(1R,7R)-4-[(1R,2S,5R)-2-Iso­propyl-5-methyl­cyclo­hex­oxy]-9,9-di­methyl-2,2,6,6-tetra­phenyl-3,5,8,10-tetraoxa-4-phosphabi­cyclo[5.3.0]­decane

The crystal structure of the title compound, C₄₁H₄₇PO₅, has been determined. The absolute configuration assignment was based on knowledge of the chirality of the starting material.

Key indicators

• Single-crystal X-ray study
• T = 133 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.038
• wR factor = 0.039
• Data-to-parameter ratio = 7.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



REFNR_01  Alert C Ratio of reflections to parameters is < 8 for a
          non-centrosymmetric structure, where ZMAX < 18
          sine(theta)/lambda                0.5882
          Proportion of unique data used    0.5388
          Ratio reflections to parameters   7.4481

THETM_01  Alert C The value of sine(theta_max)/wavelength is less than 0.590
          Calculated sin(theta_max)/wavelength =    0.5882

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           24.71
         From the CIF: _reflns_number_total               5861
         Count of symmetry unique reflns         3456
         Completeness (_total/calc)            169.59%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      2405
         Fraction of Friedel pairs measured     0.696
         Are heavy atom types Z>Si present          yes
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

---

S1. Comment

Phosphorus-containing compounds are widely used as non-reactive ligands in metal catalysts. The title compound, (I), has been shown to induce enantioselectivity in Cu-mediated conjugate addition. This compound is also of interest as a ligand for Rh(I)-catalysed C—H bond activation. The bulky chiral phosphite is expected to induce enantioselectivity in the addition of C—H bonds across imine pi-bonds.

The title compound contains a seven-membered heterocyclic backbone comprised of TADDOL (TADDOL = α,α,α',α'-tetraphenyl-2,2'-dimethyl-1,3-dioxolane-4,5-dimethanol) and phosphorous, the third substituent on phosphorous being a menthol bonded through oxygen. Bond lengths and angles are typical for organophosphites, and the structure of the TADDOL-phosphorous ring is similar to that of previously reported compounds (Keller et al., 1998 and Sakaki et al., 1993). In these past examples, the third substituent on phosphorous has been relatively small and achiral (dimethylamine and phenyl, respectively). In the title compound, the larger chiral menthol provides an additional point of asymmetry, and is expected to increase the enantioselectivity of reactions carried out using metal complexes of this ligand.

S2. Experimental

The title compound was prepared by the stepwise reaction of (+)-menthol and (-)-TADDOL with phosphorous trichloride according to a literature procedure (Alexakis et al., 2000). X-ray quality crystals were obtained by slowly cooling a concentrated solution of the title compound in an ether/pentane mixture to 238 K.

Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare, 1993); program(s) used to refine structure: TEXSAN (Molecular Structure Corporation, 1985, 1992); molecular graphics: please provide; software used to prepare material for publication: TEXSAN.

Figures

Fig. 1. The title compound, with displacement parameters drawn at the 50% probability level. Hydrogen atoms are omitted for clarity.

(I)

Crystal data

C41H47O5P	Dx = 1.209 Mg m^−3
Mr = 650.79	Mo Kα radiation, λ = 0.7107 Å
Orthorhombic, P212121	Cell parameters from 4403 reflections
a = 17.884 (1) Å	θ = 2.3–22.4°
b = 8.9233 (6) Å	µ = 0.12 mm^−1
c = 22.395 (2) Å	T = 133 K
V = 3574.0 (4) Å^3	Column, colorless
Z = 4	0.27 × 0.20 × 0.09 mm
F(000) = 1392.00

Data collection

SMART 1K CCD diffractometer	5861 independent reflections
Radiation source: X-ray tube	3158 reflections with I > 3.00σ(I)
Graphite monochromator	Rint = 0.069
ω–scan	θmax = 24.7°
Absorption correction: multi-scan (Blessing, 1995)	h = −21→20
Tmin = 0.967, Tmax = 0.989	k = −9→10
15797 measured reflections	l = −22→26

Refinement

Refinement on F	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.038	Weighting scheme based on measured s.u.'s Please provide expression for w
wR(F^2) = 0.039	(Δ/σ)max = 0.001
S = 0.96	Δρmax = 0.21 e Å^−3
3158 reflections	Δρmin = −0.32 e Å^−3
424 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
P(1)	0.10922 (6)	0.2157 (1)	1.01543 (5)	0.0188
O(1)	0.0815 (2)	0.1010 (3)	1.0663 (1)	0.0200
O(2)	0.0284 (1)	0.2191 (3)	0.9818 (1)	0.0174
O(3)	0.1526 (2)	0.0885 (3)	0.9742 (1)	0.0191
O(4)	0.0662 (2)	0.3920 (3)	0.8362 (1)	0.0212
O(5)	0.1294 (2)	0.1764 (3)	0.8153 (1)	0.0165
C(1)	0.1229 (2)	0.0993 (5)	1.1230 (2)	0.0222
C(2)	0.0861 (3)	0.2122 (6)	1.1649 (2)	0.0279
C(3)	0.1189 (2)	0.2075 (6)	1.2281 (2)	0.0294
C(4)	0.1150 (3)	0.0470 (5)	1.2521 (2)	0.0289
C(5)	0.1534 (3)	−0.0649 (5)	1.2096 (2)	0.0333
C(6)	0.1201 (3)	−0.0611 (5)	1.1464 (2)	0.0250
C(7)	0.0806 (3)	0.3172 (6)	1.2691 (2)	0.0397
C(8)	0.1559 (3)	−0.1768 (5)	1.1042 (2)	0.0338
C(9)	0.1370 (3)	−0.3383 (6)	1.1222 (2)	0.0535
C(10)	0.2395 (3)	−0.1583 (6)	1.0965 (2)	0.0396
C(11)	0.0141 (2)	0.3283 (4)	0.9346 (2)	0.0188
C(12)	0.0027 (2)	0.4834 (5)	0.9636 (2)	0.0215
C(13)	−0.0421 (3)	0.4938 (5)	1.0149 (2)	0.0310
C(14)	−0.0538 (3)	0.6310 (6)	1.0419 (2)	0.0329
C(15)	−0.0211 (3)	0.7602 (5)	1.0188 (2)	0.0315
C(16)	0.0235 (3)	0.7497 (5)	0.9689 (2)	0.0343
C(17)	0.0351 (3)	0.6118 (5)	0.9409 (2)	0.0219
C(18)	−0.0576 (2)	0.2759 (5)	0.9045 (2)	0.0186
C(19)	−0.0989 (3)	0.3727 (5)	0.8693 (2)	0.0351
C(20)	−0.1641 (3)	0.3242 (6)	0.8407 (2)	0.0322
C(21)	−0.1874 (3)	0.1792 (6)	0.8483 (2)	0.0388
C(22)	−0.1483 (3)	0.0817 (6)	0.8831 (2)	0.0335
C(23)	−0.0827 (3)	0.1281 (5)	0.9105 (2)	0.0197
C(24)	0.0820 (2)	0.3231 (4)	0.8926 (2)	0.0134
C(25)	0.1084 (2)	0.1629 (4)	0.8774 (2)	0.0180
C(26)	0.0845 (3)	0.2900 (5)	0.7883 (2)	0.0215
C(27)	0.0144 (3)	0.2237 (6)	0.7618 (2)	0.0350
C(28)	0.1330 (3)	0.3708 (5)	0.7435 (2)	0.0326
C(29)	0.1760 (2)	0.1048 (5)	0.9118 (2)	0.0172
C(30)	0.1946 (2)	−0.0586 (5)	0.8944 (2)	0.0201
C(31)	0.1648 (3)	−0.1310 (5)	0.8449 (2)	0.0260
C(32)	0.1844 (3)	−0.2791 (5)	0.8323 (2)	0.0257
C(33)	0.2329 (3)	−0.3540 (5)	0.8676 (2)	0.0274
C(34)	0.2635 (3)	−0.2828 (5)	0.9171 (2)	0.0339
C(35)	0.2454 (3)	−0.1352 (5)	0.9293 (2)	0.0224
C(36)	0.2461 (2)	0.1998 (5)	0.9068 (2)	0.0187
C(37)	0.2764 (3)	0.2799 (5)	0.9548 (2)	0.0222
C(38)	0.3421 (3)	0.3609 (5)	0.9486 (2)	0.0280
C(39)	0.3786 (2)	0.3657 (5)	0.8949 (2)	0.0256
C(40)	0.3499 (3)	0.2883 (6)	0.8471 (2)	0.0363
C(41)	0.2846 (3)	0.2066 (5)	0.8525 (2)	0.0210
H(1)	0.1733	0.1275	1.1161	0.0266*
H(2)	0.0929	0.3099	1.1490	0.0335*
H(3)	0.0341	0.1905	1.1672	0.0335*
H(4)	0.1702	0.2350	1.2256	0.0353*
H(5)	0.1390	0.0432	1.2899	0.0346*
H(6)	0.0640	0.0193	1.2565	0.0346*
H(7)	0.2051	−0.0408	1.2072	0.0400*
H(8)	0.1478	−0.1632	1.2253	0.0400*
H(9)	0.0688	−0.0872	1.1500	0.0300*
H(10)	0.1024	0.3117	1.3077	0.0477*
H(11)	0.0862	0.4159	1.2537	0.0477*
H(12)	0.0289	0.2933	1.2716	0.0477*
H(13)	0.1342	−0.1612	1.0660	0.0405*
H(14)	0.0844	−0.3482	1.1267	0.0642*
H(15)	0.1541	−0.4052	1.0923	0.0642*
H(16)	0.1608	−0.3612	1.1591	0.0642*
H(17)	0.2639	−0.1807	1.1331	0.0475*
H(18)	0.2568	−0.2246	1.0663	0.0475*
H(19)	0.2503	−0.0579	1.0853	0.0475*
H(20)	−0.0645	0.4063	1.0310	0.0371*
H(21)	−0.0843	0.6371	1.0766	0.0395*
H(22)	−0.0296	0.8546	1.0373	0.0377*
H(23)	0.0466	0.8372	0.9532	0.0412*
H(24)	0.0655	0.6064	0.9062	0.0262*
H(25)	−0.0828	0.4734	0.8645	0.0421*
H(26)	−0.1920	0.3910	0.8163	0.0387*
H(27)	−0.2317	0.1461	0.8289	0.0465*
H(28)	−0.1659	−0.0179	0.8885	0.0402*
H(29)	−0.0546	0.0590	0.9336	0.0237*
H(30)	0.1222	0.3754	0.9109	0.0160*
H(31)	0.0680	0.0947	0.8814	0.0217*
H(32)	−0.0148	0.3011	0.7443	0.0420*
H(33)	0.0274	0.1523	0.7322	0.0420*
H(34)	−0.0137	0.1760	0.7924	0.0420*
H(35)	0.1749	0.4134	0.7633	0.0391*
H(36)	0.1498	0.3018	0.7141	0.0391*
H(37)	0.1048	0.4479	0.7249	0.0391*
H(38)	0.1309	−0.0795	0.8195	0.0312*
H(39)	0.1635	−0.3278	0.7985	0.0309*
H(40)	0.2460	−0.4546	0.8587	0.0329*
H(41)	0.2969	−0.3355	0.9425	0.0407*
H(42)	0.2682	−0.0860	0.9622	0.0268*
H(43)	0.2515	0.2788	0.9923	0.0266*
H(44)	0.3619	0.4136	0.9818	0.0337*
H(45)	0.4234	0.4219	0.8908	0.0308*
H(46)	0.3752	0.2910	0.8098	0.0436*
H(47)	0.2656	0.1544	0.8188	0.0252*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P(1)	0.0222 (7)	0.0154 (7)	0.0141 (6)	0.0020 (7)	0.0010 (6)	0.0009 (6)
O(1)	0.029 (2)	0.024 (2)	0.009 (1)	0.002 (2)	−0.002 (1)	0.007 (1)
O(2)	0.017 (2)	0.018 (2)	0.012 (1)	0.001 (1)	0.000 (1)	0.003 (1)
O(3)	0.025 (2)	0.017 (2)	0.014 (2)	0.004 (1)	0.005 (1)	0.000 (1)
O(4)	0.038 (2)	0.012 (2)	0.011 (2)	0.006 (2)	0.002 (1)	0.003 (1)
O(5)	0.028 (2)	0.020 (2)	0.011 (1)	0.007 (1)	0.003 (1)	0.002 (1)
C(1)	0.025 (3)	0.025 (3)	0.015 (2)	−0.006 (2)	−0.005 (2)	0.001 (2)
C(2)	0.029 (3)	0.032 (3)	0.021 (2)	−0.004 (3)	−0.001 (2)	0.004 (2)
C(3)	0.030 (3)	0.030 (3)	0.017 (2)	−0.002 (3)	0.000 (2)	0.002 (2)
C(4)	0.036 (3)	0.041 (3)	0.018 (3)	0.001 (3)	0.000 (3)	0.007 (2)
C(5)	0.042 (3)	0.036 (3)	0.017 (2)	−0.001 (3)	−0.002 (2)	0.012 (2)
C(6)	0.024 (3)	0.029 (3)	0.019 (3)	−0.002 (2)	−0.002 (2)	0.004 (2)
C(7)	0.053 (4)	0.056 (4)	0.021 (3)	0.011 (3)	−0.002 (3)	−0.008 (3)
C(8)	0.044 (4)	0.022 (3)	0.028 (3)	0.002 (3)	−0.011 (3)	0.003 (2)
C(9)	0.095 (5)	0.022 (3)	0.049 (3)	0.001 (3)	−0.013 (4)	0.002 (3)
C(10)	0.053 (4)	0.038 (3)	0.032 (3)	0.016 (3)	−0.004 (3)	−0.009 (2)
C(11)	0.021 (3)	0.015 (3)	0.011 (2)	0.004 (2)	0.007 (2)	0.005 (2)
C(12)	0.021 (3)	0.017 (3)	0.023 (3)	0.003 (2)	0.001 (2)	0.000 (2)
C(13)	0.029 (3)	0.026 (3)	0.026 (3)	0.002 (2)	0.006 (3)	−0.005 (2)
C(14)	0.031 (3)	0.038 (3)	0.034 (3)	0.002 (3)	0.009 (2)	−0.013 (3)
C(15)	0.033 (3)	0.024 (3)	0.039 (3)	0.004 (2)	0.002 (3)	−0.014 (3)
C(16)	0.034 (3)	0.024 (3)	0.041 (3)	−0.002 (2)	0.004 (3)	0.001 (2)
C(17)	0.028 (3)	0.020 (3)	0.027 (2)	0.007 (2)	0.008 (2)	−0.002 (2)
C(18)	0.020 (3)	0.029 (3)	0.008 (2)	0.005 (3)	0.003 (2)	−0.003 (2)
C(19)	0.027 (3)	0.028 (3)	0.026 (2)	0.011 (3)	−0.003 (3)	0.000 (2)
C(20)	0.026 (3)	0.039 (4)	0.033 (3)	0.014 (3)	−0.010 (3)	−0.006 (2)
C(21)	0.033 (3)	0.050 (4)	0.031 (3)	0.000 (3)	−0.009 (3)	−0.018 (3)
C(22)	0.026 (3)	0.038 (3)	0.026 (3)	−0.005 (3)	0.001 (3)	−0.016 (2)
C(23)	0.026 (3)	0.022 (3)	0.015 (2)	0.005 (2)	0.006 (2)	0.001 (2)
C(24)	0.020 (3)	0.014 (3)	0.013 (2)	0.001 (2)	0.002 (2)	0.001 (2)
C(25)	0.017 (2)	0.020 (3)	0.015 (2)	0.001 (2)	0.006 (2)	0.001 (2)
C(26)	0.033 (3)	0.018 (2)	0.018 (2)	0.003 (3)	0.003 (2)	0.000 (2)
C(27)	0.044 (3)	0.035 (3)	0.024 (3)	0.008 (3)	−0.009 (2)	−0.008 (2)
C(28)	0.062 (4)	0.025 (3)	0.017 (2)	0.004 (3)	0.011 (3)	0.000 (2)
C(29)	0.015 (3)	0.018 (3)	0.015 (2)	−0.003 (2)	0.000 (2)	0.001 (2)
C(30)	0.028 (3)	0.006 (2)	0.018 (3)	0.001 (2)	0.005 (2)	0.003 (2)
C(31)	0.029 (3)	0.018 (3)	0.021 (2)	0.001 (2)	−0.008 (2)	0.001 (2)
C(32)	0.039 (3)	0.013 (3)	0.025 (2)	0.003 (3)	−0.003 (3)	−0.006 (2)
C(33)	0.034 (3)	0.012 (3)	0.032 (3)	0.002 (2)	0.004 (3)	−0.005 (2)
C(34)	0.049 (4)	0.020 (3)	0.042 (3)	0.015 (3)	−0.013 (3)	0.001 (3)
C(35)	0.035 (3)	0.018 (3)	0.029 (3)	0.010 (3)	−0.010 (2)	−0.006 (2)
C(36)	0.017 (3)	0.011 (2)	0.021 (2)	0.008 (2)	0.001 (2)	0.001 (2)
C(37)	0.026 (3)	0.024 (3)	0.012 (2)	0.002 (3)	−0.001 (2)	0.005 (2)
C(38)	0.028 (3)	0.021 (3)	0.018 (3)	−0.001 (3)	−0.006 (2)	0.005 (2)
C(39)	0.019 (3)	0.026 (3)	0.030 (3)	0.000 (3)	0.003 (2)	−0.003 (2)
C(40)	0.030 (3)	0.029 (3)	0.027 (3)	0.000 (3)	0.008 (2)	−0.008 (3)
C(41)	0.025 (3)	0.031 (3)	0.017 (2)	−0.006 (3)	0.003 (2)	−0.005 (2)

Geometric parameters (Å, º)

P1—O1	1.610 (3)	C38—C39	1.368 (5)
P1—O2	1.629 (3)	C39—C40	1.375 (6)
P1—O3	1.656 (3)	C40—C41	1.381 (6)
O1—C1	1.469 (5)	C1—H1	0.9500
O2—C11	1.460 (4)	C2—H2	0.9500
O3—C29	1.466 (4)	C2—H3	0.9500
O4—C24	1.434 (4)	C3—H4	0.9500
O4—C26	1.445 (5)	C4—H5	0.9500
O5—C25	1.447 (4)	C4—H6	0.9500
O5—C26	1.427 (5)	C5—H7	0.9500
C1—C2	1.526 (6)	C5—H8	0.9500
C1—C6	1.526 (6)	C6—H9	0.9500
C2—C3	1.532 (5)	C7—H10	0.9500
C3—C4	1.532 (6)	C7—H11	0.9500
C3—C7	1.507 (6)	C7—H12	0.9500
C4—C5	1.541 (6)	C8—H13	0.9500
C5—C6	1.536 (5)	C9—H14	0.9500
C6—C8	1.539 (6)	C9—H15	0.9500
C8—C9	1.535 (7)	C9—H16	0.9500
C8—C10	1.514 (7)	C10—H17	0.9500
C11—C12	1.543 (5)	C10—H18	0.9500
C11—C18	1.523 (5)	C10—H19	0.9500
C11—C24	1.536 (5)	C13—H20	0.9500
C12—C13	1.404 (6)	C14—H21	0.9500
C12—C17	1.380 (6)	C15—H22	0.9500
C13—C14	1.382 (6)	C16—H23	0.9500
C14—C15	1.392 (6)	C17—H24	0.9500
C15—C16	1.378 (6)	C19—H25	0.9500
C16—C17	1.395 (6)	C20—H26	0.9500
C18—C19	1.383 (6)	C21—H27	0.9500
C18—C23	1.400 (6)	C22—H28	0.9500
C19—C20	1.400 (6)	C23—H29	0.9500
C20—C21	1.370 (7)	C24—H30	0.9500
C21—C22	1.361 (7)	C25—H31	0.9500
C22—C23	1.388 (6)	C27—H32	0.9500
C24—C25	1.544 (6)	C27—H33	0.9500
C25—C29	1.524 (5)	C27—H34	0.9500
C26—C27	1.508 (6)	C28—H35	0.9500
C26—C28	1.508 (6)	C28—H36	0.9500
C29—C30	1.545 (5)	C28—H37	0.9500
C29—C36	1.518 (5)	C31—H38	0.9500
C30—C31	1.390 (5)	C32—H39	0.9500
C30—C35	1.380 (6)	C33—H40	0.9500
C31—C32	1.396 (6)	C34—H41	0.9500
C32—C33	1.351 (6)	C35—H42	0.9500
C33—C34	1.388 (6)	C37—H43	0.9500
C34—C35	1.384 (6)	C38—H44	0.9500
C36—C37	1.400 (5)	C39—H45	0.9500
C36—C41	1.400 (5)	C40—H46	0.9500
C37—C38	1.387 (6)	C41—H47	0.9500
O1—P1—O2	93.8 (1)	C3—C4—H6	108.9246
O1—P1—O3	95.9 (1)	C5—C4—H5	108.9563
O2—P1—O3	99.8 (1)	C5—C4—H6	108.9428
P1—O1—C1	117.6 (2)	H5—C4—H6	109.4236
P1—O2—C11	120.2 (2)	C4—C5—H7	108.7485
P1—O3—C29	126.7 (2)	C4—C5—H8	108.7578
C24—O4—C26	109.9 (3)	C6—C5—H7	108.7043
C25—O5—C26	108.7 (3)	C6—C5—H8	108.7014
O1—C1—C2	107.9 (3)	H7—C5—H8	109.4434
O1—C1—C6	106.9 (3)	C1—C6—H9	106.8490
C2—C1—C6	113.2 (4)	C5—C6—H9	106.8895
C1—C2—C3	112.6 (4)	C8—C6—H9	106.8677
C2—C3—C4	109.4 (4)	C3—C7—H10	109.4685
C2—C3—C7	111.7 (4)	C3—C7—H11	109.4666
C4—C3—C7	111.9 (4)	C3—C7—H12	109.4863
C3—C4—C5	111.6 (3)	H10—C7—H11	109.4433
C4—C5—C6	112.5 (4)	H10—C7—H12	109.4700
C1—C6—C5	109.0 (4)	H11—C7—H12	109.4925
C1—C6—C8	113.8 (4)	C6—C8—H13	106.5704
C5—C6—C8	113.0 (4)	C9—C8—H13	106.5347
C6—C8—C9	112.1 (4)	C10—C8—H13	106.6199
C6—C8—C10	114.1 (4)	C8—C9—H14	109.4866
C9—C8—C10	110.5 (4)	C8—C9—H15	109.5146
O2—C11—C12	108.5 (3)	C8—C9—H16	109.3866
O2—C11—C18	105.3 (3)	H14—C9—H15	109.5712
O2—C11—C24	106.5 (3)	H14—C9—H16	109.3807
C12—C11—C18	110.4 (3)	H15—C9—H16	109.4875
C12—C11—C24	112.9 (3)	C8—C10—H17	109.4334
C18—C11—C24	112.8 (3)	C8—C10—H18	109.5083
C11—C12—C13	118.6 (4)	C8—C10—H19	109.4677
C11—C12—C17	122.3 (4)	H17—C10—H18	109.4831
C13—C12—C17	119.0 (4)	H17—C10—H19	109.4112
C12—C13—C14	120.3 (4)	H18—C10—H19	109.5235
C13—C14—C15	120.5 (4)	C12—C13—H20	119.9040
C14—C15—C16	119.2 (4)	C14—C13—H20	119.8244
C15—C16—C17	120.7 (4)	C13—C14—H21	119.7610
C12—C17—C16	120.3 (4)	C15—C14—H21	119.7486
C11—C18—C19	120.7 (4)	C14—C15—H22	120.3950
C11—C18—C23	121.1 (4)	C16—C15—H22	120.4159
C19—C18—C23	118.2 (4)	C15—C16—H23	119.6595
C18—C19—C20	120.9 (4)	C17—C16—H23	119.6108
C19—C20—C21	119.2 (4)	C12—C17—H24	119.8654
C20—C21—C22	121.3 (5)	C16—C17—H24	119.8502
C21—C22—C23	119.8 (5)	C18—C19—H25	119.5520
C18—C23—C22	120.7 (4)	C20—C19—H25	119.5782
O4—C24—C11	111.7 (3)	C19—C20—H26	120.4036
O4—C24—C25	105.2 (3)	C21—C20—H26	120.3793
C11—C24—C25	113.9 (3)	C20—C21—H27	119.3628
O5—C25—C24	102.4 (3)	C22—C21—H27	119.3456
O5—C25—C29	108.0 (3)	C21—C22—H28	120.1010
C24—C25—C29	116.5 (3)	C23—C22—H28	120.1357
O4—C26—O5	105.1 (3)	C18—C23—H29	119.6340
O4—C26—C27	110.5 (3)	C22—C23—H29	119.6965
O4—C26—C28	108.9 (4)	O4—C24—H30	108.5849
O5—C26—C27	110.8 (4)	C11—C24—H30	108.6218
O5—C26—C28	107.3 (3)	C25—C24—H30	108.5869
C27—C26—C28	113.8 (4)	O5—C25—H31	109.8682
O3—C29—C25	106.8 (3)	C24—C25—H31	109.8495
O3—C29—C30	102.1 (3)	C29—C25—H31	109.8573
O3—C29—C36	111.2 (3)	C26—C27—H32	109.4821
C25—C29—C30	111.3 (3)	C26—C27—H33	109.5169
C25—C29—C36	115.3 (3)	C26—C27—H34	109.4585
C30—C29—C36	109.3 (3)	H32—C27—H33	109.4961
C29—C30—C31	123.9 (4)	H32—C27—H34	109.4120
C29—C30—C35	117.8 (4)	H33—C27—H34	109.4616
C31—C30—C35	118.3 (4)	C26—C28—H35	109.4624
C30—C31—C32	120.4 (4)	C26—C28—H36	109.4713
C31—C32—C33	120.7 (4)	C26—C28—H37	109.5012
C32—C33—C34	119.6 (4)	H35—C28—H36	109.4233
C33—C34—C35	120.0 (4)	H35—C28—H37	109.4654
C30—C35—C34	120.9 (4)	H36—C28—H37	109.5037
C29—C36—C37	123.2 (4)	C30—C31—H38	119.8525
C29—C36—C41	119.7 (4)	C32—C31—H38	119.7821
C37—C36—C41	117.1 (4)	C31—C32—H39	119.6895
C36—C37—C38	121.0 (4)	C33—C32—H39	119.6317
C37—C38—C39	120.7 (4)	C32—C33—H40	120.2003
C38—C39—C40	119.3 (4)	C34—C33—H40	120.1704
C39—C40—C41	120.9 (4)	C33—C34—H41	120.0022
C36—C41—C40	121.0 (4)	C35—C34—H41	119.9564
O1—C1—H1	109.5826	C30—C35—H42	119.5506
C2—C1—H1	109.5495	C34—C35—H42	119.5260
C6—C1—H1	109.5850	C36—C37—H43	119.4778
C1—C2—H2	108.6889	C38—C37—H43	119.4748
C1—C2—H3	108.6207	C37—C38—H44	119.6782
C3—C2—H2	108.7278	C39—C38—H44	119.6533
C3—C2—H3	108.6727	C38—C39—H45	120.3142
H2—C2—H3	109.4488	C40—C39—H45	120.3375
C2—C3—H4	107.9314	C39—C40—H46	119.5714
C4—C3—H4	107.8991	C41—C40—H46	119.5663
C7—C3—H4	107.8977	C36—C41—H47	119.4996
C3—C4—H5	108.9645	C40—C41—H47	119.5309