(3R*)-Methyl 3-[(2S*)-4,6-dimethoxy-2-(4-methoxyphenyl)-3-oxo-2,3-dihydro-1-benzofuran-2-yl]-2-methoxycarbonyl-3-phenylpropionate.

The title compound, C(29)H(28)O(9), was isolated from the reaction of 4,6-dimeth-oxy-2-(4-methoxy-phen-yl)-3-benzofuran and α-methoxy-carbonyl-cinnaminate. The two aromatic rings form a dihedral angle of 22.7 (1)°. One methoxy-carbonyl group is disordered between two orientations in a 0.612 (4):0.388 (4) ratio. The crystal structure exhibits no significantly short inter-molecular contacts.

Related literature

The title compound is a key inter­mediate in the synthesis of rocaglamide, see: Kraus & Sy (1989 ▶); Li et al. (2008 ▶). For the biological activity of rocaglamide derivatives, see: Zhu et al. (2007 ▶).

Experimental

Crystal data

C29H28O9

M = 520.51

Triclinic,

a = 6.901 (5) Å

b = 10.478 (5) Å

c = 18.467 (5) Å

α = 79.838 (5)°

β = 86.976 (5)°

γ = 77.097 (5)°

V = 1281.1 (12) Å3

Z = 2

Cu Kα radiation

μ = 0.84 mm−1

T = 295 K

0.40 × 0.36 × 0.34 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer

Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 ▶). T min = 0.731, T max = 0.764

24595 measured reflections

4811 independent reflections

4581 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.093

S = 1.01

4811 reflections

378 parameters

9 restraints

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.45 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809042196/cv2618sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042196/cv2618Isup2.hkl

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

C29H28O9	Z = 2
Mr = 520.51	F(000) = 548
Triclinic, P1	Dx = 1.349 Mg m−3
a = 6.901 (5) Å	Cu Kα radiation, λ = 1.54184 Å
b = 10.478 (5) Å	Cell parameters from 21851 reflections
c = 18.467 (5) Å	θ = 2.4–72.1°
α = 79.838 (5)°	µ = 0.84 mm−1
β = 86.976 (5)°	T = 295 K
γ = 77.097 (5)°	Block, colourless
V = 1281.1 (12) Å3	0.40 × 0.36 × 0.34 mm

Oxford Diffraction Gemini S Ultra diffractometer	4811 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	4581 reflections with I > 2σ(I)
mirror	Rint = 0.018
Detector resolution: 15.9149 pixels mm-1	θmax = 70.1°, θmin = 2.4°
ω scans	h = −8→6
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009).	k = −12→12
Tmin = 0.731, Tmax = 0.764	l = −22→22
24595 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)] = 0.042	H-atom parameters constrained
wR(F2) = 0.093	w = 1/[σ2(Fo2) + (0.0289P)2 + 0.6245P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
4811 reflections	Δρmax = 0.41 e Å−3
378 parameters	Δρmin = −0.45 e Å−3
9 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0365 (14)

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	Occ. (<1)
O1	0.72974 (16)	−0.00047 (10)	0.17466 (6)	0.0477 (3)
O2	0.11720 (18)	0.08988 (12)	0.05005 (7)	0.0560 (3)
O3	0.74032 (15)	0.21665 (10)	0.26672 (6)	0.0441 (3)
O4	0.23465 (13)	0.35531 (9)	0.22326 (5)	0.0339 (2)
O5	0.1979 (2)	0.09372 (13)	0.55766 (6)	0.0616 (3)
O8	0.47464 (18)	0.74181 (12)	0.28233 (9)	0.0681 (4)
O9	0.14431 (16)	0.81607 (10)	0.27886 (7)	0.0517 (3)
C1	0.2267 (2)	0.12553 (15)	0.09905 (8)	0.0406 (3)
C2	0.4180 (2)	0.04509 (15)	0.11022 (8)	0.0445 (4)
H2	0.4594	−0.0263	0.0853	0.053*
C3	0.5450 (2)	0.07168 (14)	0.15815 (8)	0.0374 (3)
C4	0.4790 (2)	0.18239 (13)	0.19409 (7)	0.0338 (3)
C5	0.2860 (2)	0.25550 (12)	0.18279 (7)	0.0320 (3)
C6	0.1540 (2)	0.23139 (14)	0.13594 (7)	0.0363 (3)
H6	0.0254	0.2825	0.1295	0.044*
C7	0.3966 (2)	0.34343 (13)	0.27287 (7)	0.0324 (3)
C8	0.5705 (2)	0.24013 (13)	0.24547 (7)	0.0334 (3)
C9	0.3410 (2)	0.27976 (13)	0.34983 (7)	0.0341 (3)
C10	0.4720 (2)	0.26054 (15)	0.40736 (8)	0.0424 (3)
H10	0.5905	0.2894	0.3987	0.051*
C11	0.4297 (2)	0.19920 (16)	0.47741 (8)	0.0469 (4)
H11	0.5184	0.1883	0.5153	0.056*
C12	0.2553 (2)	0.15417 (15)	0.49079 (8)	0.0444 (4)
C13	0.1257 (2)	0.16977 (16)	0.43329 (9)	0.0460 (4)
H13	0.0095	0.1380	0.4416	0.055*
C14	0.1678 (2)	0.23218 (14)	0.36369 (8)	0.0392 (3)
H14	0.0793	0.2424	0.3257	0.047*
C15	0.3217 (3)	0.0827 (2)	0.61877 (10)	0.0685 (5)
H15B	0.4527	0.0335	0.6091	0.103*
H15C	0.2670	0.0374	0.6620	0.103*
H15A	0.3289	0.1699	0.6263	0.103*
C16	0.4442 (2)	0.48256 (13)	0.26704 (7)	0.0334 (3)
H16	0.5424	0.4762	0.3047	0.040*
C17	0.5380 (2)	0.52433 (13)	0.19253 (8)	0.0347 (3)
C18	0.4260 (2)	0.57228 (18)	0.12944 (9)	0.0498 (4)
H18	0.2887	0.5813	0.1324	0.060*
C19	0.5154 (3)	0.6070 (2)	0.06191 (10)	0.0610 (5)
H19	0.4378	0.6389	0.0202	0.073*
C20	0.7178 (3)	0.59466 (18)	0.05638 (10)	0.0566 (4)
H20	0.7779	0.6175	0.0111	0.068*
C21	0.8301 (2)	0.54818 (16)	0.11845 (10)	0.0514 (4)
H21	0.9672	0.5397	0.1151	0.062*
C22	0.7418 (2)	0.51363 (14)	0.18602 (9)	0.0423 (3)
H22	0.8203	0.4828	0.2276	0.051*
C23	0.2594 (2)	0.58820 (13)	0.28276 (8)	0.0362 (3)
H23	0.1610	0.5978	0.2447	0.043*
C24	0.1603 (2)	0.56062 (15)	0.35796 (8)	0.0455 (4)
C26	0.3135 (2)	0.72205 (13)	0.28050 (8)	0.0408 (3)
C27	0.1644 (3)	0.94722 (15)	0.28982 (12)	0.0638 (5)
H27B	0.0520	1.0130	0.2692	0.096*
H27C	0.2841	0.9664	0.2659	0.096*
H27A	0.1703	0.9484	0.3415	0.096*
C28	0.7892 (3)	−0.12487 (18)	0.14867 (11)	0.0616 (5)
H28B	0.7877	−0.1093	0.0959	0.092*
H28A	0.6986	−0.1806	0.1675	0.092*
H28C	0.9210	−0.1679	0.1652	0.092*
C29	−0.0736 (3)	0.17228 (18)	0.03147 (10)	0.0542 (4)
H29C	−0.1343	0.1365	−0.0037	0.081*
H29B	−0.0592	0.2603	0.0106	0.081*
H29A	−0.1558	0.1755	0.0750	0.081*
O6A	0.2258 (6)	0.5551 (6)	0.41638 (11)	0.0610 (9)	0.612 (4)
O7A	−0.0279 (4)	0.5512 (5)	0.34725 (13)	0.0462 (7)	0.612 (4)
C25A	−0.1494 (4)	0.5308 (3)	0.41401 (13)	0.0527 (8)	0.612 (4)
H25A	−0.2861	0.5443	0.4008	0.079*	0.612 (4)
H25B	−0.1368	0.5929	0.4450	0.079*	0.612 (4)
H25C	−0.1050	0.4418	0.4399	0.079*	0.612 (4)
O6B	0.0009 (7)	0.5422 (10)	0.3754 (4)	0.097 (3)	0.388 (4)
O7B	0.2974 (7)	0.5644 (8)	0.40674 (19)	0.074 (2)	0.388 (4)
C25B	0.2580 (11)	0.5464 (7)	0.4862 (2)	0.090 (2)	0.388 (4)
H25D	0.3803	0.5331	0.5117	0.135*	0.388 (4)
H25E	0.2003	0.4702	0.5007	0.135*	0.388 (4)
H25F	0.1674	0.6239	0.4981	0.135*	0.388 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0465 (6)	0.0393 (6)	0.0547 (6)	0.0048 (5)	−0.0024 (5)	−0.0187 (5)
O2	0.0601 (7)	0.0565 (7)	0.0579 (7)	−0.0070 (6)	−0.0148 (6)	−0.0299 (6)
O3	0.0363 (6)	0.0397 (6)	0.0555 (6)	−0.0030 (4)	−0.0079 (5)	−0.0104 (5)
O4	0.0358 (5)	0.0298 (5)	0.0365 (5)	−0.0017 (4)	−0.0062 (4)	−0.0120 (4)
O5	0.0730 (8)	0.0697 (8)	0.0418 (6)	−0.0249 (7)	0.0023 (6)	0.0023 (6)
O8	0.0491 (7)	0.0482 (7)	0.1165 (12)	−0.0139 (6)	−0.0003 (7)	−0.0354 (7)
O9	0.0498 (6)	0.0290 (5)	0.0748 (8)	−0.0026 (4)	−0.0009 (5)	−0.0125 (5)
C1	0.0502 (9)	0.0392 (8)	0.0360 (7)	−0.0118 (6)	−0.0038 (6)	−0.0121 (6)
C2	0.0530 (9)	0.0384 (8)	0.0438 (8)	−0.0044 (7)	0.0009 (7)	−0.0193 (6)
C3	0.0410 (8)	0.0316 (7)	0.0379 (7)	−0.0031 (6)	0.0028 (6)	−0.0089 (6)
C4	0.0379 (7)	0.0294 (7)	0.0338 (7)	−0.0055 (5)	0.0006 (5)	−0.0070 (5)
C5	0.0396 (7)	0.0262 (6)	0.0302 (6)	−0.0063 (5)	0.0010 (5)	−0.0065 (5)
C6	0.0398 (7)	0.0338 (7)	0.0352 (7)	−0.0058 (6)	−0.0031 (6)	−0.0081 (6)
C7	0.0344 (7)	0.0290 (6)	0.0343 (7)	−0.0043 (5)	−0.0058 (5)	−0.0083 (5)
C8	0.0366 (7)	0.0270 (6)	0.0352 (7)	−0.0048 (5)	−0.0016 (5)	−0.0039 (5)
C9	0.0398 (7)	0.0267 (6)	0.0359 (7)	−0.0045 (5)	−0.0025 (6)	−0.0083 (5)
C10	0.0442 (8)	0.0438 (8)	0.0408 (8)	−0.0132 (7)	−0.0055 (6)	−0.0057 (6)
C11	0.0538 (9)	0.0487 (9)	0.0382 (8)	−0.0113 (7)	−0.0093 (7)	−0.0047 (7)
C12	0.0558 (9)	0.0377 (8)	0.0383 (8)	−0.0091 (7)	0.0024 (7)	−0.0052 (6)
C13	0.0468 (9)	0.0450 (8)	0.0486 (9)	−0.0160 (7)	0.0019 (7)	−0.0075 (7)
C14	0.0419 (8)	0.0360 (7)	0.0411 (8)	−0.0088 (6)	−0.0047 (6)	−0.0091 (6)
C15	0.0890 (15)	0.0740 (13)	0.0387 (9)	−0.0189 (11)	−0.0037 (9)	0.0023 (8)
C16	0.0363 (7)	0.0289 (6)	0.0356 (7)	−0.0054 (5)	−0.0043 (5)	−0.0083 (5)
C17	0.0377 (7)	0.0272 (6)	0.0400 (7)	−0.0062 (5)	−0.0014 (6)	−0.0083 (5)
C18	0.0398 (8)	0.0637 (10)	0.0437 (8)	−0.0103 (7)	−0.0041 (7)	−0.0032 (7)
C19	0.0608 (11)	0.0768 (13)	0.0413 (9)	−0.0150 (9)	−0.0057 (8)	0.0025 (8)
C20	0.0624 (11)	0.0554 (10)	0.0505 (10)	−0.0165 (8)	0.0127 (8)	−0.0040 (8)
C21	0.0413 (8)	0.0438 (9)	0.0672 (11)	−0.0104 (7)	0.0096 (8)	−0.0061 (8)
C22	0.0389 (8)	0.0344 (7)	0.0522 (9)	−0.0062 (6)	−0.0041 (6)	−0.0046 (6)
C23	0.0401 (8)	0.0305 (7)	0.0387 (7)	−0.0058 (6)	−0.0008 (6)	−0.0103 (6)
C24	0.0602 (10)	0.0313 (7)	0.0444 (9)	−0.0045 (7)	0.0049 (8)	−0.0133 (6)
C26	0.0456 (9)	0.0332 (7)	0.0448 (8)	−0.0066 (6)	−0.0005 (6)	−0.0121 (6)
C27	0.0717 (12)	0.0285 (8)	0.0913 (14)	−0.0093 (8)	0.0114 (10)	−0.0159 (8)
C28	0.0641 (11)	0.0448 (9)	0.0710 (12)	0.0118 (8)	−0.0022 (9)	−0.0268 (9)
C29	0.0510 (10)	0.0614 (11)	0.0568 (10)	−0.0158 (8)	−0.0098 (8)	−0.0207 (8)
O6A	0.074 (2)	0.077 (2)	0.0306 (14)	−0.0115 (17)	0.0055 (14)	−0.0125 (15)
O7A	0.0501 (14)	0.0492 (15)	0.0386 (13)	−0.0111 (9)	0.0131 (10)	−0.0091 (13)
C25A	0.0483 (16)	0.0634 (18)	0.0461 (15)	−0.0120 (13)	0.0125 (12)	−0.0130 (13)
O6B	0.106 (5)	0.065 (3)	0.106 (5)	−0.016 (4)	0.078 (4)	−0.006 (5)
O7B	0.129 (6)	0.050 (2)	0.039 (2)	−0.013 (4)	0.047 (3)	−0.0138 (16)
C25B	0.127 (6)	0.094 (5)	0.057 (3)	−0.035 (4)	0.029 (3)	−0.029 (3)

O1—C3	1.3485 (19)	C16—C23	1.543 (2)
O1—C28	1.4349 (19)	C16—H16	0.9800
O2—C1	1.3589 (18)	C17—C22	1.386 (2)
O2—C29	1.426 (2)	C17—C18	1.387 (2)
O3—C8	1.2141 (18)	C18—C19	1.388 (2)
O4—C5	1.3638 (16)	C18—H18	0.9300
O4—C7	1.4524 (16)	C19—C20	1.374 (3)
O5—C12	1.3665 (19)	C19—H19	0.9300
O5—C15	1.424 (2)	C20—C21	1.371 (3)
O8—C26	1.1788 (18)	C20—H20	0.9300
O9—C26	1.3470 (18)	C21—C22	1.385 (2)
O9—C27	1.4610 (17)	C21—H21	0.9300
C1—C6	1.389 (2)	C22—H22	0.9300
C1—C2	1.402 (2)	C23—C26	1.523 (2)
C2—C3	1.381 (2)	C23—C24	1.525 (2)
C2—H2	0.9300	C23—H23	0.9800
C3—C4	1.4133 (19)	C24—O6B	1.178 (2)
C4—C5	1.386 (2)	C24—O6A	1.1786 (18)
C4—C8	1.4497 (19)	C24—O7B	1.3519 (19)
C5—C6	1.380 (2)	C24—O7A	1.352 (2)
C6—H6	0.9300	C27—H27B	0.9600
C7—C9	1.5280 (19)	C27—H27C	0.9600
C7—C16	1.5491 (19)	C27—H27A	0.9600
C7—C8	1.5545 (19)	C28—H28B	0.9600
C9—C14	1.389 (2)	C28—H28A	0.9600
C9—C10	1.390 (2)	C28—H28C	0.9600
C10—C11	1.387 (2)	C29—H29C	0.9600
C10—H10	0.9300	C29—H29B	0.9600
C11—C12	1.383 (2)	C29—H29A	0.9600
C11—H11	0.9300	O7A—C25A	1.4652 (18)
C12—C13	1.389 (2)	C25A—H25A	0.9600
C13—C14	1.383 (2)	C25A—H25B	0.9600
C13—H13	0.9300	C25A—H25C	0.9600
C14—H14	0.9300	O7B—C25B	1.4642 (19)
C15—H15B	0.9600	C25B—H25D	0.9600
C15—H15C	0.9600	C25B—H25E	0.9600
C15—H15A	0.9600	C25B—H25F	0.9600
C16—C17	1.5243 (19)
C3—O1—C28	117.37 (13)	C22—C17—C16	120.09 (13)
C1—O2—C29	117.97 (13)	C18—C17—C16	122.13 (13)
C5—O4—C7	107.90 (10)	C17—C18—C19	121.03 (16)
C12—O5—C15	117.50 (15)	C17—C18—H18	119.5
C26—O9—C27	116.34 (13)	C19—C18—H18	119.5
O2—C1—C6	122.80 (14)	C20—C19—C18	120.39 (16)
O2—C1—C2	114.41 (13)	C20—C19—H19	119.8
C6—C1—C2	122.78 (13)	C18—C19—H19	119.8
C3—C2—C1	120.13 (13)	C21—C20—C19	119.14 (16)
C3—C2—H2	119.9	C21—C20—H20	120.4
C1—C2—H2	119.9	C19—C20—H20	120.4
O1—C3—C2	125.39 (13)	C20—C21—C22	120.77 (16)
O1—C3—C4	116.06 (13)	C20—C21—H21	119.6
C2—C3—C4	118.54 (13)	C22—C21—H21	119.6
C5—C4—C3	118.67 (13)	C21—C22—C17	120.88 (15)
C5—C4—C8	107.82 (12)	C21—C22—H22	119.6
C3—C4—C8	133.49 (13)	C17—C22—H22	119.6
O4—C5—C6	121.85 (12)	C26—C23—C24	104.52 (11)
O4—C5—C4	113.69 (11)	C26—C23—C16	110.65 (12)
C6—C5—C4	124.46 (13)	C24—C23—C16	115.72 (12)
C5—C6—C1	115.31 (13)	C26—C23—H23	108.6
C5—C6—H6	122.3	C24—C23—H23	108.6
C1—C6—H6	122.3	C16—C23—H23	108.6
O4—C7—C9	109.10 (11)	O6B—C24—O6A	99.9 (4)
O4—C7—C16	107.85 (10)	O6B—C24—O7B	123.3 (4)
C9—C7—C16	115.55 (11)	O6A—C24—O7B	23.4 (3)
O4—C7—C8	104.70 (10)	O6B—C24—O7A	23.9 (4)
C9—C7—C8	106.01 (11)	O6A—C24—O7A	123.6 (2)
C16—C7—C8	113.05 (12)	O7B—C24—O7A	147.0 (3)
O3—C8—C4	131.22 (13)	O6B—C24—C23	131.9 (4)
O3—C8—C7	124.37 (12)	O6A—C24—C23	128.2 (2)
C4—C8—C7	104.38 (12)	O7B—C24—C23	104.8 (2)
C14—C9—C10	118.20 (13)	O7A—C24—C23	108.04 (14)
C14—C9—C7	122.03 (12)	O8—C26—O9	124.70 (14)
C10—C9—C7	119.65 (13)	O8—C26—C23	126.77 (13)
C11—C10—C9	121.33 (15)	O9—C26—C23	108.48 (12)
C11—C10—H10	119.3	O9—C27—H27B	109.5
C9—C10—H10	119.3	O9—C27—H27C	109.5
C12—C11—C10	119.91 (14)	H27B—C27—H27C	109.5
C12—C11—H11	120.0	O9—C27—H27A	109.5
C10—C11—H11	120.0	H27B—C27—H27A	109.5
O5—C12—C11	124.79 (15)	H27C—C27—H27A	109.5
O5—C12—C13	115.96 (15)	O1—C28—H28B	109.5
C11—C12—C13	119.25 (14)	O1—C28—H28A	109.5
C14—C13—C12	120.55 (15)	H28B—C28—H28A	109.5
C14—C13—H13	119.7	O1—C28—H28C	109.5
C12—C13—H13	119.7	H28B—C28—H28C	109.5
C13—C14—C9	120.73 (14)	H28A—C28—H28C	109.5
C13—C14—H14	119.6	O2—C29—H29C	109.5
C9—C14—H14	119.6	O2—C29—H29B	109.5
O5—C15—H15B	109.5	H29C—C29—H29B	109.5
O5—C15—H15C	109.5	O2—C29—H29A	109.5
H15B—C15—H15C	109.5	H29C—C29—H29A	109.5
O5—C15—H15A	109.5	H29B—C29—H29A	109.5
H15B—C15—H15A	109.5	C24—O7A—C25A	115.6 (2)
H15C—C15—H15A	109.5	C24—O7B—C25B	122.2 (4)
C17—C16—C23	111.16 (11)	O7B—C25B—H25D	109.5
C17—C16—C7	111.15 (11)	O7B—C25B—H25E	109.5
C23—C16—C7	111.99 (12)	H25D—C25B—H25E	109.5
C17—C16—H16	107.4	O7B—C25B—H25F	109.5
C23—C16—H16	107.4	H25D—C25B—H25F	109.5
C7—C16—H16	107.4	H25E—C25B—H25F	109.5
C22—C17—C18	117.78 (14)
C29—O2—C1—C6	5.6 (2)	C11—C12—C13—C14	−1.4 (2)
C29—O2—C1—C2	−175.50 (14)	C12—C13—C14—C9	0.4 (2)
O2—C1—C2—C3	179.32 (14)	C10—C9—C14—C13	1.3 (2)
C6—C1—C2—C3	−1.7 (2)	C7—C9—C14—C13	177.15 (13)
C28—O1—C3—C2	−9.3 (2)	O4—C7—C16—C17	−69.31 (14)
C28—O1—C3—C4	170.16 (14)	C9—C7—C16—C17	168.34 (11)
C1—C2—C3—O1	178.22 (14)	C8—C7—C16—C17	45.95 (15)
C1—C2—C3—C4	−1.2 (2)	O4—C7—C16—C23	55.69 (14)
O1—C3—C4—C5	−176.09 (12)	C9—C7—C16—C23	−66.66 (15)
C2—C3—C4—C5	3.4 (2)	C8—C7—C16—C23	170.95 (11)
O1—C3—C4—C8	1.8 (2)	C23—C16—C17—C22	133.41 (13)
C2—C3—C4—C8	−178.72 (15)	C7—C16—C17—C22	−101.13 (14)
C7—O4—C5—C6	173.08 (12)	C23—C16—C17—C18	−47.31 (18)
C7—O4—C5—C4	−6.36 (15)	C7—C16—C17—C18	78.15 (17)
C3—C4—C5—O4	176.52 (12)	C22—C17—C18—C19	0.7 (2)
C8—C4—C5—O4	−1.89 (16)	C16—C17—C18—C19	−178.61 (15)
C3—C4—C5—C6	−2.9 (2)	C17—C18—C19—C20	−0.1 (3)
C8—C4—C5—C6	178.68 (13)	C18—C19—C20—C21	−0.3 (3)
O4—C5—C6—C1	−179.29 (12)	C19—C20—C21—C22	0.1 (3)
C4—C5—C6—C1	0.1 (2)	C20—C21—C22—C17	0.4 (2)
O2—C1—C6—C5	−178.88 (13)	C18—C17—C22—C21	−0.8 (2)
C2—C1—C6—C5	2.3 (2)	C16—C17—C22—C21	178.48 (13)
C5—O4—C7—C9	−101.91 (12)	C17—C16—C23—C26	−57.94 (15)
C5—O4—C7—C16	131.87 (11)	C7—C16—C23—C26	177.07 (11)
C5—O4—C7—C8	11.22 (13)	C17—C16—C23—C24	−176.55 (11)
C5—C4—C8—O3	−173.21 (14)	C7—C16—C23—C24	58.46 (15)
C3—C4—C8—O3	8.7 (3)	C26—C23—C24—O6B	121.0 (7)
C5—C4—C8—C7	8.64 (14)	C16—C23—C24—O6B	−117.0 (7)
C3—C4—C8—C7	−169.44 (15)	C26—C23—C24—O6A	−57.0 (4)
O4—C7—C8—O3	169.64 (13)	C16—C23—C24—O6A	65.0 (4)
C9—C7—C8—O3	−75.06 (16)	C26—C23—C24—O7B	−57.3 (4)
C16—C7—C8—O3	52.51 (18)	C16—C23—C24—O7B	64.7 (4)
O4—C7—C8—C4	−12.04 (13)	C26—C23—C24—O7A	119.1 (3)
C9—C7—C8—C4	103.26 (12)	C16—C23—C24—O7A	−119.0 (3)
C16—C7—C8—C4	−129.18 (12)	C27—O9—C26—O8	−8.3 (2)
O4—C7—C9—C14	5.46 (17)	C27—O9—C26—C23	169.40 (14)
C16—C7—C9—C14	127.14 (14)	C24—C23—C26—O8	110.02 (19)
C8—C7—C9—C14	−106.80 (15)	C16—C23—C26—O8	−15.2 (2)
O4—C7—C9—C10	−178.71 (11)	C24—C23—C26—O9	−67.62 (15)
C16—C7—C9—C10	−57.03 (17)	C16—C23—C26—O9	167.16 (12)
C8—C7—C9—C10	69.03 (15)	O6B—C24—O7A—C25A	6.4 (13)
C14—C9—C10—C11	−1.9 (2)	O6A—C24—O7A—C25A	−1.0 (6)
C7—C9—C10—C11	−177.88 (13)	O7B—C24—O7A—C25A	−3.8 (9)
C9—C10—C11—C12	0.9 (2)	C23—C24—O7A—C25A	−177.3 (3)
C15—O5—C12—C11	3.5 (2)	O6B—C24—O7B—C25B	−0.3 (11)
C15—O5—C12—C13	−176.57 (16)	O6A—C24—O7B—C25B	−1.2 (9)
C10—C11—C12—O5	−179.32 (15)	O7A—C24—O7B—C25B	4.6 (13)
C10—C11—C12—C13	0.8 (2)	C23—C24—O7B—C25B	178.2 (6)
O5—C12—C13—C14	178.68 (14)