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The title compound, C19H16O, crystallizes with two mol­ecules of opposite chirality in the asymmetric unit. In both mol­ecules, the naphthalene and cyclo­pentanone moieties are individually planar. The two cyclo­pentane rings adopt envelope conformations, while the cyclo­hexane ring adopts a boat conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101010976/sk1493sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101010976/sk1493Isup2.hkl
Contains datablock I

CCDC reference: 173393

Comment top

Isocoumarins are compounds of interest because to their various biological and pharmacological properties (Hill, 1986). Recently, Mal et al. (2000) reported a new synthesis of isocoumarin and have isolated the title compound, (I), in order to extend the scope of the preparation to substituted isocoumarins. However, it was not possible to determine the stereostructure of the molecule by NMR analysis alone. To confirm the structure assignments and stereochemistry, an X-ray structure determination of (I) was undertaken.

There are two independent molecules with opposite chirality in the asymmetric unit of (I). The observed bond lengths and angles agree with each other for both molecules. Within the phenyl rings, the average C—C bond lengths are 1.390 (3) and 1.392 (3) Å for molecules A and B, respectively. The bond lengths and angles observed for the benzo[b]fluorene moiety are only slightly different from those of a related structure, i.e. an azabenzo[b]fluorene derivative (Kubicki & Borowiak, 1995).

In both molecules, the naphtalene and cyclopentanone moieties are individually planar and both of the moieties are coplanar, exhibiting dihedral angles of 1.2 (1) and 2.5 (1)° in molecules A and B. Atom O1 deviates slightly from the attached least-squares plane through the naphthalene and cyclopentanone moieties, with deviations of -0.133 (2) and 0.211 (2) Å for molecules A and B, respectively.

The C12—C16 cyclopentane ring adopts an envelope conformation, with puckering parameters (Cremer & Pople, 1975) Q2 = 0.631 (4) Å and ϕ2 = 72.2 (3)° for molecule A, and Q2 = 0.625 (3) Å and ϕ2 = -71.1 (3)° for molecule B. The least-squares plane through this cyclopentane ring makes dihedral angles of 42.9 (2) and 42.2 (2)° with the cyclopentanone ring in molecules A and B, respectively. The other cyclopentane ring (C13–C18) also adopts an envelope conformation, with puckering parameters (Cremer & Pople, 1975) Q2 = 0.550 (4) Å and ϕ2 = 36.2 (4)° for molecule A, and Q2 = 0.552 (3) Å and ϕ2 = -36.4 (3)° for molecule B. The dihedral angles between the least-squares planes through the two cyclopentane rings are 80.8 (2) and 81.1 (2)° for molecules A and B, respectively. The C12—C16 cyclohexane rings have total puckering amplitudes (QT) of 0.944 (3) and 0.947 (3) Å in molecules A and B, respectively, revealing boat conformations.

Experimental top

To a lithium diisopropylamide solution [2.9 mmol in 5 ml tetrahydrofuran (THF)] at 195 K was added 1,4-methano-2,3,4,4a,11,11a-hexahydro-1H-benzo[b]fluoren-11-one solution (2.03 mmol in 20 ml THF). After stirring for 1 h, the enolate was quenched with MeI (1.3 g, 10.4 mmol, 5 equivalents) and the mixture was stirred for an additional 1 h at 195 K and was then allowed to warm to 298 K. The reaction mixture was acidified with 15 ml 15% HCl solution. Treatment with diethyl ether and column chromatography of the reaction mixture furnished the desired product, (I), in 91% yield, as a white solid which was crystallized from a mixture of ethyl acetate and petroleum ether.

Refinement top

After checking their presence in the difference map, all H atoms were geometrically fixed (C—H = 0.93–0.98 Å) and allowed to ride on their attached atoms.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Figures top
[Figure 1] Fig. 1. The structure of the title compound showing 50% probability displacement ellipsoids and the atom-numbering scheme.
1,4-Methano-11a-methyl-2,3,4,4a,11,11a-hexahydro-1H-benzo[b]fluoren-11-one top
Crystal data top
C19H16OF(000) = 552
Mr = 260.32Dx = 1.264 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 6.2303 (1) ÅCell parameters from 7052 reflections
b = 20.5610 (3) Åθ = 1.9–28.3°
c = 10.7476 (2) ŵ = 0.08 mm1
β = 96.665 (1)°T = 293 K
V = 1367.48 (4) Å3Block, colourless
Z = 40.48 × 0.42 × 0.36 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
2677 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.066
Graphite monochromatorθmax = 28.4°, θmin = 1.9°
Detector resolution: 8.33 pixels mm-1h = 78
ω scansk = 2727
9941 measured reflectionsl = 1412
3470 independent reflections
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.074P)2]
where P = (Fo2 + 2Fc2)/3
3470 reflections(Δ/σ)max < 0.001
363 parametersΔρmax = 0.25 e Å3
1 restraintΔρmin = 0.23 e Å3
Crystal data top
C19H16OV = 1367.48 (4) Å3
Mr = 260.32Z = 4
Monoclinic, P21Mo Kα radiation
a = 6.2303 (1) ŵ = 0.08 mm1
b = 20.5610 (3) ÅT = 293 K
c = 10.7476 (2) Å0.48 × 0.42 × 0.36 mm
β = 96.665 (1)°
Data collection top
Siemens SMART CCD area-detector
diffractometer
2677 reflections with I > 2σ(I)
9941 measured reflectionsRint = 0.066
3470 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0521 restraint
wR(F2) = 0.131H-atom parameters constrained
S = 0.99Δρmax = 0.25 e Å3
3470 reflectionsΔρmin = 0.23 e Å3
363 parameters
Special details top

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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
O1A0.1597 (3)0.31928 (12)0.7501 (2)0.0537 (6)
C1A0.3049 (4)0.30452 (15)0.6895 (3)0.0380 (6)
C2A0.2976 (4)0.30788 (13)0.5523 (2)0.0344 (5)
C3A0.1345 (4)0.33000 (13)0.4673 (3)0.0366 (6)
H3A0.00990.34740.49400.044*
C4A0.1568 (4)0.32612 (13)0.3391 (3)0.0352 (6)
C5A0.0077 (5)0.34731 (15)0.2463 (3)0.0436 (7)
H5A0.13460.36460.27030.052*
C6A0.0159 (6)0.34294 (17)0.1236 (3)0.0525 (8)
H6A0.09420.35710.06390.063*
C7A0.2068 (5)0.31694 (17)0.0856 (3)0.0526 (8)
H7A0.22150.31360.00070.063*
C8A0.3689 (5)0.29689 (15)0.1712 (3)0.0446 (7)
H8A0.49470.28040.14440.054*
C9A0.3508 (5)0.30040 (13)0.3009 (2)0.0356 (6)
C10A0.5185 (4)0.27938 (14)0.3919 (2)0.0366 (6)
H10A0.64650.26330.36720.044*
C11A0.4925 (4)0.28272 (13)0.5151 (3)0.0346 (6)
C12A0.6425 (4)0.26236 (15)0.6274 (2)0.0400 (6)
H12A0.77980.28590.63080.048*
C13A0.6830 (5)0.18773 (17)0.6428 (3)0.0534 (8)
H13A0.79280.16940.59450.064*
C14A0.7330 (7)0.1837 (2)0.7857 (3)0.0716 (12)
H14A0.75470.13950.81610.086*
H14B0.85330.21110.81850.086*
C15A0.5129 (6)0.21177 (19)0.8085 (3)0.0590 (9)
H15A0.48360.21300.89610.071*
C16A0.5242 (4)0.27925 (16)0.7432 (2)0.0401 (6)
C17A0.3652 (7)0.16960 (17)0.7233 (4)0.0662 (10)
H17A0.22760.15590.73710.079*
C18A0.4653 (7)0.15527 (17)0.6247 (4)0.0640 (9)
H18A0.41100.12980.55680.077*
C19A0.6370 (5)0.3311 (2)0.8270 (3)0.0639 (10)
H19A0.64240.37090.78070.096*
H19B0.78140.31720.85570.096*
H19C0.55880.33810.89770.096*
O1B0.3056 (3)0.49627 (12)0.81658 (18)0.0492 (5)
C1B0.1580 (4)0.50867 (13)0.7544 (2)0.0331 (5)
C2B0.1657 (4)0.50406 (13)0.6185 (2)0.0312 (5)
C3B0.3304 (4)0.48180 (13)0.5332 (2)0.0343 (6)
H3B0.45520.46460.56010.041*
C4B0.3087 (4)0.48520 (12)0.4056 (2)0.0342 (6)
C5B0.4767 (5)0.46507 (14)0.3132 (3)0.0437 (7)
H5B0.60310.44770.33760.052*
C6B0.4551 (6)0.47084 (17)0.1901 (3)0.0523 (8)
H6B0.56690.45740.13080.063*
C7B0.2675 (5)0.49672 (17)0.1508 (3)0.0510 (8)
H7B0.25590.50100.06570.061*
C8B0.1009 (5)0.51575 (15)0.2365 (3)0.0427 (7)
H8B0.02390.53250.20900.051*
C9B0.1143 (4)0.51054 (13)0.3659 (2)0.0335 (5)
C10B0.0538 (4)0.53103 (13)0.4571 (2)0.0351 (6)
H10B0.18190.54690.43230.042*
C11B0.0294 (4)0.52768 (13)0.5812 (2)0.0316 (5)
C12B0.1824 (4)0.54774 (14)0.6926 (2)0.0359 (6)
H12B0.31790.52330.69560.043*
C13B0.2289 (5)0.62194 (18)0.7071 (3)0.0505 (8)
H13B0.33880.63930.65790.061*
C14B0.2825 (6)0.6255 (2)0.8496 (3)0.0626 (10)
H14C0.30750.66960.88010.075*
H14D0.40200.59760.88110.075*
C15B0.0626 (5)0.59857 (16)0.8749 (3)0.0524 (8)
H15B0.03610.59730.96300.063*
C16B0.0646 (4)0.53147 (14)0.8076 (2)0.0356 (6)
C17B0.0852 (6)0.64297 (16)0.7901 (4)0.0615 (9)
H17B0.22050.65800.80540.074*
C18B0.0132 (6)0.65629 (16)0.6913 (4)0.0600 (9)
H18B0.04030.68220.62390.072*
C19B0.1712 (5)0.47810 (18)0.8907 (3)0.0551 (8)
H19D0.17510.43870.84310.083*
H19E0.09000.47100.96010.083*
H19F0.31590.49090.92140.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0393 (11)0.0858 (16)0.0380 (10)0.0106 (10)0.0137 (9)0.0075 (10)
C1A0.0330 (14)0.0486 (15)0.0333 (13)0.0008 (12)0.0078 (11)0.0060 (12)
C2A0.0316 (12)0.0405 (14)0.0318 (12)0.0026 (11)0.0067 (10)0.0024 (11)
C3A0.0321 (14)0.0407 (15)0.0377 (14)0.0055 (12)0.0075 (11)0.0007 (12)
C4A0.0355 (14)0.0354 (13)0.0348 (13)0.0014 (11)0.0045 (11)0.0016 (11)
C5A0.0417 (16)0.0484 (16)0.0398 (15)0.0039 (13)0.0011 (12)0.0045 (13)
C6A0.0548 (19)0.0607 (19)0.0400 (15)0.0004 (15)0.0034 (14)0.0042 (15)
C7A0.064 (2)0.0616 (19)0.0317 (13)0.0005 (16)0.0051 (13)0.0020 (14)
C8A0.0533 (18)0.0473 (16)0.0358 (13)0.0009 (14)0.0153 (13)0.0014 (13)
C9A0.0383 (14)0.0373 (14)0.0323 (13)0.0010 (11)0.0080 (11)0.0004 (11)
C10A0.0322 (13)0.0430 (14)0.0365 (13)0.0031 (11)0.0119 (11)0.0009 (12)
C11A0.0286 (13)0.0399 (14)0.0353 (13)0.0011 (11)0.0041 (11)0.0002 (11)
C12A0.0323 (14)0.0540 (18)0.0338 (13)0.0028 (12)0.0035 (11)0.0012 (12)
C13A0.0520 (18)0.060 (2)0.0486 (18)0.0229 (15)0.0063 (14)0.0051 (15)
C14A0.073 (2)0.089 (3)0.053 (2)0.037 (2)0.0053 (19)0.018 (2)
C15A0.0606 (19)0.074 (2)0.0449 (16)0.0205 (18)0.0145 (15)0.0202 (17)
C16A0.0337 (13)0.0552 (17)0.0312 (12)0.0016 (12)0.0032 (10)0.0010 (12)
C17A0.070 (2)0.0482 (19)0.081 (3)0.0023 (17)0.013 (2)0.0168 (18)
C18A0.078 (2)0.0414 (17)0.072 (2)0.0063 (17)0.005 (2)0.0015 (16)
C19A0.0459 (18)0.092 (3)0.0523 (18)0.0057 (18)0.0002 (15)0.0252 (19)
O1B0.0371 (10)0.0756 (15)0.0368 (10)0.0096 (10)0.0125 (8)0.0021 (10)
C1B0.0308 (12)0.0395 (13)0.0301 (11)0.0001 (10)0.0082 (9)0.0018 (11)
C2B0.0265 (12)0.0377 (13)0.0302 (11)0.0019 (11)0.0062 (9)0.0002 (11)
C3B0.0279 (12)0.0405 (14)0.0351 (13)0.0031 (11)0.0063 (10)0.0022 (11)
C4B0.0328 (14)0.0360 (14)0.0331 (12)0.0004 (11)0.0014 (10)0.0035 (11)
C5B0.0391 (15)0.0478 (16)0.0423 (15)0.0009 (12)0.0027 (12)0.0073 (13)
C6B0.0544 (19)0.0584 (19)0.0406 (16)0.0030 (15)0.0095 (14)0.0090 (15)
C7B0.063 (2)0.0587 (18)0.0302 (13)0.0119 (16)0.0010 (13)0.0005 (14)
C8B0.0501 (17)0.0482 (17)0.0304 (12)0.0032 (14)0.0082 (12)0.0010 (12)
C9B0.0376 (13)0.0345 (13)0.0285 (11)0.0053 (11)0.0051 (10)0.0007 (11)
C10B0.0314 (13)0.0424 (14)0.0320 (12)0.0015 (12)0.0064 (10)0.0003 (11)
C11B0.0273 (12)0.0383 (13)0.0297 (12)0.0005 (11)0.0053 (10)0.0007 (11)
C12B0.0237 (11)0.0497 (16)0.0339 (12)0.0028 (10)0.0013 (10)0.0019 (11)
C13B0.0518 (18)0.0586 (19)0.0412 (16)0.0235 (16)0.0062 (14)0.0045 (14)
C14B0.061 (2)0.077 (2)0.0484 (19)0.0311 (19)0.0040 (16)0.0160 (17)
C15B0.0531 (18)0.065 (2)0.0404 (15)0.0138 (15)0.0098 (13)0.0152 (15)
C16B0.0293 (12)0.0488 (15)0.0285 (11)0.0027 (11)0.0029 (10)0.0002 (11)
C17B0.064 (2)0.0460 (18)0.075 (2)0.0024 (15)0.0128 (19)0.0153 (17)
C18B0.069 (2)0.0394 (17)0.070 (2)0.0055 (15)0.0042 (18)0.0010 (15)
C19B0.0441 (16)0.076 (2)0.0445 (15)0.0076 (16)0.0015 (13)0.0196 (16)
Geometric parameters (Å, º) top
O1A—C1A1.214 (3)O1B—C1B1.225 (3)
C1A—C2A1.472 (4)C1B—C2B1.459 (3)
C1A—C16A1.512 (4)C1B—C16B1.512 (3)
C2A—C3A1.363 (4)C2B—C3B1.374 (3)
C2A—C11A1.419 (4)C2B—C11B1.409 (3)
C3A—C4A1.403 (4)C3B—C4B1.395 (4)
C3A—H3A0.9300C3B—H3B0.9300
C4A—C5A1.414 (4)C4B—C5B1.418 (4)
C4A—C9A1.423 (4)C4B—C9B1.428 (4)
C5A—C6A1.346 (4)C5B—C6B1.350 (5)
C5A—H5A0.9300C5B—H5B0.9300
C6A—C7A1.408 (5)C6B—C7B1.394 (5)
C6A—H6A0.9300C6B—H6B0.9300
C7A—C8A1.349 (4)C7B—C8B1.363 (4)
C7A—H7A0.9300C7B—H7B0.9300
C8A—C9A1.414 (4)C8B—C9B1.407 (3)
C8A—H8A0.9300C8B—H8B0.9300
C9A—C10A1.413 (4)C9B—C10B1.413 (4)
C10A—C11A1.355 (4)C10B—C11B1.361 (3)
C10A—H10A0.9300C10B—H10B0.9300
C11A—C12A1.498 (4)C11B—C12B1.499 (3)
C12A—C16A1.557 (4)C12B—C16B1.546 (3)
C12A—C13A1.561 (5)C12B—C13B1.557 (5)
C12A—H12A0.9800C12B—H12B0.9800
C13A—C18A1.504 (5)C13B—C18B1.510 (5)
C13A—C14A1.534 (5)C13B—C14B1.531 (4)
C13A—H13A0.9800C13B—H13B0.9800
C14A—C15A1.533 (5)C14B—C15B1.531 (5)
C14A—H14A0.9700C14B—H14C0.9700
C14A—H14B0.9700C14B—H14D0.9700
C15A—C17A1.497 (6)C15B—C17B1.522 (5)
C15A—C16A1.560 (5)C15B—C16B1.558 (4)
C15A—H15A0.9800C15B—H15B0.9800
C16A—C19A1.515 (4)C16B—C19B1.518 (4)
C17A—C18A1.323 (5)C17B—C18B1.315 (5)
C17A—H17A0.9300C17B—H17B0.9300
C18A—H18A0.9300C18B—H18B0.9300
C19A—H19A0.9600C19B—H19D0.9600
C19A—H19B0.9600C19B—H19E0.9600
C19A—H19C0.9600C19B—H19F0.9600
O1A—C1A—C2A126.0 (3)O1B—C1B—C2B126.4 (2)
O1A—C1A—C16A125.3 (3)O1B—C1B—C16B124.9 (2)
C2A—C1A—C16A108.7 (2)C2B—C1B—C16B108.7 (2)
C3A—C2A—C11A121.9 (2)C3B—C2B—C11B121.8 (2)
C3A—C2A—C1A128.4 (2)C3B—C2B—C1B128.7 (2)
C11A—C2A—C1A109.7 (2)C11B—C2B—C1B109.5 (2)
C2A—C3A—C4A119.2 (2)C2B—C3B—C4B119.3 (2)
C2A—C3A—H3A120.4C2B—C3B—H3B120.3
C4A—C3A—H3A120.4C4B—C3B—H3B120.3
C3A—C4A—C5A122.0 (3)C3B—C4B—C5B121.7 (3)
C3A—C4A—C9A119.3 (2)C3B—C4B—C9B119.6 (2)
C5A—C4A—C9A118.8 (2)C5B—C4B—C9B118.7 (2)
C6A—C5A—C4A121.2 (3)C6B—C5B—C4B120.7 (3)
C6A—C5A—H5A119.4C6B—C5B—H5B119.6
C4A—C5A—H5A119.4C4B—C5B—H5B119.6
C5A—C6A—C7A120.1 (3)C5B—C6B—C7B120.9 (3)
C5A—C6A—H6A119.9C5B—C6B—H6B119.6
C7A—C6A—H6A119.9C7B—C6B—H6B119.6
C8A—C7A—C6A120.6 (3)C8B—C7B—C6B120.3 (3)
C8A—C7A—H7A119.7C8B—C7B—H7B119.9
C6A—C7A—H7A119.7C6B—C7B—H7B119.9
C7A—C8A—C9A121.2 (3)C7B—C8B—C9B121.3 (3)
C7A—C8A—H8A119.4C7B—C8B—H8B119.4
C9A—C8A—H8A119.4C9B—C8B—H8B119.4
C10A—C9A—C8A122.0 (3)C8B—C9B—C10B122.6 (3)
C10A—C9A—C4A119.9 (2)C8B—C9B—C4B118.2 (2)
C8A—C9A—C4A118.1 (3)C10B—C9B—C4B119.2 (2)
C11A—C10A—C9A119.9 (3)C11B—C10B—C9B120.4 (3)
C11A—C10A—H10A120.1C11B—C10B—H10B119.8
C9A—C10A—H10A120.1C9B—C10B—H10B119.8
C10A—C11A—C2A119.8 (3)C10B—C11B—C2B119.6 (2)
C10A—C11A—C12A129.7 (3)C10B—C11B—C12B129.4 (2)
C2A—C11A—C12A110.5 (2)C2B—C11B—C12B110.9 (2)
C11A—C12A—C16A105.8 (2)C11B—C12B—C16B105.2 (2)
C11A—C12A—C13A116.0 (3)C11B—C12B—C13B116.3 (2)
C16A—C12A—C13A102.8 (2)C16B—C12B—C13B103.4 (2)
C11A—C12A—H12A110.6C11B—C12B—H12B110.5
C16A—C12A—H12A110.6C16B—C12B—H12B110.5
C13A—C12A—H12A110.6C13B—C12B—H12B110.5
C18A—C13A—C14A100.4 (3)C18B—C13B—C14B100.2 (3)
C18A—C13A—C12A106.9 (3)C18B—C13B—C12B107.1 (2)
C14A—C13A—C12A99.8 (3)C14B—C13B—C12B99.4 (3)
C18A—C13A—H13A115.9C18B—C13B—H13B115.9
C14A—C13A—H13A115.9C14B—C13B—H13B115.9
C12A—C13A—H13A115.9C12B—C13B—H13B115.9
C15A—C14A—C13A93.3 (3)C13B—C14B—C15B93.7 (2)
C15A—C14A—H14A113.0C13B—C14B—H14C113.0
C13A—C14A—H14A113.0C15B—C14B—H14C113.0
C15A—C14A—H14B113.0C13B—C14B—H14D113.0
C13A—C14A—H14B113.0C15B—C14B—H14D113.0
H14A—C14A—H14B110.4H14C—C14B—H14D110.4
C17A—C15A—C14A100.5 (3)C17B—C15B—C14B99.7 (3)
C17A—C15A—C16A107.2 (3)C17B—C15B—C16B106.9 (2)
C14A—C15A—C16A100.1 (3)C14B—C15B—C16B100.5 (3)
C17A—C15A—H15A115.6C17B—C15B—H15B115.8
C14A—C15A—H15A115.6C14B—C15B—H15B115.8
C16A—C15A—H15A115.6C16B—C15B—H15B115.8
C1A—C16A—C19A108.8 (3)C1B—C16B—C19B108.5 (2)
C1A—C16A—C12A105.2 (2)C1B—C16B—C12B105.31 (19)
C19A—C16A—C12A113.7 (2)C19B—C16B—C12B114.3 (2)
C1A—C16A—C15A113.0 (2)C1B—C16B—C15B113.2 (2)
C19A—C16A—C15A113.6 (3)C19B—C16B—C15B113.2 (2)
C12A—C16A—C15A102.2 (2)C12B—C16B—C15B102.1 (2)
C18A—C17A—C15A107.8 (3)C18B—C17B—C15B107.5 (3)
C18A—C17A—H17A126.1C18B—C17B—H17B126.2
C15A—C17A—H17A126.1C15B—C17B—H17B126.2
C17A—C18A—C13A107.5 (4)C17B—C18B—C13B107.7 (3)
C17A—C18A—H18A126.3C17B—C18B—H18B126.1
C13A—C18A—H18A126.3C13B—C18B—H18B126.1
C16A—C19A—H19A109.5C16B—C19B—H19D109.5
C16A—C19A—H19B109.5C16B—C19B—H19E109.5
H19A—C19A—H19B109.5H19D—C19B—H19E109.5
C16A—C19A—H19C109.5C16B—C19B—H19F109.5
H19A—C19A—H19C109.5H19D—C19B—H19F109.5
H19B—C19A—H19C109.5H19E—C19B—H19F109.5
O1A—C1A—C2A—C3A2.8 (5)O1B—C1B—C2B—C3B4.2 (5)
C16A—C1A—C2A—C3A177.4 (3)C16B—C1B—C2B—C3B175.8 (3)
O1A—C1A—C2A—C11A176.3 (3)O1B—C1B—C2B—C11B175.0 (3)
C16A—C1A—C2A—C11A3.5 (3)C16B—C1B—C2B—C11B5.1 (3)
C11A—C2A—C3A—C4A1.9 (4)C11B—C2B—C3B—C4B2.9 (4)
C1A—C2A—C3A—C4A177.0 (3)C1B—C2B—C3B—C4B176.2 (3)
C2A—C3A—C4A—C5A179.0 (3)C2B—C3B—C4B—C5B177.7 (2)
C2A—C3A—C4A—C9A1.2 (4)C2B—C3B—C4B—C9B1.2 (4)
C3A—C4A—C5A—C6A179.7 (3)C3B—C4B—C5B—C6B177.7 (3)
C9A—C4A—C5A—C6A0.6 (5)C9B—C4B—C5B—C6B1.2 (4)
C4A—C5A—C6A—C7A0.0 (5)C4B—C5B—C6B—C7B0.0 (5)
C5A—C6A—C7A—C8A0.8 (5)C5B—C6B—C7B—C8B1.0 (5)
C6A—C7A—C8A—C9A1.0 (5)C6B—C7B—C8B—C9B0.7 (5)
C7A—C8A—C9A—C10A179.7 (3)C7B—C8B—C9B—C10B178.7 (3)
C7A—C8A—C9A—C4A0.3 (4)C7B—C8B—C9B—C4B0.6 (4)
C3A—C4A—C9A—C10A0.2 (4)C3B—C4B—C9B—C8B177.5 (2)
C5A—C4A—C9A—C10A179.5 (3)C5B—C4B—C9B—C8B1.5 (4)
C3A—C4A—C9A—C8A179.8 (2)C3B—C4B—C9B—C10B0.7 (4)
C5A—C4A—C9A—C8A0.4 (4)C5B—C4B—C9B—C10B179.7 (3)
C8A—C9A—C10A—C11A178.9 (3)C8B—C9B—C10B—C11B177.1 (2)
C4A—C9A—C10A—C11A1.2 (4)C4B—C9B—C10B—C11B1.1 (4)
C9A—C10A—C11A—C2A0.6 (4)C9B—C10B—C11B—C2B0.5 (4)
C9A—C10A—C11A—C12A178.5 (3)C9B—C10B—C11B—C12B178.6 (3)
C3A—C2A—C11A—C10A1.0 (4)C3B—C2B—C11B—C10B2.5 (4)
C1A—C2A—C11A—C10A178.1 (3)C1B—C2B—C11B—C10B176.7 (2)
C3A—C2A—C11A—C12A179.8 (3)C3B—C2B—C11B—C12B179.0 (2)
C1A—C2A—C11A—C12A1.1 (3)C1B—C2B—C11B—C12B1.7 (3)
C10A—C11A—C12A—C16A179.2 (3)C10B—C11B—C12B—C16B179.6 (3)
C2A—C11A—C12A—C16A1.6 (3)C2B—C11B—C12B—C16B2.2 (3)
C10A—C11A—C12A—C13A67.7 (4)C10B—C11B—C12B—C13B66.7 (4)
C2A—C11A—C12A—C13A111.5 (3)C2B—C11B—C12B—C13B111.5 (3)
C11A—C12A—C13A—C18A48.0 (3)C11B—C12B—C13B—C18B48.6 (3)
C16A—C12A—C13A—C18A66.9 (3)C16B—C12B—C13B—C18B66.1 (3)
C11A—C12A—C13A—C14A152.0 (3)C11B—C12B—C13B—C14B152.5 (2)
C16A—C12A—C13A—C14A37.2 (3)C16B—C12B—C13B—C14B37.7 (3)
C18A—C13A—C14A—C15A49.9 (3)C18B—C13B—C14B—C15B50.5 (3)
C12A—C13A—C14A—C15A59.5 (3)C12B—C13B—C14B—C15B59.0 (3)
C13A—C14A—C15A—C17A50.0 (3)C13B—C14B—C15B—C17B50.4 (3)
C13A—C14A—C15A—C16A59.8 (3)C13B—C14B—C15B—C16B59.0 (3)
O1A—C1A—C16A—C19A62.4 (4)O1B—C1B—C16B—C19B63.4 (4)
C2A—C1A—C16A—C19A117.8 (3)C2B—C1B—C16B—C19B116.5 (3)
O1A—C1A—C16A—C12A175.4 (3)O1B—C1B—C16B—C12B173.8 (3)
C2A—C1A—C16A—C12A4.4 (3)C2B—C1B—C16B—C12B6.2 (3)
O1A—C1A—C16A—C15A64.7 (4)O1B—C1B—C16B—C15B63.1 (4)
C2A—C1A—C16A—C15A115.1 (3)C2B—C1B—C16B—C15B116.9 (2)
C11A—C12A—C16A—C1A3.6 (3)C11B—C12B—C16B—C1B5.0 (3)
C13A—C12A—C16A—C1A118.4 (3)C13B—C12B—C16B—C1B117.4 (2)
C11A—C12A—C16A—C19A115.3 (3)C11B—C12B—C16B—C19B114.0 (3)
C13A—C12A—C16A—C19A122.7 (3)C13B—C12B—C16B—C19B123.6 (3)
C11A—C12A—C16A—C15A121.9 (2)C11B—C12B—C16B—C15B123.5 (2)
C13A—C12A—C16A—C15A0.1 (3)C13B—C12B—C16B—C15B1.0 (3)
C17A—C15A—C16A—C1A45.6 (3)C17B—C15B—C16B—C1B45.2 (3)
C14A—C15A—C16A—C1A150.1 (3)C14B—C15B—C16B—C1B148.8 (3)
C17A—C15A—C16A—C19A170.2 (3)C17B—C15B—C16B—C19B169.3 (3)
C14A—C15A—C16A—C19A85.4 (3)C14B—C15B—C16B—C19B87.1 (3)
C17A—C15A—C16A—C12A66.9 (3)C17B—C15B—C16B—C12B67.5 (3)
C14A—C15A—C16A—C12A37.5 (3)C14B—C15B—C16B—C12B36.2 (3)
C14A—C15A—C17A—C18A33.5 (4)C14B—C15B—C17B—C18B33.9 (3)
C16A—C15A—C17A—C18A70.6 (4)C16B—C15B—C17B—C18B70.3 (3)
C15A—C17A—C18A—C13A0.1 (4)C15B—C17B—C18B—C13B0.4 (4)
C14A—C13A—C18A—C17A33.3 (4)C14B—C13B—C18B—C17B33.3 (3)
C12A—C13A—C18A—C17A70.4 (3)C12B—C13B—C18B—C17B70.0 (3)

Experimental details

Crystal data
Chemical formulaC19H16O
Mr260.32
Crystal system, space groupMonoclinic, P21
Temperature (K)293
a, b, c (Å)6.2303 (1), 20.5610 (3), 10.7476 (2)
β (°) 96.665 (1)
V3)1367.48 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.48 × 0.42 × 0.36
Data collection
DiffractometerSiemens SMART CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
9941, 3470, 2677
Rint0.066
(sin θ/λ)max1)0.670
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.131, 0.99
No. of reflections3470
No. of parameters363
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.25, 0.23

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Selected geometric parameters (Å, º) top
O1A—C1A1.214 (3)C1B—C16B1.512 (3)
C1A—C16A1.512 (4)C2B—C3B1.374 (3)
C2A—C3A1.363 (4)C12B—C16B1.546 (3)
C14A—C15A1.533 (5)C14B—C15B1.531 (5)
C15A—C17A1.497 (6)C15B—C17B1.522 (5)
C16A—C19A1.515 (4)C16B—C19B1.518 (4)
O1B—C1B1.225 (3)
C14A—C13A—C12A99.8 (3)O1B—C1B—C2B126.4 (2)
C15A—C14A—C13A93.3 (3)C14B—C13B—C12B99.4 (3)
C17A—C15A—C14A100.5 (3)C13B—C14B—C15B93.7 (2)
C17A—C15A—C16A107.2 (3)C17B—C15B—C14B99.7 (3)
C14A—C15A—C16A100.1 (3)C17B—C15B—C16B106.9 (2)
C19A—C16A—C12A113.7 (2)C14B—C15B—C16B100.5 (3)
C1A—C16A—C15A113.0 (2)C19B—C16B—C12B114.3 (2)
C19A—C16A—C15A113.6 (3)C1B—C16B—C15B113.2 (2)
C18A—C17A—C15A107.8 (3)C18B—C17B—C15B107.5 (3)
C1A—C2A—C11A—C12A1.1 (3)C1B—C2B—C11B—C12B1.7 (3)
C13A—C12A—C16A—C15A0.1 (3)C13B—C12B—C16B—C15B1.0 (3)
C14A—C15A—C16A—C1A150.1 (3)C14B—C15B—C16B—C1B148.8 (3)
C14A—C15A—C16A—C12A37.5 (3)C14B—C15B—C16B—C12B36.2 (3)
C15A—C17A—C18A—C13A0.1 (4)C15B—C17B—C18B—C13B0.4 (4)
 

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