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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1603.
Published online 2008 July 26. doi:  10.1107/S1600536808022496
PMCID: PMC2962215

9,9-Dioctyl-2,7-bis­(4,4,5,5-tetra­methyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene

Abstract

In the title mol­ecule, C41H64B2O4, the fluorene unit is essentially planar and the two octyl chains attached to the central C atom inhibit the mol­ecule from engaging in inter­molecular aromatic inter­actions. One of the octyl chains adopts a fully extended conformation, whereas the second incorporates a single gauche conformation. Of the two pinacolatoboronate groups attached at the 2,7-positions, one is partly disordered; one ring C atom and all four methyl groups are disordered equally over two positions.

Related literature

For related literature, see: Cho et al. (2007 [triangle]); Scherf & List (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1603-scheme1.jpg

Experimental

Crystal data

  • C41H64B2O4
  • M r = 642.54
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1603-efi1.jpg
  • a = 12.6694 (12) Å
  • b = 13.3457 (11) Å
  • c = 14.0819 (11) Å
  • α = 68.944 (3)°
  • β = 89.834 (4)°
  • γ = 64.306 (4)°
  • V = 1968.9 (3) Å3
  • Z = 2
  • Cu Kα radiation
  • μ = 0.51 mm−1
  • T = 150 K
  • 0.10 × 0.10 × 0.05 mm

Data collection

  • Bruker Microstar diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2007 [triangle]) T min = 0.840, T max = 0.975
  • 30971 measured reflections
  • 6210 independent reflections
  • 5656 reflections with I > 2σ(I)
  • R int = 0.054

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.104
  • S = 1.04
  • 6210 reflections
  • 476 parameters
  • 66 restraints
  • H-atom parameters constrained
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2006 [triangle]); cell refinement: SAINT (Bruker, 2006 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]) and Materials Studio (Accelrys, 2005 [triangle]); software used to prepare material for publication: UdMX (Maris, 2004 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022496/lh2661sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022496/lh2661Isup2.hkl

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

Acknowledgments

The authors acknowledge financial support from the Natural Sciences and Engineering Research Council of Canada and the Canada Foundation for Innovation. Dr Thierry Maris and Professor James D. Wuest are gratefully acknowledged for their help in preparing the manuscript. EG also thanks the Natural Sciences and Engineering Research Council of Canada and the Université de Montréal for graduate scholarships.

supplementary crystallographic information

Comment

Fluorene derivatives have found many applications in chemistry, especially in the optoelectronic area. Polymers based on the 9,9-dialkylfluorene motif possess good thermal stability along with interesting emissive properties. The quality and efficiency of OLEDs and sensors using thin films of these polymers have been shown to depend critically on the stacking of the molecules. The film-forming properties can be tailored by a judicious choice of alkyl chains, be it n-alkyl of different lengths or other branched alkyl chains. The selected alkyl groups have a profound effect on the solubility and the packing of oligo- and polyfluorenes (Scherf & List, 2002). During the process of developing new polymers, we were able to crystallize the title compound from THF/methanol.

The two alkyl chains behave quite differently in the crystal. One of them adopts a fully extended conformation with torsional angles ranging from 173.52 (12)° to 179.74 (12)°. The second octyl group incorporates a single gauche conformation (C24—C25—C26—C27, torsional angle: 70.95 (15)°), and the other torsional angles range from 171.05 (11)° to 179.67 (12)°.

In the crystal, the fluorene units are coplanar with each other and the octyl chains are extended perpendicular to the aromatic plane. The fluorene units are thereby isolated from one another by the octyl groups, as well as the pinacol groups, and no π-π interactions are present.

Experimental

The title compound was prepared according to Cho et al. (2007) from the corresponding 2,7-dibromo-9,9-dioctylfluorene. Purified material was obtained by recrystallization from THF/methanol. Spectroscopic data are consistent with the reported values.

Refinement

Non-H atoms were refined anisotropicaly. H atoms were placed in idealized positions and allowed to ride on their parent atoms with C—H distances of 0.98 Å (methylene), 0.99 Å (methyl), and 0.95 Å (aromatic C—H) and with Uiso of 1.2 times Ueq(C) for aromatic and methylene H atoms and 1.5 times Ueq(C) for terminal methyl groups. One of the pinacolatoboronate moieties is disordered over two positions in a 1:1 ratio as determined crystallographically. All the C—CH3 bonds in the disordered and the non-disordered pinacolatoboronates were restrained to be of similar length (SADI restraints with default standard deviations).

Figures

Fig. 1.
A view of the molecular structure showing the disorder. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are omitted for clarity.
Fig. 2.
A view of a 2x2x2 array of unit cells showing the coplanar fluorene units and the perpendicular octyl groups. Hydrogen atoms are omitted for clarity.

Crystal data

C41H64B2O4Z = 2
Mr = 642.54F000 = 704
Triclinic, P1Dx = 1.084 Mg m3
Hall symbol: -P 1Cu Kα radiation λ = 1.54178 Å
a = 12.6694 (12) ÅCell parameters from 17842 reflections
b = 13.3457 (11) Åθ = 3.4–68.2º
c = 14.0819 (11) ŵ = 0.51 mm1
α = 68.944 (3)ºT = 150 K
β = 89.834 (4)ºNeedle, colorless
γ = 64.306 (4)º0.10 × 0.10 × 0.05 mm
V = 1968.9 (3) Å3

Data collection

Bruker Microstar diffractometer6210 independent reflections
Radiation source: Rotating anode5656 reflections with I > 2σ(I)
Monochromator: Helios opticsRint = 0.054
Detector resolution: 8.3 pixels mm-1θmax = 68.4º
T = 150 Kθmin = 3.4º
ω scansh = −14→14
Absorption correction: multi-scan(SADABS; Sheldrick, 2007)k = −16→16
Tmin = 0.840, Tmax = 0.975l = −16→16
30971 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.104  w = 1/[σ2(Fo2) + (0.0516P)2 + 0.5043P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
6210 reflectionsΔρmax = 0.24 e Å3
476 parametersΔρmin = −0.18 e Å3
66 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

Experimental. X-ray crystallographic data for the title compound were collected from a single-crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Microstar diffractometer equiped with a platinum-135 CCD detector, Helios optics and a Kappa goniometer. The crystal-to-detector distance was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode. The initial unit-cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 10.0 degree scan in 33 frames over three different parts of the reciprocal space (99 frames total).Due to geometrical constraints of the instrument and the use of copper radiation, we consistently obtain a data completeness lower than 100% depending on the crystal system and the orientation of the mounted crystal, even with appropriate data collection routines. Typical values for data completeness range from 83–92% for triclinic systems, 85–97% for monoclinic systems and 85–98% for all other crystal systems.
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 torsional 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 and 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*/UeqOcc. (<1)
C10.56768 (12)0.24345 (11)0.09947 (8)0.0236 (3)
H10.52100.31460.03960.028*
C20.53181 (12)0.15288 (11)0.13794 (9)0.0250 (3)
C30.60214 (12)0.04909 (11)0.22662 (9)0.0257 (3)
H30.5784−0.01270.25330.031*
C40.70461 (12)0.03441 (11)0.27598 (8)0.0241 (3)
H40.7510−0.03620.33630.029*
C50.93575 (12)0.05491 (10)0.35318 (8)0.0233 (3)
H50.9415−0.02090.39770.028*
C61.02058 (12)0.08874 (11)0.36965 (8)0.0240 (3)
H61.08490.03520.42640.029*
C71.01437 (12)0.19971 (11)0.30503 (8)0.0232 (3)
C80.92079 (12)0.27689 (10)0.22061 (8)0.0227 (3)
H80.91610.35180.17500.027*
C90.72596 (11)0.31471 (10)0.11887 (8)0.0215 (3)
C100.67001 (11)0.22972 (10)0.14792 (8)0.0207 (3)
C110.73907 (11)0.12504 (10)0.23588 (8)0.0207 (3)
C120.83515 (11)0.24465 (10)0.20331 (8)0.0203 (3)
C130.84225 (12)0.13397 (10)0.27035 (8)0.0205 (3)
C140.64303 (12)0.43903 (10)0.11943 (8)0.0239 (3)
H14A0.68330.49060.09720.029*
H14B0.57040.47700.06700.029*
C150.60497 (13)0.44029 (11)0.22170 (9)0.0298 (3)
H15A0.56030.39310.24310.036*
H15B0.67670.40080.27560.036*
C160.52763 (13)0.56797 (12)0.21393 (9)0.0314 (3)
H16A0.45260.60400.16500.038*
H16B0.56920.61710.18480.038*
C170.49743 (14)0.57588 (12)0.31602 (10)0.0342 (3)
H17A0.57210.53160.36740.041*
H17B0.44780.53480.34120.041*
C180.43181 (14)0.70437 (12)0.31007 (10)0.0340 (3)
H18A0.35360.74660.26370.041*
H18B0.47800.74790.27920.041*
C190.41195 (13)0.71020 (12)0.41468 (10)0.0317 (3)
H19A0.36150.67110.44340.038*
H19B0.48980.66310.46230.038*
C200.35339 (14)0.83778 (12)0.41154 (10)0.0332 (3)
H20A0.27510.88500.36460.040*
H20B0.40350.87740.38290.040*
C210.33548 (15)0.84006 (13)0.51746 (10)0.0375 (3)
H21A0.28070.80700.54380.056*
H21B0.30190.92370.51200.056*
H21C0.41230.79090.56510.056*
C220.75963 (12)0.33564 (11)0.01037 (8)0.0235 (3)
H22A0.68530.3884−0.04180.028*
H22B0.80660.38050.00020.028*
C230.82984 (12)0.22350 (11)−0.01143 (9)0.0265 (3)
H23A0.78030.1827−0.00990.032*
H23B0.90130.16650.04340.032*
C240.86801 (13)0.25496 (11)−0.11621 (9)0.0286 (3)
H24A0.79570.3114−0.17030.034*
H24B0.91510.2983−0.11760.034*
C250.94119 (14)0.14749 (12)−0.14342 (10)0.0321 (3)
H25A0.89050.1109−0.15210.038*
H25B1.00780.0857−0.08510.038*
C260.99199 (13)0.18016 (13)−0.24185 (10)0.0327 (3)
H26A1.03320.2269−0.23680.039*
H26B1.05240.1043−0.24570.039*
C270.90085 (13)0.25322 (13)−0.34141 (10)0.0316 (3)
H27A0.83380.3226−0.33370.038*
H27B0.86890.2017−0.35260.038*
C280.95019 (14)0.30120 (13)−0.43650 (10)0.0356 (3)
H28A0.98240.3525−0.42550.043*
H28B1.01680.2320−0.44470.043*
C290.85806 (17)0.37435 (17)−0.53490 (11)0.0515 (4)
H29A0.82870.3229−0.54830.077*
H29B0.89420.4046−0.59290.077*
H29C0.79160.4429−0.52730.077*
B11.10946 (14)0.23555 (12)0.32833 (10)0.0240 (3)
O11.18801 (8)0.17591 (8)0.41961 (6)0.0272 (2)
O21.12260 (8)0.33030 (8)0.25940 (6)0.0298 (2)
C301.27671 (12)0.21973 (11)0.40392 (9)0.0276 (3)
C311.20716 (13)0.34677 (11)0.31416 (9)0.0285 (3)
C321.37874 (14)0.13171 (13)0.37341 (11)0.0365 (3)
H32A1.40930.05000.42770.055*
H32B1.44240.15550.36450.055*
H32C1.35080.13250.30820.055*
C331.31708 (15)0.22104 (14)0.50430 (10)0.0392 (4)
H33A1.24730.26460.53040.059*
H33B1.36730.26170.49210.059*
H33C1.36280.13760.55540.059*
C341.13448 (15)0.44551 (13)0.35113 (12)0.0420 (4)
H34A1.08040.51900.29180.063*
H34B1.18800.46290.38510.063*
H34C1.08790.41850.40040.063*
C351.28192 (15)0.38512 (14)0.23982 (11)0.0406 (4)
H35A1.32040.32510.20990.061*
H35B1.34290.39090.27700.061*
H35C1.23090.46420.18440.061*
B20.41847 (15)0.16668 (14)0.08183 (11)0.0293 (3)
O30.34863 (9)0.26417 (9)−0.00506 (7)0.0386 (3)
O40.38022 (11)0.08195 (11)0.11362 (8)0.0570 (4)
C400.27486 (13)0.12168 (13)0.04290 (10)0.0342 (3)
C410.2640 (4)0.2354 (5)−0.0494 (4)0.0418 (13)0.50
C420.1873 (4)0.1423 (5)0.1132 (4)0.0574 (13)0.50
H42A0.21080.06680.17410.086*0.50
H42B0.10810.16890.07670.086*0.50
H42C0.18540.20490.13510.086*0.50
C430.2789 (4)0.0205 (4)0.0104 (3)0.0477 (10)0.50
H43A0.3469−0.0050−0.02440.072*0.50
H43B0.20500.0517−0.03700.072*0.50
H43C0.2874−0.04900.07200.072*0.50
C440.3127 (4)0.2093 (4)−0.1412 (2)0.0567 (10)0.50
H44A0.26270.1858−0.17210.085*0.50
H44B0.39440.1432−0.11800.085*0.50
H44C0.31230.2822−0.19270.085*0.50
C450.1452 (3)0.3420 (3)−0.0827 (2)0.0726 (13)0.50
H45A0.11740.3591−0.02260.109*0.50
H45B0.08920.3255−0.11450.109*0.50
H45C0.15020.4123−0.13320.109*0.50
C510.2427 (3)0.2582 (3)−0.0269 (3)0.0366 (14)0.50
C520.3241 (3)0.0379 (3)−0.0098 (3)0.0570 (11)0.50
H52A0.38830.0493−0.04330.085*0.50
H52B0.26110.0547−0.06210.085*0.50
H52C0.3557−0.04580.04100.085*0.50
C530.1733 (4)0.1101 (4)0.0946 (3)0.0471 (10)0.50
H53A0.20000.02540.14160.071*0.50
H53B0.10630.13590.04180.071*0.50
H53C0.14810.16130.13410.071*0.50
C540.2145 (4)0.2935 (4)−0.1432 (2)0.0562 (10)0.50
H54A0.14560.2829−0.15880.084*0.50
H54B0.28340.2419−0.16490.084*0.50
H54C0.19630.3785−0.18040.084*0.50
C550.1435 (3)0.3527 (3)0.0019 (3)0.0493 (8)0.50
H55A0.13730.4328−0.03790.074*0.50
H55B0.16160.33260.07600.074*0.50
H55C0.06780.3535−0.01390.074*0.50

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0205 (9)0.0247 (6)0.0235 (5)−0.0087 (6)0.0025 (5)−0.0095 (5)
C20.0217 (9)0.0297 (6)0.0270 (6)−0.0125 (6)0.0066 (5)−0.0141 (5)
C30.0251 (9)0.0273 (6)0.0287 (6)−0.0149 (6)0.0074 (5)−0.0119 (5)
C40.0233 (9)0.0231 (6)0.0234 (5)−0.0101 (6)0.0043 (5)−0.0077 (4)
C50.0232 (9)0.0217 (6)0.0216 (5)−0.0088 (6)0.0031 (5)−0.0073 (4)
C60.0185 (8)0.0260 (6)0.0222 (5)−0.0063 (6)0.0000 (5)−0.0088 (5)
C70.0196 (9)0.0268 (6)0.0245 (5)−0.0096 (6)0.0052 (5)−0.0130 (5)
C80.0214 (9)0.0229 (6)0.0237 (5)−0.0102 (6)0.0044 (5)−0.0092 (4)
C90.0193 (8)0.0226 (6)0.0219 (5)−0.0096 (6)0.0011 (5)−0.0082 (4)
C100.0188 (8)0.0222 (6)0.0216 (5)−0.0084 (6)0.0046 (5)−0.0108 (4)
C110.0176 (8)0.0229 (6)0.0217 (5)−0.0076 (6)0.0053 (5)−0.0113 (4)
C120.0173 (8)0.0212 (6)0.0204 (5)−0.0065 (6)0.0036 (4)−0.0092 (4)
C130.0185 (8)0.0223 (6)0.0212 (5)−0.0081 (6)0.0054 (5)−0.0109 (4)
C140.0210 (9)0.0215 (6)0.0249 (5)−0.0078 (6)−0.0007 (5)−0.0072 (4)
C150.0295 (10)0.0273 (6)0.0282 (6)−0.0092 (7)0.0042 (5)−0.0113 (5)
C160.0303 (10)0.0291 (7)0.0314 (6)−0.0094 (7)0.0041 (5)−0.0137 (5)
C170.0331 (10)0.0311 (7)0.0328 (7)−0.0087 (7)0.0051 (6)−0.0145 (5)
C180.0335 (10)0.0319 (7)0.0352 (7)−0.0118 (7)0.0078 (6)−0.0159 (5)
C190.0289 (10)0.0318 (7)0.0338 (6)−0.0119 (7)0.0051 (6)−0.0152 (5)
C200.0315 (10)0.0324 (7)0.0365 (7)−0.0134 (7)0.0073 (6)−0.0165 (5)
C210.0364 (11)0.0381 (7)0.0406 (7)−0.0149 (8)0.0090 (6)−0.0213 (6)
C220.0226 (9)0.0247 (6)0.0211 (5)−0.0113 (6)0.0013 (5)−0.0064 (4)
C230.0267 (9)0.0276 (6)0.0264 (6)−0.0136 (6)0.0061 (5)−0.0106 (5)
C240.0294 (9)0.0286 (6)0.0278 (6)−0.0133 (7)0.0069 (5)−0.0115 (5)
C250.0323 (10)0.0300 (7)0.0331 (6)−0.0128 (7)0.0072 (6)−0.0138 (5)
C260.0263 (10)0.0363 (7)0.0386 (7)−0.0124 (7)0.0104 (6)−0.0210 (6)
C270.0291 (10)0.0383 (7)0.0358 (7)−0.0178 (7)0.0118 (6)−0.0209 (6)
C280.0365 (10)0.0407 (8)0.0377 (7)−0.0202 (8)0.0149 (6)−0.0213 (6)
C290.0543 (13)0.0691 (11)0.0356 (8)−0.0324 (10)0.0137 (7)−0.0207 (7)
B10.0188 (10)0.0247 (7)0.0265 (6)−0.0073 (7)0.0037 (5)−0.0114 (5)
O10.0236 (6)0.0306 (4)0.0277 (4)−0.0162 (5)0.0006 (3)−0.0074 (3)
O20.0279 (6)0.0305 (5)0.0287 (4)−0.0156 (5)−0.0011 (4)−0.0066 (3)
C300.0235 (9)0.0320 (7)0.0304 (6)−0.0174 (7)0.0021 (5)−0.0100 (5)
C310.0256 (9)0.0297 (6)0.0328 (6)−0.0157 (7)0.0030 (5)−0.0112 (5)
C320.0249 (10)0.0343 (7)0.0475 (8)−0.0123 (7)0.0028 (6)−0.0149 (6)
C330.0393 (11)0.0523 (9)0.0341 (7)−0.0302 (8)0.0022 (6)−0.0146 (6)
C340.0408 (11)0.0331 (7)0.0560 (9)−0.0175 (8)0.0090 (7)−0.0214 (7)
C350.0439 (11)0.0407 (8)0.0404 (7)−0.0273 (8)0.0093 (6)−0.0099 (6)
B20.0267 (11)0.0344 (8)0.0309 (7)−0.0167 (8)0.0060 (6)−0.0142 (6)
O30.0326 (7)0.0420 (5)0.0403 (5)−0.0225 (5)−0.0063 (4)−0.0089 (4)
O40.0524 (9)0.0579 (7)0.0546 (6)−0.0432 (7)−0.0193 (5)0.0065 (5)
C400.0263 (10)0.0481 (8)0.0398 (7)−0.0229 (8)0.0056 (6)−0.0228 (6)
C410.039 (3)0.049 (2)0.042 (3)−0.027 (2)−0.007 (2)−0.014 (2)
C420.042 (3)0.094 (4)0.066 (2)−0.041 (3)0.0252 (19)−0.052 (2)
C430.050 (3)0.057 (2)0.056 (2)−0.034 (2)0.0127 (18)−0.0325 (17)
C440.072 (3)0.082 (3)0.0359 (16)−0.054 (3)0.0092 (16)−0.0217 (17)
C450.046 (3)0.055 (2)0.102 (3)−0.020 (2)−0.024 (3)−0.020 (2)
C510.032 (3)0.057 (3)0.027 (2)−0.029 (2)−0.0033 (17)−0.0129 (16)
C520.042 (3)0.074 (3)0.080 (3)−0.030 (3)0.014 (2)−0.053 (2)
C530.038 (3)0.063 (3)0.053 (2)−0.033 (2)0.0109 (17)−0.0237 (18)
C540.046 (3)0.090 (3)0.0381 (18)−0.037 (3)0.0048 (16)−0.0247 (18)
C550.034 (2)0.0430 (17)0.065 (2)−0.0124 (17)0.0016 (16)−0.0215 (15)

Geometric parameters (Å, °)

C1—C101.3744 (17)C28—C291.512 (2)
C1—C21.4020 (16)C28—H28a0.99
C1—H10.95C28—H28b0.99
C2—C31.4019 (17)C29—H29a0.98
C2—B21.547 (2)C29—H29b0.98
C3—C41.3761 (18)C29—H29c0.98
C3—H30.95B1—O11.3644 (16)
C4—C111.3921 (16)B1—O21.3670 (16)
C4—H40.95O1—C301.4591 (14)
C5—C61.3821 (17)O2—C311.4564 (14)
C5—C131.3845 (17)C30—C321.509 (2)
C5—H50.95C30—C331.5132 (17)
C6—C71.3996 (16)C30—C311.5555 (17)
C6—H60.95C31—C351.5115 (18)
C7—C81.3961 (17)C31—C341.5145 (19)
C7—B11.5500 (18)C32—H32a0.98
C8—C121.3796 (16)C32—H32b0.98
C8—H80.95C32—H32c0.98
C9—C121.5136 (16)C33—H33a0.98
C9—C101.5226 (15)C33—H33b0.98
C9—C141.5344 (17)C33—H33c0.98
C9—C221.5451 (15)C34—H34a0.98
C10—C111.3981 (16)C34—H34b0.98
C11—C131.4625 (17)C34—H34c0.98
C12—C131.4016 (15)C35—H35a0.98
C14—C151.5208 (16)C35—H35b0.98
C14—H14a0.99C35—H35c0.98
C14—H14b0.99B2—O41.3505 (17)
C15—C161.5148 (18)B2—O31.3554 (18)
C15—H15a0.99O3—C511.420 (4)
C15—H15b0.99O3—C411.490 (5)
C16—C171.5149 (17)O4—C401.4385 (17)
C16—H16a0.99C40—C521.476 (3)
C16—H16b0.99C40—C421.486 (4)
C17—C181.5165 (18)C40—C531.515 (4)
C17—H17a0.99C40—C411.553 (6)
C17—H17b0.99C40—C431.555 (4)
C18—C191.5175 (17)C40—C511.588 (5)
C18—H18a0.99C41—C451.476 (6)
C18—H18b0.99C41—C441.518 (6)
C19—C201.5173 (18)C42—H42a0.98
C19—H19a0.99C42—H42b0.98
C19—H19b0.99C42—H42c0.98
C20—C211.5173 (18)C43—H43a0.98
C20—H20a0.99C43—H43b0.98
C20—H20b0.99C43—H43c0.98
C21—H21a0.98C44—H44a0.98
C21—H21b0.98C44—H44b0.98
C21—H21c0.98C44—H44c0.98
C22—C231.5163 (17)C45—H45a0.98
C22—H22a0.99C45—H45b0.98
C22—H22b0.99C45—H45c0.98
C23—C241.5213 (16)C51—C551.525 (4)
C23—H23a0.99C51—C541.527 (4)
C23—H23b0.99C52—H52a0.98
C24—C251.5176 (18)C52—H52b0.98
C24—H24a0.99C52—H52c0.98
C24—H24b0.99C53—H53a0.98
C25—C261.5263 (18)C53—H53b0.98
C25—H25a0.99C53—H53c0.98
C25—H25b0.99C54—H54a0.98
C26—C271.5167 (19)C54—H54b0.98
C26—H26a0.99C54—H54c0.98
C26—H26b0.99C55—H55a0.98
C27—C281.5232 (17)C55—H55b0.98
C27—H27a0.99C55—H55c0.98
C27—H27b0.99
C10—C1—C2120.31 (11)C26—C27—H27B108.8
C10—C1—H1119.8C28—C27—H27B108.8
C2—C1—H1119.8H27A—C27—H27B107.7
C3—C2—C1118.56 (11)C29—C28—C27113.15 (13)
C3—C2—B2121.07 (11)C29—C28—H28A108.9
C1—C2—B2120.36 (11)C27—C28—H28A108.9
C4—C3—C2121.69 (11)C29—C28—H28B108.9
C4—C3—H3119.2C27—C28—H28B108.9
C2—C3—H3119.2H28A—C28—H28B107.8
C3—C4—C11118.76 (11)C28—C29—H29A109.5
C3—C4—H4120.6C28—C29—H29B109.5
C11—C4—H4120.6H29A—C29—H29B109.5
C6—C5—C13118.51 (10)C28—C29—H29C109.5
C6—C5—H5120.7H29A—C29—H29C109.5
C13—C5—H5120.7H29B—C29—H29C109.5
C5—C6—C7121.84 (11)O1—B1—O2113.40 (11)
C5—C6—H6119.1O1—B1—C7123.37 (11)
C7—C6—H6119.1O2—B1—C7123.22 (11)
C8—C7—C6118.70 (11)B1—O1—C30106.64 (9)
C8—C7—B1121.23 (10)B1—O2—C31107.00 (9)
C6—C7—B1120.07 (11)O1—C30—C32106.27 (10)
C12—C8—C7120.16 (10)O1—C30—C33108.77 (10)
C12—C8—H8119.9C32—C30—C33110.82 (12)
C7—C8—H8119.9O1—C30—C31102.2 (1)
C12—C9—C10101.25 (9)C32—C30—C31113.08 (11)
C12—C9—C14112.05 (9)C33—C30—C31114.90 (11)
C10—C9—C14112.33 (10)O2—C31—C35108.7 (1)
C12—C9—C22111.71 (10)O2—C31—C34106.72 (11)
C10—C9—C22111.77 (8)C35—C31—C34110.49 (11)
C14—C9—C22107.75 (9)O2—C31—C30102.19 (9)
C1—C10—C11120.07 (10)C35—C31—C30114.80 (12)
C1—C10—C9129.04 (10)C34—C31—C30113.20 (11)
C11—C10—C9110.88 (10)C30—C32—H32A109.5
C4—C11—C10120.61 (11)C30—C32—H32B109.5
C4—C11—C13130.94 (11)H32A—C32—H32B109.5
C10—C11—C13108.45 (10)C30—C32—H32C109.5
C8—C12—C13119.99 (11)H32A—C32—H32C109.5
C8—C12—C9128.97 (10)H32B—C32—H32C109.5
C13—C12—C9111.03 (10)C30—C33—H33A109.5
C5—C13—C12120.78 (11)C30—C33—H33B109.5
C5—C13—C11130.84 (10)H33A—C33—H33B109.5
C12—C13—C11108.38 (10)C30—C33—H33C109.5
C15—C14—C9116.62 (9)H33A—C33—H33C109.5
C15—C14—H14A108.1H33B—C33—H33C109.5
C9—C14—H14A108.1C31—C34—H34A109.5
C15—C14—H14B108.1C31—C34—H34B109.5
C9—C14—H14B108.1H34A—C34—H34B109.5
H14A—C14—H14B107.3C31—C34—H34C109.5
C16—C15—C14111.84 (10)H34A—C34—H34C109.5
C16—C15—H15A109.2H34B—C34—H34C109.5
C14—C15—H15A109.2C31—C35—H35A109.5
C16—C15—H15B109.2C31—C35—H35B109.5
C14—C15—H15B109.2H35A—C35—H35B109.5
H15A—C15—H15B107.9C31—C35—H35C109.5
C15—C16—C17114.23 (10)H35A—C35—H35C109.5
C15—C16—H16A108.7H35B—C35—H35C109.5
C17—C16—H16A108.7O4—B2—O3113.26 (12)
C15—C16—H16B108.7O4—B2—C2123.36 (12)
C17—C16—H16B108.7O3—B2—C2123.36 (11)
H16A—C16—H16B107.6B2—O3—C51109.1 (2)
C16—C17—C18114.02 (11)B2—O3—C41108.4 (2)
C16—C17—H17A108.7B2—O4—C40109.04 (11)
C18—C17—H17A108.7O4—C40—C5299.86 (16)
C16—C17—H17B108.7O4—C40—C4298.5 (2)
C18—C17—H17B108.7C52—C40—C42136.4 (2)
H17A—C17—H17B107.6O4—C40—C53114.34 (19)
C17—C18—C19113.18 (11)C52—C40—C53112.0 (2)
C17—C18—H18A108.9O4—C40—C41105.2 (2)
C19—C18—H18A108.9C52—C40—C4195.6 (3)
C17—C18—H18B108.9C42—C40—C41117.0 (3)
C19—C18—H18B108.9C53—C40—C41125.6 (3)
H18A—C18—H18B107.8O4—C40—C43112.7 (2)
C20—C19—C18114.10 (11)C42—C40—C43108.9 (2)
C20—C19—H19A108.7C53—C40—C4384.3 (2)
C18—C19—H19A108.7C41—C40—C43113.6 (3)
C20—C19—H19B108.7O4—C40—C51102.82 (14)
C18—C19—H19B108.7C52—C40—C51114.2 (2)
H19A—C19—H19B107.6C42—C40—C5199.5 (3)
C19—C20—C21112.63 (11)C53—C40—C51112.7 (3)
C19—C20—H20A109.1C43—C40—C51129.56 (19)
C21—C20—H20A109.1C45—C41—O3108.5 (4)
C19—C20—H20B109.1C45—C41—C44111.1 (4)
C21—C20—H20B109.1O3—C41—C44105.3 (4)
H20A—C20—H20B107.8C45—C41—C40115.5 (4)
C20—C21—H21A109.5O3—C41—C40101.6 (3)
C20—C21—H21B109.5C44—C41—C40113.8 (4)
H21A—C21—H21B109.5C40—C42—H42A109.5
C20—C21—H21C109.5C40—C42—H42B109.5
H21A—C21—H21C109.5C40—C42—H42C109.5
H21B—C21—H21C109.5C40—C43—H43A109.5
C23—C22—C9116.57 (9)C40—C43—H43B109.5
C23—C22—H22A108.2C40—C43—H43C109.5
C9—C22—H22A108.2O3—C51—C55106.6 (2)
C23—C22—H22B108.2O3—C51—C54108.4 (4)
C9—C22—H22B108.2C55—C51—C54108.5 (3)
H22A—C22—H22B107.3O3—C51—C40103.10 (18)
C22—C23—C24111.51 (9)C55—C51—C40114.9 (4)
C22—C23—H23A109.3C54—C51—C40114.7 (2)
C24—C23—H23A109.3C40—C52—H52A109.5
C22—C23—H23B109.3C40—C52—H52B109.5
C24—C23—H23B109.3H52A—C52—H52B109.5
H23A—C23—H23B108C40—C52—H52C109.5
C25—C24—C23115.06 (10)H52A—C52—H52C109.5
C25—C24—H24A108.5H52B—C52—H52C109.5
C23—C24—H24A108.5C40—C53—H53A109.5
C25—C24—H24B108.5C40—C53—H53B109.5
C23—C24—H24B108.5H53A—C53—H53B109.5
H24A—C24—H24B107.5C40—C53—H53C109.5
C24—C25—C26113.59 (10)H53A—C53—H53C109.5
C24—C25—H25A108.8H53B—C53—H53C109.5
C26—C25—H25A108.8C51—C54—H54A109.5
C24—C25—H25B108.8C51—C54—H54B109.5
C26—C25—H25B108.8H54A—C54—H54B109.5
H25A—C25—H25B107.7C51—C54—H54C109.5
C27—C26—C25114.93 (12)H54A—C54—H54C109.5
C27—C26—H26A108.5H54B—C54—H54C109.5
C25—C26—H26A108.5C51—C55—H55A109.5
C27—C26—H26B108.5C51—C55—H55B109.5
C25—C26—H26B108.5H55A—C55—H55B109.5
H26A—C26—H26B107.5C51—C55—H55C109.5
C26—C27—C28113.84 (12)H55A—C55—H55C109.5
C26—C27—H27A108.8H55B—C55—H55C109.5
C28—C27—H27A108.8
C10—C1—C2—C30.29 (18)C8—C7—B1—O2−13.26 (19)
C10—C1—C2—B2−178.38 (11)C6—C7—B1—O2167.36 (12)
C1—C2—C3—C4−0.13 (18)O2—B1—O1—C30−11.48 (15)
B2—C2—C3—C4178.53 (12)C7—B1—O1—C30168.66 (12)
C2—C3—C4—C11−0.43 (18)O1—B1—O2—C31−8.34 (15)
C13—C5—C6—C7−0.20 (18)C7—B1—O2—C31171.52 (12)
C5—C6—C7—C8−1.21 (18)B1—O1—C30—C32−94.09 (12)
C5—C6—C7—B1178.19 (11)B1—O1—C30—C33146.55 (12)
C6—C7—C8—C121.43 (18)B1—O1—C30—C3124.66 (12)
B1—C7—C8—C12−177.97 (11)B1—O2—C31—C35144.65 (12)
C2—C1—C10—C110.11 (18)B1—O2—C31—C34−96.17 (12)
C2—C1—C10—C9179.01 (11)B1—O2—C31—C3022.90 (13)
C12—C9—C10—C1−179.77 (12)O1—C30—C31—O2−28.65 (12)
C14—C9—C10—C160.54 (15)C32—C30—C31—O285.16 (12)
C22—C9—C10—C1−60.72 (16)C33—C30—C31—O2−146.25 (11)
C12—C9—C10—C11−0.78 (12)O1—C30—C31—C35−146.12 (10)
C14—C9—C10—C11−120.48 (11)C32—C30—C31—C35−32.31 (14)
C22—C9—C10—C11118.26 (11)C33—C30—C31—C3596.28 (14)
C3—C4—C11—C100.83 (17)O1—C30—C31—C3485.74 (12)
C3—C4—C11—C13−179.31 (12)C32—C30—C31—C34−160.45 (11)
C1—C10—C11—C4−0.68 (17)C33—C30—C31—C34−31.86 (16)
C9—C10—C11—C4−179.77 (10)C3—C2—B2—O40.1 (2)
C1—C10—C11—C13179.43 (10)C1—C2—B2—O4178.73 (13)
C9—C10—C11—C130.34 (13)C3—C2—B2—O3−178.85 (13)
C7—C8—C12—C13−0.25 (17)C1—C2—B2—O3−0.2 (2)
C7—C8—C12—C9178.66 (11)O4—B2—O3—C5110.4 (2)
C10—C9—C12—C8−178.02 (12)C2—B2—O3—C51−170.52 (17)
C14—C9—C12—C8−58.12 (16)O4—B2—O3—C41−10.8 (3)
C22—C9—C12—C862.89 (15)C2—B2—O3—C41168.2 (2)
C10—C9—C12—C130.97 (12)O3—B2—O4—C400.63 (18)
C14—C9—C12—C13120.87 (11)C2—B2—O4—C40−178.41 (12)
C22—C9—C12—C13−118.12 (10)B2—O4—C40—C52107.9 (2)
C6—C5—C13—C121.41 (17)B2—O4—C40—C42−111.8 (2)
C6—C5—C13—C11−177.92 (11)B2—O4—C40—C53−132.4 (2)
C8—C12—C13—C5−1.20 (17)B2—O4—C40—C419.2 (3)
C9—C12—C13—C5179.7 (1)B2—O4—C40—C43133.48 (19)
C8—C12—C13—C11178.26 (10)B2—O4—C40—C51−9.9 (2)
C9—C12—C13—C11−0.83 (13)B2—O3—C41—C45137.4 (4)
C4—C11—C13—C5−0.2 (2)B2—O3—C41—C44−103.6 (3)
C10—C11—C13—C5179.69 (12)B2—O3—C41—C4015.2 (3)
C4—C11—C13—C12−179.57 (12)O4—C40—C41—C45−131.7 (3)
C10—C11—C13—C120.30 (13)C42—C40—C41—C45−23.6 (5)
C12—C9—C14—C15−52.93 (14)C43—C40—C41—C45104.7 (4)
C10—C9—C14—C1560.26 (13)O4—C40—C41—O3−14.5 (3)
C22—C9—C14—C15−176.21 (10)C42—C40—C41—O393.6 (3)
C9—C14—C15—C16177.66 (11)C43—C40—C41—O3−138.2 (3)
C14—C15—C16—C17−174.02 (11)O4—C40—C41—C4498.2 (3)
C15—C16—C17—C18173.52 (12)C42—C40—C41—C44−153.8 (3)
C16—C17—C18—C19−174.97 (12)C43—C40—C41—C44−25.5 (5)
C17—C18—C19—C20176.35 (12)B2—O3—C51—C55105.8 (3)
C18—C19—C20—C21−179.74 (12)B2—O3—C51—C54−137.6 (3)
C12—C9—C22—C2363.47 (13)B2—O3—C51—C40−15.6 (2)
C10—C9—C22—C23−49.18 (15)O4—C40—C51—O315.3 (2)
C14—C9—C22—C23−173.05 (10)C52—C40—C51—O3−91.9 (2)
C9—C22—C23—C24−174.33 (10)C53—C40—C51—O3138.9 (2)
C22—C23—C24—C25178.76 (11)O4—C40—C51—C55−100.3 (2)
C23—C24—C25—C26−172.19 (11)C52—C40—C51—C55152.57 (18)
C24—C25—C26—C27−70.95 (15)C53—C40—C51—C5523.3 (3)
C25—C26—C27—C28171.05 (11)O4—C40—C51—C54132.9 (3)
C26—C27—C28—C29−179.67 (12)C52—C40—C51—C5425.8 (5)
C8—C7—B1—O1166.59 (12)C53—C40—C51—C54−103.5 (4)
C6—C7—B1—O1−12.80 (19)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2661).

References

  • Accelrys (2005). Materials Studio Accelrys Inc., Princeton, New Jersey, USA.
  • Bruker (2006). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cho, S. Y., Grimsdale, A. C., Jones, D. J., Watkins, S. E. & Holmes, A. B. (2007). J. Am. Chem. Soc.129, 11910–11911. [PubMed]
  • Maris, T. (2004). UdMX University of Montréal, Québec, Canada.
  • Scherf, U. & List, E. J. W. (2002). Adv. Mater.14, 477–487.
  • Sheldrick, G. M. (2007). SADABS. University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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