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

Gul, W.; Carvalho, P.; Berberich, D.W.; Avery, M.A.; ElSohly, M.A.

doi:10.1107/S1600536808022010

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1686

doi:10.1107/S1600536808022010

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

Waseem Gul,^a,^b Paulo Carvalho,^c David W. Berberich,^d Mitchell A. Avery ^c,^e,^f and Mahmoud A. ElSohly ^b,^g ^*

^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 ). For the synthesis of Δ⁹—THC-tosylate, see: Duchek (2004 ).

Experimental

Crystal data

C₂₈H₃₆O₄S
M_r = 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)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.069
S = 1.04
4562 reflections
303 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808022010/nc2105sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808022010/nc2105Isup2.hkl

checkCIF report

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).

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

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

C₂₈H₃₆O₄S	F(000) = 1008
M_r = 468.63	D_x = 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 = 4.1–67.4°
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 top

Bruker SMART CCD area-detector diffractometer	4438 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube, Siemens KFF Cu 2 K90	R_int = 0.034
Graphite monochromator	θ_max = 68.0°, θ_min = 4.1°
ϕ and ω scans	h = −11→11
47731 measured reflections	k = −15→15
4562 independent reflections	l = −23→23

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.027	H-atom parameters constrained
wR(F²) = 0.069	w = 1/[σ²(F_o²) + (0.0429P)² + 0.4744P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.002
4562 reflections	Δρ_max = 0.25 e Å⁻³
303 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1965 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.023 (11)

Crystal data top

C₂₈H₃₆O₄S	V = 2515.27 (7) Å³
M_r = 468.63	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
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

Data collection top

Bruker SMART CCD area-detector diffractometer	4438 reflections with I > 2σ(I)
47731 measured reflections	R_int = 0.034
4562 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	H-atom parameters constrained
wR(F²) = 0.069	Δρ_max = 0.25 e Å⁻³
S = 1.04	Δρ_min = −0.24 e Å⁻³
4562 reflections	Absolute structure: Flack (1983), 1965 Friedel pairs
303 parameters	Absolute 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

	x	y	z	U_iso*/U_eq
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) top

	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, º) top

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)

Experimental details

Crystal data
Chemical formula	C₂₈H₃₆O₄S
M_r	468.63
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	9.8759 (2), 13.2996 (2), 19.1500 (3)
V (Å³)	2515.27 (7)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	1.39
Crystal size (mm)	0.19 × 0.17 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	47731, 4562, 4438
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.069, 1.04
No. of reflections	4562
No. of parameters	303
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.24
Absolute structure	Flack (1983), 1965 Friedel pairs
Absolute structure parameter	0.023 (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

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

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