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Acta Cryst. (2008). E64, o1779    [ doi:10.1107/S1600536808025762 ]

Tetramethyl biphenyl-2,3,3',4'-tetracarboxylate

G. Gao, X. Ma, Y. Jiang, W. Chen and J. Men

Abstract top

The asymmetric unit of the title compound, C20H18O8, contains two molecules 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.

Comment top

The title compound is a useful chemical intermediate for the further preparation of various compounds, including, for example, acid, the salts, acyl halides, amides, imides, and the like (Ding et al., 1992). Polymides are well known for possessing excellent thermal and oxidative stability, as well as excellent mechanical properties (Ghosh & Mittal, 1996). The 2,3,3',4'-biphenyltetracarboxylic dianhydride was suggested as a monomer for the synthesis of soluble polyimides with high chemical and thermal stability (Rozhanskii et al., 2000).

The asymmetric unit of I contains two crystallographically independent molecules (molecule 1 - C1–C18 and molecule 2 - C19–C38) (Fig. 1). For the molecule 1, the dihedral angle between the two phenyl rings are 62.94 (12)° while in the molecule 2 is 59.99 (12)° and they are both markedly differ from 42.30 (11)° in the 1,1'-biphenyl-2,3,3',4'–etracarboxylic acid monohydrate (Jiang et al., 2008). For the molecule 1, the dihedral angles of the two carboxyl groups placed in 2,3-positions are 81.72 (13)° and another two carboxyl groups placed in 3',4'-positions are 67.24 (15)°; for the molecule 2, which are 65.54 (15)° and 59.98 (17)° respectively. Torsion angles C7—C4—C5—C9 and C27—C24—C25—C29 are 1.4 (4)° and 0.9 (4)°, respectively. However, torsion angles C19—C14—C15—C17 and C39—C34—C33—C37 are 7.0 (5)° and 6.2 (5)°, respectively. They are markedly smaller than those for the parent phthalic acid 20.3° (Ermer, 1981).

Related literature top

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

Experimental top

2,3,3',4'-biphenyltetracarboxylic dianhydride (29.4 g, 0.1 mol) and p-toluenesulfonic acid (2.0 g, 0.01 mol) was dissolved in a solution of toluene (100 ml) and methanol (50 ml) in a three-necked flask equipped with a Dean–Stark trap. The mixture was heated to reflux. After 20 h, water and most of the methanol were removed by azeotropic distillation with toluene. The mixture was allowed to cool and was added subsequently 500 ml of H2O. The organic phase was washed three times with saturated Na2CO3 and three times with water. Toluene was removed on a rotary evaporator and the residue was recrystallized in EtOH to afford white powder (34.7 g, 90% yield). Single crystals were grown by slow evaporation of a toluene of solution over a period of several days, m.p.382–384 K.

Refinement top

H atoms were positioned geometrically (C—H = 0.93–0.96Å) and refined using a riding model with the Uiso(H) = 1.2UeqC (for aromatic) and Uiso(H) = 1.5UeqC (for methyl).

Computing details top

Data collection: DIFRAC (Gabe & White, 1993); cell refinement: DIFRAC (Gabe & White, 1993); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of I with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
Tetramethyl biphenyl-2,3,3',4'-tetracarboxylate top
Crystal data top
C20H18O8F000 = 1616
Mr = 386.34Dx = 1.330 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 31 reflections
a = 14.395 (4) Åθ = 4.7–9.2º
b = 13.453 (4) ŵ = 0.10 mm−1
c = 21.013 (3) ÅT = 297 (2) K
β = 108.45 (4)ºBlock, colourless
V = 3860.1 (19) Å30.45 × 0.42 × 0.38 mm
Z = 8
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.006
Radiation source: fine-focus sealed tubeθmax = 25.3º
Monochromator: graphiteθmin = 1.8º
T = 297(2) Kh = −17→16
ω/2θ scansk = 0→16
Absorption correction: nonel = −14→25
8168 measured reflections3 standard reflections
6906 independent reflections every 300 reflections
2997 reflections with I > 2σ(I) intensity decay: 1.8%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059H-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 reflectionsΔρmax = 0.28 e Å−3
515 parametersΔρmin = −0.23 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C20H18O8V = 3860.1 (19) Å3
Mr = 386.34Z = 8
Monoclinic, P21/nMo Kα
a = 14.395 (4) ŵ = 0.10 mm−1
b = 13.453 (4) ÅT = 297 (2) K
c = 21.013 (3) Å0.45 × 0.42 × 0.38 mm
β = 108.45 (4)º
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.006
Absorption correction: none3 standard reflections
8168 measured reflections every 300 reflections
6906 independent reflections intensity decay: 1.8%
2997 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.059515 parameters
wR(F2) = 0.163H-atom parameters constrained
S = 1.04Δρmax = 0.28 e Å−3
6906 reflectionsΔρmin = −0.23 e Å−3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.58582 (18)0.6473 (2)0.10659 (14)0.0722 (8)
O20.66768 (17)0.78792 (19)0.13706 (13)0.0628 (7)
O30.37936 (18)0.57886 (17)0.11045 (13)0.0602 (7)
O40.38789 (17)0.62465 (17)0.00901 (12)0.0582 (7)
O50.02260 (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)
C10.3321 (3)0.9024 (2)0.11080 (17)0.0492 (9)
H10.27730.93890.11100.059*
C20.4233 (3)0.9456 (3)0.13244 (17)0.0510 (9)
H20.42971.01140.14670.061*
C30.5055 (2)0.8924 (2)0.13322 (16)0.0463 (9)
H30.56670.92270.14750.056*
C40.4974 (2)0.7938 (2)0.11289 (15)0.0389 (8)
C50.4049 (2)0.7492 (2)0.09027 (14)0.0363 (8)
C60.3216 (2)0.8033 (2)0.08845 (15)0.0412 (8)
C70.5861 (2)0.7338 (3)0.11817 (16)0.0454 (9)
C80.7599 (3)0.7343 (3)0.1475 (2)0.0779 (13)
H8A0.76600.68310.18040.117*
H8B0.81370.77980.16290.117*
H8C0.76030.70490.10590.117*
C90.3917 (2)0.6403 (3)0.07216 (18)0.0431 (8)
C100.3676 (3)0.5227 (3)−0.0148 (2)0.0868 (14)
H10A0.40820.47800.01790.130*
H10B0.38110.5153−0.05640.130*
H10C0.29990.5076−0.02150.130*
C110.2216 (2)0.7587 (2)0.06406 (16)0.0400 (8)
C120.1815 (3)0.7259 (3)−0.00211 (16)0.0503 (9)
H120.21710.7329−0.03190.060*
C130.0899 (2)0.6834 (3)−0.02369 (17)0.0506 (9)
H130.06470.6613−0.06780.061*
C140.0347 (2)0.6729 (2)0.01933 (16)0.0431 (8)
C150.0746 (2)0.7055 (2)0.08603 (16)0.0408 (8)
C160.1658 (2)0.7487 (2)0.10680 (15)0.0421 (8)
H160.19070.77180.15060.051*
C170.0229 (3)0.6902 (3)0.13731 (18)0.0508 (9)
C18−0.0328 (3)0.5667 (3)0.1968 (2)0.0904 (15)
H18A−0.03850.62290.22340.136*
H18B0.00050.51380.22570.136*
H18C−0.09690.54480.17040.136*
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−0.18940.4880−0.06980.127*
H20B−0.19530.5356−0.13910.127*
H20C−0.23010.5961−0.08700.127*
O90.90819 (19)0.3219 (2)0.20321 (13)0.0730 (8)
O100.8394 (2)0.1751 (2)0.19739 (18)0.0968 (11)
O110.62367 (18)0.09734 (17)0.17382 (12)0.0558 (7)
O120.6628 (2)0.15331 (17)0.08491 (12)0.0649 (7)
O130.2462 (2)0.0867 (2)0.19228 (14)0.0765 (8)
O140.2231 (2)0.2456 (2)0.21508 (15)0.0870 (10)
O150.1182 (2)0.1385 (2)0.06290 (15)0.0838 (9)
O160.17875 (19)0.0866 (2)−0.01709 (14)0.0790 (8)
C210.5672 (3)0.4153 (3)0.18722 (18)0.0582 (10)
H210.51000.44840.18630.070*
C220.6571 (3)0.4616 (3)0.21457 (18)0.0625 (11)
H220.65980.52510.23250.075*
C230.7419 (3)0.4149 (3)0.21548 (17)0.0542 (10)
H230.80140.44780.23280.065*
C240.7401 (2)0.3184 (2)0.19076 (16)0.0446 (9)
C250.6495 (2)0.2707 (2)0.16425 (15)0.0416 (8)
C260.5620 (2)0.3192 (2)0.16103 (15)0.0442 (8)
C270.8319 (3)0.2630 (3)0.19680 (17)0.0506 (9)
C281.0022 (3)0.2714 (4)0.2128 (2)0.0868 (14)
H28A1.01810.23150.25270.130*
H28B1.05260.32010.21720.130*
H28C0.99730.22970.17480.130*
C290.6447 (2)0.1636 (2)0.14292 (17)0.0413 (8)
C300.6633 (4)0.0514 (3)0.0632 (2)0.1001 (17)
H30A0.70300.01190.09970.150*
H30B0.68960.04860.02650.150*
H30C0.59750.02610.04880.150*
C310.4657 (2)0.2706 (2)0.13009 (17)0.0448 (8)
C320.4016 (3)0.2537 (3)0.16732 (17)0.0513 (9)
H320.41920.27510.21160.062*
C330.3130 (3)0.2060 (3)0.13961 (17)0.0478 (9)
C340.2835 (2)0.1771 (3)0.07211 (17)0.0484 (9)
C350.3463 (3)0.1945 (3)0.03489 (17)0.0548 (10)
H350.32780.1752−0.00990.066*
C360.4362 (3)0.2404 (3)0.06343 (17)0.0546 (10)
H360.47720.25100.03770.066*
C370.2537 (3)0.1852 (3)0.1855 (2)0.0604 (10)
C380.1830 (4)0.0548 (4)0.2310 (3)0.1100 (18)
H38A0.19680.09410.27110.165*
H38B0.1951−0.01400.24290.165*
H38C0.11560.06340.20450.165*
C390.1845 (3)0.1319 (3)0.0402 (2)0.0579 (10)
C400.0844 (3)0.0424 (4)−0.0540 (2)0.1078 (17)
H40A0.0676−0.0072−0.02670.162*
H40B0.08860.0122−0.09440.162*
H40C0.03490.0931−0.06520.162*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0541 (17)0.0528 (18)0.107 (2)0.0050 (14)0.0223 (15)−0.0148 (16)
O20.0398 (16)0.0647 (18)0.0844 (19)−0.0051 (14)0.0202 (14)−0.0119 (14)
O30.0691 (18)0.0385 (15)0.0755 (18)−0.0081 (13)0.0263 (15)0.0061 (13)
O40.0716 (18)0.0473 (15)0.0569 (15)−0.0036 (13)0.0221 (13)−0.0166 (12)
O50.0744 (19)0.0595 (18)0.0815 (19)0.0036 (14)0.0446 (15)0.0158 (14)
O60.079 (2)0.0711 (19)0.0828 (19)0.0027 (16)0.0499 (17)−0.0061 (16)
O70.0496 (17)0.117 (3)0.086 (2)−0.0181 (17)0.0287 (16)−0.0200 (18)
O80.0518 (17)0.0757 (19)0.0743 (19)−0.0166 (14)0.0123 (14)−0.0197 (15)
C10.048 (2)0.037 (2)0.065 (2)0.0078 (18)0.0200 (19)−0.0003 (18)
C20.052 (2)0.035 (2)0.065 (2)−0.0052 (19)0.0175 (19)−0.0066 (17)
C30.041 (2)0.045 (2)0.050 (2)−0.0102 (18)0.0102 (17)−0.0029 (17)
C40.041 (2)0.037 (2)0.0397 (18)−0.0047 (17)0.0139 (16)−0.0010 (15)
C50.040 (2)0.0340 (19)0.0376 (17)−0.0015 (16)0.0159 (15)−0.0031 (14)
C60.043 (2)0.040 (2)0.0428 (19)−0.0040 (17)0.0162 (16)−0.0021 (16)
C70.039 (2)0.051 (2)0.046 (2)−0.006 (2)0.0132 (17)−0.0085 (18)
C80.042 (2)0.097 (3)0.097 (3)0.003 (2)0.025 (2)−0.009 (3)
C90.036 (2)0.038 (2)0.053 (2)−0.0046 (16)0.0122 (17)−0.0080 (18)
C100.108 (4)0.054 (3)0.099 (3)−0.012 (2)0.032 (3)−0.040 (2)
C110.0333 (19)0.041 (2)0.046 (2)0.0034 (16)0.0129 (16)0.0048 (16)
C120.049 (2)0.063 (2)0.045 (2)−0.005 (2)0.0236 (18)0.0031 (18)
C130.044 (2)0.063 (2)0.043 (2)−0.0078 (19)0.0101 (17)−0.0032 (18)
C140.038 (2)0.043 (2)0.049 (2)0.0002 (17)0.0156 (17)0.0048 (16)
C150.035 (2)0.043 (2)0.047 (2)0.0055 (17)0.0177 (16)0.0065 (16)
C160.042 (2)0.047 (2)0.0380 (18)0.0012 (17)0.0128 (16)−0.0007 (16)
C170.043 (2)0.056 (3)0.055 (2)−0.0043 (19)0.0188 (18)0.006 (2)
C180.099 (4)0.091 (3)0.102 (3)−0.012 (3)0.061 (3)0.027 (3)
C190.041 (2)0.057 (2)0.056 (2)−0.0014 (19)0.0112 (19)0.004 (2)
C200.057 (3)0.083 (3)0.097 (3)−0.016 (2)−0.001 (2)−0.015 (3)
O90.0493 (17)0.0671 (18)0.105 (2)−0.0108 (15)0.0274 (15)−0.0144 (16)
O100.068 (2)0.0443 (19)0.179 (3)0.0064 (15)0.040 (2)0.0258 (19)
O110.0757 (18)0.0373 (14)0.0639 (16)−0.0082 (13)0.0355 (14)0.0004 (12)
O120.107 (2)0.0389 (15)0.0671 (17)0.0001 (14)0.0528 (16)−0.0036 (12)
O130.083 (2)0.073 (2)0.086 (2)0.0099 (16)0.0456 (17)0.0200 (16)
O140.089 (2)0.089 (2)0.106 (2)0.0118 (18)0.064 (2)−0.0156 (19)
O150.0512 (18)0.110 (3)0.092 (2)−0.0072 (17)0.0262 (16)0.0036 (18)
O160.0606 (19)0.092 (2)0.076 (2)−0.0128 (16)0.0102 (15)−0.0203 (17)
C210.063 (3)0.045 (2)0.064 (2)0.016 (2)0.017 (2)−0.0009 (19)
C220.078 (3)0.037 (2)0.066 (3)0.003 (2)0.014 (2)−0.0107 (18)
C230.063 (3)0.040 (2)0.054 (2)−0.014 (2)0.0111 (19)0.0025 (18)
C240.051 (2)0.035 (2)0.047 (2)−0.0040 (18)0.0135 (17)0.0053 (16)
C250.051 (2)0.0314 (19)0.0431 (19)0.0020 (17)0.0155 (17)0.0035 (15)
C260.047 (2)0.040 (2)0.046 (2)0.0035 (18)0.0131 (17)0.0028 (16)
C270.045 (2)0.052 (3)0.052 (2)−0.003 (2)0.0130 (18)0.0053 (18)
C280.052 (3)0.110 (4)0.104 (4)−0.005 (3)0.033 (3)−0.019 (3)
C290.045 (2)0.038 (2)0.044 (2)−0.0016 (17)0.0178 (17)−0.0008 (17)
C300.186 (6)0.047 (3)0.099 (3)−0.003 (3)0.090 (4)−0.020 (2)
C310.043 (2)0.040 (2)0.050 (2)0.0068 (17)0.0127 (18)0.0003 (16)
C320.053 (2)0.053 (2)0.048 (2)0.018 (2)0.0161 (19)0.0037 (18)
C330.045 (2)0.046 (2)0.053 (2)0.0133 (18)0.0156 (18)0.0049 (17)
C340.037 (2)0.050 (2)0.058 (2)0.0106 (18)0.0142 (19)0.0061 (18)
C350.053 (2)0.067 (3)0.040 (2)0.006 (2)0.0094 (19)0.0007 (18)
C360.053 (2)0.062 (2)0.050 (2)−0.004 (2)0.0187 (19)−0.0010 (19)
C370.049 (2)0.070 (3)0.064 (3)0.009 (2)0.021 (2)0.006 (2)
C380.131 (4)0.105 (4)0.122 (4)−0.001 (3)0.080 (4)0.032 (3)
C390.051 (3)0.058 (3)0.060 (3)0.008 (2)0.011 (2)0.012 (2)
C400.078 (4)0.123 (4)0.106 (4)−0.041 (3)0.004 (3)−0.026 (3)
Geometric parameters (Å, °) top
O1—C71.188 (4)O9—C271.326 (4)
O2—C71.331 (4)O9—C281.469 (4)
O2—C81.465 (4)O10—C271.188 (4)
O3—C91.205 (4)O11—C291.197 (4)
O4—C91.328 (4)O12—C291.331 (4)
O4—C101.457 (4)O12—C301.446 (4)
O5—C171.323 (4)O13—C371.340 (4)
O5—C181.452 (4)O13—C381.465 (4)
O6—C171.206 (4)O14—C371.190 (4)
O7—C191.209 (4)O15—C391.198 (4)
O8—C191.320 (4)O16—C391.328 (4)
O8—C201.454 (4)O16—C401.461 (5)
C1—C21.375 (5)C21—C221.386 (5)
C1—C61.406 (4)C21—C261.399 (4)
C1—H10.9300C21—H210.9300
C2—C31.379 (4)C22—C231.367 (5)
C2—H20.9300C22—H220.9300
C3—C41.386 (4)C23—C241.396 (4)
C3—H30.9300C23—H230.9300
C4—C51.399 (4)C24—C251.401 (4)
C4—C71.485 (4)C24—C271.487 (5)
C5—C61.394 (4)C25—C261.401 (4)
C5—C91.510 (4)C25—C291.504 (4)
C6—C111.492 (4)C26—C311.484 (5)
C8—H8A0.9600C28—H28A0.9600
C8—H8B0.9600C28—H28B0.9600
C8—H8C0.9600C28—H28C0.9600
C10—H10A0.9600C30—H30A0.9600
C10—H10B0.9600C30—H30B0.9600
C10—H10C0.9600C30—H30C0.9600
C11—C161.389 (4)C31—C361.390 (4)
C11—C121.398 (4)C31—C321.404 (4)
C12—C131.376 (4)C32—C331.381 (5)
C12—H120.9300C32—H320.9300
C13—C141.387 (4)C33—C341.401 (5)
C13—H130.9300C33—C371.502 (5)
C14—C151.406 (4)C34—C351.391 (5)
C14—C191.481 (5)C34—C391.497 (5)
C15—C161.373 (4)C35—C361.386 (5)
C15—C171.506 (4)C35—H350.9300
C16—H160.9300C36—H360.9300
C18—H18A0.9600C38—H38A0.9600
C18—H18B0.9600C38—H38B0.9600
C18—H18C0.9600C38—H38C0.9600
C20—H20A0.9600C40—H40A0.9600
C20—H20B0.9600C40—H40B0.9600
C20—H20C0.9600C40—H40C0.9600
C7—O2—C8116.6 (3)C27—O9—C28115.8 (3)
C9—O4—C10115.6 (3)C29—O12—C30114.2 (3)
C17—O5—C18117.0 (3)C37—O13—C38115.8 (3)
C19—O8—C20116.2 (3)C39—O16—C40116.7 (3)
C2—C1—C6120.1 (3)C22—C21—C26120.3 (4)
C2—C1—H1119.9C22—C21—H21119.9
C6—C1—H1119.9C26—C21—H21119.9
C1—C2—C3120.7 (3)C23—C22—C21120.8 (4)
C1—C2—H2119.6C23—C22—H22119.6
C3—C2—H2119.6C21—C22—H22119.6
C2—C3—C4120.3 (3)C22—C23—C24120.7 (4)
C2—C3—H3119.9C22—C23—H23119.6
C4—C3—H3119.9C24—C23—H23119.6
C3—C4—C5119.6 (3)C23—C24—C25118.7 (3)
C3—C4—C7120.7 (3)C23—C24—C27121.5 (3)
C5—C4—C7119.6 (3)C25—C24—C27119.6 (3)
C6—C5—C4120.2 (3)C24—C25—C26121.0 (3)
C6—C5—C9117.4 (3)C24—C25—C29120.4 (3)
C4—C5—C9122.2 (3)C26—C25—C29118.4 (3)
C5—C6—C1119.1 (3)C21—C26—C25118.5 (3)
C5—C6—C11121.8 (3)C21—C26—C31120.4 (3)
C1—C6—C11119.1 (3)C25—C26—C31121.1 (3)
O1—C7—O2122.8 (3)O10—C27—O9121.6 (4)
O1—C7—C4124.8 (3)O10—C27—C24125.2 (4)
O2—C7—C4112.4 (3)O9—C27—C24113.3 (3)
O2—C8—H8A109.5O9—C28—H28A109.5
O2—C8—H8B109.5O9—C28—H28B109.5
H8A—C8—H8B109.5H28A—C28—H28B109.5
O2—C8—H8C109.5O9—C28—H28C109.5
H8A—C8—H8C109.5H28A—C28—H28C109.5
H8B—C8—H8C109.5H28B—C28—H28C109.5
O3—C9—O4126.2 (3)O11—C29—O12125.2 (3)
O3—C9—C5122.1 (3)O11—C29—C25123.2 (3)
O4—C9—C5111.6 (3)O12—C29—C25111.6 (3)
O4—C10—H10A109.5O12—C30—H30A109.5
O4—C10—H10B109.5O12—C30—H30B109.5
H10A—C10—H10B109.5H30A—C30—H30B109.5
O4—C10—H10C109.5O12—C30—H30C109.5
H10A—C10—H10C109.5H30A—C30—H30C109.5
H10B—C10—H10C109.5H30B—C30—H30C109.5
C16—C11—C12118.1 (3)C36—C31—C32118.0 (3)
C16—C11—C6120.6 (3)C36—C31—C26121.1 (3)
C12—C11—C6121.2 (3)C32—C31—C26121.0 (3)
C13—C12—C11120.7 (3)C33—C32—C31121.5 (3)
C13—C12—H12119.7C33—C32—H32119.3
C11—C12—H12119.7C31—C32—H32119.3
C12—C13—C14121.0 (3)C32—C33—C34120.0 (3)
C12—C13—H13119.5C32—C33—C37116.9 (3)
C14—C13—H13119.5C34—C33—C37123.1 (3)
C13—C14—C15118.6 (3)C35—C34—C33118.6 (3)
C13—C14—C19121.5 (3)C35—C34—C39120.8 (3)
C15—C14—C19119.8 (3)C33—C34—C39120.5 (3)
C16—C15—C14119.8 (3)C36—C35—C34121.1 (3)
C16—C15—C17118.0 (3)C36—C35—H35119.5
C14—C15—C17122.1 (3)C34—C35—H35119.5
C15—C16—C11121.7 (3)C35—C36—C31120.8 (3)
C15—C16—H16119.1C35—C36—H36119.6
C11—C16—H16119.1C31—C36—H36119.6
O6—C17—O5124.2 (3)O14—C37—O13124.3 (4)
O6—C17—C15125.3 (3)O14—C37—C33126.0 (4)
O5—C17—C15110.3 (3)O13—C37—C33109.5 (3)
O5—C18—H18A109.5O13—C38—H38A109.5
O5—C18—H18B109.5O13—C38—H38B109.5
H18A—C18—H18B109.5H38A—C38—H38B109.5
O5—C18—H18C109.5O13—C38—H38C109.5
H18A—C18—H18C109.5H38A—C38—H38C109.5
H18B—C18—H18C109.5H38B—C38—H38C109.5
O7—C19—O8124.1 (3)O15—C39—O16124.4 (4)
O7—C19—C14124.3 (4)O15—C39—C34123.8 (4)
O8—C19—C14111.6 (3)O16—C39—C34111.8 (3)
O8—C20—H20A109.5O16—C40—H40A109.5
O8—C20—H20B109.5O16—C40—H40B109.5
H20A—C20—H20B109.5H40A—C40—H40B109.5
O8—C20—H20C109.5O16—C40—H40C109.5
H20A—C20—H20C109.5H40A—C40—H40C109.5
H20B—C20—H20C109.5H40B—C40—H40C109.5
C6—C1—C2—C3−0.7 (5)C26—C21—C22—C231.1 (6)
C1—C2—C3—C4−0.8 (5)C21—C22—C23—C24−2.0 (5)
C2—C3—C4—C51.3 (5)C22—C23—C24—C250.7 (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—C261.5 (5)
C7—C4—C5—C6176.6 (3)C27—C24—C25—C26176.7 (3)
C3—C4—C5—C9−175.5 (3)C23—C24—C25—C29−174.4 (3)
C7—C4—C5—C91.4 (4)C27—C24—C25—C290.9 (5)
C4—C5—C6—C1−1.2 (4)C22—C21—C26—C251.1 (5)
C9—C5—C6—C1174.3 (3)C22—C21—C26—C31−178.4 (3)
C4—C5—C6—C11179.4 (3)C24—C25—C26—C21−2.3 (5)
C9—C5—C6—C11−5.1 (4)C29—C25—C26—C21173.5 (3)
C2—C1—C6—C51.7 (5)C24—C25—C26—C31177.1 (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—C4176.6 (3)C28—O9—C27—C24177.0 (3)
C3—C4—C7—O1174.1 (3)C23—C24—C27—O10154.8 (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—O2176.8 (3)C25—C24—C27—O9161.1 (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—C25177.5 (3)
C6—C5—C9—O3−76.6 (4)C24—C25—C29—O11107.1 (4)
C4—C5—C9—O398.8 (4)C26—C25—C29—O11−68.8 (4)
C6—C5—C9—O498.6 (3)C24—C25—C29—O12−75.4 (4)
C4—C5—C9—O4−86.0 (4)C26—C25—C29—O12108.7 (3)
C5—C6—C11—C16117.0 (3)C21—C26—C31—C36119.8 (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—C12117.6 (4)C25—C26—C31—C32120.3 (4)
C16—C11—C12—C13−1.1 (5)C36—C31—C32—C331.8 (5)
C6—C11—C12—C13178.9 (3)C26—C31—C32—C33−178.1 (3)
C11—C12—C13—C140.7 (5)C31—C32—C33—C34−2.7 (5)
C12—C13—C14—C15−0.8 (5)C31—C32—C33—C37175.6 (3)
C12—C13—C14—C19176.7 (3)C32—C33—C34—C352.0 (5)
C13—C14—C15—C161.4 (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—C396.2 (5)
C19—C14—C15—C177.0 (5)C33—C34—C35—C36−0.5 (5)
C14—C15—C16—C11−1.9 (5)C39—C34—C35—C36177.1 (3)
C17—C15—C16—C11175.1 (3)C34—C35—C36—C31−0.3 (6)
C12—C11—C16—C151.7 (5)C32—C31—C36—C35−0.3 (5)
C6—C11—C16—C15−178.3 (3)C26—C31—C36—C35179.6 (3)
C18—O5—C17—O610.4 (5)C38—O13—C37—O149.6 (6)
C18—O5—C17—C15−174.3 (3)C38—O13—C37—C33−174.8 (3)
C16—C15—C17—O668.0 (5)C32—C33—C37—O1460.3 (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—O569.6 (4)C34—C33—C37—O1363.0 (4)
C20—O8—C19—O70.3 (5)C40—O16—C39—O150.1 (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—O713.9 (5)C33—C34—C39—O1517.9 (6)
C13—C14—C19—O814.6 (5)C35—C34—C39—O1618.5 (5)
C15—C14—C19—O8−168.0 (3)C33—C34—C39—O16−163.9 (3)
Acknowledgements top

The authors are grateful to the National Undergraduates' Innovative Experiment Project of China and the Undergraduates' Innovative Experiment Project of Sichuan University for financial support. We thank Mr Zhi-Hua Mao of Sichuan University for the X-ray data collection.

references
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