organic compounds
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
The 21H30O2, {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 is given as R,R, referring to Mechoulam et al. [(1967.J. Am. Chem. Soc. 89, 4552–4554]. In the latter, the 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 including the was possible and is shown in this work. Furthermore, the rather uncommon Cu Kβ wavelength radiation was applied for the which confirmed the to be R,R.
of cannabidiol, CKeywords: crystal structure; cannabidiol; Cu Kβ radiation; absolute structure.
CCDC reference: 1533487
Structure description
The , 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.
of the title compound, Fig. 1Differing in the freely rotatable unsaturated alkyl chain of the cannabidiol molecule, two molecules with different orientations of this side chain are found within the ). These independent molecules are both found to have the R,R configuration, confirming earlier investigations by Jones et al. (1977), Ottersen & Rosenqvist (1977) and Mechoulam et al. (1967). In the latter, the was identified by chemical means.
(Fig. 1Synthesis 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 .
details are summarized in Table 1Structural data
CCDC reference: 1533487
https://doi.org/10.1107/S2414314617002760/su4129sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617002760/su4129Isup2.hkl
Data collection: CrysAlis PRO (Rigaku OD, 2015); cell
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).C21H30O2 | Dx = 1.101 Mg m−3 |
Mr = 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 |
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 | Rint = 0.044 |
Detector resolution: 4.1818 pixels mm-1 | θmax = 75.3°, θmin = 2.4° |
ω scans | h = −14→14 |
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2015) | k = −15→14 |
Tmin = 0.996, Tmax = 0.997 | l = −23→23 |
85198 measured reflections |
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(Fo2) + (0.0493P)2 + 0.1553P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.088 | (Δ/σ)max < 0.001 |
S = 1.03 | Δρmax = 0.23 e Å−3 |
10203 reflections | Δρmin = −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 |
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. |
x | y | z | Uiso*/Ueq | ||
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)* |
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) |
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) |
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
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