Maleopimaric acid trimethyl ester

Pan, Y.-M.; Yang, L.; Wang, H.-S.; Zhao, Z.-C.; Zhang, Y.

doi:10.1107/S1600536806048756

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Maleopimaric acid trimethyl ester

Y.-M. Pan, L. Yang, H.-S. Wang, Z.-C. Zhao and Y. Zhang

The title compound, C₂₇H₄₀O₆, contains two fused cyclohexane rings with chair conformations, fused to a norbornene ring system. The ester groups that are attached to the norbornene unit are in a cis configuration. There are two molecules in the asymmetric unit. The structure is stabilized by C—H

O intermolecular hydrogen bonds and van der Waals forces.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048756/ym2017sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048756/ym2017Isup2.hkl Contains datablock I

CCDC reference: 630538

checkCIF report

Key indicators

Single-crystal X-ray study
T = 193 K
Mean (C-C) = 0.004 Å
R factor = 0.036
wR factor = 0.086
Data-to-parameter ratio = 7.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT024_ALERT_4_B Merging of Friedel Pairs is STRONGLY Indicated .          !
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.52 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.36 Ratio

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.804     0.990
            Tmin(prime) and Tmax expected:      0.933     0.990
            RR(prime) =      0.862
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.86
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.79 mm
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.57
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.56
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.69 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.21 Ratio

Alert level G
REFLT03_ALERT_4_G 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.
           From the CIF: _diffrn_reflns_theta_max           25.30
           From the CIF: _reflns_number_total               4615
           Count of symmetry unique reflns         4599
           Completeness (_total/calc)            100.35%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured        16
           Fraction of Friedel pairs measured     0.003
           Are heavy atom types Z>Si present         no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C28    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C29    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C30    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C32    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C33    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C38    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C39    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C40    = .          R

   0 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
  17 ALERT level G = General alerts; check

  16 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL (Sheldrick, 2000) and PLATON (Spek, 2003).

Maleopimaric acid trimethyl ester top

Crystal data top

C₂₇H₄₀O₆	F(000) = 1000
M_r = 460.59	D_x = 1.240 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: P 2yb	Cell parameters from 10117 reflections
a = 8.9848 (15) Å	θ = 3.0–25.3°
b = 23.456 (4) Å	µ = 0.09 mm⁻¹
c = 12.364 (2) Å	T = 193 K
β = 108.804 (3)°	Block, colorless
V = 2466.6 (7) Å³	0.79 × 0.60 × 0.12 mm
Z = 4

Data collection top

Rigaku Mercury diffractometer	4615 independent reflections
Radiation source: fine-focus sealed tube	4475 reflections with I > 2/s(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.3°, θ_min = 3.0°
ω scans	h = −10→10
Absorption correction: multi-scan (Jacobson, 1998)	k = −28→28
T_min = 0.804, T_max = 0.990	l = −14→14
24150 measured reflections

Refinement top

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)] = 0.036	H-atom parameters constrained
wR(F²) = 0.086	w = 1/[σ²(F_o²) + (0.0442P)² + 0.5815P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
4615 reflections	Δρ_max = 0.41 e Å⁻³
610 parameters	Δρ_min = −0.16 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 4148 Friedel pairs
Primary atom site location: structure-invariant direct methods

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.2386 (2)	0.15996 (8)	0.57030 (17)	0.0363 (5)
O2	0.4564 (2)	0.19978 (8)	0.69011 (17)	0.0353 (4)
O3	−0.0806 (2)	0.15003 (9)	0.65911 (19)	0.0442 (5)
O4	0.1616 (2)	0.15020 (9)	0.78748 (16)	0.0367 (5)
O5	0.5653 (2)	0.43451 (9)	0.52519 (17)	0.0378 (5)
O6	0.5084 (2)	0.51223 (9)	0.4168 (2)	0.0421 (5)
O7	0.8790 (2)	0.55025 (9)	0.93004 (17)	0.0363 (4)
O8	1.0045 (2)	0.51658 (8)	0.81400 (18)	0.0364 (5)
O9	0.4793 (2)	0.55359 (9)	0.81206 (18)	0.0407 (5)
O10	0.6372 (2)	0.55072 (8)	0.70350 (16)	0.0341 (4)
O11	1.2849 (2)	0.27422 (8)	0.96366 (17)	0.0353 (5)
O12	1.3183 (2)	0.19470 (8)	1.06778 (17)	0.0343 (4)
C1	0.2207 (3)	0.25040 (11)	0.6600 (2)	0.0251 (5)
H1	0.2982	0.2713	0.7243	0.030*
C2	0.0728 (3)	0.23726 (11)	0.6960 (2)	0.0266 (5)
H2	0.0928	0.2546	0.7733	0.032*
C3	−0.0708 (3)	0.26870 (11)	0.6145 (2)	0.0260 (5)
H3	−0.1678	0.2597	0.6342	0.031*
C4	−0.0346 (3)	0.33305 (11)	0.6281 (2)	0.0281 (6)
H4A	−0.0169	0.3446	0.7083	0.034*
H4B	−0.1254	0.3549	0.5786	0.034*
C5	0.1138 (3)	0.34682 (11)	0.5946 (2)	0.0238 (5)
H5	0.1975	0.3573	0.6674	0.029*
C6	0.1714 (3)	0.29075 (10)	0.5527 (2)	0.0231 (5)
C7	−0.0898 (3)	0.25040 (11)	0.4937 (2)	0.0256 (5)
C8	0.0363 (3)	0.26224 (11)	0.4639 (2)	0.0248 (5)
H8	0.0410	0.2532	0.3901	0.030*
C9	0.3130 (3)	0.30108 (11)	0.5120 (2)	0.0268 (5)
H9A	0.4078	0.3068	0.5794	0.032*
H9B	0.3306	0.2667	0.4711	0.032*
C10	0.2921 (3)	0.35260 (11)	0.4332 (2)	0.0271 (5)
H10A	0.2040	0.3457	0.3619	0.033*
H10B	0.3889	0.3587	0.4129	0.033*
C11	0.2579 (3)	0.40550 (11)	0.4937 (2)	0.0241 (5)
H11	0.3374	0.4042	0.5718	0.029*
C12	0.0963 (3)	0.39947 (11)	0.5140 (2)	0.0239 (5)
C13	0.2897 (3)	0.46294 (11)	0.4422 (2)	0.0268 (5)
C14	0.2474 (3)	0.51355 (11)	0.5071 (2)	0.0299 (6)
H14A	0.3266	0.5161	0.5841	0.036*
H14B	0.2524	0.5493	0.4659	0.036*
C15	0.0851 (3)	0.50816 (12)	0.5191 (2)	0.0312 (6)
H15A	0.0045	0.5095	0.4425	0.037*
H15B	0.0665	0.5407	0.5641	0.037*
C16	0.0695 (3)	0.45243 (12)	0.5783 (2)	0.0297 (6)
H16A	−0.0370	0.4504	0.5855	0.036*
H16B	0.1466	0.4523	0.6563	0.036*
C17	0.3004 (3)	0.19803 (11)	0.6345 (2)	0.0266 (5)
C18	0.5476 (4)	0.15331 (15)	0.6674 (3)	0.0484 (8)
H18A	0.5199	0.1478	0.5847	0.073*
H18B	0.5249	0.1183	0.7026	0.073*
H18C	0.6598	0.1623	0.6996	0.073*
C19	0.0399 (3)	0.17470 (12)	0.7074 (2)	0.0310 (6)
C20	0.1389 (5)	0.09133 (14)	0.8119 (3)	0.0534 (9)
H20A	0.1365	0.0677	0.7460	0.080*
H20B	0.0391	0.0873	0.8275	0.080*
H20C	0.2255	0.0790	0.8789	0.080*
C21	−0.2381 (3)	0.22056 (13)	0.4223 (2)	0.0335 (6)
H21	−0.2756	0.1963	0.4749	0.040*
C22	−0.2088 (4)	0.18136 (15)	0.3330 (3)	0.0447 (8)
H22A	−0.1242	0.1546	0.3704	0.067*
H22B	−0.1784	0.2042	0.2771	0.067*
H22C	−0.3051	0.1601	0.2940	0.067*
C23	−0.3668 (4)	0.26340 (19)	0.3670 (4)	0.0621 (10)
H23A	−0.3351	0.2869	0.3126	0.093*
H23B	−0.3841	0.2879	0.4261	0.093*
H23C	−0.4642	0.2431	0.3268	0.093*
C24	−0.0441 (3)	0.39261 (12)	0.4031 (2)	0.0297 (6)
H24A	−0.0575	0.4277	0.3580	0.045*
H24B	−0.1399	0.3851	0.4224	0.045*
H24C	−0.0242	0.3607	0.3586	0.045*
C25	0.4683 (3)	0.46645 (11)	0.4664 (2)	0.0283 (6)
C26	0.6763 (4)	0.51972 (14)	0.4401 (3)	0.0489 (8)
H26A	0.7174	0.4880	0.4066	0.073*
H26B	0.7293	0.5205	0.5229	0.073*
H26C	0.6955	0.5557	0.4066	0.073*
C27	0.2068 (3)	0.46948 (13)	0.3125 (2)	0.0336 (6)
H27A	0.2286	0.4359	0.2728	0.050*
H27B	0.2459	0.5037	0.2851	0.050*
H27C	0.0931	0.4729	0.2972	0.050*
C28	0.8053 (3)	0.45849 (11)	0.8394 (2)	0.0245 (5)
H28	0.8310	0.4398	0.7749	0.029*
C29	0.6238 (3)	0.46717 (12)	0.8026 (2)	0.0281 (6)
H29	0.5802	0.4467	0.7281	0.034*
C30	0.5562 (3)	0.43618 (12)	0.8861 (2)	0.0306 (6)
H30	0.4415	0.4444	0.8675	0.037*
C31	0.5842 (3)	0.37198 (11)	0.8706 (2)	0.0316 (6)
H31A	0.5291	0.3606	0.7906	0.038*
H31B	0.5412	0.3491	0.9210	0.038*
C32	0.7628 (3)	0.36035 (11)	0.9007 (2)	0.0236 (5)
H32	0.7804	0.3513	0.8267	0.028*
C33	0.8553 (3)	0.41708 (11)	0.9446 (2)	0.0242 (5)
C34	0.6449 (3)	0.45180 (12)	1.0085 (2)	0.0318 (6)
C35	0.7984 (3)	0.44219 (11)	1.0361 (2)	0.0283 (6)
H35	0.8687	0.4508	1.1100	0.034*
C36	1.0337 (3)	0.40819 (11)	0.9835 (2)	0.0276 (6)
H36A	1.0676	0.4044	0.9152	0.033*
H36B	1.0857	0.4424	1.0261	0.033*
C37	1.0879 (3)	0.35578 (11)	1.0590 (2)	0.0278 (6)
H37A	1.0660	0.3611	1.1318	0.033*
H37B	1.2027	0.3507	1.0767	0.033*
C38	1.0018 (3)	0.30295 (11)	0.9976 (2)	0.0233 (5)
H38	1.0102	0.3052	0.9190	0.028*
C39	0.8234 (3)	0.30730 (11)	0.9795 (2)	0.0243 (5)
C40	1.0829 (3)	0.24561 (11)	1.0470 (2)	0.0239 (5)
C41	0.9838 (3)	0.19471 (11)	0.9836 (2)	0.0279 (6)
H41A	0.9929	0.1922	0.9060	0.034*
H41B	1.0274	0.1591	1.0246	0.034*
C42	0.8109 (3)	0.19892 (11)	0.9732 (2)	0.0289 (6)
H42A	0.7998	0.1973	1.0502	0.035*
H42B	0.7532	0.1662	0.9285	0.035*
C43	0.7400 (3)	0.25438 (11)	0.9147 (2)	0.0287 (6)
H43A	0.6274	0.2558	0.9084	0.034*
H43B	0.7468	0.2549	0.8363	0.034*
C44	0.8966 (3)	0.51369 (11)	0.8679 (2)	0.0253 (5)
C45	1.0938 (4)	0.56897 (14)	0.8317 (3)	0.0493 (8)
H45A	1.1377	0.5768	0.9138	0.074*
H45B	1.0248	0.6005	0.7940	0.074*
H45C	1.1796	0.5652	0.7993	0.074*
C46	0.5727 (3)	0.52839 (12)	0.7782 (2)	0.0304 (6)
C47	0.6014 (4)	0.60966 (13)	0.6735 (3)	0.0417 (7)
H47A	0.6264	0.6327	0.7433	0.062*
H47B	0.4894	0.6135	0.6303	0.062*
H47C	0.6642	0.6229	0.6267	0.062*
C48	0.5676 (4)	0.46984 (15)	1.0961 (3)	0.0477 (8)
H48	0.6534	0.4850	1.1634	0.057*
C49	0.4480 (5)	0.51755 (19)	1.0559 (3)	0.0653 (11)
H49A	0.4038	0.5269	1.1166	0.098*
H49B	0.3635	0.5052	0.9876	0.098*
H49C	0.4996	0.5513	1.0376	0.098*
C50	0.5004 (6)	0.4198 (2)	1.1378 (5)	0.0815 (15)
H50A	0.5854	0.3939	1.1787	0.122*
H50B	0.4270	0.3999	1.0726	0.122*
H50C	0.4444	0.4327	1.1895	0.122*
C51	0.7839 (3)	0.31216 (12)	1.0913 (2)	0.0300 (6)
H51A	0.8411	0.3444	1.1361	0.045*
H51B	0.8148	0.2770	1.1356	0.045*
H51C	0.6706	0.3182	1.0736	0.045*
C52	1.2383 (3)	0.24157 (11)	1.0212 (2)	0.0269 (5)
C53	1.4600 (3)	0.18372 (14)	1.0395 (3)	0.0386 (7)
H53A	1.5363	0.2142	1.0707	0.058*
H53B	1.4345	0.1824	0.9563	0.058*
H53C	1.5050	0.1471	1.0724	0.058*
C54	1.1203 (3)	0.23944 (13)	1.1774 (2)	0.0337 (6)
H54A	1.1871	0.2712	1.2162	0.051*
H54B	1.1755	0.2034	1.2028	0.051*
H54C	1.0222	0.2398	1.1958	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0317 (10)	0.0304 (11)	0.0426 (11)	0.0004 (8)	0.0061 (8)	−0.0100 (9)
O2	0.0246 (10)	0.0334 (11)	0.0435 (11)	0.0028 (8)	0.0050 (8)	−0.0082 (9)
O3	0.0398 (12)	0.0365 (12)	0.0567 (13)	−0.0063 (10)	0.0162 (10)	0.0040 (10)
O4	0.0454 (12)	0.0304 (10)	0.0335 (10)	0.0051 (9)	0.0116 (9)	0.0053 (9)
O5	0.0285 (10)	0.0346 (11)	0.0475 (12)	−0.0006 (9)	0.0084 (9)	0.0071 (10)
O6	0.0289 (11)	0.0324 (11)	0.0686 (14)	0.0010 (8)	0.0209 (10)	0.0149 (10)
O7	0.0450 (11)	0.0292 (10)	0.0387 (11)	−0.0052 (9)	0.0190 (9)	−0.0093 (9)
O8	0.0381 (11)	0.0277 (10)	0.0521 (12)	−0.0023 (8)	0.0265 (10)	−0.0003 (9)
O9	0.0396 (11)	0.0330 (11)	0.0530 (12)	0.0076 (9)	0.0196 (10)	0.0039 (10)
O10	0.0399 (11)	0.0286 (10)	0.0337 (10)	0.0062 (9)	0.0117 (9)	0.0062 (8)
O11	0.0358 (11)	0.0344 (11)	0.0403 (11)	0.0005 (8)	0.0185 (9)	0.0082 (9)
O12	0.0290 (10)	0.0350 (11)	0.0418 (11)	0.0074 (8)	0.0156 (9)	0.0108 (9)
C1	0.0259 (13)	0.0261 (14)	0.0231 (12)	−0.0012 (10)	0.0078 (10)	−0.0027 (10)
C2	0.0311 (14)	0.0301 (14)	0.0219 (12)	0.0006 (11)	0.0130 (10)	−0.0005 (10)
C3	0.0259 (13)	0.0297 (14)	0.0256 (13)	0.0001 (10)	0.0128 (11)	0.0006 (11)
C4	0.0317 (14)	0.0290 (14)	0.0275 (13)	0.0032 (11)	0.0149 (11)	−0.0002 (11)
C5	0.0253 (13)	0.0268 (13)	0.0204 (12)	−0.0004 (10)	0.0089 (10)	−0.0033 (10)
C6	0.0231 (12)	0.0233 (13)	0.0244 (12)	0.0004 (10)	0.0098 (10)	−0.0010 (10)
C7	0.0255 (13)	0.0286 (14)	0.0231 (12)	−0.0008 (10)	0.0082 (10)	0.0010 (11)
C8	0.0289 (13)	0.0247 (13)	0.0218 (12)	−0.0006 (10)	0.0095 (10)	−0.0014 (10)
C9	0.0253 (13)	0.0259 (13)	0.0326 (13)	−0.0014 (10)	0.0141 (11)	−0.0058 (11)
C10	0.0286 (14)	0.0255 (13)	0.0313 (13)	−0.0021 (11)	0.0152 (11)	−0.0027 (11)
C11	0.0228 (13)	0.0250 (13)	0.0242 (12)	−0.0004 (10)	0.0071 (10)	−0.0031 (10)
C12	0.0238 (13)	0.0251 (13)	0.0228 (12)	−0.0015 (10)	0.0077 (10)	−0.0027 (10)
C13	0.0260 (13)	0.0249 (13)	0.0289 (13)	−0.0016 (10)	0.0081 (10)	0.0011 (11)
C14	0.0328 (15)	0.0222 (13)	0.0338 (14)	−0.0006 (11)	0.0094 (12)	0.0003 (11)
C15	0.0314 (14)	0.0273 (14)	0.0361 (15)	0.0038 (11)	0.0127 (12)	−0.0027 (12)
C16	0.0297 (14)	0.0302 (14)	0.0309 (14)	0.0028 (11)	0.0124 (11)	−0.0014 (11)
C17	0.0267 (13)	0.0261 (13)	0.0254 (12)	−0.0014 (11)	0.0064 (11)	0.0030 (11)
C18	0.0316 (16)	0.0491 (19)	0.062 (2)	0.0079 (14)	0.0122 (15)	−0.0132 (17)
C19	0.0376 (16)	0.0352 (15)	0.0250 (13)	0.0025 (12)	0.0167 (12)	0.0005 (11)
C20	0.073 (2)	0.0307 (17)	0.057 (2)	0.0076 (16)	0.0217 (18)	0.0093 (15)
C21	0.0296 (15)	0.0436 (17)	0.0284 (13)	−0.0103 (12)	0.0109 (12)	0.0009 (12)
C22	0.0419 (18)	0.0479 (19)	0.0400 (17)	−0.0153 (14)	0.0074 (14)	−0.0120 (14)
C23	0.0308 (17)	0.076 (3)	0.070 (2)	0.0030 (17)	0.0025 (16)	−0.009 (2)
C24	0.0277 (14)	0.0320 (15)	0.0282 (13)	−0.0013 (11)	0.0074 (11)	0.0018 (11)
C25	0.0315 (14)	0.0209 (13)	0.0336 (14)	−0.0021 (11)	0.0120 (12)	−0.0022 (11)
C26	0.0320 (16)	0.0363 (17)	0.086 (3)	0.0001 (13)	0.0293 (17)	0.0104 (17)
C27	0.0317 (15)	0.0366 (16)	0.0323 (14)	−0.0011 (12)	0.0101 (11)	0.0030 (12)
C28	0.0277 (13)	0.0230 (13)	0.0246 (12)	−0.0002 (10)	0.0108 (10)	−0.0016 (10)
C29	0.0274 (13)	0.0260 (14)	0.0281 (13)	0.0003 (11)	0.0052 (10)	0.0002 (11)
C30	0.0229 (13)	0.0285 (14)	0.0417 (15)	0.0022 (11)	0.0120 (11)	0.0050 (12)
C31	0.0243 (14)	0.0305 (15)	0.0378 (15)	−0.0025 (11)	0.0069 (11)	0.0025 (12)
C32	0.0230 (13)	0.0232 (13)	0.0244 (12)	−0.0013 (10)	0.0074 (10)	−0.0011 (10)
C33	0.0260 (13)	0.0234 (13)	0.0233 (12)	−0.0005 (10)	0.0081 (10)	−0.0010 (10)
C34	0.0388 (16)	0.0254 (14)	0.0365 (15)	0.0021 (11)	0.0196 (12)	0.0026 (11)
C35	0.0369 (15)	0.0248 (13)	0.0244 (13)	0.0020 (11)	0.0116 (11)	−0.0007 (10)
C36	0.0267 (14)	0.0234 (13)	0.0311 (13)	−0.0014 (10)	0.0071 (11)	−0.0011 (11)
C37	0.0258 (14)	0.0266 (13)	0.0276 (13)	0.0014 (11)	0.0040 (11)	−0.0007 (11)
C38	0.0266 (12)	0.0241 (12)	0.0197 (11)	−0.0013 (10)	0.0082 (9)	0.0005 (10)
C39	0.0268 (13)	0.0220 (13)	0.0236 (12)	−0.0002 (10)	0.0073 (10)	0.0001 (10)
C40	0.0270 (13)	0.0233 (13)	0.0229 (12)	0.0009 (10)	0.0099 (10)	0.0029 (10)
C41	0.0352 (15)	0.0220 (13)	0.0315 (14)	0.0007 (11)	0.0175 (12)	0.0006 (11)
C42	0.0322 (14)	0.0214 (13)	0.0356 (14)	−0.0049 (11)	0.0146 (12)	−0.0027 (11)
C43	0.0291 (14)	0.0266 (14)	0.0292 (13)	−0.0038 (11)	0.0077 (11)	−0.0018 (11)
C44	0.0273 (13)	0.0224 (13)	0.0264 (13)	0.0012 (10)	0.0091 (11)	0.0043 (11)
C45	0.0448 (19)	0.0350 (17)	0.076 (2)	−0.0101 (14)	0.0304 (17)	−0.0003 (17)
C46	0.0270 (14)	0.0278 (14)	0.0312 (14)	0.0003 (11)	0.0021 (11)	0.0004 (11)
C47	0.0505 (18)	0.0291 (16)	0.0444 (17)	0.0009 (13)	0.0138 (15)	0.0058 (13)
C48	0.058 (2)	0.0430 (18)	0.0540 (19)	0.0066 (15)	0.0342 (17)	0.0039 (15)
C49	0.074 (3)	0.074 (3)	0.061 (2)	0.031 (2)	0.040 (2)	0.004 (2)
C50	0.105 (4)	0.067 (3)	0.109 (4)	0.002 (2)	0.085 (3)	0.001 (3)
C51	0.0358 (15)	0.0291 (14)	0.0280 (13)	0.0005 (11)	0.0146 (12)	0.0022 (11)
C52	0.0288 (14)	0.0263 (13)	0.0244 (12)	0.0014 (11)	0.0067 (11)	0.0014 (11)
C53	0.0260 (14)	0.0435 (18)	0.0485 (17)	0.0043 (12)	0.0152 (13)	0.0054 (14)
C54	0.0415 (16)	0.0345 (15)	0.0256 (13)	0.0070 (12)	0.0117 (12)	0.0049 (12)

Geometric parameters (Å, º) top

O1—C17	1.205 (3)	C24—H24A	0.9800
O2—C17	1.348 (3)	C24—H24B	0.9800
O2—C18	1.444 (4)	C24—H24C	0.9800
O3—C19	1.203 (4)	C26—H26A	0.9800
O4—C19	1.344 (3)	C26—H26B	0.9800
O4—C20	1.442 (4)	C26—H26C	0.9800
O5—C25	1.201 (3)	C27—H27A	0.9800
O6—C25	1.342 (3)	C27—H27B	0.9800
O6—C26	1.452 (4)	C27—H27C	0.9800
O7—C44	1.195 (3)	C28—C44	1.512 (4)
O8—C44	1.344 (3)	C28—C29	1.559 (3)
O8—C45	1.445 (4)	C28—C33	1.569 (3)
O9—C46	1.206 (3)	C28—H28	1.0000
O10—C46	1.345 (3)	C29—C46	1.508 (4)
O10—C47	1.440 (4)	C29—C30	1.539 (4)
O11—C52	1.208 (3)	C29—H29	1.0000
O12—C52	1.338 (3)	C30—C34	1.511 (4)
O12—C53	1.448 (3)	C30—C31	1.549 (4)
C1—C17	1.506 (4)	C30—H30	1.0000
C1—C2	1.562 (3)	C31—C32	1.551 (4)
C1—C6	1.573 (3)	C31—H31A	0.9900
C1—H1	1.0000	C31—H31B	0.9900
C2—C19	1.512 (4)	C32—C39	1.566 (3)
C2—C3	1.544 (4)	C32—C33	1.570 (3)
C2—H2	1.0000	C32—H32	1.0000
C3—C7	1.510 (3)	C33—C35	1.504 (4)
C3—C4	1.542 (4)	C33—C36	1.532 (4)
C3—H3	1.0000	C34—C35	1.328 (4)
C4—C5	1.552 (3)	C34—C48	1.524 (4)
C4—H4A	0.9900	C35—H35	0.9500
C4—H4B	0.9900	C36—C37	1.525 (4)
C5—C6	1.562 (3)	C36—H36A	0.9900
C5—C12	1.563 (4)	C36—H36B	0.9900
C5—H5	1.0000	C37—C38	1.527 (4)
C6—C8	1.506 (3)	C37—H37A	0.9900
C6—C9	1.531 (3)	C37—H37B	0.9900
C7—C8	1.330 (3)	C38—C39	1.548 (4)
C7—C21	1.512 (4)	C38—C40	1.558 (4)
C8—H8	0.9500	C38—H38	1.0000
C9—C10	1.525 (4)	C39—C43	1.535 (4)
C9—H9A	0.9900	C39—C51	1.539 (3)
C9—H9B	0.9900	C40—C52	1.532 (3)
C10—C11	1.530 (3)	C40—C54	1.543 (3)
C10—H10A	0.9900	C40—C41	1.544 (4)
C10—H10B	0.9900	C41—C42	1.520 (4)
C11—C13	1.556 (4)	C41—H41A	0.9900
C11—C12	1.557 (3)	C41—H41B	0.9900
C11—H11	1.0000	C42—C43	1.524 (4)
C12—C16	1.536 (4)	C42—H42A	0.9900
C12—C24	1.543 (4)	C42—H42B	0.9900
C13—C25	1.536 (4)	C43—H43A	0.9900
C13—C27	1.543 (4)	C43—H43B	0.9900
C13—C14	1.547 (4)	C45—H45A	0.9800
C14—C15	1.519 (4)	C45—H45B	0.9800
C14—H14A	0.9900	C45—H45C	0.9800
C14—H14B	0.9900	C47—H47A	0.9800
C15—C16	1.526 (4)	C47—H47B	0.9800
C15—H15A	0.9900	C47—H47C	0.9800
C15—H15B	0.9900	C48—C50	1.485 (5)
C16—H16A	0.9900	C48—C49	1.520 (5)
C16—H16B	0.9900	C48—H48	1.0000
C18—H18A	0.9800	C49—H49A	0.9800
C18—H18B	0.9800	C49—H49B	0.9800
C18—H18C	0.9800	C49—H49C	0.9800
C20—H20A	0.9800	C50—H50A	0.9800
C20—H20B	0.9800	C50—H50B	0.9800
C20—H20C	0.9800	C50—H50C	0.9800
C21—C23	1.518 (5)	C51—H51A	0.9800
C21—C22	1.524 (4)	C51—H51B	0.9800
C21—H21	1.0000	C51—H51C	0.9800
C22—H22A	0.9800	C53—H53A	0.9800
C22—H22B	0.9800	C53—H53B	0.9800
C22—H22C	0.9800	C53—H53C	0.9800
C23—H23A	0.9800	C54—H54A	0.9800
C23—H23B	0.9800	C54—H54B	0.9800
C23—H23C	0.9800	C54—H54C	0.9800

C17—O2—C18	116.1 (2)	C13—C27—H27C	109.5
C19—O4—C20	115.3 (2)	H27A—C27—H27C	109.5
C25—O6—C26	114.9 (2)	H27B—C27—H27C	109.5
C44—O8—C45	115.0 (2)	C44—C28—C29	113.2 (2)
C46—O10—C47	116.1 (2)	C44—C28—C33	110.4 (2)
C52—O12—C53	115.7 (2)	C29—C28—C33	108.41 (19)
C17—C1—C2	113.9 (2)	C44—C28—H28	108.2
C17—C1—C6	109.72 (19)	C29—C28—H28	108.2
C2—C1—C6	108.96 (19)	C33—C28—H28	108.2
C17—C1—H1	108.0	C46—C29—C30	115.0 (2)
C2—C1—H1	108.0	C46—C29—C28	113.9 (2)
C6—C1—H1	108.0	C30—C29—C28	110.1 (2)
C19—C2—C3	112.1 (2)	C46—C29—H29	105.6
C19—C2—C1	115.3 (2)	C30—C29—H29	105.6
C3—C2—C1	109.2 (2)	C28—C29—H29	105.6
C19—C2—H2	106.5	C34—C30—C29	111.3 (2)
C3—C2—H2	106.5	C34—C30—C31	107.8 (2)
C1—C2—H2	106.5	C29—C30—C31	105.2 (2)
C7—C3—C4	109.8 (2)	C34—C30—H30	110.8
C7—C3—C2	108.3 (2)	C29—C30—H30	110.8
C4—C3—C2	107.1 (2)	C31—C30—H30	110.8
C7—C3—H3	110.5	C30—C31—C32	109.7 (2)
C4—C3—H3	110.5	C30—C31—H31A	109.7
C2—C3—H3	110.5	C32—C31—H31A	109.7
C3—C4—C5	110.1 (2)	C30—C31—H31B	109.7
C3—C4—H4A	109.6	C32—C31—H31B	109.7
C5—C4—H4A	109.6	H31A—C31—H31B	108.2
C3—C4—H4B	109.6	C31—C32—C39	114.5 (2)
C5—C4—H4B	109.6	C31—C32—C33	109.0 (2)
H4A—C4—H4B	108.1	C39—C32—C33	114.8 (2)
C4—C5—C6	108.6 (2)	C31—C32—H32	106.0
C4—C5—C12	114.6 (2)	C39—C32—H32	106.0
C6—C5—C12	115.46 (19)	C33—C32—H32	106.0
C4—C5—H5	105.8	C35—C33—C36	113.1 (2)
C6—C5—H5	105.8	C35—C33—C28	107.8 (2)
C12—C5—H5	105.8	C36—C33—C28	109.6 (2)
C8—C6—C9	113.0 (2)	C35—C33—C32	108.8 (2)
C8—C6—C5	109.9 (2)	C36—C33—C32	112.1 (2)
C9—C6—C5	112.0 (2)	C28—C33—C32	105.05 (19)
C8—C6—C1	106.8 (2)	C35—C34—C30	112.6 (2)
C9—C6—C1	109.6 (2)	C35—C34—C48	122.5 (3)
C5—C6—C1	105.09 (19)	C30—C34—C48	124.4 (3)
C8—C7—C3	112.4 (2)	C34—C35—C33	116.7 (2)
C8—C7—C21	127.2 (2)	C34—C35—H35	121.6
C3—C7—C21	120.4 (2)	C33—C35—H35	121.6
C7—C8—C6	116.7 (2)	C37—C36—C33	113.4 (2)
C7—C8—H8	121.7	C37—C36—H36A	108.9
C6—C8—H8	121.7	C33—C36—H36A	108.9
C10—C9—C6	113.0 (2)	C37—C36—H36B	108.9
C10—C9—H9A	109.0	C33—C36—H36B	108.9
C6—C9—H9A	109.0	H36A—C36—H36B	107.7
C10—C9—H9B	109.0	C36—C37—C38	109.8 (2)
C6—C9—H9B	109.0	C36—C37—H37A	109.7
H9A—C9—H9B	107.8	C38—C37—H37A	109.7
C9—C10—C11	109.5 (2)	C36—C37—H37B	109.7
C9—C10—H10A	109.8	C38—C37—H37B	109.7
C11—C10—H10A	109.8	H37A—C37—H37B	108.2
C9—C10—H10B	109.8	C37—C38—C39	110.7 (2)
C11—C10—H10B	109.8	C37—C38—C40	114.0 (2)
H10A—C10—H10B	108.2	C39—C38—C40	116.4 (2)
C10—C11—C13	114.2 (2)	C37—C38—H38	104.8
C10—C11—C12	110.5 (2)	C39—C38—H38	104.8
C13—C11—C12	116.7 (2)	C40—C38—H38	104.8
C10—C11—H11	104.7	C43—C39—C51	108.3 (2)
C13—C11—H11	104.7	C43—C39—C38	109.3 (2)
C12—C11—H11	104.7	C51—C39—C38	113.8 (2)
C16—C12—C24	108.9 (2)	C43—C39—C32	107.73 (19)
C16—C12—C11	108.7 (2)	C51—C39—C32	111.5 (2)
C24—C12—C11	113.9 (2)	C38—C39—C32	106.1 (2)
C16—C12—C5	108.01 (19)	C52—C40—C54	107.8 (2)
C24—C12—C5	111.7 (2)	C52—C40—C41	105.1 (2)
C11—C12—C5	105.5 (2)	C54—C40—C41	110.7 (2)
C25—C13—C27	108.8 (2)	C52—C40—C38	108.3 (2)
C25—C13—C14	105.9 (2)	C54—C40—C38	114.1 (2)
C27—C13—C14	110.2 (2)	C41—C40—C38	110.3 (2)
C25—C13—C11	106.5 (2)	C42—C41—C40	113.5 (2)
C27—C13—C11	114.9 (2)	C42—C41—H41A	108.9
C14—C13—C11	110.1 (2)	C40—C41—H41A	108.9
C15—C14—C13	113.0 (2)	C42—C41—H41B	108.9
C15—C14—H14A	109.0	C40—C41—H41B	108.9
C13—C14—H14A	109.0	H41A—C41—H41B	107.7
C15—C14—H14B	109.0	C41—C42—C43	110.8 (2)
C13—C14—H14B	109.0	C41—C42—H42A	109.5
H14A—C14—H14B	107.8	C43—C42—H42A	109.5
C14—C15—C16	111.0 (2)	C41—C42—H42B	109.5
C14—C15—H15A	109.4	C43—C42—H42B	109.5
C16—C15—H15A	109.4	H42A—C42—H42B	108.1
C14—C15—H15B	109.4	C42—C43—C39	112.5 (2)
C16—C15—H15B	109.4	C42—C43—H43A	109.1
H15A—C15—H15B	108.0	C39—C43—H43A	109.1
C15—C16—C12	113.0 (2)	C42—C43—H43B	109.1
C15—C16—H16A	109.0	C39—C43—H43B	109.1
C12—C16—H16A	109.0	H43A—C43—H43B	107.8
C15—C16—H16B	109.0	O7—C44—O8	123.3 (2)
C12—C16—H16B	109.0	O7—C44—C28	126.2 (2)
H16A—C16—H16B	107.8	O8—C44—C28	110.6 (2)
O1—C17—O2	122.8 (2)	O8—C45—H45A	109.5
O1—C17—C1	126.4 (2)	O8—C45—H45B	109.5
O2—C17—C1	110.8 (2)	H45A—C45—H45B	109.5
O2—C18—H18A	109.5	O8—C45—H45C	109.5
O2—C18—H18B	109.5	H45A—C45—H45C	109.5
H18A—C18—H18B	109.5	H45B—C45—H45C	109.5
O2—C18—H18C	109.5	O9—C46—O10	123.3 (3)
H18A—C18—H18C	109.5	O9—C46—C29	126.8 (3)
H18B—C18—H18C	109.5	O10—C46—C29	109.7 (2)
O3—C19—O4	123.2 (3)	O10—C47—H47A	109.5
O3—C19—C2	126.3 (3)	O10—C47—H47B	109.5
O4—C19—C2	110.3 (2)	H47A—C47—H47B	109.5
O4—C20—H20A	109.5	O10—C47—H47C	109.5
O4—C20—H20B	109.5	H47A—C47—H47C	109.5
H20A—C20—H20B	109.5	H47B—C47—H47C	109.5
O4—C20—H20C	109.5	C50—C48—C49	111.8 (3)
H20A—C20—H20C	109.5	C50—C48—C34	110.9 (3)
H20B—C20—H20C	109.5	C49—C48—C34	114.1 (3)
C7—C21—C23	110.9 (3)	C50—C48—H48	106.5
C7—C21—C22	112.2 (2)	C49—C48—H48	106.5
C23—C21—C22	110.9 (3)	C34—C48—H48	106.5
C7—C21—H21	107.5	C48—C49—H49A	109.5
C23—C21—H21	107.5	C48—C49—H49B	109.5
C22—C21—H21	107.5	H49A—C49—H49B	109.5
C21—C22—H22A	109.5	C48—C49—H49C	109.5
C21—C22—H22B	109.5	H49A—C49—H49C	109.5
H22A—C22—H22B	109.5	H49B—C49—H49C	109.5
C21—C22—H22C	109.5	C48—C50—H50A	109.5
H22A—C22—H22C	109.5	C48—C50—H50B	109.5
H22B—C22—H22C	109.5	H50A—C50—H50B	109.5
C21—C23—H23A	109.5	C48—C50—H50C	109.5
C21—C23—H23B	109.5	H50A—C50—H50C	109.5
H23A—C23—H23B	109.5	H50B—C50—H50C	109.5
C21—C23—H23C	109.5	C39—C51—H51A	109.5
H23A—C23—H23C	109.5	C39—C51—H51B	109.5
H23B—C23—H23C	109.5	H51A—C51—H51B	109.5
C12—C24—H24A	109.5	C39—C51—H51C	109.5
C12—C24—H24B	109.5	H51A—C51—H51C	109.5
H24A—C24—H24B	109.5	H51B—C51—H51C	109.5
C12—C24—H24C	109.5	O11—C52—O12	122.3 (2)
H24A—C24—H24C	109.5	O11—C52—C40	126.6 (2)
H24B—C24—H24C	109.5	O12—C52—C40	111.1 (2)
O5—C25—O6	121.8 (2)	O12—C53—H53A	109.5
O5—C25—C13	126.4 (2)	O12—C53—H53B	109.5
O6—C25—C13	111.8 (2)	H53A—C53—H53B	109.5
O6—C26—H26A	109.5	O12—C53—H53C	109.5
O6—C26—H26B	109.5	H53A—C53—H53C	109.5
H26A—C26—H26B	109.5	H53B—C53—H53C	109.5
O6—C26—H26C	109.5	C40—C54—H54A	109.5
H26A—C26—H26C	109.5	C40—C54—H54B	109.5
H26B—C26—H26C	109.5	H54A—C54—H54B	109.5
C13—C27—H27A	109.5	C40—C54—H54C	109.5
C13—C27—H27B	109.5	H54A—C54—H54C	109.5
H27A—C27—H27B	109.5	H54B—C54—H54C	109.5

C17—C1—C2—C19	4.1 (3)	C44—C28—C29—C46	12.3 (3)
C6—C1—C2—C19	126.9 (2)	C33—C28—C29—C46	135.1 (2)
C17—C1—C2—C3	−123.2 (2)	C44—C28—C29—C30	−118.7 (2)
C6—C1—C2—C3	−0.4 (3)	C33—C28—C29—C30	4.1 (3)
C19—C2—C3—C7	−72.5 (3)	C46—C29—C30—C34	−79.4 (3)
C1—C2—C3—C7	56.6 (3)	C28—C29—C30—C34	51.0 (3)
C19—C2—C3—C4	169.2 (2)	C46—C29—C30—C31	164.2 (2)
C1—C2—C3—C4	−61.7 (3)	C28—C29—C30—C31	−65.4 (3)
C7—C3—C4—C5	−56.5 (3)	C34—C30—C31—C32	−58.2 (3)
C2—C3—C4—C5	60.8 (3)	C29—C30—C31—C32	60.5 (3)
C3—C4—C5—C6	2.7 (3)	C30—C31—C32—C39	133.9 (2)
C3—C4—C5—C12	133.4 (2)	C30—C31—C32—C33	3.8 (3)
C4—C5—C6—C8	50.6 (3)	C44—C28—C33—C35	68.5 (3)
C12—C5—C6—C8	−79.6 (2)	C29—C28—C33—C35	−56.0 (3)
C4—C5—C6—C9	177.0 (2)	C44—C28—C33—C36	−55.0 (3)
C12—C5—C6—C9	46.8 (3)	C29—C28—C33—C36	−179.5 (2)
C4—C5—C6—C1	−64.0 (2)	C44—C28—C33—C32	−175.57 (19)
C12—C5—C6—C1	165.7 (2)	C29—C28—C33—C32	59.9 (2)
C17—C1—C6—C8	71.4 (2)	C31—C32—C33—C35	50.4 (3)
C2—C1—C6—C8	−53.9 (2)	C39—C32—C33—C35	−79.4 (3)
C17—C1—C6—C9	−51.3 (3)	C31—C32—C33—C36	176.3 (2)
C2—C1—C6—C9	−176.6 (2)	C39—C32—C33—C36	46.5 (3)
C17—C1—C6—C5	−171.8 (2)	C31—C32—C33—C28	−64.8 (2)
C2—C1—C6—C5	62.9 (2)	C39—C32—C33—C28	165.38 (19)
C4—C3—C7—C8	57.1 (3)	C29—C30—C34—C35	−55.4 (3)
C2—C3—C7—C8	−59.4 (3)	C31—C30—C34—C35	59.4 (3)
C4—C3—C7—C21	−124.6 (3)	C29—C30—C34—C48	131.6 (3)
C2—C3—C7—C21	118.8 (3)	C31—C30—C34—C48	−113.6 (3)
C3—C7—C8—C6	0.1 (3)	C30—C34—C35—C33	−1.2 (3)
C21—C7—C8—C6	−178.0 (2)	C48—C34—C35—C33	172.0 (3)
C9—C6—C8—C7	178.3 (2)	C36—C33—C35—C34	179.2 (2)
C5—C6—C8—C7	−55.8 (3)	C28—C33—C35—C34	58.0 (3)
C1—C6—C8—C7	57.7 (3)	C32—C33—C35—C34	−55.5 (3)
C8—C6—C9—C10	78.3 (3)	C35—C33—C36—C37	77.6 (3)
C5—C6—C9—C10	−46.4 (3)	C28—C33—C36—C37	−162.1 (2)
C1—C6—C9—C10	−162.7 (2)	C32—C33—C36—C37	−45.9 (3)
C6—C9—C10—C11	56.3 (3)	C33—C36—C37—C38	55.3 (3)
C9—C10—C11—C13	160.4 (2)	C36—C37—C38—C39	−64.9 (3)
C9—C10—C11—C12	−65.8 (3)	C36—C37—C38—C40	161.5 (2)
C10—C11—C12—C16	178.1 (2)	C37—C38—C39—C43	178.4 (2)
C13—C11—C12—C16	−49.3 (3)	C40—C38—C39—C43	−49.2 (3)
C10—C11—C12—C24	−60.3 (3)	C37—C38—C39—C51	−60.4 (3)
C13—C11—C12—C24	72.3 (3)	C40—C38—C39—C51	71.9 (3)
C10—C11—C12—C5	62.5 (2)	C37—C38—C39—C32	62.5 (2)
C13—C11—C12—C5	−164.9 (2)	C40—C38—C39—C32	−165.1 (2)
C4—C5—C12—C16	63.2 (3)	C31—C32—C39—C43	62.4 (3)
C6—C5—C12—C16	−169.6 (2)	C33—C32—C39—C43	−170.5 (2)
C4—C5—C12—C24	−56.6 (3)	C31—C32—C39—C51	−56.3 (3)
C6—C5—C12—C24	70.7 (3)	C33—C32—C39—C51	70.8 (3)
C4—C5—C12—C11	179.3 (2)	C31—C32—C39—C38	179.3 (2)
C6—C5—C12—C11	−53.5 (3)	C33—C32—C39—C38	−53.6 (3)
C10—C11—C13—C25	−67.1 (3)	C37—C38—C40—C52	−68.1 (3)
C12—C11—C13—C25	162.0 (2)	C39—C38—C40—C52	161.1 (2)
C10—C11—C13—C27	53.4 (3)	C37—C38—C40—C54	52.0 (3)
C12—C11—C13—C27	−77.5 (3)	C39—C38—C40—C54	−78.9 (3)
C10—C11—C13—C14	178.5 (2)	C37—C38—C40—C41	177.3 (2)
C12—C11—C13—C14	47.6 (3)	C39—C38—C40—C41	46.5 (3)
C25—C13—C14—C15	−164.7 (2)	C52—C40—C41—C42	−165.6 (2)
C27—C13—C14—C15	77.8 (3)	C54—C40—C41—C42	78.3 (3)
C11—C13—C14—C15	−49.9 (3)	C38—C40—C41—C42	−49.0 (3)
C13—C14—C15—C16	56.6 (3)	C40—C41—C42—C43	56.3 (3)
C14—C15—C16—C12	−59.2 (3)	C41—C42—C43—C39	−59.3 (3)
C24—C12—C16—C15	−70.7 (3)	C51—C39—C43—C42	−69.9 (3)
C11—C12—C16—C15	53.8 (3)	C38—C39—C43—C42	54.5 (3)
C5—C12—C16—C15	167.8 (2)	C32—C39—C43—C42	169.4 (2)
C18—O2—C17—O1	0.8 (4)	C45—O8—C44—O7	−3.1 (4)
C18—O2—C17—C1	−176.6 (2)	C45—O8—C44—C28	177.5 (2)
C2—C1—C17—O1	52.0 (3)	C29—C28—C44—O7	49.6 (3)
C6—C1—C17—O1	−70.4 (3)	C33—C28—C44—O7	−72.1 (3)
C2—C1—C17—O2	−130.7 (2)	C29—C28—C44—O8	−131.0 (2)
C6—C1—C17—O2	106.9 (2)	C33—C28—C44—O8	107.3 (2)
C20—O4—C19—O3	0.4 (4)	C47—O10—C46—O9	6.2 (4)
C20—O4—C19—C2	175.7 (2)	C47—O10—C46—C29	−178.8 (2)
C3—C2—C19—O3	1.4 (4)	C30—C29—C46—O9	−4.5 (4)
C1—C2—C19—O3	−124.5 (3)	C28—C29—C46—O9	−133.0 (3)
C3—C2—C19—O4	−173.8 (2)	C30—C29—C46—O10	−179.2 (2)
C1—C2—C19—O4	60.4 (3)	C28—C29—C46—O10	52.2 (3)
C8—C7—C21—C23	−98.9 (3)	C35—C34—C48—C50	−96.5 (4)
C3—C7—C21—C23	83.1 (3)	C30—C34—C48—C50	75.9 (4)
C8—C7—C21—C22	25.8 (4)	C35—C34—C48—C49	136.2 (3)
C3—C7—C21—C22	−152.2 (3)	C30—C34—C48—C49	−51.5 (4)
C26—O6—C25—O5	−0.1 (4)	C53—O12—C52—O11	−3.5 (4)
C26—O6—C25—C13	177.5 (3)	C53—O12—C52—C40	174.3 (2)
C27—C13—C25—O5	−132.4 (3)	C54—C40—C52—O11	−130.0 (3)
C14—C13—C25—O5	109.2 (3)	C41—C40—C52—O11	111.8 (3)
C11—C13—C25—O5	−8.0 (4)	C38—C40—C52—O11	−6.2 (4)
C27—C13—C25—O6	50.2 (3)	C54—C40—C52—O12	52.3 (3)
C14—C13—C25—O6	−68.2 (3)	C41—C40—C52—O12	−65.8 (3)
C11—C13—C25—O6	174.5 (2)	C38—C40—C52—O12	176.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O11ⁱ	1.00	2.47	3.357 (3)	147
C18—H18C···O3ⁱⁱ	0.98	2.56	3.377 (4)	141
C26—H26C···O1ⁱⁱⁱ	0.98	2.51	3.389 (4)	149
C29—H29···O5	1.00	2.49	3.386 (3)	150
C53—H53C···O9^iv	0.98	2.60	3.513 (4)	156

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x+1, y+1/2, −z+1; (iv) −x+2, y−1/2, −z+2.

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