(6RS,9SR)-6,7-Dibromo-1,2,3,4-tetra-hydro-1,4-methano-anthracene.

The title compound, C(15)H(12)Br(2), comprises a norbornane unit having a dibromo-naphthalene 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, mol-ecules are linked by weak inter-molecular C-H⋯Br 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—H⋯Br hydrogen bond, see: Desiraju & Steiner (2001 ▶); Farrugia et al. (2007 ▶); Kuś & 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 = 352.07

Monoclinic,

a = 23.437 (3) Å

b = 6.3565 (8) Å

c = 18.416 (2) Å

β = 111.781 (2)°

V = 2547.6 (6) Å3

Z = 8

Mo Kα radiation

μ = 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 > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.144

S = 0.96

2501 reflections

154 parameters

H-atom parameters constrained

Δρmax = 1.12 e Å−3

Δρmin = −1.09 e Å−3

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 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811013572/nr2004sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013572/nr2004Isup2.hkl

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

C15H12Br2	F(000) = 1376
Mr = 352.07	Dx = 1.836 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2464 reflections
a = 23.437 (3) Å	θ = 3.3–25.5°
b = 6.3565 (8) Å	µ = 6.34 mm−1
c = 18.416 (2) Å	T = 297 K
β = 111.781 (2)°	Parallelepiped, colorless
V = 2547.6 (6) Å3	0.56 × 0.48 × 0.20 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	2501 independent reflections
Radiation source: fine-focus sealed tube	1817 reflections with I > 2σ(I)
graphite	Rint = 0.058
φ and ω scans	θmax = 26.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −19→28
Tmin = 0.399, Tmax = 1.000	k = −7→7
6895 measured reflections	l = −22→21

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H-atom parameters constrained
S = 0.96	w = 1/[σ2(Fo2) + (0.095P)2] where P = (Fo2 + 2Fc2)/3
2501 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 1.12 e Å−3
0 restraints	Δρmin = −1.09 e Å−3

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.

	x	y	z	Uiso*/Ueq
Br1	0.02569 (2)	0.67170 (9)	0.16329 (3)	0.0637 (2)
Br2	0.02816 (3)	0.21416 (10)	0.07270 (4)	0.0725 (3)
C1	0.0959 (2)	0.5881 (7)	0.1431 (2)	0.0420 (10)
C2	0.1462 (2)	0.7148 (7)	0.1649 (2)	0.0451 (10)
H2A	0.1447	0.8436	0.1881	0.054*
C3	0.2004 (2)	0.6583 (7)	0.1536 (2)	0.0406 (10)
C4	0.2517 (2)	0.7938 (7)	0.1720 (2)	0.0451 (11)
H4A	0.2510	0.9253	0.1938	0.054*
C5	0.3020 (2)	0.7309 (7)	0.1576 (2)	0.0439 (10)
C6	0.3608 (2)	0.8382 (8)	0.1631 (3)	0.0545 (13)
H6A	0.3726	0.9605	0.1979	0.065*
C7	0.3561 (2)	0.8766 (9)	0.0789 (3)	0.0583 (13)
H7A	0.3178	0.9466	0.0488	0.070*
H7B	0.3900	0.9621	0.0779	0.070*
C8	0.3584 (2)	0.6567 (8)	0.0465 (3)	0.0595 (14)
H8A	0.3932	0.6426	0.0302	0.071*
H8B	0.3209	0.6252	0.0025	0.071*
C9	0.3656 (2)	0.5124 (9)	0.1171 (3)	0.0612 (13)
H9A	0.3814	0.3705	0.1151	0.073*
C10	0.3047 (2)	0.5253 (7)	0.1275 (3)	0.0454 (10)
C11	0.2564 (2)	0.3915 (8)	0.1093 (3)	0.0513 (11)
H11A	0.2586	0.2587	0.0893	0.062*
C12	0.2025 (2)	0.4553 (6)	0.1210 (2)	0.0387 (9)
C13	0.1496 (2)	0.3277 (7)	0.0989 (3)	0.0479 (11)
H13A	0.1504	0.1961	0.0772	0.057*
C14	0.0971 (2)	0.3921 (7)	0.1085 (2)	0.0454 (10)
C15	0.4058 (2)	0.6541 (10)	0.1856 (3)	0.0692 (16)
H15A	0.4115	0.5958	0.2365	0.083*
H15B	0.4452	0.6885	0.1826	0.083*

	U11	U22	U33	U12	U13	U23
Br1	0.0470 (3)	0.0745 (4)	0.0825 (4)	−0.0007 (3)	0.0389 (3)	0.0001 (3)
Br2	0.0554 (4)	0.0786 (4)	0.0901 (5)	−0.0332 (3)	0.0345 (3)	−0.0187 (3)
C1	0.038 (2)	0.052 (3)	0.041 (2)	−0.005 (2)	0.021 (2)	0.0023 (18)
C2	0.046 (3)	0.048 (3)	0.048 (3)	−0.007 (2)	0.025 (2)	−0.0068 (19)
C3	0.043 (2)	0.045 (2)	0.038 (2)	−0.006 (2)	0.020 (2)	−0.0012 (18)
C4	0.046 (3)	0.054 (3)	0.038 (2)	−0.009 (2)	0.019 (2)	−0.0092 (18)
C5	0.037 (2)	0.056 (3)	0.038 (2)	−0.013 (2)	0.013 (2)	−0.0047 (19)
C6	0.044 (3)	0.072 (3)	0.049 (3)	−0.023 (2)	0.018 (2)	−0.011 (2)
C7	0.049 (3)	0.072 (3)	0.058 (3)	−0.009 (3)	0.024 (2)	0.008 (2)
C8	0.041 (3)	0.087 (4)	0.059 (3)	−0.011 (3)	0.028 (2)	−0.011 (3)
C9	0.041 (3)	0.065 (3)	0.084 (4)	0.004 (3)	0.031 (3)	0.007 (3)
C10	0.034 (2)	0.056 (3)	0.048 (2)	−0.001 (2)	0.017 (2)	0.003 (2)
C11	0.050 (3)	0.042 (2)	0.068 (3)	−0.001 (2)	0.030 (2)	−0.003 (2)
C12	0.039 (2)	0.041 (2)	0.039 (2)	−0.0049 (19)	0.0171 (19)	−0.0002 (17)
C13	0.052 (3)	0.040 (2)	0.059 (3)	−0.011 (2)	0.029 (2)	−0.0076 (19)
C14	0.041 (2)	0.052 (3)	0.044 (2)	−0.013 (2)	0.017 (2)	0.0022 (19)
C15	0.036 (3)	0.107 (5)	0.061 (3)	−0.003 (3)	0.013 (2)	0.019 (3)

Br1—C1	1.892 (4)	C7—H7A	0.9700
Br2—C14	1.881 (4)	C7—H7B	0.9700
C1—C2	1.359 (6)	C8—C9	1.548 (7)
C1—C14	1.405 (6)	C8—H8A	0.9700
C2—C3	1.407 (6)	C8—H8B	0.9700
C2—H2A	0.9300	C9—C10	1.512 (6)
C3—C12	1.432 (6)	C9—C15	1.552 (8)
C3—C4	1.415 (6)	C9—H9A	0.9800
C4—C5	1.363 (6)	C10—C11	1.355 (7)
C4—H4A	0.9300	C11—C12	1.417 (6)
C5—C10	1.430 (7)	C11—H11A	0.9300
C5—C6	1.506 (6)	C12—C13	1.409 (6)
C6—C15	1.526 (8)	C13—C14	1.368 (7)
C6—C7	1.533 (6)	C13—H13A	0.9300
C6—H6A	0.9800	C15—H15A	0.9700
C7—C8	1.529 (7)	C15—H15B	0.9700
C2—C1—C14	119.8 (4)	C7—C8—H8B	111.2
C2—C1—Br1	119.8 (3)	C9—C8—H8B	111.2
C14—C1—Br1	120.3 (3)	H8A—C8—H8B	109.1
C1—C2—C3	122.4 (4)	C10—C9—C8	105.1 (4)
C1—C2—H2A	118.8	C10—C9—C15	100.5 (4)
C3—C2—H2A	118.8	C8—C9—C15	100.6 (4)
C12—C3—C4	119.3 (4)	C10—C9—H9A	116.1
C12—C3—C2	117.8 (4)	C8—C9—H9A	116.1
C4—C3—C2	122.9 (4)	C15—C9—H9A	116.1
C5—C4—C3	119.7 (4)	C11—C10—C5	121.1 (4)
C5—C4—H4A	120.1	C11—C10—C9	132.6 (5)
C3—C4—H4A	120.1	C5—C10—C9	106.1 (4)
C4—C5—C10	120.6 (4)	C10—C11—C12	119.5 (4)
C4—C5—C6	133.7 (4)	C10—C11—H11A	120.2
C10—C5—C6	105.7 (4)	C12—C11—H11A	120.2
C5—C6—C15	101.2 (4)	C11—C12—C3	119.6 (4)
C5—C6—C7	106.4 (4)	C11—C12—C13	122.0 (4)
C15—C6—C7	100.4 (4)	C3—C12—C13	118.4 (4)
C5—C6—H6A	115.6	C14—C13—C12	121.8 (4)
C15—C6—H6A	115.6	C14—C13—H13A	119.1
C7—C6—H6A	115.6	C12—C13—H13A	119.1
C8—C7—C6	104.5 (4)	C13—C14—C1	119.7 (4)
C8—C7—H7A	110.9	C13—C14—Br2	118.1 (3)
C6—C7—H7A	110.9	C1—C14—Br2	122.1 (4)
C8—C7—H7B	110.9	C6—C15—C9	94.3 (4)
C6—C7—H7B	110.9	C6—C15—H15A	112.9
H7A—C7—H7B	108.9	C9—C15—H15A	112.9
C7—C8—C9	102.8 (4)	C6—C15—H15B	112.9
C7—C8—H8A	111.2	C9—C15—H15B	112.9
C9—C8—H8A	111.2	H15A—C15—H15B	110.3
C14—C1—C2—C3	0.5 (7)	C8—C9—C10—C5	−71.4 (5)
Br1—C1—C2—C3	178.0 (3)	C15—C9—C10—C5	32.6 (5)
C1—C2—C3—C12	−2.8 (6)	C5—C10—C11—C12	−0.6 (7)
C1—C2—C3—C4	176.3 (4)	C9—C10—C11—C12	−175.1 (5)
C12—C3—C4—C5	0.8 (6)	C10—C11—C12—C3	−1.5 (6)
C2—C3—C4—C5	−178.2 (4)	C10—C11—C12—C13	176.2 (4)
C3—C4—C5—C10	−2.9 (6)	C4—C3—C12—C11	1.4 (6)
C3—C4—C5—C6	173.9 (4)	C2—C3—C12—C11	−179.5 (4)
C4—C5—C6—C15	147.7 (5)	C4—C3—C12—C13	−176.3 (4)
C10—C5—C6—C15	−35.1 (5)	C2—C3—C12—C13	2.8 (6)
C4—C5—C6—C7	−107.8 (6)	C11—C12—C13—C14	−178.3 (4)
C10—C5—C6—C7	69.4 (5)	C3—C12—C13—C14	−0.6 (6)
C5—C6—C7—C8	−68.1 (5)	C12—C13—C14—C1	−1.7 (7)
C15—C6—C7—C8	36.9 (5)	C12—C13—C14—Br2	177.3 (3)
C6—C7—C8—C9	−1.0 (5)	C2—C1—C14—C13	1.8 (6)
C7—C8—C9—C10	69.5 (5)	Br1—C1—C14—C13	−175.7 (3)
C7—C8—C9—C15	−34.6 (5)	C2—C1—C14—Br2	−177.1 (3)
C4—C5—C10—C11	2.9 (7)	Br1—C1—C14—Br2	5.3 (5)
C6—C5—C10—C11	−174.7 (4)	C5—C6—C15—C9	52.5 (4)
C4—C5—C10—C9	178.7 (4)	C7—C6—C15—C9	−56.7 (4)
C6—C5—C10—C9	1.0 (5)	C10—C9—C15—C6	−51.5 (4)
C8—C9—C10—C11	103.6 (6)	C8—C9—C15—C6	56.3 (4)
C15—C9—C10—C11	−152.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···Br2i	0.97	3.00 (1)	3.843 (16)	146 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯Br2i	0.97	3.00 (1)	3.843 (16)	146 (1)

Symmetry code: (i) .