Tetra-methyl biphenyl-2,3,3',4'-tetra-carboxyl-ate.

The asymmetric unit of the title compound, C(20)H(18)O(8), contains two mol-ecules with small geometric differences. The dihedral angles between the benzene rings are 62.94 (12) and 59.99 (12)°. The dihedral angles between the carboxylate groups in the 2- and 3-positions are 81.72 (13) and 65.54 (15)°, respectively. However, the dihedral angles between the carboxylate groups in the 3' and 4'-positions are 67.24 (15) and 59.98 (17)°, respectively.

Related literature

For related literature, see: Ding et al. (1992 ▶); Ermer (1981 ▶); Ghosh & Mittal (1996 ▶); Jiang et al. (2008 ▶); Rozhanskii et al. (2000 ▶).

Experimental

Crystal data

C20H18O8

M = 386.34

Monoclinic,

a = 14.395 (4) Å

b = 13.453 (4) Å

c = 21.013 (3) Å

β = 108.45 (4)°

V = 3860.1 (19) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 297 (2) K

0.45 × 0.42 × 0.38 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

8168 measured reflections

6906 independent reflections

2997 reflections with I > 2σ(I)

R int = 0.006

3 standard reflections every 300 reflections intensity decay: 1.8%

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.163

S = 1.03

6906 reflections

515 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.23 e Å−3

Data collection: DIFRAC (Gabe & White, 1993 ▶); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ▶); 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 global, I. DOI: 10.1107/S1600536808025762/rk2106sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025762/rk2106Isup2.hkl

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

C20H18O8	F000 = 1616
Mr = 386.34	Dx = 1.330 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 31 reflections
a = 14.395 (4) Å	θ = 4.7–9.2º
b = 13.453 (4) Å	µ = 0.10 mm−1
c = 21.013 (3) Å	T = 297 (2) K
β = 108.45 (4)º	Block, colourless
V = 3860.1 (19) Å3	0.45 × 0.42 × 0.38 mm
Z = 8

Enraf–Nonius CAD-4 diffractometer	Rint = 0.006
Radiation source: fine-focus sealed tube	θmax = 25.3º
Monochromator: graphite	θmin = 1.8º
T = 297(2) K	h = −17→16
ω/2θ scans	k = 0→16
Absorption correction: none	l = −14→25
8168 measured reflections	3 standard reflections
6906 independent reflections	every 300 reflections
2997 reflections with I > 2σ(I)	intensity decay: 1.8%

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)] = 0.059	H-atom parameters constrained
wR(F2) = 0.163	w = 1/[σ2(Fo2) + (0.069P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
6906 reflections	Δρmax = 0.28 e Å−3
515 parameters	Δρmin = −0.23 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.58582 (18)	0.6473 (2)	0.10659 (14)	0.0722 (8)
O2	0.66768 (17)	0.78792 (19)	0.13706 (13)	0.0628 (7)
O3	0.37936 (18)	0.57886 (17)	0.11045 (13)	0.0602 (7)
O4	0.38789 (17)	0.62465 (17)	0.00901 (12)	0.0582 (7)
O5	0.02260 (18)	0.59487 (19)	0.15264 (13)	0.0671 (8)
O6	−0.00811 (19)	0.7556 (2)	0.16431 (13)	0.0718 (8)
O7	−0.12482 (19)	0.6405 (2)	0.02572 (14)	0.0824 (9)
O8	−0.08492 (18)	0.58818 (19)	−0.06318 (13)	0.0691 (8)
C1	0.3321 (3)	0.9024 (2)	0.11080 (17)	0.0492 (9)
H1	0.2773	0.9389	0.1110	0.059*
C2	0.4233 (3)	0.9456 (3)	0.13244 (17)	0.0510 (9)
H2	0.4297	1.0114	0.1467	0.061*
C3	0.5055 (2)	0.8924 (2)	0.13322 (16)	0.0463 (9)
H3	0.5667	0.9227	0.1475	0.056*
C4	0.4974 (2)	0.7938 (2)	0.11289 (15)	0.0389 (8)
C5	0.4049 (2)	0.7492 (2)	0.09027 (14)	0.0363 (8)
C6	0.3216 (2)	0.8033 (2)	0.08845 (15)	0.0412 (8)
C7	0.5861 (2)	0.7338 (3)	0.11817 (16)	0.0454 (9)
C8	0.7599 (3)	0.7343 (3)	0.1475 (2)	0.0779 (13)
H8A	0.7660	0.6831	0.1804	0.117*
H8B	0.8137	0.7798	0.1629	0.117*
H8C	0.7603	0.7049	0.1059	0.117*
C9	0.3917 (2)	0.6403 (3)	0.07216 (18)	0.0431 (8)
C10	0.3676 (3)	0.5227 (3)	−0.0148 (2)	0.0868 (14)
H10A	0.4082	0.4780	0.0179	0.130*
H10B	0.3811	0.5153	−0.0564	0.130*
H10C	0.2999	0.5076	−0.0215	0.130*
C11	0.2216 (2)	0.7587 (2)	0.06406 (16)	0.0400 (8)
C12	0.1815 (3)	0.7259 (3)	−0.00211 (16)	0.0503 (9)
H12	0.2171	0.7329	−0.0319	0.060*
C13	0.0899 (2)	0.6834 (3)	−0.02369 (17)	0.0506 (9)
H13	0.0647	0.6613	−0.0678	0.061*
C14	0.0347 (2)	0.6729 (2)	0.01933 (16)	0.0431 (8)
C15	0.0746 (2)	0.7055 (2)	0.08603 (16)	0.0408 (8)
C16	0.1658 (2)	0.7487 (2)	0.10680 (15)	0.0421 (8)
H16	0.1907	0.7718	0.1506	0.051*
C17	0.0229 (3)	0.6902 (3)	0.13731 (18)	0.0508 (9)
C18	−0.0328 (3)	0.5667 (3)	0.1968 (2)	0.0904 (15)
H18A	−0.0385	0.6229	0.2234	0.136*
H18B	0.0005	0.5138	0.2257	0.136*
H18C	−0.0969	0.5448	0.1704	0.136*
C19	−0.0661 (3)	0.6322 (3)	−0.00428 (19)	0.0522 (9)
C20	−0.1833 (3)	0.5486 (3)	−0.0923 (2)	0.0846 (14)
H20A	−0.1894	0.4880	−0.0698	0.127*
H20B	−0.1953	0.5356	−0.1391	0.127*
H20C	−0.2301	0.5961	−0.0870	0.127*
O9	0.90819 (19)	0.3219 (2)	0.20321 (13)	0.0730 (8)
O10	0.8394 (2)	0.1751 (2)	0.19739 (18)	0.0968 (11)
O11	0.62367 (18)	0.09734 (17)	0.17382 (12)	0.0558 (7)
O12	0.6628 (2)	0.15331 (17)	0.08491 (12)	0.0649 (7)
O13	0.2462 (2)	0.0867 (2)	0.19228 (14)	0.0765 (8)
O14	0.2231 (2)	0.2456 (2)	0.21508 (15)	0.0870 (10)
O15	0.1182 (2)	0.1385 (2)	0.06290 (15)	0.0838 (9)
O16	0.17875 (19)	0.0866 (2)	−0.01709 (14)	0.0790 (8)
C21	0.5672 (3)	0.4153 (3)	0.18722 (18)	0.0582 (10)
H21	0.5100	0.4484	0.1863	0.070*
C22	0.6571 (3)	0.4616 (3)	0.21457 (18)	0.0625 (11)
H22	0.6598	0.5251	0.2325	0.075*
C23	0.7419 (3)	0.4149 (3)	0.21548 (17)	0.0542 (10)
H23	0.8014	0.4478	0.2328	0.065*
C24	0.7401 (2)	0.3184 (2)	0.19076 (16)	0.0446 (9)
C25	0.6495 (2)	0.2707 (2)	0.16425 (15)	0.0416 (8)
C26	0.5620 (2)	0.3192 (2)	0.16103 (15)	0.0442 (8)
C27	0.8319 (3)	0.2630 (3)	0.19680 (17)	0.0506 (9)
C28	1.0022 (3)	0.2714 (4)	0.2128 (2)	0.0868 (14)
H28A	1.0181	0.2315	0.2527	0.130*
H28B	1.0526	0.3201	0.2172	0.130*
H28C	0.9973	0.2297	0.1748	0.130*
C29	0.6447 (2)	0.1636 (2)	0.14292 (17)	0.0413 (8)
C30	0.6633 (4)	0.0514 (3)	0.0632 (2)	0.1001 (17)
H30A	0.7030	0.0119	0.0997	0.150*
H30B	0.6896	0.0486	0.0265	0.150*
H30C	0.5975	0.0261	0.0488	0.150*
C31	0.4657 (2)	0.2706 (2)	0.13009 (17)	0.0448 (8)
C32	0.4016 (3)	0.2537 (3)	0.16732 (17)	0.0513 (9)
H32	0.4192	0.2751	0.2116	0.062*
C33	0.3130 (3)	0.2060 (3)	0.13961 (17)	0.0478 (9)
C34	0.2835 (2)	0.1771 (3)	0.07211 (17)	0.0484 (9)
C35	0.3463 (3)	0.1945 (3)	0.03489 (17)	0.0548 (10)
H35	0.3278	0.1752	−0.0099	0.066*
C36	0.4362 (3)	0.2404 (3)	0.06343 (17)	0.0546 (10)
H36	0.4772	0.2510	0.0377	0.066*
C37	0.2537 (3)	0.1852 (3)	0.1855 (2)	0.0604 (10)
C38	0.1830 (4)	0.0548 (4)	0.2310 (3)	0.1100 (18)
H38A	0.1968	0.0941	0.2711	0.165*
H38B	0.1951	−0.0140	0.2429	0.165*
H38C	0.1156	0.0634	0.2045	0.165*
C39	0.1845 (3)	0.1319 (3)	0.0402 (2)	0.0579 (10)
C40	0.0844 (3)	0.0424 (4)	−0.0540 (2)	0.1078 (17)
H40A	0.0676	−0.0072	−0.0267	0.162*
H40B	0.0886	0.0122	−0.0944	0.162*
H40C	0.0349	0.0931	−0.0652	0.162*

	U11	U22	U33	U12	U13	U23
O1	0.0541 (17)	0.0528 (18)	0.107 (2)	0.0050 (14)	0.0223 (15)	−0.0148 (16)
O2	0.0398 (16)	0.0647 (18)	0.0844 (19)	−0.0051 (14)	0.0202 (14)	−0.0119 (14)
O3	0.0691 (18)	0.0385 (15)	0.0755 (18)	−0.0081 (13)	0.0263 (15)	0.0061 (13)
O4	0.0716 (18)	0.0473 (15)	0.0569 (15)	−0.0036 (13)	0.0221 (13)	−0.0166 (12)
O5	0.0744 (19)	0.0595 (18)	0.0815 (19)	0.0036 (14)	0.0446 (15)	0.0158 (14)
O6	0.079 (2)	0.0711 (19)	0.0828 (19)	0.0027 (16)	0.0499 (17)	−0.0061 (16)
O7	0.0496 (17)	0.117 (3)	0.086 (2)	−0.0181 (17)	0.0287 (16)	−0.0200 (18)
O8	0.0518 (17)	0.0757 (19)	0.0743 (19)	−0.0166 (14)	0.0123 (14)	−0.0197 (15)
C1	0.048 (2)	0.037 (2)	0.065 (2)	0.0078 (18)	0.0200 (19)	−0.0003 (18)
C2	0.052 (2)	0.035 (2)	0.065 (2)	−0.0052 (19)	0.0175 (19)	−0.0066 (17)
C3	0.041 (2)	0.045 (2)	0.050 (2)	−0.0102 (18)	0.0102 (17)	−0.0029 (17)
C4	0.041 (2)	0.037 (2)	0.0397 (18)	−0.0047 (17)	0.0139 (16)	−0.0010 (15)
C5	0.040 (2)	0.0340 (19)	0.0376 (17)	−0.0015 (16)	0.0159 (15)	−0.0031 (14)
C6	0.043 (2)	0.040 (2)	0.0428 (19)	−0.0040 (17)	0.0162 (16)	−0.0021 (16)
C7	0.039 (2)	0.051 (2)	0.046 (2)	−0.006 (2)	0.0132 (17)	−0.0085 (18)
C8	0.042 (2)	0.097 (3)	0.097 (3)	0.003 (2)	0.025 (2)	−0.009 (3)
C9	0.036 (2)	0.038 (2)	0.053 (2)	−0.0046 (16)	0.0122 (17)	−0.0080 (18)
C10	0.108 (4)	0.054 (3)	0.099 (3)	−0.012 (2)	0.032 (3)	−0.040 (2)
C11	0.0333 (19)	0.041 (2)	0.046 (2)	0.0034 (16)	0.0129 (16)	0.0048 (16)
C12	0.049 (2)	0.063 (2)	0.045 (2)	−0.005 (2)	0.0236 (18)	0.0031 (18)
C13	0.044 (2)	0.063 (2)	0.043 (2)	−0.0078 (19)	0.0101 (17)	−0.0032 (18)
C14	0.038 (2)	0.043 (2)	0.049 (2)	0.0002 (17)	0.0156 (17)	0.0048 (16)
C15	0.035 (2)	0.043 (2)	0.047 (2)	0.0055 (17)	0.0177 (16)	0.0065 (16)
C16	0.042 (2)	0.047 (2)	0.0380 (18)	0.0012 (17)	0.0128 (16)	−0.0007 (16)
C17	0.043 (2)	0.056 (3)	0.055 (2)	−0.0043 (19)	0.0188 (18)	0.006 (2)
C18	0.099 (4)	0.091 (3)	0.102 (3)	−0.012 (3)	0.061 (3)	0.027 (3)
C19	0.041 (2)	0.057 (2)	0.056 (2)	−0.0014 (19)	0.0112 (19)	0.004 (2)
C20	0.057 (3)	0.083 (3)	0.097 (3)	−0.016 (2)	−0.001 (2)	−0.015 (3)
O9	0.0493 (17)	0.0671 (18)	0.105 (2)	−0.0108 (15)	0.0274 (15)	−0.0144 (16)
O10	0.068 (2)	0.0443 (19)	0.179 (3)	0.0064 (15)	0.040 (2)	0.0258 (19)
O11	0.0757 (18)	0.0373 (14)	0.0639 (16)	−0.0082 (13)	0.0355 (14)	0.0004 (12)
O12	0.107 (2)	0.0389 (15)	0.0671 (17)	0.0001 (14)	0.0528 (16)	−0.0036 (12)
O13	0.083 (2)	0.073 (2)	0.086 (2)	0.0099 (16)	0.0456 (17)	0.0200 (16)
O14	0.089 (2)	0.089 (2)	0.106 (2)	0.0118 (18)	0.064 (2)	−0.0156 (19)
O15	0.0512 (18)	0.110 (3)	0.092 (2)	−0.0072 (17)	0.0262 (16)	0.0036 (18)
O16	0.0606 (19)	0.092 (2)	0.076 (2)	−0.0128 (16)	0.0102 (15)	−0.0203 (17)
C21	0.063 (3)	0.045 (2)	0.064 (2)	0.016 (2)	0.017 (2)	−0.0009 (19)
C22	0.078 (3)	0.037 (2)	0.066 (3)	0.003 (2)	0.014 (2)	−0.0107 (18)
C23	0.063 (3)	0.040 (2)	0.054 (2)	−0.014 (2)	0.0111 (19)	0.0025 (18)
C24	0.051 (2)	0.035 (2)	0.047 (2)	−0.0040 (18)	0.0135 (17)	0.0053 (16)
C25	0.051 (2)	0.0314 (19)	0.0431 (19)	0.0020 (17)	0.0155 (17)	0.0035 (15)
C26	0.047 (2)	0.040 (2)	0.046 (2)	0.0035 (18)	0.0131 (17)	0.0028 (16)
C27	0.045 (2)	0.052 (3)	0.052 (2)	−0.003 (2)	0.0130 (18)	0.0053 (18)
C28	0.052 (3)	0.110 (4)	0.104 (4)	−0.005 (3)	0.033 (3)	−0.019 (3)
C29	0.045 (2)	0.038 (2)	0.044 (2)	−0.0016 (17)	0.0178 (17)	−0.0008 (17)
C30	0.186 (6)	0.047 (3)	0.099 (3)	−0.003 (3)	0.090 (4)	−0.020 (2)
C31	0.043 (2)	0.040 (2)	0.050 (2)	0.0068 (17)	0.0127 (18)	0.0003 (16)
C32	0.053 (2)	0.053 (2)	0.048 (2)	0.018 (2)	0.0161 (19)	0.0037 (18)
C33	0.045 (2)	0.046 (2)	0.053 (2)	0.0133 (18)	0.0156 (18)	0.0049 (17)
C34	0.037 (2)	0.050 (2)	0.058 (2)	0.0106 (18)	0.0142 (19)	0.0061 (18)
C35	0.053 (2)	0.067 (3)	0.040 (2)	0.006 (2)	0.0094 (19)	0.0007 (18)
C36	0.053 (2)	0.062 (2)	0.050 (2)	−0.004 (2)	0.0187 (19)	−0.0010 (19)
C37	0.049 (2)	0.070 (3)	0.064 (3)	0.009 (2)	0.021 (2)	0.006 (2)
C38	0.131 (4)	0.105 (4)	0.122 (4)	−0.001 (3)	0.080 (4)	0.032 (3)
C39	0.051 (3)	0.058 (3)	0.060 (3)	0.008 (2)	0.011 (2)	0.012 (2)
C40	0.078 (4)	0.123 (4)	0.106 (4)	−0.041 (3)	0.004 (3)	−0.026 (3)

O1—C7	1.188 (4)	O9—C27	1.326 (4)
O2—C7	1.331 (4)	O9—C28	1.469 (4)
O2—C8	1.465 (4)	O10—C27	1.188 (4)
O3—C9	1.205 (4)	O11—C29	1.197 (4)
O4—C9	1.328 (4)	O12—C29	1.331 (4)
O4—C10	1.457 (4)	O12—C30	1.446 (4)
O5—C17	1.323 (4)	O13—C37	1.340 (4)
O5—C18	1.452 (4)	O13—C38	1.465 (4)
O6—C17	1.206 (4)	O14—C37	1.190 (4)
O7—C19	1.209 (4)	O15—C39	1.198 (4)
O8—C19	1.320 (4)	O16—C39	1.328 (4)
O8—C20	1.454 (4)	O16—C40	1.461 (5)
C1—C2	1.375 (5)	C21—C22	1.386 (5)
C1—C6	1.406 (4)	C21—C26	1.399 (4)
C1—H1	0.9300	C21—H21	0.9300
C2—C3	1.379 (4)	C22—C23	1.367 (5)
C2—H2	0.9300	C22—H22	0.9300
C3—C4	1.386 (4)	C23—C24	1.396 (4)
C3—H3	0.9300	C23—H23	0.9300
C4—C5	1.399 (4)	C24—C25	1.401 (4)
C4—C7	1.485 (4)	C24—C27	1.487 (5)
C5—C6	1.394 (4)	C25—C26	1.401 (4)
C5—C9	1.510 (4)	C25—C29	1.504 (4)
C6—C11	1.492 (4)	C26—C31	1.484 (5)
C8—H8A	0.9600	C28—H28A	0.9600
C8—H8B	0.9600	C28—H28B	0.9600
C8—H8C	0.9600	C28—H28C	0.9600
C10—H10A	0.9600	C30—H30A	0.9600
C10—H10B	0.9600	C30—H30B	0.9600
C10—H10C	0.9600	C30—H30C	0.9600
C11—C16	1.389 (4)	C31—C36	1.390 (4)
C11—C12	1.398 (4)	C31—C32	1.404 (4)
C12—C13	1.376 (4)	C32—C33	1.381 (5)
C12—H12	0.9300	C32—H32	0.9300
C13—C14	1.387 (4)	C33—C34	1.401 (5)
C13—H13	0.9300	C33—C37	1.502 (5)
C14—C15	1.406 (4)	C34—C35	1.391 (5)
C14—C19	1.481 (5)	C34—C39	1.497 (5)
C15—C16	1.373 (4)	C35—C36	1.386 (5)
C15—C17	1.506 (4)	C35—H35	0.9300
C16—H16	0.9300	C36—H36	0.9300
C18—H18A	0.9600	C38—H38A	0.9600
C18—H18B	0.9600	C38—H38B	0.9600
C18—H18C	0.9600	C38—H38C	0.9600
C20—H20A	0.9600	C40—H40A	0.9600
C20—H20B	0.9600	C40—H40B	0.9600
C20—H20C	0.9600	C40—H40C	0.9600
C7—O2—C8	116.6 (3)	C27—O9—C28	115.8 (3)
C9—O4—C10	115.6 (3)	C29—O12—C30	114.2 (3)
C17—O5—C18	117.0 (3)	C37—O13—C38	115.8 (3)
C19—O8—C20	116.2 (3)	C39—O16—C40	116.7 (3)
C2—C1—C6	120.1 (3)	C22—C21—C26	120.3 (4)
C2—C1—H1	119.9	C22—C21—H21	119.9
C6—C1—H1	119.9	C26—C21—H21	119.9
C1—C2—C3	120.7 (3)	C23—C22—C21	120.8 (4)
C1—C2—H2	119.6	C23—C22—H22	119.6
C3—C2—H2	119.6	C21—C22—H22	119.6
C2—C3—C4	120.3 (3)	C22—C23—C24	120.7 (4)
C2—C3—H3	119.9	C22—C23—H23	119.6
C4—C3—H3	119.9	C24—C23—H23	119.6
C3—C4—C5	119.6 (3)	C23—C24—C25	118.7 (3)
C3—C4—C7	120.7 (3)	C23—C24—C27	121.5 (3)
C5—C4—C7	119.6 (3)	C25—C24—C27	119.6 (3)
C6—C5—C4	120.2 (3)	C24—C25—C26	121.0 (3)
C6—C5—C9	117.4 (3)	C24—C25—C29	120.4 (3)
C4—C5—C9	122.2 (3)	C26—C25—C29	118.4 (3)
C5—C6—C1	119.1 (3)	C21—C26—C25	118.5 (3)
C5—C6—C11	121.8 (3)	C21—C26—C31	120.4 (3)
C1—C6—C11	119.1 (3)	C25—C26—C31	121.1 (3)
O1—C7—O2	122.8 (3)	O10—C27—O9	121.6 (4)
O1—C7—C4	124.8 (3)	O10—C27—C24	125.2 (4)
O2—C7—C4	112.4 (3)	O9—C27—C24	113.3 (3)
O2—C8—H8A	109.5	O9—C28—H28A	109.5
O2—C8—H8B	109.5	O9—C28—H28B	109.5
H8A—C8—H8B	109.5	H28A—C28—H28B	109.5
O2—C8—H8C	109.5	O9—C28—H28C	109.5
H8A—C8—H8C	109.5	H28A—C28—H28C	109.5
H8B—C8—H8C	109.5	H28B—C28—H28C	109.5
O3—C9—O4	126.2 (3)	O11—C29—O12	125.2 (3)
O3—C9—C5	122.1 (3)	O11—C29—C25	123.2 (3)
O4—C9—C5	111.6 (3)	O12—C29—C25	111.6 (3)
O4—C10—H10A	109.5	O12—C30—H30A	109.5
O4—C10—H10B	109.5	O12—C30—H30B	109.5
H10A—C10—H10B	109.5	H30A—C30—H30B	109.5
O4—C10—H10C	109.5	O12—C30—H30C	109.5
H10A—C10—H10C	109.5	H30A—C30—H30C	109.5
H10B—C10—H10C	109.5	H30B—C30—H30C	109.5
C16—C11—C12	118.1 (3)	C36—C31—C32	118.0 (3)
C16—C11—C6	120.6 (3)	C36—C31—C26	121.1 (3)
C12—C11—C6	121.2 (3)	C32—C31—C26	121.0 (3)
C13—C12—C11	120.7 (3)	C33—C32—C31	121.5 (3)
C13—C12—H12	119.7	C33—C32—H32	119.3
C11—C12—H12	119.7	C31—C32—H32	119.3
C12—C13—C14	121.0 (3)	C32—C33—C34	120.0 (3)
C12—C13—H13	119.5	C32—C33—C37	116.9 (3)
C14—C13—H13	119.5	C34—C33—C37	123.1 (3)
C13—C14—C15	118.6 (3)	C35—C34—C33	118.6 (3)
C13—C14—C19	121.5 (3)	C35—C34—C39	120.8 (3)
C15—C14—C19	119.8 (3)	C33—C34—C39	120.5 (3)
C16—C15—C14	119.8 (3)	C36—C35—C34	121.1 (3)
C16—C15—C17	118.0 (3)	C36—C35—H35	119.5
C14—C15—C17	122.1 (3)	C34—C35—H35	119.5
C15—C16—C11	121.7 (3)	C35—C36—C31	120.8 (3)
C15—C16—H16	119.1	C35—C36—H36	119.6
C11—C16—H16	119.1	C31—C36—H36	119.6
O6—C17—O5	124.2 (3)	O14—C37—O13	124.3 (4)
O6—C17—C15	125.3 (3)	O14—C37—C33	126.0 (4)
O5—C17—C15	110.3 (3)	O13—C37—C33	109.5 (3)
O5—C18—H18A	109.5	O13—C38—H38A	109.5
O5—C18—H18B	109.5	O13—C38—H38B	109.5
H18A—C18—H18B	109.5	H38A—C38—H38B	109.5
O5—C18—H18C	109.5	O13—C38—H38C	109.5
H18A—C18—H18C	109.5	H38A—C38—H38C	109.5
H18B—C18—H18C	109.5	H38B—C38—H38C	109.5
O7—C19—O8	124.1 (3)	O15—C39—O16	124.4 (4)
O7—C19—C14	124.3 (4)	O15—C39—C34	123.8 (4)
O8—C19—C14	111.6 (3)	O16—C39—C34	111.8 (3)
O8—C20—H20A	109.5	O16—C40—H40A	109.5
O8—C20—H20B	109.5	O16—C40—H40B	109.5
H20A—C20—H20B	109.5	H40A—C40—H40B	109.5
O8—C20—H20C	109.5	O16—C40—H40C	109.5
H20A—C20—H20C	109.5	H40A—C40—H40C	109.5
H20B—C20—H20C	109.5	H40B—C40—H40C	109.5
C6—C1—C2—C3	−0.7 (5)	C26—C21—C22—C23	1.1 (6)
C1—C2—C3—C4	−0.8 (5)	C21—C22—C23—C24	−2.0 (5)
C2—C3—C4—C5	1.3 (5)	C22—C23—C24—C25	0.7 (5)
C2—C3—C4—C7	−175.6 (3)	C22—C23—C24—C27	−174.5 (3)
C3—C4—C5—C6	−0.3 (4)	C23—C24—C25—C26	1.5 (5)
C7—C4—C5—C6	176.6 (3)	C27—C24—C25—C26	176.7 (3)
C3—C4—C5—C9	−175.5 (3)	C23—C24—C25—C29	−174.4 (3)
C7—C4—C5—C9	1.4 (4)	C27—C24—C25—C29	0.9 (5)
C4—C5—C6—C1	−1.2 (4)	C22—C21—C26—C25	1.1 (5)
C9—C5—C6—C1	174.3 (3)	C22—C21—C26—C31	−178.4 (3)
C4—C5—C6—C11	179.4 (3)	C24—C25—C26—C21	−2.3 (5)
C9—C5—C6—C11	−5.1 (4)	C29—C25—C26—C21	173.5 (3)
C2—C1—C6—C5	1.7 (5)	C24—C25—C26—C31	177.1 (3)
C2—C1—C6—C11	−178.9 (3)	C29—C25—C26—C31	−7.0 (4)
C8—O2—C7—O1	−3.9 (5)	C28—O9—C27—O10	−1.6 (5)
C8—O2—C7—C4	176.6 (3)	C28—O9—C27—C24	177.0 (3)
C3—C4—C7—O1	174.1 (3)	C23—C24—C27—O10	154.8 (4)
C5—C4—C7—O1	−2.7 (5)	C25—C24—C27—O10	−20.3 (5)
C3—C4—C7—O2	−6.4 (4)	C23—C24—C27—O9	−23.7 (4)
C5—C4—C7—O2	176.8 (3)	C25—C24—C27—O9	161.1 (3)
C10—O4—C9—O3	−0.5 (5)	C30—O12—C29—O11	−5.0 (5)
C10—O4—C9—C5	−175.4 (3)	C30—O12—C29—C25	177.5 (3)
C6—C5—C9—O3	−76.6 (4)	C24—C25—C29—O11	107.1 (4)
C4—C5—C9—O3	98.8 (4)	C26—C25—C29—O11	−68.8 (4)
C6—C5—C9—O4	98.6 (3)	C24—C25—C29—O12	−75.4 (4)
C4—C5—C9—O4	−86.0 (4)	C26—C25—C29—O12	108.7 (3)
C5—C6—C11—C16	117.0 (3)	C21—C26—C31—C36	119.8 (4)
C1—C6—C11—C16	−62.4 (4)	C25—C26—C31—C36	−59.6 (4)
C5—C6—C11—C12	−63.0 (4)	C21—C26—C31—C32	−60.2 (4)
C1—C6—C11—C12	117.6 (4)	C25—C26—C31—C32	120.3 (4)
C16—C11—C12—C13	−1.1 (5)	C36—C31—C32—C33	1.8 (5)
C6—C11—C12—C13	178.9 (3)	C26—C31—C32—C33	−178.1 (3)
C11—C12—C13—C14	0.7 (5)	C31—C32—C33—C34	−2.7 (5)
C12—C13—C14—C15	−0.8 (5)	C31—C32—C33—C37	175.6 (3)
C12—C13—C14—C19	176.7 (3)	C32—C33—C34—C35	2.0 (5)
C13—C14—C15—C16	1.4 (5)	C37—C33—C34—C35	−176.1 (3)
C19—C14—C15—C16	−176.1 (3)	C32—C33—C34—C39	−175.6 (3)
C13—C14—C15—C17	−175.5 (3)	C37—C33—C34—C39	6.2 (5)
C19—C14—C15—C17	7.0 (5)	C33—C34—C35—C36	−0.5 (5)
C14—C15—C16—C11	−1.9 (5)	C39—C34—C35—C36	177.1 (3)
C17—C15—C16—C11	175.1 (3)	C34—C35—C36—C31	−0.3 (6)
C12—C11—C16—C15	1.7 (5)	C32—C31—C36—C35	−0.3 (5)
C6—C11—C16—C15	−178.3 (3)	C26—C31—C36—C35	179.6 (3)
C18—O5—C17—O6	10.4 (5)	C38—O13—C37—O14	9.6 (6)
C18—O5—C17—C15	−174.3 (3)	C38—O13—C37—C33	−174.8 (3)
C16—C15—C17—O6	68.0 (5)	C32—C33—C37—O14	60.3 (5)
C14—C15—C17—O6	−115.2 (4)	C34—C33—C37—O14	−121.5 (4)
C16—C15—C17—O5	−107.3 (4)	C32—C33—C37—O13	−115.2 (4)
C14—C15—C17—O5	69.6 (4)	C34—C33—C37—O13	63.0 (4)
C20—O8—C19—O7	0.3 (5)	C40—O16—C39—O15	0.1 (6)
C20—O8—C19—C14	−177.9 (3)	C40—O16—C39—C34	−178.0 (3)
C13—C14—C19—O7	−163.5 (4)	C35—C34—C39—O15	−159.6 (4)
C15—C14—C19—O7	13.9 (5)	C33—C34—C39—O15	17.9 (6)
C13—C14—C19—O8	14.6 (5)	C35—C34—C39—O16	18.5 (5)
C15—C14—C19—O8	−168.0 (3)	C33—C34—C39—O16	−163.9 (3)