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

The regio- and stereochemistry of the title compound, C₁₈H₁₈O₃, 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) = 0.002 Å
• R factor = 0.041
• wR factor = 0.113
• Data-to-parameter ratio = 17.8

checkCIF/PLATON results

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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-oxo-4-phenyltricyclo[4.2.1.0^2,5]non-3-ene-3-carboxylate

Crystal data

C18H18O3	F(000) = 1200
Mr = 282.32	Dx = 1.262 Mg m^−3
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 16712 reflections
a = 16.2196 (4) Å	θ = 2.6–27.5°
b = 18.2187 (4) Å	µ = 0.09 mm^−1
c = 10.0604 (2) Å	T = 150 K
V = 2972.85 (11) Å^3	Block, colourless
Z = 8	0.34 × 0.32 × 0.30 mm

Data collection

Nonius KappaCCD diffractometer	2591 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.057
Graphite monochromator	θmax = 27.5°, θmin = 2.6°
Detector resolution: 9 pixels mm^-1	h = −20→21
φ scans and ω scans with κ offsets	k = −23→22
27619 measured reflections	l = −11→13
3398 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)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.113	w = 1/[σ^2(Fo^2) + (0.0537P)^2 + 0.8216P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3398 reflections	Δρmax = 0.25 e Å^−3
191 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0048 (13)

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	0.59856 (7)	0.76741 (5)	0.34622 (12)	0.0468 (3)
O2	0.65646 (8)	0.36072 (5)	0.43289 (10)	0.0435 (3)
O3	0.65611 (6)	0.40626 (5)	0.22529 (9)	0.0300 (2)
C1	0.62698 (8)	0.70631 (7)	0.33426 (15)	0.0335 (3)
C2	0.64824 (10)	0.66792 (8)	0.20436 (15)	0.0394 (4)
H2A	0.6915	0.6949	0.1550	0.047*
H2B	0.5990	0.6625	0.1470	0.047*
C3	0.67972 (9)	0.59295 (7)	0.25247 (14)	0.0331 (3)
H3A	0.7140	0.5653	0.1868	0.040*
C4	0.60353 (8)	0.55164 (7)	0.30460 (12)	0.0254 (3)
H4A	0.5569	0.5467	0.2402	0.031*
C5	0.61853 (8)	0.48595 (7)	0.39274 (12)	0.0254 (3)
C6	0.60172 (7)	0.52168 (6)	0.50814 (13)	0.0244 (3)
C7	0.58264 (8)	0.59364 (7)	0.43763 (12)	0.0247 (3)
H7A	0.5246	0.6115	0.4461	0.030*
C8	0.65017 (8)	0.65358 (7)	0.44517 (14)	0.0302 (3)
H8A	0.6598	0.6760	0.5346	0.036*
C9	0.72469 (8)	0.61535 (8)	0.38078 (15)	0.0355 (3)
H9A	0.7710	0.6495	0.3640	0.043*
H9B	0.7441	0.5725	0.4327	0.043*
C10	0.60231 (8)	0.50672 (7)	0.65055 (12)	0.0252 (3)
C11	0.57729 (8)	0.56224 (7)	0.73851 (13)	0.0285 (3)
H11A	0.5606	0.6086	0.7046	0.034*
C12	0.57681 (8)	0.54995 (8)	0.87392 (13)	0.0326 (3)
H12A	0.5598	0.5879	0.9325	0.039*
C13	0.60085 (9)	0.48270 (8)	0.92503 (14)	0.0354 (3)
H13A	0.6003	0.4745	1.0183	0.042*
C14	0.62581 (9)	0.42749 (9)	0.83917 (14)	0.0368 (3)
H14A	0.6425	0.3814	0.8740	0.044*
C15	0.62664 (9)	0.43899 (8)	0.70298 (13)	0.0314 (3)
H15A	0.6438	0.4007	0.6451	0.038*
C16	0.64522 (8)	0.41146 (7)	0.35727 (12)	0.0275 (3)
C17	0.68063 (9)	0.33489 (7)	0.17420 (14)	0.0343 (3)
H17A	0.7180	0.3108	0.2386	0.041*
H17B	0.7110	0.3414	0.0897	0.041*
C18	0.60695 (11)	0.28691 (9)	0.15088 (19)	0.0519 (5)
H18A	0.6250	0.2392	0.1165	0.078*
H18B	0.5703	0.3104	0.0861	0.078*
H18C	0.5773	0.2798	0.2348	0.078*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0533 (7)	0.0233 (5)	0.0638 (8)	0.0028 (5)	−0.0028 (6)	0.0046 (5)
O2	0.0766 (8)	0.0247 (5)	0.0293 (5)	0.0092 (5)	0.0014 (5)	0.0035 (4)
O3	0.0416 (5)	0.0247 (5)	0.0236 (5)	0.0045 (4)	0.0022 (4)	−0.0018 (4)
C1	0.0304 (7)	0.0231 (6)	0.0470 (8)	−0.0053 (5)	−0.0017 (6)	0.0046 (6)
C2	0.0488 (9)	0.0292 (7)	0.0403 (8)	−0.0032 (6)	0.0042 (7)	0.0102 (6)
C3	0.0378 (8)	0.0270 (7)	0.0344 (7)	−0.0002 (6)	0.0096 (6)	0.0039 (6)
C4	0.0290 (7)	0.0231 (6)	0.0243 (6)	−0.0002 (5)	−0.0005 (5)	0.0007 (5)
C5	0.0293 (7)	0.0231 (6)	0.0236 (6)	−0.0023 (5)	0.0005 (5)	0.0007 (5)
C6	0.0243 (6)	0.0224 (6)	0.0264 (6)	−0.0022 (5)	−0.0006 (5)	0.0003 (5)
C7	0.0248 (6)	0.0220 (6)	0.0274 (6)	−0.0003 (5)	−0.0009 (5)	−0.0007 (5)
C8	0.0312 (7)	0.0247 (6)	0.0348 (7)	−0.0039 (5)	−0.0021 (6)	−0.0010 (5)
C9	0.0262 (7)	0.0314 (7)	0.0489 (9)	−0.0036 (5)	0.0018 (6)	0.0033 (6)
C10	0.0245 (6)	0.0275 (6)	0.0235 (6)	−0.0033 (5)	−0.0001 (5)	−0.0002 (5)
C11	0.0292 (7)	0.0278 (6)	0.0285 (7)	−0.0034 (5)	0.0014 (5)	−0.0023 (5)
C12	0.0332 (7)	0.0382 (8)	0.0262 (7)	−0.0055 (6)	0.0022 (5)	−0.0073 (6)
C13	0.0346 (7)	0.0483 (8)	0.0232 (7)	−0.0037 (6)	0.0001 (6)	0.0008 (6)
C14	0.0420 (8)	0.0404 (8)	0.0278 (7)	0.0057 (6)	−0.0008 (6)	0.0071 (6)
C15	0.0366 (7)	0.0326 (7)	0.0249 (7)	0.0048 (6)	0.0014 (5)	0.0011 (5)
C16	0.0353 (7)	0.0240 (6)	0.0231 (6)	−0.0002 (5)	0.0001 (5)	0.0001 (5)
C17	0.0433 (8)	0.0283 (7)	0.0314 (7)	0.0080 (6)	0.0026 (6)	−0.0068 (6)
C18	0.0566 (10)	0.0372 (9)	0.0618 (11)	−0.0023 (8)	0.0021 (8)	−0.0207 (8)

Geometric parameters (Å, º)

O1—C1	1.2108 (17)	C8—C9	1.5380 (19)
O2—C16	1.2110 (16)	C8—H8A	1.0000
O3—C16	1.3429 (16)	C9—H9A	0.9900
O3—C17	1.4536 (15)	C9—H9B	0.9900
C1—C8	1.5196 (19)	C10—C15	1.3987 (18)
C1—C2	1.522 (2)	C10—C11	1.4039 (18)
C2—C3	1.5365 (19)	C11—C12	1.3807 (19)
C2—H2A	0.9900	C11—H11A	0.9500
C2—H2B	0.9900	C12—C13	1.385 (2)
C3—C9	1.538 (2)	C12—H12A	0.9500
C3—C4	1.5391 (18)	C13—C14	1.386 (2)
C3—H3A	1.0000	C13—H13A	0.9500
C4—C5	1.5091 (17)	C14—C15	1.3862 (19)
C4—C7	1.5784 (17)	C14—H14A	0.9500
C4—H4A	1.0000	C15—H15A	0.9500
C5—C6	1.3586 (18)	C17—C18	1.499 (2)
C5—C16	1.4685 (17)	C17—H17A	0.9900
C6—C10	1.4584 (18)	C17—H17B	0.9900
C6—C7	1.5223 (17)	C18—H18A	0.9800
C7—C8	1.5487 (17)	C18—H18B	0.9800
C7—H7A	1.0000	C18—H18C	0.9800
C16—O3—C17	116.66 (10)	C3—C9—C8	95.80 (11)
O1—C1—C8	127.05 (14)	C3—C9—H9A	112.6
O1—C1—C2	126.45 (14)	C8—C9—H9A	112.6
C8—C1—C2	106.49 (11)	C3—C9—H9B	112.6
C1—C2—C3	102.32 (11)	C8—C9—H9B	112.6
C1—C2—H2A	111.3	H9A—C9—H9B	110.1
C3—C2—H2A	111.3	C15—C10—C11	118.65 (12)
C1—C2—H2B	111.3	C15—C10—C6	122.49 (12)
C3—C2—H2B	111.3	C11—C10—C6	118.85 (12)
H2A—C2—H2B	109.2	C12—C11—C10	120.44 (13)
C2—C3—C9	100.73 (11)	C12—C11—H11A	119.8
C2—C3—C4	105.97 (11)	C10—C11—H11A	119.8
C9—C3—C4	102.98 (11)	C11—C12—C13	120.56 (13)
C2—C3—H3A	115.1	C11—C12—H12A	119.7
C9—C3—H3A	115.1	C13—C12—H12A	119.7
C4—C3—H3A	115.1	C12—C13—C14	119.53 (13)
C5—C4—C3	117.29 (11)	C12—C13—H13A	120.2
C5—C4—C7	85.46 (9)	C14—C13—H13A	120.2
C3—C4—C7	102.96 (10)	C15—C14—C13	120.60 (14)
C5—C4—H4A	115.5	C15—C14—H14A	119.7
C3—C4—H4A	115.5	C13—C14—H14A	119.7
C7—C4—H4A	115.5	C14—C15—C10	120.22 (13)
C6—C5—C16	135.20 (12)	C14—C15—H15A	119.9
C6—C5—C4	95.15 (10)	C10—C15—H15A	119.9
C16—C5—C4	129.61 (11)	O2—C16—O3	123.19 (12)
C5—C6—C10	138.47 (12)	O2—C16—C5	126.67 (12)
C5—C6—C7	93.16 (10)	O3—C16—C5	110.14 (11)
C10—C6—C7	128.32 (11)	O3—C17—C18	111.03 (12)
C6—C7—C8	116.15 (10)	O3—C17—H17A	109.4
C6—C7—C4	86.22 (9)	C18—C17—H17A	109.4
C8—C7—C4	103.38 (10)	O3—C17—H17B	109.4
C6—C7—H7A	115.6	C18—C17—H17B	109.4
C8—C7—H7A	115.6	H17A—C17—H17B	108.0
C4—C7—H7A	115.6	C17—C18—H18A	109.5
C1—C8—C9	99.88 (11)	C17—C18—H18B	109.5
C1—C8—C7	103.58 (10)	H18A—C18—H18B	109.5
C9—C8—C7	102.46 (10)	C17—C18—H18C	109.5
C1—C8—H8A	116.2	H18A—C18—H18C	109.5
C9—C8—H8A	116.2	H18B—C18—H18C	109.5
C7—C8—H8A	116.2