organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146

Cannabidiol revisited

aInstitute for Inorganic Chemistry, University of Regensburg, 93040 Regensburg, Germany, bCSC - Christoffel Scientific Consulting, Bergstr. 11, 92369 Sengenthal, Germany, and cCentral Analytics Service, X-ray Crystallography Dept., University of Regensburg, 93040 Regensburg, Germany
*Correspondence e-mail: michael.bodensteiner@ur.de

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 4 February 2017; accepted 17 February 2017; online 28 February 2017)

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.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

The crystal structure of the title compound, Fig. 1[link], was determined in the course of investigations regarding the application of Cu Kβ radiation in single-crystal X-ray crystallography. Hence, the crystal was measured with this rather uncommon wavelength radiation.

[Figure 1]
Figure 1
The mol­ecular structure of the two independent mol­ecules of cannabidiol, with the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Differing in the freely rotatable unsaturated alkyl chain of the cannabidiol mol­ecule, two mol­ecules with different orientations of this side chain are found within the asymmetric unit (Fig. 1[link]). These independent mol­ecules are both found to have the R,R configuration, confirming earlier investigations by Jones et al. (1977[Jones, P. G., Falvello, L., Kennard, O., Sheldrick, G. M. & Mechoulam, R. (1977). Acta Cryst. B33, 3211-3214.]), Ottersen & Rosenqvist (1977[Ottersen, T. & Rosenqvist, E. (1977). Acta Chem. Scand. 31b, 749-755.]) and Mechoulam et al. (1967[Mechoulam, R., Braun, P. & Gaoni, Y. (1967). J. Am. Chem. Soc. 89, 4552-4554.]). In the latter, the absolute configuration was identified by chemical means.

Synthesis and crystallization

A crystal of cannabidiol was used as obtained from Trigal Pharma GmbH, Felix-Mottl-Str. 32, Vienna, Austria. The compound was recrystallized from n-heptane. A suitable crystal was selected using standard preparation techniques for non air- and moisture-sensitive samples and mounted on a MiTiGen-loop using mineral oil.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1[link].

Table 1
Experimental details

Crystal data
Chemical formula C21H30O2
Mr 314.45
Crystal system, space group Monoclinic, P21
Temperature (K) 123
a, b, c (Å) 10.4395 (1), 10.8739 (1), 16.7853 (2)
β (°) 95.448 (1)
V3) 1896.83 (3)
Z 4
Radiation type Cu Kβ
μ (mm−1) 0.39
Crystal size (mm) 0.28 × 0.16 × 0.15
 
Data collection
Diffractometer Agilent GV1000, TitanS2
Absorption correction Gaussian (CrysAlis PRO; Rigaku OD, 2015[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.])
Tmin, Tmax 0.996, 0.997
No. of measured, independent and observed [I > 2σ(I)] reflections 85198, 10203, 9859
Rint 0.044
(sin θ/λ)max−1) 0.695
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.088, 1.03
No. of reflections 10203
No. of parameters 655
No. of restraints 1
H-atom treatment All H-atom parameters refined
Δρmax, Δρmin (e Å−3) 0.23, −0.13
Absolute structure Flack x determined using 4335 quotients [(I+)−(I)]/[(I+)+(I)] (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.]
Absolute structure parameter −0.03 (6)
Computer programs: CrysAlis PRO (Rigaku OD, 2015[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]) and OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).

Structural data


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
C21H30O2Dx = 1.101 Mg m3
Mr = 314.45Melting point = 339–340 K
Monoclinic, P21Cu Kβ radiation, λ = 1.39222 Å
a = 10.4395 (1) ÅCell parameters from 54306 reflections
b = 10.8739 (1) Åθ = 3.6–74.8°
c = 16.7853 (2) ŵ = 0.39 mm1
β = 95.448 (1)°T = 123 K
V = 1896.83 (3) Å3Prism, clear colourless
Z = 40.28 × 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 Source9859 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.044
Detector resolution: 4.1818 pixels mm-1θmax = 75.3°, θmin = 2.4°
ω scansh = 1414
Absorption correction: gaussian
(CrysAlisPro; Rigaku OD, 2015)
k = 1514
Tmin = 0.996, Tmax = 0.997l = 2323
85198 measured reflections
Refinement top
Refinement on F2Hydrogen site location: difference Fourier map
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.032 w = 1/[σ2(Fo2) + (0.0493P)2 + 0.1553P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.088(Δ/σ)max < 0.001
S = 1.03Δρmax = 0.23 e Å3
10203 reflectionsΔρmin = 0.13 e Å3
655 parametersAbsolute structure: Flack x determined using 4335 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013
1 restraintAbsolute 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
xyzUiso*/Ueq
O20.45873 (9)0.27113 (11)0.68801 (7)0.0350 (2)
O30.22910 (10)0.31909 (11)0.75679 (7)0.0361 (2)
O40.01007 (11)0.64952 (12)0.85698 (7)0.0370 (2)
O10.89037 (10)0.39186 (12)0.65474 (7)0.0401 (2)
C70.56191 (12)0.35049 (13)0.70250 (8)0.0280 (2)
C270.11199 (12)0.47899 (13)0.81028 (7)0.0276 (2)
C280.06220 (12)0.59824 (14)0.80142 (8)0.0298 (2)
C260.18235 (11)0.43560 (13)0.74901 (7)0.0285 (2)
C60.68036 (12)0.32428 (13)0.67315 (7)0.0272 (2)
C50.77497 (12)0.41511 (14)0.68514 (8)0.0297 (2)
C290.08240 (13)0.67195 (14)0.73595 (9)0.0337 (3)
C410.10203 (14)0.40126 (16)0.96293 (9)0.0360 (3)
C370.09170 (12)0.39998 (14)0.88271 (7)0.0290 (2)
C90.63810 (13)0.54375 (14)0.75803 (8)0.0317 (3)
C160.70534 (12)0.20447 (14)0.63181 (8)0.0301 (2)
C80.54143 (13)0.45499 (14)0.74650 (8)0.0309 (2)
C100.75383 (13)0.52378 (14)0.72519 (8)0.0328 (3)
C380.16926 (12)0.44801 (14)0.96000 (8)0.0309 (3)
C310.20157 (13)0.50812 (15)0.68246 (8)0.0327 (3)
C420.05071 (13)0.39038 (15)0.89332 (8)0.0329 (3)
C300.15332 (13)0.62697 (15)0.67583 (8)0.0334 (3)
C170.61190 (15)0.18610 (16)0.55797 (8)0.0359 (3)
C180.56273 (18)0.07793 (18)0.53315 (9)0.0432 (4)
C440.31309 (14)0.43548 (17)0.95708 (9)0.0381 (3)
C210.70272 (14)0.09214 (15)0.68849 (9)0.0352 (3)
C220.80132 (16)0.10349 (17)0.76024 (11)0.0426 (3)
C110.61657 (16)0.66019 (16)0.80361 (10)0.0390 (3)
C390.12060 (15)0.38200 (17)1.03236 (8)0.0374 (3)
C320.17722 (17)0.70713 (19)0.60483 (10)0.0434 (4)
C120.49874 (18)0.73187 (17)0.77039 (10)0.0429 (3)
C330.0558 (2)0.74656 (19)0.55280 (11)0.0475 (4)
C400.01885 (16)0.41677 (18)1.04074 (9)0.0408 (3)
C130.47857 (18)0.85021 (16)0.81437 (10)0.0414 (3)
C230.7641 (2)0.12371 (19)0.83228 (11)0.0498 (4)
C200.7152 (2)0.02482 (18)0.63891 (13)0.0494 (4)
C430.24537 (17)0.3974 (2)0.96703 (12)0.0503 (4)
C340.01477 (18)0.64082 (19)0.50915 (11)0.0449 (4)
C140.3597 (2)0.9199 (2)0.78214 (16)0.0630 (6)
C250.4721 (3)0.0678 (3)0.45807 (12)0.0607 (6)
C450.36871 (18)0.3090 (2)0.95561 (14)0.0528 (5)
C460.38685 (19)0.5344 (3)0.95736 (16)0.0603 (5)
C190.5994 (2)0.03921 (19)0.57671 (13)0.0540 (4)
C150.3401 (2)1.0401 (2)0.82410 (13)0.0543 (5)
C350.1338 (2)0.6820 (2)0.45576 (15)0.0578 (5)
C240.9415 (2)0.0943 (3)0.74624 (18)0.0663 (6)
C360.1995 (2)0.5757 (3)0.40974 (17)0.0636 (6)
H40A0.025 (2)0.504 (2)1.0609 (14)0.043 (5)*
H380.1488 (18)0.538 (2)0.9650 (11)0.027 (4)*
H80.459 (2)0.466 (2)0.7688 (13)0.042 (5)*
H33A0.005 (3)0.789 (3)0.5860 (17)0.062 (7)*
H39A0.177 (2)0.401 (2)1.0813 (13)0.041 (5)*
H210.617 (2)0.089 (2)0.7084 (12)0.033 (5)*
H33B0.085 (3)0.807 (3)0.5148 (17)0.063 (8)*
H19A0.527 (3)0.071 (3)0.6008 (16)0.060 (7)*
H420.107 (2)0.374 (2)0.8461 (12)0.035 (5)*
H32A0.235 (3)0.665 (3)0.5677 (16)0.055 (7)*
H370.1249 (18)0.315 (2)0.8712 (11)0.030 (4)*
H160.7917 (18)0.210 (2)0.6121 (11)0.030 (4)*
H39B0.127 (2)0.290 (3)1.0247 (14)0.046 (6)*
H40B0.055 (2)0.365 (3)1.0835 (15)0.050 (6)*
H170.591 (2)0.264 (3)0.5272 (15)0.047 (6)*
H310.251 (2)0.476 (2)0.6408 (13)0.043 (5)*
H45A0.356 (4)0.256 (4)1.004 (2)0.092 (11)*
H20A0.798 (3)0.018 (3)0.6132 (16)0.060 (7)*
H34A0.042 (2)0.578 (3)0.5498 (15)0.050 (6)*
H100.823 (2)0.585 (2)0.7311 (13)0.039 (5)*
H11A0.608 (2)0.639 (3)0.8615 (15)0.050 (6)*
H13A0.550 (3)0.902 (3)0.8117 (18)0.069 (8)*
H10.943 (3)0.444 (3)0.6727 (15)0.054 (7)*
H13B0.473 (3)0.835 (3)0.8723 (17)0.058 (7)*
H290.049 (2)0.756 (2)0.7327 (13)0.043 (6)*
H24A0.961 (3)0.150 (3)0.7046 (19)0.070 (8)*
H24B0.993 (3)0.106 (3)0.793 (2)0.077 (9)*
H30.290 (2)0.307 (2)0.7284 (14)0.046 (6)*
H35A0.111 (3)0.746 (3)0.4193 (18)0.063 (8)*
H35B0.190 (3)0.721 (3)0.4888 (19)0.068 (8)*
H46A0.483 (3)0.524 (3)0.9616 (18)0.071 (9)*
H43A0.283 (3)0.469 (3)0.9898 (19)0.074 (9)*
H12A0.416 (3)0.679 (3)0.7686 (19)0.073 (9)*
H46B0.344 (4)0.613 (4)0.958 (2)0.090 (11)*
H12B0.499 (3)0.750 (3)0.7153 (19)0.070 (8)*
H15A0.342 (3)1.031 (3)0.883 (2)0.080 (10)*
H19B0.617 (3)0.104 (3)0.537 (2)0.074 (9)*
H32B0.223 (3)0.781 (3)0.6257 (17)0.064 (8)*
H14A0.365 (4)0.935 (4)0.720 (3)0.113 (14)*
H34B0.048 (2)0.596 (3)0.4745 (15)0.052 (6)*
H20B0.721 (3)0.098 (3)0.6747 (16)0.057 (7)*
H43B0.293 (3)0.386 (3)0.9146 (17)0.060 (7)*
H23A0.676 (3)0.132 (3)0.8403 (16)0.059 (7)*
H23B0.818 (3)0.130 (3)0.8784 (17)0.061 (7)*
H20.475 (2)0.223 (2)0.6496 (14)0.044 (5)*
H40.036 (3)0.593 (3)0.8864 (16)0.054 (7)*
H43C0.264 (3)0.331 (3)1.0030 (19)0.073 (9)*
H25A0.443 (3)0.156 (4)0.438 (2)0.075 (9)*
H15B0.415 (3)1.097 (4)0.815 (2)0.082 (10)*
H36A0.142 (3)0.538 (3)0.3720 (17)0.063 (8)*
H25B0.512 (3)0.020 (3)0.4207 (19)0.069 (8)*
H25C0.401 (3)0.024 (3)0.4684 (19)0.073 (9)*
H45B0.463 (3)0.312 (3)0.9515 (18)0.068 (8)*
H11B0.692 (3)0.713 (3)0.8057 (18)0.072 (8)*
H45C0.331 (3)0.264 (3)0.914 (2)0.078 (9)*
H36B0.222 (3)0.515 (4)0.448 (2)0.076 (9)*
H14B0.280 (5)0.877 (5)0.788 (3)0.125 (16)*
H36C0.284 (4)0.611 (4)0.377 (2)0.088 (11)*
H24C0.955 (4)0.003 (4)0.723 (2)0.093 (11)*
H15C0.261 (4)1.085 (4)0.808 (2)0.098 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0289 (4)0.0337 (5)0.0438 (5)0.0053 (4)0.0102 (4)0.0110 (4)
O30.0349 (5)0.0343 (6)0.0409 (5)0.0056 (4)0.0121 (4)0.0004 (4)
O40.0416 (5)0.0330 (6)0.0380 (5)0.0046 (4)0.0113 (4)0.0038 (4)
O10.0277 (4)0.0454 (7)0.0481 (6)0.0063 (4)0.0074 (4)0.0059 (5)
C70.0276 (5)0.0280 (6)0.0281 (5)0.0018 (4)0.0016 (4)0.0003 (4)
C270.0256 (5)0.0302 (6)0.0271 (5)0.0014 (4)0.0027 (4)0.0013 (4)
C280.0273 (5)0.0313 (7)0.0309 (5)0.0008 (5)0.0034 (4)0.0028 (5)
C260.0237 (5)0.0316 (7)0.0302 (5)0.0003 (4)0.0027 (4)0.0026 (5)
C60.0277 (5)0.0279 (6)0.0258 (5)0.0000 (4)0.0018 (4)0.0007 (4)
C50.0264 (5)0.0331 (7)0.0292 (5)0.0011 (5)0.0003 (4)0.0028 (5)
C290.0312 (6)0.0311 (7)0.0386 (6)0.0008 (5)0.0028 (5)0.0025 (5)
C410.0335 (6)0.0392 (8)0.0361 (6)0.0019 (5)0.0077 (5)0.0030 (6)
C370.0297 (5)0.0301 (7)0.0272 (5)0.0006 (5)0.0032 (4)0.0002 (4)
C90.0332 (6)0.0290 (7)0.0314 (6)0.0017 (5)0.0052 (5)0.0027 (5)
C160.0300 (6)0.0299 (7)0.0312 (5)0.0007 (5)0.0075 (4)0.0016 (5)
C80.0294 (5)0.0315 (7)0.0315 (5)0.0020 (5)0.0014 (4)0.0037 (5)
C100.0300 (6)0.0306 (7)0.0361 (6)0.0033 (5)0.0049 (5)0.0003 (5)
C380.0311 (6)0.0330 (7)0.0282 (5)0.0004 (5)0.0016 (4)0.0004 (5)
C310.0277 (5)0.0415 (8)0.0294 (5)0.0034 (5)0.0061 (4)0.0021 (5)
C420.0314 (6)0.0358 (7)0.0315 (6)0.0042 (5)0.0026 (5)0.0016 (5)
C300.0295 (6)0.0394 (8)0.0311 (6)0.0056 (5)0.0015 (4)0.0042 (5)
C170.0409 (7)0.0392 (8)0.0285 (6)0.0005 (6)0.0084 (5)0.0053 (5)
C180.0503 (8)0.0465 (10)0.0342 (6)0.0056 (7)0.0112 (6)0.0129 (6)
C440.0331 (6)0.0473 (9)0.0332 (6)0.0020 (6)0.0008 (5)0.0012 (6)
C210.0356 (6)0.0301 (7)0.0405 (7)0.0012 (5)0.0070 (5)0.0011 (5)
C220.0397 (7)0.0357 (8)0.0513 (8)0.0028 (6)0.0013 (6)0.0103 (7)
C110.0403 (7)0.0319 (8)0.0426 (7)0.0032 (6)0.0069 (6)0.0098 (6)
C390.0414 (7)0.0435 (9)0.0271 (5)0.0016 (6)0.0020 (5)0.0031 (5)
C320.0429 (7)0.0482 (10)0.0393 (7)0.0094 (7)0.0051 (6)0.0112 (7)
C120.0493 (8)0.0349 (8)0.0423 (8)0.0082 (6)0.0073 (6)0.0079 (6)
C330.0572 (9)0.0442 (10)0.0403 (8)0.0047 (7)0.0011 (7)0.0111 (7)
C400.0433 (7)0.0491 (10)0.0311 (6)0.0003 (6)0.0093 (5)0.0014 (6)
C130.0501 (8)0.0306 (8)0.0427 (7)0.0049 (6)0.0006 (6)0.0046 (6)
C230.0590 (10)0.0435 (10)0.0448 (8)0.0022 (8)0.0065 (7)0.0068 (7)
C200.0574 (10)0.0300 (8)0.0621 (10)0.0052 (7)0.0128 (8)0.0040 (7)
C430.0355 (7)0.0689 (13)0.0484 (8)0.0037 (8)0.0136 (6)0.0041 (9)
C340.0488 (8)0.0426 (9)0.0429 (8)0.0007 (7)0.0022 (6)0.0068 (7)
C140.0641 (12)0.0452 (12)0.0756 (14)0.0181 (9)0.0141 (10)0.0167 (10)
C250.0731 (13)0.0685 (15)0.0401 (8)0.0155 (11)0.0037 (9)0.0236 (9)
C450.0413 (8)0.0558 (12)0.0591 (10)0.0145 (8)0.0063 (7)0.0074 (9)
C460.0366 (8)0.0613 (14)0.0833 (15)0.0080 (8)0.0070 (9)0.0000 (11)
C190.0686 (12)0.0369 (10)0.0577 (10)0.0088 (8)0.0122 (9)0.0156 (8)
C150.0680 (12)0.0384 (10)0.0581 (10)0.0133 (9)0.0143 (9)0.0006 (8)
C350.0599 (11)0.0511 (12)0.0593 (11)0.0042 (9)0.0112 (9)0.0052 (9)
C240.0396 (9)0.0783 (17)0.0794 (15)0.0108 (10)0.0016 (9)0.0226 (14)
C360.0584 (12)0.0607 (14)0.0692 (13)0.0005 (10)0.0070 (10)0.0006 (11)
Geometric parameters (Å, º) top
O2—C71.3836 (16)C11—H11B0.98 (3)
O2—H20.86 (3)C39—C401.523 (2)
O3—C261.3595 (18)C39—H39A0.98 (2)
O3—H30.84 (3)C39—H39B1.02 (3)
O4—C281.3723 (16)C32—C331.531 (3)
O4—H40.85 (3)C32—H32A1.02 (3)
O1—C51.3756 (17)C32—H32B0.98 (3)
O1—H10.83 (3)C12—C131.508 (2)
C7—C61.4031 (18)C12—H12A1.03 (3)
C7—C81.3829 (19)C12—H12B0.95 (3)
C27—C281.400 (2)C33—C341.516 (3)
C27—C261.4011 (17)C33—H33A1.00 (3)
C27—C371.5198 (18)C33—H33B0.99 (3)
C28—C291.392 (2)C40—H40A1.01 (3)
C26—C311.3973 (19)C40—H40B1.01 (3)
C6—C51.3978 (18)C13—C141.510 (3)
C6—C161.510 (2)C13—H13A0.94 (3)
C5—C101.388 (2)C13—H13B0.99 (3)
C29—C301.395 (2)C23—H23A0.95 (3)
C29—H290.98 (3)C23—H23B0.92 (3)
C41—C421.3361 (19)C20—C191.529 (3)
C41—C401.508 (2)C20—H20A1.00 (3)
C41—C431.505 (2)C20—H20B1.00 (3)
C37—C381.5530 (17)C43—H43A0.96 (4)
C37—C421.5176 (18)C43—H43B0.98 (3)
C37—H371.01 (2)C43—H43C0.97 (4)
C9—C81.397 (2)C34—C351.529 (3)
C9—C101.392 (2)C34—H34A1.02 (3)
C9—C111.507 (2)C34—H34B1.04 (3)
C16—C171.516 (2)C14—C151.507 (3)
C16—C211.550 (2)C14—H14A1.06 (4)
C16—H160.991 (19)C14—H14B0.97 (5)
C8—H80.98 (2)C25—H25A1.05 (4)
C10—H100.98 (2)C25—H25B0.94 (3)
C38—C441.5131 (19)C25—H25C0.91 (4)
C38—C391.5380 (19)C45—H45A1.01 (4)
C38—H381.01 (2)C45—H45B1.00 (3)
C31—C301.388 (2)C45—H45C0.91 (4)
C31—H310.97 (2)C46—H46A1.01 (3)
C42—H420.96 (2)C46—H46B0.97 (4)
C30—C321.516 (2)C19—H19A0.95 (3)
C17—C181.334 (2)C19—H19B0.99 (3)
C17—H171.01 (3)C15—H15A1.00 (3)
C18—C251.506 (3)C15—H15B1.03 (4)
C18—C191.500 (3)C15—H15C0.97 (4)
C44—C451.494 (3)C35—C361.517 (4)
C44—C461.323 (3)C35—H35A0.97 (3)
C21—C221.513 (2)C35—H35B0.94 (3)
C21—C201.532 (2)C24—H24A0.96 (3)
C21—H210.99 (2)C24—H24B0.91 (4)
C22—C231.323 (3)C24—H24C1.09 (4)
C22—C241.507 (3)C36—H36A1.00 (3)
C11—C121.517 (2)C36—H36B0.96 (4)
C11—H11A1.01 (3)C36—H36C1.07 (4)
C7—O2—H2107.9 (16)C33—C32—H32B109.2 (18)
C26—O3—H3112.3 (18)H32A—C32—H32B106 (2)
C28—O4—H4108.9 (19)C11—C12—H12A111.8 (19)
C5—O1—H1108.4 (18)C11—C12—H12B112.7 (19)
O2—C7—C6120.59 (12)C13—C12—C11113.86 (13)
C8—C7—O2116.69 (12)C13—C12—H12A109.4 (18)
C8—C7—C6122.72 (12)C13—C12—H12B108 (2)
C28—C27—C26116.69 (12)H12A—C12—H12B100 (3)
C28—C27—C37122.01 (11)C32—C33—H33A110.4 (16)
C26—C27—C37121.29 (13)C32—C33—H33B105.3 (17)
O4—C28—C27121.79 (13)C34—C33—C32113.65 (17)
O4—C28—C29115.90 (13)C34—C33—H33A108.3 (18)
C29—C28—C27122.32 (12)C34—C33—H33B111.2 (17)
O3—C26—C27116.85 (12)H33A—C33—H33B108 (2)
O3—C26—C31121.68 (12)C41—C40—C39111.66 (12)
C31—C26—C27121.46 (13)C41—C40—H40A110.2 (13)
C7—C6—C16122.20 (12)C41—C40—H40B109.2 (14)
C5—C6—C7116.12 (12)C39—C40—H40A111.0 (13)
C5—C6—C16121.68 (11)C39—C40—H40B110.6 (14)
O1—C5—C6116.65 (13)H40A—C40—H40B103.9 (19)
O1—C5—C10121.43 (13)C12—C13—C14113.65 (15)
C10—C5—C6121.92 (12)C12—C13—H13A109.9 (19)
C28—C29—C30119.97 (14)C12—C13—H13B111.2 (18)
C28—C29—H29120.1 (13)C14—C13—H13A108 (2)
C30—C29—H29119.9 (13)C14—C13—H13B108.2 (17)
C42—C41—C40121.44 (13)H13A—C13—H13B105 (2)
C42—C41—C43121.36 (14)C22—C23—H23A121.3 (17)
C43—C41—C40117.19 (13)C22—C23—H23B124.9 (18)
C27—C37—C38112.15 (11)H23A—C23—H23B114 (2)
C27—C37—H37106.6 (11)C21—C20—H20A106.8 (18)
C38—C37—H37107.8 (11)C21—C20—H20B109.9 (16)
C42—C37—C27110.20 (11)C19—C20—C21110.68 (15)
C42—C37—C38111.34 (10)C19—C20—H20A111.8 (16)
C42—C37—H37108.5 (11)C19—C20—H20B109.1 (16)
C8—C9—C11120.68 (13)H20A—C20—H20B108 (2)
C10—C9—C8118.71 (13)C41—C43—H43A116 (2)
C10—C9—C11120.60 (14)C41—C43—H43B112.6 (16)
C6—C16—C17111.32 (12)C41—C43—H43C107.7 (19)
C6—C16—C21112.57 (11)H43A—C43—H43B106 (3)
C6—C16—H16107.6 (12)H43A—C43—H43C104 (3)
C17—C16—C21110.52 (12)H43B—C43—H43C111 (3)
C17—C16—H16105.6 (11)C33—C34—C35113.08 (17)
C21—C16—H16108.9 (12)C33—C34—H34A109.5 (14)
C7—C8—C9119.71 (12)C33—C34—H34B108.6 (15)
C7—C8—H8119.2 (14)C35—C34—H34A109.1 (14)
C9—C8—H8121.1 (14)C35—C34—H34B109.3 (14)
C5—C10—C9120.58 (13)H34A—C34—H34B107 (2)
C5—C10—H10118.7 (13)C13—C14—H14A108 (2)
C9—C10—H10120.7 (13)C13—C14—H14B114 (3)
C37—C38—H38107.4 (11)C15—C14—C13114.30 (18)
C44—C38—C37112.51 (11)C15—C14—H14A110 (3)
C44—C38—C39112.76 (12)C15—C14—H14B103 (3)
C44—C38—H38108.0 (11)H14A—C14—H14B107 (4)
C39—C38—C37108.52 (11)C18—C25—H25A110.3 (18)
C39—C38—H38107.4 (11)C18—C25—H25B108.3 (19)
C26—C31—H31119.9 (15)C18—C25—H25C110 (2)
C30—C31—C26120.74 (12)H25A—C25—H25B115 (3)
C30—C31—H31119.4 (15)H25A—C25—H25C108 (3)
C41—C42—C37125.11 (12)H25B—C25—H25C105 (3)
C41—C42—H42118.5 (13)C44—C45—H45A116 (2)
C37—C42—H42116.4 (12)C44—C45—H45B111 (2)
C29—C30—C32120.33 (15)C44—C45—H45C112 (2)
C31—C30—C29118.81 (13)H45A—C45—H45B106 (3)
C31—C30—C32120.86 (14)H45A—C45—H45C103 (3)
C16—C17—H17113.6 (14)H45B—C45—H45C109 (3)
C18—C17—C16124.76 (16)C44—C46—H46A119 (2)
C18—C17—H17121.6 (14)C44—C46—H46B117 (2)
C17—C18—C25121.23 (19)H46A—C46—H46B124 (3)
C17—C18—C19121.57 (16)C18—C19—C20113.24 (16)
C19—C18—C25117.16 (18)C18—C19—H19A109.6 (18)
C45—C44—C38118.15 (15)C18—C19—H19B109 (2)
C46—C44—C38120.39 (17)C20—C19—H19A110.7 (16)
C46—C44—C45121.46 (17)C20—C19—H19B110.3 (19)
C16—C21—H21107.7 (13)H19A—C19—H19B103 (3)
C22—C21—C16111.96 (13)C14—C15—H15A113 (2)
C22—C21—C20114.41 (15)C14—C15—H15B108 (2)
C22—C21—H21107.7 (12)C14—C15—H15C117 (3)
C20—C21—C16108.26 (13)H15A—C15—H15B105 (3)
C20—C21—H21106.5 (13)H15A—C15—H15C105 (3)
C23—C22—C21120.27 (16)H15B—C15—H15C107 (3)
C23—C22—C24121.83 (19)C34—C35—H35A110.3 (17)
C24—C22—C21117.87 (18)C34—C35—H35B107.5 (19)
C9—C11—C12113.57 (12)C36—C35—C34112.3 (2)
C9—C11—H11A109.0 (16)C36—C35—H35A110.5 (18)
C9—C11—H11B110.9 (19)C36—C35—H35B112 (2)
C12—C11—H11A109.1 (14)H35A—C35—H35B104 (3)
C12—C11—H11B110 (2)C22—C24—H24A110.2 (18)
H11A—C11—H11B104 (2)C22—C24—H24B111 (2)
C38—C39—H39A110.1 (14)C22—C24—H24C106 (2)
C38—C39—H39B109.3 (14)H24A—C24—H24B113 (3)
C40—C39—C38110.32 (12)H24A—C24—H24C106 (3)
C40—C39—H39A111.6 (13)H24B—C24—H24C110 (3)
C40—C39—H39B109.4 (14)C35—C36—H36A111.6 (18)
H39A—C39—H39B105.9 (19)C35—C36—H36B108 (2)
C30—C32—C33114.85 (14)C35—C36—H36C108 (2)
C30—C32—H32A112.2 (16)H36A—C36—H36B110 (3)
C30—C32—H32B107.4 (17)H36A—C36—H36C109 (3)
C33—C32—H32A106.6 (15)H36B—C36—H36C110 (3)
O2—C7—C6—C5174.74 (12)C9—C11—C12—C13178.47 (15)
O2—C7—C6—C165.95 (19)C16—C6—C5—O12.37 (18)
O2—C7—C8—C9175.02 (12)C16—C6—C5—C10178.04 (12)
O3—C26—C31—C30179.81 (12)C16—C17—C18—C25178.89 (16)
O4—C28—C29—C30179.15 (13)C16—C17—C18—C191.5 (3)
O1—C5—C10—C9177.67 (13)C16—C21—C22—C23109.34 (19)
C7—C6—C5—O1178.32 (12)C16—C21—C22—C2469.1 (2)
C7—C6—C5—C101.27 (18)C16—C21—C20—C1963.94 (19)
C7—C6—C16—C1759.51 (16)C8—C7—C6—C55.08 (19)
C7—C6—C16—C2165.22 (16)C8—C7—C6—C16174.22 (12)
C27—C28—C29—C300.7 (2)C8—C9—C10—C53.1 (2)
C27—C26—C31—C301.3 (2)C8—C9—C11—C1255.2 (2)
C27—C37—C38—C4467.06 (16)C10—C9—C8—C70.6 (2)
C27—C37—C38—C39167.46 (12)C10—C9—C11—C12123.46 (16)
C27—C37—C42—C41135.63 (17)C38—C37—C42—C4110.5 (2)
C28—C27—C26—O3178.98 (11)C38—C39—C40—C4150.55 (19)
C28—C27—C26—C310.02 (18)C31—C30—C32—C33118.00 (18)
C28—C27—C37—C3870.38 (15)C42—C41—C40—C3916.2 (2)
C28—C27—C37—C4254.26 (16)C42—C37—C38—C44168.94 (13)
C28—C29—C30—C310.6 (2)C42—C37—C38—C3943.46 (16)
C28—C29—C30—C32179.24 (13)C30—C32—C33—C3466.3 (2)
C26—C27—C28—O4178.87 (12)C17—C16—C21—C22176.17 (13)
C26—C27—C28—C290.96 (18)C17—C16—C21—C2049.14 (16)
C26—C27—C37—C38109.37 (14)C17—C18—C19—C2011.9 (3)
C26—C27—C37—C42125.99 (13)C44—C38—C39—C40169.73 (14)
C26—C31—C30—C291.5 (2)C21—C16—C17—C1818.05 (19)
C26—C31—C30—C32178.27 (13)C21—C20—C19—C1844.8 (2)
C6—C7—C8—C94.8 (2)C22—C21—C20—C19170.46 (16)
C6—C5—C10—C92.8 (2)C11—C9—C8—C7178.12 (13)
C6—C16—C17—C18143.92 (15)C11—C9—C10—C5178.21 (13)
C6—C16—C21—C2258.66 (16)C11—C12—C13—C14178.8 (2)
C6—C16—C21—C20174.31 (13)C39—C38—C44—C4557.14 (19)
C5—C6—C16—C17121.22 (13)C39—C38—C44—C46121.6 (2)
C5—C6—C16—C21114.05 (13)C32—C33—C34—C35178.50 (17)
C29—C30—C32—C3362.2 (2)C12—C13—C14—C15178.5 (2)
C37—C27—C28—O41.37 (19)C33—C34—C35—C36177.4 (2)
C37—C27—C28—C29178.80 (12)C40—C41—C42—C374.0 (3)
C37—C27—C26—O31.26 (18)C20—C21—C22—C23127.02 (19)
C37—C27—C26—C31179.78 (11)C20—C21—C22—C2454.5 (2)
C37—C38—C44—C4566.00 (18)C43—C41—C42—C37176.55 (17)
C37—C38—C44—C46115.25 (19)C43—C41—C40—C39163.23 (17)
C37—C38—C39—C4064.94 (16)C25—C18—C19—C20165.63 (17)
 

Acknowledgements

We thank Ma­thias Meyer and Paul Swepston together with the Rigaku Oxford Diffraction team for supporting the project with Cu Kβ mirror optics as well as for experimental and technical advice.

Funding information

Funding for this research was provided by: Rigaku Oxford Diffraction

References

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