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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): o2105.
Published online 2009 August 8. doi:  10.1107/S1600536809030633
PMCID: PMC2970027

4H-Cyclo­penta­[def]phenanthren-4-one

Abstract

In the title compound, C15H8O, the asymmetric unit contains four independent mol­ecules and crystallizes with aromatic π–π stacking inter­actions[centroid–centroid distances = 3.5326 (18) Å].

Related literature

The title compound (Muzart, 1987 [triangle]) can be readily obtained by oxidation of the corresponding hydro­carbon, 4H-cyclo­penta­[def]-phenanthrene, see: Yang & Harvey (1992 [triangle]). We recently obtained it in our low pressure premixed benzene–oxygen combustion system, see: Sun et al. (2008 [triangle]). For our work on the use of a variety of non-organic methods to generate and trap a family of chlorinated fullerene fragments and clusters, see: Huang et al. (1997 [triangle]); Peng et al. (2001 [triangle]); Tan et al. (2008 [triangle]); Xie et al. (2001 [triangle], 2004 [triangle]); For a related structures, see: Peng et al. (2004 [triangle]). For the synthesis, see: Harvey et al. (1992 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2105-scheme1.jpg

Experimental

Crystal data

  • C15H8O
  • M r = 204.1
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2105-efi1.jpg
  • a = 7.7884 (5) Å
  • b = 15.1558 (8) Å
  • c = 17.0236 (10) Å
  • α = 100.588 (5)°
  • β = 101.065 (5)°
  • γ = 91.824 (5)°
  • V = 1933.8 (2) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 293 K
  • 0.45 × 0.22 × 0.20 mm

Data collection

  • Oxford Gemini S Ultra diffractometer
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 [triangle]) T min = 0.962, T max = 0.983
  • 16146 measured reflections
  • 6739 independent reflections
  • 4205 reflections with I > 2σ(I)
  • R int = 0.036

Refinement

  • R[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 0.129
  • S = 0.93
  • 6739 reflections
  • 577 parameters
  • 30 restraints
  • H-atom parameters constrained
  • Δρmax = 0.41 e Å−3
  • Δρmin = −0.26 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2009 [triangle]).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809030633/bx2227sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030633/bx2227Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

The title compound (I) (Muzart,1987) can be readily obtained by oxidation of the corresponding hydrocarbon, 4H-cyclopenta[def]-phenanthrene (Yang & Harvey 1992), but its crystal structure determination has not been carried out yet. During the past decade, our group has used various non-organic methods, such as high-voltage electric discharge in liquid (Huang et al., 1997), vaporized (Xie et al., 2001, 2004) chloroform and CCl4 and solvothermal reaction (Peng et al., 2001) to generate and trap a family of chlorinated fullerene fragments and clusters (Tan et al., 2008). Recently in our low pressure premixed benzene-oxygen combustion system (Sun et al., 2008), we obtained the title compound, C15H8O. The skeleton of title compound is similar to that of previously reported, C15Cl8O, (Peng et al.,2004). We report here the synthesis and crystal structure of the title compound, (I) (Figure 1), which was separated from the products of combustion process. Due to the aromatic nature of the molecule, the crystal packing of (I) is dominated by arene-arene supramolecular contacts and characterized by molecular stacks which are stabilized by offset face-to-face interactions.

Experimental

The title compound, C15H8O, was prepared in low pressure premixed benzene-oxygen flames. The premixed flames conditions for the soot production as the following range: atom C/O ratio:1–2; combustion chamber pressure: 350 torr. The soot collected from the water-cooled coping was extracted with toluene using an ultrasonic bath under room temperature, the resulting nigger-brown solution separated and purified by multi-stage HPLC, finally we obtained one of fractions contained pure C15H8O. The red single crystals suitable for X-ray diffraction crystallized from toluene at room temperature only in one day. The product was analyzed by mass spectrometry. The molecular peak appeared at a mass/charge ratio of 204.

Refinement

All H atoms were placed geometrically with C—H distances of 0.95 Å, N—H distances of 0.88Å and refined using a riding atom model with their isotropic displacement factors, Jiso fixed at 1.2 time the Ueq of the parent N and phenyl C atom, at 1.5 of methyl C atom.

Figures

Fig. 1.
ORTEP plot of the compound. The thermal ellipsoids are drawn at 30% probability level, hydrogen atoms are omitted for clarity.

Crystal data

C15H8OZ = 8
Mr = 204.1F(000) = 848
Triclinic, P1Dx = 1.403 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.7884 (5) ÅCell parameters from 4555 reflections
b = 15.1558 (8) Åθ = 2.5–32.6°
c = 17.0236 (10) ŵ = 0.09 mm1
α = 100.588 (5)°T = 293 K
β = 101.065 (5)°Prism, red
γ = 91.824 (5)°0.45 × 0.22 × 0.20 mm
V = 1933.8 (2) Å3

Data collection

Oxford Gemini S Ultra diffractometer6739 independent reflections
Radiation source: fine-focus sealed tube4205 reflections with I > 2σ(I)
graphiteRint = 0.036
Detector resolution: 16.1903 pixels mm-1θmax = 25.0°, θmin = 2.5°
ω scansh = −9→8
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)k = −18→18
Tmin = 0.962, Tmax = 0.983l = −20→20
16146 measured reflections

Refinement

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) = 0.129H-atom parameters constrained
S = 0.93w = 1/[σ2(Fo2) + (0.0688P)2] where P = (Fo2 + 2Fc2)/3
6739 reflections(Δ/σ)max < 0.001
577 parametersΔρmax = 0.41 e Å3
30 restraintsΔρmin = −0.26 e Å3

Special details

Experimental. CrysAlis RED, Oxford Diffraction (2007) Ltd., Version 1.171.32.5 (release 08-05 CrysAlis171 .NET) (compiled May 8 ,13:10:02) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
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)

xyzUiso*/Ueq
C10.8063 (4)0.33098 (18)0.03517 (17)0.0399 (7)
C20.9978 (3)0.36444 (17)0.05461 (16)0.0367 (7)
C31.0372 (3)0.37987 (16)−0.01840 (16)0.0348 (6)
C40.8892 (3)0.35928 (16)−0.08247 (16)0.0340 (6)
C50.7456 (4)0.32899 (17)−0.05450 (16)0.0356 (6)
C60.5917 (4)0.30514 (18)−0.11001 (17)0.0408 (7)
H6A0.49220.2844−0.09430.049*
C70.5879 (4)0.31286 (19)−0.19101 (17)0.0450 (8)
H7A0.48330.2974−0.22880.054*
C80.7328 (4)0.34248 (18)−0.21725 (17)0.0446 (7)
H8A0.72410.3466−0.27170.053*
C90.8934 (4)0.36642 (17)−0.16181 (16)0.0377 (7)
C101.0617 (4)0.39708 (19)−0.17468 (18)0.0473 (8)
H10A1.07280.4031−0.22690.057*
C111.2049 (4)0.41741 (19)−0.11228 (18)0.0468 (8)
H11A1.31020.4372−0.12360.056*
C121.1994 (4)0.40946 (17)−0.02998 (17)0.0392 (7)
C131.3329 (4)0.42358 (18)0.04128 (19)0.0472 (8)
H13A1.44610.44260.03880.057*
C141.2970 (4)0.40944 (19)0.11378 (19)0.0491 (8)
H14A1.38730.42020.15960.059*
C151.1294 (4)0.37934 (19)0.12227 (17)0.0463 (8)
H15A1.10930.36990.17230.056*
C160.6568 (4)0.5839 (3)0.4052 (2)0.0694 (10)
C170.6797 (4)0.5821 (2)0.4937 (2)0.0525 (8)
C180.7531 (3)0.50091 (18)0.50378 (18)0.0410 (7)
C190.7789 (3)0.45052 (19)0.42931 (16)0.0388 (7)
C200.7242 (4)0.4942 (3)0.3652 (2)0.0632 (11)
C210.7356 (5)0.4504 (3)0.2896 (2)0.0766 (12)
H21A0.69950.47650.24440.092*
C220.8009 (5)0.3669 (3)0.2807 (2)0.0779 (12)
H22A0.80620.33750.22830.093*
C230.8598 (4)0.3236 (2)0.3453 (2)0.0635 (10)
H23A0.90540.26750.33640.076*
C240.8480 (4)0.3675 (2)0.42488 (17)0.0424 (7)
C250.8946 (4)0.3359 (2)0.49970 (18)0.0471 (8)
H25A0.94420.28080.49900.057*
C260.8696 (4)0.38269 (18)0.57053 (18)0.0438 (7)
H26A0.90070.35910.61760.053*
C270.7939 (3)0.47103 (18)0.57593 (17)0.0384 (7)
C280.7557 (4)0.52866 (19)0.64403 (19)0.0503 (8)
H28A0.77930.51240.69490.060*
C290.6842 (4)0.6086 (2)0.6360 (2)0.0628 (10)
H29A0.66000.64520.68220.075*
C300.6458 (4)0.6379 (2)0.5620 (3)0.0669 (11)
H30A0.59900.69310.55870.080*
C31−0.1975 (3)0.08775 (17)0.10259 (15)0.0332 (6)
C32−0.0113 (3)0.11963 (16)0.14630 (15)0.0316 (6)
C330.0789 (3)0.13636 (15)0.08627 (14)0.0292 (6)
C34−0.0332 (3)0.11806 (15)0.00853 (15)0.0285 (6)
C35−0.2014 (3)0.08791 (16)0.01345 (15)0.0302 (6)
C36−0.3248 (3)0.06629 (17)−0.05763 (15)0.0342 (6)
H36A−0.43830.0453−0.05760.041*
C37−0.2745 (4)0.07684 (17)−0.13048 (16)0.0375 (7)
H37A−0.35750.0626−0.17890.045*
C38−0.1079 (4)0.10733 (17)−0.13356 (15)0.0374 (7)
H38A−0.08130.1137−0.18330.045*
C390.0232 (3)0.12901 (16)−0.06143 (15)0.0315 (6)
C400.2048 (4)0.16059 (17)−0.04878 (17)0.0391 (7)
H40A0.24980.1699−0.09360.047*
C410.3131 (4)0.17747 (18)0.02610 (17)0.0399 (7)
H41A0.42950.19730.03060.048*
C420.2528 (3)0.16546 (16)0.09839 (16)0.0335 (6)
C430.3441 (4)0.17931 (17)0.18063 (16)0.0390 (7)
H43A0.46220.19910.19410.047*
C440.2574 (4)0.16333 (17)0.24065 (17)0.0406 (7)
H44A0.32000.17290.29420.049*
C450.0794 (4)0.13330 (17)0.22509 (16)0.0388 (7)
H45A0.02510.12310.26700.047*
C460.8208 (3)−0.10522 (18)0.52660 (16)0.0344 (6)
C470.7622 (3)−0.01303 (17)0.55685 (15)0.0320 (6)
C480.7321 (3)0.02944 (17)0.48979 (15)0.0304 (6)
C490.7657 (3)−0.02706 (17)0.41971 (15)0.0309 (6)
C500.8189 (3)−0.10950 (17)0.43687 (15)0.0319 (6)
C510.8496 (4)−0.17342 (18)0.37382 (16)0.0388 (7)
H51A0.8842−0.22970.38230.047*
C520.8269 (4)−0.15119 (19)0.29552 (16)0.0409 (7)
H52A0.8489−0.19390.25250.049*
C530.7739 (3)−0.06923 (19)0.28018 (16)0.0386 (7)
H53A0.7601−0.05760.22760.046*
C540.7405 (3)−0.00288 (17)0.34402 (15)0.0328 (6)
C550.6794 (4)0.08598 (18)0.34298 (17)0.0399 (7)
H55A0.66140.10680.29410.048*
C560.6472 (4)0.14037 (18)0.41073 (17)0.0394 (7)
H56A0.60860.19710.40650.047*
C570.6706 (3)0.11364 (17)0.48878 (16)0.0341 (6)
C580.6382 (3)0.15905 (18)0.56446 (17)0.0403 (7)
H58A0.59690.21630.56880.048*
C590.6678 (4)0.11875 (18)0.63199 (17)0.0424 (7)
H59A0.64610.15000.68110.051*
C600.7296 (3)0.03219 (18)0.62916 (16)0.0378 (7)
H60A0.74780.00640.67530.045*
O10.7197 (3)0.30949 (15)0.08162 (12)0.0563 (6)
O20.5989 (4)0.64120 (19)0.37039 (19)0.1032 (10)
O3−0.3173 (2)0.06667 (13)0.13308 (11)0.0466 (5)
O40.8593 (3)−0.16354 (13)0.56584 (11)0.0487 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0362 (17)0.0442 (17)0.0390 (17)0.0025 (13)0.0127 (14)0.0018 (13)
C20.0364 (17)0.0351 (15)0.0360 (16)0.0059 (12)0.0061 (13)0.0012 (12)
C30.0315 (16)0.0299 (15)0.0414 (16)0.0041 (12)0.0067 (13)0.0029 (12)
C40.0317 (16)0.0279 (14)0.0395 (16)0.0022 (11)0.0050 (13)0.0016 (11)
C50.0327 (16)0.0358 (15)0.0369 (16)0.0027 (12)0.0064 (13)0.0039 (12)
C60.0332 (17)0.0438 (17)0.0443 (18)−0.0038 (13)0.0084 (13)0.0060 (13)
C70.0393 (18)0.0504 (18)0.0409 (18)−0.0052 (14)−0.0009 (14)0.0084 (13)
C80.049 (2)0.0484 (18)0.0358 (16)−0.0025 (14)0.0065 (14)0.0098 (13)
C90.0369 (17)0.0385 (16)0.0380 (17)−0.0011 (13)0.0072 (13)0.0091 (12)
C100.0449 (19)0.0537 (19)0.0469 (18)−0.0029 (15)0.0115 (15)0.0173 (14)
C110.0386 (18)0.0475 (18)0.059 (2)−0.0019 (14)0.0156 (15)0.0165 (15)
C120.0345 (17)0.0302 (15)0.0514 (18)0.0013 (12)0.0064 (14)0.0066 (13)
C130.0332 (17)0.0432 (18)0.061 (2)−0.0038 (13)0.0040 (15)0.0066 (14)
C140.0395 (19)0.0480 (18)0.049 (2)−0.0028 (14)−0.0082 (15)0.0019 (14)
C150.0435 (19)0.0505 (18)0.0395 (17)0.0011 (14)0.0025 (14)0.0011 (14)
C160.0469 (19)0.070 (2)0.091 (2)−0.0149 (16)−0.0093 (17)0.0422 (19)
C170.0331 (16)0.0526 (18)0.070 (2)−0.0078 (14)0.0007 (14)0.0199 (16)
C180.0284 (16)0.0365 (16)0.055 (2)−0.0100 (13)0.0022 (13)0.0089 (14)
C190.0296 (16)0.0485 (18)0.0372 (17)−0.0114 (14)0.0009 (13)0.0139 (14)
C200.039 (2)0.092 (3)0.057 (2)−0.0307 (19)−0.0119 (16)0.038 (2)
C210.065 (2)0.105 (2)0.060 (2)−0.0390 (19)−0.0037 (16)0.0431 (19)
C220.073 (2)0.107 (3)0.0495 (19)−0.042 (2)0.0203 (17)0.0042 (19)
C230.054 (2)0.066 (2)0.068 (2)−0.0193 (17)0.0235 (18)−0.0038 (18)
C240.0345 (17)0.054 (2)0.0374 (17)−0.0143 (14)0.0069 (13)0.0102 (14)
C250.0442 (19)0.0440 (18)0.053 (2)−0.0002 (14)0.0093 (15)0.0099 (15)
C260.0389 (18)0.0476 (18)0.0422 (18)−0.0092 (14)0.0095 (14)0.0023 (14)
C270.0301 (16)0.0368 (16)0.0446 (18)−0.0074 (12)0.0055 (13)0.0023 (13)
C280.0458 (19)0.0451 (19)0.054 (2)−0.0080 (15)0.0112 (15)−0.0041 (15)
C290.049 (2)0.046 (2)0.087 (3)−0.0020 (16)0.0202 (19)−0.0094 (19)
C300.035 (2)0.0394 (19)0.120 (3)0.0013 (15)0.010 (2)0.007 (2)
C310.0328 (16)0.0344 (15)0.0330 (15)0.0025 (12)0.0090 (12)0.0054 (11)
C320.0340 (16)0.0305 (14)0.0300 (15)0.0039 (11)0.0050 (12)0.0065 (11)
C330.0284 (15)0.0269 (14)0.0297 (14)0.0041 (11)0.0020 (12)0.0023 (11)
C340.0302 (15)0.0247 (13)0.0302 (14)0.0034 (11)0.0061 (11)0.0041 (11)
C350.0274 (15)0.0286 (14)0.0349 (15)0.0013 (11)0.0061 (12)0.0070 (11)
C360.0262 (15)0.0379 (16)0.0360 (16)−0.0007 (12)0.0028 (12)0.0052 (12)
C370.0373 (17)0.0412 (16)0.0287 (15)0.0002 (13)−0.0014 (12)0.0019 (12)
C380.0453 (18)0.0425 (16)0.0261 (15)0.0035 (13)0.0098 (13)0.0080 (12)
C390.0327 (16)0.0316 (14)0.0305 (15)0.0037 (12)0.0075 (12)0.0051 (11)
C400.0388 (18)0.0411 (16)0.0399 (17)−0.0008 (13)0.0150 (14)0.0074 (13)
C410.0305 (16)0.0422 (16)0.0470 (18)−0.0030 (13)0.0116 (13)0.0057 (13)
C420.0308 (16)0.0301 (14)0.0371 (16)0.0034 (12)0.0047 (12)0.0020 (11)
C430.0313 (16)0.0341 (16)0.0444 (17)0.0037 (12)−0.0037 (13)0.0009 (13)
C440.0431 (18)0.0409 (16)0.0312 (16)0.0054 (13)−0.0044 (13)0.0022 (12)
C450.0466 (19)0.0376 (16)0.0311 (16)0.0080 (13)0.0060 (13)0.0053 (12)
C460.0309 (16)0.0383 (16)0.0346 (15)−0.0021 (12)0.0033 (12)0.0129 (13)
C470.0284 (15)0.0359 (15)0.0317 (15)−0.0029 (12)0.0036 (11)0.0099 (12)
C480.0223 (14)0.0333 (15)0.0336 (15)−0.0038 (11)0.0010 (11)0.0071 (12)
C490.0229 (14)0.0376 (16)0.0314 (15)−0.0042 (11)0.0037 (11)0.0077 (12)
C500.0275 (15)0.0352 (15)0.0337 (15)−0.0006 (12)0.0050 (12)0.0100 (12)
C510.0393 (17)0.0372 (16)0.0417 (17)0.0037 (13)0.0095 (13)0.0108 (13)
C520.0425 (18)0.0468 (18)0.0336 (16)0.0032 (14)0.0099 (13)0.0057 (13)
C530.0366 (17)0.0522 (18)0.0302 (15)0.0009 (13)0.0088 (12)0.0138 (13)
C540.0272 (15)0.0372 (16)0.0363 (16)−0.0027 (12)0.0060 (12)0.0143 (12)
C550.0374 (17)0.0474 (18)0.0388 (17)0.0022 (13)0.0047 (13)0.0213 (14)
C560.0374 (17)0.0365 (16)0.0455 (18)0.0029 (13)0.0054 (13)0.0139 (13)
C570.0247 (15)0.0360 (16)0.0396 (16)−0.0039 (12)0.0015 (12)0.0085 (12)
C580.0345 (17)0.0334 (16)0.0509 (19)−0.0022 (13)0.0054 (14)0.0068 (13)
C590.0422 (18)0.0417 (17)0.0400 (17)−0.0007 (13)0.0101 (13)−0.0016 (13)
C600.0371 (17)0.0458 (18)0.0303 (15)−0.0037 (13)0.0046 (12)0.0098 (12)
O10.0450 (13)0.0841 (16)0.0400 (12)−0.0058 (11)0.0129 (10)0.0094 (11)
O20.0798 (18)0.0976 (19)0.133 (2)−0.0129 (14)−0.0255 (15)0.0757 (17)
O30.0400 (12)0.0637 (13)0.0390 (11)−0.0042 (10)0.0136 (9)0.0132 (9)
O40.0678 (15)0.0444 (12)0.0379 (12)0.0088 (10)0.0101 (10)0.0178 (10)

Geometric parameters (Å, °)

C1—O11.213 (3)C31—O31.213 (3)
C1—C51.503 (4)C31—C351.512 (4)
C1—C21.514 (4)C31—C321.516 (4)
C2—C151.366 (4)C32—C451.366 (3)
C2—C31.393 (4)C32—C331.400 (3)
C3—C121.389 (4)C33—C421.376 (3)
C3—C41.409 (4)C33—C341.413 (3)
C4—C91.381 (4)C34—C391.381 (3)
C4—C51.393 (4)C34—C351.396 (3)
C5—C61.368 (4)C35—C361.372 (3)
C6—C71.400 (4)C36—C371.405 (4)
C6—H6A0.9300C36—H36A0.9300
C7—C81.381 (4)C37—C381.377 (4)
C7—H7A0.9300C37—H37A0.9300
C8—C91.407 (4)C38—C391.417 (3)
C8—H8A0.9300C38—H38A0.9300
C9—C101.446 (4)C39—C401.441 (3)
C10—C111.368 (4)C40—C411.363 (4)
C10—H10A0.9300C40—H40A0.9300
C11—C121.437 (4)C41—C421.438 (4)
C11—H11A0.9300C41—H41A0.9300
C12—C131.416 (4)C42—C431.418 (4)
C13—C141.369 (4)C43—C441.380 (4)
C13—H13A0.9300C43—H43A0.9300
C14—C151.411 (4)C44—C451.405 (4)
C14—H14A0.9300C44—H44A0.9300
C15—H15A0.9300C45—H45A0.9300
C16—O21.191 (4)C46—O41.214 (3)
C16—C171.488 (5)C46—C471.514 (4)
C16—C201.559 (6)C46—C501.514 (4)
C17—C301.380 (5)C47—C601.368 (4)
C17—C181.399 (4)C47—C481.396 (3)
C18—C271.371 (4)C48—C571.379 (4)
C18—C191.408 (4)C48—C491.409 (4)
C19—C241.379 (4)C49—C541.383 (3)
C19—C201.384 (4)C49—C501.392 (4)
C20—C211.356 (5)C50—C511.371 (4)
C21—C221.372 (5)C51—C521.414 (4)
C21—H21A0.9300C51—H51A0.9300
C22—C231.393 (5)C52—C531.376 (4)
C22—H22A0.9300C52—H52A0.9300
C23—C241.417 (4)C53—C541.408 (4)
C23—H23A0.9300C53—H53A0.9300
C24—C251.429 (4)C54—C551.445 (4)
C25—C261.334 (4)C55—C561.359 (4)
C25—H25A0.9300C55—H55A0.9300
C26—C271.475 (4)C56—C571.439 (4)
C26—H26A0.9300C56—H56A0.9300
C27—C281.404 (4)C57—C581.417 (4)
C28—C291.368 (4)C58—C591.383 (4)
C28—H28A0.9300C58—H58A0.9300
C29—C301.394 (5)C59—C601.407 (4)
C29—H29A0.9300C59—H59A0.9300
C30—H30A0.9300C60—H60A0.9300
O1—C1—C5126.9 (3)O3—C31—C35127.6 (2)
O1—C1—C2127.6 (3)O3—C31—C32127.0 (2)
C5—C1—C2105.4 (2)C35—C31—C32105.5 (2)
C15—C2—C3118.1 (3)C45—C32—C33118.0 (2)
C15—C2—C1135.8 (3)C45—C32—C31135.6 (2)
C3—C2—C1106.1 (2)C33—C32—C31106.4 (2)
C12—C3—C2126.4 (3)C42—C33—C32126.4 (2)
C12—C3—C4122.5 (3)C42—C33—C34123.0 (2)
C2—C3—C4111.1 (2)C32—C33—C34110.7 (2)
C9—C4—C5126.4 (2)C39—C34—C35126.5 (2)
C9—C4—C3122.9 (2)C39—C34—C33122.4 (2)
C5—C4—C3110.6 (2)C35—C34—C33111.1 (2)
C6—C5—C4117.7 (2)C36—C35—C34117.8 (2)
C6—C5—C1135.6 (2)C36—C35—C31135.8 (2)
C4—C5—C1106.7 (2)C34—C35—C31106.4 (2)
C5—C6—C7118.2 (2)C35—C36—C37118.0 (2)
C5—C6—H6A120.9C35—C36—H36A121.0
C7—C6—H6A120.9C37—C36—H36A121.0
C8—C7—C6122.9 (3)C38—C37—C36123.0 (2)
C8—C7—H7A118.5C38—C37—H37A118.5
C6—C7—H7A118.5C36—C37—H37A118.5
C7—C8—C9120.2 (3)C37—C38—C39120.4 (2)
C7—C8—H8A119.9C37—C38—H38A119.8
C9—C8—H8A119.9C39—C38—H38A119.8
C4—C9—C8114.6 (2)C34—C39—C38114.3 (2)
C4—C9—C10115.0 (2)C34—C39—C40114.7 (2)
C8—C9—C10130.4 (3)C38—C39—C40131.0 (2)
C11—C10—C9121.9 (3)C41—C40—C39122.8 (2)
C11—C10—H10A119.1C41—C40—H40A118.6
C9—C10—H10A119.1C39—C40—H40A118.6
C10—C11—C12122.7 (3)C40—C41—C42121.9 (2)
C10—C11—H11A118.7C40—C41—H41A119.1
C12—C11—H11A118.7C42—C41—H41A119.1
C3—C12—C13114.0 (3)C33—C42—C43114.6 (2)
C3—C12—C11114.9 (2)C33—C42—C41115.2 (2)
C13—C12—C11131.0 (3)C43—C42—C41130.2 (3)
C14—C13—C12120.6 (3)C44—C43—C42119.9 (3)
C14—C13—H13A119.7C44—C43—H43A120.1
C12—C13—H13A119.7C42—C43—H43A120.1
C13—C14—C15123.1 (3)C43—C44—C45123.4 (2)
C13—C14—H14A118.5C43—C44—H44A118.3
C15—C14—H14A118.5C45—C44—H44A118.3
C2—C15—C14117.8 (3)C32—C45—C44117.8 (3)
C2—C15—H15A121.1C32—C45—H45A121.1
C14—C15—H15A121.1C44—C45—H45A121.1
O2—C16—C17128.2 (4)O4—C46—C47127.3 (2)
O2—C16—C20125.8 (4)O4—C46—C50127.4 (2)
C17—C16—C20106.1 (3)C47—C46—C50105.3 (2)
C30—C17—C18117.8 (3)C60—C47—C48118.0 (2)
C30—C17—C16136.2 (4)C60—C47—C46135.6 (2)
C18—C17—C16105.9 (3)C48—C47—C46106.3 (2)
C27—C18—C17125.6 (3)C57—C48—C47126.2 (2)
C27—C18—C19122.6 (3)C57—C48—C49122.8 (2)
C17—C18—C19111.7 (3)C47—C48—C49110.9 (2)
C24—C19—C20126.9 (3)C54—C49—C50125.9 (2)
C24—C19—C18121.5 (3)C54—C49—C48123.0 (3)
C20—C19—C18111.6 (3)C50—C49—C48111.0 (2)
C21—C20—C19117.0 (4)C51—C50—C49118.0 (2)
C21—C20—C16138.3 (3)C51—C50—C46135.5 (3)
C19—C20—C16104.7 (3)C49—C50—C46106.4 (2)
C20—C21—C22119.2 (3)C50—C51—C52117.9 (3)
C20—C21—H21A120.4C50—C51—H51A121.0
C22—C21—H21A120.4C52—C51—H51A121.0
C21—C22—C23124.0 (4)C53—C52—C51122.9 (3)
C21—C22—H22A118.0C53—C52—H52A118.5
C23—C22—H22A118.0C51—C52—H52A118.5
C22—C23—C24118.1 (3)C52—C53—C54120.0 (2)
C22—C23—H23A121.0C52—C53—H53A120.0
C24—C23—H23A121.0C54—C53—H53A120.0
C19—C24—C23114.9 (3)C49—C54—C53115.2 (2)
C19—C24—C25116.7 (3)C49—C54—C55114.4 (2)
C23—C24—C25128.4 (3)C53—C54—C55130.4 (2)
C26—C25—C24122.3 (3)C56—C55—C54122.5 (2)
C26—C25—H25A118.8C56—C55—H55A118.8
C24—C25—H25A118.8C54—C55—H55A118.8
C25—C26—C27121.5 (3)C55—C56—C57122.6 (3)
C25—C26—H26A119.3C55—C56—H56A118.7
C27—C26—H26A119.3C57—C56—H56A118.7
C18—C27—C28115.2 (3)C48—C57—C58114.7 (2)
C18—C27—C26115.3 (3)C48—C57—C56114.7 (2)
C28—C27—C26129.5 (3)C58—C57—C56130.6 (3)
C29—C28—C27120.4 (3)C59—C58—C57120.4 (3)
C29—C28—H28A119.8C59—C58—H58A119.8
C27—C28—H28A119.8C57—C58—H58A119.8
C28—C29—C30123.2 (3)C58—C59—C60122.4 (3)
C28—C29—H29A118.4C58—C59—H59A118.8
C30—C29—H29A118.4C60—C59—H59A118.8
C17—C30—C29117.7 (3)C47—C60—C59118.4 (2)
C17—C30—H30A121.2C47—C60—H60A120.8
C29—C30—H30A121.2C59—C60—H60A120.8
O1—C1—C2—C151.6 (5)O1—C1—C2—C151.6 (5)
C5—C1—C2—C15−177.9 (3)C5—C1—C2—C15−177.9 (3)
O1—C1—C2—C3179.8 (3)O1—C1—C2—C3179.8 (3)
C5—C1—C2—C30.4 (3)C5—C1—C2—C30.4 (3)
C15—C2—C3—C120.0 (4)C15—C2—C3—C120.0 (4)
C1—C2—C3—C12−178.7 (3)C1—C2—C3—C12−178.7 (3)
C15—C2—C3—C4178.5 (2)C15—C2—C3—C4178.5 (2)
C1—C2—C3—C4−0.1 (3)C1—C2—C3—C4−0.1 (3)
C12—C3—C4—C90.3 (4)C12—C3—C4—C90.3 (4)
C2—C3—C4—C9−178.3 (3)C2—C3—C4—C9−178.3 (3)
C12—C3—C4—C5178.4 (3)C12—C3—C4—C5178.4 (3)
C2—C3—C4—C5−0.2 (3)C2—C3—C4—C5−0.2 (3)
C9—C4—C5—C6−1.2 (4)C9—C4—C5—C6−1.2 (4)
C3—C4—C5—C6−179.2 (2)C3—C4—C5—C6−179.2 (2)
C9—C4—C5—C1178.5 (3)C9—C4—C5—C1178.5 (3)
C3—C4—C5—C10.4 (3)C3—C4—C5—C10.4 (3)
O1—C1—C5—C6−0.4 (5)O1—C1—C5—C6−0.4 (5)
C2—C1—C5—C6179.1 (3)C2—C1—C5—C6179.1 (3)
O1—C1—C5—C4−180.0 (3)O1—C1—C5—C4−180.0 (3)
C2—C1—C5—C4−0.5 (3)C2—C1—C5—C4−0.5 (3)
C4—C5—C6—C7−0.2 (4)C4—C5—C6—C7−0.2 (4)
C1—C5—C6—C7−179.7 (3)C1—C5—C6—C7−179.7 (3)
C5—C6—C7—C80.7 (4)C5—C6—C7—C80.7 (4)
C6—C7—C8—C90.1 (5)C6—C7—C8—C90.1 (5)
C5—C4—C9—C81.9 (4)C5—C4—C9—C81.9 (4)
C3—C4—C9—C8179.7 (2)C3—C4—C9—C8179.7 (2)
C5—C4—C9—C10−178.0 (3)C5—C4—C9—C10−178.0 (3)
C3—C4—C9—C10−0.2 (4)C3—C4—C9—C10−0.2 (4)
C7—C8—C9—C4−1.3 (4)C7—C8—C9—C4−1.3 (4)
C7—C8—C9—C10178.6 (3)C7—C8—C9—C10178.6 (3)
C4—C9—C10—C11−0.1 (4)C4—C9—C10—C11−0.1 (4)
C8—C9—C10—C11180.0 (3)C8—C9—C10—C11180.0 (3)
C9—C10—C11—C120.3 (5)C9—C10—C11—C120.3 (5)
C2—C3—C12—C130.5 (4)C2—C3—C12—C130.5 (4)
C4—C3—C12—C13−177.9 (2)C4—C3—C12—C13−177.9 (2)
C2—C3—C12—C11178.3 (3)C2—C3—C12—C11178.3 (3)
C4—C3—C12—C11−0.1 (4)C4—C3—C12—C11−0.1 (4)
C10—C11—C12—C3−0.3 (4)C10—C11—C12—C3−0.3 (4)
C10—C11—C12—C13177.2 (3)C10—C11—C12—C13177.2 (3)
C3—C12—C13—C14−0.9 (4)C3—C12—C13—C14−0.9 (4)
C11—C12—C13—C14−178.3 (3)C11—C12—C13—C14−178.3 (3)
C12—C13—C14—C150.9 (5)C12—C13—C14—C150.9 (5)
C3—C2—C15—C140.0 (4)C3—C2—C15—C140.0 (4)
C1—C2—C15—C14178.1 (3)C1—C2—C15—C14178.1 (3)
C13—C14—C15—C2−0.4 (5)C13—C14—C15—C2−0.4 (5)
O2—C16—C17—C300.9 (6)O2—C16—C17—C300.9 (6)
C20—C16—C17—C30−179.0 (3)C20—C16—C17—C30−179.0 (3)
O2—C16—C17—C18−179.8 (3)O2—C16—C17—C18−179.8 (3)
C20—C16—C17—C180.4 (3)C20—C16—C17—C180.4 (3)
C30—C17—C18—C270.5 (4)C30—C17—C18—C270.5 (4)
C16—C17—C18—C27−179.0 (3)C16—C17—C18—C27−179.0 (3)
C30—C17—C18—C19179.4 (3)C30—C17—C18—C19179.4 (3)
C16—C17—C18—C19−0.1 (3)C16—C17—C18—C19−0.1 (3)
C27—C18—C19—C24−0.3 (4)C27—C18—C19—C24−0.3 (4)
C17—C18—C19—C24−179.2 (2)C17—C18—C19—C24−179.2 (2)
C27—C18—C19—C20178.7 (2)C27—C18—C19—C20178.7 (2)
C17—C18—C19—C20−0.3 (3)C17—C18—C19—C20−0.3 (3)
C24—C19—C20—C211.6 (4)C24—C19—C20—C211.6 (4)
C18—C19—C20—C21−177.3 (3)C18—C19—C20—C21−177.3 (3)
C24—C19—C20—C16179.4 (3)C24—C19—C20—C16179.4 (3)
C18—C19—C20—C160.5 (3)C18—C19—C20—C160.5 (3)
O2—C16—C20—C21−3.4 (6)O2—C16—C20—C21−3.4 (6)
C17—C16—C20—C21176.4 (4)C17—C16—C20—C21176.4 (4)
O2—C16—C20—C19179.6 (3)O2—C16—C20—C19179.6 (3)
C17—C16—C20—C19−0.5 (3)C17—C16—C20—C19−0.5 (3)
C19—C20—C21—C22−0.6 (5)C20—C19—C24—C23−1.1 (4)
C16—C20—C21—C22−177.3 (3)C18—C19—C24—C23177.7 (2)
C20—C21—C22—C23−0.9 (5)C20—C19—C24—C25−179.8 (3)
C21—C22—C23—C241.4 (5)C18—C19—C24—C25−1.0 (4)
C20—C19—C24—C23−1.1 (4)C22—C23—C24—C19−0.4 (4)
C18—C19—C24—C23177.7 (2)C22—C23—C24—C25178.1 (3)
C20—C19—C24—C25−179.8 (3)C19—C24—C25—C261.5 (4)
C18—C19—C24—C25−1.0 (4)C23—C24—C25—C26−177.0 (3)
C22—C23—C24—C19−0.4 (4)C24—C25—C26—C27−0.8 (4)
C22—C23—C24—C25178.1 (3)C17—C18—C27—C280.3 (4)
C19—C24—C25—C261.5 (4)C19—C18—C27—C28−178.5 (2)
C23—C24—C25—C26−177.0 (3)C17—C18—C27—C26179.7 (2)
C24—C25—C26—C27−0.8 (4)C19—C18—C27—C261.0 (4)
C17—C18—C27—C280.3 (4)C25—C26—C27—C18−0.4 (4)
C19—C18—C27—C28−178.5 (2)C25—C26—C27—C28178.9 (3)
C17—C18—C27—C26179.7 (2)C18—C27—C28—C29−0.4 (4)
C19—C18—C27—C261.0 (4)C26—C27—C28—C29−179.8 (3)
C25—C26—C27—C18−0.4 (4)C27—C28—C29—C30−0.3 (5)
C25—C26—C27—C28178.9 (3)C18—C17—C30—C29−1.2 (4)
C18—C27—C28—C29−0.4 (4)C16—C17—C30—C29178.2 (3)
C26—C27—C28—C29−179.8 (3)C28—C29—C30—C171.1 (5)
C27—C28—C29—C30−0.3 (5)O3—C31—C32—C451.1 (5)
C18—C17—C30—C29−1.2 (4)C35—C31—C32—C45−178.9 (3)
C16—C17—C30—C29178.2 (3)O3—C31—C32—C33−179.7 (3)
C28—C29—C30—C171.1 (5)C35—C31—C32—C330.3 (3)
O3—C31—C32—C451.1 (5)C45—C32—C33—C420.2 (4)
C35—C31—C32—C45−178.9 (3)C31—C32—C33—C42−179.2 (2)
O3—C31—C32—C33−179.7 (3)C45—C32—C33—C34179.4 (2)
C35—C31—C32—C330.3 (3)C31—C32—C33—C340.0 (3)
C45—C32—C33—C420.2 (4)C42—C33—C34—C39−0.7 (4)
C31—C32—C33—C42−179.2 (2)C32—C33—C34—C39−180.0 (2)
C45—C32—C33—C34179.4 (2)C42—C33—C34—C35178.8 (2)
C31—C32—C33—C340.0 (3)C32—C33—C34—C35−0.4 (3)
C42—C33—C34—C39−0.7 (4)C39—C34—C35—C360.3 (4)
C32—C33—C34—C39−180.0 (2)C33—C34—C35—C36−179.2 (2)
C42—C33—C34—C35178.8 (2)C39—C34—C35—C31−179.9 (2)
C32—C33—C34—C35−0.4 (3)C33—C34—C35—C310.6 (3)
C39—C34—C35—C360.3 (4)O3—C31—C35—C36−0.8 (5)
C33—C34—C35—C36−179.2 (2)C32—C31—C35—C36179.2 (3)
C39—C34—C35—C31−179.9 (2)O3—C31—C35—C34179.4 (3)
C33—C34—C35—C310.6 (3)C32—C31—C35—C34−0.6 (3)
O3—C31—C35—C36−0.8 (5)C34—C35—C36—C37−0.7 (4)
C32—C31—C35—C36179.2 (3)C31—C35—C36—C37179.5 (3)
O3—C31—C35—C34179.4 (3)C35—C36—C37—C380.3 (4)
C32—C31—C35—C34−0.6 (3)C36—C37—C38—C390.6 (4)
C34—C35—C36—C37−0.7 (4)C35—C34—C39—C380.6 (4)
C31—C35—C36—C37179.5 (3)C33—C34—C39—C38−180.0 (2)
C35—C36—C37—C380.3 (4)C35—C34—C39—C40−179.5 (2)
C36—C37—C38—C390.6 (4)C33—C34—C39—C40−0.1 (4)
C35—C34—C39—C380.6 (4)C37—C38—C39—C34−1.0 (4)
C33—C34—C39—C38−180.0 (2)C37—C38—C39—C40179.2 (3)
C35—C34—C39—C40−179.5 (2)C34—C39—C40—C410.7 (4)
C33—C34—C39—C40−0.1 (4)C38—C39—C40—C41−179.4 (3)
C37—C38—C39—C34−1.0 (4)C39—C40—C41—C42−0.5 (4)
C37—C38—C39—C40179.2 (3)C32—C33—C42—C43−0.3 (4)
C34—C39—C40—C410.7 (4)C34—C33—C42—C43−179.4 (2)
C38—C39—C40—C41−179.4 (3)C32—C33—C42—C41180.0 (2)
C39—C40—C41—C42−0.5 (4)C34—C33—C42—C410.9 (4)
C32—C33—C42—C43−0.3 (4)C40—C41—C42—C33−0.3 (4)
C34—C33—C42—C43−179.4 (2)C40—C41—C42—C43−179.9 (3)
C32—C33—C42—C41180.0 (2)C33—C42—C43—C440.2 (4)
C34—C33—C42—C410.9 (4)C41—C42—C43—C44179.8 (3)
C40—C41—C42—C33−0.3 (4)C42—C43—C44—C450.1 (4)
C40—C41—C42—C43−179.9 (3)C33—C32—C45—C440.0 (4)
C33—C42—C43—C440.2 (4)C31—C32—C45—C44179.1 (3)
C41—C42—C43—C44179.8 (3)C43—C44—C45—C32−0.1 (4)
C42—C43—C44—C450.1 (4)O4—C46—C47—C60−2.2 (5)
C33—C32—C45—C440.0 (4)C50—C46—C47—C60177.1 (3)
C31—C32—C45—C44179.1 (3)O4—C46—C47—C48−179.6 (2)
C43—C44—C45—C32−0.1 (4)C50—C46—C47—C48−0.3 (3)
O4—C46—C47—C60−2.2 (5)C60—C47—C48—C57−0.5 (4)
C50—C46—C47—C60177.1 (3)C46—C47—C48—C57177.5 (2)
O4—C46—C47—C48−179.6 (2)C60—C47—C48—C49−177.9 (2)
C50—C46—C47—C48−0.3 (3)C46—C47—C48—C490.1 (3)
C60—C47—C48—C57−0.5 (4)C57—C48—C49—C540.2 (4)
C46—C47—C48—C57177.5 (2)C47—C48—C49—C54177.7 (2)
C60—C47—C48—C49−177.9 (2)C57—C48—C49—C50−177.3 (2)
C46—C47—C48—C490.1 (3)C47—C48—C49—C500.2 (3)
C57—C48—C49—C540.2 (4)C54—C49—C50—C51−0.1 (4)
C47—C48—C49—C54177.7 (2)C48—C49—C50—C51177.3 (2)
C57—C48—C49—C50−177.3 (2)C54—C49—C50—C46−177.8 (2)
C47—C48—C49—C500.2 (3)C48—C49—C50—C46−0.4 (3)
C54—C49—C50—C51−0.1 (4)O4—C46—C50—C512.6 (5)
C48—C49—C50—C51177.3 (2)C47—C46—C50—C51−176.7 (3)
C54—C49—C50—C46−177.8 (2)O4—C46—C50—C49179.8 (2)
C48—C49—C50—C46−0.4 (3)C47—C46—C50—C490.5 (3)
O4—C46—C50—C512.6 (5)C49—C50—C51—C520.6 (4)
C47—C46—C50—C51−176.7 (3)C46—C50—C51—C52177.6 (3)
O4—C46—C50—C49179.8 (2)C50—C51—C52—C53−0.8 (4)
C47—C46—C50—C490.5 (3)C51—C52—C53—C540.3 (4)
C49—C50—C51—C520.6 (4)C50—C49—C54—C53−0.4 (4)
C46—C50—C51—C52177.6 (3)C48—C49—C54—C53−177.5 (2)
C50—C51—C52—C53−0.8 (4)C50—C49—C54—C55178.1 (2)
C51—C52—C53—C540.3 (4)C48—C49—C54—C551.0 (3)
C50—C49—C54—C53−0.4 (4)C52—C53—C54—C490.2 (4)
C48—C49—C54—C53−177.5 (2)C52—C53—C54—C55−177.9 (2)
C50—C49—C54—C55178.1 (2)C49—C54—C55—C56−0.9 (4)
C48—C49—C54—C551.0 (3)C53—C54—C55—C56177.2 (3)
C52—C53—C54—C490.2 (4)C54—C55—C56—C57−0.3 (4)
C52—C53—C54—C55−177.9 (2)C47—C48—C57—C580.6 (4)
C49—C54—C55—C56−0.9 (4)C49—C48—C57—C58177.7 (2)
C53—C54—C55—C56177.2 (3)C47—C48—C57—C56−178.5 (2)
C54—C55—C56—C57−0.3 (4)C49—C48—C57—C56−1.4 (3)
C47—C48—C57—C580.6 (4)C55—C56—C57—C481.4 (4)
C49—C48—C57—C58177.7 (2)C55—C56—C57—C58−177.4 (3)
C47—C48—C57—C56−178.5 (2)C48—C57—C58—C59−0.2 (3)
C49—C48—C57—C56−1.4 (3)C56—C57—C58—C59178.7 (2)
C55—C56—C57—C481.4 (4)C57—C58—C59—C60−0.3 (4)
C55—C56—C57—C58−177.4 (3)C48—C47—C60—C590.0 (4)
C48—C57—C58—C59−0.2 (3)C46—C47—C60—C59−177.2 (3)
C56—C57—C58—C59178.7 (2)C58—C59—C60—C470.4 (4)
C57—C58—C59—C60−0.3 (4)C24—C23—C22—C211.4 (5)
C48—C47—C60—C590.0 (4)C19—C20—C21—C22−0.6 (5)
C46—C47—C60—C59−177.2 (3)C16—C20—C21—C22−177.3 (3)
C58—C59—C60—C470.4 (4)C23—C22—C21—C20−0.9 (5)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2227).

References

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