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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 3| March 2009| Pages o471-o472

(2S,4aR,6aR,7R,9S,10aS,10bR)-7-Carb­­oxy-2-(3-fur­yl)-6a,10b-di­methyl-4,10-dioxoperhydro­benzo[f]isochromen-9-yl acetate

aDepartment of Medicinal Chemistry, University of Mississippi, 417 Faser Hall, University, MS 38677, USA, bDepartment of Pharmacognosy, School of Pharmacy, University of Mississippi, University, MS 38677, USA, cNational Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, University, MS 38677, USA, and dDepartment of Chemistry and Biochemistry, University of Mississippi, University, MS 38677, USA
*Correspondence e-mail: mavery@olemiss.edu

(Received 18 December 2008; accepted 15 January 2009; online 6 February 2009)

The asymmetric unit of the title compound, C22H26O8, contains two crystallographically independent mol­ecules with closely comparable conformations (r.m.s. overlay = 0.54 Å for 30 non-H atoms). All six-membered rings display chair conformations, with a slight distortion for the lactone ring. The mol­ecules are connected by O—H⋯O hydrogen bonds into chains along [010], with the independent mol­ecules segregated into separate chains. The two mol­ecules in the asymmetric unit face each other in a head-to-tail fashion, with the furan ring of one mol­ecule turned towards the carboxylic acid terminal of the other mol­ecule.

Related literature

For the biosynthesis of Salvinorin A, see: Kutrzeba et al. (2007[Kutrzeba, L., Dayan, F. E., Howell, J. L., Feng, J., Giner, J.-L. & Zjawiony, J. K. (2007). Phytochemistry, 68, 1872-1881.]). For the isolation of Salvinorin A and further synthesis details, see: Lee, Karnati et al. (2005[Lee, D. Y. W., Karnati, V. V. R., He, M., Liu-Chen, L.-Y., Kondaveti, L., Ma, Z., Wang, Y., Chen, Y., Beguin, C., Carlezon, W. A. & Cohen, B. (2005). Bioorg. Med. Chem. Lett. 15, 3744-3747.]); Lee, He et al. (2005[Lee, D. Y., He, M., Kondaveti, L., Liu-Chen, L. Y., Ma, Z., Wang, Y., Chen, Y., Li, J. G., Beguin, C., Carlezon, W. A. J. & Cohen, B. (2005). Bioorg. Med. Chem. Lett. 15, 4169-4173.]); Stewart (2005[Stewart, D. J. (2005). Dissertation thesis, University of Mississippi, USA.]). For details on epimerization at the C-8 stereogenic center, see: Harding et al. (2005[Harding, W. W., Tidgewell, K., Byrd, N., Cobb, H., Dersch, C. M., Butelman, E. R., Rothman, R. B. & Prisinzano, T. E. (2005). J. Med. Chem. 48, 4765-4771.]).

[Scheme 1]

Experimental

Crystal data
  • C22H26O8

  • Mr = 418.43

  • Monoclinic, P 21

  • a = 11.2735 (6) Å

  • b = 16.8015 (9) Å

  • c = 11.3765 (6) Å

  • β = 111.934 (3)°

  • V = 1998.86 (18) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 0.89 mm−1

  • T = 100 (2) K

  • 0.19 × 0.12 × 0.09 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: none

  • 33644 measured reflections

  • 7269 independent reflections

  • 6962 reflections with I > 2σ(I)

  • Rint = 0.034

Refinement
  • R[F2 > 2σ(F2)] = 0.029

  • wR(F2) = 0.074

  • S = 1.10

  • 7269 reflections

  • 549 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.18 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 3360 Friedel pairs

  • Flack parameter: −0.09 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O8—H8A⋯O6i 0.82 1.92 2.7264 (18) 168
O8′—H8′⋯O3′ii 0.82 1.92 2.7308 (17) 172
Symmetry code: (i) [-x, y+{\script{1\over 2}}, -z]; (ii) [-x+1, y-{\script{1\over 2}}, -z+2].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 and 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


Comment top

Diterpenoid salvinorin A is a potent kappa opioid agonist isolated from Mexican mint Salvia divinorum. The biosynthesis of this natural product was studied using synthetic analogues of salvinorin A modified at C-2 and C-18 as chemical probes for in vitro enzymatic reactions. Salvinorin A and its C-8 epimeric counterpart revealed low affinity to the kappa-opioid receptor.

Related literature top

For the biosynthesis of Salvinorin A, see: Kutrzeba et al. (2007). For the isolation of Salvinorin A and further synthesis details, see: Lee, Karnati et al. (2005); Lee, He et al. (2005); Stewart (2005). For details on epimerization at the C-8 stereogenic center, see: Harding et al. (2005).

Experimental top

The starting material for synthesis, salvinorin A, was isolated from dry plant material, and purified according to a previously published procedure (Stewart, 2005). Salvinorin A acid was synthesized following Lee, He et al. (2005), by using LiI in pyridine as a selective hydrolyzing agent of C-4 methyl ester.

Refinement top

All H atoms were visible in difference maps, but were placed geometrically and treated as riding atoms for refinement, with the following constraints: C—H = 0.93 Å, Uiso(H) = 1.2Ueq(C) for Csp2, C—H = 0.98 Å, Uiso(H) = 1.2Ueq(C) for CH, C—H = 0.97 Å, Uiso(H) = 1.2Ueq(C) for CH2, C—H = 0.96 Å, Uiso(H) = 1.5Ueq(C) CH3, O—H = 0.82 Å, Uiso(H) = 1.5Ueq(O) for OH.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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. One molecule in the asymmetric unit of the title compound with displacement ellipsoids drawn at the 50% probability level for non-H atoms. The second molecule is closely comparable.
(2S,4aR,6aR,7R,9S,10aS,10bR)- 7-Carboxy-2-(3-furyl)-6a,10b-dimethyl-4,10- dioxoperhydrobenzo[f]isochromen-9-yl acetate top
Crystal data top
C22H26O8F(000) = 888
Mr = 418.43Dx = 1.390 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ybCell parameters from 9847 reflections
a = 11.2735 (6) Åθ = 4.2–69.3°
b = 16.8015 (9) ŵ = 0.89 mm1
c = 11.3765 (6) ÅT = 100 K
β = 111.934 (3)°Block, colourless
V = 1998.86 (18) Å30.19 × 0.12 × 0.09 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer
6962 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube, Siemens KFF Cu 2 K90Rint = 0.034
Graphite monochromatorθmax = 69.7°, θmin = 4.2°
ϕ and ω scansh = 1313
33644 measured reflectionsk = 2020
7269 independent reflectionsl = 1313
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)] = 0.029H-atom parameters constrained
wR(F2) = 0.074 w = 1/[σ2(Fo2) + (0.0314P)2 + 0.6446P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.001
7269 reflectionsΔρmax = 0.22 e Å3
549 parametersΔρmin = 0.18 e Å3
1 restraintAbsolute structure: Flack (1983), 3360 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.09 (13)
Crystal data top
C22H26O8V = 1998.86 (18) Å3
Mr = 418.43Z = 4
Monoclinic, P21Cu Kα radiation
a = 11.2735 (6) ŵ = 0.89 mm1
b = 16.8015 (9) ÅT = 100 K
c = 11.3765 (6) Å0.19 × 0.12 × 0.09 mm
β = 111.934 (3)°
Data collection top
Bruker APEXII CCD
diffractometer
6962 reflections with I > 2σ(I)
33644 measured reflectionsRint = 0.034
7269 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.029H-atom parameters constrained
wR(F2) = 0.074Δρmax = 0.22 e Å3
S = 1.10Δρmin = 0.18 e Å3
7269 reflectionsAbsolute structure: Flack (1983), 3360 Friedel pairs
549 parametersAbsolute structure parameter: 0.09 (13)
1 restraint
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
C170.15137 (16)0.28832 (12)0.49869 (18)0.0206 (4)
C210.01037 (17)0.36406 (10)0.21255 (17)0.0184 (4)
C100.05570 (16)0.40092 (10)0.18239 (17)0.0171 (4)
H100.14600.40790.19530.021*
C20.02643 (18)0.44739 (11)0.03640 (17)0.0200 (4)
H20.11870.44460.01670.024*
C130.22704 (17)0.12615 (11)0.32982 (18)0.0209 (4)
C30.00836 (19)0.53085 (11)0.00734 (19)0.0216 (4)
H3A0.10050.53560.03410.026*
H3B0.02080.56990.05330.026*
C2'0.52134 (17)0.21987 (11)0.57588 (17)0.0184 (4)
H2'0.42930.22140.52600.022*
C70.07910 (19)0.43150 (12)0.44293 (18)0.0230 (4)
H7A0.00870.42270.43470.028*
H7B0.12890.44450.53070.028*
C10.01037 (16)0.38607 (10)0.04262 (18)0.0184 (4)
C140.25349 (19)0.05608 (11)0.4068 (2)0.0260 (4)
H140.22130.04370.46880.031*
C60.08460 (18)0.50046 (11)0.35771 (18)0.0220 (4)
H6A0.17340.51160.37230.026*
H6B0.04900.54750.38160.026*
C200.08067 (17)0.30143 (11)0.25474 (18)0.0200 (4)
H20A0.11740.27100.17820.030*
H20B0.13390.34660.25140.030*
H20C0.07440.26880.32610.030*
C120.13705 (17)0.19141 (11)0.33016 (17)0.0198 (4)
H120.05130.16810.30330.024*
C50.01218 (16)0.48472 (11)0.21544 (17)0.0188 (4)
C80.13200 (17)0.35598 (11)0.40574 (17)0.0194 (4)
H80.21730.36980.40790.023*
C220.09694 (18)0.34694 (12)0.34524 (18)0.0229 (4)
H22A0.05850.30750.38090.034*
H22B0.11100.39490.39460.034*
H22C0.17720.32740.34590.034*
C90.05392 (16)0.33013 (11)0.26855 (17)0.0177 (4)
C160.2942 (2)0.11820 (13)0.2545 (2)0.0297 (4)
H160.29560.15550.19470.036*
C110.13007 (17)0.26038 (11)0.24228 (17)0.0184 (4)
H11A0.08880.24320.15500.022*
H11B0.21580.27800.25470.022*
C180.03699 (18)0.63203 (11)0.17068 (19)0.0227 (4)
C190.13340 (17)0.49154 (11)0.18207 (19)0.0220 (4)
H19A0.15510.46730.24780.033*
H19B0.17810.46490.10320.033*
H19C0.15760.54670.17440.033*
C40.05507 (17)0.54636 (11)0.13572 (19)0.0202 (4)
H40.14720.53870.15850.024*
C150.33360 (19)0.01185 (12)0.3722 (2)0.0296 (4)
H150.36670.03700.40780.036*
O60.07866 (12)0.32321 (8)0.14752 (12)0.0217 (3)
O20.04114 (12)0.43277 (8)0.16960 (12)0.0213 (3)
O40.17443 (12)0.21504 (8)0.46368 (12)0.0229 (3)
O10.08635 (12)0.33368 (8)0.00508 (12)0.0223 (3)
O70.11380 (13)0.66586 (8)0.25955 (14)0.0309 (3)
O80.07111 (13)0.66571 (8)0.09307 (13)0.0281 (3)
H8A0.07680.71080.11790.042*
O30.15754 (12)0.29677 (8)0.60630 (12)0.0246 (3)
O50.36018 (14)0.04804 (9)0.27771 (16)0.0341 (3)
O4'0.33614 (12)0.44634 (7)0.94502 (12)0.0201 (3)
O3'0.34121 (12)0.36271 (7)1.09451 (11)0.0196 (3)
O2'0.58986 (12)0.23688 (7)0.49500 (12)0.0196 (3)
O1'0.62849 (12)0.33263 (8)0.69732 (12)0.0220 (3)
O8'0.61511 (12)0.00106 (7)0.76991 (13)0.0221 (3)
H8'0.62480.04290.80360.033*
O6'0.45406 (13)0.33889 (8)0.41371 (13)0.0287 (3)
O7'0.42832 (12)0.00338 (7)0.79601 (14)0.0253 (3)
O5'0.12409 (13)0.60011 (8)0.65291 (13)0.0253 (3)
C17'0.35561 (16)0.37244 (10)0.99497 (17)0.0173 (4)
C9'0.47726 (16)0.33266 (10)0.85748 (16)0.0166 (4)
C3'0.55835 (18)0.13668 (10)0.63141 (18)0.0183 (4)
H3'10.64980.13410.67890.022*
H3'20.53640.09770.56380.022*
C21'0.54660 (18)0.30114 (11)0.41882 (17)0.0211 (4)
C1'0.55327 (16)0.27937 (10)0.68357 (16)0.0165 (3)
C13'0.30056 (17)0.53252 (10)0.76765 (17)0.0184 (4)
C16'0.17621 (19)0.54538 (11)0.74745 (19)0.0232 (4)
H16'0.13200.52050.79170.028*
C14'0.32831 (18)0.58268 (11)0.67923 (19)0.0233 (4)
H14'0.40630.58740.66950.028*
C12'0.39011 (17)0.47249 (11)0.85204 (17)0.0185 (4)
H12'0.47200.49880.89790.022*
C4'0.48608 (17)0.11855 (10)0.71910 (17)0.0180 (4)
H4'0.39490.12470.66770.022*
C11'0.41363 (17)0.40455 (10)0.77524 (17)0.0175 (4)
H11C0.46770.42330.73180.021*
H11D0.33270.38810.71140.021*
C5'0.51693 (16)0.17822 (10)0.83185 (17)0.0170 (4)
C15'0.22000 (19)0.62152 (11)0.61333 (19)0.0241 (4)
H15'0.21130.65810.54930.029*
C6'0.42909 (18)0.16156 (11)0.90570 (18)0.0210 (4)
H6'10.34320.15150.84530.025*
H6'20.45850.11360.95550.025*
C10'0.48050 (16)0.26283 (10)0.76984 (16)0.0160 (4)
H10'0.39140.25710.71160.019*
C22'0.62893 (19)0.31710 (12)0.34423 (19)0.0250 (4)
H22D0.59240.35960.28530.037*
H22E0.63410.27000.29870.037*
H22F0.71310.33200.40080.037*
C8'0.38328 (17)0.30620 (10)0.91970 (17)0.0179 (4)
H8'10.30220.29480.84990.021*
C19'0.65936 (17)0.17049 (12)0.92042 (18)0.0225 (4)
H19D0.67150.19301.00170.034*
H19E0.71170.19840.88410.034*
H19F0.68310.11530.93040.034*
C18'0.50473 (17)0.03240 (11)0.76516 (17)0.0183 (4)
C7'0.42364 (19)0.22877 (11)0.99402 (18)0.0223 (4)
H7'10.36300.21531.03290.027*
H7'20.50700.23551.06090.027*
C20'0.60724 (17)0.35762 (11)0.95727 (18)0.0213 (4)
H20D0.59460.39911.00950.032*
H20E0.66150.37670.91550.032*
H20F0.64670.31261.00910.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C170.0127 (8)0.0244 (9)0.0235 (10)0.0000 (7)0.0056 (7)0.0009 (8)
C210.0201 (9)0.0183 (9)0.0200 (9)0.0027 (7)0.0112 (7)0.0016 (8)
C100.0137 (8)0.0179 (9)0.0200 (9)0.0004 (7)0.0066 (7)0.0011 (7)
C20.0213 (9)0.0199 (9)0.0175 (9)0.0011 (7)0.0057 (7)0.0005 (8)
C130.0174 (9)0.0194 (9)0.0232 (10)0.0038 (7)0.0046 (7)0.0038 (8)
C30.0238 (9)0.0183 (9)0.0231 (9)0.0012 (7)0.0092 (7)0.0023 (8)
C2'0.0171 (9)0.0194 (9)0.0201 (9)0.0009 (7)0.0086 (7)0.0024 (8)
C70.0256 (10)0.0236 (9)0.0198 (10)0.0015 (8)0.0084 (8)0.0037 (8)
C10.0154 (9)0.0159 (9)0.0252 (10)0.0032 (7)0.0092 (7)0.0010 (8)
C140.0279 (10)0.0199 (9)0.0272 (10)0.0013 (8)0.0070 (8)0.0010 (8)
C60.0223 (9)0.0205 (9)0.0222 (9)0.0002 (7)0.0069 (7)0.0053 (8)
C200.0180 (9)0.0213 (9)0.0210 (9)0.0006 (7)0.0074 (7)0.0021 (8)
C120.0188 (9)0.0201 (9)0.0197 (9)0.0014 (7)0.0062 (7)0.0015 (7)
C50.0172 (9)0.0176 (9)0.0215 (9)0.0008 (7)0.0070 (7)0.0022 (8)
C80.0170 (9)0.0217 (9)0.0193 (9)0.0005 (7)0.0064 (7)0.0009 (8)
C220.0222 (9)0.0272 (10)0.0217 (9)0.0007 (8)0.0108 (7)0.0002 (8)
C90.0167 (8)0.0181 (9)0.0190 (9)0.0011 (7)0.0076 (7)0.0012 (8)
C160.0296 (11)0.0256 (10)0.0369 (12)0.0056 (8)0.0160 (9)0.0047 (9)
C110.0165 (8)0.0203 (9)0.0188 (9)0.0008 (7)0.0071 (7)0.0023 (7)
C180.0200 (10)0.0205 (9)0.0285 (11)0.0002 (7)0.0101 (8)0.0022 (8)
C190.0185 (9)0.0209 (9)0.0286 (10)0.0019 (7)0.0111 (8)0.0006 (8)
C40.0160 (9)0.0183 (9)0.0264 (10)0.0006 (7)0.0082 (7)0.0015 (8)
C150.0293 (11)0.0166 (9)0.0384 (12)0.0013 (8)0.0074 (9)0.0012 (9)
O60.0187 (6)0.0196 (6)0.0267 (7)0.0009 (5)0.0083 (5)0.0008 (6)
O20.0253 (7)0.0201 (6)0.0174 (7)0.0037 (5)0.0069 (5)0.0017 (5)
O40.0267 (7)0.0221 (7)0.0199 (7)0.0041 (5)0.0087 (5)0.0027 (6)
O10.0206 (6)0.0242 (7)0.0212 (7)0.0027 (5)0.0069 (5)0.0010 (6)
O70.0258 (7)0.0225 (7)0.0362 (8)0.0001 (6)0.0021 (6)0.0070 (7)
O80.0260 (7)0.0161 (6)0.0354 (8)0.0042 (5)0.0039 (6)0.0037 (6)
O30.0232 (7)0.0309 (7)0.0199 (7)0.0024 (5)0.0084 (5)0.0012 (6)
O50.0321 (8)0.0276 (8)0.0475 (9)0.0056 (6)0.0203 (7)0.0017 (7)
O4'0.0247 (7)0.0172 (6)0.0204 (7)0.0027 (5)0.0107 (5)0.0005 (5)
O3'0.0228 (7)0.0198 (6)0.0177 (6)0.0008 (5)0.0092 (5)0.0016 (5)
O2'0.0233 (7)0.0178 (6)0.0203 (7)0.0031 (5)0.0112 (5)0.0027 (5)
O1'0.0227 (6)0.0178 (6)0.0292 (7)0.0028 (5)0.0139 (6)0.0011 (6)
O8'0.0239 (7)0.0146 (6)0.0318 (7)0.0032 (5)0.0149 (6)0.0057 (6)
O6'0.0266 (7)0.0284 (7)0.0334 (8)0.0101 (6)0.0138 (6)0.0108 (6)
O7'0.0249 (7)0.0172 (6)0.0395 (8)0.0016 (5)0.0184 (6)0.0005 (6)
O5'0.0257 (7)0.0217 (7)0.0292 (7)0.0066 (5)0.0111 (6)0.0031 (6)
C17'0.0132 (8)0.0174 (9)0.0187 (9)0.0002 (6)0.0030 (7)0.0002 (8)
C9'0.0165 (8)0.0155 (8)0.0183 (9)0.0014 (7)0.0071 (7)0.0020 (7)
C3'0.0212 (9)0.0148 (8)0.0200 (9)0.0003 (7)0.0088 (7)0.0021 (7)
C21'0.0239 (9)0.0187 (9)0.0183 (9)0.0005 (7)0.0051 (7)0.0000 (7)
C1'0.0151 (8)0.0146 (8)0.0190 (9)0.0037 (7)0.0055 (7)0.0043 (7)
C13'0.0243 (10)0.0122 (8)0.0193 (9)0.0006 (7)0.0088 (7)0.0045 (7)
C16'0.0292 (10)0.0191 (9)0.0250 (10)0.0042 (8)0.0145 (8)0.0033 (8)
C14'0.0247 (10)0.0189 (9)0.0287 (11)0.0008 (8)0.0126 (8)0.0007 (8)
C12'0.0179 (9)0.0170 (9)0.0207 (9)0.0030 (7)0.0075 (7)0.0018 (7)
C4'0.0158 (9)0.0162 (9)0.0225 (9)0.0004 (7)0.0079 (7)0.0010 (8)
C11'0.0192 (9)0.0163 (8)0.0193 (9)0.0012 (7)0.0096 (7)0.0006 (7)
C5'0.0180 (9)0.0141 (8)0.0187 (9)0.0006 (7)0.0069 (7)0.0005 (7)
C15'0.0329 (11)0.0156 (9)0.0261 (10)0.0005 (8)0.0138 (8)0.0015 (8)
C6'0.0273 (10)0.0149 (8)0.0230 (9)0.0016 (7)0.0121 (8)0.0030 (8)
C10'0.0135 (8)0.0154 (9)0.0180 (9)0.0003 (6)0.0045 (7)0.0007 (7)
C22'0.0278 (10)0.0249 (10)0.0232 (10)0.0016 (8)0.0108 (8)0.0059 (8)
C8'0.0172 (8)0.0178 (9)0.0194 (9)0.0003 (7)0.0077 (7)0.0008 (7)
C19'0.0233 (10)0.0189 (9)0.0219 (10)0.0037 (7)0.0045 (7)0.0004 (8)
C18'0.0212 (9)0.0154 (9)0.0187 (9)0.0017 (7)0.0079 (7)0.0035 (7)
C7'0.0275 (10)0.0196 (9)0.0227 (10)0.0035 (7)0.0128 (8)0.0017 (8)
C20'0.0198 (9)0.0190 (9)0.0242 (10)0.0003 (7)0.0070 (7)0.0041 (8)
Geometric parameters (Å, º) top
C17—O31.208 (2)C4—H40.980
C17—O41.349 (2)C15—O51.362 (3)
C17—C81.512 (3)C15—H150.930
C21—O61.213 (2)O8—H8A0.820
C21—O21.348 (2)O4'—C17'1.349 (2)
C21—C221.488 (3)O4'—C12'1.471 (2)
C10—C11.504 (3)O3'—C17'1.214 (2)
C10—C91.546 (3)O2'—C21'1.356 (2)
C10—C51.582 (2)O1'—C1'1.202 (2)
C10—H100.980O8'—C18'1.334 (2)
C2—O21.440 (2)O8'—H8'0.820
C2—C11.523 (3)O6'—C21'1.204 (2)
C2—C31.525 (3)O7'—C18'1.205 (2)
C2—H20.980O5'—C15'1.366 (2)
C13—C161.345 (3)O5'—C16'1.370 (2)
C13—C141.431 (3)C17'—C8'1.506 (2)
C13—C121.495 (3)C9'—C11'1.532 (2)
C3—C41.536 (3)C9'—C20'1.539 (2)
C3—H3A0.970C9'—C8'1.543 (2)
C3—H3B0.970C9'—C10'1.549 (2)
C2'—O2'1.434 (2)C3'—C4'1.536 (2)
C2'—C1'1.517 (3)C3'—H3'10.970
C2'—C3'1.526 (2)C3'—H3'20.970
C2'—H2'0.980C21'—C22'1.497 (3)
C7—C61.527 (3)C1'—C10'1.522 (2)
C7—C81.527 (3)C13'—C16'1.351 (3)
C7—H7A0.970C13'—C14'1.434 (3)
C7—H7B0.970C13'—C12'1.495 (3)
C1—O11.206 (2)C16'—H16'0.930
C14—C151.337 (3)C14'—C15'1.340 (3)
C14—H140.930C14'—H14'0.930
C6—C51.539 (2)C12'—C11'1.520 (2)
C6—H6A0.970C12'—H12'0.980
C6—H6B0.970C4'—C18'1.527 (2)
C20—C91.543 (2)C4'—C5'1.561 (3)
C20—H20A0.960C4'—H4'0.980
C20—H20B0.960C11'—H11C0.970
C20—H20C0.960C11'—H11D0.970
C12—O41.471 (2)C5'—C6'1.545 (2)
C12—C111.513 (3)C5'—C19'1.550 (2)
C12—H120.980C5'—C10'1.572 (2)
C5—C191.544 (2)C15'—H15'0.930
C5—C41.567 (3)C6'—C7'1.528 (3)
C8—C91.541 (2)C6'—H6'10.970
C8—H80.980C6'—H6'20.970
C22—H22A0.960C10'—H10'0.980
C22—H22B0.960C22'—H22D0.960
C22—H22C0.960C22'—H22E0.960
C9—C111.546 (2)C22'—H22F0.960
C16—O51.366 (3)C8'—C7'1.525 (2)
C16—H160.930C8'—H8'10.980
C11—H11A0.970C19'—H19D0.960
C11—H11B0.970C19'—H19E0.960
C18—O71.200 (2)C19'—H19F0.960
C18—O81.335 (2)C7'—H7'10.970
C18—C41.527 (3)C7'—H7'20.970
C19—H19A0.960C20'—H20D0.960
C19—H19B0.960C20'—H20E0.960
C19—H19C0.960C20'—H20F0.960
O3—C17—O4117.51 (17)C14—C15—H15124.6
O3—C17—C8123.97 (17)O5—C15—H15124.6
O4—C17—C8118.25 (15)C21—O2—C2114.88 (14)
O6—C21—O2121.98 (16)C17—O4—C12122.60 (14)
O6—C21—C22126.11 (17)C18—O8—H8A109.5
O2—C21—C22111.91 (16)C15—O5—C16105.86 (16)
C1—C10—C9115.10 (15)C17'—O4'—C12'122.14 (14)
C1—C10—C5108.90 (14)C21'—O2'—C2'114.68 (14)
C9—C10—C5117.10 (15)C18'—O8'—H8'109.5
C1—C10—H10104.8C15'—O5'—C16'106.00 (14)
C9—C10—H10104.8O3'—C17'—O4'117.37 (16)
C5—C10—H10104.8O3'—C17'—C8'124.00 (16)
O2—C2—C1110.60 (14)O4'—C17'—C8'118.44 (15)
O2—C2—C3107.88 (15)C11'—C9'—C20'109.58 (14)
C1—C2—C3110.20 (15)C11'—C9'—C8'105.19 (14)
O2—C2—H2109.4C20'—C9'—C8'111.58 (14)
C1—C2—H2109.4C11'—C9'—C10'108.80 (14)
C3—C2—H2109.4C20'—C9'—C10'115.87 (14)
C16—C13—C14105.66 (17)C8'—C9'—C10'105.21 (14)
C16—C13—C12128.21 (18)C2'—C3'—C4'108.73 (14)
C14—C13—C12126.05 (17)C2'—C3'—H3'1109.9
C2—C3—C4109.27 (15)C4'—C3'—H3'1109.9
C2—C3—H3A109.8C2'—C3'—H3'2109.9
C4—C3—H3A109.8C4'—C3'—H3'2109.9
C2—C3—H3B109.8H3'1—C3'—H3'2108.3
C4—C3—H3B109.8O6'—C21'—O2'123.28 (17)
H3A—C3—H3B108.3O6'—C21'—C22'126.00 (17)
O2'—C2'—C1'111.40 (14)O2'—C21'—C22'110.72 (16)
O2'—C2'—C3'108.58 (14)O1'—C1'—C2'122.59 (16)
C1'—C2'—C3'108.88 (15)O1'—C1'—C10'125.18 (16)
O2'—C2'—H2'109.3C2'—C1'—C10'112.22 (14)
C1'—C2'—H2'109.3C16'—C13'—C14'105.75 (16)
C3'—C2'—H2'109.3C16'—C13'—C12'128.77 (17)
C6—C7—C8109.98 (15)C14'—C13'—C12'125.13 (16)
C6—C7—H7A109.7C13'—C16'—O5'110.76 (16)
C8—C7—H7A109.7C13'—C16'—H16'124.6
C6—C7—H7B109.7O5'—C16'—H16'124.6
C8—C7—H7B109.7C15'—C14'—C13'106.67 (17)
H7A—C7—H7B108.2C15'—C14'—H14'126.7
O1—C1—C10125.78 (17)C13'—C14'—H14'126.7
O1—C1—C2122.15 (17)O4'—C12'—C13'107.57 (14)
C10—C1—C2112.04 (15)O4'—C12'—C11'113.40 (14)
C15—C14—C13106.63 (18)C13'—C12'—C11'111.01 (15)
C15—C14—H14126.7O4'—C12'—H12'108.2
C13—C14—H14126.7C13'—C12'—H12'108.2
C7—C6—C5113.95 (15)C11'—C12'—H12'108.2
C7—C6—H6A108.8C18'—C4'—C3'111.86 (14)
C5—C6—H6A108.8C18'—C4'—C5'111.53 (15)
C7—C6—H6B108.8C3'—C4'—C5'113.38 (14)
C5—C6—H6B108.8C18'—C4'—H4'106.5
H6A—C6—H6B107.7C3'—C4'—H4'106.5
C9—C20—H20A109.5C5'—C4'—H4'106.5
C9—C20—H20B109.5C12'—C11'—C9'112.55 (14)
H20A—C20—H20B109.5C12'—C11'—H11C109.1
C9—C20—H20C109.5C9'—C11'—H11C109.1
H20A—C20—H20C109.5C12'—C11'—H11D109.1
H20B—C20—H20C109.5C9'—C11'—H11D109.1
O4—C12—C13105.53 (14)H11C—C11'—H11D107.8
O4—C12—C11113.56 (14)C6'—C5'—C19'110.49 (15)
C13—C12—C11115.33 (15)C6'—C5'—C4'109.82 (14)
O4—C12—H12107.3C19'—C5'—C4'109.82 (14)
C13—C12—H12107.3C6'—C5'—C10'107.14 (14)
C11—C12—H12107.3C19'—C5'—C10'113.65 (14)
C6—C5—C19110.08 (14)C4'—C5'—C10'105.75 (14)
C6—C5—C4109.75 (15)C14'—C15'—O5'110.82 (17)
C19—C5—C4109.75 (15)C14'—C15'—H15'124.6
C6—C5—C10108.25 (14)O5'—C15'—H15'124.6
C19—C5—C10113.76 (14)C7'—C6'—C5'114.53 (15)
C4—C5—C10105.10 (14)C7'—C6'—H6'1108.6
C17—C8—C7113.59 (15)C5'—C6'—H6'1108.6
C17—C8—C9112.03 (15)C7'—C6'—H6'2108.6
C7—C8—C9112.36 (15)C5'—C6'—H6'2108.6
C17—C8—H8106.1H6'1—C6'—H6'2107.6
C7—C8—H8106.1C1'—C10'—C9'115.14 (14)
C9—C8—H8106.1C1'—C10'—C5'109.95 (14)
C21—C22—H22A109.5C9'—C10'—C5'117.47 (14)
C21—C22—H22B109.5C1'—C10'—H10'104.2
H22A—C22—H22B109.5C9'—C10'—H10'104.2
C21—C22—H22C109.5C5'—C10'—H10'104.2
H22A—C22—H22C109.5C21'—C22'—H22D109.5
H22B—C22—H22C109.5C21'—C22'—H22E109.5
C8—C9—C20111.05 (14)H22D—C22'—H22E109.5
C8—C9—C10106.71 (14)C21'—C22'—H22F109.5
C20—C9—C10114.89 (14)H22D—C22'—H22F109.5
C8—C9—C11105.14 (14)H22E—C22'—H22F109.5
C20—C9—C11109.83 (15)C17'—C8'—C7'113.41 (14)
C10—C9—C11108.72 (14)C17'—C8'—C9'111.80 (14)
C13—C16—O5110.99 (19)C7'—C8'—C9'112.71 (15)
C13—C16—H16124.5C17'—C8'—H8'1106.1
O5—C16—H16124.5C7'—C8'—H8'1106.1
C12—C11—C9110.38 (15)C9'—C8'—H8'1106.1
C12—C11—H11A109.6C5'—C19'—H19D109.5
C9—C11—H11A109.6C5'—C19'—H19E109.5
C12—C11—H11B109.6H19D—C19'—H19E109.5
C9—C11—H11B109.6C5'—C19'—H19F109.5
H11A—C11—H11B108.1H19D—C19'—H19F109.5
O7—C18—O8123.35 (18)H19E—C19'—H19F109.5
O7—C18—C4122.76 (17)O7'—C18'—O8'123.29 (17)
O8—C18—C4113.89 (16)O7'—C18'—C4'123.43 (16)
C5—C19—H19A109.5O8'—C18'—C4'113.26 (15)
C5—C19—H19B109.5C8'—C7'—C6'110.04 (15)
H19A—C19—H19B109.5C8'—C7'—H7'1109.7
C5—C19—H19C109.5C6'—C7'—H7'1109.7
H19A—C19—H19C109.5C8'—C7'—H7'2109.7
H19B—C19—H19C109.5C6'—C7'—H7'2109.7
C18—C4—C3112.41 (16)H7'1—C7'—H7'2108.2
C18—C4—C5111.84 (15)C9'—C20'—H20D109.5
C3—C4—C5112.27 (15)C9'—C20'—H20E109.5
C18—C4—H4106.6H20D—C20'—H20E109.5
C3—C4—H4106.6C9'—C20'—H20F109.5
C5—C4—H4106.6H20D—C20'—H20F109.5
C14—C15—O5110.86 (18)H20E—C20'—H20F109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O8—H8A···O6i0.821.922.7264 (18)168
O8—H8···O3ii0.821.922.7308 (17)172
Symmetry codes: (i) x, y+1/2, z; (ii) x+1, y1/2, z+2.

Experimental details

Crystal data
Chemical formulaC22H26O8
Mr418.43
Crystal system, space groupMonoclinic, P21
Temperature (K)100
a, b, c (Å)11.2735 (6), 16.8015 (9), 11.3765 (6)
β (°) 111.934 (3)
V3)1998.86 (18)
Z4
Radiation typeCu Kα
µ (mm1)0.89
Crystal size (mm)0.19 × 0.12 × 0.09
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
33644, 7269, 6962
Rint0.034
(sin θ/λ)max1)0.608
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.074, 1.10
No. of reflections7269
No. of parameters549
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.18
Absolute structureFlack (1983), 3360 Friedel pairs
Absolute structure parameter0.09 (13)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O8—H8A···O6i0.821.922.7264 (18)167.8
O8'—H8'···O3'ii0.821.922.7308 (17)171.5
Symmetry codes: (i) x, y+1/2, z; (ii) x+1, y1/2, z+2.
 

Acknowledgements

The authors thank the Center for Disease Control and Prevention, USA, for providing financial assistance (CDC cooperative agreements 1UO1CI000211–03 and1UO1 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.

References

First citationBruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationHarding, W. W., Tidgewell, K., Byrd, N., Cobb, H., Dersch, C. M., Butelman, E. R., Rothman, R. B. & Prisinzano, T. E. (2005). J. Med. Chem. 48, 4765–4771.  Web of Science CrossRef PubMed CAS Google Scholar
First citationKutrzeba, L., Dayan, F. E., Howell, J. L., Feng, J., Giner, J.-L. & Zjawiony, J. K. (2007). Phytochemistry, 68, 1872–1881.  Web of Science CrossRef PubMed CAS Google Scholar
First citationLee, D. Y., He, M., Kondaveti, L., Liu-Chen, L. Y., Ma, Z., Wang, Y., Chen, Y., Li, J. G., Beguin, C., Carlezon, W. A. J. & Cohen, B. (2005). Bioorg. Med. Chem. Lett. 15, 4169–4173.  Web of Science CrossRef PubMed CAS Google Scholar
First citationLee, D. Y. W., Karnati, V. V. R., He, M., Liu-Chen, L.-Y., Kondaveti, L., Ma, Z., Wang, Y., Chen, Y., Beguin, C., Carlezon, W. A. & Cohen, B. (2005). Bioorg. Med. Chem. Lett. 15, 3744–3747.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationStewart, D. J. (2005). Dissertation thesis, University of Mississippi, USA.  Google Scholar

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Volume 65| Part 3| March 2009| Pages o471-o472
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