Acta Cryst. (2008). E64, o1686 [ doi:10.1107/S1600536808022010 ]
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.
Δ9 – Tetrahydrocannabinol tosylate (p-tosyl-Δ9—THC), was synthesized according to Duchek (2004).
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.
Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); 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 (Sheldrick, 2008).
![[Figure 1]](./nc2105fig1thm.gif)
| Fig. 1. Crystal structure of the title compound with labelling and displacement ellipsoids drawn at the 50% probability level. |
| 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 |
| 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 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) |
| C28H36O4S | V = 2515.27 (7) Å3 |
| Mr = 468.63 | Z = 4 |
| Orthorhombic, P212121 | Cu Kα |
| a = 9.8759 (2) Å | µ = 1.39 mm−1 |
| b = 13.2996 (2) Å | T = 100 K |
| c = 19.1500 (3) Å | 0.19 × 0.17 × 0.16 mm |
| Bruker SMART CCD area-detector diffractometer | 4562 independent reflections |
| Absorption correction: none | 4438 reflections with I > 2σ(I) |
| 47731 measured reflections | Rint = 0.034 |
| R[F2 > 2σ(F2)] = 0.027 | H-atom parameters constrained |
| wR(F2) = 0.069 | Δρmax = 0.25 e Å−3 |
| S = 1.04 | Δρmin = −0.24 e Å−3 |
| 4562 reflections | Absolute structure: Flack (1983), 1965 Friedel pairs |
| 303 parameters | Flack parameter: 0.023 (11) |
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. |
| 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) |
| 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) |
| 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) |
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.
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