(6RS,9SR)-6,7-Dibromo-1,2,3,4-tetra­hydro-1,4-methano­anthracene

Chen, K.-Y.; Chang, M.-J.; Fang, T.-C.

doi:10.1107/S1600536811013572

Volume 67
Part 5
Page o1147
May 2011

Received 26 March 2011
Accepted 11 April 2011
Online 16 April 2011

Key indicators
Single-crystal X-ray study
T = 297 K
Mean (C-C) = 0.007 Å
R = 0.055
wR = 0.144
Data-to-parameter ratio = 16.2
Details

(6RS,9SR)-6,7-Dibromo-1,2,3,4-tetrahydro-1,4-methanoanthracene

Kew-Yu Chen,^a ^* Ming-Jen Chang ^a and Tzu-Chien Fang ^a

^aDepartment of Chemical Engineering, Feng Chia University, 40724 Taichung, Taiwan
Correspondence e-mail: kyuchen@fcu.edu.tw

The title compound, C₁₅H₁₂Br₂, comprises a norbornane unit having a dibromonaphthalene ring fused on one side. Both Br atoms are twisted slightly out of the plane of the naphthalene ring system with a Br-C-C-Br torsion angle of 5.3 (5)°. In the crystal, molecules are linked by weak intermolecular C-HBr hydrogen bonds, forming an infinite C(9) chain along [110].

Related literature

For the spectroscopy of the title compound and its preparation, see: Chen et al. (2006). For the spectroscopy and electronic device applications of rigid oligo-norbornyl compounds, see: Chen et al. (2002); Chow et al. (2005); Lewis et al. (1997); Roest et al. (1996). For related structures, see: Çelik et al. (2006); Chiou et al. (2001); Chow et al. (1999); Lough et al. (2006). For the C-HBr hydrogen bond, see: Desiraju & Steiner (2001); Farrugia et al. (2007); Kus & Jones (2003); Yang et al. (2007). For puckering parameters, see: Cremer & Pople (1975). For graph-set theory, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₅H₁₂Br₂
M_r = 352.07
Monoclinic, C 2/c
a = 23.437 (3) Å
b = 6.3565 (8) Å
c = 18.416 (2) Å
= 111.781 (2)°
V = 2547.6 (6) Å³
Z = 8
Mo K radiation
= 6.34 mm^-1
T = 297 K
0.56 × 0.48 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001) T_min = 0.399, T_max = 1.000
6895 measured reflections
2501 independent reflections
1817 reflections with I > 2(I)
R_int = 0.058

Refinement

R[F² > 2(F²)] = 0.055
wR(F²) = 0.144
S = 0.96
2501 reflections
154 parameters
H-atom parameters constrained
_max = 1.12 e Å^-3
_min = -1.09 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C8-H8ABr2ⁱ	0.97	3.00 (1)	3.843 (16)	146 (1)
Symmetry code: (i) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NR2004 ).

Acknowledgements

Financial support from the National Science Council of the Republic of China is gratefully acknowledged.

References

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organic compounds