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

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680302227X/bt6364sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680302227X/bt6364Isup2.hkl
Contains datablock I

CCDC reference: 226969

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.051
  • wR factor = 0.142
  • Data-to-parameter ratio = 7.5

checkCIF/PLATON results

No syntax errors found



Alert level C REFNR01_ALERT_3_C Ratio of reflections to parameters is < 8 for a non-centrosymmetric structure, where ZMAX < 18 sine(theta)/lambda -0.1583 Proportion of unique data used 1.0000 Ratio reflections to parameters 7.4864 PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.49 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT411_ALERT_2_C Short Inter H...H Contact H4A .. H8A = 2.15 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.02 From the CIF: _reflns_number_total 1647 Count of symmetry unique reflns 1656 Completeness (_total/calc) 99.46% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 1997-2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXTL (Sheldrick, 2001); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Ethyl 7-exo-acetoxy-4-phenyltricyclo[4.2.1.02,5]non-3-ene-3-carboxylate top
Crystal data top
C20H22O4F(000) = 348
Mr = 326.38Dx = 1.295 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 18043 reflections
a = 9.7510 (14) Åθ = 2.6–25.0°
b = 5.5920 (9) ŵ = 0.09 mm1
c = 15.3550 (18) ÅT = 150 K
β = 90.934 (10)°Needle, colourless
V = 837.2 (2) Å30.14 × 0.10 × 0.05 mm
Z = 2
Data collection top
Nonius KappaCCD
diffractometer
1182 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.080
Graphite monochromatorθmax = 25.0°, θmin = 2.7°
Detector resolution: 9 pixels mm-1h = 1111
φ scans and ω scans with κ offsetsk = 66
5502 measured reflectionsl = 1818
1647 independent reflections
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)] = 0.051H-atom parameters constrained
wR(F2) = 0.142 w = 1/[σ2(Fo2) + (0.0749P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
1647 reflectionsΔρmax = 0.16 e Å3
220 parametersΔρmin = 0.16 e Å3
1 restraintExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.058 (11)
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
O10.2054 (3)0.0946 (6)0.52829 (18)0.0518 (9)
O20.0894 (4)0.3291 (8)0.6200 (2)0.0663 (11)
O30.4800 (3)0.4212 (7)0.08568 (19)0.0570 (9)
O40.5212 (3)0.6833 (6)0.19453 (18)0.0515 (9)
C10.1869 (5)0.2697 (9)0.4574 (2)0.0461 (11)
H1A0.09170.33630.45470.055*
C20.2974 (5)0.4680 (10)0.4639 (3)0.0538 (13)
H2A0.25530.62890.46020.065*
H2B0.35090.45520.51900.065*
C30.3884 (5)0.4185 (10)0.3843 (3)0.0507 (12)
H3A0.48340.48520.38880.061*
C40.3056 (4)0.5000 (9)0.3052 (3)0.0472 (11)
H4A0.27270.66930.30740.057*
C50.3438 (5)0.4104 (9)0.2149 (3)0.0455 (11)
C60.2449 (4)0.2432 (9)0.2100 (3)0.0451 (12)
C70.1891 (5)0.3056 (10)0.2990 (3)0.0484 (12)
H7A0.09350.37040.29830.058*
C80.2235 (5)0.1373 (9)0.3750 (3)0.0443 (11)
H8A0.18290.02630.36960.053*
C90.3802 (5)0.1434 (10)0.3793 (3)0.0498 (12)
H9A0.42280.07780.32640.060*
H9B0.41840.06390.43200.060*
C100.2001 (4)0.0518 (9)0.1509 (3)0.0447 (12)
C110.0861 (4)0.0836 (10)0.1735 (3)0.0497 (12)
H11A0.03780.04700.22500.060*
C120.0430 (5)0.2720 (11)0.1208 (3)0.0574 (14)
H12A0.03510.36320.13620.069*
C130.1140 (5)0.3277 (10)0.0454 (3)0.0557 (13)
H13A0.08500.45690.00940.067*
C140.2261 (5)0.1934 (10)0.0239 (3)0.0552 (13)
H14A0.27510.23210.02720.066*
C150.2694 (5)0.0031 (9)0.0747 (3)0.0493 (12)
H15A0.34600.08990.05780.059*
C160.1536 (5)0.1475 (10)0.6058 (3)0.0493 (13)
C170.1899 (5)0.0409 (11)0.6710 (3)0.0599 (14)
H17A0.13280.02210.72240.090*
H17B0.28680.02540.68800.090*
H17C0.17400.19910.64520.090*
C180.4520 (4)0.4990 (9)0.1569 (3)0.0450 (11)
C190.6270 (5)0.7913 (10)0.1412 (3)0.0549 (13)
H19A0.58650.85480.08630.066*
H19B0.69780.67170.12660.066*
C200.6887 (5)0.9907 (10)0.1947 (3)0.0562 (13)
H20A0.75641.07660.16000.084*
H20B0.73370.92390.24680.084*
H20C0.61631.10140.21210.084*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0615 (19)0.052 (2)0.0420 (17)0.0052 (17)0.0078 (15)0.0001 (15)
O20.075 (2)0.073 (3)0.051 (2)0.020 (2)0.0116 (17)0.0058 (18)
O30.066 (2)0.059 (2)0.0466 (18)0.0018 (18)0.0121 (15)0.0082 (17)
O40.0585 (18)0.054 (2)0.0427 (16)0.0099 (17)0.0090 (14)0.0013 (16)
C10.056 (3)0.047 (3)0.035 (2)0.001 (2)0.0064 (18)0.003 (2)
C20.072 (3)0.050 (3)0.039 (2)0.002 (3)0.005 (2)0.009 (2)
C30.051 (3)0.057 (3)0.044 (3)0.005 (2)0.010 (2)0.002 (2)
C40.058 (3)0.040 (3)0.044 (2)0.002 (2)0.011 (2)0.001 (2)
C50.054 (3)0.042 (3)0.040 (2)0.007 (2)0.006 (2)0.000 (2)
C60.043 (2)0.054 (3)0.039 (2)0.006 (2)0.0055 (19)0.007 (2)
C70.051 (3)0.050 (3)0.044 (2)0.002 (2)0.0083 (19)0.004 (2)
C80.053 (2)0.042 (3)0.038 (2)0.001 (2)0.0055 (18)0.003 (2)
C90.049 (3)0.053 (3)0.048 (3)0.003 (2)0.001 (2)0.002 (2)
C100.044 (2)0.050 (3)0.040 (2)0.003 (2)0.0033 (19)0.002 (2)
C110.052 (3)0.056 (3)0.041 (2)0.000 (3)0.002 (2)0.001 (2)
C120.051 (3)0.065 (4)0.056 (3)0.004 (3)0.003 (2)0.003 (3)
C130.067 (3)0.053 (3)0.048 (3)0.001 (3)0.003 (2)0.000 (2)
C140.065 (3)0.061 (4)0.040 (2)0.004 (3)0.009 (2)0.002 (3)
C150.058 (3)0.049 (3)0.041 (2)0.002 (3)0.005 (2)0.002 (2)
C160.048 (3)0.059 (4)0.041 (3)0.009 (3)0.005 (2)0.004 (2)
C170.062 (3)0.071 (4)0.047 (3)0.007 (3)0.005 (2)0.004 (3)
C180.052 (2)0.042 (3)0.041 (2)0.006 (2)0.003 (2)0.003 (2)
C190.058 (3)0.057 (3)0.051 (3)0.008 (3)0.007 (2)0.005 (3)
C200.060 (3)0.053 (3)0.056 (3)0.004 (3)0.003 (2)0.007 (3)
Geometric parameters (Å, º) top
O1—C161.334 (5)C8—H8A1.0000
O1—C11.473 (5)C9—H9A0.9900
O2—C161.215 (6)C9—H9B0.9900
O3—C181.212 (5)C10—C111.393 (6)
O4—C181.356 (6)C10—C151.395 (6)
O4—C191.459 (5)C11—C121.390 (7)
C1—C81.513 (6)C11—H11A0.9500
C1—C21.548 (7)C12—C131.394 (6)
C1—H1A1.0000C12—H12A0.9500
C2—C31.546 (6)C13—C141.371 (7)
C2—H2A0.9900C13—H13A0.9500
C2—H2B0.9900C14—C151.382 (7)
C3—C41.517 (7)C14—H14A0.9500
C3—C91.543 (8)C15—H15A0.9500
C3—H3A1.0000C16—C171.491 (7)
C4—C51.527 (6)C17—H17A0.9800
C4—C71.574 (7)C17—H17B0.9800
C4—H4A1.0000C17—H17C0.9800
C5—C61.345 (7)C19—C201.505 (7)
C5—C181.477 (6)C19—H19A0.9900
C6—C101.466 (6)C19—H19B0.9900
C6—C71.519 (6)C20—H20A0.9800
C7—C81.532 (7)C20—H20B0.9800
C7—H7A1.0000C20—H20C0.9800
C8—C91.529 (6)
C16—O1—C1118.0 (4)C3—C9—H9A112.9
C18—O4—C19115.3 (3)C8—C9—H9B112.9
O1—C1—C8105.4 (4)C3—C9—H9B112.9
O1—C1—C2110.6 (3)H9A—C9—H9B110.3
C8—C1—C2103.4 (3)C11—C10—C15119.3 (4)
O1—C1—H1A112.3C11—C10—C6118.3 (4)
C8—C1—H1A112.3C15—C10—C6122.5 (4)
C2—C1—H1A112.3C12—C11—C10120.1 (4)
C3—C2—C1103.2 (4)C12—C11—H11A119.9
C3—C2—H2A111.1C10—C11—H11A119.9
C1—C2—H2A111.1C11—C12—C13120.3 (5)
C3—C2—H2B111.1C11—C12—H12A119.9
C1—C2—H2B111.1C13—C12—H12A119.9
H2A—C2—H2B109.1C14—C13—C12119.1 (5)
C4—C3—C9103.5 (4)C14—C13—H13A120.5
C4—C3—C2105.9 (4)C12—C13—H13A120.5
C9—C3—C2100.8 (4)C13—C14—C15121.6 (4)
C4—C3—H3A115.0C13—C14—H14A119.2
C9—C3—H3A115.0C15—C14—H14A119.2
C2—C3—H3A115.0C14—C15—C10119.7 (4)
C3—C4—C5119.6 (4)C14—C15—H15A120.2
C3—C4—C7102.5 (4)C10—C15—H15A120.2
C5—C4—C784.5 (3)O2—C16—O1123.3 (5)
C3—C4—H4A115.1O2—C16—C17126.1 (4)
C5—C4—H4A115.1O1—C16—C17110.6 (5)
C7—C4—H4A115.1C16—C17—H17A109.5
C6—C5—C18136.0 (4)C16—C17—H17B109.5
C6—C5—C495.3 (4)H17A—C17—H17B109.5
C18—C5—C4128.7 (4)C16—C17—H17C109.5
C5—C6—C10138.4 (4)H17A—C17—H17C109.5
C5—C6—C793.3 (4)H17B—C17—H17C109.5
C10—C6—C7128.1 (4)O3—C18—O4122.7 (4)
C6—C7—C8117.8 (4)O3—C18—C5126.6 (5)
C6—C7—C486.8 (3)O4—C18—C5110.7 (4)
C8—C7—C4103.2 (4)O4—C19—C20106.3 (4)
C6—C7—H7A115.0O4—C19—H19A110.5
C8—C7—H7A115.0C20—C19—H19A110.5
C4—C7—H7A115.0O4—C19—H19B110.5
C1—C8—C9101.6 (4)C20—C19—H19B110.5
C1—C8—C7106.5 (4)H19A—C19—H19B108.7
C9—C8—C7103.0 (4)C19—C20—H20A109.5
C1—C8—H8A114.7C19—C20—H20B109.5
C9—C8—H8A114.7H20A—C20—H20B109.5
C7—C8—H8A114.7C19—C20—H20C109.5
C8—C9—C394.3 (4)H20A—C20—H20C109.5
C8—C9—H9A112.9H20B—C20—H20C109.5
 

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