organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2414-3146

13,13′-Bi(dibenzo[a,i]fluorenyl­­idene)

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aUniversity of Mainz, Department of Chemistry, Duesbergweg 10-14, 55099 Mainz, Germany
*Correspondence e-mail: detert@uni-mainz.de

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 10 February 2022; accepted 11 February 2022; online 17 February 2022)

The asymmetric unit of the title compound, C42H24, contains two almost identical mol­ecules. The mol­ecules have approximate D2 symmetry. They show a largely twisted double bond, the mol­ecular halves enclosing dihedral angles of 62.86 (4) and 61.22 (3)°. The crystal studied was twinned by non-merohedry.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Benzoannulated fulvenes attract chemists because of their electronic properties (Bergmann et al. 1953a[Bergmann, E. D., Fischer, E., Hirshberg, Y., Lavie, D., Sprinzak, Y. & Szmuszkovicz, J. (1953a). Bull. Soc. Chim. Fr. pp. 798-809.],b[Bergmann, E. D., Fischer, E. & Jaffe, J. H. (1953b). J. Am. Chem. Soc. 75, 3230-3233.]), their intense colour, the question of aromaticity and the participation of radical character in their ground state (Kanawati et al., 2012[Kanawati, B., Genest, A., Schmitt-Kopplin, P. & Lenoir, D. (2012). J. Mol. Model. 18, 5089-5095.]; Wentrup et al., 2016[Wentrup, C., Regimbald-Krnel, M. J., Müller, D. & Comba, P. (2016). Angew. Chem. Int. Ed. 55, 14600-14605.]). In the overcrowded alkene, steric strain prevents the mol­ecule from being planar; a single line in the ESR spectrum (Franzen & Joschek, 1961[Franzen, V. & Joschek, H. I. (1961). Justus Liebigs Ann. Chem. 648, 63-68.]) and a simulated torsion angle of 52° (based on diffraction data, Beck et al., 1994[Beck, A. H., Gompper, R., Hartmann, K. & Yokugawa, K. (1994). Chimia, 48, 492-493.]) between the two penta­cyclic halves give evidence for a significant contribution of a radical species. The unit cell is filled with 16 mol­ecules, eight mol­ecules of type A (Fig. 1[link]) and eight of type B. The two independent mol­ecules, A and B, are nearly identical. A packing diagram shows their mutual orientation in the unit cell (Fig. 2[link]). Mol­ecule A consists of two planes, A1, A2, connected via the central C1A—C22A bond. The maximum deviation of carbon atoms from the mean planes are −0.254 (4) Å for C2 (A1) and 0.162 (4) Å for C39 (A2). The dihedral angle between these planes is 62.86 (4)° and the length of the central C1A—C22A bond is 1.408 (5) Å. The values for mol­ecule B are very similar: maximum deviations from the mean planes are −0.293 (4) Å for C5 (B1) and 0.170 (4) Å for C26 (B2). The dihedral angle amounts to 61.22 (3)° and the length of the central C1B—C22B bond is 1.395 (5) Å. Whereas the length of the twisted and elongated bond connecting the two halves of mol­ecules A and B [1.408 (5) and 1.395 (5) Å, respectively] correlates very well with the calculated value of 1.408 Å, the calculated torsion angle of 52° is about 10° too small. The solid material gives a very weak single ESR signal.

[Figure 1]
Figure 1
View of one of the two mol­ecules in the asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms are omitted for clarity.
[Figure 2]
Figure 2
A partial packing diagram viewed along the b-axis. The two symmetry-independent mol­ecules are drawn with different colours.

Synthesis and crystallization

The dark-green title compound was prepared according to literature procedures (Magidson, 1925[Magidson, O. I. (1925). Ber. Dtsch. Chem. Ges. A/B, 58, 433-442.]; Detert & Schollmeyer, 2019[Detert, H. & Schollmeyer, D. (2019). IUCRData, 4, x190236.]). Single crystals of the title compound were obtained by slow evaporation of a saturated solution in chloro­form-d1.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1[link]. The crystal was twinned by non-merohedry. The fractional contribution of the minor twin component refined to 0.4648 (15).

Table 1
Experimental details

Crystal data
Chemical formula C42H24
Mr 528.61
Crystal system, space group Monoclinic, C2/c
Temperature (K) 120
a, b, c (Å) 36.6150 (18), 8.0709 (3), 36.282 (3)
β (°) 90.863 (5)
V3) 10720.8 (10)
Z 16
Radiation type Mo Kα
μ (mm−1) 0.07
Crystal size (mm) 0.28 × 0.22 × 0.15
 
Data collection
Diffractometer Stoe IPDS 2T
No. of measured, independent and observed [I > 2σ(I)] reflections 41460, 41460, 22495
(sin θ/λ)max−1) 0.661
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.072, 0.228, 1.03
No. of reflections 41460
No. of parameters 758
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.32, −0.33
Computer programs: X-AREA WinXpose, Recipe and Integrate (Stoe & Cie, 2019[Stoe & Cie (2019). X-RED and X-AREA. Stoe & Cie, Darmstadt, Germany.]), SHELXT2014 (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2018/3 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]) and PLATON (Spek, 2020[Spek, A. L. (2020). Acta Cryst. E76, 1-11.]).

Structural data


Computing details top

Data collection: X-AREA WinXpose (Stoe & Cie, 2019); cell refinement: X-AREA Recipe (Stoe & Cie, 2019); data reduction: X-AREA Integrate (Stoe & Cie, 2019); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020).

13,13'-Bi(dibenzo[b,i]fluorenylidene) top
Crystal data top
C42H24F(000) = 4416
Mr = 528.61Dx = 1.310 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 36.6150 (18) ÅCell parameters from 16781 reflections
b = 8.0709 (3) Åθ = 2.2–28.4°
c = 36.282 (3) ŵ = 0.07 mm1
β = 90.863 (5)°T = 120 K
V = 10720.8 (10) Å3Block, green
Z = 160.28 × 0.22 × 0.15 mm
Data collection top
Stoe IPDS 2T
diffractometer
22495 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focusθmax = 28.0°, θmin = 2.2°
Detector resolution: 6.67 pixels mm-1h = 4848
rotation method scansk = 1010
41460 measured reflectionsl = 4747
41460 independent reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.072H-atom parameters constrained
wR(F2) = 0.228 w = 1/[σ2(Fo2) + (0.0953P)2 + 14.3038P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
41460 reflectionsΔρmax = 0.32 e Å3
758 parametersΔρmin = 0.33 e Å3
0 restraints
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Hydrogen atoms attached to carbons were placed at calculated positions and were refined in the riding-model approximation with C–H = 0.95 Å, and with Uiso(H) = 1.2 Ueq(C). Refined as a two-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C1A0.07601 (11)0.8616 (4)0.43505 (10)0.0313 (8)
C2A0.04302 (11)0.8118 (5)0.45484 (10)0.0325 (8)
C3A0.00551 (11)0.8345 (5)0.44590 (11)0.0330 (9)
C4A0.00823 (11)0.9106 (5)0.41312 (11)0.0338 (9)
H4A0.0084420.9466960.3949830.041*
C5A0.04480 (11)0.9328 (5)0.40715 (11)0.0374 (9)
H5A0.0531430.9836440.3849540.045*
C6A0.07020 (12)0.8817 (5)0.43333 (11)0.0423 (10)
H6A0.0955870.8971930.4287260.051*
C7A0.05844 (12)0.8094 (6)0.46557 (12)0.0438 (10)
H7A0.0757780.7739640.4831140.053*
C8A0.02062 (13)0.7872 (6)0.47296 (13)0.0389 (10)
C9A0.00861 (14)0.7251 (6)0.50747 (15)0.0435 (11)
H9A0.0261700.6876920.5245910.052*
C10A0.02781 (13)0.7175 (6)0.51687 (14)0.0422 (11)
H10A0.0355230.6819500.5407070.051*
C11A0.05324 (14)0.7636 (4)0.49039 (14)0.0340 (11)
C12A0.09275 (12)0.7830 (5)0.49452 (13)0.0352 (9)
C13A0.11511 (14)0.7405 (5)0.52453 (16)0.0422 (13)
H13A0.1048150.6933540.5459930.051*
C14A0.15180 (15)0.7670 (6)0.52286 (16)0.0493 (14)
H14A0.1669050.7406840.5435610.059*
C15A0.16780 (12)0.8335 (5)0.49064 (12)0.0423 (10)
C16A0.20604 (12)0.8565 (6)0.48900 (13)0.0488 (11)
H16A0.2205340.8348880.5103950.059*
C17A0.22268 (13)0.9083 (6)0.45803 (13)0.0512 (12)
H17A0.2484120.9232000.4577380.061*
C18A0.20144 (12)0.9397 (5)0.42645 (13)0.0435 (10)
H18A0.2130050.9731700.4044040.052*
C19A0.16396 (11)0.9228 (5)0.42680 (12)0.0369 (9)
H19A0.1501610.9447540.4049610.044*
C20A0.14565 (11)0.8731 (5)0.45915 (11)0.0349 (9)
C21A0.10666 (11)0.8519 (5)0.46200 (11)0.0334 (9)
C22A0.07728 (10)0.9001 (4)0.39723 (10)0.0302 (8)
C23A0.09461 (10)1.0466 (4)0.38085 (10)0.0310 (8)
C24A0.10843 (10)1.1956 (5)0.39726 (11)0.0331 (8)
C25A0.10835 (13)1.2314 (5)0.43535 (15)0.0387 (11)
H25A0.0976161.1546310.4518120.046*
C26A0.12339 (12)1.3741 (5)0.44906 (13)0.0449 (11)
H26A0.1229421.3959940.4747740.054*
C27A0.13953 (12)1.4885 (5)0.42501 (13)0.0455 (11)
H27A0.1512751.5844110.4346920.055*
C28A0.13843 (11)1.4630 (5)0.38838 (13)0.0431 (10)
H28A0.1485161.5440240.3725080.052*
C29A0.12261 (11)1.3183 (5)0.37287 (12)0.0374 (9)
C30A0.12101 (12)1.2941 (6)0.33423 (13)0.0421 (10)
H30A0.1315491.3746030.3185280.051*
C31A0.10469 (12)1.1580 (5)0.31904 (12)0.0389 (9)
H31A0.1027281.1455500.2930490.047*
C32A0.09086 (10)1.0366 (4)0.34277 (10)0.0318 (8)
C33A0.07080 (10)0.8859 (5)0.33337 (10)0.0322 (8)
C34A0.06220 (11)0.8233 (5)0.29800 (11)0.0357 (9)
H34A0.0676410.8852200.2765060.043*
C35A0.04593 (11)0.6719 (5)0.29539 (11)0.0381 (10)
H35A0.0392120.6298490.2717940.046*
C36A0.03880 (10)0.5757 (5)0.32729 (11)0.0335 (9)
C37A0.02452 (11)0.4132 (5)0.32325 (12)0.0371 (9)
H37A0.0188470.3724000.2992790.044*
C38A0.01875 (11)0.3139 (5)0.35321 (11)0.0373 (9)
H38A0.0091360.2053950.3500750.045*
C39A0.02721 (11)0.3744 (5)0.38863 (11)0.0350 (9)
H39A0.0232550.3056420.4094410.042*
C40A0.04107 (10)0.5307 (5)0.39376 (11)0.0338 (9)
H40A0.0467700.5674630.4180420.041*
C41A0.04708 (10)0.6384 (5)0.36367 (10)0.0301 (8)
C42A0.06203 (11)0.8035 (5)0.36603 (11)0.0314 (8)
C1B0.17996 (10)0.8223 (4)0.17836 (10)0.0298 (8)
C2B0.20174 (10)0.8753 (4)0.21063 (10)0.0311 (8)
C3B0.19396 (11)0.8642 (4)0.24910 (11)0.0322 (8)
C4B0.16185 (11)0.7937 (5)0.26409 (11)0.0324 (8)
H4B0.1431570.7545340.2478780.039*
C5B0.15727 (12)0.7810 (5)0.30123 (13)0.0369 (9)
H5B0.1358400.7304760.3104700.044*
C6B0.18403 (12)0.8422 (6)0.32604 (12)0.0451 (11)
H6B0.1804100.8354660.3518730.054*
C7B0.21519 (12)0.9113 (5)0.31268 (11)0.0431 (10)
H7B0.2329050.9546910.3294790.052*
C8B0.22172 (11)0.9199 (5)0.27428 (11)0.0367 (9)
C9B0.25598 (11)0.9744 (5)0.26096 (13)0.0423 (10)
H9B0.2735301.0180620.2778840.051*
C10B0.26429 (12)0.9656 (5)0.22457 (12)0.0405 (10)
H10B0.2878800.9953260.2162460.049*
C11B0.23700 (10)0.9112 (5)0.19954 (11)0.0341 (9)
C12B0.23937 (11)0.8775 (5)0.16018 (11)0.0357 (9)
C13B0.26945 (12)0.8977 (6)0.13727 (12)0.0454 (11)
H13B0.2920300.9367510.1471510.055*
C14B0.26618 (12)0.8611 (6)0.10081 (12)0.0496 (11)
H14B0.2869150.8692240.0854880.060*
C15B0.23212 (12)0.8108 (6)0.08541 (11)0.0399 (9)
C16B0.22857 (14)0.7850 (7)0.04678 (15)0.0495 (12)
H16B0.2495830.7940730.0318610.059*
C17B0.19579 (16)0.7476 (5)0.03061 (17)0.0488 (15)
H17B0.1939000.7298700.0047690.059*
C18B0.16495 (14)0.7359 (5)0.05275 (14)0.0396 (12)
H18B0.1419420.7112810.0416050.047*
C19B0.16715 (13)0.7589 (4)0.09006 (15)0.0337 (11)
H19B0.1455900.7513050.1042000.040*
C20B0.20063 (11)0.7937 (5)0.10798 (11)0.0321 (8)
C21B0.20568 (10)0.8187 (5)0.14677 (10)0.0315 (8)
C22B0.14263 (11)0.7877 (5)0.17778 (11)0.0297 (8)
C23B0.12514 (10)0.6437 (4)0.16011 (10)0.0296 (8)
C24B0.14033 (11)0.4913 (4)0.14716 (10)0.0318 (8)
C25B0.17781 (11)0.4493 (5)0.14893 (11)0.0354 (9)
H25B0.1946720.5252690.1597030.042*
C26B0.19051 (13)0.3003 (5)0.13535 (12)0.0412 (10)
H26B0.2157760.2742400.1370220.049*
C27B0.16596 (13)0.1882 (5)0.11915 (12)0.0430 (10)
H27B0.1747050.0882860.1086300.052*
C28B0.12987 (14)0.2219 (5)0.11844 (13)0.0401 (11)
H28B0.1135190.1420590.1083030.048*
C29B0.11555 (11)0.3713 (5)0.13220 (11)0.0351 (9)
C30B0.07747 (11)0.4026 (5)0.13225 (11)0.0379 (9)
H30B0.0613410.3239630.1212830.045*
C31B0.06338 (11)0.5417 (5)0.14752 (11)0.0371 (9)
H31B0.0377090.5583160.1481000.044*
C32B0.08730 (10)0.6603 (5)0.16241 (11)0.0320 (8)
C33B0.07942 (10)0.8130 (5)0.18178 (10)0.0310 (8)
C34B0.04491 (11)0.8804 (5)0.18937 (11)0.0355 (9)
H34B0.0232390.8212540.1831820.043*
C35B0.04314 (11)1.0326 (5)0.20582 (11)0.0370 (9)
H35B0.0200071.0780000.2117020.044*
C36B0.07533 (10)1.1238 (5)0.21423 (10)0.0330 (9)
C37B0.07272 (12)1.2866 (6)0.22848 (12)0.0376 (9)
H37B0.0492401.3318690.2329000.045*
C38B0.10282 (12)1.3802 (5)0.23602 (11)0.0391 (10)
H38B0.1004811.4881760.2461320.047*
C39B0.13736 (12)1.3143 (5)0.22860 (11)0.0365 (10)
H39B0.1584441.3800730.2332310.044*
C40B0.14149 (11)1.1578 (5)0.21489 (10)0.0327 (9)
H40B0.1653271.1167810.2103670.039*
C41B0.11080 (10)1.0557 (4)0.20732 (10)0.0306 (8)
C42B0.11221 (10)0.8906 (4)0.19212 (10)0.0294 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.036 (2)0.0251 (19)0.033 (2)0.0041 (16)0.0001 (15)0.0019 (15)
C2A0.039 (2)0.028 (2)0.030 (2)0.0011 (18)0.0001 (16)0.0007 (16)
C3A0.039 (2)0.028 (2)0.032 (2)0.0004 (17)0.0031 (16)0.0023 (16)
C4A0.037 (2)0.029 (2)0.036 (2)0.0008 (17)0.0037 (16)0.0002 (16)
C5A0.041 (2)0.036 (2)0.035 (2)0.0030 (18)0.0017 (17)0.0025 (17)
C6A0.040 (2)0.046 (3)0.041 (2)0.003 (2)0.0012 (18)0.0014 (19)
C7A0.040 (3)0.048 (3)0.043 (3)0.003 (2)0.0061 (18)0.001 (2)
C8A0.047 (3)0.037 (2)0.033 (2)0.005 (2)0.0030 (18)0.000 (2)
C9A0.044 (3)0.048 (3)0.038 (3)0.004 (2)0.005 (2)0.007 (2)
C10A0.051 (3)0.043 (2)0.033 (3)0.004 (2)0.001 (2)0.009 (2)
C11A0.041 (3)0.030 (2)0.031 (3)0.0014 (16)0.0004 (19)0.0013 (14)
C12A0.041 (2)0.0323 (18)0.032 (2)0.005 (2)0.0043 (17)0.0042 (19)
C13A0.041 (3)0.049 (3)0.036 (3)0.0051 (18)0.007 (2)0.0016 (16)
C14A0.046 (3)0.063 (3)0.039 (3)0.011 (2)0.010 (2)0.001 (2)
C15A0.042 (3)0.043 (3)0.042 (3)0.004 (2)0.0092 (18)0.007 (2)
C16A0.040 (3)0.057 (3)0.049 (3)0.002 (2)0.012 (2)0.009 (2)
C17A0.041 (3)0.053 (3)0.059 (3)0.001 (2)0.008 (2)0.007 (2)
C18A0.039 (2)0.037 (2)0.054 (3)0.0005 (19)0.0004 (19)0.002 (2)
C19A0.036 (2)0.028 (2)0.046 (2)0.0024 (17)0.0037 (17)0.0034 (17)
C20A0.038 (2)0.026 (2)0.040 (2)0.0033 (17)0.0064 (17)0.0051 (16)
C21A0.038 (2)0.0269 (19)0.035 (2)0.0049 (17)0.0035 (16)0.0034 (16)
C22A0.030 (2)0.0266 (19)0.034 (2)0.0052 (16)0.0002 (15)0.0006 (15)
C23A0.030 (2)0.0267 (19)0.037 (2)0.0028 (16)0.0020 (15)0.0022 (16)
C24A0.027 (2)0.028 (2)0.044 (2)0.0046 (17)0.0003 (16)0.0016 (19)
C25A0.045 (3)0.028 (2)0.043 (3)0.0016 (18)0.001 (2)0.0016 (17)
C26A0.049 (3)0.032 (2)0.053 (3)0.004 (2)0.001 (2)0.007 (2)
C27A0.043 (3)0.026 (2)0.068 (3)0.0009 (19)0.003 (2)0.008 (2)
C28A0.039 (2)0.029 (2)0.062 (3)0.0003 (18)0.007 (2)0.000 (2)
C29A0.034 (2)0.025 (2)0.053 (3)0.0035 (17)0.0049 (18)0.0043 (18)
C30A0.039 (2)0.036 (2)0.051 (3)0.001 (2)0.0085 (19)0.009 (2)
C31A0.041 (2)0.037 (2)0.039 (2)0.0028 (19)0.0040 (18)0.0064 (18)
C32A0.028 (2)0.031 (2)0.036 (2)0.0055 (16)0.0000 (15)0.0022 (16)
C33A0.033 (2)0.034 (2)0.030 (2)0.0033 (16)0.0006 (15)0.0023 (16)
C34A0.033 (2)0.041 (3)0.032 (2)0.0038 (18)0.0014 (16)0.0044 (18)
C35A0.038 (2)0.045 (3)0.031 (2)0.0014 (19)0.0019 (16)0.0045 (18)
C36A0.028 (2)0.037 (2)0.035 (2)0.0047 (17)0.0014 (15)0.0002 (17)
C37A0.031 (2)0.039 (2)0.041 (2)0.0011 (18)0.0004 (16)0.0080 (18)
C38A0.034 (2)0.036 (2)0.042 (2)0.0017 (18)0.0025 (17)0.0052 (19)
C39A0.039 (2)0.029 (2)0.037 (2)0.0036 (17)0.0004 (16)0.0011 (16)
C40A0.036 (2)0.032 (2)0.034 (2)0.0008 (17)0.0000 (16)0.0005 (16)
C41A0.027 (2)0.032 (2)0.032 (2)0.0014 (16)0.0019 (14)0.0000 (16)
C42A0.030 (2)0.032 (2)0.032 (2)0.0018 (18)0.0006 (15)0.0001 (18)
C1B0.032 (2)0.0222 (19)0.035 (2)0.0009 (15)0.0015 (15)0.0010 (15)
C2B0.030 (2)0.0249 (19)0.039 (2)0.0010 (15)0.0014 (15)0.0024 (16)
C3B0.034 (2)0.0261 (19)0.036 (2)0.0015 (16)0.0020 (15)0.0012 (16)
C4B0.031 (2)0.0331 (19)0.033 (2)0.0035 (18)0.0018 (15)0.0014 (19)
C5B0.031 (2)0.044 (2)0.036 (3)0.0046 (19)0.0002 (17)0.004 (2)
C6B0.039 (2)0.061 (3)0.035 (2)0.005 (2)0.0004 (17)0.001 (2)
C7B0.042 (3)0.051 (3)0.037 (2)0.002 (2)0.0060 (17)0.0061 (19)
C8B0.033 (2)0.036 (2)0.041 (2)0.0009 (18)0.0036 (16)0.0034 (18)
C9B0.038 (3)0.043 (2)0.045 (2)0.007 (2)0.0068 (19)0.007 (2)
C10B0.033 (2)0.045 (3)0.043 (3)0.0077 (19)0.0020 (18)0.0002 (19)
C11B0.030 (2)0.032 (2)0.040 (2)0.0018 (16)0.0005 (16)0.0023 (17)
C12B0.033 (2)0.034 (2)0.040 (2)0.0000 (17)0.0020 (16)0.0007 (17)
C13B0.031 (2)0.059 (3)0.046 (3)0.007 (2)0.0040 (18)0.004 (2)
C14B0.036 (2)0.071 (3)0.043 (3)0.001 (2)0.0096 (19)0.002 (2)
C15B0.036 (2)0.045 (3)0.038 (2)0.001 (2)0.0060 (17)0.004 (2)
C16B0.039 (3)0.072 (3)0.038 (3)0.004 (2)0.009 (2)0.002 (3)
C17B0.049 (3)0.064 (4)0.034 (3)0.007 (2)0.006 (2)0.0061 (17)
C18B0.039 (3)0.044 (3)0.036 (3)0.0048 (17)0.001 (2)0.0024 (16)
C19B0.033 (2)0.031 (3)0.037 (3)0.0017 (14)0.0024 (19)0.0000 (14)
C20B0.032 (2)0.0275 (18)0.037 (2)0.0039 (18)0.0053 (16)0.0008 (19)
C21B0.032 (2)0.025 (2)0.037 (2)0.0022 (16)0.0031 (15)0.0009 (16)
C22B0.032 (2)0.0235 (16)0.034 (2)0.0010 (18)0.0008 (15)0.0021 (18)
C23B0.030 (2)0.0275 (19)0.031 (2)0.0007 (16)0.0041 (14)0.0022 (15)
C24B0.036 (2)0.0281 (19)0.031 (2)0.0024 (16)0.0008 (15)0.0021 (16)
C25B0.043 (2)0.026 (2)0.037 (2)0.0004 (17)0.0005 (17)0.0013 (16)
C26B0.048 (3)0.033 (2)0.043 (3)0.006 (2)0.0010 (19)0.004 (2)
C27B0.064 (3)0.025 (2)0.039 (3)0.004 (2)0.001 (2)0.0027 (18)
C28B0.054 (3)0.0267 (19)0.040 (3)0.005 (2)0.006 (2)0.000 (2)
C29B0.045 (2)0.028 (2)0.032 (2)0.0053 (18)0.0040 (16)0.0004 (16)
C30B0.039 (2)0.033 (2)0.041 (2)0.0069 (18)0.0069 (17)0.0016 (17)
C31B0.038 (2)0.036 (2)0.037 (2)0.0041 (18)0.0033 (17)0.0011 (17)
C32B0.032 (2)0.0288 (19)0.036 (2)0.0030 (16)0.0013 (15)0.0049 (17)
C33B0.029 (2)0.033 (2)0.032 (2)0.0004 (17)0.0015 (15)0.0004 (17)
C34B0.029 (2)0.038 (2)0.040 (2)0.0019 (17)0.0004 (16)0.0029 (17)
C35B0.035 (2)0.043 (2)0.034 (2)0.0047 (18)0.0005 (16)0.0031 (18)
C36B0.028 (2)0.038 (2)0.034 (2)0.0028 (17)0.0018 (15)0.0051 (17)
C37B0.042 (2)0.0347 (19)0.036 (3)0.006 (2)0.0030 (18)0.001 (2)
C38B0.050 (3)0.034 (2)0.033 (2)0.0053 (19)0.0030 (18)0.0013 (17)
C39B0.044 (2)0.031 (2)0.034 (2)0.0016 (19)0.0026 (17)0.0026 (18)
C40B0.034 (2)0.032 (2)0.032 (2)0.0001 (17)0.0006 (15)0.0027 (17)
C41B0.035 (2)0.0284 (19)0.029 (2)0.0026 (16)0.0004 (15)0.0036 (15)
C42B0.0271 (19)0.031 (2)0.030 (2)0.0012 (16)0.0006 (14)0.0031 (15)
Geometric parameters (Å, º) top
C1A—C22A1.408 (5)C1B—C22B1.395 (5)
C1A—C2A1.471 (5)C1B—C2B1.470 (5)
C1A—C21A1.479 (5)C1B—C21B1.494 (5)
C2A—C11A1.393 (6)C2B—C11B1.389 (5)
C2A—C3A1.418 (5)C2B—C3B1.432 (5)
C3A—C4A1.424 (5)C3B—C4B1.421 (5)
C3A—C8A1.433 (6)C3B—C8B1.429 (5)
C4A—C5A1.365 (6)C4B—C5B1.364 (6)
C4A—H4A0.9500C4B—H4B0.9500
C5A—C6A1.401 (5)C5B—C6B1.410 (6)
C5A—H5A0.9500C5B—H5B0.9500
C6A—C7A1.371 (6)C6B—C7B1.365 (6)
C6A—H6A0.9500C6B—H6B0.9500
C7A—C8A1.418 (6)C7B—C8B1.419 (6)
C7A—H7A0.9500C7B—H7B0.9500
C8A—C9A1.413 (7)C8B—C9B1.421 (5)
C9A—C10A1.373 (7)C9B—C10B1.361 (6)
C9A—H9A0.9500C9B—H9B0.9500
C10A—C11A1.398 (6)C10B—C11B1.410 (5)
C10A—H10A0.9500C10B—H10B0.9500
C11A—C12A1.461 (6)C11B—C12B1.457 (5)
C12A—C13A1.395 (6)C12B—C13B1.399 (5)
C12A—C21A1.406 (6)C12B—C21B1.402 (5)
C13A—C14A1.363 (7)C13B—C14B1.359 (6)
C13A—H13A0.9500C13B—H13B0.9500
C14A—C15A1.421 (7)C14B—C15B1.418 (6)
C14A—H14A0.9500C14B—H14B0.9500
C15A—C16A1.414 (6)C15B—C16B1.421 (7)
C15A—C20A1.428 (5)C15B—C20B1.431 (5)
C16A—C17A1.353 (6)C16B—C17B1.362 (8)
C16A—H16A0.9500C16B—H16B0.9500
C17A—C18A1.398 (6)C17B—C18B1.399 (7)
C17A—H17A0.9500C17B—H17B0.9500
C18A—C19A1.379 (6)C18B—C19B1.368 (7)
C18A—H18A0.9500C18B—H18B0.9500
C19A—C20A1.418 (6)C19B—C20B1.407 (6)
C19A—H19A0.9500C19B—H19B0.9500
C20A—C21A1.443 (5)C20B—C21B1.431 (5)
C22A—C23A1.471 (5)C22B—C23B1.470 (5)
C22A—C42A1.477 (5)C22B—C42B1.489 (5)
C23A—C32A1.389 (5)C23B—C32B1.396 (5)
C23A—C24A1.431 (5)C23B—C24B1.432 (5)
C24A—C25A1.412 (6)C24B—C25B1.414 (5)
C24A—C29A1.431 (6)C24B—C29B1.429 (5)
C25A—C26A1.367 (6)C25B—C26B1.382 (6)
C25A—H25A0.9500C25B—H25B0.9500
C26A—C27A1.407 (6)C26B—C27B1.399 (6)
C26A—H26A0.9500C26B—H26B0.9500
C27A—C28A1.345 (6)C27B—C28B1.349 (7)
C27A—H27A0.9500C27B—H27B0.9500
C28A—C29A1.416 (6)C28B—C29B1.409 (6)
C28A—H28A0.9500C28B—H28B0.9500
C29A—C30A1.416 (6)C29B—C30B1.417 (6)
C30A—C31A1.363 (6)C30B—C31B1.357 (5)
C30A—H30A0.9500C30B—H30B0.9500
C31A—C32A1.404 (5)C31B—C32B1.400 (5)
C31A—H31A0.9500C31B—H31B0.9500
C32A—C33A1.458 (5)C32B—C33B1.450 (6)
C33A—C42A1.400 (5)C33B—C42B1.400 (5)
C33A—C34A1.410 (5)C33B—C34B1.407 (5)
C34A—C35A1.362 (6)C34B—C35B1.368 (5)
C34A—H34A0.9500C34B—H34B0.9500
C35A—C36A1.421 (5)C35B—C36B1.419 (5)
C35A—H35A0.9500C35B—H35B0.9500
C36A—C37A1.419 (5)C36B—C37B1.416 (6)
C36A—C41A1.442 (5)C36B—C41B1.436 (5)
C37A—C38A1.369 (6)C37B—C38B1.361 (6)
C37A—H37A0.9500C37B—H37B0.9500
C38A—C39A1.405 (5)C38B—C39B1.402 (6)
C38A—H38A0.9500C38B—H38B0.9500
C39A—C40A1.371 (5)C39B—C40B1.366 (6)
C39A—H39A0.9500C39B—H39B0.9500
C40A—C41A1.415 (5)C40B—C41B1.417 (5)
C40A—H40A0.9500C40B—H40B0.9500
C41A—C42A1.443 (5)C41B—C42B1.444 (5)
C22A—C1A—C2A125.1 (4)C22B—C1B—C2B126.1 (3)
C22A—C1A—C21A128.3 (4)C22B—C1B—C21B127.8 (4)
C2A—C1A—C21A106.5 (3)C2B—C1B—C21B106.0 (3)
C11A—C2A—C3A119.6 (4)C11B—C2B—C3B119.7 (4)
C11A—C2A—C1A108.5 (4)C11B—C2B—C1B109.0 (3)
C3A—C2A—C1A130.8 (4)C3B—C2B—C1B130.1 (3)
C2A—C3A—C4A125.1 (4)C4B—C3B—C8B117.8 (4)
C2A—C3A—C8A117.6 (4)C4B—C3B—C2B125.2 (4)
C4A—C3A—C8A117.2 (4)C8B—C3B—C2B117.0 (4)
C5A—C4A—C3A121.5 (4)C5B—C4B—C3B121.5 (4)
C5A—C4A—H4A119.2C5B—C4B—H4B119.2
C3A—C4A—H4A119.2C3B—C4B—H4B119.2
C4A—C5A—C6A120.9 (4)C4B—C5B—C6B120.6 (4)
C4A—C5A—H5A119.6C4B—C5B—H5B119.7
C6A—C5A—H5A119.6C6B—C5B—H5B119.7
C7A—C6A—C5A120.0 (4)C7B—C6B—C5B119.5 (4)
C7A—C6A—H6A120.0C7B—C6B—H6B120.2
C5A—C6A—H6A120.0C5B—C6B—H6B120.2
C6A—C7A—C8A120.6 (4)C6B—C7B—C8B121.5 (4)
C6A—C7A—H7A119.7C6B—C7B—H7B119.2
C8A—C7A—H7A119.7C8B—C7B—H7B119.2
C9A—C8A—C7A120.2 (4)C7B—C8B—C9B120.8 (4)
C9A—C8A—C3A120.0 (4)C7B—C8B—C3B118.9 (4)
C7A—C8A—C3A119.8 (4)C9B—C8B—C3B120.2 (4)
C10A—C9A—C8A121.6 (5)C10B—C9B—C8B121.7 (4)
C10A—C9A—H9A119.2C10B—C9B—H9B119.2
C8A—C9A—H9A119.2C8B—C9B—H9B119.2
C9A—C10A—C11A118.1 (5)C9B—C10B—C11B118.3 (4)
C9A—C10A—H10A120.9C9B—C10B—H10B120.8
C11A—C10A—H10A120.9C11B—C10B—H10B120.8
C2A—C11A—C10A122.6 (4)C2B—C11B—C10B122.1 (4)
C2A—C11A—C12A108.5 (4)C2B—C11B—C12B108.3 (3)
C10A—C11A—C12A128.8 (5)C10B—C11B—C12B129.6 (4)
C13A—C12A—C21A122.4 (4)C13B—C12B—C21B122.0 (4)
C13A—C12A—C11A128.5 (4)C13B—C12B—C11B128.3 (4)
C21A—C12A—C11A109.1 (4)C21B—C12B—C11B109.8 (3)
C14A—C13A—C12A119.6 (5)C14B—C13B—C12B119.6 (4)
C14A—C13A—H13A120.2C14B—C13B—H13B120.2
C12A—C13A—H13A120.2C12B—C13B—H13B120.2
C13A—C14A—C15A121.0 (5)C13B—C14B—C15B120.7 (4)
C13A—C14A—H14A119.5C13B—C14B—H14B119.7
C15A—C14A—H14A119.5C15B—C14B—H14B119.7
C16A—C15A—C14A120.3 (4)C14B—C15B—C16B119.8 (4)
C16A—C15A—C20A119.2 (4)C14B—C15B—C20B120.9 (4)
C14A—C15A—C20A120.4 (4)C16B—C15B—C20B119.2 (4)
C17A—C16A—C15A122.3 (4)C17B—C16B—C15B121.6 (5)
C17A—C16A—H16A118.9C17B—C16B—H16B119.2
C15A—C16A—H16A118.9C15B—C16B—H16B119.2
C16A—C17A—C18A119.0 (4)C16B—C17B—C18B118.8 (5)
C16A—C17A—H17A120.5C16B—C17B—H17B120.6
C18A—C17A—H17A120.5C18B—C17B—H17B120.6
C19A—C18A—C17A121.1 (4)C19B—C18B—C17B121.5 (5)
C19A—C18A—H18A119.5C19B—C18B—H18B119.2
C17A—C18A—H18A119.5C17B—C18B—H18B119.2
C18A—C19A—C20A121.2 (4)C18B—C19B—C20B121.5 (5)
C18A—C19A—H19A119.4C18B—C19B—H19B119.3
C20A—C19A—H19A119.4C20B—C19B—H19B119.3
C19A—C20A—C15A117.1 (4)C19B—C20B—C15B117.3 (4)
C19A—C20A—C21A125.0 (4)C19B—C20B—C21B125.5 (4)
C15A—C20A—C21A117.8 (4)C15B—C20B—C21B117.1 (4)
C12A—C21A—C20A118.6 (4)C12B—C21B—C20B119.3 (4)
C12A—C21A—C1A107.2 (4)C12B—C21B—C1B106.8 (3)
C20A—C21A—C1A133.4 (4)C20B—C21B—C1B133.1 (4)
C1A—C22A—C23A126.3 (3)C1B—C22B—C23B125.8 (4)
C1A—C22A—C42A127.8 (3)C1B—C22B—C42B128.4 (4)
C23A—C22A—C42A105.9 (3)C23B—C22B—C42B105.7 (3)
C32A—C23A—C24A119.5 (3)C32B—C23B—C24B119.5 (3)
C32A—C23A—C22A108.6 (3)C32B—C23B—C22B108.9 (3)
C24A—C23A—C22A131.2 (3)C24B—C23B—C22B130.8 (3)
C25A—C24A—C29A118.0 (4)C25B—C24B—C29B117.7 (3)
C25A—C24A—C23A125.0 (4)C25B—C24B—C23B124.9 (3)
C29A—C24A—C23A117.0 (4)C29B—C24B—C23B117.3 (3)
C26A—C25A—C24A121.5 (5)C26B—C25B—C24B121.6 (4)
C26A—C25A—H25A119.3C26B—C25B—H25B119.2
C24A—C25A—H25A119.3C24B—C25B—H25B119.2
C25A—C26A—C27A119.9 (4)C25B—C26B—C27B119.7 (4)
C25A—C26A—H26A120.1C25B—C26B—H26B120.2
C27A—C26A—H26A120.1C27B—C26B—H26B120.2
C28A—C27A—C26A120.4 (4)C28B—C27B—C26B120.0 (4)
C28A—C27A—H27A119.8C28B—C27B—H27B120.0
C26A—C27A—H27A119.8C26B—C27B—H27B120.0
C27A—C28A—C29A121.7 (4)C27B—C28B—C29B122.4 (4)
C27A—C28A—H28A119.2C27B—C28B—H28B118.8
C29A—C28A—H28A119.2C29B—C28B—H28B118.8
C30A—C29A—C28A121.2 (4)C28B—C29B—C30B121.6 (4)
C30A—C29A—C24A120.4 (4)C28B—C29B—C24B118.5 (4)
C28A—C29A—C24A118.4 (4)C30B—C29B—C24B119.9 (4)
C31A—C30A—C29A121.5 (4)C31B—C30B—C29B121.9 (4)
C31A—C30A—H30A119.2C31B—C30B—H30B119.1
C29A—C30A—H30A119.2C29B—C30B—H30B119.1
C30A—C31A—C32A118.3 (4)C30B—C31B—C32B118.9 (4)
C30A—C31A—H31A120.8C30B—C31B—H31B120.5
C32A—C31A—H31A120.8C32B—C31B—H31B120.5
C23A—C32A—C31A122.6 (4)C23B—C32B—C31B121.8 (4)
C23A—C32A—C33A108.8 (3)C23B—C32B—C33B108.4 (3)
C31A—C32A—C33A128.6 (4)C31B—C32B—C33B129.8 (4)
C42A—C33A—C34A123.3 (4)C42B—C33B—C34B122.9 (4)
C42A—C33A—C32A108.6 (3)C42B—C33B—C32B109.5 (3)
C34A—C33A—C32A128.0 (3)C34B—C33B—C32B127.6 (4)
C35A—C34A—C33A118.4 (3)C35B—C34B—C33B118.8 (4)
C35A—C34A—H34A120.8C35B—C34B—H34B120.6
C33A—C34A—H34A120.8C33B—C34B—H34B120.6
C34A—C35A—C36A121.3 (4)C34B—C35B—C36B121.0 (4)
C34A—C35A—H35A119.4C34B—C35B—H35B119.5
C36A—C35A—H35A119.4C36B—C35B—H35B119.5
C37A—C36A—C35A119.5 (4)C37B—C36B—C35B120.0 (4)
C37A—C36A—C41A119.4 (4)C37B—C36B—C41B119.0 (4)
C35A—C36A—C41A121.0 (4)C35B—C36B—C41B121.0 (4)
C38A—C37A—C36A121.3 (4)C38B—C37B—C36B122.0 (4)
C38A—C37A—H37A119.3C38B—C37B—H37B119.0
C36A—C37A—H37A119.3C36B—C37B—H37B119.0
C37A—C38A—C39A119.2 (4)C37B—C38B—C39B118.8 (4)
C37A—C38A—H38A120.4C37B—C38B—H38B120.6
C39A—C38A—H38A120.4C39B—C38B—H38B120.6
C40A—C39A—C38A121.3 (4)C40B—C39B—C38B121.7 (4)
C40A—C39A—H39A119.3C40B—C39B—H39B119.1
C38A—C39A—H39A119.3C38B—C39B—H39B119.1
C39A—C40A—C41A121.5 (4)C39B—C40B—C41B121.1 (4)
C39A—C40A—H40A119.3C39B—C40B—H40B119.5
C41A—C40A—H40A119.3C41B—C40B—H40B119.5
C40A—C41A—C36A117.2 (3)C40B—C41B—C36B117.4 (3)
C40A—C41A—C42A125.8 (3)C40B—C41B—C42B125.3 (3)
C36A—C41A—C42A116.9 (3)C36B—C41B—C42B117.2 (3)
C33A—C42A—C41A118.7 (3)C33B—C42B—C41B118.7 (3)
C33A—C42A—C22A108.0 (3)C33B—C42B—C22B107.5 (3)
C41A—C42A—C22A132.2 (3)C41B—C42B—C22B132.8 (3)
C22A—C1A—C2A—C11A172.4 (3)C22B—C1B—C2B—C11B174.9 (4)
C21A—C1A—C2A—C11A4.0 (4)C21B—C1B—C2B—C11B3.4 (4)
C22A—C1A—C2A—C3A20.4 (6)C22B—C1B—C2B—C3B17.9 (6)
C21A—C1A—C2A—C3A163.2 (4)C21B—C1B—C2B—C3B163.8 (4)
C11A—C2A—C3A—C4A168.4 (4)C11B—C2B—C3B—C4B165.3 (4)
C1A—C2A—C3A—C4A2.3 (7)C1B—C2B—C3B—C4B0.8 (6)
C11A—C2A—C3A—C8A7.3 (6)C11B—C2B—C3B—C8B10.9 (5)
C1A—C2A—C3A—C8A173.4 (4)C1B—C2B—C3B—C8B176.9 (4)
C2A—C3A—C4A—C5A177.7 (4)C8B—C3B—C4B—C5B0.8 (6)
C8A—C3A—C4A—C5A2.0 (6)C2B—C3B—C4B—C5B176.9 (4)
C3A—C4A—C5A—C6A0.2 (6)C3B—C4B—C5B—C6B1.8 (6)
C4A—C5A—C6A—C7A0.5 (6)C4B—C5B—C6B—C7B1.5 (7)
C5A—C6A—C7A—C8A0.7 (7)C5B—C6B—C7B—C8B1.4 (7)
C6A—C7A—C8A—C9A174.8 (4)C6B—C7B—C8B—C9B172.7 (4)
C6A—C7A—C8A—C3A2.5 (7)C6B—C7B—C8B—C3B4.0 (6)
C2A—C3A—C8A—C9A1.8 (6)C4B—C3B—C8B—C7B3.6 (6)
C4A—C3A—C8A—C9A174.2 (4)C2B—C3B—C8B—C7B179.9 (4)
C2A—C3A—C8A—C7A179.1 (4)C4B—C3B—C8B—C9B173.1 (4)
C4A—C3A—C8A—C7A3.1 (6)C2B—C3B—C8B—C9B3.4 (5)
C7A—C8A—C9A—C10A173.4 (5)C7B—C8B—C9B—C10B172.3 (4)
C3A—C8A—C9A—C10A3.9 (7)C3B—C8B—C9B—C10B4.3 (6)
C8A—C9A—C10A—C11A3.9 (7)C8B—C9B—C10B—C11B4.3 (7)
C3A—C2A—C11A—C10A7.6 (6)C3B—C2B—C11B—C10B11.3 (6)
C1A—C2A—C11A—C10A176.5 (4)C1B—C2B—C11B—C10B180.0 (4)
C3A—C2A—C11A—C12A168.2 (4)C3B—C2B—C11B—C12B167.0 (3)
C1A—C2A—C11A—C12A0.7 (4)C1B—C2B—C11B—C12B1.8 (4)
C9A—C10A—C11A—C2A1.9 (6)C9B—C10B—C11B—C2B3.5 (6)
C9A—C10A—C11A—C12A173.0 (4)C9B—C10B—C11B—C12B174.3 (4)
C2A—C11A—C12A—C13A175.7 (4)C2B—C11B—C12B—C13B179.1 (4)
C10A—C11A—C12A—C13A8.8 (7)C10B—C11B—C12B—C13B2.8 (7)
C2A—C11A—C12A—C21A3.1 (5)C2B—C11B—C12B—C21B0.6 (5)
C10A—C11A—C12A—C21A172.3 (4)C10B—C11B—C12B—C21B177.4 (4)
C21A—C12A—C13A—C14A0.5 (7)C21B—C12B—C13B—C14B0.6 (7)
C11A—C12A—C13A—C14A179.2 (4)C11B—C12B—C13B—C14B179.2 (4)
C12A—C13A—C14A—C15A1.6 (7)C12B—C13B—C14B—C15B3.3 (7)
C13A—C14A—C15A—C16A178.5 (4)C13B—C14B—C15B—C16B175.3 (5)
C13A—C14A—C15A—C20A0.3 (7)C13B—C14B—C15B—C20B1.4 (7)
C14A—C15A—C16A—C17A175.2 (4)C14B—C15B—C16B—C17B175.5 (5)
C20A—C15A—C16A—C17A2.9 (7)C20B—C15B—C16B—C17B1.3 (7)
C15A—C16A—C17A—C18A0.2 (7)C15B—C16B—C17B—C18B0.5 (7)
C16A—C17A—C18A—C19A1.7 (7)C16B—C17B—C18B—C19B0.8 (6)
C17A—C18A—C19A—C20A0.0 (6)C17B—C18B—C19B—C20B0.7 (6)
C18A—C19A—C20A—C15A3.1 (6)C18B—C19B—C20B—C15B2.5 (6)
C18A—C19A—C20A—C21A179.8 (4)C18B—C19B—C20B—C21B179.6 (4)
C16A—C15A—C20A—C19A4.5 (6)C14B—C15B—C20B—C19B174.0 (4)
C14A—C15A—C20A—C19A173.7 (4)C16B—C15B—C20B—C19B2.7 (6)
C16A—C15A—C20A—C21A178.6 (4)C14B—C15B—C20B—C21B4.0 (6)
C14A—C15A—C20A—C21A3.3 (6)C16B—C15B—C20B—C21B179.2 (4)
C13A—C12A—C21A—C20A2.5 (6)C13B—C12B—C21B—C20B6.2 (6)
C11A—C12A—C21A—C20A176.4 (3)C11B—C12B—C21B—C20B173.6 (3)
C13A—C12A—C21A—C1A173.4 (4)C13B—C12B—C21B—C1B177.0 (4)
C11A—C12A—C21A—C1A5.6 (4)C11B—C12B—C21B—C1B2.8 (4)
C19A—C20A—C21A—C12A172.4 (4)C19B—C20B—C21B—C12B170.2 (4)
C15A—C20A—C21A—C12A4.3 (5)C15B—C20B—C21B—C12B7.7 (6)
C19A—C20A—C21A—C1A4.5 (7)C19B—C20B—C21B—C1B2.3 (7)
C15A—C20A—C21A—C1A172.2 (4)C15B—C20B—C21B—C1B175.6 (4)
C22A—C1A—C21A—C12A170.4 (4)C22B—C1B—C21B—C12B174.5 (4)
C2A—C1A—C21A—C12A5.9 (4)C2B—C1B—C21B—C12B3.8 (4)
C22A—C1A—C21A—C20A1.5 (7)C22B—C1B—C21B—C20B5.5 (7)
C2A—C1A—C21A—C20A174.8 (4)C2B—C1B—C21B—C20B172.8 (4)
C2A—C1A—C22A—C23A131.8 (4)C2B—C1B—C22B—C23B134.6 (4)
C21A—C1A—C22A—C23A52.6 (6)C21B—C1B—C22B—C23B47.4 (6)
C2A—C1A—C22A—C42A48.7 (6)C2B—C1B—C22B—C42B50.0 (6)
C21A—C1A—C22A—C42A127.0 (4)C21B—C1B—C22B—C42B128.0 (4)
C1A—C22A—C23A—C32A178.2 (4)C1B—C22B—C23B—C32B174.4 (4)
C42A—C22A—C23A—C32A1.4 (4)C42B—C22B—C23B—C32B1.8 (4)
C1A—C22A—C23A—C24A11.9 (6)C1B—C22B—C23B—C24B15.6 (7)
C42A—C22A—C23A—C24A168.5 (4)C42B—C22B—C23B—C24B168.1 (4)
C32A—C23A—C24A—C25A169.8 (4)C32B—C23B—C24B—C25B169.6 (4)
C22A—C23A—C24A—C25A0.9 (7)C22B—C23B—C24B—C25B0.5 (6)
C32A—C23A—C24A—C29A8.8 (5)C32B—C23B—C24B—C29B8.7 (5)
C22A—C23A—C24A—C29A177.7 (4)C22B—C23B—C24B—C29B177.8 (4)
C29A—C24A—C25A—C26A4.0 (6)C29B—C24B—C25B—C26B2.6 (6)
C23A—C24A—C25A—C26A177.4 (4)C23B—C24B—C25B—C26B179.1 (4)
C24A—C25A—C26A—C27A0.3 (7)C24B—C25B—C26B—C27B0.5 (6)
C25A—C26A—C27A—C28A3.8 (7)C25B—C26B—C27B—C28B3.3 (7)
C26A—C27A—C28A—C29A2.8 (7)C26B—C27B—C28B—C29B2.8 (7)
C27A—C28A—C29A—C30A178.8 (4)C27B—C28B—C29B—C30B178.1 (4)
C27A—C28A—C29A—C24A1.6 (6)C27B—C28B—C29B—C24B0.5 (7)
C25A—C24A—C29A—C30A175.5 (4)C25B—C24B—C29B—C28B3.1 (6)
C23A—C24A—C29A—C30A3.1 (6)C23B—C24B—C29B—C28B178.5 (4)
C25A—C24A—C29A—C28A5.0 (6)C25B—C24B—C29B—C30B175.5 (4)
C23A—C24A—C29A—C28A176.4 (3)C23B—C24B—C29B—C30B2.9 (5)
C28A—C29A—C30A—C31A177.7 (4)C28B—C29B—C30B—C31B175.9 (4)
C24A—C29A—C30A—C31A2.8 (7)C24B—C29B—C30B—C31B2.7 (6)
C29A—C30A—C31A—C32A3.1 (6)C29B—C30B—C31B—C32B2.4 (6)
C24A—C23A—C32A—C31A9.0 (6)C24B—C23B—C32B—C31B9.3 (6)
C22A—C23A—C32A—C31A179.8 (3)C22B—C23B—C32B—C31B179.4 (4)
C24A—C23A—C32A—C33A170.5 (3)C24B—C23B—C32B—C33B170.7 (3)
C22A—C23A—C32A—C33A0.7 (4)C22B—C23B—C32B—C33B0.6 (4)
C30A—C31A—C32A—C23A2.9 (6)C30B—C31B—C32B—C23B3.7 (6)
C30A—C31A—C32A—C33A176.5 (4)C30B—C31B—C32B—C33B176.3 (4)
C23A—C32A—C33A—C42A0.3 (4)C23B—C32B—C33B—C42B0.9 (5)
C31A—C32A—C33A—C42A179.2 (4)C31B—C32B—C33B—C42B179.1 (4)
C23A—C32A—C33A—C34A177.1 (4)C23B—C32B—C33B—C34B178.2 (4)
C31A—C32A—C33A—C34A3.4 (7)C31B—C32B—C33B—C34B1.8 (7)
C42A—C33A—C34A—C35A2.8 (6)C42B—C33B—C34B—C35B3.6 (6)
C32A—C33A—C34A—C35A174.3 (4)C32B—C33B—C34B—C35B175.4 (4)
C33A—C34A—C35A—C36A2.2 (6)C33B—C34B—C35B—C36B1.8 (6)
C34A—C35A—C36A—C37A174.9 (4)C34B—C35B—C36B—C37B174.9 (4)
C34A—C35A—C36A—C41A2.8 (6)C34B—C35B—C36B—C41B3.0 (6)
C35A—C36A—C37A—C38A177.2 (4)C35B—C36B—C37B—C38B178.3 (4)
C41A—C36A—C37A—C38A0.6 (6)C41B—C36B—C37B—C38B0.4 (6)
C36A—C37A—C38A—C39A0.1 (6)C36B—C37B—C38B—C39B1.5 (6)
C37A—C38A—C39A—C40A0.1 (6)C37B—C38B—C39B—C40B1.6 (6)
C38A—C39A—C40A—C41A0.7 (6)C38B—C39B—C40B—C41B0.5 (6)
C39A—C40A—C41A—C36A1.4 (6)C39B—C40B—C41B—C36B0.7 (6)
C39A—C40A—C41A—C42A179.0 (4)C39B—C40B—C41B—C42B178.6 (4)
C37A—C36A—C41A—C40A1.3 (5)C37B—C36B—C41B—C40B0.7 (5)
C35A—C36A—C41A—C40A176.4 (4)C35B—C36B—C41B—C40B177.1 (3)
C37A—C36A—C41A—C42A179.1 (3)C37B—C36B—C41B—C42B178.8 (3)
C35A—C36A—C41A—C42A1.4 (5)C35B—C36B—C41B—C42B1.0 (5)
C34A—C33A—C42A—C41A7.0 (6)C34B—C33B—C42B—C41B7.5 (6)
C32A—C33A—C42A—C41A170.6 (3)C32B—C33B—C42B—C41B171.6 (3)
C34A—C33A—C42A—C22A176.4 (4)C34B—C33B—C42B—C22B177.1 (4)
C32A—C33A—C42A—C22A1.2 (4)C32B—C33B—C42B—C22B2.1 (4)
C40A—C41A—C42A—C33A171.6 (4)C40B—C41B—C42B—C33B172.0 (4)
C36A—C41A—C42A—C33A6.0 (5)C36B—C41B—C42B—C33B6.0 (5)
C40A—C41A—C42A—C22A5.3 (7)C40B—C41B—C42B—C22B5.6 (7)
C36A—C41A—C42A—C22A172.3 (4)C36B—C41B—C42B—C22B172.4 (4)
C1A—C22A—C42A—C33A178.0 (4)C1B—C22B—C42B—C33B173.8 (4)
C23A—C22A—C42A—C33A1.6 (4)C23B—C22B—C42B—C33B2.4 (4)
C1A—C22A—C42A—C41A10.6 (7)C1B—C22B—C42B—C41B6.3 (7)
C23A—C22A—C42A—C41A169.0 (4)C23B—C22B—C42B—C41B169.9 (4)
 

Acknowledgements

The authors are grateful to Professor D. Lenoir for invaluable discussions and to Professor M. Baumgarten for measuring the ESR spectrum.

References

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