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In the title compound, penta­cyclo­[11.8.1.13,11.07,23.015,20]­tricosa-3,5,7,9,11(23),15,17,19-octaen-22-one, C23H20O, the bi­cyclo­[5.4.1]­dodecan-12-one moiety takes a rigid conformation in which the seven- and eight-membered rings take chair and boat-boat forms, respectively. The mol­ecule has a non-crystallographic mirror symmetry perpendicular to the benzene and naphthalene planes.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010001091X/ob1037sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010001091X/ob1037Isup2.hkl
Contains datablock I

CCDC reference: 153908

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SIR97 (Altomare et al., 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Xtal_GX (Hall et al., 1995); software used to prepare material for publication: SHELXL97.

(I) top
Crystal data top
C23H20OF(000) = 664
Mr = 312.39Dx = 1.263 Mg m3
Monoclinic, P21/aMo Kα radiation, λ = 0.71073 Å
a = 12.455 (5) ÅCell parameters from 24 reflections
b = 12.401 (5) Åθ = 9.5–18.1°
c = 11.140 (5) ŵ = 0.08 mm1
β = 107.259 (5)°T = 296 K
V = 1643.1 (12) Å3Prism, colorless
Z = 40.33 × 0.30 × 0.13 mm
Data collection top
Enraf-Nonius FR590
diffractometer
1964 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
Graphite monochromatorθmax = 28.0°, θmin = 2.7°
ω–2θ scansh = 160
Absorption correction: ψ scan
(North et al., 1968)
k = 016
Tmin = 0.962, Tmax = 0.999l = 1414
4131 measured reflections3 standard reflections every 120 min
3953 independent reflections intensity decay: 4.3%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0602P)2 + 0.0421P]
where P = (Fo2 + 2Fc2)/3
3953 reflections(Δ/σ)max = 0.001
217 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.22 e Å3
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
C10.68162 (17)0.00977 (18)0.53155 (19)0.0469 (5)
H1A0.64200.04370.47100.056*
H1B0.67740.07760.48710.056*
C20.80685 (17)0.02413 (15)0.58152 (18)0.0431 (5)
H20.83820.01640.51100.052*
C30.87424 (17)0.05191 (16)0.68510 (19)0.0445 (5)
H3A0.83660.05680.74970.053*
H3B0.87390.12330.64950.053*
C40.99465 (17)0.01815 (16)0.74582 (19)0.0423 (5)
C51.07399 (19)0.06855 (19)0.7026 (2)0.0549 (6)
H51.05010.11740.63670.066*
C61.1896 (2)0.0494 (2)0.7536 (2)0.0658 (7)
H61.24090.08480.72150.079*
C71.2258 (2)0.0211 (2)0.8501 (2)0.0644 (7)
H71.30250.03220.88590.077*
C81.14861 (17)0.07763 (18)0.8968 (2)0.0483 (5)
C91.1908 (2)0.15121 (19)0.9968 (2)0.0571 (6)
H91.26810.15891.03170.069*
C101.1208 (2)0.2102 (2)1.0422 (2)0.0605 (6)
H101.14920.25891.10740.073*
C111.00491 (19)0.19724 (18)0.9900 (2)0.0528 (6)
H110.95730.23891.02140.063*
C120.95776 (17)0.12609 (16)0.89467 (18)0.0406 (5)
C131.02992 (16)0.06159 (16)0.84405 (18)0.0401 (5)
C140.83033 (17)0.12364 (18)0.85001 (19)0.0454 (5)
H14A0.80250.15660.91390.054*
H14B0.80590.04900.84170.054*
C150.77668 (17)0.18151 (16)0.7242 (2)0.0460 (5)
H150.79710.25790.73710.055*
C160.64628 (17)0.17526 (17)0.6860 (2)0.0530 (6)
H16A0.61940.22540.73740.064*
H16B0.61620.19800.59910.064*
C170.60193 (16)0.06486 (17)0.69989 (19)0.0444 (5)
C180.54502 (17)0.04710 (19)0.7884 (2)0.0527 (6)
H180.53170.10480.83530.063*
C190.50805 (18)0.05433 (19)0.8080 (2)0.0540 (6)
H190.47010.06450.86760.065*
C200.52732 (18)0.14005 (19)0.7395 (2)0.0507 (5)
H200.50290.20870.75270.061*
C210.58310 (17)0.12401 (17)0.6510 (2)0.0465 (5)
H210.59550.18250.60470.056*
C220.62126 (16)0.02262 (16)0.62934 (18)0.0418 (5)
C230.81866 (18)0.14195 (17)0.6186 (2)0.0478 (5)
O10.85722 (17)0.20485 (13)0.55926 (17)0.0819 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0488 (13)0.0524 (13)0.0366 (11)0.0013 (10)0.0081 (10)0.0028 (10)
C20.0483 (12)0.0464 (12)0.0347 (10)0.0010 (10)0.0127 (9)0.0020 (9)
C30.0509 (12)0.0376 (11)0.0455 (12)0.0024 (10)0.0151 (10)0.0025 (9)
C40.0457 (12)0.0422 (11)0.0390 (11)0.0051 (9)0.0129 (10)0.0098 (9)
C50.0589 (15)0.0580 (14)0.0505 (14)0.0140 (12)0.0201 (12)0.0067 (11)
C60.0532 (15)0.0855 (18)0.0627 (16)0.0270 (14)0.0234 (13)0.0121 (15)
C70.0412 (13)0.0889 (19)0.0615 (15)0.0124 (13)0.0131 (12)0.0175 (15)
C80.0431 (13)0.0543 (13)0.0451 (12)0.0026 (10)0.0096 (10)0.0141 (10)
C90.0428 (13)0.0677 (16)0.0533 (14)0.0074 (12)0.0028 (11)0.0133 (12)
C100.0609 (16)0.0629 (16)0.0483 (14)0.0118 (13)0.0015 (12)0.0031 (12)
C110.0550 (14)0.0540 (13)0.0460 (12)0.0008 (11)0.0099 (11)0.0030 (11)
C120.0422 (11)0.0445 (11)0.0349 (10)0.0013 (9)0.0111 (9)0.0033 (9)
C130.0392 (11)0.0425 (11)0.0383 (11)0.0017 (9)0.0114 (9)0.0117 (9)
C140.0444 (12)0.0489 (12)0.0440 (12)0.0002 (10)0.0149 (10)0.0051 (10)
C150.0443 (12)0.0357 (10)0.0553 (13)0.0001 (9)0.0106 (11)0.0007 (10)
C160.0456 (13)0.0441 (13)0.0637 (15)0.0085 (10)0.0077 (11)0.0034 (11)
C170.0334 (11)0.0453 (12)0.0507 (13)0.0030 (9)0.0063 (10)0.0072 (10)
C180.0397 (12)0.0616 (15)0.0557 (14)0.0048 (11)0.0122 (11)0.0182 (12)
C190.0424 (12)0.0698 (16)0.0511 (13)0.0004 (12)0.0158 (10)0.0013 (12)
C200.0462 (13)0.0539 (13)0.0503 (13)0.0020 (10)0.0117 (11)0.0007 (11)
C210.0459 (13)0.0436 (12)0.0476 (12)0.0006 (10)0.0099 (10)0.0085 (10)
C220.0350 (11)0.0486 (12)0.0379 (10)0.0005 (9)0.0048 (9)0.0052 (9)
C230.0485 (13)0.0458 (12)0.0459 (12)0.0005 (10)0.0091 (10)0.0120 (10)
O10.1213 (17)0.0562 (10)0.0811 (13)0.0109 (11)0.0499 (13)0.0169 (10)
Geometric parameters (Å, º) top
C1—C221.504 (3)C11—C121.372 (3)
C1—C21.550 (3)C11—H110.9300
C1—H1A0.9700C12—C131.438 (3)
C1—H1B0.9700C12—C141.516 (3)
C2—C231.513 (3)C14—C151.539 (3)
C2—C31.533 (3)C14—H14A0.9700
C2—H20.9800C14—H14B0.9700
C3—C41.510 (3)C15—C231.505 (3)
C3—H3A0.9700C15—C161.554 (3)
C3—H3B0.9700C15—H150.9800
C4—C51.372 (3)C16—C171.501 (3)
C4—C131.443 (3)C16—H16A0.9700
C5—C61.402 (3)C16—H16B0.9700
C5—H50.9300C17—C181.392 (3)
C6—C71.355 (3)C17—C221.402 (3)
C6—H60.9300C18—C191.379 (3)
C7—C81.408 (3)C18—H180.9300
C7—H70.9300C19—C201.371 (3)
C8—C91.415 (3)C19—H190.9300
C8—C131.433 (3)C20—C211.378 (3)
C9—C101.347 (3)C20—H200.9300
C9—H90.9300C21—C221.390 (3)
C10—C111.396 (3)C21—H210.9300
C10—H100.9300C23—O11.210 (2)
C22—C1—C2115.75 (17)C13—C12—C14125.14 (18)
C22—C1—H1A108.3C8—C13—C12116.79 (19)
C2—C1—H1A108.3C8—C13—C4116.79 (18)
C22—C1—H1B108.3C12—C13—C4126.41 (18)
C2—C1—H1B108.3C12—C14—C15114.77 (16)
H1A—C1—H1B107.4C12—C14—H14A108.6
C23—C2—C3113.66 (17)C15—C14—H14A108.6
C23—C2—C1111.45 (17)C12—C14—H14B108.6
C3—C2—C1111.79 (16)C15—C14—H14B108.6
C23—C2—H2106.5H14A—C14—H14B107.6
C3—C2—H2106.5C23—C15—C14113.72 (17)
C1—C2—H2106.5C23—C15—C16110.29 (18)
C4—C3—C2114.57 (16)C14—C15—C16111.25 (17)
C4—C3—H3A108.6C23—C15—H15107.1
C2—C3—H3A108.6C14—C15—H15107.1
C4—C3—H3B108.6C16—C15—H15107.1
C2—C3—H3B108.6C17—C16—C15113.82 (17)
H3A—C3—H3B107.6C17—C16—H16A108.8
C5—C4—C13119.3 (2)C15—C16—H16A108.8
C5—C4—C3116.1 (2)C17—C16—H16B108.8
C13—C4—C3124.61 (18)C15—C16—H16B108.8
C4—C5—C6122.7 (2)H16A—C16—H16B107.7
C4—C5—H5118.6C18—C17—C22118.9 (2)
C6—C5—H5118.6C18—C17—C16119.82 (19)
C7—C6—C5119.4 (2)C22—C17—C16121.23 (19)
C7—C6—H6120.3C19—C18—C17121.4 (2)
C5—C6—H6120.3C19—C18—H18119.3
C6—C7—C8120.8 (2)C17—C18—H18119.3
C6—C7—H7119.6C20—C19—C18119.8 (2)
C8—C7—H7119.6C20—C19—H19120.1
C7—C8—C9118.5 (2)C18—C19—H19120.1
C7—C8—C13120.9 (2)C19—C20—C21119.7 (2)
C9—C8—C13120.6 (2)C19—C20—H20120.2
C10—C9—C8121.0 (2)C21—C20—H20120.2
C10—C9—H9119.5C20—C21—C22121.7 (2)
C8—C9—H9119.5C20—C21—H21119.1
C9—C10—C11119.1 (2)C22—C21—H21119.1
C9—C10—H10120.5C21—C22—C17118.55 (19)
C11—C10—H10120.5C21—C22—C1119.46 (18)
C12—C11—C10123.3 (2)C17—C22—C1122.00 (19)
C12—C11—H11118.4O1—C23—C15120.2 (2)
C10—C11—H11118.4O1—C23—C2119.7 (2)
C11—C12—C13119.20 (19)C15—C23—C2119.99 (17)
C11—C12—C14115.66 (18)
C22—C1—C2—C2374.4 (2)C11—C12—C14—C15103.7 (2)
C22—C1—C2—C354.0 (2)C13—C12—C14—C1575.5 (2)
C23—C2—C3—C447.8 (2)C12—C14—C15—C2354.9 (2)
C1—C2—C3—C4175.00 (16)C12—C14—C15—C16179.85 (17)
C2—C3—C4—C598.7 (2)C23—C15—C16—C1781.1 (2)
C2—C3—C4—C1381.4 (2)C14—C15—C16—C1746.1 (2)
C13—C4—C5—C62.8 (3)C15—C16—C17—C18114.0 (2)
C3—C4—C5—C6177.0 (2)C15—C16—C17—C2262.9 (3)
C4—C5—C6—C70.4 (4)C22—C17—C18—C190.2 (3)
C5—C6—C7—C82.0 (4)C16—C17—C18—C19176.8 (2)
C6—C7—C8—C9179.3 (2)C17—C18—C19—C200.0 (3)
C6—C7—C8—C130.4 (3)C18—C19—C20—C210.3 (3)
C7—C8—C9—C10177.7 (2)C19—C20—C21—C220.3 (3)
C13—C8—C9—C102.1 (3)C20—C21—C22—C170.0 (3)
C8—C9—C10—C110.6 (3)C20—C21—C22—C1179.98 (19)
C9—C10—C11—C120.7 (3)C18—C17—C22—C210.3 (3)
C10—C11—C12—C130.5 (3)C16—C17—C22—C21176.70 (19)
C10—C11—C12—C14179.8 (2)C18—C17—C22—C1179.71 (18)
C7—C8—C13—C12177.61 (19)C16—C17—C22—C13.3 (3)
C9—C8—C13—C122.1 (3)C2—C1—C22—C21114.8 (2)
C7—C8—C13—C42.7 (3)C2—C1—C22—C1765.3 (3)
C9—C8—C13—C4177.57 (18)C14—C15—C23—O1125.5 (2)
C11—C12—C13—C80.8 (3)C16—C15—C23—O1108.7 (2)
C14—C12—C13—C8178.37 (18)C14—C15—C23—C257.8 (3)
C11—C12—C13—C4178.79 (19)C16—C15—C23—C267.9 (2)
C14—C12—C13—C42.0 (3)C3—C2—C23—O1119.5 (2)
C5—C4—C13—C84.2 (3)C1—C2—C23—O1113.1 (2)
C3—C4—C13—C8175.60 (18)C3—C2—C23—C1563.9 (3)
C5—C4—C13—C12176.11 (19)C1—C2—C23—C1563.5 (2)
C3—C4—C13—C124.0 (3)
 

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