Abstract
In the crystal structure of the title compound, C28H36O4S, the p-tolyl ring is inclined at 35.8° to the aromatic ring. The cyclohexene ring adopts a boat conformation and the heterocyclic ring is in a slightly distorted screw boat conformation.
Related literature
For the physiological actions of tetrahydrocannabinol (Δ9—THC), the most psychologically active constituent of Cannabis sativa, see: Mechoulam & Gaoni (1967 ▶). For the synthesis of Δ9—THC-tosylate, see: Duchek (2004 ▶).
Experimental
Crystal data
C28H36O4S
M r = 468.63
Orthorhombic,
a = 9.8759 (2) Å
b = 13.2996 (2) Å
c = 19.1500 (3) Å
V = 2515.27 (7) Å3
Z = 4
Cu Kα radiation
μ = 1.39 mm−1
T = 100 K
0.19 × 0.17 × 0.16 mm
Data collection
Bruker SMART CCD area-detector diffractometer
Absorption correction: none
47731 measured reflections
4562 independent reflections
4438 reflections with I > 2σ(I)
R int = 0.034
Refinement
R[F 2 > 2σ(F 2)] = 0.026
wR(F 2) = 0.069
S = 1.04
4562 reflections
303 parameters
H-atom parameters constrained
Δρmax = 0.25 e Å−3
Δρmin = −0.24 e Å−3
Absolute structure: Flack (1983 ▶), 1965 Friedel pairs
Flack parameter: 0.023 (11)
Data collection: SMART (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.
Supplementary Material
Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808022010/nc2105sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022010/nc2105Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors thank Desmond Slade, John R. Duchek and David J. Kimmich for their valuable contributions, and the Center for Disease Control and Prevention, USA, for providing financial assistance (CDC cooperative agreements 1UO1 CI000211-03 and 1UO1 CI000362-01). This investigation was conducted in a facility constructed with support from Research Facilities Improvement Program grant No. C06 Rr-14503-01 from the National Center for Research Resources, National Institutes of Health. The project was also supported in part by the National Institute on Drug Abuse, contract No. N01DA-5-7746.
supplementary crystallographic information
Experimental
Δ9 – Tetrahydrocannabinol tosylate (p-tosyl-Δ9—THC), was synthesized according to Duchek (2004).
Refinement
All H atoms were located in difference maps and treated as riding atoms, with the following distance restraints: C—H = 0.93 Å, Uiso=1.2Ueq (C) for Csp2, C—H = 0.98 Å, Uiso = 1.2Ueq (C) for CH, C—H = 0.97 Å, Uiso = 1.2Ueq (C) for CH2, C—H = 0.96 Å, Uiso = 1.5Ueq (C) for CH3.
Figures
Fig. 1.
Crystal structure of the title compound with labelling and displacement ellipsoids drawn at the 50% probability level.
Crystal data
| C28H36O4S | F000 = 1008 |
| Mr = 468.63 | Dx = 1.238 Mg m−3 |
| Orthorhombic, P212121 | Cu Kα radiation λ = 1.54178 Å |
| Hall symbol: P 2ac 2ab | Cell parameters from 9942 reflections |
| a = 9.8759 (2) Å | θ = 4.1–67.4º |
| b = 13.2996 (2) Å | µ = 1.39 mm−1 |
| c = 19.1500 (3) Å | T = 100 K |
| V = 2515.27 (7) Å3 | Blocks, colourless |
| Z = 4 | 0.19 × 0.17 × 0.16 mm |
Data collection
| Bruker SMART CCD area-detector diffractometer | 4438 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.034 |
| T = 100 K | θmax = 68.0º |
| φ and ω scans | θmin = 4.1º |
| Absorption correction: none | h = −11→11 |
| 47731 measured reflections | k = −15→15 |
| 4562 independent reflections | l = −23→23 |
Refinement
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.027 | w = 1/[σ2(Fo2) + (0.0429P)2 + 0.4744P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.069 | (Δ/σ)max = 0.002 |
| S = 1.04 | Δρmax = 0.25 e Å−3 |
| 4562 reflections | Δρmin = −0.24 e Å−3 |
| 303 parameters | Extinction correction: none |
| Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 1965 Friedel pairs |
| Secondary atom site location: difference Fourier map | Flack parameter: 0.023 (11) |
Special details
| 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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon 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)
| x | y | z | Uiso*/Ueq | ||
| S1 | 0.46490 (3) | 0.05656 (2) | 1.076895 (17) | 0.01846 (9) | |
| C1 | 0.47927 (14) | 0.18406 (10) | 0.97409 (7) | 0.0172 (3) | |
| C2 | 0.47639 (14) | 0.28371 (11) | 0.99381 (7) | 0.0187 (3) | |
| H2 | 0.5205 | 0.3046 | 1.0342 | 0.022* | |
| C3 | 0.40657 (14) | 0.35294 (11) | 0.95249 (7) | 0.0186 (3) | |
| C4 | 0.34101 (15) | 0.31759 (11) | 0.89315 (7) | 0.0189 (3) | |
| H4 | 0.2911 | 0.3621 | 0.8659 | 0.023* | |
| C7 | 0.39042 (17) | −0.07962 (11) | 0.78957 (8) | 0.0262 (3) | |
| H7A | 0.3350 | −0.1182 | 0.8216 | 0.031* | |
| H7B | 0.3527 | −0.0869 | 0.7431 | 0.031* | |
| C9 | 0.61971 (16) | −0.07895 (11) | 0.84941 (8) | 0.0244 (3) | |
| C10 | 0.57509 (15) | −0.00757 (11) | 0.89264 (7) | 0.0207 (3) | |
| H10 | 0.6326 | 0.0152 | 0.9277 | 0.025* | |
| C8 | 0.53477 (18) | −0.11963 (12) | 0.79053 (8) | 0.0291 (3) | |
| H8A | 0.5319 | −0.1923 | 0.7941 | 0.035* | |
| H8B | 0.5780 | −0.1029 | 0.7466 | 0.035* | |
| C6 | 0.25642 (15) | 0.08708 (11) | 0.79805 (8) | 0.0213 (3) | |
| C4A | 0.34857 (14) | 0.21680 (11) | 0.87368 (7) | 0.0184 (3) | |
| C10A | 0.43477 (14) | 0.03799 (10) | 0.88715 (7) | 0.0189 (3) | |
| H10A | 0.3732 | −0.0034 | 0.9152 | 0.023* | |
| C10B | 0.42230 (14) | 0.14608 (10) | 0.91271 (7) | 0.0178 (3) | |
| C19 | 0.40283 (15) | 0.14829 (10) | 1.13478 (7) | 0.0176 (3) | |
| C20 | 0.47260 (15) | 0.16732 (11) | 1.19667 (7) | 0.0208 (3) | |
| H20 | 0.5532 | 0.1340 | 1.2065 | 0.025* | |
| C24 | 0.28354 (15) | 0.19860 (11) | 1.11914 (7) | 0.0199 (3) | |
| H24 | 0.2371 | 0.1851 | 1.0779 | 0.024* | |
| C21 | 0.42018 (16) | 0.23624 (12) | 1.24306 (8) | 0.0228 (3) | |
| H21 | 0.4649 | 0.2478 | 1.2850 | 0.027* | |
| C14 | 0.40301 (15) | 0.46315 (10) | 0.97123 (7) | 0.0216 (3) | |
| H14A | 0.4323 | 0.4713 | 1.0193 | 0.026* | |
| H14B | 0.3105 | 0.4872 | 0.9679 | 0.026* | |
| C11 | 0.13920 (16) | 0.05062 (12) | 0.84292 (8) | 0.0264 (3) | |
| H11A | 0.1622 | 0.0579 | 0.8914 | 0.040* | |
| H11B | 0.1214 | −0.0189 | 0.8329 | 0.040* | |
| H11C | 0.0600 | 0.0898 | 0.8328 | 0.040* | |
| C23 | 0.23487 (16) | 0.26903 (11) | 1.16577 (8) | 0.0221 (3) | |
| H23 | 0.1559 | 0.3040 | 1.1551 | 0.027* | |
| C22 | 0.30153 (15) | 0.28894 (11) | 1.22843 (8) | 0.0210 (3) | |
| C18 | 0.5664 (2) | 0.77077 (13) | 1.03217 (10) | 0.0409 (5) | |
| H18A | 0.5992 | 0.8127 | 0.9951 | 0.061* | |
| H18B | 0.6205 | 0.7812 | 1.0732 | 0.061* | |
| H18C | 0.4738 | 0.7876 | 1.0422 | 0.061* | |
| C25 | 0.24424 (18) | 0.36377 (13) | 1.27916 (9) | 0.0301 (4) | |
| H25A | 0.1675 | 0.3349 | 1.3025 | 0.045* | |
| H25B | 0.2166 | 0.4231 | 1.2544 | 0.045* | |
| H25C | 0.3121 | 0.3812 | 1.3130 | 0.045* | |
| C15 | 0.49335 (15) | 0.52705 (10) | 0.92386 (8) | 0.0227 (3) | |
| H15A | 0.4620 | 0.5208 | 0.8761 | 0.027* | |
| H15B | 0.5852 | 0.5013 | 0.9258 | 0.027* | |
| C17 | 0.57512 (18) | 0.66107 (12) | 1.01015 (9) | 0.0293 (4) | |
| H17A | 0.5419 | 0.6191 | 1.0479 | 0.035* | |
| H17B | 0.6693 | 0.6438 | 1.0022 | 0.035* | |
| C16 | 0.49424 (17) | 0.63855 (11) | 0.94437 (8) | 0.0260 (3) | |
| H16A | 0.5317 | 0.6773 | 0.9060 | 0.031* | |
| H16B | 0.4016 | 0.6606 | 0.9513 | 0.031* | |
| C12 | 0.21926 (17) | 0.08792 (12) | 0.72084 (8) | 0.0273 (3) | |
| H12A | 0.1454 | 0.1336 | 0.7133 | 0.041* | |
| H12B | 0.1928 | 0.0215 | 0.7067 | 0.041* | |
| H12C | 0.2961 | 0.1091 | 0.6939 | 0.041* | |
| O2 | 0.55008 (10) | 0.11806 (7) | 1.01992 (5) | 0.0185 (2) | |
| O3 | 0.56579 (11) | −0.00225 (8) | 1.11089 (5) | 0.0271 (2) | |
| O4 | 0.35208 (11) | 0.00985 (8) | 1.04341 (5) | 0.0240 (2) | |
| C13 | 0.75923 (18) | −0.12306 (14) | 0.85622 (9) | 0.0344 (4) | |
| H13A | 0.8061 | −0.0908 | 0.8940 | 0.052* | |
| H13B | 0.8084 | −0.1127 | 0.8136 | 0.052* | |
| H13C | 0.7523 | −0.1938 | 0.8654 | 0.052* | |
| C6A | 0.38882 (15) | 0.03099 (10) | 0.81073 (7) | 0.0201 (3) | |
| H6A | 0.4582 | 0.0647 | 0.7827 | 0.024* | |
| O1 | 0.28074 (11) | 0.19339 (8) | 0.81346 (5) | 0.0207 (2) |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.02166 (17) | 0.01704 (15) | 0.01669 (15) | 0.00077 (14) | 0.00114 (13) | 0.00015 (13) |
| C1 | 0.0154 (7) | 0.0200 (7) | 0.0162 (6) | −0.0006 (6) | 0.0033 (5) | 0.0013 (5) |
| C2 | 0.0174 (7) | 0.0236 (7) | 0.0149 (6) | −0.0041 (6) | 0.0019 (5) | −0.0024 (5) |
| C3 | 0.0178 (7) | 0.0188 (7) | 0.0191 (7) | −0.0019 (6) | 0.0064 (5) | −0.0007 (5) |
| C4 | 0.0189 (7) | 0.0188 (7) | 0.0190 (7) | −0.0008 (6) | 0.0023 (5) | 0.0015 (6) |
| C7 | 0.0351 (9) | 0.0208 (8) | 0.0227 (7) | −0.0001 (7) | −0.0047 (6) | −0.0053 (6) |
| C9 | 0.0272 (8) | 0.0229 (8) | 0.0231 (7) | 0.0022 (6) | 0.0012 (6) | −0.0001 (6) |
| C10 | 0.0240 (7) | 0.0203 (7) | 0.0177 (6) | 0.0003 (6) | −0.0006 (5) | −0.0013 (6) |
| C8 | 0.0382 (9) | 0.0228 (7) | 0.0263 (8) | 0.0047 (7) | 0.0008 (7) | −0.0079 (6) |
| C6 | 0.0252 (8) | 0.0166 (7) | 0.0221 (7) | −0.0025 (6) | −0.0026 (6) | −0.0028 (5) |
| C4A | 0.0174 (7) | 0.0215 (7) | 0.0162 (7) | −0.0024 (6) | 0.0029 (5) | −0.0014 (5) |
| C10A | 0.0221 (7) | 0.0184 (7) | 0.0161 (6) | −0.0019 (6) | 0.0006 (5) | −0.0014 (5) |
| C10B | 0.0172 (7) | 0.0182 (7) | 0.0179 (7) | −0.0019 (5) | 0.0027 (5) | −0.0010 (5) |
| C19 | 0.0195 (7) | 0.0185 (7) | 0.0148 (6) | −0.0010 (6) | 0.0024 (5) | 0.0011 (5) |
| C20 | 0.0174 (7) | 0.0258 (7) | 0.0193 (7) | 0.0010 (6) | −0.0017 (6) | 0.0014 (5) |
| C24 | 0.0197 (7) | 0.0230 (7) | 0.0169 (7) | −0.0010 (6) | −0.0026 (6) | 0.0006 (5) |
| C21 | 0.0223 (8) | 0.0286 (8) | 0.0175 (7) | −0.0048 (6) | −0.0032 (6) | −0.0024 (6) |
| C14 | 0.0220 (7) | 0.0203 (7) | 0.0225 (7) | −0.0008 (6) | 0.0022 (6) | −0.0038 (5) |
| C11 | 0.0233 (8) | 0.0255 (7) | 0.0303 (8) | −0.0017 (7) | −0.0014 (6) | −0.0008 (6) |
| C23 | 0.0197 (7) | 0.0242 (7) | 0.0225 (7) | 0.0039 (6) | −0.0001 (6) | 0.0031 (6) |
| C22 | 0.0224 (8) | 0.0187 (7) | 0.0220 (7) | −0.0032 (6) | 0.0024 (6) | 0.0006 (6) |
| C18 | 0.0586 (13) | 0.0257 (8) | 0.0384 (10) | −0.0098 (8) | 0.0003 (9) | −0.0062 (7) |
| C25 | 0.0326 (9) | 0.0304 (8) | 0.0273 (8) | 0.0026 (7) | −0.0007 (7) | −0.0070 (7) |
| C15 | 0.0264 (7) | 0.0193 (7) | 0.0224 (7) | −0.0013 (6) | 0.0000 (6) | −0.0009 (6) |
| C17 | 0.0332 (9) | 0.0217 (8) | 0.0329 (9) | −0.0040 (7) | −0.0023 (7) | −0.0014 (6) |
| C16 | 0.0321 (9) | 0.0176 (7) | 0.0284 (8) | −0.0006 (6) | −0.0016 (6) | 0.0021 (6) |
| C12 | 0.0336 (9) | 0.0248 (7) | 0.0235 (8) | 0.0005 (7) | −0.0070 (6) | −0.0050 (6) |
| O2 | 0.0180 (5) | 0.0210 (5) | 0.0164 (5) | 0.0007 (4) | 0.0003 (4) | −0.0004 (4) |
| O3 | 0.0329 (6) | 0.0244 (5) | 0.0242 (5) | 0.0065 (5) | 0.0008 (4) | 0.0025 (4) |
| O4 | 0.0277 (6) | 0.0222 (5) | 0.0220 (5) | −0.0061 (4) | 0.0039 (4) | −0.0029 (4) |
| C13 | 0.0325 (9) | 0.0362 (9) | 0.0346 (9) | 0.0108 (7) | 0.0016 (7) | −0.0088 (7) |
| C6A | 0.0232 (8) | 0.0195 (7) | 0.0175 (7) | −0.0032 (6) | 0.0007 (6) | −0.0031 (5) |
| O1 | 0.0271 (5) | 0.0172 (5) | 0.0179 (5) | −0.0009 (4) | −0.0047 (4) | −0.0017 (4) |
Geometric parameters (Å, °)
| S1—O3 | 1.4243 (11) | C20—H20 | 0.9300 |
| S1—O4 | 1.4277 (11) | C24—C23 | 1.380 (2) |
| S1—O2 | 1.6022 (10) | C24—H24 | 0.9300 |
| S1—C19 | 1.7586 (14) | C21—C22 | 1.394 (2) |
| C1—C2 | 1.3783 (19) | C21—H21 | 0.9300 |
| C1—C10B | 1.3976 (19) | C14—C15 | 1.5301 (19) |
| C1—O2 | 1.4247 (17) | C14—H14A | 0.9700 |
| C2—C3 | 1.396 (2) | C14—H14B | 0.9700 |
| C2—H2 | 0.9300 | C11—H11A | 0.9600 |
| C3—C4 | 1.390 (2) | C11—H11B | 0.9600 |
| C3—C14 | 1.5095 (19) | C11—H11C | 0.9600 |
| C4—C4A | 1.393 (2) | C23—C22 | 1.394 (2) |
| C4—H4 | 0.9300 | C23—H23 | 0.9300 |
| C7—C8 | 1.522 (2) | C22—C25 | 1.501 (2) |
| C7—C6A | 1.5260 (19) | C18—C17 | 1.521 (2) |
| C7—H7A | 0.9700 | C18—H18A | 0.9600 |
| C7—H7B | 0.9700 | C18—H18B | 0.9600 |
| C9—C10 | 1.335 (2) | C18—H18C | 0.9600 |
| C9—C13 | 1.503 (2) | C25—H25A | 0.9600 |
| C9—C8 | 1.506 (2) | C25—H25B | 0.9600 |
| C10—C10A | 1.516 (2) | C25—H25C | 0.9600 |
| C10—H10 | 0.9300 | C15—C16 | 1.5341 (19) |
| C8—H8A | 0.9700 | C15—H15A | 0.9700 |
| C8—H8B | 0.9700 | C15—H15B | 0.9700 |
| C6—O1 | 1.4643 (17) | C17—C16 | 1.521 (2) |
| C6—C11 | 1.521 (2) | C17—H17A | 0.9700 |
| C6—C12 | 1.523 (2) | C17—H17B | 0.9700 |
| C6—C6A | 1.525 (2) | C16—H16A | 0.9700 |
| C4A—O1 | 1.3694 (17) | C16—H16B | 0.9700 |
| C4A—C10B | 1.405 (2) | C12—H12A | 0.9600 |
| C10A—C10B | 1.5236 (18) | C12—H12B | 0.9600 |
| C10A—C6A | 1.5350 (18) | C12—H12C | 0.9600 |
| C10A—H10A | 0.9800 | C13—H13A | 0.9600 |
| C19—C24 | 1.388 (2) | C13—H13B | 0.9600 |
| C19—C20 | 1.394 (2) | C13—H13C | 0.9600 |
| C20—C21 | 1.377 (2) | C6A—H6A | 0.9800 |
| O3—S1—O4 | 120.81 (7) | C3—C14—H14A | 109.1 |
| O3—S1—O2 | 102.96 (6) | C15—C14—H14A | 109.1 |
| O4—S1—O2 | 109.03 (6) | C3—C14—H14B | 109.1 |
| O3—S1—C19 | 109.68 (7) | C15—C14—H14B | 109.1 |
| O4—S1—C19 | 108.24 (7) | H14A—C14—H14B | 107.8 |
| O2—S1—C19 | 104.96 (6) | C6—C11—H11A | 109.5 |
| C2—C1—C10B | 124.73 (13) | C6—C11—H11B | 109.5 |
| C2—C1—O2 | 115.71 (12) | H11A—C11—H11B | 109.5 |
| C10B—C1—O2 | 119.53 (12) | C6—C11—H11C | 109.5 |
| C1—C2—C3 | 119.27 (13) | H11A—C11—H11C | 109.5 |
| C1—C2—H2 | 120.4 | H11B—C11—H11C | 109.5 |
| C3—C2—H2 | 120.4 | C24—C23—C22 | 121.41 (14) |
| C4—C3—C2 | 118.06 (13) | C24—C23—H23 | 119.3 |
| C4—C3—C14 | 120.79 (13) | C22—C23—H23 | 119.3 |
| C2—C3—C14 | 121.14 (13) | C21—C22—C23 | 118.32 (14) |
| C3—C4—C4A | 121.28 (14) | C21—C22—C25 | 121.34 (14) |
| C3—C4—H4 | 119.4 | C23—C22—C25 | 120.32 (14) |
| C4A—C4—H4 | 119.4 | C17—C18—H18A | 109.5 |
| C8—C7—C6A | 110.09 (13) | C17—C18—H18B | 109.5 |
| C8—C7—H7A | 109.6 | H18A—C18—H18B | 109.5 |
| C6A—C7—H7A | 109.6 | C17—C18—H18C | 109.5 |
| C8—C7—H7B | 109.6 | H18A—C18—H18C | 109.5 |
| C6A—C7—H7B | 109.6 | H18B—C18—H18C | 109.5 |
| H7A—C7—H7B | 108.2 | C22—C25—H25A | 109.5 |
| C10—C9—C13 | 121.77 (15) | C22—C25—H25B | 109.5 |
| C10—C9—C8 | 122.42 (14) | H25A—C25—H25B | 109.5 |
| C13—C9—C8 | 115.81 (13) | C22—C25—H25C | 109.5 |
| C9—C10—C10A | 122.90 (14) | H25A—C25—H25C | 109.5 |
| C9—C10—H10 | 118.6 | H25B—C25—H25C | 109.5 |
| C10A—C10—H10 | 118.6 | C14—C15—C16 | 112.86 (12) |
| C9—C8—C7 | 113.91 (13) | C14—C15—H15A | 109.0 |
| C9—C8—H8A | 108.8 | C16—C15—H15A | 109.0 |
| C7—C8—H8A | 108.8 | C14—C15—H15B | 109.0 |
| C9—C8—H8B | 108.8 | C16—C15—H15B | 109.0 |
| C7—C8—H8B | 108.8 | H15A—C15—H15B | 107.8 |
| H8A—C8—H8B | 107.7 | C18—C17—C16 | 112.87 (14) |
| O1—C6—C11 | 108.59 (12) | C18—C17—H17A | 109.0 |
| O1—C6—C12 | 103.19 (12) | C16—C17—H17A | 109.0 |
| C11—C6—C12 | 111.55 (13) | C18—C17—H17B | 109.0 |
| O1—C6—C6A | 107.43 (11) | C16—C17—H17B | 109.0 |
| C11—C6—C6A | 114.00 (12) | H17A—C17—H17B | 107.8 |
| C12—C6—C6A | 111.40 (12) | C17—C16—C15 | 113.92 (13) |
| O1—C4A—C4 | 114.70 (13) | C17—C16—H16A | 108.8 |
| O1—C4A—C10B | 123.32 (13) | C15—C16—H16A | 108.8 |
| C4—C4A—C10B | 121.97 (13) | C17—C16—H16B | 108.8 |
| C10—C10A—C10B | 115.39 (12) | C15—C16—H16B | 108.8 |
| C10—C10A—C6A | 108.19 (11) | H16A—C16—H16B | 107.7 |
| C10B—C10A—C6A | 109.85 (11) | C6—C12—H12A | 109.5 |
| C10—C10A—H10A | 107.7 | C6—C12—H12B | 109.5 |
| C10B—C10A—H10A | 107.7 | H12A—C12—H12B | 109.5 |
| C6A—C10A—H10A | 107.7 | C6—C12—H12C | 109.5 |
| C1—C10B—C4A | 114.47 (13) | H12A—C12—H12C | 109.5 |
| C1—C10B—C10A | 125.35 (13) | H12B—C12—H12C | 109.5 |
| C4A—C10B—C10A | 120.18 (12) | C1—O2—S1 | 118.44 (8) |
| C24—C19—C20 | 121.03 (13) | C9—C13—H13A | 109.5 |
| C24—C19—S1 | 119.63 (11) | C9—C13—H13B | 109.5 |
| C20—C19—S1 | 119.31 (11) | H13A—C13—H13B | 109.5 |
| C21—C20—C19 | 118.91 (14) | C9—C13—H13C | 109.5 |
| C21—C20—H20 | 120.5 | H13A—C13—H13C | 109.5 |
| C19—C20—H20 | 120.5 | H13B—C13—H13C | 109.5 |
| C23—C24—C19 | 118.90 (13) | C6—C6A—C7 | 115.99 (12) |
| C23—C24—H24 | 120.5 | C6—C6A—C10A | 112.07 (12) |
| C19—C24—H24 | 120.5 | C7—C6A—C10A | 107.98 (12) |
| C20—C21—C22 | 121.40 (14) | C6—C6A—H6A | 106.8 |
| C20—C21—H21 | 119.3 | C7—C6A—H6A | 106.8 |
| C22—C21—H21 | 119.3 | C10A—C6A—H6A | 106.8 |
| C3—C14—C15 | 112.63 (12) | C4A—O1—C6 | 118.01 (11) |
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2105).
References
- Bruker (2003). SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
- Bruker (2005). SMART Bruker AXS Inc., Madison, Wisconsin, USA.
- Duchek, J. R. (2004). US Patent No. 2006/0094774-A1.
- Flack, H. D. (1983). Acta Cryst. A39, 876–881.
- Mechoulam, R. & Gaoni, Y. (1967). Fortschr. Chem. Org. Naturst.25, 175–213. [DOI] [PubMed]
- Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808022010/nc2105sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022010/nc2105Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report