110 (2)
C27	0.0350 (11)	0.0262 (9)	0.0417 (11)	−0.0044 (8)	0.0050 (9)	−0.0084 (8)

O1—C3	1.3722 (18)	C9—H9A	0.9800
O1—C7	1.4258 (19)	C9—H9B	0.9800
O2—C4	1.3823 (17)	C9—H9C	0.9800
O2—C8	1.4339 (19)	C10—C11	1.524 (2)
O3—C5	1.3631 (19)	C10—C22	1.535 (2)
O3—C9	1.433 (2)	C10—H10	1.0000
O4—C13	1.3710 (19)	C11—C17	1.394 (2)
O4—C14	1.430 (2)	C11—C12	1.411 (2)
O5—C15	1.3747 (19)	C12—C13	1.368 (2)
O5—C14	1.438 (2)	C12—H12	0.9500
O6—C21	1.371 (2)	C13—C15	1.384 (2)
O6—C20	1.4575 (19)	C14—H14A	0.9900
O7—C21	1.1985 (19)	C14—H14B	0.9900
O8—C25	1.2084 (19)	C15—C16	1.363 (2)
O9—C25	1.3409 (19)	C16—C17	1.411 (2)
O9—C26	1.454 (2)	C16—H16	0.9500
N1—C23	1.340 (2)	C17—C18	1.516 (2)
N1—N2	1.3664 (18)	C18—C19	1.522 (2)
N1—C18	1.4800 (19)	C18—H18	1.0000
N2—N3	1.3057 (19)	C19—C20	1.521 (2)
N3—C24	1.367 (2)	C19—C22	1.528 (2)
C1—C6	1.392 (2)	C19—H19	1.0000
C1—C2	1.396 (2)	C20—H20A	0.9900
C1—C10	1.526 (2)	C20—H20B	0.9900
C2—C3	1.392 (2)	C21—C22	1.515 (2)
C2—H2	0.9500	C22—H22	1.0000
C3—C4	1.398 (2)	C23—C24	1.377 (2)
C4—C5	1.397 (2)	C23—H23	0.9500
C5—C6	1.392 (2)	C24—C25	1.472 (2)
C6—H6	0.9500	C26—H26A	0.9800
C7—H7A	0.9800	C26—H26B	0.9800
C7—H7B	0.9800	C26—H26C	0.9800
C7—H7C	0.9800	Cl1—C27	1.7613 (19)
C8—H8A	0.9800	Cl2—C27	1.775 (2)
C8—H8B	0.9800	C27—H27A	0.9900
C8—H8C	0.9800	C27—H27B	0.9900
C3—O1—C7	117.47 (12)	O4—C14—O5	108.23 (13)
C4—O2—C8	112.53 (12)	O4—C14—H14A	110.1
C5—O3—C9	116.98 (12)	O5—C14—H14A	110.1
C13—O4—C14	106.31 (12)	O4—C14—H14B	110.1
C15—O5—C14	105.43 (12)	O5—C14—H14B	110.1
C21—O6—C20	109.90 (12)	H14A—C14—H14B	108.4
C25—O9—C26	114.00 (12)	C16—C15—O5	128.01 (14)
C23—N1—N2	110.51 (12)	C16—C15—C13	121.57 (15)
C23—N1—C18	130.16 (12)	O5—C15—C13	110.42 (14)
N2—N1—C18	119.31 (12)	C15—C16—C17	117.59 (14)
N3—N2—N1	107.58 (12)	C15—C16—H16	121.2
N2—N3—C24	108.46 (12)	C17—C16—H16	121.2
C6—C1—C2	120.50 (14)	C11—C17—C16	121.13 (14)
C6—C1—C10	121.51 (13)	C11—C17—C18	123.14 (14)
C2—C1—C10	117.91 (13)	C16—C17—C18	115.68 (13)
C3—C2—C1	119.62 (14)	N1—C18—C17	109.06 (12)
C3—C2—H2	120.2	N1—C18—C19	113.12 (13)
C1—C2—H2	120.2	C17—C18—C19	110.17 (12)
O1—C3—C2	125.16 (14)	N1—C18—H18	108.1
O1—C3—C4	114.67 (14)	C17—C18—H18	108.1
C2—C3—C4	120.17 (14)	C19—C18—H18	108.1
O2—C4—C5	120.10 (14)	C20—C19—C18	119.93 (12)
O2—C4—C3	119.95 (13)	C20—C19—C22	100.32 (12)
C5—C4—C3	119.81 (13)	C18—C19—C22	111.58 (13)
O3—C5—C6	125.09 (14)	C20—C19—H19	108.1
O3—C5—C4	114.81 (13)	C18—C19—H19	108.1
C6—C5—C4	120.07 (14)	C22—C19—H19	108.1
C1—C6—C5	119.82 (14)	O6—C20—C19	103.49 (12)
C1—C6—H6	120.1	O6—C20—H20A	111.1
C5—C6—H6	120.1	C19—C20—H20A	111.1
O1—C7—H7A	109.5	O6—C20—H20B	111.1
O1—C7—H7B	109.5	C19—C20—H20B	111.1
H7A—C7—H7B	109.5	H20A—C20—H20B	109.0
O1—C7—H7C	109.5	O7—C21—O6	121.17 (15)
H7A—C7—H7C	109.5	O7—C21—C22	130.67 (15)
H7B—C7—H7C	109.5	O6—C21—C22	108.15 (13)
O2—C8—H8A	109.5	C21—C22—C19	101.14 (13)
O2—C8—H8B	109.5	C21—C22—C10	120.70 (12)
H8A—C8—H8B	109.5	C19—C22—C10	114.36 (13)
O2—C8—H8C	109.5	C21—C22—H22	106.6
H8A—C8—H8C	109.5	C19—C22—H22	106.6
H8B—C8—H8C	109.5	C10—C22—H22	106.6
O3—C9—H9A	109.5	N1—C23—C24	104.66 (13)
O3—C9—H9B	109.5	N1—C23—H23	127.7
H9A—C9—H9B	109.5	C24—C23—H23	127.7
O3—C9—H9C	109.5	N3—C24—C23	108.78 (14)
H9A—C9—H9C	109.5	N3—C24—C25	125.55 (14)
H9B—C9—H9C	109.5	C23—C24—C25	125.63 (14)
C11—C10—C1	110.59 (12)	O8—C25—O9	124.24 (15)
C11—C10—C22	109.26 (12)	O8—C25—C24	122.69 (14)
C1—C10—C22	116.22 (12)	O9—C25—C24	113.07 (14)
C11—C10—H10	106.8	O9—C26—H26A	109.5
C1—C10—H10	106.8	O9—C26—H26B	109.5
C22—C10—H10	106.8	H26A—C26—H26B	109.5
C17—C11—C12	119.80 (14)	O9—C26—H26C	109.5
C17—C11—C10	124.14 (14)	H26A—C26—H26C	109.5
C12—C11—C10	116.03 (12)	H26B—C26—H26C	109.5
C13—C12—C11	117.78 (14)	Cl1—C27—Cl2	111.18 (11)
C13—C12—H12	121.1	Cl1—C27—H27A	109.4
C11—C12—H12	121.1	Cl2—C27—H27A	109.4
C12—C13—O4	128.28 (14)	Cl1—C27—H27B	109.4
C12—C13—C15	122.11 (15)	Cl2—C27—H27B	109.4
O4—C13—C15	109.60 (14)	H27A—C27—H27B	108.0
C23—N1—N2—N3	−0.34 (17)	C13—C15—C16—C17	−0.7 (2)
C18—N1—N2—N3	178.32 (12)	C12—C11—C17—C16	−0.9 (2)
N1—N2—N3—C24	0.55 (17)	C10—C11—C17—C16	177.31 (13)
C6—C1—C2—C3	−1.0 (2)	C12—C11—C17—C18	176.30 (13)
C10—C1—C2—C3	175.82 (14)	C10—C11—C17—C18	−5.5 (2)
C7—O1—C3—C2	11.4 (2)	C15—C16—C17—C11	1.2 (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—C17	37.7 (2)
C1—C2—C3—C4	0.7 (2)	N2—N1—C18—C17	−140.67 (13)
C8—O2—C4—C5	92.48 (17)	C23—N1—C18—C19	−85.29 (18)
C8—O2—C4—C3	−91.68 (17)	N2—N1—C18—C19	96.36 (15)
O1—C3—C4—O2	4.1 (2)	C11—C17—C18—N1	−103.10 (16)
C2—C3—C4—O2	−175.64 (14)	C16—C17—C18—N1	74.20 (16)
O1—C3—C4—C5	179.91 (13)	C11—C17—C18—C19	21.6 (2)
C2—C3—C4—C5	0.2 (2)	C16—C17—C18—C19	−161.08 (13)
C9—O3—C5—C6	8.2 (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—C22	74.75 (15)
C3—C4—C5—O3	−179.03 (14)	C17—C18—C19—C22	−47.60 (17)
O2—C4—C5—C6	174.94 (14)	C21—O6—C20—C19	−22.57 (16)
C3—C4—C5—C6	−0.9 (2)	C18—C19—C20—O6	160.39 (13)
C2—C1—C6—C5	0.3 (2)	C22—C19—C20—O6	37.97 (14)
C10—C1—C6—C5	−176.39 (14)	C20—O6—C21—O7	177.91 (16)
O3—C5—C6—C1	178.54 (14)	C20—O6—C21—C22	−3.11 (17)
C4—C5—C6—C1	0.6 (2)	O7—C21—C22—C19	−153.98 (19)
C6—C1—C10—C11	45.76 (19)	O6—C21—C22—C19	27.17 (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—C10	154.47 (14)
C2—C1—C10—C22	103.66 (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—C17	14.9 (2)	C20—C19—C22—C10	−170.17 (13)
C1—C10—C11—C12	63.98 (17)	C18—C19—C22—C10	61.71 (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—C19	83.85 (16)
C11—C12—C13—C15	0.7 (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—O5	0.88 (18)	N2—N3—C24—C25	−178.25 (14)
C15—O5—C14—O4	−1.12 (18)	N1—C23—C24—N3	0.34 (17)
C14—O5—C15—C16	−179.58 (17)	N1—C23—C24—C25	178.03 (14)
C14—O5—C15—C13	0.96 (18)	C26—O9—C25—O8	−3.0 (2)
C12—C13—C15—C16	−0.3 (3)	C26—O9—C25—C24	176.46 (13)
O4—C13—C15—C16	−179.94 (14)	N3—C24—C25—O8	178.28 (16)
C12—C13—C15—O5	179.20 (14)	C23—C24—C25—O8	1.0 (3)
O4—C13—C15—O5	−0.43 (19)	N3—C24—C25—O9	−1.2 (2)
O5—C15—C16—C17	179.92 (15)	C23—C24—C25—O9	−178.50 (15)