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The title compound, C20H16O7, is an intermediate in the total synthesis of (±)-asarinin. The molecular structure contains four chiral centres and crystallizes as two independent mol­ecules. The chirality of the two mol­ecules is the same, but they adopt different conformations. The compound is enantiomeric, with the second enantiomer arising from the centrosymmetric nature of the space group.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801007437/na6072sup1.cif
Contains datablocks global, s92

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801007437/na6072Isup2.hkl
Contains datablock I

CCDC reference: 170312

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.063
  • wR factor = 0.148
  • Data-to-parameter ratio = 14.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry
Red Alert Alert Level A:
RINTA_01 Alert A The value of Rint is greater than 0.20 Rint given 0.229
1 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
0 Alert Level C = Please check

Computing details top

Cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990).

(s92) top
Crystal data top
C20H16O7F(000) = 1536
Mr = 368.33Dx = 1.527 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 12.996 (3) ÅCell parameters from 25343 reflections
b = 5.8243 (12) Åθ = 2.9–27.5°
c = 42.693 (9) ŵ = 0.12 mm1
β = 97.42 (3)°T = 150 K
V = 3204.4 (11) Å3Needle/plate, colourless
Z = 80.2 × 0.05 × 0.01 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
2259 reflections with I > 2σ(I)
φ and ω scans to fill Ewald SphereRint = 0.229
Absorption correction: multi-scan
(Blessing, 1997)
θmax = 27.5°, θmin = 3.0°
Tmin = 0.977, Tmax = 0.999h = 1616
34875 measured reflectionsk = 77
7091 independent reflectionsl = 5455
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.063 w = 1/[σ2(Fo2) + (0.0439P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.148(Δ/σ)max = 0.017
S = 0.87Δρmax = 0.28 e Å3
7091 reflectionsΔρmin = 0.30 e Å3
488 parameters
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.8514 (3)0.0200 (7)0.05237 (9)0.0293 (11)
H10.81240.11770.05840.035*
C20.9479 (3)0.0537 (6)0.07788 (9)0.0248 (11)
H20.93490.01230.09860.03*
C31.0350 (3)0.0780 (6)0.06434 (9)0.0270 (11)
H31.06770.19570.07950.032*
C40.9786 (3)0.1888 (7)0.03447 (9)0.0336 (12)
H4A0.95170.34230.03920.04*
H4B1.02550.20470.01810.04*
C51.1127 (3)0.1071 (6)0.05759 (9)0.0261 (11)
H51.11120.120.03420.031*
C60.9872 (4)0.2952 (7)0.08177 (10)0.0290 (11)
C71.2229 (3)0.0610 (7)0.07191 (9)0.0252 (11)
C81.2795 (3)0.2185 (7)0.09198 (10)0.0307 (12)
H81.24990.35920.09770.037*
C91.3790 (4)0.1603 (7)0.10295 (10)0.0290 (11)
C101.4253 (3)0.0382 (7)0.09466 (10)0.0304 (11)
C111.3719 (3)0.1947 (7)0.07505 (10)0.0351 (12)
H111.40320.3330.06930.042*
C121.2694 (4)0.1418 (7)0.06398 (9)0.0330 (12)
H121.22970.24810.05050.04*
C131.5341 (3)0.1361 (7)0.13167 (10)0.0394 (13)
H13A1.60160.21570.13240.047*
H13B1.52790.07490.1530.047*
C140.7752 (3)0.2158 (7)0.04596 (10)0.0262 (11)
C150.7791 (3)0.3568 (7)0.01972 (10)0.0324 (12)
H150.83190.33960.00650.039*
C160.7033 (4)0.5216 (7)0.01382 (10)0.0327 (12)
C170.6289 (4)0.5531 (7)0.03320 (11)0.0346 (12)
C180.6240 (4)0.4219 (8)0.05920 (11)0.0480 (14)
H180.57270.44660.07280.058*
C190.6980 (4)0.2492 (8)0.06489 (10)0.0421 (13)
H190.69530.15040.08250.051*
C200.6065 (4)0.8187 (8)0.00530 (11)0.0493 (14)
H20A0.63360.97540.00050.059*
H20B0.55310.82680.0240.059*
O10.8948 (2)0.0338 (4)0.02426 (6)0.0319 (8)
O21.0769 (2)0.3221 (4)0.06927 (6)0.0320 (8)
O30.9482 (2)0.4556 (5)0.09356 (6)0.0366 (8)
O41.4511 (2)0.2911 (4)0.12200 (7)0.0468 (9)
O51.5270 (2)0.0480 (5)0.10889 (7)0.0384 (8)
O60.6884 (3)0.6701 (5)0.01138 (7)0.0532 (10)
O70.5621 (2)0.7275 (5)0.02135 (8)0.0492 (9)
C211.0850 (3)0.5919 (6)0.20466 (9)0.0275 (11)
H211.12630.45510.19960.033*
C221.0928 (3)0.6116 (6)0.24158 (9)0.0253 (11)
H221.15550.52930.2520.03*
C230.9933 (3)0.4956 (6)0.24929 (9)0.0260 (11)
H231.00680.3810.26680.031*
C240.9494 (3)0.3854 (7)0.21798 (10)0.0375 (12)
H24A0.98080.23260.21550.045*
H24B0.87320.36840.21640.045*
C250.9258 (3)0.6974 (6)0.25787 (9)0.0253 (11)
H250.87380.73130.23910.03*
C261.0886 (4)0.8511 (7)0.25394 (9)0.0273 (11)
C270.8680 (3)0.6654 (7)0.28589 (10)0.0234 (10)
C280.8106 (3)0.4663 (7)0.28816 (9)0.0300 (11)
H280.81210.35050.27260.036*
C290.7503 (3)0.4306 (7)0.31281 (9)0.0290 (11)
H290.7110.29440.31430.035*
C300.7516 (3)0.6023 (7)0.33448 (10)0.0247 (11)
C310.8076 (3)0.7996 (7)0.33240 (10)0.0254 (11)
C320.8674 (3)0.8377 (6)0.30857 (10)0.0268 (11)
H320.90630.97490.30760.032*
C330.7182 (4)0.8357 (8)0.37286 (12)0.0713 (19)
H33A0.74070.83120.39590.086*
H33B0.65280.92450.36910.086*
C341.1210 (4)0.7956 (6)0.18704 (9)0.0261 (11)
C351.2267 (3)0.8437 (6)0.19155 (9)0.0271 (11)
H351.27390.75030.20480.033*
C361.2602 (4)1.0304 (7)0.17627 (10)0.0286 (11)
C371.1919 (4)1.1658 (7)0.15673 (10)0.0310 (12)
C381.0889 (4)1.1223 (7)0.15196 (9)0.0341 (12)
H381.04251.21660.13860.041*
C391.0535 (3)0.9324 (7)0.16757 (9)0.0310 (11)
H390.98150.89690.16470.037*
C401.3511 (4)1.3264 (7)0.16035 (10)0.0411 (13)
H40A1.40221.33520.14510.049*
H40B1.3641.45550.17540.049*
O80.9774 (2)0.5428 (4)0.19476 (6)0.0346 (8)
O90.9945 (2)0.8947 (4)0.26320 (6)0.0322 (8)
O101.1542 (2)0.9978 (5)0.25638 (6)0.0413 (9)
O110.7013 (2)0.6093 (4)0.36117 (6)0.0338 (8)
O120.7957 (2)0.9437 (4)0.35731 (6)0.0376 (8)
O131.3609 (2)1.1101 (5)0.17700 (7)0.0410 (9)
O141.2472 (3)1.3389 (5)0.14405 (7)0.0420 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.029 (3)0.037 (3)0.024 (3)0.003 (2)0.009 (2)0.001 (2)
C20.031 (3)0.022 (2)0.020 (3)0.004 (2)0.002 (2)0.003 (2)
C30.031 (3)0.024 (3)0.025 (3)0.002 (2)0.001 (2)0.004 (2)
C40.034 (3)0.031 (3)0.036 (3)0.007 (2)0.003 (2)0.003 (2)
C50.030 (3)0.023 (3)0.026 (3)0.000 (2)0.003 (2)0.004 (2)
C60.026 (3)0.034 (3)0.026 (3)0.010 (3)0.001 (2)0.004 (2)
C70.021 (3)0.026 (3)0.028 (3)0.002 (2)0.003 (2)0.001 (2)
C80.027 (3)0.024 (3)0.041 (3)0.002 (2)0.002 (2)0.003 (2)
C90.030 (3)0.022 (3)0.033 (3)0.000 (3)0.000 (2)0.003 (2)
C100.020 (3)0.037 (3)0.034 (3)0.000 (3)0.002 (2)0.002 (2)
C110.030 (3)0.032 (3)0.042 (3)0.010 (2)0.000 (3)0.004 (2)
C120.035 (3)0.034 (3)0.028 (3)0.003 (3)0.001 (2)0.006 (2)
C130.032 (3)0.039 (3)0.044 (3)0.002 (3)0.008 (3)0.004 (3)
C140.021 (3)0.032 (3)0.025 (3)0.001 (2)0.001 (2)0.003 (2)
C150.028 (3)0.037 (3)0.032 (3)0.001 (2)0.006 (2)0.001 (2)
C160.035 (3)0.035 (3)0.028 (3)0.002 (3)0.003 (2)0.006 (2)
C170.031 (3)0.036 (3)0.036 (3)0.014 (3)0.003 (3)0.004 (3)
C180.037 (4)0.064 (4)0.045 (4)0.022 (3)0.013 (3)0.007 (3)
C190.042 (4)0.055 (3)0.029 (3)0.007 (3)0.006 (3)0.005 (2)
C200.044 (4)0.044 (3)0.058 (4)0.009 (3)0.001 (3)0.006 (3)
O10.032 (2)0.0372 (18)0.0263 (18)0.0066 (15)0.0045 (15)0.0017 (14)
O20.025 (2)0.0249 (17)0.046 (2)0.0014 (15)0.0070 (16)0.0006 (15)
O30.037 (2)0.0343 (19)0.040 (2)0.0057 (16)0.0080 (16)0.0059 (15)
O40.040 (2)0.0328 (19)0.062 (2)0.0040 (17)0.0166 (19)0.0103 (17)
O50.027 (2)0.0399 (19)0.046 (2)0.0027 (16)0.0035 (17)0.0018 (16)
O60.058 (3)0.052 (2)0.052 (2)0.0219 (19)0.0143 (19)0.0237 (18)
O70.044 (2)0.049 (2)0.056 (2)0.0150 (18)0.0081 (19)0.0080 (17)
C210.021 (3)0.031 (3)0.031 (3)0.004 (2)0.004 (2)0.007 (2)
C220.023 (3)0.034 (3)0.019 (3)0.004 (2)0.001 (2)0.001 (2)
C230.024 (3)0.022 (2)0.033 (3)0.001 (2)0.006 (2)0.000 (2)
C240.043 (3)0.031 (3)0.038 (3)0.006 (2)0.007 (3)0.003 (2)
C250.025 (3)0.023 (3)0.027 (3)0.006 (2)0.000 (2)0.000 (2)
C260.028 (3)0.033 (3)0.023 (3)0.008 (3)0.010 (2)0.003 (2)
C270.018 (3)0.021 (2)0.031 (3)0.001 (2)0.002 (2)0.005 (2)
C280.034 (3)0.029 (3)0.027 (3)0.001 (2)0.004 (2)0.003 (2)
C290.030 (3)0.026 (3)0.031 (3)0.006 (2)0.002 (2)0.005 (2)
C300.024 (3)0.021 (3)0.030 (3)0.001 (2)0.008 (2)0.002 (2)
C310.025 (3)0.022 (3)0.030 (3)0.001 (2)0.005 (2)0.006 (2)
C320.024 (3)0.022 (2)0.035 (3)0.005 (2)0.007 (2)0.003 (2)
C330.095 (5)0.047 (4)0.084 (4)0.032 (3)0.058 (4)0.025 (3)
C340.030 (3)0.026 (3)0.023 (3)0.003 (2)0.006 (2)0.005 (2)
C350.030 (3)0.023 (3)0.028 (3)0.008 (2)0.003 (2)0.001 (2)
C360.031 (3)0.028 (3)0.028 (3)0.007 (3)0.008 (2)0.002 (2)
C370.045 (4)0.023 (3)0.027 (3)0.006 (3)0.013 (3)0.001 (2)
C380.037 (4)0.039 (3)0.024 (3)0.003 (3)0.003 (2)0.001 (2)
C390.029 (3)0.034 (3)0.030 (3)0.005 (2)0.005 (2)0.009 (2)
C400.057 (4)0.029 (3)0.040 (3)0.009 (3)0.017 (3)0.000 (2)
O80.037 (2)0.0395 (18)0.0270 (18)0.0030 (16)0.0026 (16)0.0005 (15)
O90.035 (2)0.0247 (17)0.0400 (19)0.0064 (15)0.0177 (16)0.0021 (14)
O100.044 (2)0.044 (2)0.038 (2)0.0217 (18)0.0156 (17)0.0155 (15)
O110.037 (2)0.0370 (19)0.0298 (19)0.0086 (15)0.0135 (16)0.0035 (15)
O120.047 (2)0.0341 (18)0.036 (2)0.0079 (16)0.0203 (17)0.0083 (15)
O130.034 (2)0.0347 (19)0.057 (2)0.0005 (16)0.0168 (17)0.0136 (16)
O140.046 (2)0.041 (2)0.038 (2)0.0026 (18)0.0028 (18)0.0085 (16)
Geometric parameters (Å, º) top
C1—O11.425 (4)C21—O81.436 (4)
C1—C141.512 (5)C21—C341.511 (5)
C1—C21.563 (5)C21—C221.571 (5)
C1—H11.0000C21—H211.0000
C2—C61.498 (5)C22—C261.495 (5)
C2—C31.541 (5)C22—C231.532 (5)
C2—H21.0000C22—H221.0000
C3—C51.529 (5)C23—C241.526 (5)
C3—C41.529 (5)C23—C251.538 (5)
C3—H31.0000C23—H231.0000
C4—O11.438 (4)C24—O81.431 (4)
C4—H4A0.9900C24—H24A0.9900
C4—H4B0.9900C24—H24B0.9900
C5—O21.447 (4)C25—O91.455 (4)
C5—C71.507 (5)C25—C271.504 (5)
C5—H51.0000C25—H251.0000
C6—O31.204 (4)C26—O101.201 (4)
C6—O21.352 (5)C26—O91.358 (4)
C7—C121.388 (5)C27—C281.389 (5)
C7—C81.398 (5)C27—C321.395 (5)
C8—C91.360 (5)C28—C291.406 (5)
C8—H80.9500C28—H280.9500
C9—C101.371 (5)C29—C301.361 (5)
C9—O41.387 (4)C29—H290.9500
C10—C111.365 (5)C30—C311.369 (5)
C10—O51.383 (5)C30—O111.385 (4)
C11—C121.389 (5)C31—O121.379 (4)
C11—H110.9500C31—C321.375 (5)
C12—H120.9500C32—H320.9500
C13—O41.426 (4)C33—O111.417 (4)
C13—O51.443 (4)C33—O121.423 (5)
C13—H13A0.9900C33—H33A0.9900
C13—H13B0.9900C33—H33B0.9900
C14—C191.381 (5)C34—C391.381 (5)
C14—C151.395 (5)C34—C351.391 (5)
C15—C161.375 (5)C35—C361.368 (5)
C15—H150.9500C35—H350.9500
C16—C171.363 (5)C36—O131.386 (5)
C16—O61.374 (4)C36—C371.383 (5)
C17—C181.356 (5)C37—C381.352 (5)
C17—O71.389 (5)C37—O141.388 (4)
C18—C191.391 (5)C38—C391.400 (5)
C18—H180.9500C38—H380.9500
C19—H190.9500C39—H390.9500
C20—O61.422 (5)C40—O131.444 (4)
C20—O71.442 (5)C40—O141.439 (5)
C20—H20A0.9900C40—H40A0.9900
C20—H20B0.9900C40—H40B0.9900
O1—C1—C14109.5 (3)O8—C21—C34111.2 (3)
O1—C1—C2104.2 (3)O8—C21—C22104.1 (3)
C14—C1—C2118.6 (3)C34—C21—C22117.3 (3)
O1—C1—H1108.0O8—C21—H21107.9
C14—C1—H1108.0C34—C21—H21107.9
C2—C1—H1108.0C22—C21—H21107.9
C6—C2—C3104.6 (3)C26—C22—C23105.4 (3)
C6—C2—C1115.2 (3)C26—C22—C21115.0 (3)
C3—C2—C1103.8 (3)C23—C22—C21103.7 (3)
C6—C2—H2110.9C26—C22—H22110.8
C3—C2—H2110.9C23—C22—H22110.8
C1—C2—H2110.9C21—C22—H22110.8
C5—C3—C4113.4 (3)C24—C23—C22103.1 (3)
C5—C3—C2104.8 (3)C24—C23—C25111.7 (3)
C4—C3—C2103.1 (3)C22—C23—C25103.7 (3)
C5—C3—H3111.7C24—C23—H23112.5
C4—C3—H3111.7C22—C23—H23112.5
C2—C3—H3111.7C25—C23—H23112.5
O1—C4—C3104.5 (3)O8—C24—C23103.8 (3)
O1—C4—H4A110.8O8—C24—H24A111.0
C3—C4—H4A110.8C23—C24—H24A111.0
O1—C4—H4B110.8O8—C24—H24B111.0
C3—C4—H4B110.8C23—C24—H24B111.0
H4A—C4—H4B108.9H24A—C24—H24B109.0
O2—C5—C7110.2 (3)O9—C25—C27109.4 (3)
O2—C5—C3107.2 (3)O9—C25—C23106.5 (3)
C7—C5—C3114.5 (3)C27—C25—C23117.0 (3)
O2—C5—H5108.3O9—C25—H25107.9
C7—C5—H5108.3C27—C25—H25107.9
C3—C5—H5108.3C23—C25—H25107.9
O3—C6—O2120.4 (4)O10—C26—O9119.8 (4)
O3—C6—C2128.2 (4)O10—C26—C22129.5 (4)
O2—C6—C2111.4 (4)O9—C26—C22110.6 (4)
C12—C7—C8119.8 (4)C28—C27—C32120.0 (4)
C12—C7—C5118.3 (4)C28—C27—C25119.1 (4)
C8—C7—C5121.9 (4)C32—C27—C25120.8 (3)
C9—C8—C7116.7 (4)C27—C28—C29122.1 (4)
C9—C8—H8121.7C27—C28—H28118.9
C7—C8—H8121.7C29—C28—H28118.9
C8—C9—C10123.4 (4)C30—C29—C28116.2 (4)
C8—C9—O4127.3 (4)C30—C29—H29121.9
C10—C9—O4109.2 (4)C28—C29—H29121.9
C11—C10—C9121.0 (4)C29—C30—C31122.1 (4)
C11—C10—O5128.6 (4)C29—C30—O11128.0 (4)
C9—C10—O5110.4 (4)C31—C30—O11109.9 (3)
C10—C11—C12116.8 (4)C30—C31—O12110.3 (4)
C10—C11—H11121.6C30—C31—C32122.6 (4)
C12—C11—H11121.6O12—C31—C32127.0 (4)
C7—C12—C11122.3 (4)C31—C32—C27116.9 (4)
C7—C12—H12118.9C31—C32—H32121.6
C11—C12—H12118.9C27—C32—H32121.6
O4—C13—O5107.2 (3)O11—C33—O12109.5 (3)
O4—C13—H13A110.3O11—C33—H33A109.8
O5—C13—H13A110.3O12—C33—H33A109.8
O4—C13—H13B110.3O11—C33—H33B109.8
O5—C13—H13B110.3O12—C33—H33B109.8
H13A—C13—H13B108.5H33A—C33—H33B108.2
C19—C14—C15119.4 (4)C39—C34—C35120.4 (4)
C19—C14—C1120.6 (4)C39—C34—C21122.6 (4)
C15—C14—C1119.9 (4)C35—C34—C21117.0 (4)
C16—C15—C14117.3 (4)C36—C35—C34117.6 (4)
C16—C15—H15121.3C36—C35—H35121.2
C14—C15—H15121.3C34—C35—H35121.2
C17—C16—O6110.6 (4)C35—C36—O13127.9 (4)
C17—C16—C15122.0 (4)C35—C36—C37121.5 (4)
O6—C16—C15127.4 (4)O13—C36—C37110.6 (4)
C18—C17—C16122.2 (4)C38—C37—C36121.9 (4)
C18—C17—O7128.1 (4)C38—C37—O14129.0 (4)
C16—C17—O7109.7 (4)C36—C37—O14109.0 (4)
C17—C18—C19116.5 (4)C37—C38—C39117.2 (4)
C17—C18—H18121.8C37—C38—H38121.4
C19—C18—H18121.8C39—C38—H38121.4
C14—C19—C18122.5 (4)C34—C39—C38121.4 (4)
C14—C19—H19118.7C34—C39—H39119.3
C18—C19—H19118.7C38—C39—H39119.3
O6—C20—O7107.8 (3)O13—C40—O14107.4 (3)
O6—C20—H20A110.1O13—C40—H40A110.2
O7—C20—H20A110.1O14—C40—H40A110.2
O6—C20—H20B110.1O13—C40—H40B110.2
O7—C20—H20B110.1O14—C40—H40B110.2
H20A—C20—H20B108.5H40A—C40—H40B108.5
C1—O1—C4104.4 (3)C24—O8—C21104.4 (3)
C6—O2—C5111.6 (3)C26—O9—C25111.3 (3)
C9—O4—C13104.5 (3)C30—O11—C33104.4 (3)
C10—O5—C13103.9 (3)C31—O12—C33104.3 (3)
C16—O6—C20105.8 (3)C36—O13—C40105.0 (3)
C17—O7—C20105.1 (3)C37—O14—C40106.0 (3)
 

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