Racemic 1,2,3,4,7,8,9,10-octa­fluoro-6H,12H-5,11-methano­dibenzo[b,f][1,5]diazo­cine: an octa­fluorinated analogue of Tröger's base

Vande Velde, C.M.L.; Didier, D.; Blockhuys, F.; Sergeyev, S.

doi:10.1107/S1600536808002602

Volume 64
Part 2
Page o538
February 2008

Received 4 January 2008
Accepted 23 January 2008
Online 30 January 2008

Key indicators
Single-crystal X-ray study
T = 290 K
Mean (C-C) = 0.004 Å
R = 0.044
wR = 0.129
Data-to-parameter ratio = 9.6
Details

Racemic 1,2,3,4,7,8,9,10-octafluoro-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine: an octafluorinated analogue of Tröger's base

Christophe M. L. Vande Velde,^a Delphine Didier,^a Frank Blockhuys ^b and Sergey Sergeyev ^a ^*

^aLaboratoire de Chimie des Polymères, Université Libre de Bruxelles, CP 206/1 Boulevard du Triomphe, 1050 Bruxelles, Belgium, and ^bDepartment of Chemistry, University of Antwerp, Universiteitsplein 1, 2610 Wilrijk, Belgium
Correspondence e-mail: sserguee@ulb.ac.be

The title compound, C₁₅H₆F₈N₂, possesses a non-crystallographic twofold axis. The dihedral angle between the two benzene rings is 98.4 (2)°. The crystal structure involves intermolecular C-HF hydrogen bonds.

Related literature

For recent reviews on the chemistry of Tröger's base (Tröger, 1887; Spielman, 1935), see: Valík et al. (2005) and Dolensky et al. (2007). For related literature on the chirality of Tröger's base, see: Prelog & Wieland (1944); for molecular clefts, see: Wilcox et al. (1987) and Artacho et al. (2006) and references cited therein; for (poly)halo-substituted Tröger's base analogues, see: Jensen & Wärnmark (2001), Sergeyev & Diederich (2004), Hansson et al. (2003), Li et al. (2005) and Faroughi et al. (2006). For related literature, see: Zabrodsky et al. (1993).

Experimental

Crystal data

C₁₅H₆F₈N₂
M_r = 366.22
Monoclinic, P 2₁ /c
a = 8.075 (3) Å
b = 10.469 (2) Å
c = 17.628 (6) Å
= 117.15 (2)°
V = 1326.0 (8) Å³
Z = 4
Mo K radiation
= 0.19 mm^-1
T = 290 (1) K
0.3 × 0.2 × 0.2 mm

Data collection

Enraf-Nonius MACH3 diffractometer
Absorption correction: none
5028 measured reflections
2412 independent reflections
1353 reflections with I > 2(I)
R_int = 0.078
3 standard reflections every 73 reflections intensity decay: 4%

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.128
S = 1.03
2412 reflections
251 parameters
All H-atom parameters refined
_max = 0.20 e Å^-3
_min = -0.25 e Å^-3

Table 1
C-H F contacts (Å, °)

C-HF	C-H	HF	CF	C-HF
C13-H132F10ⁱ	0.93 (3)	2.41 (3)	3.257 (4)	151 (3)
C13-H131F1ⁱⁱ	0.98 (4)	2.46 (3)	3.287 (5)	143 (2)
C12-H122F7ⁱⁱⁱ	0.98 (3)	2.52 (3)	3.336 (4)	141 (3)
Symmetry codes: (i) $[-x, -{1\over 2}+y, {1\over 2}-z]$ , (ii) x-1, y, z, (iii) $[x, {1\over 2}-y, -{1\over 2}+z]$ .

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2080 ).

Acknowledgements

S. Sergeyev is grateful to Professor Y. Geerts (Université Libre de Bruxelles) for the opportunity to conduct an independent research programme in his laboratory and for generous financial support.

References

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organic compounds