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

Gagnon, E.; Laliberté, D.

doi:10.1107/S1600536808022496

Volume 64
Part 8
Page o1603
August 2008

Received 11 July 2008
Accepted 17 July 2008
Online 26 July 2008

Key indicators
Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.002 Å
Disorder in main residue
R = 0.039
wR = 0.105
Data-to-parameter ratio = 13.0
Details

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

Eric Gagnon ^a ^*⁺ and Dominic Laliberté ^b

^aDépartement de Chimie, Université of Montréal, CP 6128, succ. Centre-ville, Montréal, Québec, Canada H3C 3J7, and ^bSolarisChem Inc., 598 Chaline Street, St-Lazare, Québec, Canada J7T 3E8
Correspondence e-mail: eric.gagnon.2@umontreal.ca

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); Scherf & List (2002).

Experimental

Crystal data

C₄₁H₆₄B₂O₄
M_r = 642.54
Triclinic, $[P \overline 1]$
a = 12.6694 (12) Å
b = 13.3457 (11) Å
c = 14.0819 (11) Å
= 68.944 (3)°
= 89.834 (4)°
= 64.306 (4)°
V = 1968.9 (3) Å³
Z = 2
Cu K radiation
= 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) T_min = 0.840, T_max = 0.975
30971 measured reflections
6210 independent reflections
5656 reflections with I > 2(I)
R_int = 0.054

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.104
S = 1.04
6210 reflections
476 parameters
66 restraints
H-atom parameters constrained
_max = 0.24 e Å^-3
_min = -0.18 e Å^-3

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

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

Acknowledgements

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.

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.
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.

organic compounds