Download citation
Download citation
link to html
The X-ray study of the title compound, C23H26O8, (I), confirmed the endo,exo-furo­furan­one structure of the important intermediate compound in the process of the total synthesis of (±)-epimagnolin A, which employs a new approach involving a highly diastereoselective C-H insertion reaction [Brown et al. (2001). Tetrahedron Lett. 42, 473-475].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801007425/ya6023sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801007425/ya6023Isup2.hkl
Contains datablock I

CCDC reference: 170299

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.014 Å
  • R factor = 0.086
  • wR factor = 0.334
  • Data-to-parameter ratio = 10.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Red Alert Alert Level A:
TYPE_048 Alert A _exptl_absorpt_correction_T_max is not of type numb. RINTA_01 Alert A The value of Rint is greater than 0.20 Rint given 0.361
Author response: The crystal was of poor quality and only diffracted weakly

Amber Alert Alert Level B:
THETM_01 Alert B The value of sine(theta_max)/wavelength is less than 0.575 Calculated sin(theta_max)/wavelength = 0.5543
Author response: The crystal was only weakly diffracting
PLAT_213  Alert B Atom  O2     has ADP max/min Ratio ...........       4.70
Author response: The -OMe groups are thermally disordered - an attempt to model this did not improve the refinement.

Yellow Alert Alert Level C:
RFACR_01 Alert C The value of the weighted R factor is > 0.25 Weighted R factor given 0.334 PLAT_213 Alert C Atom C3 has ADP max/min Ratio ........... 3.90
2 Alert Level A = Potentially serious problem
2 Alert Level B = Potential problem
2 Alert Level C = Please check

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: SCALEPACK (Otwinoski & Minor, 1997) and COLLECT; data reduction: DENZO (Otwinoski & Minor, 1997), COLLECT and maXus (Mackay et al., 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CAMERON (Watkin et al., 1993); software used to prepare material for publication: WinGX (Farrugia, 1998).

(1S*,4S*,5R*,8R*)-8-(3,4-Dimethoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-3,7- dioxabicyclo[3.3.0]octan-2-one top
Crystal data top
C23H26O8F(000) = 912
Mr = 430.44Dx = 1.318 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 11.839 (2) ÅCell parameters from 2999 reflections
b = 8.0773 (10) Åθ = 3.0–23.2°
c = 22.695 (4) ŵ = 0.10 mm1
β = 91.84 (3)°T = 150 K
V = 2169.1 (6) Å3Block, colourless
Z = 40.10 × 0.10 × 0.10 mm
Data collection top
Nonius Kappa CCD area-detector
diffractometer
2999 independent reflections
Radiation source: Nonius FR591 rotating anode947 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.361
Detector resolution: 9.091 pixels/mm pixels mm-1θmax = 23.2°, θmin = 3.0°
φ and ω scans to fill Ewald sphereh = 1313
Absorption correction: empirical (using intensity measurements)
(SORTAV; Blessing, 1997)
k = 88
Tmin = 0.990, Tmax = 0.990 (?)l = 2525
13956 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.086Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.334H-atom parameters constrained
S = 0.81 w = 1/[σ2(Fo2) + (0.1905P)2]
where P = (Fo2 + 2Fc2)/3
2999 reflections(Δ/σ)max = 0.010
281 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.27 e Å3
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
C10.0859 (9)0.3696 (13)0.0602 (5)0.079 (3)
H1A0.02360.32930.03460.118*
H1B0.05810.39160.09970.118*
H1C0.14560.28570.06280.118*
C20.1774 (15)0.910 (2)0.0272 (10)0.199 (11)
H2A0.12140.87950.05810.298*
H2B0.24700.94640.04540.298*
H2C0.14740.99930.00320.298*
C30.4607 (14)1.0700 (16)0.0764 (6)0.150 (7)
H3A0.47041.17500.05550.225*
H3B0.52831.00150.07230.225*
H3C0.44931.09220.11830.225*
C40.2729 (7)0.5250 (12)0.1148 (4)0.050 (3)
H40.25090.41880.12830.060*
C50.2191 (8)0.5965 (13)0.0668 (4)0.056 (3)
C60.2495 (11)0.7514 (15)0.0457 (5)0.091 (4)
C70.3373 (11)0.8360 (15)0.0754 (5)0.078 (4)
C80.3924 (8)0.7692 (13)0.1245 (5)0.057 (3)
H80.45060.82880.14500.068*
C90.3603 (7)0.6112 (12)0.1432 (4)0.049 (3)
C100.4171 (7)0.5431 (11)0.2002 (4)0.052 (3)
H100.48690.60790.21060.062*
C110.4271 (7)0.2760 (14)0.2384 (5)0.049 (3)
C120.3704 (7)0.3793 (12)0.2854 (4)0.051 (3)
H120.30210.32190.30020.061*
C130.4501 (8)0.4393 (14)0.3378 (5)0.059 (3)
H130.40690.43280.37490.071*
C140.3720 (8)0.6745 (13)0.2974 (4)0.068 (3)
H14A0.38770.78030.27710.082*
H14B0.31180.69280.32600.082*
C150.3380 (7)0.5391 (13)0.2529 (4)0.054 (3)
H150.25620.54350.24060.065*
C160.5580 (8)0.3500 (12)0.3478 (4)0.050 (3)
C170.5734 (9)0.2389 (13)0.3942 (4)0.061 (3)
H170.51310.22180.42020.073*
C180.6743 (8)0.1513 (12)0.4042 (5)0.055 (3)
H180.68190.07510.43600.066*
C190.7611 (7)0.1771 (12)0.3676 (5)0.054 (3)
C200.7496 (8)0.2892 (13)0.3197 (4)0.053 (3)
C210.6506 (8)0.3757 (12)0.3113 (4)0.053 (3)
H210.64430.45430.28020.063*
C220.8290 (8)0.3968 (13)0.2333 (5)0.078 (4)
H22A0.89840.39330.21100.117*
H22B0.81400.51110.24530.117*
H22C0.76560.35600.20860.117*
C230.8817 (9)0.0014 (17)0.4252 (6)0.120 (6)
H23A0.95740.04750.42480.180*
H23B0.82510.08690.42640.180*
H23C0.87550.07210.46010.180*
O10.1307 (6)0.5206 (9)0.0360 (3)0.067 (2)
O20.1940 (14)0.8101 (16)0.0014 (5)0.225 (9)
O30.3652 (9)0.9851 (11)0.0520 (3)0.134 (4)
O40.4454 (4)0.3710 (9)0.1900 (3)0.0537 (19)
O50.4442 (5)0.1297 (9)0.2388 (3)0.0561 (19)
O60.4720 (5)0.6101 (9)0.3259 (3)0.065 (2)
O70.8423 (5)0.2937 (8)0.2851 (3)0.063 (2)
O80.8626 (5)0.0989 (8)0.3730 (3)0.075 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.095 (8)0.066 (8)0.073 (8)0.011 (7)0.028 (6)0.013 (7)
C20.158 (15)0.17 (2)0.26 (3)0.060 (14)0.099 (15)0.144 (18)
C30.236 (17)0.118 (13)0.095 (11)0.144 (13)0.001 (11)0.001 (9)
C40.051 (6)0.047 (6)0.053 (7)0.008 (5)0.011 (5)0.009 (6)
C50.071 (7)0.057 (8)0.040 (7)0.018 (6)0.007 (6)0.005 (6)
C60.153 (12)0.073 (9)0.043 (8)0.055 (9)0.025 (8)0.025 (7)
C70.131 (11)0.067 (9)0.037 (7)0.023 (8)0.000 (7)0.017 (7)
C80.053 (6)0.051 (7)0.068 (8)0.018 (5)0.019 (6)0.014 (6)
C90.038 (6)0.049 (7)0.059 (7)0.003 (5)0.006 (5)0.011 (6)
C100.043 (6)0.030 (6)0.083 (8)0.002 (5)0.003 (6)0.022 (5)
C110.033 (6)0.046 (7)0.068 (8)0.009 (5)0.009 (5)0.003 (7)
C120.043 (6)0.055 (7)0.055 (7)0.003 (5)0.004 (5)0.007 (6)
C130.043 (6)0.073 (9)0.061 (8)0.002 (6)0.008 (5)0.007 (6)
C140.067 (7)0.079 (9)0.058 (7)0.031 (6)0.013 (6)0.015 (6)
C150.042 (6)0.068 (8)0.051 (7)0.007 (5)0.007 (5)0.019 (6)
C160.046 (6)0.057 (7)0.046 (7)0.001 (6)0.008 (5)0.014 (6)
C170.063 (7)0.073 (8)0.047 (7)0.005 (6)0.008 (5)0.014 (6)
C180.042 (6)0.055 (7)0.069 (8)0.002 (6)0.001 (5)0.002 (6)
C190.030 (6)0.044 (7)0.088 (9)0.012 (5)0.006 (6)0.003 (6)
C200.046 (6)0.062 (7)0.053 (7)0.007 (6)0.004 (5)0.002 (6)
C210.047 (6)0.042 (6)0.069 (8)0.000 (6)0.017 (6)0.014 (6)
C220.056 (7)0.079 (9)0.101 (10)0.002 (6)0.012 (6)0.044 (7)
C230.069 (8)0.165 (14)0.129 (12)0.052 (8)0.037 (8)0.107 (11)
O10.097 (5)0.066 (5)0.038 (4)0.021 (4)0.019 (4)0.008 (4)
O20.40 (2)0.159 (12)0.105 (9)0.165 (13)0.153 (11)0.099 (9)
O30.239 (11)0.102 (7)0.060 (6)0.090 (8)0.023 (6)0.029 (5)
O40.046 (4)0.062 (5)0.054 (5)0.001 (3)0.007 (3)0.012 (4)
O50.054 (4)0.049 (5)0.066 (5)0.003 (4)0.003 (3)0.007 (4)
O60.051 (4)0.079 (6)0.064 (5)0.013 (4)0.018 (3)0.026 (4)
O70.040 (4)0.063 (5)0.088 (6)0.006 (3)0.005 (4)0.031 (4)
O80.043 (4)0.085 (6)0.099 (6)0.015 (4)0.022 (4)0.043 (5)
Geometric parameters (Å, º) top
C1—O11.446 (11)C11—C121.526 (13)
C2—O21.010 (14)C12—C151.530 (13)
C3—O31.420 (13)C12—C131.571 (12)
C4—C51.372 (12)C13—O61.431 (10)
C4—C91.388 (12)C13—C161.478 (12)
C5—O11.383 (10)C14—O61.430 (10)
C5—C61.391 (13)C14—C151.534 (12)
C6—O21.325 (14)C16—C171.392 (12)
C6—C71.399 (14)C16—C211.410 (12)
C7—O31.360 (12)C17—C181.401 (12)
C7—C81.383 (13)C18—C191.358 (12)
C8—C91.401 (12)C19—O81.360 (10)
C9—C101.540 (13)C19—C201.417 (12)
C10—O41.450 (10)C20—O71.371 (10)
C10—C151.542 (13)C20—C211.373 (12)
C11—O51.199 (10)C22—O71.446 (10)
C11—O41.363 (11)C23—O81.434 (11)
C5—C4—C9118.6 (10)C16—C13—C12117.4 (9)
C4—C5—O1122.7 (9)O6—C14—C15103.6 (7)
C4—C5—C6122.2 (10)C12—C15—C14103.2 (8)
O1—C5—C6115.2 (9)C12—C15—C10104.0 (7)
O2—C6—C5118.2 (11)C14—C15—C10110.0 (8)
O2—C6—C7123.7 (11)C17—C16—C21117.0 (9)
C5—C6—C7118.1 (11)C17—C16—C13121.5 (9)
O3—C7—C8123.1 (11)C21—C16—C13121.5 (10)
O3—C7—C6115.5 (11)C16—C17—C18122.5 (10)
C8—C7—C6121.4 (11)C19—C18—C17118.8 (10)
C7—C8—C9118.3 (10)C18—C19—O8123.8 (10)
C4—C9—C8121.4 (10)C18—C19—C20120.7 (9)
C4—C9—C10120.7 (9)O8—C19—C20115.4 (9)
C8—C9—C10117.7 (9)O7—C20—C21127.1 (10)
O4—C10—C9107.7 (8)O7—C20—C19113.4 (9)
O4—C10—C15104.7 (7)C21—C20—C19119.5 (9)
C9—C10—C15113.4 (8)C20—C21—C16121.3 (10)
O5—C11—O4122.0 (10)C5—O1—C1117.6 (7)
O5—C11—C12127.7 (10)C2—O2—C6146.7 (17)
O4—C11—C12109.9 (9)C7—O3—C3118.4 (10)
C11—C12—C15103.5 (8)C11—O4—C10111.5 (8)
C11—C12—C13115.5 (7)C14—O6—C13106.5 (8)
C15—C12—C13103.9 (8)C20—O7—C22114.4 (7)
O6—C13—C16109.8 (8)C19—O8—C23116.4 (8)
O6—C13—C12105.2 (8)
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds