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The regio- and stereochemistry of the title compound, C20H22O4, has been established by X-ray analysis. The molecular dimensions are normal.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802008279/ac6004sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802008279/ac6004Isup2.hkl
Contains datablock I

CCDC reference: 189377

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.043
  • wR factor = 0.120
  • Data-to-parameter ratio = 17.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1992); cell refinement: CAD-4 Software; data reduction: HELENA/PLATON/System S (Spek, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON; software used to prepare material for publication: SHELXL97.

3-Ethoxy-7-methoxycarbonyl-4-phenyl-tricyclco-[4,2,1,0-(2,5)]non-3-ene top
Crystal data top
C20H22O4F(000) = 696
Mr = 326.38Dx = 1.268 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 12.842 (8) Åθ = 9.4–12.1°
b = 9.831 (8) ŵ = 0.09 mm1
c = 18.063 (6) ÅT = 298 K
β = 131.44 (2)°Block, colourless
V = 1709.5 (18) Å30.4 × 0.3 × 0.2 mm
Z = 4
Data collection top
Nonius CAD-4
diffractometer
Rint = 0.010
Radiation source: fine-focus sealed tubeθmax = 27.5°, θmin = 2.1°
Graphite monochromatorh = 1616
θ/2θ scansk = 120
4180 measured reflectionsl = 2315
3909 independent reflections3 standard reflections every 120 min
2433 reflections with I > 2σ(I) intensity decay: 0.01%
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)] = 0.043H-atom parameters constrained
wR(F2) = 0.121 w = 1/[σ2(Fo2) + (0.0662P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
3909 reflectionsΔρmax = 0.22 e Å3
220 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0112 (16)
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*/UeqOcc. (<1)
O310.38860 (13)0.30037 (13)0.00282 (9)0.0597 (4)
O320.42813 (11)0.36323 (11)0.09575 (8)0.0463 (3)
O710.83547 (16)0.11084 (15)0.04700 (9)0.0749 (4)
O720.96014 (13)0.16346 (13)0.11115 (8)0.0599 (4)
C10.76692 (17)0.25934 (17)0.01589 (12)0.0461 (4)
H10.73970.35200.01060.055*
C20.64733 (16)0.16683 (15)0.01637 (11)0.0382 (3)
H20.58880.13330.08440.046*
C30.57110 (15)0.19694 (15)0.01884 (11)0.0381 (4)
C310.45516 (16)0.28975 (16)0.02205 (11)0.0399 (4)
C320.30952 (18)0.45344 (18)0.14744 (12)0.0503 (4)
H32A0.31890.51460.10120.060*
H32B0.22470.40130.18130.060*
C330.3050 (2)0.53234 (18)0.22011 (13)0.0559 (5)
H33A0.39080.58080.18600.084*
H33B0.22930.59590.25400.084*
H33C0.29190.47110.26710.084*
C40.63964 (15)0.10217 (15)0.09128 (11)0.0365 (3)
C410.64387 (16)0.05233 (16)0.16977 (11)0.0389 (4)
C420.56822 (18)0.11210 (17)0.19144 (12)0.0481 (4)
H420.51280.18760.15580.058*
C430.5753 (2)0.0597 (2)0.26539 (14)0.0611 (5)
H430.52550.10090.28000.073*
C440.6555 (2)0.0535 (2)0.31796 (14)0.0659 (6)
H440.65880.08900.36720.079*
C450.7306 (2)0.1138 (2)0.29728 (13)0.0617 (5)
H450.78480.19010.33260.074*
C460.72521 (18)0.06079 (17)0.22407 (12)0.0490 (4)
H460.77680.10140.21080.059*
C50.72413 (15)0.05285 (16)0.06538 (10)0.0371 (3)
H50.70410.04050.04010.044*
C60.87701 (16)0.09422 (16)0.13224 (11)0.0419 (4)
H60.93750.05470.19870.050*
C70.92288 (17)0.06771 (18)0.07299 (12)0.0481 (4)
H71.02270.08640.11650.058*
C710.89890 (17)0.07534 (19)0.03632 (12)0.0483 (4)
C720.9466 (2)0.3061 (2)0.08849 (15)0.0662 (5)
H72A1.01790.35590.14750.099*0.50
H72B0.95580.32020.04040.099*0.50
H72C0.85710.33760.06240.099*0.50
H72D0.86930.31990.01940.099*0.50
H72E0.93140.35550.12650.099*0.50
H72F1.03010.33820.10450.099*0.50
C80.84496 (19)0.17986 (19)0.00774 (14)0.0566 (5)
H8A0.90970.23820.00350.068*
H8B0.78080.14020.07330.068*
C90.86919 (17)0.24955 (17)0.12869 (12)0.0484 (4)
H9A0.95790.29190.15960.058*
H9B0.83140.28570.15660.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O310.0542 (7)0.0735 (9)0.0679 (8)0.0183 (6)0.0474 (7)0.0180 (7)
O320.0434 (6)0.0492 (7)0.0466 (6)0.0120 (5)0.0298 (5)0.0108 (5)
O710.0953 (11)0.0810 (10)0.0482 (7)0.0164 (8)0.0475 (8)0.0001 (7)
O720.0612 (8)0.0631 (8)0.0470 (7)0.0083 (6)0.0322 (6)0.0055 (6)
C10.0478 (10)0.0452 (9)0.0533 (9)0.0011 (8)0.0368 (9)0.0059 (8)
C20.0369 (8)0.0425 (8)0.0350 (7)0.0017 (7)0.0237 (7)0.0020 (7)
C30.0351 (8)0.0397 (8)0.0384 (8)0.0012 (7)0.0239 (7)0.0007 (7)
C310.0357 (8)0.0408 (8)0.0406 (8)0.0014 (7)0.0242 (7)0.0009 (7)
C320.0431 (9)0.0527 (10)0.0476 (9)0.0134 (8)0.0268 (8)0.0067 (8)
C330.0525 (11)0.0557 (11)0.0471 (9)0.0101 (9)0.0277 (9)0.0093 (8)
C40.0346 (8)0.0380 (8)0.0384 (8)0.0028 (7)0.0248 (7)0.0027 (7)
C410.0389 (8)0.0416 (8)0.0368 (8)0.0049 (7)0.0253 (7)0.0015 (6)
C420.0558 (10)0.0482 (10)0.0534 (10)0.0018 (8)0.0418 (9)0.0002 (8)
C430.0708 (13)0.0738 (13)0.0613 (11)0.0069 (11)0.0533 (11)0.0035 (10)
C440.0771 (14)0.0785 (14)0.0522 (11)0.0073 (12)0.0470 (11)0.0076 (10)
C450.0682 (13)0.0604 (12)0.0511 (10)0.0050 (10)0.0372 (10)0.0140 (9)
C460.0522 (10)0.0509 (10)0.0468 (9)0.0027 (8)0.0341 (9)0.0037 (8)
C50.0388 (8)0.0398 (8)0.0359 (8)0.0013 (7)0.0261 (7)0.0008 (6)
C60.0363 (8)0.0533 (10)0.0359 (8)0.0045 (7)0.0238 (7)0.0004 (7)
C70.0388 (9)0.0645 (11)0.0473 (9)0.0028 (8)0.0312 (8)0.0015 (8)
C710.0425 (9)0.0668 (11)0.0468 (10)0.0099 (8)0.0342 (8)0.0048 (9)
C720.0756 (14)0.0605 (12)0.0713 (13)0.0100 (10)0.0524 (12)0.0068 (10)
C80.0574 (11)0.0675 (12)0.0641 (11)0.0055 (10)0.0484 (10)0.0124 (9)
C90.0379 (9)0.0526 (10)0.0510 (10)0.0076 (8)0.0279 (8)0.0071 (8)
Geometric parameters (Å, º) top
O31—C311.2048 (19)C42—H420.9300
O32—C311.3428 (19)C43—C441.381 (3)
O32—C321.448 (2)C43—H430.9300
O71—C711.195 (2)C44—C451.378 (3)
O72—C711.338 (2)C44—H440.9300
O72—C721.439 (2)C45—C461.380 (2)
C1—C21.530 (2)C45—H450.9300
C1—C91.531 (2)C46—H460.9300
C1—C81.537 (2)C5—C61.530 (2)
C1—H10.9800C5—H50.9800
C2—C31.508 (2)C6—C91.529 (3)
C2—C51.575 (2)C6—C71.547 (2)
C2—H20.9800C6—H60.9800
C3—C41.353 (2)C7—C711.497 (3)
C3—C311.463 (2)C7—C81.553 (3)
C32—C331.492 (2)C7—H70.9800
C32—H32A0.9700C72—H72A0.9600
C32—H32B0.9700C72—H72B0.9600
C33—H33A0.9600C72—H72C0.9600
C33—H33B0.9600C72—H72D0.9600
C33—H33C0.9600C72—H72E0.9600
C4—C411.467 (2)C72—H72F0.9600
C4—C51.517 (2)C8—H8A0.9700
C41—C461.391 (2)C8—H8B0.9700
C41—C421.395 (2)C9—H9A0.9700
C42—C431.378 (2)C9—H9B0.9700
C31—O32—C32116.12 (13)C4—C5—C285.98 (11)
C71—O72—C72117.66 (15)C6—C5—C2103.36 (12)
C2—C1—C9103.31 (12)C4—C5—H5114.9
C2—C1—C8105.47 (14)C6—C5—H5114.9
C9—C1—C8101.24 (14)C2—C5—H5114.9
C2—C1—H1115.1C9—C6—C5102.60 (13)
C9—C1—H1115.1C9—C6—C7100.59 (13)
C8—C1—H1115.1C5—C6—C7106.64 (13)
C3—C2—C1119.40 (13)C9—C6—H6115.1
C3—C2—C585.57 (11)C5—C6—H6115.1
C1—C2—C5102.59 (13)C7—C6—H6115.1
C3—C2—H2114.9C71—C7—C6113.78 (13)
C1—C2—H2114.9C71—C7—C8115.81 (15)
C5—C2—H2114.9C6—C7—C8103.07 (13)
C4—C3—C31135.34 (14)C71—C7—H7107.9
C4—C3—C294.83 (12)C6—C7—H7107.9
C31—C3—C2129.60 (13)C8—C7—H7107.9
O31—C31—O32122.78 (15)O71—C71—O72122.58 (18)
O31—C31—C3127.02 (15)O71—C71—C7126.93 (16)
O32—C31—C3110.19 (13)O72—C71—C7110.49 (14)
O32—C32—C33107.32 (15)O72—C72—H72A109.5
O32—C32—H32A110.3O72—C72—H72B109.5
C33—C32—H32A110.3H72A—C72—H72B109.5
O32—C32—H32B110.3O72—C72—H72C109.5
C33—C32—H32B110.3H72A—C72—H72C109.5
H32A—C32—H32B108.5H72B—C72—H72C109.5
C32—C33—H33A109.5O72—C72—H72D109.5
C32—C33—H33B109.5H72A—C72—H72D141.1
H33A—C33—H33B109.5H72B—C72—H72D56.3
C32—C33—H33C109.5H72C—C72—H72D56.3
H33A—C33—H33C109.5O72—C72—H72E109.5
H33B—C33—H33C109.5H72A—C72—H72E56.3
C3—C4—C41138.51 (14)H72B—C72—H72E141.1
C3—C4—C593.57 (12)H72C—C72—H72E56.3
C41—C4—C5127.93 (14)H72D—C72—H72E109.5
C46—C41—C42118.46 (14)O72—C72—H72F109.5
C46—C41—C4118.62 (14)H72A—C72—H72F56.3
C42—C41—C4122.92 (15)H72B—C72—H72F56.3
C43—C42—C41120.24 (17)H72C—C72—H72F141.1
C43—C42—H42119.9H72D—C72—H72F109.5
C41—C42—H42119.9H72E—C72—H72F109.5
C42—C43—C44120.56 (18)C1—C8—C7103.50 (13)
C42—C43—H43119.7C1—C8—H8A111.1
C44—C43—H43119.7C7—C8—H8A111.1
C45—C44—C43119.87 (17)C1—C8—H8B111.1
C45—C44—H44120.1C7—C8—H8B111.1
C43—C44—H44120.1H8A—C8—H8B109.0
C44—C45—C46119.80 (18)C6—C9—C195.35 (13)
C44—C45—H45120.1C6—C9—H9A112.7
C46—C45—H45120.1C1—C9—H9A112.7
C45—C46—C41121.06 (17)C6—C9—H9B112.7
C45—C46—H46119.5C1—C9—H9B112.7
C41—C46—H46119.5H9A—C9—H9B110.2
C4—C5—C6118.53 (13)
C9—C1—C2—C358.95 (17)C3—C4—C5—C6104.82 (15)
C8—C1—C2—C3164.80 (13)C41—C4—C5—C675.4 (2)
C9—C1—C2—C533.06 (14)C3—C4—C5—C21.79 (12)
C8—C1—C2—C572.80 (15)C41—C4—C5—C2178.41 (15)
C1—C2—C3—C4100.16 (16)C3—C2—C5—C41.61 (11)
C5—C2—C3—C41.80 (12)C1—C2—C5—C4117.55 (12)
C1—C2—C3—C3184.7 (2)C3—C2—C5—C6119.99 (12)
C5—C2—C3—C31173.30 (16)C1—C2—C5—C60.84 (14)
C32—O32—C31—O312.5 (2)C4—C5—C6—C958.28 (17)
C32—O32—C31—C3176.13 (13)C2—C5—C6—C934.43 (14)
C4—C3—C31—O311.1 (3)C4—C5—C6—C7163.54 (13)
C2—C3—C31—O31171.95 (16)C2—C5—C6—C770.84 (15)
C4—C3—C31—O32179.62 (16)C9—C6—C7—C71162.32 (14)
C2—C3—C31—O326.6 (2)C5—C6—C7—C7155.61 (17)
C31—O32—C32—C33175.65 (14)C9—C6—C7—C836.10 (16)
C31—C3—C4—C417.0 (3)C5—C6—C7—C870.60 (16)
C2—C3—C4—C41178.37 (18)C72—O72—C71—O710.6 (2)
C31—C3—C4—C5172.76 (17)C72—O72—C71—C7179.72 (15)
C2—C3—C4—C51.87 (12)C6—C7—C71—O71125.40 (19)
C3—C4—C41—C46173.96 (18)C8—C7—C71—O716.2 (3)
C5—C4—C41—C465.7 (2)C6—C7—C71—O7254.92 (18)
C3—C4—C41—C425.0 (3)C8—C7—C71—O72174.11 (13)
C5—C4—C41—C42175.27 (14)C2—C1—C8—C773.50 (16)
C46—C41—C42—C430.3 (2)C9—C1—C8—C733.87 (16)
C4—C41—C42—C43179.27 (16)C71—C7—C8—C1126.25 (15)
C41—C42—C43—C440.9 (3)C6—C7—C8—C11.35 (17)
C42—C43—C44—C450.8 (3)C5—C6—C9—C153.60 (13)
C43—C44—C45—C460.0 (3)C7—C6—C9—C156.30 (14)
C44—C45—C46—C410.6 (3)C2—C1—C9—C653.40 (14)
C42—C41—C46—C450.5 (3)C8—C1—C9—C655.65 (14)
C4—C41—C46—C45178.55 (15)
 

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