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The title compound, C29H42, crystallizes from the melt as a triclinic crystal. The unit cell contains three crystallographically independent mol­ecules. The three fluorene ring systems are oriented such that two non-equivalent ring systems related by a roto-translation are separated by a third ring system oriented orthogonally to them. The octyl chains of all three mol­ecules are perpendicular to the fluorene ring system and force a 7.4 Å separation between the two coplanar mol­ecules, thereby preventing mol­ecular π-stacking.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270105032786/gz1016sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270105032786/gz1016Isup2.hkl
Contains datablock I

CCDC reference: 294320

Comment top

The semiconducting polymer poly(9,9-di-n-octyl-2,7-fluorene) (PFO) is currently being investigated scientifically and industrially as a blue light-emitting material for polymer light-emitting diodes (PLEDs) (Scherf & List, 2002). The photophysical properties of PFO are complex and strongly dependent on the processing conditions of the material (Grell et al., 1999). It is known that subtle changes in processing conditions produce dramatic structural and photophysical changes (Grell et al., 1999). To add to the complexity, PFO chains are believed to order concomitantly in numerous phases, i.e. crystalline, liquid crystalline (Scherf & List, 2002) and noncrystalline (Chen et al., 2005) in the solid state. In order to achieve a better understanding of PFO-based optoelectronic devices, and ultimately to control their electroluminescence maximum, researchers have been investigating correlations between polymer morphology and photophysical properties (Chen et al., 2005). To illustrate the complex emission characteristics of PFO, researchers have examined the photophysics of PFO as single polymer chains (Grell et al., 1999; Becker & Lupton, 2005) and found that small conformational changes can significantly alter the emission characteristics (Becker & Lupton, 2005). It has been proposed (Grell et al., 1999) that PFO adopts a `planar zigzag' conformation, in which the octyl chains on adjacent fluorene units are oriented antiparallel to each other, upon prolonged exposure to certain solvents. In light of the numerous conformations and phases that PFO polymer chains can adopt, a variety of packing models are necessary to understand fully its complex solid-state photophysics.

The crystal structures of 2,7-dibromo-9.9-dioctylfluorene–chloroform (Leclerc et al., 1998) and 2,2'-bi(9,9-dihexylfluorene) (Suchod & Stéphan, 2000) analogues have been used to explain the chain packing, and hence the electro-optical properties, of PFO. The solid-state structures of both these monomers and of the present structure show that alkyl-substitutent steric requirements at the 9-position of the fluorene ring system effectively eliminate π-stacking. Unfortunately, while comparisons of these small-molecule structures provide some limited insight into the PFO structure, both have inherent limitations. The inclusion of a single solvent CHCl3 molecule in the tetragonal unit cell and the Br atoms of 2,7-dibromo-9.9-dioctylfluorene–chloroform limit a direct PFO comparison, yet it has been used to model structural phases (Ariu et al., 2001). While the crystal structure of 2,2'-bi(9,9-dihexylfluorene) (Suchod & Stéphan, 2000) possesses greater structural similarity with PFO and there is no inclusion of solvent, it crystallizes in a monoclinic space group inconsistent with the proposed packing of PFO (Grell et al., 1999).

To understand further the structure–photophysical relationships of PFO, we have determined the solid-state crystal structure of the title compound, (I). The compound crystallizes from the melt, thus eliminating influences from solvent/monomer interactions on the final structure. A molecular drawing of one of the three crystallographically independent molecules of the title compound is shown in Fig. 1. As is the case for the other aforementioned small molecule PFO models, all three non-equivalent molecules, A, B and C, in the present triclinic structure possess a planar central fluorene ring [none of the fluorene ring C atoms deviates from the calculated planes by more than 0.035 (2) Å]. In each molecule, the octyl chains extend in a direction orthogonal to the aromatic ring system; only molecule C shows any deviation from this planar zigzag conformation, with a 50% disorder of one of its terminal octyl C-atom positions. Fig. 2 illustrates the relative orientations of the adjacent independent molecules. The planes of the fluorene rings of molecules A and B are nearly parallel [the dihedral angle between their fluorene planes is 2.59 (5)°], while the fluorene plane of molecule C is almost orthogonal to those of molecules A and B [AC and BC dihedral plane angles are 88.64 (4)° and 89.22 (3)°, respectively]. Fig. 3 shows the crystal packing as viewed down the b axis.

Our crystallization process is similar to common processing conditions used in the fabrication of PFO-based PLEDs (Chen et al., 2005) and, by extension, we expect that the molecular ordering presented here may provide a more accurate approximation of the PFO chain packing in functional PLEDs. Furthermore, the crystals display a blue luminescence (λem = 333 nm; λex = 266 nm) consistent with the photo- and electroluminescence of PFO. We expect this triclinic crystal structure to provide valuable insight into the photophysics of PFO (Chen et al., 2005).

Experimental top

The title compound was prepared according to the previously published procedure of Ranger et al. (1997), followed by additional purification. To obtain suitable single crystals, the material was further purified by column chromatography (silica gel, hexane). The hexane was removed under reduced pressure and the resulting white cloudy oil was rapidly cooled to 195 K and allowed to warm slowly to room temperature, yielding colourless plate-like [Prism below?] crystals. The melting point of the resulting crystals was 300–301 K, as determined by differential scanning calorimetry.

Refinement top

Disorder of one of the terminal C atoms of one octyl chain of one of the molecules was handled by splitting this atom into two equally occupied positions (C29C and C29D). The bond lengths and 1,3-distances involving these atoms were assigned fixed idealized values (C28C—C29C = C28C—C29D = 1.51 Å; C27C···C29C = C27C···C29D = 2.53 Å). Another n-octyl terminal atom (C21C) was also found to have a large Ueq [0.203 (3) Å2], but it could not be successfully split into two well behaved partial-occupancy positions; the bond distance [C20C—C21C 1.497 (5) Å2] and angle [C19C—C20C—C21C 112.6 (3)°] involving this C atom are nonetheless acceptable. H atoms were generated in idealized positions, with C—H distances in the range 0.95–0.99 Å, and with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2003); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. A drawing of one of the three crystallographically independent molecules of (I). Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. Illustration of the relative orientations of the three molecules of (I) as they occur in the unit cell.
[Figure 3] Fig. 3. Illustration of the crystal packing of (I). The view direction is approximately along the crystallographic b axis.
9,9-di-n-octyl-9H-fluorene top
Crystal data top
C29H42Z = 6
Mr = 390.63F(000) = 1296
Triclinic, P1Dx = 1.014 Mg m3
Hall symbol: -P 1Melting point: 300 K
a = 13.9223 (18) ÅMo Kα radiation, λ = 0.71073 Å
b = 14.2423 (18) ÅCell parameters from 7045 reflections
c = 21.570 (3) Åθ = 2.2–25.9°
α = 83.079 (2)°µ = 0.06 mm1
β = 72.024 (2)°T = 193 K
γ = 70.605 (2)°Prism, colourless
V = 3836.6 (9) Å30.36 × 0.35 × 0.26 mm
Data collection top
Bruker SMART 1000 CCD area-detector/PLATFORM
diffractometer
13469 independent reflections
Radiation source: fine-focus sealed tube8216 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
Detector resolution: 8.192 pixels mm-1θmax = 25.0°, θmin = 1.0°
ω scansh = 1616
Absorption correction: integration
(SHELXTL; Bruker, 2003)
k = 1616
Tmin = 0.829, Tmax = 0.986l = 2525
25454 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.060H-atom parameters constrained
wR(F2) = 0.190 w = 1/[σ2(Fo2) + (0.0922P)2 + 0.6911P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
13469 reflectionsΔρmax = 0.54 e Å3
796 parametersΔρmin = 0.19 e Å3
4 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0092 (8)
Crystal data top
C29H42γ = 70.605 (2)°
Mr = 390.63V = 3836.6 (9) Å3
Triclinic, P1Z = 6
a = 13.9223 (18) ÅMo Kα radiation
b = 14.2423 (18) ŵ = 0.06 mm1
c = 21.570 (3) ÅT = 193 K
α = 83.079 (2)°0.36 × 0.35 × 0.26 mm
β = 72.024 (2)°
Data collection top
Bruker SMART 1000 CCD area-detector/PLATFORM
diffractometer
13469 independent reflections
Absorption correction: integration
(SHELXTL; Bruker, 2003)
8216 reflections with I > 2σ(I)
Tmin = 0.829, Tmax = 0.986Rint = 0.036
25454 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0604 restraints
wR(F2) = 0.190H-atom parameters constrained
S = 1.03Δρmax = 0.54 e Å3
13469 reflectionsΔρmin = 0.19 e Å3
796 parameters
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Disorder of one of the terminal carbons of one octyl chain of one of the molecules was handled by splitting this atom into two equally abundant positions (C29C and C29D). The bond lengths and 1,3-distances involving these atoms were assigned fixed idealized values (C28C—C29C = C28C—C29D = 1.51 Å; C27C···C29C = C27C···C29D = 2.53 Å).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C1A0.11109 (17)0.02678 (15)0.29562 (10)0.0429 (5)
C2A0.19629 (17)0.01673 (15)0.32850 (11)0.0439 (5)
C3A0.30554 (19)0.01818 (16)0.30326 (14)0.0577 (7)
H3A0.33720.03970.25950.069*
C4A0.3687 (2)0.02122 (19)0.34337 (19)0.0750 (9)
H4A0.44390.04500.32680.090*
C5A0.3223 (3)0.0101 (2)0.40640 (19)0.0816 (10)
H5A0.36640.00800.43280.098*
C6A0.2143 (3)0.04411 (18)0.43238 (15)0.0697 (8)
H6A0.18340.06490.47630.084*
C7A0.1507 (2)0.04764 (15)0.39309 (12)0.0510 (6)
C8A0.0352 (2)0.08206 (15)0.40678 (12)0.0531 (6)
C9A0.0463 (3)0.12138 (18)0.46238 (14)0.0778 (9)
H9A0.03030.12780.50110.093*
C10A0.1496 (3)0.1506 (2)0.4609 (2)0.0975 (13)
H10A0.20510.17800.49870.117*
C11A0.1742 (2)0.1410 (2)0.4056 (2)0.0910 (12)
H11A0.24650.16170.40560.109*
C12A0.09450 (19)0.10130 (17)0.34946 (15)0.0665 (8)
H12A0.11180.09470.31120.080*
C13A0.01069 (17)0.07147 (15)0.35036 (12)0.0478 (6)
C14A0.11599 (18)0.07528 (15)0.27555 (11)0.0473 (5)
H14A0.05330.06610.26020.057*
H14B0.18000.09860.23810.057*
C15A0.11905 (18)0.15662 (15)0.32806 (11)0.0455 (5)
H15A0.05590.13370.36610.055*
H15B0.18300.16830.34260.055*
C16A0.12084 (18)0.25408 (15)0.30506 (11)0.0460 (5)
H16A0.05280.24410.29570.055*
H16B0.17860.27250.26390.055*
C17A0.13721 (18)0.33936 (15)0.35409 (11)0.0468 (5)
H17A0.08270.31870.39630.056*
H17B0.20760.35240.36090.056*
C18A0.13123 (19)0.43546 (16)0.33424 (11)0.0489 (6)
H18A0.06380.42130.32320.059*
H18B0.19040.46000.29450.059*
C19A0.13705 (18)0.51679 (15)0.38650 (11)0.0473 (6)
H19A0.20740.53530.39440.057*
H19B0.08250.48980.42750.057*
C20A0.12080 (19)0.60980 (16)0.37039 (12)0.0532 (6)
H20A0.05480.59070.35700.064*
H20B0.18080.64220.33290.064*
C21A0.1131 (2)0.68387 (18)0.42666 (14)0.0674 (7)
H21A0.10530.74330.41280.081*
H21B0.05130.65370.46310.081*
H21C0.17780.70260.44060.081*
C22A0.12055 (19)0.09582 (16)0.23486 (11)0.0506 (6)
H22A0.18830.06410.20190.061*
H22B0.06220.10070.21630.061*
C23A0.11698 (19)0.20043 (16)0.24530 (11)0.0501 (6)
H23A0.17370.19660.26500.060*
H23B0.04780.23430.27640.060*
C24A0.13133 (19)0.26222 (17)0.18239 (11)0.0521 (6)
H24A0.19930.22710.15080.063*
H24B0.07330.26770.16340.063*
C25A0.1314 (2)0.36584 (17)0.19162 (12)0.0563 (6)
H25A0.06220.40160.22190.068*
H25B0.18740.36020.21240.068*
C26A0.1500 (2)0.42737 (19)0.12942 (13)0.0645 (7)
H26A0.22100.39360.10010.077*
H26B0.09650.42990.10730.077*
C27A0.1439 (2)0.53215 (18)0.13946 (12)0.0599 (7)
H27A0.07330.56490.16960.072*
H27B0.19800.52910.16110.072*
C28A0.1599 (3)0.5957 (2)0.07961 (15)0.0866 (10)
H28A0.10750.59650.05700.104*
H28B0.23150.56420.05020.104*
C29A0.1498 (3)0.7011 (2)0.08950 (16)0.0880 (10)
H29A0.16030.73650.04730.106*
H29B0.20370.70200.10960.106*
H29C0.07890.73400.11800.106*
C1B0.77206 (17)0.34849 (16)0.14914 (11)0.0458 (5)
C2B0.74752 (18)0.37246 (16)0.22015 (11)0.0471 (6)
C3B0.8174 (2)0.36191 (18)0.25593 (12)0.0571 (6)
H3B0.89190.33720.23610.069*
C4B0.7781 (3)0.3875 (2)0.32090 (13)0.0698 (8)
H4B0.82600.38030.34570.084*
C5B0.6706 (3)0.4233 (2)0.34986 (14)0.0752 (8)
H5B0.64500.44110.39440.090*
C6B0.5995 (2)0.43371 (18)0.31535 (13)0.0675 (8)
H6B0.52510.45810.33570.081*
C7B0.63869 (19)0.40777 (16)0.24989 (12)0.0510 (6)
C8B0.58411 (18)0.40905 (16)0.20193 (13)0.0541 (6)
C9B0.4762 (2)0.4372 (2)0.20738 (18)0.0763 (8)
H9B0.42450.46010.24750.092*
C10B0.4462 (2)0.4312 (2)0.1539 (2)0.0876 (10)
H10B0.37260.45030.15720.105*
C11B0.5193 (3)0.3983 (2)0.09550 (18)0.0849 (9)
H11B0.49580.39550.05900.102*
C12B0.6290 (2)0.3687 (2)0.08912 (15)0.0698 (7)
H12B0.68010.34500.04890.084*
C13B0.66015 (18)0.37502 (17)0.14287 (12)0.0515 (6)
C14B0.83638 (18)0.41298 (17)0.10359 (11)0.0496 (6)
H14C0.90180.40210.11640.060*
H14D0.85860.38910.05850.060*
C15B0.77887 (18)0.52423 (17)0.10331 (12)0.0547 (6)
H15C0.74880.54730.14880.066*
H15D0.71900.53660.08470.066*
C16B0.85029 (19)0.58465 (17)0.06448 (12)0.0554 (6)
H16C0.90640.57690.08560.066*
H16D0.88570.55700.02020.066*
C17B0.7929 (2)0.69422 (18)0.05835 (13)0.0624 (7)
H17C0.75730.72170.10260.075*
H17D0.73680.70180.03720.075*
C18B0.8631 (2)0.75495 (18)0.01996 (14)0.0655 (7)
H18C0.91820.74850.04160.079*
H18D0.89980.72660.02400.079*
C19B0.8053 (2)0.8641 (2)0.01269 (16)0.0820 (9)
H19C0.75010.87040.00890.098*
H19D0.76860.89230.05670.098*
C20B0.8750 (3)0.9250 (2)0.0257 (2)0.1121 (13)
H20C0.93010.91870.00400.135*
H20D0.91180.89660.06960.135*
C21B0.8174 (4)1.0337 (3)0.0331 (3)0.161 (2)
H21D0.86861.06790.05750.193*
H21E0.78081.06290.01010.193*
H21F0.76521.04120.05660.193*
C22B0.83596 (18)0.23778 (16)0.13567 (12)0.0511 (6)
H22C0.84890.22570.08910.061*
H22D0.90600.22460.14310.061*
C23B0.7839 (2)0.16440 (18)0.17648 (14)0.0633 (7)
H23C0.76660.17900.22310.076*
H23D0.71610.17420.16680.076*
C24B0.8507 (2)0.05747 (18)0.16552 (14)0.0673 (7)
H24C0.91610.04590.17840.081*
H24D0.87200.04340.11850.081*
C25B0.7908 (2)0.0150 (2)0.20488 (17)0.0823 (9)
H25C0.76610.00180.25160.099*
H25D0.72720.00530.19040.099*
C26B0.8554 (2)0.1198 (2)0.19789 (16)0.0827 (9)
H26C0.91660.13000.21490.099*
H26D0.88390.13520.15090.099*
C27B0.7964 (2)0.1930 (2)0.23278 (14)0.0754 (8)
H27C0.76410.17620.27940.090*
H27D0.73840.18730.21370.090*
C28B0.8697 (2)0.2972 (2)0.22681 (15)0.0799 (8)
H28C0.89970.31360.18000.096*
H28D0.92940.30080.24360.096*
C29B0.8208 (3)0.3730 (2)0.26139 (16)0.0876 (9)
H29D0.87410.43900.25430.105*
H29E0.76200.37090.24480.105*
H29F0.79360.35950.30820.105*
C1C0.43477 (15)0.27197 (15)0.50477 (10)0.0402 (5)
C2C0.35645 (16)0.37678 (15)0.50746 (10)0.0398 (5)
C3C0.37601 (17)0.46531 (16)0.48355 (10)0.0441 (5)
H3C0.44620.46580.46080.053*
C4C0.29220 (19)0.55305 (17)0.49316 (11)0.0503 (6)
H4C0.30510.61400.47660.060*
C5C0.18979 (18)0.55345 (17)0.52656 (12)0.0517 (6)
H5C0.13330.61450.53330.062*
C6C0.16946 (17)0.46509 (16)0.55018 (11)0.0485 (6)
H6C0.09920.46500.57290.058*
C7C0.25285 (16)0.37682 (15)0.54024 (10)0.0407 (5)
C8C0.25513 (16)0.27355 (15)0.55933 (10)0.0418 (5)
C9C0.17352 (18)0.23371 (18)0.59067 (12)0.0529 (6)
H9C0.10190.27560.60370.063*
C10C0.1981 (2)0.13250 (18)0.60263 (12)0.0573 (6)
H10C0.14300.10430.62380.069*
C11C0.3025 (2)0.07178 (18)0.58407 (12)0.0558 (6)
H11C0.31850.00230.59320.067*
C12C0.38379 (18)0.11083 (16)0.55236 (11)0.0498 (6)
H12C0.45530.06850.53950.060*
C13C0.36028 (16)0.21212 (15)0.53944 (10)0.0405 (5)
C14C0.51553 (16)0.26575 (16)0.54200 (11)0.0450 (5)
H14E0.56800.19820.53680.054*
H14F0.55440.31370.52160.054*
C15C0.46738 (17)0.28686 (17)0.61437 (11)0.0481 (6)
H15E0.41040.35180.61990.058*
H15F0.43420.23510.63560.058*
C16C0.54650 (17)0.28937 (16)0.64890 (11)0.0474 (6)
H16E0.60960.22950.63740.057*
H16F0.57020.34850.63330.057*
C17C0.50029 (18)0.29298 (18)0.72226 (11)0.0532 (6)
H17E0.43910.35450.73350.064*
H17F0.47300.23570.73730.064*
C18C0.57766 (19)0.29062 (19)0.75883 (12)0.0598 (7)
H18E0.60320.34910.74520.072*
H18F0.63990.23010.74690.072*
C19C0.5295 (2)0.2912 (3)0.83232 (14)0.0857 (9)
H19E0.47260.35550.84420.103*
H19F0.49570.23790.84480.103*
C20C0.6034 (3)0.2772 (3)0.87070 (17)0.1130 (13)
H20E0.63490.33220.86030.136*
H20F0.66180.21410.85830.136*
C21C0.5510 (4)0.2746 (5)0.94252 (18)0.203 (3)
H21G0.60290.26800.96610.244*
H21H0.52360.21770.95350.244*
H21I0.49210.33640.95500.244*
C22C0.49549 (16)0.23736 (16)0.43459 (11)0.0450 (5)
H22E0.54390.27740.41480.054*
H22F0.54010.16710.43630.054*
C23C0.42715 (17)0.24482 (17)0.39006 (11)0.0479 (6)
H23E0.37280.21170.41180.057*
H23F0.38950.31590.38330.057*
C24C0.49008 (17)0.19825 (18)0.32422 (11)0.0506 (6)
H24E0.54510.23080.30280.061*
H24F0.52700.12700.33100.061*
C25C0.42334 (18)0.20635 (18)0.27907 (11)0.0509 (6)
H25E0.39010.27760.26980.061*
H25F0.36550.17760.30140.061*
C26C0.4864 (2)0.1539 (2)0.21520 (12)0.0669 (7)
H26E0.52170.08330.22480.080*
H26F0.54280.18420.19250.080*
C27C0.4215 (2)0.1574 (2)0.16941 (12)0.0725 (8)
H27E0.38980.22760.15710.087*
H27F0.36270.13030.19240.087*
C28C0.4883 (3)0.0982 (3)0.10773 (15)0.1293 (17)
H28E0.54310.12920.08280.155*0.50
H28F0.52520.02960.12020.155*0.50
H28G0.45300.12350.07290.155*0.50
H28H0.55860.10900.09290.155*0.50
C29C0.4229 (5)0.0935 (8)0.0646 (3)0.170 (5)0.50
H29G0.45580.11210.01970.204*0.50
H29H0.35080.13980.08030.204*0.50
H29I0.41950.02570.06570.204*0.50
C29D0.5039 (7)0.0120 (3)0.1178 (3)0.162 (4)0.50
H29J0.54590.04620.07670.194*0.50
H29K0.43460.02330.13240.194*0.50
H29L0.54160.03820.15090.194*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0451 (12)0.0402 (12)0.0463 (13)0.0164 (10)0.0167 (10)0.0071 (10)
C2A0.0488 (13)0.0301 (11)0.0568 (15)0.0160 (10)0.0208 (11)0.0096 (10)
C3A0.0519 (15)0.0387 (13)0.0849 (19)0.0168 (11)0.0232 (14)0.0072 (12)
C4A0.0597 (17)0.0410 (15)0.141 (3)0.0194 (12)0.054 (2)0.0146 (17)
C5A0.107 (3)0.0442 (16)0.126 (3)0.0252 (17)0.083 (2)0.0149 (17)
C6A0.114 (3)0.0398 (14)0.0758 (19)0.0274 (15)0.0576 (19)0.0114 (13)
C7A0.0753 (17)0.0292 (11)0.0561 (15)0.0202 (11)0.0296 (13)0.0113 (10)
C8A0.0669 (16)0.0286 (11)0.0558 (15)0.0157 (11)0.0089 (13)0.0077 (10)
C9A0.106 (3)0.0413 (15)0.0625 (18)0.0213 (16)0.0045 (18)0.0036 (13)
C10A0.088 (3)0.0463 (17)0.114 (3)0.0170 (17)0.028 (2)0.0006 (18)
C11A0.0491 (17)0.0478 (17)0.145 (3)0.0132 (13)0.007 (2)0.013 (2)
C12A0.0501 (15)0.0450 (14)0.100 (2)0.0167 (12)0.0187 (15)0.0146 (14)
C13A0.0458 (13)0.0309 (11)0.0626 (16)0.0142 (10)0.0121 (11)0.0113 (10)
C14A0.0517 (13)0.0423 (13)0.0530 (14)0.0186 (10)0.0200 (11)0.0046 (10)
C15A0.0473 (13)0.0409 (12)0.0515 (14)0.0170 (10)0.0169 (11)0.0033 (10)
C16A0.0454 (13)0.0429 (12)0.0534 (14)0.0169 (10)0.0170 (11)0.0016 (10)
C17A0.0456 (12)0.0416 (12)0.0577 (15)0.0162 (10)0.0197 (11)0.0022 (10)
C18A0.0529 (14)0.0415 (13)0.0538 (14)0.0142 (10)0.0170 (11)0.0034 (10)
C19A0.0459 (13)0.0388 (12)0.0587 (15)0.0124 (10)0.0184 (11)0.0002 (10)
C20A0.0520 (14)0.0390 (13)0.0691 (16)0.0116 (10)0.0192 (12)0.0055 (11)
C21A0.0620 (16)0.0433 (14)0.103 (2)0.0186 (12)0.0329 (16)0.0079 (14)
C22A0.0559 (14)0.0475 (13)0.0527 (14)0.0195 (11)0.0222 (12)0.0109 (11)
C23A0.0517 (13)0.0467 (13)0.0530 (14)0.0186 (11)0.0188 (11)0.0140 (11)
C24A0.0541 (14)0.0511 (14)0.0533 (14)0.0209 (11)0.0193 (12)0.0149 (11)
C25A0.0632 (15)0.0516 (14)0.0565 (15)0.0241 (12)0.0201 (13)0.0163 (12)
C26A0.0824 (18)0.0598 (16)0.0610 (16)0.0358 (14)0.0276 (14)0.0204 (13)
C27A0.0599 (15)0.0528 (15)0.0658 (17)0.0217 (12)0.0184 (13)0.0158 (12)
C28A0.125 (3)0.0656 (19)0.074 (2)0.0475 (18)0.0258 (19)0.0238 (15)
C29A0.091 (2)0.0614 (19)0.102 (2)0.0339 (16)0.0119 (19)0.0191 (16)
C1B0.0418 (12)0.0499 (13)0.0441 (13)0.0152 (10)0.0090 (10)0.0012 (10)
C2B0.0513 (14)0.0411 (12)0.0461 (13)0.0172 (10)0.0082 (11)0.0024 (10)
C3B0.0661 (16)0.0589 (15)0.0501 (15)0.0239 (12)0.0171 (13)0.0007 (12)
C4B0.103 (2)0.0649 (17)0.0553 (17)0.0412 (17)0.0280 (17)0.0049 (13)
C5B0.105 (3)0.0655 (18)0.0521 (17)0.0349 (17)0.0084 (18)0.0047 (14)
C6B0.0759 (19)0.0500 (15)0.0570 (17)0.0213 (13)0.0115 (15)0.0053 (12)
C7B0.0556 (15)0.0381 (12)0.0527 (15)0.0162 (11)0.0058 (12)0.0017 (10)
C8B0.0449 (13)0.0407 (13)0.0686 (17)0.0146 (10)0.0064 (12)0.0063 (11)
C9B0.0532 (17)0.0621 (18)0.105 (2)0.0153 (13)0.0160 (17)0.0030 (16)
C10B0.0554 (18)0.085 (2)0.124 (3)0.0213 (16)0.032 (2)0.007 (2)
C11B0.088 (2)0.090 (2)0.103 (3)0.0389 (19)0.058 (2)0.0151 (19)
C12B0.0689 (18)0.0770 (19)0.0730 (19)0.0315 (15)0.0278 (15)0.0087 (15)
C13B0.0521 (14)0.0490 (14)0.0576 (15)0.0206 (11)0.0200 (12)0.0088 (11)
C14B0.0476 (13)0.0545 (14)0.0454 (13)0.0180 (11)0.0101 (11)0.0018 (11)
C15B0.0504 (14)0.0551 (15)0.0540 (15)0.0177 (11)0.0086 (12)0.0031 (11)
C16B0.0549 (14)0.0539 (15)0.0562 (15)0.0210 (12)0.0111 (12)0.0016 (11)
C17B0.0608 (16)0.0564 (16)0.0640 (17)0.0193 (13)0.0090 (13)0.0001 (12)
C18B0.0649 (16)0.0518 (15)0.0731 (18)0.0214 (13)0.0082 (14)0.0015 (13)
C19B0.078 (2)0.0532 (17)0.100 (2)0.0194 (15)0.0088 (17)0.0043 (15)
C20B0.116 (3)0.0542 (19)0.138 (3)0.0302 (19)0.003 (2)0.0089 (19)
C21B0.165 (4)0.061 (2)0.215 (5)0.034 (3)0.008 (4)0.026 (3)
C22B0.0482 (13)0.0514 (14)0.0514 (14)0.0163 (11)0.0099 (11)0.0023 (11)
C23B0.0587 (15)0.0537 (15)0.0763 (18)0.0231 (12)0.0130 (14)0.0023 (13)
C24B0.0750 (18)0.0526 (16)0.0775 (19)0.0245 (14)0.0226 (15)0.0020 (13)
C25B0.0731 (19)0.0609 (18)0.106 (2)0.0161 (15)0.0194 (18)0.0086 (16)
C26B0.086 (2)0.0668 (19)0.093 (2)0.0214 (16)0.0250 (18)0.0025 (16)
C27B0.098 (2)0.0716 (19)0.0712 (19)0.0468 (17)0.0262 (17)0.0067 (15)
C28B0.088 (2)0.078 (2)0.078 (2)0.0356 (17)0.0186 (17)0.0022 (16)
C29B0.086 (2)0.079 (2)0.094 (2)0.0357 (17)0.0064 (18)0.0104 (17)
C1C0.0340 (11)0.0406 (12)0.0460 (13)0.0110 (9)0.0112 (10)0.0037 (9)
C2C0.0384 (12)0.0433 (12)0.0399 (12)0.0126 (9)0.0134 (10)0.0035 (9)
C3C0.0430 (12)0.0471 (13)0.0446 (13)0.0173 (10)0.0111 (10)0.0051 (10)
C4C0.0603 (15)0.0457 (13)0.0515 (14)0.0206 (12)0.0215 (12)0.0009 (11)
C5C0.0487 (14)0.0448 (13)0.0600 (15)0.0059 (11)0.0212 (12)0.0054 (11)
C6C0.0361 (12)0.0501 (14)0.0551 (14)0.0102 (10)0.0101 (10)0.0026 (11)
C7C0.0347 (11)0.0456 (12)0.0418 (12)0.0102 (9)0.0123 (10)0.0040 (10)
C8C0.0390 (12)0.0449 (12)0.0421 (12)0.0138 (10)0.0113 (10)0.0014 (10)
C9C0.0404 (12)0.0555 (15)0.0591 (15)0.0167 (11)0.0081 (11)0.0012 (12)
C10C0.0553 (15)0.0583 (16)0.0637 (16)0.0312 (13)0.0124 (12)0.0051 (12)
C11C0.0647 (16)0.0440 (13)0.0636 (16)0.0219 (12)0.0208 (13)0.0011 (11)
C12C0.0475 (13)0.0424 (13)0.0595 (15)0.0110 (10)0.0161 (12)0.0076 (11)
C13C0.0381 (12)0.0424 (12)0.0433 (12)0.0130 (9)0.0131 (10)0.0039 (9)
C14C0.0365 (11)0.0445 (12)0.0531 (14)0.0116 (10)0.0117 (10)0.0034 (10)
C15C0.0416 (12)0.0512 (13)0.0522 (14)0.0131 (10)0.0157 (11)0.0016 (11)
C16C0.0439 (12)0.0465 (13)0.0528 (14)0.0136 (10)0.0165 (11)0.0001 (10)
C17C0.0503 (14)0.0556 (14)0.0522 (15)0.0128 (11)0.0166 (12)0.0015 (11)
C18C0.0561 (15)0.0617 (16)0.0580 (16)0.0072 (12)0.0206 (13)0.0081 (12)
C19C0.076 (2)0.112 (3)0.0602 (18)0.0062 (18)0.0254 (16)0.0168 (17)
C20C0.105 (3)0.148 (4)0.083 (2)0.014 (2)0.046 (2)0.016 (2)
C21C0.148 (4)0.351 (9)0.055 (2)0.003 (5)0.036 (3)0.017 (4)
C22C0.0372 (12)0.0447 (12)0.0509 (14)0.0110 (10)0.0093 (10)0.0071 (10)
C23C0.0417 (12)0.0505 (13)0.0487 (14)0.0123 (10)0.0092 (11)0.0065 (11)
C24C0.0414 (12)0.0606 (15)0.0500 (14)0.0170 (11)0.0087 (11)0.0101 (11)
C25C0.0466 (13)0.0580 (15)0.0485 (14)0.0205 (11)0.0084 (11)0.0048 (11)
C26C0.0521 (15)0.098 (2)0.0538 (16)0.0296 (14)0.0066 (12)0.0175 (14)
C27C0.0684 (17)0.108 (2)0.0534 (16)0.0438 (17)0.0146 (14)0.0073 (15)
C28C0.113 (3)0.238 (5)0.059 (2)0.087 (4)0.005 (2)0.043 (3)
C29C0.148 (8)0.297 (15)0.086 (6)0.091 (9)0.015 (6)0.073 (8)
C29D0.118 (7)0.197 (11)0.169 (9)0.030 (7)0.016 (7)0.120 (9)
Geometric parameters (Å, º) top
C1A—C2A1.521 (3)C19B—C20B1.506 (4)
C1A—C13A1.525 (3)C19B—H19C0.9900
C1A—C14A1.540 (3)C19B—H19D0.9900
C1A—C22A1.540 (3)C20B—C21B1.504 (5)
C2A—C3A1.382 (3)C20B—H20C0.9900
C2A—C7A1.398 (3)C20B—H20D0.9900
C3A—C4A1.399 (4)C21B—H21D0.9800
C3A—H3A0.9500C21B—H21E0.9800
C4A—C5A1.370 (4)C21B—H21F0.9800
C4A—H4A0.9500C22B—C23B1.510 (3)
C5A—C6A1.368 (4)C22B—H22C0.9900
C5A—H5A0.9500C22B—H22D0.9900
C6A—C7A1.387 (3)C23B—C24B1.500 (3)
C6A—H6A0.9500C23B—H23C0.9900
C7A—C8A1.460 (3)C23B—H23D0.9900
C8A—C9A1.393 (4)C24B—C25B1.550 (4)
C8A—C13A1.399 (3)C24B—H24C0.9900
C9A—C10A1.367 (5)C24B—H24D0.9900
C9A—H9A0.9500C25B—C26B1.462 (4)
C10A—C11A1.372 (5)C25B—H25C0.9900
C10A—H10A0.9500C25B—H25D0.9900
C11A—C12A1.391 (4)C26B—C27B1.525 (4)
C11A—H11A0.9500C26B—H26C0.9900
C12A—C13A1.389 (3)C26B—H26D0.9900
C12A—H12A0.9500C27B—C28B1.489 (4)
C14A—C15A1.519 (3)C27B—H27C0.9900
C14A—H14A0.9900C27B—H27D0.9900
C14A—H14B0.9900C28B—C29B1.472 (4)
C15A—C16A1.520 (3)C28B—H28C0.9900
C15A—H15A0.9900C28B—H28D0.9900
C15A—H15B0.9900C29B—H29D0.9800
C16A—C17A1.517 (3)C29B—H29E0.9800
C16A—H16A0.9900C29B—H29F0.9800
C16A—H16B0.9900C1C—C2C1.524 (3)
C17A—C18A1.517 (3)C1C—C13C1.522 (3)
C17A—H17A0.9900C1C—C14C1.546 (3)
C17A—H17B0.9900C1C—C22C1.537 (3)
C18A—C19A1.516 (3)C2C—C3C1.384 (3)
C18A—H18A0.9900C2C—C7C1.396 (3)
C18A—H18B0.9900C3C—C4C1.382 (3)
C19A—C20A1.512 (3)C3C—H3C0.9500
C19A—H19A0.9900C4C—C5C1.383 (3)
C19A—H19B0.9900C4C—H4C0.9500
C20A—C21A1.511 (3)C5C—C6C1.384 (3)
C20A—H20A0.9900C5C—H5C0.9500
C20A—H20B0.9900C6C—C7C1.384 (3)
C21A—H21A0.9800C6C—H6C0.9500
C21A—H21B0.9800C7C—C8C1.471 (3)
C21A—H21C0.9800C8C—C9C1.390 (3)
C22A—C23A1.516 (3)C8C—C13C1.395 (3)
C22A—H22A0.9900C9C—C10C1.378 (3)
C22A—H22B0.9900C9C—H9C0.9500
C23A—C24A1.522 (3)C10C—C11C1.382 (3)
C23A—H23A0.9900C10C—H10C0.9500
C23A—H23B0.9900C11C—C12C1.381 (3)
C24A—C25A1.513 (3)C11C—H11C0.9500
C24A—H24A0.9900C12C—C13C1.383 (3)
C24A—H24B0.9900C12C—H12C0.9500
C25A—C26A1.513 (3)C14C—C15C1.520 (3)
C25A—H25A0.9900C14C—H14E0.9900
C25A—H25B0.9900C14C—H14F0.9900
C26A—C27A1.504 (3)C15C—C16C1.519 (3)
C26A—H26A0.9900C15C—H15E0.9900
C26A—H26B0.9900C15C—H15F0.9900
C27A—C28A1.487 (3)C16C—C17C1.513 (3)
C27A—H27A0.9900C16C—H16E0.9900
C27A—H27B0.9900C16C—H16F0.9900
C28A—C29A1.496 (4)C17C—C18C1.509 (3)
C28A—H28A0.9900C17C—H17E0.9900
C28A—H28B0.9900C17C—H17F0.9900
C29A—H29A0.9800C18C—C19C1.519 (4)
C29A—H29B0.9800C18C—H18E0.9900
C29A—H29C0.9800C18C—H18F0.9900
C1B—C2B1.518 (3)C19C—C20C1.461 (4)
C1B—C13B1.522 (3)C19C—H19E0.9900
C1B—C14B1.548 (3)C19C—H19F0.9900
C1B—C22B1.543 (3)C20C—C21C1.497 (5)
C2B—C3B1.379 (3)C20C—H20E0.9900
C2B—C7B1.390 (3)C20C—H20F0.9900
C3B—C4B1.384 (3)C21C—H21G0.9800
C3B—H3B0.9500C21C—H21H0.9800
C4B—C5B1.372 (4)C21C—H21I0.9800
C4B—H4B0.9500C22C—C23C1.521 (3)
C5B—C6B1.374 (4)C22C—H22E0.9900
C5B—H5B0.9500C22C—H22F0.9900
C6B—C7B1.394 (3)C23C—C24C1.516 (3)
C6B—H6B0.9500C23C—H23E0.9900
C7B—C8B1.456 (3)C23C—H23F0.9900
C8B—C9B1.390 (4)C24C—C25C1.512 (3)
C8B—C13B1.398 (3)C24C—H24E0.9900
C9B—C10B1.364 (4)C24C—H24F0.9900
C9B—H9B0.9500C25C—C26C1.514 (3)
C10B—C11B1.369 (4)C25C—H25E0.9900
C10B—H10B0.9500C25C—H25F0.9900
C11B—C12B1.409 (4)C26C—C27C1.517 (3)
C11B—H11B0.9500C26C—H26E0.9900
C12B—C13B1.379 (3)C26C—H26F0.9900
C12B—H12B0.9500C27C—C28C1.527 (4)
C14B—C15B1.520 (3)C27C—H27E0.9900
C14B—H14C0.9900C27C—H27F0.9900
C14B—H14D0.9900C28C—C29C1.5093 (5)
C15B—C16B1.520 (3)C28C—C29D1.5099 (6)
C15B—H15C0.9900C28C—H28E0.9900
C15B—H15D0.9900C28C—H28F0.9900
C16B—C17B1.510 (3)C28C—H28G0.9900
C16B—H16C0.9900C28C—H28H0.9900
C16B—H16D0.9900C29C—H29G0.9800
C17B—C18B1.510 (3)C29C—H29H0.9800
C17B—H17C0.9900C29C—H29I0.9800
C17B—H17D0.9900C29D—H29J0.9800
C18B—C19B1.509 (4)C29D—H29K0.9800
C18B—H18C0.9900C29D—H29L0.9800
C18B—H18D0.9900
C2A—C1A—C13A100.79 (18)C20B—C19B—H19C108.6
C2A—C1A—C14A111.39 (17)C20B—C19B—H19D108.6
C2A—C1A—C22A112.01 (17)H19C—C19B—H19D107.5
C13A—C1A—C14A111.77 (17)C19B—C20B—C21B114.8 (3)
C13A—C1A—C22A112.05 (17)C19B—C20B—H20C108.6
C14A—C1A—C22A108.72 (18)C19B—C20B—H20D108.6
C1A—C2A—C3A129.0 (2)C21B—C20B—H20C108.6
C1A—C2A—C7A110.99 (19)C21B—C20B—H20D108.6
C3A—C2A—C7A120.0 (2)H20C—C20B—H20D107.5
C2A—C3A—C4A118.7 (3)C20B—C21B—H21D109.5
C2A—C3A—H3A120.6C20B—C21B—H21E109.5
C4A—C3A—H3A120.6C20B—C21B—H21F109.5
C3A—C4A—C5A120.2 (3)H21D—C21B—H21E109.5
C3A—C4A—H4A119.9H21D—C21B—H21F109.5
C5A—C4A—H4A119.9H21E—C21B—H21F109.5
C4A—C5A—C6A121.9 (3)C1B—C22B—C23B115.25 (19)
C4A—C5A—H5A119.1C1B—C22B—H22C108.5
C6A—C5A—H5A119.1C1B—C22B—H22D108.5
C5A—C6A—C7A118.5 (3)C23B—C22B—H22C108.5
C5A—C6A—H6A120.7C23B—C22B—H22D108.5
C7A—C6A—H6A120.7H22C—C22B—H22D107.5
C2A—C7A—C6A120.6 (2)C22B—C23B—C24B114.2 (2)
C2A—C7A—C8A108.8 (2)C22B—C23B—H23C108.7
C6A—C7A—C8A130.6 (3)C22B—C23B—H23D108.7
C7A—C8A—C9A132.1 (3)C24B—C23B—H23C108.7
C7A—C8A—C13A108.2 (2)C24B—C23B—H23D108.7
C9A—C8A—C13A119.8 (3)H23C—C23B—H23D107.6
C8A—C9A—C10A119.6 (3)C23B—C24B—C25B112.2 (2)
C8A—C9A—H9A120.2C23B—C24B—H24C109.2
C10A—C9A—H9A120.2C23B—C24B—H24D109.2
C9A—C10A—C11A120.9 (3)C25B—C24B—H24C109.2
C9A—C10A—H10A119.5C25B—C24B—H24D109.2
C11A—C10A—H10A119.5H24C—C24B—H24D107.9
C10A—C11A—C12A120.8 (3)C24B—C25B—C26B113.6 (2)
C10A—C11A—H11A119.6C24B—C25B—H25C108.8
C12A—C11A—H11A119.6C24B—C25B—H25D108.8
C11A—C12A—C13A118.8 (3)C26B—C25B—H25C108.8
C11A—C12A—H12A120.6C26B—C25B—H25D108.8
C13A—C12A—H12A120.6H25C—C25B—H25D107.7
C1A—C13A—C8A111.23 (19)C25B—C26B—C27B114.7 (3)
C1A—C13A—C12A128.6 (2)C25B—C26B—H26C108.6
C8A—C13A—C12A120.1 (2)C25B—C26B—H26D108.6
C1A—C14A—C15A116.12 (19)C27B—C26B—H26C108.6
C1A—C14A—H14A108.3C27B—C26B—H26D108.6
C1A—C14A—H14B108.3H26C—C26B—H26D107.6
C15A—C14A—H14A108.3C26B—C27B—C28B111.0 (3)
C15A—C14A—H14B108.3C26B—C27B—H27C109.4
H14A—C14A—H14B107.4C26B—C27B—H27D109.4
C14A—C15A—C16A112.94 (19)C28B—C27B—H27C109.4
C14A—C15A—H15A109.0C28B—C27B—H27D109.4
C14A—C15A—H15B109.0H27C—C27B—H27D108.0
C16A—C15A—H15A109.0C27B—C28B—C29B115.0 (3)
C16A—C15A—H15B109.0C27B—C28B—H28C108.5
H15A—C15A—H15B107.8C27B—C28B—H28D108.5
C15A—C16A—C17A113.54 (19)C29B—C28B—H28C108.5
C15A—C16A—H16A108.9C29B—C28B—H28D108.5
C15A—C16A—H16B108.9H28C—C28B—H28D107.5
C17A—C16A—H16A108.9C28B—C29B—H29D109.5
C17A—C16A—H16B108.9C28B—C29B—H29E109.5
H16A—C16A—H16B107.7C28B—C29B—H29F109.5
C16A—C17A—C18A114.41 (19)H29D—C29B—H29E109.5
C16A—C17A—H17A108.7H29D—C29B—H29F109.5
C16A—C17A—H17B108.7H29E—C29B—H29F109.5
C18A—C17A—H17A108.7C2C—C1C—C13C101.07 (16)
C18A—C17A—H17B108.7C2C—C1C—C14C110.59 (16)
H17A—C17A—H17B107.6C2C—C1C—C22C112.58 (17)
C17A—C18A—C19A113.72 (19)C13C—C1C—C14C111.58 (17)
C17A—C18A—H18A108.8C13C—C1C—C22C111.77 (17)
C17A—C18A—H18B108.8C14C—C1C—C22C109.10 (16)
C19A—C18A—H18A108.8C1C—C2C—C3C129.05 (19)
C19A—C18A—H18B108.8C1C—C2C—C7C111.01 (18)
H18A—C18A—H18B107.7C3C—C2C—C7C119.93 (19)
C18A—C19A—C20A114.69 (19)C2C—C3C—C4C119.2 (2)
C18A—C19A—H19A108.6C2C—C3C—H3C120.4
C18A—C19A—H19B108.6C4C—C3C—H3C120.4
C20A—C19A—H19A108.6C3C—C4C—C5C121.0 (2)
C20A—C19A—H19B108.6C3C—C4C—H4C119.5
H19A—C19A—H19B107.6C5C—C4C—H4C119.5
C19A—C20A—C21A113.3 (2)C4C—C5C—C6C120.2 (2)
C19A—C20A—H20A108.9C4C—C5C—H5C119.9
C19A—C20A—H20B108.9C6C—C5C—H5C119.9
C21A—C20A—H20A108.9C5C—C6C—C7C119.2 (2)
C21A—C20A—H20B108.9C5C—C6C—H6C120.4
H20A—C20A—H20B107.7C7C—C6C—H6C120.4
C20A—C21A—H21A109.5C2C—C7C—C6C120.6 (2)
C20A—C21A—H21B109.5C2C—C7C—C8C108.37 (17)
C20A—C21A—H21C109.5C6C—C7C—C8C131.1 (2)
H21A—C21A—H21B109.5C7C—C8C—C9C130.95 (19)
H21A—C21A—H21C109.5C7C—C8C—C13C108.37 (18)
H21B—C21A—H21C109.5C9C—C8C—C13C120.7 (2)
C1A—C22A—C23A116.27 (19)C8C—C9C—C10C119.0 (2)
C1A—C22A—H22A108.2C8C—C9C—H9C120.5
C1A—C22A—H22B108.2C10C—C9C—H9C120.5
C23A—C22A—H22A108.2C9C—C10C—C11C120.4 (2)
C23A—C22A—H22B108.2C9C—C10C—H10C119.8
H22A—C22A—H22B107.4C11C—C10C—H10C119.8
C22A—C23A—C24A112.8 (2)C10C—C11C—C12C120.9 (2)
C22A—C23A—H23A109.0C10C—C11C—H11C119.6
C22A—C23A—H23B109.0C12C—C11C—H11C119.6
C24A—C23A—H23A109.0C11C—C12C—C13C119.4 (2)
C24A—C23A—H23B109.0C11C—C12C—H12C120.3
H23A—C23A—H23B107.8C13C—C12C—H12C120.3
C23A—C24A—C25A113.5 (2)C1C—C13C—C8C111.16 (18)
C23A—C24A—H24A108.9C1C—C13C—C12C129.22 (19)
C23A—C24A—H24B108.9C8C—C13C—C12C119.6 (2)
C25A—C24A—H24A108.9C1C—C14C—C15C115.00 (17)
C25A—C24A—H24B108.9C1C—C14C—H14E108.5
H24A—C24A—H24B107.7C1C—C14C—H14F108.5
C24A—C25A—C26A114.6 (2)C15C—C14C—H14E108.5
C24A—C25A—H25A108.6C15C—C14C—H14F108.5
C24A—C25A—H25B108.6H14E—C14C—H14F107.5
C26A—C25A—H25A108.6C14C—C15C—C16C114.22 (18)
C26A—C25A—H25B108.6C14C—C15C—H15E108.7
H25A—C25A—H25B107.6C14C—C15C—H15F108.7
C25A—C26A—C27A114.2 (2)C16C—C15C—H15E108.7
C25A—C26A—H26A108.7C16C—C15C—H15F108.7
C25A—C26A—H26B108.7H15E—C15C—H15F107.6
C27A—C26A—H26A108.7C15C—C16C—C17C112.63 (18)
C27A—C26A—H26B108.7C15C—C16C—H16E109.1
H26A—C26A—H26B107.6C15C—C16C—H16F109.1
C26A—C27A—C28A115.9 (2)C17C—C16C—H16E109.1
C26A—C27A—H27A108.3C17C—C16C—H16F109.1
C26A—C27A—H27B108.3H16E—C16C—H16F107.8
C28A—C27A—H27A108.3C16C—C17C—C18C114.5 (2)
C28A—C27A—H27B108.3C16C—C17C—H17E108.6
H27A—C27A—H27B107.4C16C—C17C—H17F108.6
C27A—C28A—C29A116.2 (3)C18C—C17C—H17E108.6
C27A—C28A—H28A108.2C18C—C17C—H17F108.6
C27A—C28A—H28B108.2H17E—C17C—H17F107.6
C29A—C28A—H28A108.2C17C—C18C—C19C113.0 (2)
C29A—C28A—H28B108.2C17C—C18C—H18E109.0
H28A—C28A—H28B107.4C17C—C18C—H18F109.0
C28A—C29A—H29A109.5C19C—C18C—H18E109.0
C28A—C29A—H29B109.5C19C—C18C—H18F109.0
C28A—C29A—H29C109.5H18E—C18C—H18F107.8
H29A—C29A—H29B109.5C18C—C19C—C20C115.7 (3)
H29A—C29A—H29C109.5C18C—C19C—H19E108.4
H29B—C29A—H29C109.5C18C—C19C—H19F108.4
C2B—C1B—C13B100.56 (18)C20C—C19C—H19E108.4
C2B—C1B—C14B111.04 (18)C20C—C19C—H19F108.4
C2B—C1B—C22B111.51 (18)H19E—C19C—H19F107.4
C13B—C1B—C14B112.54 (18)C19C—C20C—C21C112.6 (3)
C13B—C1B—C22B112.54 (18)C19C—C20C—H20E109.1
C14B—C1B—C22B108.53 (17)C19C—C20C—H20F109.1
C1B—C2B—C3B128.7 (2)C21C—C20C—H20E109.1
C1B—C2B—C7B111.6 (2)C21C—C20C—H20F109.1
C3B—C2B—C7B119.7 (2)H20E—C20C—H20F107.8
C2B—C3B—C4B119.5 (3)C20C—C21C—H21G109.5
C2B—C3B—H3B120.3C20C—C21C—H21H109.5
C4B—C3B—H3B120.3C20C—C21C—H21I109.5
C3B—C4B—C5B120.6 (3)H21G—C21C—H21H109.5
C3B—C4B—H4B119.7H21G—C21C—H21I109.5
C5B—C4B—H4B119.7H21H—C21C—H21I109.5
C4B—C5B—C6B121.0 (3)C1C—C22C—C23C115.73 (17)
C4B—C5B—H5B119.5C1C—C22C—H22E108.3
C6B—C5B—H5B119.5C1C—C22C—H22F108.3
C5B—C6B—C7B118.6 (3)C23C—C22C—H22E108.3
C5B—C6B—H6B120.7C23C—C22C—H22F108.3
C7B—C6B—H6B120.7H22E—C22C—H22F107.4
C2B—C7B—C6B120.6 (2)C22C—C23C—C24C113.44 (18)
C2B—C7B—C8B108.2 (2)C22C—C23C—H23E108.9
C6B—C7B—C8B131.1 (2)C22C—C23C—H23F108.9
C7B—C8B—C9B130.7 (3)C24C—C23C—H23E108.9
C7B—C8B—C13B108.7 (2)C24C—C23C—H23F108.9
C9B—C8B—C13B120.6 (3)H23E—C23C—H23F107.7
C8B—C9B—C10B118.6 (3)C23C—C24C—C25C114.02 (18)
C8B—C9B—H9B120.7C23C—C24C—H24E108.7
C10B—C9B—H9B120.7C23C—C24C—H24F108.7
C9B—C10B—C11B121.7 (3)C25C—C24C—H24E108.7
C9B—C10B—H10B119.1C25C—C24C—H24F108.7
C11B—C10B—H10B119.1H24E—C24C—H24F107.6
C10B—C11B—C12B120.5 (3)C24C—C25C—C26C113.26 (19)
C10B—C11B—H11B119.7C24C—C25C—H25E108.9
C12B—C11B—H11B119.7C24C—C25C—H25F108.9
C11B—C12B—C13B118.2 (3)C26C—C25C—H25E108.9
C11B—C12B—H12B120.9C26C—C25C—H25F108.9
C13B—C12B—H12B120.9H25E—C25C—H25F107.7
C1B—C13B—C8B110.9 (2)C25C—C26C—C27C114.9 (2)
C1B—C13B—C12B128.8 (2)C25C—C26C—H26E108.6
C8B—C13B—C12B120.3 (2)C25C—C26C—H26F108.6
C1B—C14B—C15B115.80 (18)C27C—C26C—H26E108.6
C1B—C14B—H14C108.3C27C—C26C—H26F108.6
C1B—C14B—H14D108.3H26E—C26C—H26F107.5
C15B—C14B—H14C108.3C26C—C27C—C28C112.3 (2)
C15B—C14B—H14D108.3C26C—C27C—H27E109.1
H14C—C14B—H14D107.4C26C—C27C—H27F109.1
C14B—C15B—C16B113.23 (19)C28C—C27C—H27E109.1
C14B—C15B—H15C108.9C28C—C27C—H27F109.1
C14B—C15B—H15D108.9H27E—C27C—H27F107.9
C16B—C15B—H15C108.9C27C—C28C—C29C112.9 (2)
C16B—C15B—H15D108.9C27C—C28C—C29D112.8 (2)
H15C—C15B—H15D107.7C27C—C28C—H28E109.0
C15B—C16B—C17B114.2 (2)C27C—C28C—H28F109.0
C15B—C16B—H16C108.7C29C—C28C—H28E109.0
C15B—C16B—H16D108.7C29C—C28C—H28F109.0
C17B—C16B—H16C108.7H28E—C28C—H28F107.8
C17B—C16B—H16D108.7C27C—C28C—H28G109.0
H16C—C16B—H16D107.6C27C—C28C—H28H109.0
C16B—C17B—C18B114.6 (2)C29D—C28C—H28G109.0
C16B—C17B—H17C108.6C29D—C28C—H28H109.0
C16B—C17B—H17D108.6H28G—C28C—H28H107.8
C18B—C17B—H17C108.6C28C—C29C—H29G109.5
C18B—C17B—H17D108.6C28C—C29C—H29H109.5
H17C—C17B—H17D107.6C28C—C29C—H29I109.5
C17B—C18B—C19B114.6 (2)H29G—C29C—H29H109.5
C17B—C18B—H18C108.6H29G—C29C—H29I109.5
C17B—C18B—H18D108.6H29H—C29C—H29I109.5
C19B—C18B—H18C108.6C28C—C29D—H29J109.5
C19B—C18B—H18D108.6C28C—C29D—H29K109.5
H18C—C18B—H18D107.6C28C—C29D—H29L109.5
C18B—C19B—C20B114.8 (3)H29J—C29D—H29K109.5
C18B—C19B—H19C108.6H29J—C29D—H29L109.5
C18B—C19B—H19D108.6H29K—C29D—H29L109.5
C13A—C1A—C2A—C3A178.8 (2)C2B—C7B—C8B—C9B179.6 (2)
C13A—C1A—C2A—C7A2.0 (2)C2B—C7B—C8B—C13B0.4 (2)
C14A—C1A—C2A—C3A62.5 (3)C6B—C7B—C8B—C9B0.4 (4)
C14A—C1A—C2A—C7A116.7 (2)C6B—C7B—C8B—C13B179.6 (2)
C22A—C1A—C2A—C3A59.5 (3)C7B—C8B—C9B—C10B179.9 (3)
C22A—C1A—C2A—C7A121.3 (2)C13B—C8B—C9B—C10B0.2 (4)
C2A—C1A—C13A—C8A1.8 (2)C7B—C8B—C13B—C1B0.2 (3)
C2A—C1A—C13A—C12A177.5 (2)C7B—C8B—C13B—C12B179.8 (2)
C14A—C1A—C13A—C8A116.6 (2)C9B—C8B—C13B—C1B179.8 (2)
C14A—C1A—C13A—C12A64.0 (3)C9B—C8B—C13B—C12B0.2 (4)
C22A—C1A—C13A—C8A121.0 (2)C8B—C9B—C10B—C11B0.0 (5)
C22A—C1A—C13A—C12A58.3 (3)C9B—C10B—C11B—C12B0.5 (5)
C2A—C1A—C14A—C15A50.1 (3)C10B—C11B—C12B—C13B0.9 (4)
C13A—C1A—C14A—C15A61.7 (3)C11B—C12B—C13B—C1B179.8 (2)
C22A—C1A—C14A—C15A174.04 (18)C11B—C12B—C13B—C8B0.7 (4)
C2A—C1A—C22A—C23A56.6 (3)C1B—C14B—C15B—C16B172.7 (2)
C13A—C1A—C22A—C23A55.8 (3)C14B—C15B—C16B—C17B174.7 (2)
C14A—C1A—C22A—C23A179.84 (19)C15B—C16B—C17B—C18B179.9 (2)
C1A—C2A—C3A—C4A179.5 (2)C16B—C17B—C18B—C19B178.8 (2)
C7A—C2A—C3A—C4A0.4 (3)C17B—C18B—C19B—C20B179.9 (3)
C1A—C2A—C7A—C6A179.59 (18)C18B—C19B—C20B—C21B179.9 (3)
C1A—C2A—C7A—C8A1.5 (2)C1B—C22B—C23B—C24B176.2 (2)
C3A—C2A—C7A—C6A0.3 (3)C22B—C23B—C24B—C25B176.1 (2)
C3A—C2A—C7A—C8A179.19 (19)C23B—C24B—C25B—C26B177.1 (3)
C2A—C3A—C4A—C5A0.0 (4)C24B—C25B—C26B—C27B176.4 (3)
C3A—C4A—C5A—C6A0.6 (4)C25B—C26B—C27B—C28B176.2 (3)
C4A—C5A—C6A—C7A0.6 (4)C26B—C27B—C28B—C29B177.5 (3)
C5A—C6A—C7A—C2A0.2 (3)C13C—C1C—C2C—C3C179.8 (2)
C5A—C6A—C7A—C8A178.4 (2)C13C—C1C—C2C—C7C1.2 (2)
C2A—C7A—C8A—C9A178.8 (2)C14C—C1C—C2C—C3C61.9 (3)
C2A—C7A—C8A—C13A0.3 (2)C14C—C1C—C2C—C7C117.06 (19)
C6A—C7A—C8A—C9A0.0 (4)C22C—C1C—C2C—C3C60.5 (3)
C6A—C7A—C8A—C13A179.1 (2)C22C—C1C—C2C—C7C120.60 (19)
C7A—C8A—C9A—C10A178.1 (2)C2C—C1C—C13C—C8C0.3 (2)
C13A—C8A—C9A—C10A1.0 (4)C2C—C1C—C13C—C12C179.6 (2)
C7A—C8A—C13A—C1A1.0 (2)C14C—C1C—C13C—C8C117.28 (19)
C7A—C8A—C13A—C12A178.37 (19)C14C—C1C—C13C—C12C62.8 (3)
C9A—C8A—C13A—C1A179.74 (19)C22C—C1C—C13C—C8C120.25 (19)
C9A—C8A—C13A—C12A0.9 (3)C22C—C1C—C13C—C12C59.7 (3)
C8A—C9A—C10A—C11A0.6 (4)C2C—C1C—C14C—C15C62.1 (2)
C9A—C10A—C11A—C12A0.1 (4)C13C—C1C—C14C—C15C49.6 (2)
C10A—C11A—C12A—C13A0.0 (4)C22C—C1C—C14C—C15C173.55 (18)
C11A—C12A—C13A—C1A179.7 (2)C2C—C1C—C22C—C23C53.3 (2)
C11A—C12A—C13A—C8A0.4 (3)C13C—C1C—C22C—C23C59.6 (2)
C1A—C14A—C15A—C16A178.47 (18)C14C—C1C—C22C—C23C176.50 (18)
C14A—C15A—C16A—C17A173.07 (18)C1C—C2C—C3C—C4C178.2 (2)
C15A—C16A—C17A—C18A175.76 (19)C7C—C2C—C3C—C4C0.6 (3)
C16A—C17A—C18A—C19A174.38 (18)C1C—C2C—C7C—C6C177.82 (19)
C17A—C18A—C19A—C20A174.47 (19)C1C—C2C—C7C—C8C1.7 (2)
C18A—C19A—C20A—C21A172.7 (2)C3C—C2C—C7C—C6C1.2 (3)
C1A—C22A—C23A—C24A177.66 (19)C3C—C2C—C7C—C8C179.26 (19)
C22A—C23A—C24A—C25A178.2 (2)C2C—C3C—C4C—C5C0.4 (3)
C23A—C24A—C25A—C26A177.7 (2)C3C—C4C—C5C—C6C1.0 (3)
C24A—C25A—C26A—C27A176.8 (2)C4C—C5C—C6C—C7C0.4 (3)
C25A—C26A—C27A—C28A179.0 (2)C5C—C6C—C7C—C2C0.7 (3)
C26A—C27A—C28A—C29A177.8 (3)C5C—C6C—C7C—C8C179.9 (2)
C13B—C1B—C2B—C3B178.6 (2)C2C—C7C—C8C—C9C177.6 (2)
C13B—C1B—C2B—C7B0.3 (2)C2C—C7C—C8C—C13C1.5 (2)
C14B—C1B—C2B—C3B62.1 (3)C6C—C7C—C8C—C9C3.0 (4)
C14B—C1B—C2B—C7B119.0 (2)C6C—C7C—C8C—C13C178.0 (2)
C22B—C1B—C2B—C3B59.0 (3)C7C—C8C—C9C—C10C179.7 (2)
C22B—C1B—C2B—C7B119.8 (2)C13C—C8C—C9C—C10C0.8 (3)
C2B—C1B—C13B—C8B0.1 (2)C7C—C8C—C13C—C1C0.7 (2)
C2B—C1B—C13B—C12B179.5 (2)C7C—C8C—C13C—C12C179.40 (19)
C14B—C1B—C13B—C8B118.1 (2)C9C—C8C—C13C—C1C178.5 (2)
C14B—C1B—C13B—C12B62.3 (3)C9C—C8C—C13C—C12C1.5 (3)
C22B—C1B—C13B—C8B118.8 (2)C8C—C9C—C10C—C11C0.4 (4)
C22B—C1B—C13B—C12B60.7 (3)C9C—C10C—C11C—C12C1.0 (4)
C2B—C1B—C14B—C15B65.3 (3)C10C—C11C—C12C—C13C0.4 (4)
C13B—C1B—C14B—C15B46.5 (3)C11C—C12C—C13C—C1C179.1 (2)
C22B—C1B—C14B—C15B171.76 (19)C11C—C12C—C13C—C8C0.8 (3)
C2B—C1B—C22B—C23B57.3 (3)C1C—C14C—C15C—C16C174.89 (18)
C13B—C1B—C22B—C23B54.8 (3)C14C—C15C—C16C—C17C170.23 (19)
C14B—C1B—C22B—C23B179.9 (2)C15C—C16C—C17C—C18C177.23 (19)
C1B—C2B—C3B—C4B179.4 (2)C16C—C17C—C18C—C19C178.3 (2)
C7B—C2B—C3B—C4B0.6 (3)C17C—C18C—C19C—C20C173.1 (3)
C1B—C2B—C7B—C6B179.7 (2)C18C—C19C—C20C—C21C177.7 (4)
C1B—C2B—C7B—C8B0.4 (2)C1C—C22C—C23C—C24C172.97 (18)
C3B—C2B—C7B—C6B0.8 (3)C22C—C23C—C24C—C25C179.22 (19)
C3B—C2B—C7B—C8B178.5 (2)C23C—C24C—C25C—C26C176.4 (2)
C2B—C3B—C4B—C5B0.0 (4)C24C—C25C—C26C—C27C178.1 (2)
C3B—C4B—C5B—C6B0.5 (4)C25C—C26C—C27C—C28C176.7 (2)
C4B—C5B—C6B—C7B0.4 (4)C26C—C27C—C28C—C29C174.9 (5)
C5B—C6B—C7B—C2B0.2 (3)C26C—C27C—C28C—C29D81.3 (5)
C5B—C6B—C7B—C8B178.9 (2)

Experimental details

Crystal data
Chemical formulaC29H42
Mr390.63
Crystal system, space groupTriclinic, P1
Temperature (K)193
a, b, c (Å)13.9223 (18), 14.2423 (18), 21.570 (3)
α, β, γ (°)83.079 (2), 72.024 (2), 70.605 (2)
V3)3836.6 (9)
Z6
Radiation typeMo Kα
µ (mm1)0.06
Crystal size (mm)0.36 × 0.35 × 0.26
Data collection
DiffractometerBruker SMART 1000 CCD area-detector/PLATFORM
diffractometer
Absorption correctionIntegration
(SHELXTL; Bruker, 2003)
Tmin, Tmax0.829, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections
25454, 13469, 8216
Rint0.036
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.190, 1.03
No. of reflections13469
No. of parameters796
No. of restraints4
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.54, 0.19

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2003), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2003), SHELXTL.

Selected geometric parameters (Å, º) top
C1A—C2A1.521 (3)C6A—C7A1.387 (3)
C1A—C13A1.525 (3)C7A—C8A1.460 (3)
C1A—C14A1.540 (3)C8A—C9A1.393 (4)
C1A—C22A1.540 (3)C8A—C13A1.399 (3)
C2A—C3A1.382 (3)C9A—C10A1.367 (5)
C2A—C7A1.398 (3)C10A—C11A1.372 (5)
C3A—C4A1.399 (4)C11A—C12A1.391 (4)
C4A—C5A1.370 (4)C12A—C13A1.389 (3)
C5A—C6A1.368 (4)
C2A—C1A—C13A100.79 (18)C2A—C7A—C8A108.8 (2)
C2A—C1A—C14A111.39 (17)C6A—C7A—C8A130.6 (3)
C2A—C1A—C22A112.01 (17)C7A—C8A—C9A132.1 (3)
C13A—C1A—C14A111.77 (17)C7A—C8A—C13A108.2 (2)
C13A—C1A—C22A112.05 (17)C9A—C8A—C13A119.8 (3)
C14A—C1A—C22A108.72 (18)C8A—C9A—C10A119.6 (3)
C1A—C2A—C3A129.0 (2)C9A—C10A—C11A120.9 (3)
C1A—C2A—C7A110.99 (19)C10A—C11A—C12A120.8 (3)
C3A—C2A—C7A120.0 (2)C11A—C12A—C13A118.8 (3)
C2A—C3A—C4A118.7 (3)C1A—C13A—C8A111.23 (19)
C3A—C4A—C5A120.2 (3)C1A—C13A—C12A128.6 (2)
C4A—C5A—C6A121.9 (3)C8A—C13A—C12A120.1 (2)
C5A—C6A—C7A118.5 (3)C1A—C14A—C15A116.12 (19)
C2A—C7A—C6A120.6 (2)
 

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