Ethyl 7-exo-acetoxy-4-phenyl­tri­cyclo­[4.2.1.0^2,5]­non-3-ene-3-carboxyl­ate

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

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

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Computing details

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[4.2.1.0^2,5]non-3-ene-3-carboxylate

Crystal data

C20H22O4	F(000) = 348
Mr = 326.38	Dx = 1.295 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 18043 reflections
a = 9.7510 (14) Å	θ = 2.6–25.0°
b = 5.5920 (9) Å	µ = 0.09 mm^−1
c = 15.3550 (18) Å	T = 150 K
β = 90.934 (10)°	Needle, colourless
V = 837.2 (2) Å^3	0.14 × 0.10 × 0.05 mm
Z = 2

Data collection

Nonius KappaCCD diffractometer	1182 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.080
Graphite monochromator	θmax = 25.0°, θmin = 2.7°
Detector resolution: 9 pixels mm^-1	h = −11→11
φ scans and ω scans with κ offsets	k = −6→6
5502 measured reflections	l = −18→18
1647 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.142	w = 1/[σ^2(Fo^2) + (0.0749P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
1647 reflections	Δρmax = 0.16 e Å^−3
220 parameters	Δρmin = −0.16 e Å^−3
1 restraint	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.058 (11)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.2054 (3)	0.0946 (6)	0.52829 (18)	0.0518 (9)
O2	0.0894 (4)	0.3291 (8)	0.6200 (2)	0.0663 (11)
O3	0.4800 (3)	0.4212 (7)	0.08568 (19)	0.0570 (9)
O4	0.5212 (3)	0.6833 (6)	0.19453 (18)	0.0515 (9)
C1	0.1869 (5)	0.2697 (9)	0.4574 (2)	0.0461 (11)
H1A	0.0917	0.3363	0.4547	0.055*
C2	0.2974 (5)	0.4680 (10)	0.4639 (3)	0.0538 (13)
H2A	0.2553	0.6289	0.4602	0.065*
H2B	0.3509	0.4552	0.5190	0.065*
C3	0.3884 (5)	0.4185 (10)	0.3843 (3)	0.0507 (12)
H3A	0.4834	0.4852	0.3888	0.061*
C4	0.3056 (4)	0.5000 (9)	0.3052 (3)	0.0472 (11)
H4A	0.2727	0.6693	0.3074	0.057*
C5	0.3438 (5)	0.4104 (9)	0.2149 (3)	0.0455 (11)
C6	0.2449 (4)	0.2432 (9)	0.2100 (3)	0.0451 (12)
C7	0.1891 (5)	0.3056 (10)	0.2990 (3)	0.0484 (12)
H7A	0.0935	0.3704	0.2983	0.058*
C8	0.2235 (5)	0.1373 (9)	0.3750 (3)	0.0443 (11)
H8A	0.1829	−0.0263	0.3696	0.053*
C9	0.3802 (5)	0.1434 (10)	0.3793 (3)	0.0498 (12)
H9A	0.4228	0.0778	0.3264	0.060*
H9B	0.4184	0.0639	0.4320	0.060*
C10	0.2001 (4)	0.0518 (9)	0.1509 (3)	0.0447 (12)
C11	0.0861 (4)	−0.0836 (10)	0.1735 (3)	0.0497 (12)
H11A	0.0378	−0.0470	0.2250	0.060*
C12	0.0430 (5)	−0.2720 (11)	0.1208 (3)	0.0574 (14)
H12A	−0.0351	−0.3632	0.1362	0.069*
C13	0.1140 (5)	−0.3277 (10)	0.0454 (3)	0.0557 (13)
H13A	0.0850	−0.4569	0.0094	0.067*
C14	0.2261 (5)	−0.1934 (10)	0.0239 (3)	0.0552 (13)
H14A	0.2751	−0.2321	−0.0272	0.066*
C15	0.2694 (5)	−0.0031 (9)	0.0747 (3)	0.0493 (12)
H15A	0.3460	0.0899	0.0578	0.059*
C16	0.1536 (5)	0.1475 (10)	0.6058 (3)	0.0493 (13)
C17	0.1899 (5)	−0.0409 (11)	0.6710 (3)	0.0599 (14)
H17A	0.1328	−0.0221	0.7224	0.090*
H17B	0.2868	−0.0254	0.6880	0.090*
H17C	0.1740	−0.1991	0.6452	0.090*
C18	0.4520 (4)	0.4990 (9)	0.1569 (3)	0.0450 (11)
C19	0.6270 (5)	0.7913 (10)	0.1412 (3)	0.0549 (13)
H19A	0.5865	0.8548	0.0863	0.066*
H19B	0.6978	0.6717	0.1266	0.066*
C20	0.6887 (5)	0.9907 (10)	0.1947 (3)	0.0562 (13)
H20A	0.7564	1.0766	0.1600	0.084*
H20B	0.7337	0.9239	0.2468	0.084*
H20C	0.6163	1.1014	0.2121	0.084*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0615 (19)	0.052 (2)	0.0420 (17)	0.0052 (17)	0.0078 (15)	−0.0001 (15)
O2	0.075 (2)	0.073 (3)	0.051 (2)	0.020 (2)	0.0116 (17)	−0.0058 (18)
O3	0.066 (2)	0.059 (2)	0.0466 (18)	−0.0018 (18)	0.0121 (15)	−0.0082 (17)
O4	0.0585 (18)	0.054 (2)	0.0427 (16)	−0.0099 (17)	0.0090 (14)	−0.0013 (16)
C1	0.056 (3)	0.047 (3)	0.035 (2)	0.001 (2)	0.0064 (18)	0.003 (2)
C2	0.072 (3)	0.050 (3)	0.039 (2)	−0.002 (3)	0.005 (2)	−0.009 (2)
C3	0.051 (3)	0.057 (3)	0.044 (3)	−0.005 (2)	0.010 (2)	−0.002 (2)
C4	0.058 (3)	0.040 (3)	0.044 (2)	−0.002 (2)	0.011 (2)	−0.001 (2)
C5	0.054 (3)	0.042 (3)	0.040 (2)	0.007 (2)	0.006 (2)	0.000 (2)
C6	0.043 (2)	0.054 (3)	0.039 (2)	0.006 (2)	0.0055 (19)	0.007 (2)
C7	0.051 (3)	0.050 (3)	0.044 (2)	0.002 (2)	0.0083 (19)	0.004 (2)
C8	0.053 (2)	0.042 (3)	0.038 (2)	0.001 (2)	0.0055 (18)	−0.003 (2)
C9	0.049 (3)	0.053 (3)	0.048 (3)	0.003 (2)	0.001 (2)	0.002 (2)
C10	0.044 (2)	0.050 (3)	0.040 (2)	0.003 (2)	0.0033 (19)	−0.002 (2)
C11	0.052 (3)	0.056 (3)	0.041 (2)	0.000 (3)	0.002 (2)	−0.001 (2)
C12	0.051 (3)	0.065 (4)	0.056 (3)	−0.004 (3)	0.003 (2)	0.003 (3)
C13	0.067 (3)	0.053 (3)	0.048 (3)	−0.001 (3)	−0.003 (2)	0.000 (2)
C14	0.065 (3)	0.061 (4)	0.040 (2)	−0.004 (3)	0.009 (2)	−0.002 (3)
C15	0.058 (3)	0.049 (3)	0.041 (2)	−0.002 (3)	0.005 (2)	−0.002 (2)
C16	0.048 (3)	0.059 (4)	0.041 (3)	−0.009 (3)	0.005 (2)	−0.004 (2)
C17	0.062 (3)	0.071 (4)	0.047 (3)	−0.007 (3)	0.005 (2)	0.004 (3)
C18	0.052 (2)	0.042 (3)	0.041 (2)	0.006 (2)	0.003 (2)	0.003 (2)
C19	0.058 (3)	0.057 (3)	0.051 (3)	−0.008 (3)	0.007 (2)	0.005 (3)
C20	0.060 (3)	0.053 (3)	0.056 (3)	−0.004 (3)	0.003 (2)	0.007 (3)

Geometric parameters (Å, º)

O1—C16	1.334 (5)	C8—H8A	1.0000
O1—C1	1.473 (5)	C9—H9A	0.9900
O2—C16	1.215 (6)	C9—H9B	0.9900
O3—C18	1.212 (5)	C10—C11	1.393 (6)
O4—C18	1.356 (6)	C10—C15	1.395 (6)
O4—C19	1.459 (5)	C11—C12	1.390 (7)
C1—C8	1.513 (6)	C11—H11A	0.9500
C1—C2	1.548 (7)	C12—C13	1.394 (6)
C1—H1A	1.0000	C12—H12A	0.9500
C2—C3	1.546 (6)	C13—C14	1.371 (7)
C2—H2A	0.9900	C13—H13A	0.9500
C2—H2B	0.9900	C14—C15	1.382 (7)
C3—C4	1.517 (7)	C14—H14A	0.9500
C3—C9	1.543 (8)	C15—H15A	0.9500
C3—H3A	1.0000	C16—C17	1.491 (7)
C4—C5	1.527 (6)	C17—H17A	0.9800
C4—C7	1.574 (7)	C17—H17B	0.9800
C4—H4A	1.0000	C17—H17C	0.9800
C5—C6	1.345 (7)	C19—C20	1.505 (7)
C5—C18	1.477 (6)	C19—H19A	0.9900
C6—C10	1.466 (6)	C19—H19B	0.9900
C6—C7	1.519 (6)	C20—H20A	0.9800
C7—C8	1.532 (7)	C20—H20B	0.9800
C7—H7A	1.0000	C20—H20C	0.9800
C8—C9	1.529 (6)
C16—O1—C1	118.0 (4)	C3—C9—H9A	112.9
C18—O4—C19	115.3 (3)	C8—C9—H9B	112.9
O1—C1—C8	105.4 (4)	C3—C9—H9B	112.9
O1—C1—C2	110.6 (3)	H9A—C9—H9B	110.3
C8—C1—C2	103.4 (3)	C11—C10—C15	119.3 (4)
O1—C1—H1A	112.3	C11—C10—C6	118.3 (4)
C8—C1—H1A	112.3	C15—C10—C6	122.5 (4)
C2—C1—H1A	112.3	C12—C11—C10	120.1 (4)
C3—C2—C1	103.2 (4)	C12—C11—H11A	119.9
C3—C2—H2A	111.1	C10—C11—H11A	119.9
C1—C2—H2A	111.1	C11—C12—C13	120.3 (5)
C3—C2—H2B	111.1	C11—C12—H12A	119.9
C1—C2—H2B	111.1	C13—C12—H12A	119.9
H2A—C2—H2B	109.1	C14—C13—C12	119.1 (5)
C4—C3—C9	103.5 (4)	C14—C13—H13A	120.5
C4—C3—C2	105.9 (4)	C12—C13—H13A	120.5
C9—C3—C2	100.8 (4)	C13—C14—C15	121.6 (4)
C4—C3—H3A	115.0	C13—C14—H14A	119.2
C9—C3—H3A	115.0	C15—C14—H14A	119.2
C2—C3—H3A	115.0	C14—C15—C10	119.7 (4)
C3—C4—C5	119.6 (4)	C14—C15—H15A	120.2
C3—C4—C7	102.5 (4)	C10—C15—H15A	120.2
C5—C4—C7	84.5 (3)	O2—C16—O1	123.3 (5)
C3—C4—H4A	115.1	O2—C16—C17	126.1 (4)
C5—C4—H4A	115.1	O1—C16—C17	110.6 (5)
C7—C4—H4A	115.1	C16—C17—H17A	109.5
C6—C5—C18	136.0 (4)	C16—C17—H17B	109.5
C6—C5—C4	95.3 (4)	H17A—C17—H17B	109.5
C18—C5—C4	128.7 (4)	C16—C17—H17C	109.5
C5—C6—C10	138.4 (4)	H17A—C17—H17C	109.5
C5—C6—C7	93.3 (4)	H17B—C17—H17C	109.5
C10—C6—C7	128.1 (4)	O3—C18—O4	122.7 (4)
C6—C7—C8	117.8 (4)	O3—C18—C5	126.6 (5)
C6—C7—C4	86.8 (3)	O4—C18—C5	110.7 (4)
C8—C7—C4	103.2 (4)	O4—C19—C20	106.3 (4)
C6—C7—H7A	115.0	O4—C19—H19A	110.5
C8—C7—H7A	115.0	C20—C19—H19A	110.5
C4—C7—H7A	115.0	O4—C19—H19B	110.5
C1—C8—C9	101.6 (4)	C20—C19—H19B	110.5
C1—C8—C7	106.5 (4)	H19A—C19—H19B	108.7
C9—C8—C7	103.0 (4)	C19—C20—H20A	109.5
C1—C8—H8A	114.7	C19—C20—H20B	109.5
C9—C8—H8A	114.7	H20A—C20—H20B	109.5
C7—C8—H8A	114.7	C19—C20—H20C	109.5
C8—C9—C3	94.3 (4)	H20A—C20—H20C	109.5
C8—C9—H9A	112.9	H20B—C20—H20C	109.5