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

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ISSN: 2056-9890

(6aR,10aR)-6,6,9-Tri­methyl-3-pentyl-6a,7,8,10a-tetra­hydro-6H-benzo[c]­chromen-1-yl 4-methyl­benzene­sulfonate

aNational Center for Natural Products Research, The University of Mississippi, University, MS 38677, USA, bEl Sohly Laboratories Inc., 5 Industrial Park Drive, Oxford, MS 38655, USA, cThe University of Mississippi, Department of Medicinal Chemistry, 417 Faser Hall, University, MS 38677, USA, dCovidien, 3600 N. 2nd Street, St Louis, MO 63147, USA, eNational Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, University, MS 38677, USA, fDepartment of Chemistry and Biochemistry, The University of Mississippi, University, MS 38677, USA, and gNational Center for Natural Products Research, Department of Pharmaceutics, School of Pharmacy, The University of Mississippi, University, MS 38677, USA
*Correspondence e-mail: elsohly@elsohly.com

(Received 15 May 2008; accepted 14 July 2008; online 6 August 2008)

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[Mechoulam, R. & Gaoni, Y. (1967). Fortschr. Chem. Org. Naturst. 25, 175-213.]). For the synthesis of Δ9—THC-tosyl­ate, see: Duchek (2004[Duchek, J. R. (2004). US Patent No. 2006/0094774-A1.]).

[Scheme 1]

Experimental

Crystal data
  • C28H36O4S

  • Mr = 468.63

  • Orthorhombic, P 21 21 21

  • 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)

  • Rint = 0.034

Refinement
  • R[F2 > 2σ(F2)] = 0.026

  • wR(F2) = 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[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1965 Friedel pairs

  • Flack parameter: 0.023 (11)

Data collection: SMART (Bruker, 2005[Bruker (2005). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Related literature top

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 top

Δ9 – Tetrahydrocannabinol tosylate (p-tosyl-Δ9—THC), was synthesized according to Duchek (2004).

Refinement top

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.

Computing details top

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).

Figures top
[Figure 1] Fig. 1. Crystal structure of the title compound with labelling and displacement ellipsoids drawn at the 50% probability level.
(6aR,10aR)-6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H- benzo[c]chromen-1-yl 4-methylbenzenesulfonate top
Crystal data top
C28H36O4SF(000) = 1008
Mr = 468.63Dx = 1.238 Mg m3
Orthorhombic, P212121Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2abCell parameters from 9942 reflections
a = 9.8759 (2) Åθ = 4.1–67.4°
b = 13.2996 (2) ŵ = 1.39 mm1
c = 19.1500 (3) ÅT = 100 K
V = 2515.27 (7) Å3Blocks, colourless
Z = 40.19 × 0.17 × 0.16 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
4438 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube, Siemens KFF Cu 2 K90Rint = 0.034
Graphite monochromatorθmax = 68.0°, θmin = 4.1°
ϕ and ω scansh = 1111
47731 measured reflectionsk = 1515
4562 independent reflectionsl = 2323
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.027H-atom parameters constrained
wR(F2) = 0.069 w = 1/[σ2(Fo2) + (0.0429P)2 + 0.4744P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.002
4562 reflectionsΔρmax = 0.25 e Å3
303 parametersΔρmin = 0.24 e Å3
0 restraintsAbsolute structure: Flack (1983), 1965 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.023 (11)
Crystal data top
C28H36O4SV = 2515.27 (7) Å3
Mr = 468.63Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 9.8759 (2) ŵ = 1.39 mm1
b = 13.2996 (2) ÅT = 100 K
c = 19.1500 (3) Å0.19 × 0.17 × 0.16 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
4438 reflections with I > 2σ(I)
47731 measured reflectionsRint = 0.034
4562 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.027H-atom parameters constrained
wR(F2) = 0.069Δρmax = 0.25 e Å3
S = 1.04Δρmin = 0.24 e Å3
4562 reflectionsAbsolute structure: Flack (1983), 1965 Friedel pairs
303 parametersAbsolute structure parameter: 0.023 (11)
0 restraints
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.46490 (3)0.05656 (2)1.076895 (17)0.01846 (9)
C10.47927 (14)0.18406 (10)0.97409 (7)0.0172 (3)
C20.47639 (14)0.28371 (11)0.99381 (7)0.0187 (3)
H20.52050.30461.03420.022*
C30.40657 (14)0.35294 (11)0.95249 (7)0.0186 (3)
C40.34101 (15)0.31759 (11)0.89315 (7)0.0189 (3)
H40.29110.36210.86590.023*
C70.39042 (17)0.07962 (11)0.78957 (8)0.0262 (3)
H7A0.33500.11820.82160.031*
H7B0.35270.08690.74310.031*
C90.61971 (16)0.07895 (11)0.84941 (8)0.0244 (3)
C100.57509 (15)0.00757 (11)0.89264 (7)0.0207 (3)
H100.63260.01520.92770.025*
C80.53477 (18)0.11963 (12)0.79053 (8)0.0291 (3)
H8A0.53190.19230.79410.035*
H8B0.57800.10290.74660.035*
C60.25642 (15)0.08708 (11)0.79805 (8)0.0213 (3)
C4A0.34857 (14)0.21680 (11)0.87368 (7)0.0184 (3)
C10A0.43477 (14)0.03799 (10)0.88715 (7)0.0189 (3)
H10A0.37320.00340.91520.023*
C10B0.42230 (14)0.14608 (10)0.91271 (7)0.0178 (3)
C190.40283 (15)0.14829 (10)1.13478 (7)0.0176 (3)
C200.47260 (15)0.16732 (11)1.19667 (7)0.0208 (3)
H200.55320.13401.20650.025*
C240.28354 (15)0.19860 (11)1.11914 (7)0.0199 (3)
H240.23710.18511.07790.024*
C210.42018 (16)0.23624 (12)1.24306 (8)0.0228 (3)
H210.46490.24781.28500.027*
C140.40301 (15)0.46315 (10)0.97123 (7)0.0216 (3)
H14A0.43230.47131.01930.026*
H14B0.31050.48720.96790.026*
C110.13920 (16)0.05062 (12)0.84292 (8)0.0264 (3)
H11A0.16220.05790.89140.040*
H11B0.12140.01890.83290.040*
H11C0.06000.08980.83280.040*
C230.23487 (16)0.26903 (11)1.16577 (8)0.0221 (3)
H230.15590.30401.15510.027*
C220.30153 (15)0.28894 (11)1.22843 (8)0.0210 (3)
C180.5664 (2)0.77077 (13)1.03217 (10)0.0409 (5)
H18A0.59920.81270.99510.061*
H18B0.62050.78121.07320.061*
H18C0.47380.78761.04220.061*
C250.24424 (18)0.36377 (13)1.27916 (9)0.0301 (4)
H25A0.16750.33491.30250.045*
H25B0.21660.42311.25440.045*
H25C0.31210.38121.31300.045*
C150.49335 (15)0.52705 (10)0.92386 (8)0.0227 (3)
H15A0.46200.52080.87610.027*
H15B0.58520.50130.92580.027*
C170.57512 (18)0.66107 (12)1.01015 (9)0.0293 (4)
H17A0.54190.61911.04790.035*
H17B0.66930.64381.00220.035*
C160.49424 (17)0.63855 (11)0.94437 (8)0.0260 (3)
H16A0.53170.67730.90600.031*
H16B0.40160.66060.95130.031*
C120.21926 (17)0.08792 (12)0.72084 (8)0.0273 (3)
H12A0.14540.13360.71330.041*
H12B0.19280.02150.70670.041*
H12C0.29610.10910.69390.041*
O20.55008 (10)0.11806 (7)1.01992 (5)0.0185 (2)
O30.56579 (11)0.00225 (8)1.11089 (5)0.0271 (2)
O40.35208 (11)0.00985 (8)1.04341 (5)0.0240 (2)
C130.75923 (18)0.12306 (14)0.85622 (9)0.0344 (4)
H13A0.80610.09080.89400.052*
H13B0.80840.11270.81360.052*
H13C0.75230.19380.86540.052*
C6A0.38882 (15)0.03099 (10)0.81073 (7)0.0201 (3)
H6A0.45820.06470.78270.024*
O10.28074 (11)0.19339 (8)0.81346 (5)0.0207 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.02166 (17)0.01704 (15)0.01669 (15)0.00077 (14)0.00114 (13)0.00015 (13)
C10.0154 (7)0.0200 (7)0.0162 (6)0.0006 (6)0.0033 (5)0.0013 (5)
C20.0174 (7)0.0236 (7)0.0149 (6)0.0041 (6)0.0019 (5)0.0024 (5)
C30.0178 (7)0.0188 (7)0.0191 (7)0.0019 (6)0.0064 (5)0.0007 (5)
C40.0189 (7)0.0188 (7)0.0190 (7)0.0008 (6)0.0023 (5)0.0015 (6)
C70.0351 (9)0.0208 (8)0.0227 (7)0.0001 (7)0.0047 (6)0.0053 (6)
C90.0272 (8)0.0229 (8)0.0231 (7)0.0022 (6)0.0012 (6)0.0001 (6)
C100.0240 (7)0.0203 (7)0.0177 (6)0.0003 (6)0.0006 (5)0.0013 (6)
C80.0382 (9)0.0228 (7)0.0263 (8)0.0047 (7)0.0008 (7)0.0079 (6)
C60.0252 (8)0.0166 (7)0.0221 (7)0.0025 (6)0.0026 (6)0.0028 (5)
C4A0.0174 (7)0.0215 (7)0.0162 (7)0.0024 (6)0.0029 (5)0.0014 (5)
C10A0.0221 (7)0.0184 (7)0.0161 (6)0.0019 (6)0.0006 (5)0.0014 (5)
C10B0.0172 (7)0.0182 (7)0.0179 (7)0.0019 (5)0.0027 (5)0.0010 (5)
C190.0195 (7)0.0185 (7)0.0148 (6)0.0010 (6)0.0024 (5)0.0011 (5)
C200.0174 (7)0.0258 (7)0.0193 (7)0.0010 (6)0.0017 (6)0.0014 (5)
C240.0197 (7)0.0230 (7)0.0169 (7)0.0010 (6)0.0026 (6)0.0006 (5)
C210.0223 (8)0.0286 (8)0.0175 (7)0.0048 (6)0.0032 (6)0.0024 (6)
C140.0220 (7)0.0203 (7)0.0225 (7)0.0008 (6)0.0022 (6)0.0038 (5)
C110.0233 (8)0.0255 (7)0.0303 (8)0.0017 (7)0.0014 (6)0.0008 (6)
C230.0197 (7)0.0242 (7)0.0225 (7)0.0039 (6)0.0001 (6)0.0031 (6)
C220.0224 (8)0.0187 (7)0.0220 (7)0.0032 (6)0.0024 (6)0.0006 (6)
C180.0586 (13)0.0257 (8)0.0384 (10)0.0098 (8)0.0003 (9)0.0062 (7)
C250.0326 (9)0.0304 (8)0.0273 (8)0.0026 (7)0.0007 (7)0.0070 (7)
C150.0264 (7)0.0193 (7)0.0224 (7)0.0013 (6)0.0000 (6)0.0009 (6)
C170.0332 (9)0.0217 (8)0.0329 (9)0.0040 (7)0.0023 (7)0.0014 (6)
C160.0321 (9)0.0176 (7)0.0284 (8)0.0006 (6)0.0016 (6)0.0021 (6)
C120.0336 (9)0.0248 (7)0.0235 (8)0.0005 (7)0.0070 (6)0.0050 (6)
O20.0180 (5)0.0210 (5)0.0164 (5)0.0007 (4)0.0003 (4)0.0004 (4)
O30.0329 (6)0.0244 (5)0.0242 (5)0.0065 (5)0.0008 (4)0.0025 (4)
O40.0277 (6)0.0222 (5)0.0220 (5)0.0061 (4)0.0039 (4)0.0029 (4)
C130.0325 (9)0.0362 (9)0.0346 (9)0.0108 (7)0.0016 (7)0.0088 (7)
C6A0.0232 (8)0.0195 (7)0.0175 (7)0.0032 (6)0.0007 (6)0.0031 (5)
O10.0271 (5)0.0172 (5)0.0179 (5)0.0009 (4)0.0047 (4)0.0017 (4)
Geometric parameters (Å, º) top
S1—O31.4243 (11)C20—H200.9300
S1—O41.4277 (11)C24—C231.380 (2)
S1—O21.6022 (10)C24—H240.9300
S1—C191.7586 (14)C21—C221.394 (2)
C1—C21.3783 (19)C21—H210.9300
C1—C10B1.3976 (19)C14—C151.5301 (19)
C1—O21.4247 (17)C14—H14A0.9700
C2—C31.396 (2)C14—H14B0.9700
C2—H20.9300C11—H11A0.9600
C3—C41.390 (2)C11—H11B0.9600
C3—C141.5095 (19)C11—H11C0.9600
C4—C4A1.393 (2)C23—C221.394 (2)
C4—H40.9300C23—H230.9300
C7—C81.522 (2)C22—C251.501 (2)
C7—C6A1.5260 (19)C18—C171.521 (2)
C7—H7A0.9700C18—H18A0.9600
C7—H7B0.9700C18—H18B0.9600
C9—C101.335 (2)C18—H18C0.9600
C9—C131.503 (2)C25—H25A0.9600
C9—C81.506 (2)C25—H25B0.9600
C10—C10A1.516 (2)C25—H25C0.9600
C10—H100.9300C15—C161.5341 (19)
C8—H8A0.9700C15—H15A0.9700
C8—H8B0.9700C15—H15B0.9700
C6—O11.4643 (17)C17—C161.521 (2)
C6—C111.521 (2)C17—H17A0.9700
C6—C121.523 (2)C17—H17B0.9700
C6—C6A1.525 (2)C16—H16A0.9700
C4A—O11.3694 (17)C16—H16B0.9700
C4A—C10B1.405 (2)C12—H12A0.9600
C10A—C10B1.5236 (18)C12—H12B0.9600
C10A—C6A1.5350 (18)C12—H12C0.9600
C10A—H10A0.9800C13—H13A0.9600
C19—C241.388 (2)C13—H13B0.9600
C19—C201.394 (2)C13—H13C0.9600
C20—C211.377 (2)C6A—H6A0.9800
O3—S1—O4120.81 (7)C3—C14—H14A109.1
O3—S1—O2102.96 (6)C15—C14—H14A109.1
O4—S1—O2109.03 (6)C3—C14—H14B109.1
O3—S1—C19109.68 (7)C15—C14—H14B109.1
O4—S1—C19108.24 (7)H14A—C14—H14B107.8
O2—S1—C19104.96 (6)C6—C11—H11A109.5
C2—C1—C10B124.73 (13)C6—C11—H11B109.5
C2—C1—O2115.71 (12)H11A—C11—H11B109.5
C10B—C1—O2119.53 (12)C6—C11—H11C109.5
C1—C2—C3119.27 (13)H11A—C11—H11C109.5
C1—C2—H2120.4H11B—C11—H11C109.5
C3—C2—H2120.4C24—C23—C22121.41 (14)
C4—C3—C2118.06 (13)C24—C23—H23119.3
C4—C3—C14120.79 (13)C22—C23—H23119.3
C2—C3—C14121.14 (13)C21—C22—C23118.32 (14)
C3—C4—C4A121.28 (14)C21—C22—C25121.34 (14)
C3—C4—H4119.4C23—C22—C25120.32 (14)
C4A—C4—H4119.4C17—C18—H18A109.5
C8—C7—C6A110.09 (13)C17—C18—H18B109.5
C8—C7—H7A109.6H18A—C18—H18B109.5
C6A—C7—H7A109.6C17—C18—H18C109.5
C8—C7—H7B109.6H18A—C18—H18C109.5
C6A—C7—H7B109.6H18B—C18—H18C109.5
H7A—C7—H7B108.2C22—C25—H25A109.5
C10—C9—C13121.77 (15)C22—C25—H25B109.5
C10—C9—C8122.42 (14)H25A—C25—H25B109.5
C13—C9—C8115.81 (13)C22—C25—H25C109.5
C9—C10—C10A122.90 (14)H25A—C25—H25C109.5
C9—C10—H10118.6H25B—C25—H25C109.5
C10A—C10—H10118.6C14—C15—C16112.86 (12)
C9—C8—C7113.91 (13)C14—C15—H15A109.0
C9—C8—H8A108.8C16—C15—H15A109.0
C7—C8—H8A108.8C14—C15—H15B109.0
C9—C8—H8B108.8C16—C15—H15B109.0
C7—C8—H8B108.8H15A—C15—H15B107.8
H8A—C8—H8B107.7C18—C17—C16112.87 (14)
O1—C6—C11108.59 (12)C18—C17—H17A109.0
O1—C6—C12103.19 (12)C16—C17—H17A109.0
C11—C6—C12111.55 (13)C18—C17—H17B109.0
O1—C6—C6A107.43 (11)C16—C17—H17B109.0
C11—C6—C6A114.00 (12)H17A—C17—H17B107.8
C12—C6—C6A111.40 (12)C17—C16—C15113.92 (13)
O1—C4A—C4114.70 (13)C17—C16—H16A108.8
O1—C4A—C10B123.32 (13)C15—C16—H16A108.8
C4—C4A—C10B121.97 (13)C17—C16—H16B108.8
C10—C10A—C10B115.39 (12)C15—C16—H16B108.8
C10—C10A—C6A108.19 (11)H16A—C16—H16B107.7
C10B—C10A—C6A109.85 (11)C6—C12—H12A109.5
C10—C10A—H10A107.7C6—C12—H12B109.5
C10B—C10A—H10A107.7H12A—C12—H12B109.5
C6A—C10A—H10A107.7C6—C12—H12C109.5
C1—C10B—C4A114.47 (13)H12A—C12—H12C109.5
C1—C10B—C10A125.35 (13)H12B—C12—H12C109.5
C4A—C10B—C10A120.18 (12)C1—O2—S1118.44 (8)
C24—C19—C20121.03 (13)C9—C13—H13A109.5
C24—C19—S1119.63 (11)C9—C13—H13B109.5
C20—C19—S1119.31 (11)H13A—C13—H13B109.5
C21—C20—C19118.91 (14)C9—C13—H13C109.5
C21—C20—H20120.5H13A—C13—H13C109.5
C19—C20—H20120.5H13B—C13—H13C109.5
C23—C24—C19118.90 (13)C6—C6A—C7115.99 (12)
C23—C24—H24120.5C6—C6A—C10A112.07 (12)
C19—C24—H24120.5C7—C6A—C10A107.98 (12)
C20—C21—C22121.40 (14)C6—C6A—H6A106.8
C20—C21—H21119.3C7—C6A—H6A106.8
C22—C21—H21119.3C10A—C6A—H6A106.8
C3—C14—C15112.63 (12)C4A—O1—C6118.01 (11)

Experimental details

Crystal data
Chemical formulaC28H36O4S
Mr468.63
Crystal system, space groupOrthorhombic, P212121
Temperature (K)100
a, b, c (Å)9.8759 (2), 13.2996 (2), 19.1500 (3)
V3)2515.27 (7)
Z4
Radiation typeCu Kα
µ (mm1)1.39
Crystal size (mm)0.19 × 0.17 × 0.16
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
47731, 4562, 4438
Rint0.034
(sin θ/λ)max1)0.601
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.027, 0.069, 1.04
No. of reflections4562
No. of parameters303
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.25, 0.24
Absolute structureFlack (1983), 1965 Friedel pairs
Absolute structure parameter0.023 (11)

Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

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.

References

First citationBruker (2003). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2005). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationDuchek, J. R. (2004). US Patent No. 2006/0094774-A1.  Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationMechoulam, R. & Gaoni, Y. (1967). Fortschr. Chem. Org. Naturst. 25, 175–213.  CAS PubMed Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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