Marchantin M tri­methyl ether

The title macrocycle, C₃₁H₃₀O₅, is comprised of two bi­benzyl ether moieties linked cyclically by spacers which each consist of two-carbon alkyl chains. The observed conformation of the macrocycle may be partly stabilized by intramolecular C-H...O close contacts. The packing appears to be directed by van der Waals forces. This work explains the occurrence of a signal found in the ¹H NMR spectra of both marchantin­quinone and marchantin M tri­methyl ether at [delta] = 5.49 and 5.56 p.p.m., respectively. The shift in the position of the expected peak can be explained by the proximity of an H atom belonging to one of the aromatic rings to another ring in the same mol­ecule.

Computing details

Data collection: MSC/AFC Diffractometer Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Software; data reduction: MSC/AFC Diffractometer Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1995); software used to prepare material for publication: PLATON (Spek, 1990).

4,17,20-trimethoxy-2,15-dioxapentacyclo[26.2.2.1^3,7.0^16,21]triaconta- 1(28),3,5,7(29),10,12,14 (30),16,18,20,24927),25-dodecaene

Crystal data

C31H30O5	F(000) = 1024
Mr = 482.10	Dx = 1.277 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
a = 14.937 (3) Å	Cell parameters from 22 reflections
b = 9.316 (5) Å	θ = 20.2–23.3°
c = 18.262 (2) Å	µ = 0.09 mm^−1
β = 98.877 (12)°	T = 293 K
V = 2510.7 (15) Å^3	Prism, colourless
Z = 4	0.31 × 0.24 × 0.08 mm

Data collection

Rigaku AFC7S diffractometer	2380 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.089
Graphite monochromator	θmax = 27.5°, θmin = 2.3°
θ/2θ scans	h = −2→19
Absorption correction: ψ scan MSC/AFC Diffractometer Software (Molecular Structure Corporation, 1993)	k = 0→12
Tmin = 0.974, Tmax = 0.993	l = −23→23
6844 measured reflections	3 standard reflections every 150 reflections
5746 independent reflections	intensity decay: 4.3%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.193	w = 1/[σ^2(Fo^2) + (0.0948P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max = 0.001
5746 reflections	Δρmax = 0.18 e Å^−3
345 parameters	Δρmin = −0.20 e Å^−3
48 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.016 (2)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.73707 (12)	0.3860 (2)	0.03557 (10)	0.0761 (6)
C1	0.65537 (18)	0.3836 (3)	0.06455 (14)	0.0675 (8)
C2	0.6071 (2)	0.2550 (4)	0.06483 (19)	0.0902 (10)
C3	0.5254 (2)	0.2570 (4)	0.0919 (2)	0.0952 (11)
H3	0.4935	0.1720	0.0948	0.114*
C4	0.4913 (2)	0.3825 (4)	0.11447 (17)	0.0804 (9)
H4	0.4365	0.3822	0.1327	0.096*
C5	0.53717 (17)	0.5090 (3)	0.11052 (14)	0.0653 (7)
C6	0.62140 (16)	0.5127 (3)	0.08456 (13)	0.0593 (7)
C7	0.66607 (17)	0.6546 (3)	0.07574 (14)	0.0664 (7)
H7A	0.6217	0.7178	0.0479	0.080*
H7B	0.7141	0.6397	0.0463	0.080*
C8	0.70659 (16)	0.7313 (3)	0.14760 (16)	0.0661 (7)
H8A	0.7068	0.8337	0.1381	0.079*
H8B	0.6674	0.7145	0.1844	0.079*
C9	0.80115 (16)	0.6859 (3)	0.17947 (13)	0.0532 (6)
C10	0.81970 (17)	0.5622 (3)	0.22019 (16)	0.0646 (7)
H10	0.7719	0.5054	0.2302	0.078*
C11	0.90758 (17)	0.5202 (3)	0.24657 (15)	0.0639 (7)
H11	0.9186	0.4358	0.2737	0.077*
C12	0.97823 (16)	0.6040 (3)	0.23242 (14)	0.0578 (7)
C13	0.96241 (18)	0.7289 (3)	0.19423 (15)	0.0698 (8)
H13	1.0106	0.7870	0.1863	0.084*
C14	0.87404 (18)	0.7693 (3)	0.16706 (15)	0.0646 (7)
H14	0.8636	0.8539	0.1400	0.078*
O2	1.06715 (11)	0.5643 (2)	0.26161 (10)	0.0757 (6)
C15	1.11334 (16)	0.4803 (3)	0.21717 (14)	0.0564 (6)
C16	1.19503 (17)	0.4218 (3)	0.25149 (15)	0.0612 (7)
C17	1.24424 (19)	0.3371 (3)	0.2103 (2)	0.0789 (9)
H17	1.2991	0.2981	0.2324	0.095*
C18	1.21306 (18)	0.3098 (3)	0.13704 (18)	0.0750 (8)
H18	1.2474	0.2521	0.1104	0.090*
C19	1.13254 (17)	0.3652 (3)	0.10176 (15)	0.0598 (7)
C20	1.08300 (17)	0.4518 (3)	0.14389 (14)	0.0584 (7)
H20	1.0282	0.4909	0.1216	0.070*
C21	1.09538 (18)	0.3283 (3)	0.02324 (15)	0.0671 (7)
H21A	1.1455	0.3129	−0.0039	0.081*
H21B	1.0607	0.4094	0.0008	0.081*
C22	1.03505 (17)	0.1957 (3)	0.01500 (15)	0.0670 (7)
H22A	1.0124	0.1808	−0.0371	0.080*
H22B	1.0712	0.1126	0.0327	0.080*
C23	0.95513 (17)	0.2065 (3)	0.05718 (14)	0.0548 (6)
C24	0.87992 (16)	0.2865 (3)	0.02916 (13)	0.0568 (6)
H24	0.8771	0.3309	−0.0167	0.068*
C25	0.80829 (16)	0.3011 (3)	0.06906 (14)	0.0580 (7)
C26	0.81165 (17)	0.2364 (3)	0.13696 (14)	0.0630 (7)
H26	0.7639	0.2465	0.1637	0.076*
C27	0.88635 (18)	0.1565 (3)	0.16490 (15)	0.0641 (7)
H27	0.8889	0.1117	0.2107	0.077*
C28	0.95829 (18)	0.1422 (3)	0.12528 (15)	0.0636 (7)
H28	1.0089	0.0888	0.1450	0.076*
O3A	0.6354 (4)	0.1114 (5)	0.0583 (3)	0.0871 (15)	0.514 (7)
C29A	0.6391 (6)	0.0839 (11)	−0.0174 (4)	0.103 (2)	0.514 (7)
H29A	0.6448	−0.0175	−0.0248	0.155*	0.514 (7)
H29B	0.6904	0.1324	−0.0317	0.155*	0.514 (7)
H29C	0.5846	0.1181	−0.0471	0.155*	0.514 (7)
O3B	0.6523 (4)	0.1580 (6)	0.0230 (4)	0.0912 (17)	0.486 (7)
C29B	0.5984 (6)	0.0340 (7)	0.0015 (6)	0.104 (2)	0.486 (7)
H29D	0.6293	−0.0263	−0.0292	0.156*	0.486 (7)
H29E	0.5411	0.0630	−0.0257	0.156*	0.486 (7)
H29F	0.5887	−0.0182	0.0449	0.156*	0.486 (7)
O4	0.50610 (12)	0.6407 (2)	0.12934 (11)	0.0835 (6)
C30	0.42074 (19)	0.6454 (5)	0.1550 (2)	0.1081 (12)
H30A	0.4068	0.7428	0.1662	0.162*
H30B	0.4234	0.5878	0.1989	0.162*
H30C	0.3745	0.6088	0.1173	0.162*
O5	1.21803 (12)	0.4541 (2)	0.32551 (11)	0.0797 (6)
C31	1.2981 (2)	0.3910 (4)	0.3634 (2)	0.1196 (14)
H31A	1.3068	0.4203	0.4144	0.179*
H31B	1.3490	0.4215	0.3409	0.179*
H31C	1.2930	0.2883	0.3605	0.179*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0638 (12)	0.1041 (15)	0.0610 (11)	0.0267 (11)	0.0117 (9)	0.0012 (10)
C1	0.0504 (15)	0.095 (2)	0.0563 (16)	0.0115 (16)	0.0059 (12)	−0.0055 (14)
C2	0.071 (2)	0.085 (2)	0.105 (3)	0.0066 (18)	−0.0164 (18)	−0.0312 (19)
C3	0.0577 (19)	0.099 (3)	0.122 (3)	−0.0139 (19)	−0.0080 (18)	−0.007 (2)
C4	0.0516 (16)	0.106 (3)	0.081 (2)	−0.0031 (18)	0.0042 (15)	−0.0009 (18)
C5	0.0448 (14)	0.094 (2)	0.0559 (15)	0.0058 (15)	0.0038 (12)	0.0018 (14)
C6	0.0480 (14)	0.0822 (18)	0.0475 (14)	0.0099 (14)	0.0065 (11)	0.0040 (13)
C7	0.0555 (16)	0.0837 (19)	0.0622 (17)	0.0163 (14)	0.0163 (13)	0.0168 (14)
C8	0.0547 (15)	0.0646 (16)	0.0831 (19)	0.0124 (13)	0.0237 (14)	0.0029 (14)
C9	0.0533 (14)	0.0505 (14)	0.0586 (15)	0.0030 (12)	0.0172 (11)	−0.0078 (12)
C10	0.0523 (15)	0.0605 (16)	0.0830 (19)	−0.0047 (12)	0.0167 (13)	0.0060 (14)
C11	0.0635 (16)	0.0546 (15)	0.0735 (17)	0.0025 (13)	0.0096 (14)	0.0040 (13)
C12	0.0525 (15)	0.0675 (17)	0.0527 (14)	0.0031 (13)	0.0062 (12)	−0.0108 (13)
C13	0.0559 (16)	0.0764 (19)	0.0769 (19)	−0.0172 (15)	0.0094 (14)	0.0048 (15)
C14	0.0696 (17)	0.0529 (15)	0.0725 (18)	−0.0050 (13)	0.0146 (14)	0.0044 (13)
O2	0.0530 (11)	0.1058 (15)	0.0652 (12)	0.0098 (10)	−0.0008 (9)	−0.0158 (11)
C15	0.0494 (14)	0.0606 (15)	0.0599 (16)	−0.0026 (12)	0.0114 (12)	0.0027 (12)
C16	0.0484 (15)	0.0651 (16)	0.0675 (17)	−0.0141 (13)	0.0009 (13)	0.0116 (14)
C17	0.0475 (15)	0.0796 (19)	0.109 (3)	0.0066 (15)	0.0091 (17)	0.0025 (18)
C18	0.0533 (17)	0.0761 (19)	0.099 (2)	0.0034 (15)	0.0213 (16)	−0.0040 (17)
C19	0.0542 (15)	0.0561 (15)	0.0731 (17)	−0.0025 (13)	0.0229 (13)	0.0026 (13)
C20	0.0492 (13)	0.0620 (15)	0.0643 (17)	0.0046 (12)	0.0102 (12)	0.0050 (13)
C21	0.0678 (17)	0.0698 (17)	0.0709 (18)	0.0017 (14)	0.0331 (14)	−0.0008 (14)
C22	0.0679 (17)	0.0645 (16)	0.0732 (18)	0.0079 (14)	0.0258 (14)	−0.0108 (14)
C23	0.0603 (15)	0.0493 (13)	0.0579 (15)	−0.0011 (12)	0.0188 (12)	−0.0104 (12)
C24	0.0636 (16)	0.0568 (14)	0.0515 (14)	0.0014 (13)	0.0131 (12)	−0.0095 (12)
C25	0.0557 (15)	0.0631 (15)	0.0554 (15)	0.0058 (13)	0.0086 (12)	−0.0128 (13)
C26	0.0607 (16)	0.0705 (17)	0.0604 (16)	0.0024 (14)	0.0175 (13)	−0.0074 (13)
C27	0.0725 (18)	0.0638 (16)	0.0588 (15)	0.0043 (14)	0.0188 (14)	0.0040 (13)
C28	0.0618 (16)	0.0564 (15)	0.0741 (18)	0.0112 (13)	0.0151 (14)	0.0015 (13)
O3A	0.091 (3)	0.084 (3)	0.087 (3)	−0.011 (2)	0.018 (3)	−0.006 (2)
C29A	0.110 (5)	0.110 (5)	0.097 (4)	−0.012 (4)	0.041 (4)	−0.016 (4)
O3B	0.086 (3)	0.083 (3)	0.106 (4)	−0.012 (3)	0.016 (3)	−0.027 (3)
C29B	0.102 (5)	0.081 (4)	0.130 (5)	−0.023 (4)	0.022 (4)	−0.015 (4)
O4	0.0530 (11)	0.1042 (16)	0.0978 (15)	0.0167 (11)	0.0254 (10)	−0.0053 (12)
C30	0.0576 (19)	0.157 (3)	0.115 (3)	0.017 (2)	0.0314 (19)	−0.014 (3)
O5	0.0589 (11)	0.0918 (14)	0.0826 (14)	−0.0054 (10)	−0.0070 (10)	0.0129 (11)
C31	0.083 (2)	0.138 (3)	0.120 (3)	0.010 (2)	−0.043 (2)	0.008 (3)

Geometric parameters (Å, º)

O1—C25	1.389 (3)	C18—C19	1.374 (4)
O1—C1	1.403 (3)	C18—H18	0.9300
C1—C6	1.377 (4)	C19—C20	1.402 (3)
C1—C2	1.399 (4)	C19—C21	1.495 (4)
C2—C3	1.386 (5)	C20—H20	0.9300
C2—O3A	1.414 (5)	C21—C22	1.523 (4)
C2—O3B	1.419 (5)	C21—H21A	0.9700
C3—C4	1.363 (5)	C21—H21B	0.9700
C3—H3	0.9300	C22—C23	1.521 (3)
C4—C5	1.371 (4)	C22—H22A	0.9700
C4—H4	0.9300	C22—H22B	0.9700
C5—O4	1.374 (3)	C23—C28	1.374 (4)
C5—C6	1.412 (3)	C23—C24	1.379 (3)
C6—C7	1.500 (4)	C24—C25	1.391 (3)
C7—C8	1.534 (4)	C24—H24	0.9300
C7—H7A	0.9700	C25—C26	1.373 (4)
C7—H7B	0.9700	C26—C27	1.372 (4)
C8—C9	1.503 (3)	C26—H26	0.9300
C8—H8A	0.9700	C27—C28	1.391 (4)
C8—H8B	0.9700	C27—H27	0.9300
C9—C10	1.376 (4)	C28—H28	0.9300
C9—C14	1.384 (3)	O3A—C29A	1.416 (6)
C10—C11	1.383 (4)	C29A—H29A	0.9600
C10—H10	0.9300	C29A—H29B	0.9600
C11—C12	1.369 (3)	C29A—H29C	0.9600
C11—H11	0.9300	O3B—C29B	1.428 (6)
C12—C13	1.358 (4)	C29B—H29D	0.9600
C12—O2	1.402 (3)	C29B—H29E	0.9600
C13—C14	1.389 (4)	C29B—H29F	0.9600
C13—H13	0.9300	O4—C30	1.425 (3)
C14—H14	0.9300	C30—H30A	0.9600
O2—C15	1.386 (3)	C30—H30B	0.9600
C15—C20	1.371 (4)	C30—H30C	0.9600
C15—C16	1.394 (3)	O5—C31	1.414 (3)
C16—O5	1.376 (3)	C31—H31A	0.9600
C16—C17	1.378 (4)	C31—H31B	0.9600
C17—C18	1.371 (4)	C31—H31C	0.9600
C17—H17	0.9300
C25—O1—C1	118.4 (2)	C18—C19—C20	117.2 (3)
C6—C1—C2	122.4 (3)	C18—C19—C21	122.1 (3)
C6—C1—O1	117.6 (3)	C20—C19—C21	120.6 (2)
C2—C1—O1	119.6 (3)	C15—C20—C19	121.6 (2)
C3—C2—C1	118.2 (3)	C15—C20—H20	119.2
C3—C2—O3A	109.5 (4)	C19—C20—H20	119.2
C1—C2—O3A	130.4 (4)	C19—C21—C22	114.0 (2)
C3—C2—O3B	136.0 (4)	C19—C21—H21A	108.7
C1—C2—O3B	104.8 (3)	C22—C21—H21A	108.7
O3A—C2—O3B	34.8 (2)	C19—C21—H21B	108.7
C4—C3—C2	120.6 (3)	C22—C21—H21B	108.7
C4—C3—H3	119.7	H21A—C21—H21B	107.6
C2—C3—H3	119.7	C23—C22—C21	113.3 (2)
C3—C4—C5	120.6 (3)	C23—C22—H22A	108.9
C3—C4—H4	119.7	C21—C22—H22A	108.9
C5—C4—H4	119.7	C23—C22—H22B	108.9
C4—C5—O4	124.3 (2)	C21—C22—H22B	108.9
C4—C5—C6	121.1 (3)	H22A—C22—H22B	107.7
O4—C5—C6	114.5 (3)	C28—C23—C24	118.9 (2)
C1—C6—C5	116.9 (3)	C28—C23—C22	120.6 (2)
C1—C6—C7	123.6 (2)	C24—C23—C22	120.4 (2)
C5—C6—C7	119.4 (3)	C23—C24—C25	120.5 (2)
C6—C7—C8	116.2 (2)	C23—C24—H24	119.8
C6—C7—H7A	108.2	C25—C24—H24	119.8
C8—C7—H7A	108.2	C26—C25—O1	124.5 (2)
C6—C7—H7B	108.2	C26—C25—C24	120.4 (2)
C8—C7—H7B	108.2	O1—C25—C24	115.1 (2)
H7A—C7—H7B	107.4	C27—C26—C25	119.2 (2)
C9—C8—C7	115.1 (2)	C27—C26—H26	120.4
C9—C8—H8A	108.5	C25—C26—H26	120.4
C7—C8—H8A	108.5	C26—C27—C28	120.5 (3)
C9—C8—H8B	108.5	C26—C27—H27	119.8
C7—C8—H8B	108.5	C28—C27—H27	119.8
H8A—C8—H8B	107.5	C23—C28—C27	120.5 (2)
C10—C9—C14	117.4 (2)	C23—C28—H28	119.8
C10—C9—C8	122.9 (2)	C27—C28—H28	119.8
C14—C9—C8	119.7 (2)	C2—O3A—C29A	108.1 (6)
C9—C10—C11	121.8 (2)	O3A—C29A—H29A	109.5
C9—C10—H10	119.1	O3A—C29A—H29B	109.5
C11—C10—H10	119.1	H29A—C29A—H29B	109.5
C12—C11—C10	119.4 (2)	O3A—C29A—H29C	109.5
C12—C11—H11	120.3	H29A—C29A—H29C	109.5
C10—C11—H11	120.3	H29B—C29A—H29C	109.5
C13—C12—C11	120.5 (2)	C2—O3B—C29B	111.6 (6)
C13—C12—O2	120.1 (2)	O3B—C29B—H29D	109.5
C11—C12—O2	119.4 (2)	O3B—C29B—H29E	109.5
C12—C13—C14	119.8 (2)	H29D—C29B—H29E	109.5
C12—C13—H13	120.1	O3B—C29B—H29F	109.5
C14—C13—H13	120.1	H29D—C29B—H29F	109.5
C9—C14—C13	121.2 (2)	H29E—C29B—H29F	109.5
C9—C14—H14	119.4	C5—O4—C30	117.6 (3)
C13—C14—H14	119.4	O4—C30—H30A	109.5
C15—O2—C12	117.02 (18)	O4—C30—H30B	109.5
C20—C15—O2	124.2 (2)	H30A—C30—H30B	109.5
C20—C15—C16	119.9 (2)	O4—C30—H30C	109.5
O2—C15—C16	116.0 (2)	H30A—C30—H30C	109.5
O5—C16—C17	126.0 (3)	H30B—C30—H30C	109.5
O5—C16—C15	115.1 (2)	C16—O5—C31	117.0 (3)
C17—C16—C15	118.8 (3)	O5—C31—H31A	109.5
C18—C17—C16	120.6 (3)	O5—C31—H31B	109.5
C18—C17—H17	119.7	H31A—C31—H31B	109.5
C16—C17—H17	119.7	O5—C31—H31C	109.5
C17—C18—C19	121.9 (3)	H31A—C31—H31C	109.5
C17—C18—H18	119.0	H31B—C31—H31C	109.5
C19—C18—H18	119.0
C25—O1—C1—C6	125.1 (3)	C20—C15—C16—O5	−178.4 (2)
C25—O1—C1—C2	−61.6 (3)	O2—C15—C16—O5	0.9 (3)
C6—C1—C2—C3	−5.2 (5)	C20—C15—C16—C17	0.7 (4)
O1—C1—C2—C3	−178.2 (3)	O2—C15—C16—C17	180.0 (2)
C6—C1—C2—O3A	−168.2 (4)	O5—C16—C17—C18	178.4 (3)
O1—C1—C2—O3A	18.8 (5)	C15—C16—C17—C18	−0.6 (4)
C6—C1—C2—O3B	164.8 (4)	C16—C17—C18—C19	0.2 (4)
O1—C1—C2—O3B	−8.2 (5)	C17—C18—C19—C20	0.1 (4)
C1—C2—C3—C4	2.9 (5)	C17—C18—C19—C21	−176.1 (3)
O3A—C2—C3—C4	169.3 (3)	O2—C15—C20—C19	−179.6 (2)
O3B—C2—C3—C4	−163.2 (6)	C16—C15—C20—C19	−0.4 (4)
C2—C3—C4—C5	0.2 (5)	C18—C19—C20—C15	0.0 (4)
C3—C4—C5—O4	177.4 (3)	C21—C19—C20—C15	176.2 (2)
C3—C4—C5—C6	−1.3 (4)	C18—C19—C21—C22	89.0 (3)
C2—C1—C6—C5	4.2 (4)	C20—C19—C21—C22	−87.0 (3)
O1—C1—C6—C5	177.3 (2)	C19—C21—C22—C23	57.0 (3)
C2—C1—C6—C7	−172.0 (3)	C21—C22—C23—C28	−99.2 (3)
O1—C1—C6—C7	1.1 (4)	C21—C22—C23—C24	77.9 (3)
C4—C5—C6—C1	−0.8 (4)	C28—C23—C24—C25	−0.3 (4)
O4—C5—C6—C1	−179.6 (2)	C22—C23—C24—C25	−177.5 (2)
C4—C5—C6—C7	175.5 (2)	C1—O1—C25—C26	−13.5 (4)
O4—C5—C6—C7	−3.3 (3)	C1—O1—C25—C24	167.7 (2)
C1—C6—C7—C8	−111.7 (3)	C23—C24—C25—C26	0.2 (4)
C5—C6—C7—C8	72.2 (3)	C23—C24—C25—O1	179.0 (2)
C6—C7—C8—C9	85.1 (3)	O1—C25—C26—C27	−179.0 (2)
C7—C8—C9—C10	−79.5 (3)	C24—C25—C26—C27	−0.3 (4)
C7—C8—C9—C14	99.4 (3)	C25—C26—C27—C28	0.6 (4)
C14—C9—C10—C11	−1.4 (4)	C24—C23—C28—C27	0.6 (4)
C8—C9—C10—C11	177.5 (2)	C22—C23—C28—C27	177.7 (2)
C9—C10—C11—C12	0.5 (4)	C26—C27—C28—C23	−0.7 (4)
C10—C11—C12—C13	1.4 (4)	C3—C2—O3A—C29A	117.7 (7)
C10—C11—C12—O2	177.5 (2)	C1—C2—O3A—C29A	−78.2 (7)
C11—C12—C13—C14	−2.3 (4)	O3B—C2—O3A—C29A	−28.0 (6)
O2—C12—C13—C14	−178.4 (2)	C3—C2—O3B—C29B	2.7 (11)
C10—C9—C14—C13	0.5 (4)	C1—C2—O3B—C29B	−164.7 (7)
C8—C9—C14—C13	−178.5 (2)	O3A—C2—O3B—C29B	52.5 (7)
C12—C13—C14—C9	1.3 (4)	C4—C5—O4—C30	0.4 (4)
C13—C12—O2—C15	−91.4 (3)	C6—C5—O4—C30	179.1 (3)
C11—C12—O2—C15	92.5 (3)	C17—C16—O5—C31	−2.1 (4)
C12—O2—C15—C20	9.9 (4)	C15—C16—O5—C31	176.9 (3)
C12—O2—C15—C16	−169.4 (2)