Benzo­[i]­naphtho­[c,d]­bi­cyclo­[5.4.1]dodecan-12-one

In the title compound, penta­cyclo­[11.8.1.1^3,11.0^7,23.0^15,20]­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.

Computing details

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)

Crystal data

C23H20O	F(000) = 664
Mr = 312.39	Dx = 1.263 Mg m^−3
Monoclinic, P21/a	Mo Kα radiation, λ = 0.71073 Å
a = 12.455 (5) Å	Cell parameters from 24 reflections
b = 12.401 (5) Å	θ = 9.5–18.1°
c = 11.140 (5) Å	µ = 0.08 mm^−1
β = 107.259 (5)°	T = 296 K
V = 1643.1 (12) Å^3	Prism, colorless
Z = 4	0.33 × 0.30 × 0.13 mm

Data collection

Enraf-Nonius FR590 diffractometer	1964 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
Graphite monochromator	θmax = 28.0°, θmin = 2.7°
ω–2θ scans	h = −16→0
Absorption correction: ψ scan (North et al., 1968)	k = 0→16
Tmin = 0.962, Tmax = 0.999	l = −14→14
4131 measured reflections	3 standard reflections every 120 min
3953 independent reflections	intensity decay: 4.3%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.141	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0602P)^2 + 0.0421P] where P = (Fo^2 + 2Fc^2)/3
3953 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

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
C1	0.68162 (17)	−0.00977 (18)	0.53155 (19)	0.0469 (5)
H1A	0.6420	0.0437	0.4710	0.056*
H1B	0.6774	−0.0776	0.4871	0.056*
C2	0.80685 (17)	0.02413 (15)	0.58152 (18)	0.0431 (5)
H2	0.8382	0.0164	0.5110	0.052*
C3	0.87424 (17)	−0.05191 (16)	0.68510 (19)	0.0445 (5)
H3A	0.8366	−0.0568	0.7497	0.053*
H3B	0.8739	−0.1233	0.6495	0.053*
C4	0.99465 (17)	−0.01815 (16)	0.74582 (19)	0.0423 (5)
C5	1.07399 (19)	−0.06855 (19)	0.7026 (2)	0.0549 (6)
H5	1.0501	−0.1174	0.6367	0.066*
C6	1.1896 (2)	−0.0494 (2)	0.7536 (2)	0.0658 (7)
H6	1.2409	−0.0848	0.7215	0.079*
C7	1.2258 (2)	0.0211 (2)	0.8501 (2)	0.0644 (7)
H7	1.3025	0.0322	0.8859	0.077*
C8	1.14861 (17)	0.07763 (18)	0.8968 (2)	0.0483 (5)
C9	1.1908 (2)	0.15121 (19)	0.9968 (2)	0.0571 (6)
H9	1.2681	0.1589	1.0317	0.069*
C10	1.1208 (2)	0.2102 (2)	1.0422 (2)	0.0605 (6)
H10	1.1492	0.2589	1.1074	0.073*
C11	1.00491 (19)	0.19724 (18)	0.9900 (2)	0.0528 (6)
H11	0.9573	0.2389	1.0214	0.063*
C12	0.95776 (17)	0.12609 (16)	0.89467 (18)	0.0406 (5)
C13	1.02992 (16)	0.06159 (16)	0.84405 (18)	0.0401 (5)
C14	0.83033 (17)	0.12364 (18)	0.85001 (19)	0.0454 (5)
H14A	0.8025	0.1566	0.9139	0.054*
H14B	0.8059	0.0490	0.8417	0.054*
C15	0.77668 (17)	0.18151 (16)	0.7242 (2)	0.0460 (5)
H15	0.7971	0.2579	0.7371	0.055*
C16	0.64628 (17)	0.17526 (17)	0.6860 (2)	0.0530 (6)
H16A	0.6194	0.2254	0.7374	0.064*
H16B	0.6162	0.1980	0.5991	0.064*
C17	0.60193 (16)	0.06486 (17)	0.69989 (19)	0.0444 (5)
C18	0.54502 (17)	0.04710 (19)	0.7884 (2)	0.0527 (6)
H18	0.5317	0.1048	0.8353	0.063*
C19	0.50805 (18)	−0.05433 (19)	0.8080 (2)	0.0540 (6)
H19	0.4701	−0.0645	0.8676	0.065*
C20	0.52732 (18)	−0.14005 (19)	0.7395 (2)	0.0507 (5)
H20	0.5029	−0.2087	0.7527	0.061*
C21	0.58310 (17)	−0.12401 (17)	0.6510 (2)	0.0465 (5)
H21	0.5955	−0.1825	0.6047	0.056*
C22	0.62126 (16)	−0.02262 (16)	0.62934 (18)	0.0418 (5)
C23	0.81866 (18)	0.14195 (17)	0.6186 (2)	0.0478 (5)
O1	0.85722 (17)	0.20485 (13)	0.55926 (17)	0.0819 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0488 (13)	0.0524 (13)	0.0366 (11)	−0.0013 (10)	0.0081 (10)	−0.0028 (10)
C2	0.0483 (12)	0.0464 (12)	0.0347 (10)	0.0010 (10)	0.0127 (9)	0.0020 (9)
C3	0.0509 (12)	0.0376 (11)	0.0455 (12)	0.0024 (10)	0.0151 (10)	0.0025 (9)
C4	0.0457 (12)	0.0422 (11)	0.0390 (11)	0.0051 (9)	0.0129 (10)	0.0098 (9)
C5	0.0589 (15)	0.0580 (14)	0.0505 (14)	0.0140 (12)	0.0201 (12)	0.0067 (11)
C6	0.0532 (15)	0.0855 (18)	0.0627 (16)	0.0270 (14)	0.0234 (13)	0.0121 (15)
C7	0.0412 (13)	0.0889 (19)	0.0615 (15)	0.0124 (13)	0.0131 (12)	0.0175 (15)
C8	0.0431 (13)	0.0543 (13)	0.0451 (12)	0.0026 (10)	0.0096 (10)	0.0141 (10)
C9	0.0428 (13)	0.0677 (16)	0.0533 (14)	−0.0074 (12)	0.0028 (11)	0.0133 (12)
C10	0.0609 (16)	0.0629 (16)	0.0483 (14)	−0.0118 (13)	0.0015 (12)	−0.0031 (12)
C11	0.0550 (14)	0.0540 (13)	0.0460 (12)	−0.0008 (11)	0.0099 (11)	−0.0030 (11)
C12	0.0422 (11)	0.0445 (11)	0.0349 (10)	−0.0013 (9)	0.0111 (9)	0.0033 (9)
C13	0.0392 (11)	0.0425 (11)	0.0383 (11)	0.0017 (9)	0.0114 (9)	0.0117 (9)
C14	0.0444 (12)	0.0489 (12)	0.0440 (12)	−0.0002 (10)	0.0149 (10)	−0.0051 (10)
C15	0.0443 (12)	0.0357 (10)	0.0553 (13)	0.0001 (9)	0.0106 (11)	−0.0007 (10)
C16	0.0456 (13)	0.0441 (13)	0.0637 (15)	0.0085 (10)	0.0077 (11)	−0.0034 (11)
C17	0.0334 (11)	0.0453 (12)	0.0507 (13)	0.0030 (9)	0.0063 (10)	−0.0072 (10)
C18	0.0397 (12)	0.0616 (15)	0.0557 (14)	0.0048 (11)	0.0122 (11)	−0.0182 (12)
C19	0.0424 (12)	0.0698 (16)	0.0511 (13)	0.0004 (12)	0.0158 (10)	−0.0013 (12)
C20	0.0462 (13)	0.0539 (13)	0.0503 (13)	−0.0020 (10)	0.0117 (11)	0.0007 (11)
C21	0.0459 (13)	0.0436 (12)	0.0476 (12)	−0.0006 (10)	0.0099 (10)	−0.0085 (10)
C22	0.0350 (11)	0.0486 (12)	0.0379 (10)	−0.0005 (9)	0.0048 (9)	−0.0052 (9)
C23	0.0485 (13)	0.0458 (12)	0.0459 (12)	0.0005 (10)	0.0091 (10)	0.0120 (10)
O1	0.1213 (17)	0.0562 (10)	0.0811 (13)	−0.0109 (11)	0.0499 (13)	0.0169 (10)

Geometric parameters (Å, º)

C1—C22	1.504 (3)	C11—C12	1.372 (3)
C1—C2	1.550 (3)	C11—H11	0.9300
C1—H1A	0.9700	C12—C13	1.438 (3)
C1—H1B	0.9700	C12—C14	1.516 (3)
C2—C23	1.513 (3)	C14—C15	1.539 (3)
C2—C3	1.533 (3)	C14—H14A	0.9700
C2—H2	0.9800	C14—H14B	0.9700
C3—C4	1.510 (3)	C15—C23	1.505 (3)
C3—H3A	0.9700	C15—C16	1.554 (3)
C3—H3B	0.9700	C15—H15	0.9800
C4—C5	1.372 (3)	C16—C17	1.501 (3)
C4—C13	1.443 (3)	C16—H16A	0.9700
C5—C6	1.402 (3)	C16—H16B	0.9700
C5—H5	0.9300	C17—C18	1.392 (3)
C6—C7	1.355 (3)	C17—C22	1.402 (3)
C6—H6	0.9300	C18—C19	1.379 (3)
C7—C8	1.408 (3)	C18—H18	0.9300
C7—H7	0.9300	C19—C20	1.371 (3)
C8—C9	1.415 (3)	C19—H19	0.9300
C8—C13	1.433 (3)	C20—C21	1.378 (3)
C9—C10	1.347 (3)	C20—H20	0.9300
C9—H9	0.9300	C21—C22	1.390 (3)
C10—C11	1.396 (3)	C21—H21	0.9300
C10—H10	0.9300	C23—O1	1.210 (2)
C22—C1—C2	115.75 (17)	C13—C12—C14	125.14 (18)
C22—C1—H1A	108.3	C8—C13—C12	116.79 (19)
C2—C1—H1A	108.3	C8—C13—C4	116.79 (18)
C22—C1—H1B	108.3	C12—C13—C4	126.41 (18)
C2—C1—H1B	108.3	C12—C14—C15	114.77 (16)
H1A—C1—H1B	107.4	C12—C14—H14A	108.6
C23—C2—C3	113.66 (17)	C15—C14—H14A	108.6
C23—C2—C1	111.45 (17)	C12—C14—H14B	108.6
C3—C2—C1	111.79 (16)	C15—C14—H14B	108.6
C23—C2—H2	106.5	H14A—C14—H14B	107.6
C3—C2—H2	106.5	C23—C15—C14	113.72 (17)
C1—C2—H2	106.5	C23—C15—C16	110.29 (18)
C4—C3—C2	114.57 (16)	C14—C15—C16	111.25 (17)
C4—C3—H3A	108.6	C23—C15—H15	107.1
C2—C3—H3A	108.6	C14—C15—H15	107.1
C4—C3—H3B	108.6	C16—C15—H15	107.1
C2—C3—H3B	108.6	C17—C16—C15	113.82 (17)
H3A—C3—H3B	107.6	C17—C16—H16A	108.8
C5—C4—C13	119.3 (2)	C15—C16—H16A	108.8
C5—C4—C3	116.1 (2)	C17—C16—H16B	108.8
C13—C4—C3	124.61 (18)	C15—C16—H16B	108.8
C4—C5—C6	122.7 (2)	H16A—C16—H16B	107.7
C4—C5—H5	118.6	C18—C17—C22	118.9 (2)
C6—C5—H5	118.6	C18—C17—C16	119.82 (19)
C7—C6—C5	119.4 (2)	C22—C17—C16	121.23 (19)
C7—C6—H6	120.3	C19—C18—C17	121.4 (2)
C5—C6—H6	120.3	C19—C18—H18	119.3
C6—C7—C8	120.8 (2)	C17—C18—H18	119.3
C6—C7—H7	119.6	C20—C19—C18	119.8 (2)
C8—C7—H7	119.6	C20—C19—H19	120.1
C7—C8—C9	118.5 (2)	C18—C19—H19	120.1
C7—C8—C13	120.9 (2)	C19—C20—C21	119.7 (2)
C9—C8—C13	120.6 (2)	C19—C20—H20	120.2
C10—C9—C8	121.0 (2)	C21—C20—H20	120.2
C10—C9—H9	119.5	C20—C21—C22	121.7 (2)
C8—C9—H9	119.5	C20—C21—H21	119.1
C9—C10—C11	119.1 (2)	C22—C21—H21	119.1
C9—C10—H10	120.5	C21—C22—C17	118.55 (19)
C11—C10—H10	120.5	C21—C22—C1	119.46 (18)
C12—C11—C10	123.3 (2)	C17—C22—C1	122.00 (19)
C12—C11—H11	118.4	O1—C23—C15	120.2 (2)
C10—C11—H11	118.4	O1—C23—C2	119.7 (2)
C11—C12—C13	119.20 (19)	C15—C23—C2	119.99 (17)
C11—C12—C14	115.66 (18)
C22—C1—C2—C23	−74.4 (2)	C11—C12—C14—C15	103.7 (2)
C22—C1—C2—C3	54.0 (2)	C13—C12—C14—C15	−75.5 (2)
C23—C2—C3—C4	−47.8 (2)	C12—C14—C15—C23	54.9 (2)
C1—C2—C3—C4	−175.00 (16)	C12—C14—C15—C16	−179.85 (17)
C2—C3—C4—C5	−98.7 (2)	C23—C15—C16—C17	81.1 (2)
C2—C3—C4—C13	81.4 (2)	C14—C15—C16—C17	−46.1 (2)
C13—C4—C5—C6	2.8 (3)	C15—C16—C17—C18	114.0 (2)
C3—C4—C5—C6	−177.0 (2)	C15—C16—C17—C22	−62.9 (3)
C4—C5—C6—C7	0.4 (4)	C22—C17—C18—C19	0.2 (3)
C5—C6—C7—C8	−2.0 (4)	C16—C17—C18—C19	−176.8 (2)
C6—C7—C8—C9	−179.3 (2)	C17—C18—C19—C20	0.0 (3)
C6—C7—C8—C13	0.4 (3)	C18—C19—C20—C21	−0.3 (3)
C7—C8—C9—C10	177.7 (2)	C19—C20—C21—C22	0.3 (3)
C13—C8—C9—C10	−2.1 (3)	C20—C21—C22—C17	0.0 (3)
C8—C9—C10—C11	0.6 (3)	C20—C21—C22—C1	−179.98 (19)
C9—C10—C11—C12	0.7 (3)	C18—C17—C22—C21	−0.3 (3)
C10—C11—C12—C13	−0.5 (3)	C16—C17—C22—C21	176.70 (19)
C10—C11—C12—C14	−179.8 (2)	C18—C17—C22—C1	179.71 (18)
C7—C8—C13—C12	−177.61 (19)	C16—C17—C22—C1	−3.3 (3)
C9—C8—C13—C12	2.1 (3)	C2—C1—C22—C21	−114.8 (2)
C7—C8—C13—C4	2.7 (3)	C2—C1—C22—C17	65.3 (3)
C9—C8—C13—C4	−177.57 (18)	C14—C15—C23—O1	−125.5 (2)
C11—C12—C13—C8	−0.8 (3)	C16—C15—C23—O1	108.7 (2)
C14—C12—C13—C8	178.37 (18)	C14—C15—C23—C2	57.8 (3)
C11—C12—C13—C4	178.79 (19)	C16—C15—C23—C2	−67.9 (2)
C14—C12—C13—C4	−2.0 (3)	C3—C2—C23—O1	119.5 (2)
C5—C4—C13—C8	−4.2 (3)	C1—C2—C23—O1	−113.1 (2)
C3—C4—C13—C8	175.60 (18)	C3—C2—C23—C15	−63.9 (3)
C5—C4—C13—C12	176.11 (19)	C1—C2—C23—C15	63.5 (2)
C3—C4—C13—C12	−4.0 (3)