Cannabidiol revisited

Mayr, T.; Grassl, T.; Korber, N.; Christoffel, V.; Bodensteiner, M.

doi:10.1107/S2414314617002760

Cannabidiol revisited

T. Mayr, T. Grassl, N. Korber, V. Christoffel and M. Bodensteiner

The crystal structure of cannabidiol, C₂₁H₃₀O₂, {systematic name: 2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-enyl]-5-pentylbenzene-1,3-diol}, was determined earlier by Jones et al. [(1977). Acta Cryst. B33, 3211–3214] and Ottersen & Rosenqvist [(1977). Acta Chem. Scand. B31, 749–755]. In both investigations, the absolute configuration is given as R,R, referring to Mechoulam et al. [(1967.J. Am. Chem. Soc. 89, 4552–4554]. In the latter, the absolute configuration was identified by chemical means. Using the advantages of modern single-crystal X-ray diffractometers such as area detectors and high-intensity radiation sources, a high-quality structure determination including the absolute configuration was possible and is shown in this work. Furthermore, the rather uncommon Cu Kβ wavelength radiation was applied for the structure determination, which confirmed the absolute structure to be R,R.

Keywords: crystal structure; cannabidiol; Cu Kβ radiation; absolute structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314617002760/su4129sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2414314617002760/su4129Isup2.hkl Contains datablock I

CCDC reference: 1533487

checkCIF report

Key indicators

Single-crystal X-ray study
T = 123 K
Mean (C-C) = 0.002 Å
R factor = 0.032
wR factor = 0.088
Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level A
RADNT01_ALERT_1_A  The radiation type should contain one of the following
            *  'Cu K\a'
            *  'Mo K\a'
            *  'Ag K\a'
            *  'Ga K\a'
            *  neutron
            *  synchrotron

Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor       O1     --  H1     ...     Please Check
PLAT420_ALERT_2_B D-H Without Acceptor       O2     --  H2     ...     Please Check
PLAT420_ALERT_2_B D-H Without Acceptor       O4     --  H4     ...     Please Check

Alert level C
PLAT222_ALERT_3_C Non-Solvent Resd 1   H Uiso(max)/Uiso(min) Range        4.2 Ratio
PLAT390_ALERT_3_C Deviating Methyl C15     X-C-H Bond Angle ......        117 Degree
PLAT390_ALERT_3_C Deviating Methyl C43     X-C-H Bond Angle ......        116 Degree

Alert level G
ABSMU01_ALERT_1_G  Calculation of _exptl_absorpt_correction_mu
                not performed for this radiation type.
PLAT092_ALERT_4_G Check: Wavelength given is not Cu,Ga,Mo,Ag,In Ka    1.39222 Ang.
PLAT142_ALERT_4_G s.u. on b - Axis Small or Missing ..............    0.00010 Ang.
PLAT791_ALERT_4_G The Model has Chirality at C16     (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C21     (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C37     (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C38     (Chiral SPGR)          R Verify
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         41 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         19 Note
PLAT982_ALERT_1_G The  C-f'=     0.016 Deviates from the  IT-value      0.015 Check
PLAT982_ALERT_1_G The  O-f'=     0.044 Deviates from the  IT-value      0.042 Check

   1 ALERT level A = Most likely a serious problem - resolve or explain
   3 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  11 ALERT level G = General information/check it is not something unexpected

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

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

2-[(1R,6R)-3-Methyl-6-(prop-1-en-2-yl)cyclohex-2-enyl]-5-pentylbenzene-1,3-diol top

Crystal data top

C₂₁H₃₀O₂	D_x = 1.101 Mg m⁻³
M_r = 314.45	Melting point = 339–340 K
Monoclinic, P2₁	Cu Kβ radiation, λ = 1.39222 Å
a = 10.4395 (1) Å	Cell parameters from 54306 reflections
b = 10.8739 (1) Å	θ = 3.6–74.8°
c = 16.7853 (2) Å	µ = 0.39 mm⁻¹
β = 95.448 (1)°	T = 123 K
V = 1896.83 (3) Å³	Prism, clear colourless
Z = 4	0.28 × 0.16 × 0.15 mm
F(000) = 688

Data collection top

Agilent GV1000, TitanS2 diffractometer	10203 independent reflections
Radiation source: gradient vaccum rotating-anode X-ray tube, GV1000 (Cu) X-ray Source	9859 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.044
Detector resolution: 4.1818 pixels mm^-1	θ_max = 75.3°, θ_min = 2.4°
ω scans	h = −14→14
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2015)	k = −15→14
T_min = 0.996, T_max = 0.997	l = −23→23
85198 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F² > 2σ(F²)] = 0.032	w = 1/[σ²(F_o²) + (0.0493P)² + 0.1553P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.088	(Δ/σ)_max < 0.001
S = 1.03	Δρ_max = 0.23 e Å⁻³
10203 reflections	Δρ_min = −0.13 e Å⁻³
655 parameters	Absolute structure: Flack x determined using 4335 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013
1 restraint	Absolute structure parameter: −0.03 (6)
Primary atom site location: dual

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O2	0.45873 (9)	0.27113 (11)	0.68801 (7)	0.0350 (2)
O3	0.22910 (10)	0.31909 (11)	0.75679 (7)	0.0361 (2)
O4	−0.01007 (11)	0.64952 (12)	0.85698 (7)	0.0370 (2)
O1	0.89037 (10)	0.39186 (12)	0.65474 (7)	0.0401 (2)
C7	0.56191 (12)	0.35049 (13)	0.70250 (8)	0.0280 (2)
C27	0.11199 (12)	0.47899 (13)	0.81028 (7)	0.0276 (2)
C28	0.06220 (12)	0.59824 (14)	0.80142 (8)	0.0298 (2)
C26	0.18235 (11)	0.43560 (13)	0.74901 (7)	0.0285 (2)
C6	0.68036 (12)	0.32428 (13)	0.67315 (7)	0.0272 (2)
C5	0.77497 (12)	0.41511 (14)	0.68514 (8)	0.0297 (2)
C29	0.08240 (13)	0.67195 (14)	0.73595 (9)	0.0337 (3)
C41	−0.10203 (14)	0.40126 (16)	0.96293 (9)	0.0360 (3)
C37	0.09170 (12)	0.39998 (14)	0.88271 (7)	0.0290 (2)
C9	0.63810 (13)	0.54375 (14)	0.75803 (8)	0.0317 (3)
C16	0.70534 (12)	0.20447 (14)	0.63181 (8)	0.0301 (2)
C8	0.54143 (13)	0.45499 (14)	0.74650 (8)	0.0309 (2)
C10	0.75383 (13)	0.52378 (14)	0.72519 (8)	0.0328 (3)
C38	0.16926 (12)	0.44801 (14)	0.96000 (8)	0.0309 (3)
C31	0.20157 (13)	0.50812 (15)	0.68246 (8)	0.0327 (3)
C42	−0.05071 (13)	0.39038 (15)	0.89332 (8)	0.0329 (3)
C30	0.15332 (13)	0.62697 (15)	0.67583 (8)	0.0334 (3)
C17	0.61190 (15)	0.18610 (16)	0.55797 (8)	0.0359 (3)
C18	0.56273 (18)	0.07793 (18)	0.53315 (9)	0.0432 (4)
C44	0.31309 (14)	0.43548 (17)	0.95708 (9)	0.0381 (3)
C21	0.70272 (14)	0.09214 (15)	0.68849 (9)	0.0352 (3)
C22	0.80132 (16)	0.10349 (17)	0.76024 (11)	0.0426 (3)
C11	0.61657 (16)	0.66019 (16)	0.80361 (10)	0.0390 (3)
C39	0.12060 (15)	0.38200 (17)	1.03236 (8)	0.0374 (3)
C32	0.17722 (17)	0.70713 (19)	0.60483 (10)	0.0434 (4)
C12	0.49874 (18)	0.73187 (17)	0.77039 (10)	0.0429 (3)
C33	0.0558 (2)	0.74656 (19)	0.55280 (11)	0.0475 (4)
C40	−0.01885 (16)	0.41677 (18)	1.04074 (9)	0.0408 (3)
C13	0.47857 (18)	0.85021 (16)	0.81437 (10)	0.0414 (3)
C23	0.7641 (2)	0.12371 (19)	0.83228 (11)	0.0498 (4)
C20	0.7152 (2)	−0.02482 (18)	0.63891 (13)	0.0494 (4)
C43	−0.24537 (17)	0.3974 (2)	0.96703 (12)	0.0503 (4)
C34	−0.01477 (18)	0.64082 (19)	0.50915 (11)	0.0449 (4)
C14	0.3597 (2)	0.9199 (2)	0.78214 (16)	0.0630 (6)
C25	0.4721 (3)	0.0678 (3)	0.45807 (12)	0.0607 (6)
C45	0.36871 (18)	0.3090 (2)	0.95561 (14)	0.0528 (5)
C46	0.38685 (19)	0.5344 (3)	0.95736 (16)	0.0603 (5)
C19	0.5994 (2)	−0.03921 (19)	0.57671 (13)	0.0540 (4)
C15	0.3401 (2)	1.0401 (2)	0.82410 (13)	0.0543 (5)
C35	−0.1338 (2)	0.6820 (2)	0.45576 (15)	0.0578 (5)
C24	0.9415 (2)	0.0943 (3)	0.74624 (18)	0.0663 (6)
C36	−0.1995 (2)	0.5757 (3)	0.40974 (17)	0.0636 (6)
H40A	−0.025 (2)	0.504 (2)	1.0609 (14)	0.043 (5)*
H38	0.1488 (18)	0.538 (2)	0.9650 (11)	0.027 (4)*
H8	0.459 (2)	0.466 (2)	0.7688 (13)	0.042 (5)*
H33A	−0.005 (3)	0.789 (3)	0.5860 (17)	0.062 (7)*
H39A	0.177 (2)	0.401 (2)	1.0813 (13)	0.041 (5)*
H21	0.617 (2)	0.089 (2)	0.7084 (12)	0.033 (5)*
H33B	0.085 (3)	0.807 (3)	0.5148 (17)	0.063 (8)*
H19A	0.527 (3)	−0.071 (3)	0.6008 (16)	0.060 (7)*
H42	−0.107 (2)	0.374 (2)	0.8461 (12)	0.035 (5)*
H32A	0.235 (3)	0.665 (3)	0.5677 (16)	0.055 (7)*
H37	0.1249 (18)	0.315 (2)	0.8712 (11)	0.030 (4)*
H16	0.7917 (18)	0.210 (2)	0.6121 (11)	0.030 (4)*
H39B	0.127 (2)	0.290 (3)	1.0247 (14)	0.046 (6)*
H40B	−0.055 (2)	0.365 (3)	1.0835 (15)	0.050 (6)*
H17	0.591 (2)	0.264 (3)	0.5272 (15)	0.047 (6)*
H31	0.251 (2)	0.476 (2)	0.6408 (13)	0.043 (5)*
H45A	0.356 (4)	0.256 (4)	1.004 (2)	0.092 (11)*
H20A	0.798 (3)	−0.018 (3)	0.6132 (16)	0.060 (7)*
H34A	−0.042 (2)	0.578 (3)	0.5498 (15)	0.050 (6)*
H10	0.823 (2)	0.585 (2)	0.7311 (13)	0.039 (5)*
H11A	0.608 (2)	0.639 (3)	0.8615 (15)	0.050 (6)*
H13A	0.550 (3)	0.902 (3)	0.8117 (18)	0.069 (8)*
H1	0.943 (3)	0.444 (3)	0.6727 (15)	0.054 (7)*
H13B	0.473 (3)	0.835 (3)	0.8723 (17)	0.058 (7)*
H29	0.049 (2)	0.756 (2)	0.7327 (13)	0.043 (6)*
H24A	0.961 (3)	0.150 (3)	0.7046 (19)	0.070 (8)*
H24B	0.993 (3)	0.106 (3)	0.793 (2)	0.077 (9)*
H3	0.290 (2)	0.307 (2)	0.7284 (14)	0.046 (6)*
H35A	−0.111 (3)	0.746 (3)	0.4193 (18)	0.063 (8)*
H35B	−0.190 (3)	0.721 (3)	0.4888 (19)	0.068 (8)*
H46A	0.483 (3)	0.524 (3)	0.9616 (18)	0.071 (9)*
H43A	−0.283 (3)	0.469 (3)	0.9898 (19)	0.074 (9)*
H12A	0.416 (3)	0.679 (3)	0.7686 (19)	0.073 (9)*
H46B	0.344 (4)	0.613 (4)	0.958 (2)	0.090 (11)*
H12B	0.499 (3)	0.750 (3)	0.7153 (19)	0.070 (8)*
H15A	0.342 (3)	1.031 (3)	0.883 (2)	0.080 (10)*
H19B	0.617 (3)	−0.104 (3)	0.537 (2)	0.074 (9)*
H32B	0.223 (3)	0.781 (3)	0.6257 (17)	0.064 (8)*
H14A	0.365 (4)	0.935 (4)	0.720 (3)	0.113 (14)*
H34B	0.048 (2)	0.596 (3)	0.4745 (15)	0.052 (6)*
H20B	0.721 (3)	−0.098 (3)	0.6747 (16)	0.057 (7)*
H43B	−0.293 (3)	0.386 (3)	0.9146 (17)	0.060 (7)*
H23A	0.676 (3)	0.132 (3)	0.8403 (16)	0.059 (7)*
H23B	0.818 (3)	0.130 (3)	0.8784 (17)	0.061 (7)*
H2	0.475 (2)	0.223 (2)	0.6496 (14)	0.044 (5)*
H4	−0.036 (3)	0.593 (3)	0.8864 (16)	0.054 (7)*
H43C	−0.264 (3)	0.331 (3)	1.0030 (19)	0.073 (9)*
H25A	0.443 (3)	0.156 (4)	0.438 (2)	0.075 (9)*
H15B	0.415 (3)	1.097 (4)	0.815 (2)	0.082 (10)*
H36A	−0.142 (3)	0.538 (3)	0.3720 (17)	0.063 (8)*
H25B	0.512 (3)	0.020 (3)	0.4207 (19)	0.069 (8)*
H25C	0.401 (3)	0.024 (3)	0.4684 (19)	0.073 (9)*
H45B	0.463 (3)	0.312 (3)	0.9515 (18)	0.068 (8)*
H11B	0.692 (3)	0.713 (3)	0.8057 (18)	0.072 (8)*
H45C	0.331 (3)	0.264 (3)	0.914 (2)	0.078 (9)*
H36B	−0.222 (3)	0.515 (4)	0.448 (2)	0.076 (9)*
H14B	0.280 (5)	0.877 (5)	0.788 (3)	0.125 (16)*
H36C	−0.284 (4)	0.611 (4)	0.377 (2)	0.088 (11)*
H24C	0.955 (4)	0.003 (4)	0.723 (2)	0.093 (11)*
H15C	0.261 (4)	1.085 (4)	0.808 (2)	0.098 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0289 (4)	0.0337 (5)	0.0438 (5)	−0.0053 (4)	0.0102 (4)	−0.0110 (4)
O3	0.0349 (5)	0.0343 (6)	0.0409 (5)	0.0056 (4)	0.0121 (4)	−0.0004 (4)
O4	0.0416 (5)	0.0330 (6)	0.0380 (5)	0.0046 (4)	0.0113 (4)	−0.0038 (4)
O1	0.0277 (4)	0.0454 (7)	0.0481 (6)	−0.0063 (4)	0.0074 (4)	−0.0059 (5)
C7	0.0276 (5)	0.0280 (6)	0.0281 (5)	−0.0018 (4)	0.0016 (4)	−0.0003 (4)
C27	0.0256 (5)	0.0302 (6)	0.0271 (5)	−0.0014 (4)	0.0027 (4)	−0.0013 (4)
C28	0.0273 (5)	0.0313 (7)	0.0309 (5)	−0.0008 (5)	0.0034 (4)	−0.0028 (5)
C26	0.0237 (5)	0.0316 (7)	0.0302 (5)	−0.0003 (4)	0.0027 (4)	−0.0026 (5)
C6	0.0277 (5)	0.0279 (6)	0.0258 (5)	0.0000 (4)	0.0018 (4)	0.0007 (4)
C5	0.0264 (5)	0.0331 (7)	0.0292 (5)	−0.0011 (5)	0.0003 (4)	0.0028 (5)
C29	0.0312 (6)	0.0311 (7)	0.0386 (6)	−0.0008 (5)	0.0028 (5)	0.0025 (5)
C41	0.0335 (6)	0.0392 (8)	0.0361 (6)	−0.0019 (5)	0.0077 (5)	0.0030 (6)
C37	0.0297 (5)	0.0301 (7)	0.0272 (5)	−0.0006 (5)	0.0032 (4)	−0.0002 (4)
C9	0.0332 (6)	0.0290 (7)	0.0314 (6)	0.0017 (5)	−0.0052 (5)	−0.0027 (5)
C16	0.0300 (6)	0.0299 (7)	0.0312 (5)	0.0007 (5)	0.0075 (4)	−0.0016 (5)
C8	0.0294 (5)	0.0315 (7)	0.0315 (5)	0.0020 (5)	0.0014 (4)	−0.0037 (5)
C10	0.0300 (6)	0.0306 (7)	0.0361 (6)	−0.0033 (5)	−0.0049 (5)	−0.0003 (5)
C38	0.0311 (6)	0.0330 (7)	0.0282 (5)	−0.0004 (5)	0.0016 (4)	−0.0004 (5)
C31	0.0277 (5)	0.0415 (8)	0.0294 (5)	−0.0034 (5)	0.0061 (4)	−0.0021 (5)
C42	0.0314 (6)	0.0358 (7)	0.0315 (6)	−0.0042 (5)	0.0026 (5)	0.0016 (5)
C30	0.0295 (6)	0.0394 (8)	0.0311 (6)	−0.0056 (5)	0.0015 (4)	0.0042 (5)
C17	0.0409 (7)	0.0392 (8)	0.0285 (6)	−0.0005 (6)	0.0084 (5)	−0.0053 (5)
C18	0.0503 (8)	0.0465 (10)	0.0342 (6)	−0.0056 (7)	0.0112 (6)	−0.0129 (6)
C44	0.0331 (6)	0.0473 (9)	0.0332 (6)	0.0020 (6)	−0.0008 (5)	−0.0012 (6)
C21	0.0356 (6)	0.0301 (7)	0.0405 (7)	0.0012 (5)	0.0070 (5)	0.0011 (5)
C22	0.0397 (7)	0.0357 (8)	0.0513 (8)	0.0028 (6)	−0.0013 (6)	0.0103 (7)
C11	0.0403 (7)	0.0319 (8)	0.0426 (7)	0.0032 (6)	−0.0069 (6)	−0.0098 (6)
C39	0.0414 (7)	0.0435 (9)	0.0271 (5)	0.0016 (6)	0.0020 (5)	0.0031 (5)
C32	0.0429 (7)	0.0482 (10)	0.0393 (7)	−0.0094 (7)	0.0051 (6)	0.0112 (7)
C12	0.0493 (8)	0.0349 (8)	0.0423 (8)	0.0082 (6)	−0.0073 (6)	−0.0079 (6)
C33	0.0572 (9)	0.0442 (10)	0.0403 (8)	−0.0047 (7)	0.0011 (7)	0.0111 (7)
C40	0.0433 (7)	0.0491 (10)	0.0311 (6)	−0.0003 (6)	0.0093 (5)	0.0014 (6)
C13	0.0501 (8)	0.0306 (8)	0.0427 (7)	0.0049 (6)	0.0006 (6)	−0.0046 (6)
C23	0.0590 (10)	0.0435 (10)	0.0448 (8)	−0.0022 (8)	−0.0065 (7)	0.0068 (7)
C20	0.0574 (10)	0.0300 (8)	0.0621 (10)	0.0052 (7)	0.0128 (8)	−0.0040 (7)
C43	0.0355 (7)	0.0689 (13)	0.0484 (8)	−0.0037 (8)	0.0136 (6)	0.0041 (9)
C34	0.0488 (8)	0.0426 (9)	0.0429 (8)	−0.0007 (7)	0.0022 (6)	0.0068 (7)
C14	0.0641 (12)	0.0452 (12)	0.0756 (14)	0.0181 (9)	−0.0141 (10)	−0.0167 (10)
C25	0.0731 (13)	0.0685 (15)	0.0401 (8)	−0.0155 (11)	0.0037 (9)	−0.0236 (9)
C45	0.0413 (8)	0.0558 (12)	0.0591 (10)	0.0145 (8)	−0.0063 (7)	−0.0074 (9)
C46	0.0366 (8)	0.0613 (14)	0.0833 (15)	−0.0080 (8)	0.0070 (9)	0.0000 (11)
C19	0.0686 (12)	0.0369 (10)	0.0577 (10)	−0.0088 (8)	0.0122 (9)	−0.0156 (8)
C15	0.0680 (12)	0.0384 (10)	0.0581 (10)	0.0133 (9)	0.0143 (9)	−0.0006 (8)
C35	0.0599 (11)	0.0511 (12)	0.0593 (11)	0.0042 (9)	−0.0112 (9)	0.0052 (9)
C24	0.0396 (9)	0.0783 (17)	0.0794 (15)	0.0108 (10)	−0.0016 (9)	0.0226 (14)
C36	0.0584 (12)	0.0607 (14)	0.0692 (13)	0.0005 (10)	−0.0070 (10)	0.0006 (11)

Geometric parameters (Å, º) top

O2—C7	1.3836 (16)	C11—H11B	0.98 (3)
O2—H2	0.86 (3)	C39—C40	1.523 (2)
O3—C26	1.3595 (18)	C39—H39A	0.98 (2)
O3—H3	0.84 (3)	C39—H39B	1.02 (3)
O4—C28	1.3723 (16)	C32—C33	1.531 (3)
O4—H4	0.85 (3)	C32—H32A	1.02 (3)
O1—C5	1.3756 (17)	C32—H32B	0.98 (3)
O1—H1	0.83 (3)	C12—C13	1.508 (2)
C7—C6	1.4031 (18)	C12—H12A	1.03 (3)
C7—C8	1.3829 (19)	C12—H12B	0.95 (3)
C27—C28	1.400 (2)	C33—C34	1.516 (3)
C27—C26	1.4011 (17)	C33—H33A	1.00 (3)
C27—C37	1.5198 (18)	C33—H33B	0.99 (3)
C28—C29	1.392 (2)	C40—H40A	1.01 (3)
C26—C31	1.3973 (19)	C40—H40B	1.01 (3)
C6—C5	1.3978 (18)	C13—C14	1.510 (3)
C6—C16	1.510 (2)	C13—H13A	0.94 (3)
C5—C10	1.388 (2)	C13—H13B	0.99 (3)
C29—C30	1.395 (2)	C23—H23A	0.95 (3)
C29—H29	0.98 (3)	C23—H23B	0.92 (3)
C41—C42	1.3361 (19)	C20—C19	1.529 (3)
C41—C40	1.508 (2)	C20—H20A	1.00 (3)
C41—C43	1.505 (2)	C20—H20B	1.00 (3)
C37—C38	1.5530 (17)	C43—H43A	0.96 (4)
C37—C42	1.5176 (18)	C43—H43B	0.98 (3)
C37—H37	1.01 (2)	C43—H43C	0.97 (4)
C9—C8	1.397 (2)	C34—C35	1.529 (3)
C9—C10	1.392 (2)	C34—H34A	1.02 (3)
C9—C11	1.507 (2)	C34—H34B	1.04 (3)
C16—C17	1.516 (2)	C14—C15	1.507 (3)
C16—C21	1.550 (2)	C14—H14A	1.06 (4)
C16—H16	0.991 (19)	C14—H14B	0.97 (5)
C8—H8	0.98 (2)	C25—H25A	1.05 (4)
C10—H10	0.98 (2)	C25—H25B	0.94 (3)
C38—C44	1.5131 (19)	C25—H25C	0.91 (4)
C38—C39	1.5380 (19)	C45—H45A	1.01 (4)
C38—H38	1.01 (2)	C45—H45B	1.00 (3)
C31—C30	1.388 (2)	C45—H45C	0.91 (4)
C31—H31	0.97 (2)	C46—H46A	1.01 (3)
C42—H42	0.96 (2)	C46—H46B	0.97 (4)
C30—C32	1.516 (2)	C19—H19A	0.95 (3)
C17—C18	1.334 (2)	C19—H19B	0.99 (3)
C17—H17	1.01 (3)	C15—H15A	1.00 (3)
C18—C25	1.506 (3)	C15—H15B	1.03 (4)
C18—C19	1.500 (3)	C15—H15C	0.97 (4)
C44—C45	1.494 (3)	C35—C36	1.517 (4)
C44—C46	1.323 (3)	C35—H35A	0.97 (3)
C21—C22	1.513 (2)	C35—H35B	0.94 (3)
C21—C20	1.532 (2)	C24—H24A	0.96 (3)
C21—H21	0.99 (2)	C24—H24B	0.91 (4)
C22—C23	1.323 (3)	C24—H24C	1.09 (4)
C22—C24	1.507 (3)	C36—H36A	1.00 (3)
C11—C12	1.517 (2)	C36—H36B	0.96 (4)
C11—H11A	1.01 (3)	C36—H36C	1.07 (4)

C7—O2—H2	107.9 (16)	C33—C32—H32B	109.2 (18)
C26—O3—H3	112.3 (18)	H32A—C32—H32B	106 (2)
C28—O4—H4	108.9 (19)	C11—C12—H12A	111.8 (19)
C5—O1—H1	108.4 (18)	C11—C12—H12B	112.7 (19)
O2—C7—C6	120.59 (12)	C13—C12—C11	113.86 (13)
C8—C7—O2	116.69 (12)	C13—C12—H12A	109.4 (18)
C8—C7—C6	122.72 (12)	C13—C12—H12B	108 (2)
C28—C27—C26	116.69 (12)	H12A—C12—H12B	100 (3)
C28—C27—C37	122.01 (11)	C32—C33—H33A	110.4 (16)
C26—C27—C37	121.29 (13)	C32—C33—H33B	105.3 (17)
O4—C28—C27	121.79 (13)	C34—C33—C32	113.65 (17)
O4—C28—C29	115.90 (13)	C34—C33—H33A	108.3 (18)
C29—C28—C27	122.32 (12)	C34—C33—H33B	111.2 (17)
O3—C26—C27	116.85 (12)	H33A—C33—H33B	108 (2)
O3—C26—C31	121.68 (12)	C41—C40—C39	111.66 (12)
C31—C26—C27	121.46 (13)	C41—C40—H40A	110.2 (13)
C7—C6—C16	122.20 (12)	C41—C40—H40B	109.2 (14)
C5—C6—C7	116.12 (12)	C39—C40—H40A	111.0 (13)
C5—C6—C16	121.68 (11)	C39—C40—H40B	110.6 (14)
O1—C5—C6	116.65 (13)	H40A—C40—H40B	103.9 (19)
O1—C5—C10	121.43 (13)	C12—C13—C14	113.65 (15)
C10—C5—C6	121.92 (12)	C12—C13—H13A	109.9 (19)
C28—C29—C30	119.97 (14)	C12—C13—H13B	111.2 (18)
C28—C29—H29	120.1 (13)	C14—C13—H13A	108 (2)
C30—C29—H29	119.9 (13)	C14—C13—H13B	108.2 (17)
C42—C41—C40	121.44 (13)	H13A—C13—H13B	105 (2)
C42—C41—C43	121.36 (14)	C22—C23—H23A	121.3 (17)
C43—C41—C40	117.19 (13)	C22—C23—H23B	124.9 (18)
C27—C37—C38	112.15 (11)	H23A—C23—H23B	114 (2)
C27—C37—H37	106.6 (11)	C21—C20—H20A	106.8 (18)
C38—C37—H37	107.8 (11)	C21—C20—H20B	109.9 (16)
C42—C37—C27	110.20 (11)	C19—C20—C21	110.68 (15)
C42—C37—C38	111.34 (10)	C19—C20—H20A	111.8 (16)
C42—C37—H37	108.5 (11)	C19—C20—H20B	109.1 (16)
C8—C9—C11	120.68 (13)	H20A—C20—H20B	108 (2)
C10—C9—C8	118.71 (13)	C41—C43—H43A	116 (2)
C10—C9—C11	120.60 (14)	C41—C43—H43B	112.6 (16)
C6—C16—C17	111.32 (12)	C41—C43—H43C	107.7 (19)
C6—C16—C21	112.57 (11)	H43A—C43—H43B	106 (3)
C6—C16—H16	107.6 (12)	H43A—C43—H43C	104 (3)
C17—C16—C21	110.52 (12)	H43B—C43—H43C	111 (3)
C17—C16—H16	105.6 (11)	C33—C34—C35	113.08 (17)
C21—C16—H16	108.9 (12)	C33—C34—H34A	109.5 (14)
C7—C8—C9	119.71 (12)	C33—C34—H34B	108.6 (15)
C7—C8—H8	119.2 (14)	C35—C34—H34A	109.1 (14)
C9—C8—H8	121.1 (14)	C35—C34—H34B	109.3 (14)
C5—C10—C9	120.58 (13)	H34A—C34—H34B	107 (2)
C5—C10—H10	118.7 (13)	C13—C14—H14A	108 (2)
C9—C10—H10	120.7 (13)	C13—C14—H14B	114 (3)
C37—C38—H38	107.4 (11)	C15—C14—C13	114.30 (18)
C44—C38—C37	112.51 (11)	C15—C14—H14A	110 (3)
C44—C38—C39	112.76 (12)	C15—C14—H14B	103 (3)
C44—C38—H38	108.0 (11)	H14A—C14—H14B	107 (4)
C39—C38—C37	108.52 (11)	C18—C25—H25A	110.3 (18)
C39—C38—H38	107.4 (11)	C18—C25—H25B	108.3 (19)
C26—C31—H31	119.9 (15)	C18—C25—H25C	110 (2)
C30—C31—C26	120.74 (12)	H25A—C25—H25B	115 (3)
C30—C31—H31	119.4 (15)	H25A—C25—H25C	108 (3)
C41—C42—C37	125.11 (12)	H25B—C25—H25C	105 (3)
C41—C42—H42	118.5 (13)	C44—C45—H45A	116 (2)
C37—C42—H42	116.4 (12)	C44—C45—H45B	111 (2)
C29—C30—C32	120.33 (15)	C44—C45—H45C	112 (2)
C31—C30—C29	118.81 (13)	H45A—C45—H45B	106 (3)
C31—C30—C32	120.86 (14)	H45A—C45—H45C	103 (3)
C16—C17—H17	113.6 (14)	H45B—C45—H45C	109 (3)
C18—C17—C16	124.76 (16)	C44—C46—H46A	119 (2)
C18—C17—H17	121.6 (14)	C44—C46—H46B	117 (2)
C17—C18—C25	121.23 (19)	H46A—C46—H46B	124 (3)
C17—C18—C19	121.57 (16)	C18—C19—C20	113.24 (16)
C19—C18—C25	117.16 (18)	C18—C19—H19A	109.6 (18)
C45—C44—C38	118.15 (15)	C18—C19—H19B	109 (2)
C46—C44—C38	120.39 (17)	C20—C19—H19A	110.7 (16)
C46—C44—C45	121.46 (17)	C20—C19—H19B	110.3 (19)
C16—C21—H21	107.7 (13)	H19A—C19—H19B	103 (3)
C22—C21—C16	111.96 (13)	C14—C15—H15A	113 (2)
C22—C21—C20	114.41 (15)	C14—C15—H15B	108 (2)
C22—C21—H21	107.7 (12)	C14—C15—H15C	117 (3)
C20—C21—C16	108.26 (13)	H15A—C15—H15B	105 (3)
C20—C21—H21	106.5 (13)	H15A—C15—H15C	105 (3)
C23—C22—C21	120.27 (16)	H15B—C15—H15C	107 (3)
C23—C22—C24	121.83 (19)	C34—C35—H35A	110.3 (17)
C24—C22—C21	117.87 (18)	C34—C35—H35B	107.5 (19)
C9—C11—C12	113.57 (12)	C36—C35—C34	112.3 (2)
C9—C11—H11A	109.0 (16)	C36—C35—H35A	110.5 (18)
C9—C11—H11B	110.9 (19)	C36—C35—H35B	112 (2)
C12—C11—H11A	109.1 (14)	H35A—C35—H35B	104 (3)
C12—C11—H11B	110 (2)	C22—C24—H24A	110.2 (18)
H11A—C11—H11B	104 (2)	C22—C24—H24B	111 (2)
C38—C39—H39A	110.1 (14)	C22—C24—H24C	106 (2)
C38—C39—H39B	109.3 (14)	H24A—C24—H24B	113 (3)
C40—C39—C38	110.32 (12)	H24A—C24—H24C	106 (3)
C40—C39—H39A	111.6 (13)	H24B—C24—H24C	110 (3)
C40—C39—H39B	109.4 (14)	C35—C36—H36A	111.6 (18)
H39A—C39—H39B	105.9 (19)	C35—C36—H36B	108 (2)
C30—C32—C33	114.85 (14)	C35—C36—H36C	108 (2)
C30—C32—H32A	112.2 (16)	H36A—C36—H36B	110 (3)
C30—C32—H32B	107.4 (17)	H36A—C36—H36C	109 (3)
C33—C32—H32A	106.6 (15)	H36B—C36—H36C	110 (3)

O2—C7—C6—C5	174.74 (12)	C9—C11—C12—C13	−178.47 (15)
O2—C7—C6—C16	−5.95 (19)	C16—C6—C5—O1	2.37 (18)
O2—C7—C8—C9	−175.02 (12)	C16—C6—C5—C10	−178.04 (12)
O3—C26—C31—C30	−179.81 (12)	C16—C17—C18—C25	−178.89 (16)
O4—C28—C29—C30	−179.15 (13)	C16—C17—C18—C19	−1.5 (3)
O1—C5—C10—C9	−177.67 (13)	C16—C21—C22—C23	109.34 (19)
C7—C6—C5—O1	−178.32 (12)	C16—C21—C22—C24	−69.1 (2)
C7—C6—C5—C10	1.27 (18)	C16—C21—C20—C19	−63.94 (19)
C7—C6—C16—C17	59.51 (16)	C8—C7—C6—C5	−5.08 (19)
C7—C6—C16—C21	−65.22 (16)	C8—C7—C6—C16	174.22 (12)
C27—C28—C29—C30	0.7 (2)	C8—C9—C10—C5	−3.1 (2)
C27—C26—C31—C30	1.3 (2)	C8—C9—C11—C12	−55.2 (2)
C27—C37—C38—C44	−67.06 (16)	C10—C9—C8—C7	−0.6 (2)
C27—C37—C38—C39	167.46 (12)	C10—C9—C11—C12	123.46 (16)
C27—C37—C42—C41	−135.63 (17)	C38—C37—C42—C41	−10.5 (2)
C28—C27—C26—O3	−178.98 (11)	C38—C39—C40—C41	50.55 (19)
C28—C27—C26—C31	−0.02 (18)	C31—C30—C32—C33	118.00 (18)
C28—C27—C37—C38	−70.38 (15)	C42—C41—C40—C39	−16.2 (2)
C28—C27—C37—C42	54.26 (16)	C42—C37—C38—C44	168.94 (13)
C28—C29—C30—C31	0.6 (2)	C42—C37—C38—C39	43.46 (16)
C28—C29—C30—C32	−179.24 (13)	C30—C32—C33—C34	−66.3 (2)
C26—C27—C28—O4	178.87 (12)	C17—C16—C21—C22	176.17 (13)
C26—C27—C28—C29	−0.96 (18)	C17—C16—C21—C20	49.14 (16)
C26—C27—C37—C38	109.37 (14)	C17—C18—C19—C20	−11.9 (3)
C26—C27—C37—C42	−125.99 (13)	C44—C38—C39—C40	169.73 (14)
C26—C31—C30—C29	−1.5 (2)	C21—C16—C17—C18	−18.05 (19)
C26—C31—C30—C32	178.27 (13)	C21—C20—C19—C18	44.8 (2)
C6—C7—C8—C9	4.8 (2)	C22—C21—C20—C19	170.46 (16)
C6—C5—C10—C9	2.8 (2)	C11—C9—C8—C7	178.12 (13)
C6—C16—C17—C18	−143.92 (15)	C11—C9—C10—C5	178.21 (13)
C6—C16—C21—C22	−58.66 (16)	C11—C12—C13—C14	−178.8 (2)
C6—C16—C21—C20	174.31 (13)	C39—C38—C44—C45	57.14 (19)
C5—C6—C16—C17	−121.22 (13)	C39—C38—C44—C46	−121.6 (2)
C5—C6—C16—C21	114.05 (13)	C32—C33—C34—C35	−178.50 (17)
C29—C30—C32—C33	−62.2 (2)	C12—C13—C14—C15	−178.5 (2)
C37—C27—C28—O4	−1.37 (19)	C33—C34—C35—C36	177.4 (2)
C37—C27—C28—C29	178.80 (12)	C40—C41—C42—C37	−4.0 (3)
C37—C27—C26—O3	1.26 (18)	C20—C21—C22—C23	−127.02 (19)
C37—C27—C26—C31	−179.78 (11)	C20—C21—C22—C24	54.5 (2)
C37—C38—C44—C45	−66.00 (18)	C43—C41—C42—C37	176.55 (17)
C37—C38—C44—C46	115.25 (19)	C43—C41—C40—C39	163.23 (17)
C37—C38—C39—C40	−64.94 (16)	C25—C18—C19—C20	165.63 (17)

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