9-Bromo-9-borafluorene

Hübner, A.; Lerner, H.-W.; Wagner, M.; Bolte, M.

doi:10.1107/S1600536810001625

organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page o444

https://doi.org/10.1107/S1600536810001625

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9-Bromo-9-borafluorene

Alexander Hübner,^a Hans-Wolfram Lerner,^a Matthias Wagner ^a and Michael Bolte ^a ^*

^aInstitut für Anorganische Chemie der Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, D-60438 Frankfurt am Main, Germany
^*Correspondence e-mail: bolte@chemie.uni-frankfurt.de

(Received 17 December 2009; accepted 13 January 2010; online 23 January 2010)

The title compound, C₁₂H₈BBr, crystallizes with three essentially planar molecules (r.m.s. deviations = 0.018, 0.020 and 0.021Å) in the asymmetric unit: since the title compound is rigid, there are no conformational differences between these three molecules. The crystal packing resembles a herringbone pattern.

Related literature

For the synthesis of 9-ferrocenyl-9-borafluorene derivatives, see: Kaufmann et al. (2008 ). The title compound was obtained by treatment of 9,9-dimethyl-9-silafluorene (Mewes et al., 2009 ) with BBr₃ following a modified literature procedure (Gross et al., 1987 ).

Experimental

Crystal data

C₁₂H₈BBr
M_r = 242.90
Orthorhombic, F d d 2
a = 34.939 (3) Å
b = 85.482 (4) Å
c = 3.9672 (2) Å
V = 11848.7 (13) Å³
Z = 48
Mo Kα radiation
μ = 4.11 mm⁻¹
T = 173 K
0.19 × 0.03 × 0.03 mm

Data collection

Stoe IPDS II two-circle diffractometer
Absorption correction: multi-scan (MULABS; Spek, 2009 ; Blessing, 1995 ) T_min = 0.509, T_max = 0.887
20875 measured reflections
5204 independent reflections
3565 reflections with I > 2σ(I)
R_int = 0.080

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.100
S = 0.86
5204 reflections
380 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.61 e Å⁻³
Absolute structure: Flack (1983 ), 2183 Friedel pairs
Flack parameter: 0.320 (19)

Data collection: X-AREA (Stoe & Cie, 2001 ); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810001625/fk2010sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810001625/fk2010Isup2.hkl

checkCIF report

Comment top

Polyferrocenylenes with bridging elements ER_x (e. g. ER_x = BR, SiR₂, SnR₂, PR, S) represent an important class of processable metal-containing polymers with applications ranging from molecular electronics to the preparation of magnetic ceramics. We are currently interested in negatively charged polyferrocenylenes with borate linkers. To this end, we have synthesized 9-ferrocenyl-9-borafluorene derivatives (Kaufmann et al., 2008) as building blocks for such polymers. Herein, we describe the preparation and solid state structure of 9-bromo-9-borafluorene (C₁₂H₈BBr), which we have already used as a starting material in the synthesis of 9-ferrocenyl-9-borafluorene derivatives. The title compound was obtained by treatment of 9,9-dimethyl-9-silafluorene (Mewes et al., 2009) with BBr₃ following a modified literature procedure (Gross et al., 1987), as indicated in the equation (Fig. 3).

The title compound (Fig. 1) crystallizes with three essentially planar molecules (r.m.s. deviation = 0.018 Å, 0.020 Å, 0.021 Å) in the asymmetric unit. Since the title compound features a rigid molecule, there are no conformational differences between these three molecules.

The crystal packing resembles a herring bone pattern (Fig. 2).

Related literature top

For the synthesis of 9-ferrocenyl-9-borafluorene derivatives, see: Kaufmann et al. (2008). The title compound was obtained by treatment of 9,9-dimethyl-9-silafluorene (Mewes et al., 2009) with BBr₃ following a modified literature procedure (Gross et al., 1987).

Experimental top

A mixture of 9,9-dimethyl-9-silafluorene (0.52 g, 2.47 mmol) and BBr₃ (0.6 ml, 1.59 g, 6.35 mmol) was heated in a sealed ampoule for 52 h at 328 K. After removal of all volatiles in vacuo, X-ray quality crystals of the title compound were obtained from a hexane solution at room temperature (yield: 0.60 g, 2.47 mmol, 100 °).

Structure description top

The crystal packing resembles a herring bone pattern (Fig. 2).

For the synthesis of 9-ferrocenyl-9-borafluorene derivatives, see: Kaufmann et al. (2008). The title compound was obtained by treatment of 9,9-dimethyl-9-silafluorene (Mewes et al., 2009) with BBr₃ following a modified literature procedure (Gross et al., 1987).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. A view of the three molecules in the asymmetric unit of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Packing diagram with view onto the bc plane. Hydrogen atoms omitted for clarity.
	Fig. 3. The formation of the title compound.

9-Bromo-9-borafluorene top

Crystal data top

C₁₂H₈BBr	F(000) = 5760
M_r = 242.90	D_x = 1.634 Mg m⁻³
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 9350 reflections
a = 34.939 (3) Å	θ = 2.4–25.3°
b = 85.482 (4) Å	µ = 4.11 mm⁻¹
c = 3.9672 (2) Å	T = 173 K
V = 11848.7 (13) Å³	Needle, yellow
Z = 48	0.19 × 0.03 × 0.03 mm

Data collection top

Stoe IPDS II two-circle diffractometer	5204 independent reflections
Radiation source: fine-focus sealed tube	3565 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.080
ω scans	θ_max = 25.1°, θ_min = 2.2°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −40→40
T_min = 0.509, T_max = 0.887	k = −100→90
20875 measured reflections	l = −4→4

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.100	w = 1/[σ²(F_o²) + (0.0328P)²] where P = (F_o² + 2F_c²)/3
S = 0.86	(Δ/σ)_max = 0.002
5204 reflections	Δρ_max = 0.46 e Å⁻³
380 parameters	Δρ_min = −0.61 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 2183 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.320 (19)

Crystal data top

C₁₂H₈BBr	V = 11848.7 (13) Å³
M_r = 242.90	Z = 48
Orthorhombic, Fdd2	Mo Kα radiation
a = 34.939 (3) Å	µ = 4.11 mm⁻¹
b = 85.482 (4) Å	T = 173 K
c = 3.9672 (2) Å	0.19 × 0.03 × 0.03 mm

Data collection top

Stoe IPDS II two-circle diffractometer	5204 independent reflections
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	3565 reflections with I > 2σ(I)
T_min = 0.509, T_max = 0.887	R_int = 0.080
20875 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.100	Δρ_max = 0.46 e Å⁻³
S = 0.86	Δρ_min = −0.61 e Å⁻³
5204 reflections	Absolute structure: Flack (1983), 2183 Friedel pairs
380 parameters	Absolute structure parameter: 0.320 (19)
1 restraint

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.57091 (3)	0.512885 (9)	0.9579 (2)	0.0389 (2)
B1	0.5914 (3)	0.49518 (11)	0.727 (2)	0.032 (2)
C1	0.5689 (2)	0.48119 (9)	0.5713 (18)	0.0265 (18)
C2	0.5971 (2)	0.47105 (9)	0.434 (2)	0.0265 (17)
C3	0.5857 (2)	0.45687 (10)	0.277 (2)	0.033 (2)
H3	0.6042	0.4499	0.1877	0.039*
C4	0.5470 (2)	0.45348 (10)	0.258 (2)	0.036 (2)
H4	0.5389	0.4440	0.1535	0.043*
C5	0.5196 (2)	0.46368 (10)	0.390 (2)	0.039 (2)
H5	0.4933	0.4611	0.3714	0.047*
C6	0.5304 (2)	0.47751 (9)	0.546 (2)	0.034 (2)
H6	0.5115	0.4844	0.6357	0.041*
C11	0.6343 (2)	0.49174 (9)	0.656 (2)	0.0298 (18)
C12	0.6363 (2)	0.47732 (8)	0.486 (2)	0.0286 (18)
C13	0.6714 (2)	0.47142 (10)	0.378 (2)	0.035 (2)
H13	0.6727	0.4618	0.2579	0.042*
C14	0.7045 (2)	0.47980 (10)	0.449 (2)	0.036 (2)
H14	0.7286	0.4758	0.3772	0.044*
C15	0.7029 (3)	0.49375 (11)	0.621 (2)	0.043 (2)
H15	0.7260	0.4993	0.6677	0.052*
C16	0.6681 (2)	0.49993 (10)	0.729 (2)	0.036 (2)
H16	0.6672	0.5095	0.8495	0.044*
Br1A	0.69438 (3)	0.598421 (10)	1.03380 (19)	0.0392 (2)
B1A	0.6694 (3)	0.58003 (12)	0.884 (2)	0.031 (2)
C1A	0.6268 (2)	0.57608 (9)	0.914 (2)	0.0327 (19)
C2A	0.6208 (2)	0.56131 (9)	0.758 (2)	0.0249 (17)
C3A	0.5844 (2)	0.55494 (9)	0.739 (2)	0.033 (2)
H3A	0.5804	0.5452	0.6286	0.040*
C4A	0.5537 (2)	0.56287 (10)	0.882 (2)	0.038 (2)
H4A	0.5287	0.5585	0.8700	0.046*
C5A	0.5592 (2)	0.57729 (10)	1.045 (2)	0.038 (2)
H5A	0.5382	0.5825	1.1473	0.046*
C6A	0.5955 (2)	0.58378 (10)	1.055 (2)	0.034 (2)
H6A	0.5991	0.5937	1.1591	0.040*
C11A	0.6880 (2)	0.56560 (8)	0.705 (2)	0.0293 (18)
C12A	0.6578 (2)	0.55499 (9)	0.631 (2)	0.0257 (19)
C13A	0.6650 (2)	0.54106 (9)	0.464 (2)	0.0334 (19)
H13A	0.6447	0.5341	0.4107	0.040*
C14A	0.7021 (3)	0.53746 (10)	0.375 (2)	0.035 (2)
H14A	0.7073	0.5277	0.2690	0.041*
C15A	0.7320 (2)	0.54767 (9)	0.438 (3)	0.038 (2)
H15A	0.7572	0.5451	0.3690	0.045*
C16A	0.7247 (2)	0.56172 (10)	0.603 (2)	0.036 (2)
H16A	0.7452	0.5687	0.6472	0.043*
Br1B	0.57408 (3)	0.680334 (9)	−0.0716 (3)	0.0384 (2)
B1B	0.5983 (3)	0.66204 (11)	0.112 (2)	0.030 (2)
C1B	0.6416 (2)	0.65923 (9)	0.1237 (19)	0.027 (2)
C2B	0.6472 (2)	0.64463 (9)	0.291 (2)	0.0259 (18)
C3B	0.6835 (2)	0.63877 (11)	0.351 (2)	0.033 (2)
H3B	0.6869	0.6292	0.4701	0.040*
C4B	0.7149 (2)	0.64705 (11)	0.235 (2)	0.038 (2)
H4B	0.7399	0.6430	0.2698	0.046*
C5B	0.7102 (2)	0.66116 (10)	0.068 (2)	0.034 (2)
H5B	0.7320	0.6667	−0.0107	0.041*
C6B	0.6739 (2)	0.66719 (9)	0.014 (2)	0.035 (2)
H6B	0.6711	0.6769	−0.0992	0.042*
C11B	0.5793 (2)	0.64763 (9)	0.276 (2)	0.0284 (18)
C12B	0.6090 (2)	0.63775 (9)	0.3814 (19)	0.0258 (19)
C13B	0.6010 (2)	0.62372 (9)	0.542 (2)	0.0292 (18)
H13B	0.6212	0.6171	0.6162	0.035*
C14B	0.5630 (2)	0.61940 (10)	0.593 (2)	0.032 (2)
H14B	0.5572	0.6097	0.6970	0.039*
C15B	0.5334 (2)	0.62921 (9)	0.493 (2)	0.0304 (19)
H15B	0.5076	0.6262	0.5320	0.036*
C16B	0.5409 (2)	0.64345 (10)	0.336 (2)	0.033 (2)
H16B	0.5206	0.6502	0.2718	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0557 (5)	0.0268 (4)	0.0342 (5)	0.0070 (4)	0.0007 (5)	−0.0021 (5)
B1	0.048 (6)	0.031 (5)	0.017 (5)	−0.004 (4)	−0.004 (4)	0.007 (4)
C1	0.030 (4)	0.022 (4)	0.028 (4)	0.000 (3)	−0.001 (4)	0.002 (3)
C2	0.034 (4)	0.021 (4)	0.025 (4)	−0.003 (3)	−0.002 (4)	0.002 (4)
C3	0.039 (5)	0.029 (4)	0.031 (5)	0.007 (4)	−0.004 (4)	0.004 (4)
C4	0.043 (5)	0.026 (4)	0.039 (6)	−0.001 (4)	−0.008 (5)	0.001 (4)
C5	0.029 (4)	0.038 (5)	0.049 (6)	−0.003 (4)	−0.006 (4)	0.010 (5)
C6	0.041 (5)	0.028 (4)	0.033 (5)	0.002 (4)	0.006 (4)	0.007 (4)
C11	0.042 (5)	0.027 (4)	0.020 (4)	0.004 (3)	0.000 (4)	0.010 (4)
C12	0.042 (5)	0.020 (4)	0.023 (5)	0.004 (3)	−0.002 (4)	0.006 (4)
C13	0.041 (5)	0.024 (4)	0.039 (6)	0.003 (4)	0.005 (4)	0.016 (4)
C14	0.029 (5)	0.046 (5)	0.034 (5)	0.003 (4)	0.004 (4)	0.009 (5)
C15	0.045 (6)	0.045 (6)	0.039 (6)	−0.012 (4)	−0.012 (4)	0.017 (5)
C16	0.038 (5)	0.035 (4)	0.037 (5)	−0.004 (3)	−0.005 (5)	−0.001 (5)
Br1A	0.0505 (5)	0.0286 (4)	0.0386 (5)	−0.0069 (4)	−0.0025 (4)	−0.0062 (4)
B1A	0.043 (6)	0.039 (5)	0.012 (5)	0.004 (4)	−0.004 (4)	0.004 (4)
C1A	0.040 (5)	0.023 (4)	0.036 (5)	0.001 (3)	−0.003 (4)	0.010 (4)
C2A	0.026 (4)	0.032 (4)	0.017 (4)	−0.002 (3)	−0.003 (3)	0.007 (4)
C3A	0.039 (5)	0.025 (4)	0.034 (5)	0.003 (3)	−0.015 (4)	0.006 (4)
C4A	0.031 (4)	0.041 (5)	0.042 (6)	−0.002 (4)	0.007 (4)	0.008 (4)
C5A	0.040 (5)	0.043 (5)	0.032 (5)	0.012 (4)	0.007 (4)	0.009 (4)
C6A	0.039 (5)	0.032 (4)	0.029 (5)	0.010 (4)	−0.003 (4)	0.004 (4)
C11A	0.032 (4)	0.022 (4)	0.034 (4)	0.001 (3)	−0.003 (4)	−0.002 (4)
C12A	0.029 (4)	0.020 (4)	0.028 (5)	0.003 (3)	−0.005 (4)	0.003 (3)
C13A	0.044 (5)	0.023 (4)	0.033 (5)	0.001 (4)	−0.002 (4)	−0.002 (4)
C14A	0.050 (5)	0.027 (4)	0.027 (5)	0.002 (4)	0.003 (4)	−0.003 (4)
C15A	0.044 (5)	0.028 (4)	0.040 (5)	0.015 (4)	0.002 (5)	−0.001 (5)
C16A	0.035 (5)	0.031 (5)	0.043 (6)	−0.008 (4)	−0.001 (4)	0.002 (4)
Br1B	0.0501 (5)	0.0283 (4)	0.0369 (5)	0.0083 (4)	0.0004 (4)	0.0072 (5)
B1B	0.031 (5)	0.034 (5)	0.026 (6)	0.002 (4)	−0.003 (4)	0.000 (4)
C1B	0.031 (4)	0.029 (4)	0.023 (5)	−0.004 (3)	−0.004 (3)	0.003 (3)
C2B	0.036 (4)	0.023 (4)	0.018 (4)	0.005 (3)	−0.002 (4)	0.000 (4)
C3B	0.033 (5)	0.033 (5)	0.033 (5)	0.004 (4)	0.000 (4)	−0.001 (4)
C4B	0.024 (4)	0.059 (6)	0.032 (5)	0.003 (4)	−0.003 (4)	−0.013 (5)
C5B	0.032 (5)	0.040 (5)	0.030 (5)	−0.007 (4)	0.000 (4)	−0.008 (4)
C6B	0.043 (5)	0.027 (4)	0.035 (5)	−0.004 (4)	0.005 (5)	−0.011 (4)
C11B	0.029 (4)	0.034 (4)	0.022 (4)	0.001 (3)	−0.003 (4)	0.000 (4)
C12B	0.031 (4)	0.023 (4)	0.024 (5)	0.001 (3)	0.000 (4)	−0.005 (4)
C13B	0.035 (5)	0.020 (4)	0.033 (5)	0.006 (3)	−0.005 (4)	0.000 (4)
C14B	0.046 (5)	0.023 (4)	0.028 (5)	−0.002 (4)	0.004 (4)	0.001 (3)
C15B	0.030 (4)	0.027 (4)	0.034 (5)	−0.012 (4)	0.002 (4)	−0.005 (4)
C16B	0.040 (5)	0.030 (4)	0.029 (5)	0.004 (4)	−0.002 (4)	−0.002 (4)

Geometric parameters (Å, º) top

Br1—B1	1.909 (10)	C5A—H5A	0.9500
B1—C11	1.554 (12)	C6A—H6A	0.9500
B1—C1	1.557 (12)	C11A—C16A	1.384 (11)
C1—C6	1.386 (10)	C11A—C12A	1.421 (10)
C1—C2	1.422 (11)	C12A—C13A	1.387 (11)
C2—C3	1.420 (11)	C13A—C14A	1.377 (12)
C2—C12	1.482 (10)	C13A—H13A	0.9500
C3—C4	1.387 (11)	C14A—C15A	1.382 (12)
C3—H3	0.9500	C14A—H14A	0.9500
C4—C5	1.394 (12)	C15A—C16A	1.392 (12)
C4—H4	0.9500	C15A—H15A	0.9500
C5—C6	1.387 (12)	C16A—H16A	0.9500
C5—H5	0.9500	Br1B—B1B	1.920 (10)
C6—H6	0.9500	B1B—C1B	1.534 (12)
C11—C16	1.402 (11)	B1B—C11B	1.543 (12)
C11—C12	1.408 (11)	C1B—C6B	1.387 (11)
C12—C13	1.396 (11)	C1B—C2B	1.428 (11)
C13—C14	1.388 (12)	C2B—C3B	1.384 (11)
C13—H13	0.9500	C2B—C12B	1.504 (11)
C14—C15	1.376 (13)	C3B—C4B	1.383 (12)
C14—H14	0.9500	C3B—H3B	0.9500
C15—C16	1.395 (13)	C4B—C5B	1.386 (12)
C15—H15	0.9500	C4B—H4B	0.9500
C16—H16	0.9500	C5B—C6B	1.385 (12)
Br1A—B1A	1.892 (10)	C5B—H5B	0.9500
B1A—C1A	1.533 (13)	C6B—H6B	0.9500
B1A—C11A	1.565 (12)	C11B—C12B	1.402 (10)
C1A—C6A	1.392 (11)	C11B—C16B	1.408 (11)
C1A—C2A	1.421 (11)	C12B—C13B	1.386 (11)
C2A—C3A	1.387 (10)	C13B—C14B	1.396 (11)
C2A—C12A	1.488 (11)	C13B—H13B	0.9500
C3A—C4A	1.390 (12)	C14B—C15B	1.389 (11)
C3A—H3A	0.9500	C14B—H14B	0.9500
C4A—C5A	1.404 (13)	C15B—C16B	1.391 (11)
C4A—H4A	0.9500	C15B—H15B	0.9500
C5A—C6A	1.386 (12)	C16B—H16B	0.9500

C11—B1—C1	105.7 (7)	C1A—C6A—H6A	119.4
C11—B1—Br1	126.7 (6)	C16A—C11A—C12A	118.4 (7)
C1—B1—Br1	127.6 (6)	C16A—C11A—B1A	134.8 (7)
C6—C1—C2	120.5 (7)	C12A—C11A—B1A	106.8 (7)
C6—C1—B1	133.8 (7)	C13A—C12A—C11A	120.7 (7)
C2—C1—B1	105.7 (7)	C13A—C12A—C2A	129.2 (7)
C3—C2—C1	119.5 (7)	C11A—C12A—C2A	110.1 (7)
C3—C2—C12	129.0 (7)	C14A—C13A—C12A	119.0 (8)
C1—C2—C12	111.5 (7)	C14A—C13A—H13A	120.5
C4—C3—C2	118.5 (7)	C12A—C13A—H13A	120.5
C4—C3—H3	120.7	C13A—C14A—C15A	121.6 (8)
C2—C3—H3	120.7	C13A—C14A—H14A	119.2
C3—C4—C5	121.1 (8)	C15A—C14A—H14A	119.2
C3—C4—H4	119.4	C14A—C15A—C16A	119.4 (8)
C5—C4—H4	119.4	C14A—C15A—H15A	120.3
C6—C5—C4	121.1 (8)	C16A—C15A—H15A	120.3
C6—C5—H5	119.5	C11A—C16A—C15A	120.8 (8)
C4—C5—H5	119.5	C11A—C16A—H16A	119.6
C1—C6—C5	119.2 (8)	C15A—C16A—H16A	119.6
C1—C6—H6	120.4	C1B—B1B—C11B	106.6 (7)
C5—C6—H6	120.4	C1B—B1B—Br1B	125.0 (6)
C16—C11—C12	119.7 (7)	C11B—B1B—Br1B	128.3 (6)
C16—C11—B1	132.9 (8)	C6B—C1B—C2B	117.5 (8)
C12—C11—B1	107.4 (7)	C6B—C1B—B1B	135.7 (8)
C13—C12—C11	120.4 (7)	C2B—C1B—B1B	106.7 (7)
C13—C12—C2	129.7 (7)	C3B—C2B—C1B	121.5 (8)
C11—C12—C2	109.8 (7)	C3B—C2B—C12B	129.2 (7)
C14—C13—C12	119.0 (8)	C1B—C2B—C12B	109.2 (7)
C14—C13—H13	120.5	C4B—C3B—C2B	118.9 (8)
C12—C13—H13	120.5	C4B—C3B—H3B	120.6
C15—C14—C13	121.0 (8)	C2B—C3B—H3B	120.6
C15—C14—H14	119.5	C3B—C4B—C5B	120.7 (8)
C13—C14—H14	119.5	C3B—C4B—H4B	119.6
C14—C15—C16	121.0 (8)	C5B—C4B—H4B	119.6
C14—C15—H15	119.5	C4B—C5B—C6B	120.4 (8)
C16—C15—H15	119.5	C4B—C5B—H5B	119.8
C15—C16—C11	118.9 (8)	C6B—C5B—H5B	119.8
C15—C16—H16	120.5	C5B—C6B—C1B	120.9 (8)
C11—C16—H16	120.5	C5B—C6B—H6B	119.5
C1A—B1A—C11A	105.3 (7)	C1B—C6B—H6B	119.5
C1A—B1A—Br1A	127.3 (6)	C12B—C11B—C16B	120.0 (7)
C11A—B1A—Br1A	127.4 (6)	C12B—C11B—B1B	106.8 (6)
C6A—C1A—C2A	118.6 (7)	C16B—C11B—B1B	133.2 (7)
C6A—C1A—B1A	133.7 (8)	C13B—C12B—C11B	120.7 (7)
C2A—C1A—B1A	107.7 (7)	C13B—C12B—C2B	128.7 (7)
C3A—C2A—C1A	120.5 (7)	C11B—C12B—C2B	110.6 (7)
C3A—C2A—C12A	129.4 (7)	C12B—C13B—C14B	119.1 (7)
C1A—C2A—C12A	110.1 (6)	C12B—C13B—H13B	120.4
C2A—C3A—C4A	119.6 (8)	C14B—C13B—H13B	120.4
C2A—C3A—H3A	120.2	C15B—C14B—C13B	120.5 (7)
C4A—C3A—H3A	120.2	C15B—C14B—H14B	119.8
C3A—C4A—C5A	120.8 (8)	C13B—C14B—H14B	119.8
C3A—C4A—H4A	119.6	C14B—C15B—C16B	121.1 (7)
C5A—C4A—H4A	119.6	C14B—C15B—H15B	119.5
C6A—C5A—C4A	119.2 (8)	C16B—C15B—H15B	119.5
C6A—C5A—H5A	120.4	C15B—C16B—C11B	118.6 (7)
C4A—C5A—H5A	120.4	C15B—C16B—H16B	120.7
C5A—C6A—C1A	121.3 (8)	C11B—C16B—H16B	120.7
C5A—C6A—H6A	119.4

C11—B1—C1—C6	−178.9 (8)	C1A—B1A—C11A—C12A	2.1 (9)
Br1—B1—C1—C6	1.4 (14)	Br1A—B1A—C11A—C12A	−178.0 (6)
C11—B1—C1—C2	0.7 (8)	C16A—C11A—C12A—C13A	0.4 (12)
Br1—B1—C1—C2	−179.0 (6)	B1A—C11A—C12A—C13A	178.6 (8)
C6—C1—C2—C3	−1.4 (12)	C16A—C11A—C12A—C2A	−179.7 (8)
B1—C1—C2—C3	178.9 (8)	B1A—C11A—C12A—C2A	−1.4 (9)
C6—C1—C2—C12	179.4 (7)	C3A—C2A—C12A—C13A	−0.6 (14)
B1—C1—C2—C12	−0.3 (9)	C1A—C2A—C12A—C13A	−179.9 (8)
C1—C2—C3—C4	1.1 (12)	C3A—C2A—C12A—C11A	179.5 (8)
C12—C2—C3—C4	−179.9 (8)	C1A—C2A—C12A—C11A	0.2 (9)
C2—C3—C4—C5	−0.1 (13)	C11A—C12A—C13A—C14A	1.4 (13)
C3—C4—C5—C6	−0.5 (14)	C2A—C12A—C13A—C14A	−178.6 (8)
C2—C1—C6—C5	0.8 (12)	C12A—C13A—C14A—C15A	−2.5 (13)
B1—C1—C6—C5	−179.6 (8)	C13A—C14A—C15A—C16A	2.0 (13)
C4—C5—C6—C1	0.2 (13)	C12A—C11A—C16A—C15A	−1.0 (13)
C1—B1—C11—C16	179.1 (9)	B1A—C11A—C16A—C15A	−178.6 (9)
Br1—B1—C11—C16	−1.2 (14)	C14A—C15A—C16A—C11A	−0.1 (14)
C1—B1—C11—C12	−0.9 (9)	C11B—B1B—C1B—C6B	177.9 (9)
Br1—B1—C11—C12	178.8 (7)	Br1B—B1B—C1B—C6B	−2.7 (14)
C16—C11—C12—C13	−2.3 (13)	C11B—B1B—C1B—C2B	−1.7 (9)
B1—C11—C12—C13	177.6 (7)	Br1B—B1B—C1B—C2B	177.6 (6)
C16—C11—C12—C2	−179.2 (7)	C6B—C1B—C2B—C3B	1.8 (11)
B1—C11—C12—C2	0.8 (9)	B1B—C1B—C2B—C3B	−178.5 (8)
C3—C2—C12—C13	4.1 (14)	C6B—C1B—C2B—C12B	−178.6 (7)
C1—C2—C12—C13	−176.8 (8)	B1B—C1B—C2B—C12B	1.1 (8)
C3—C2—C12—C11	−179.4 (9)	C1B—C2B—C3B—C4B	−2.3 (12)
C1—C2—C12—C11	−0.3 (10)	C12B—C2B—C3B—C4B	178.1 (8)
C11—C12—C13—C14	1.6 (12)	C2B—C3B—C4B—C5B	1.5 (12)
C2—C12—C13—C14	177.8 (8)	C3B—C4B—C5B—C6B	−0.1 (13)
C12—C13—C14—C15	−0.3 (13)	C4B—C5B—C6B—C1B	−0.5 (12)
C13—C14—C15—C16	−0.2 (14)	C2B—C1B—C6B—C5B	−0.3 (11)
C14—C15—C16—C11	−0.5 (13)	B1B—C1B—C6B—C5B	−180.0 (9)
C12—C11—C16—C15	1.8 (13)	C1B—B1B—C11B—C12B	1.7 (9)
B1—C11—C16—C15	−178.2 (8)	Br1B—B1B—C11B—C12B	−177.6 (6)
C11A—B1A—C1A—C6A	178.2 (9)	C1B—B1B—C11B—C16B	−179.9 (9)
Br1A—B1A—C1A—C6A	−1.7 (14)	Br1B—B1B—C11B—C16B	0.8 (14)
C11A—B1A—C1A—C2A	−2.0 (9)	C16B—C11B—C12B—C13B	0.9 (12)
Br1A—B1A—C1A—C2A	178.1 (6)	B1B—C11B—C12B—C13B	179.6 (7)
C6A—C1A—C2A—C3A	1.7 (12)	C16B—C11B—C12B—C2B	−179.7 (7)
B1A—C1A—C2A—C3A	−178.2 (7)	B1B—C11B—C12B—C2B	−1.0 (9)
C6A—C1A—C2A—C12A	−178.9 (7)	C3B—C2B—C12B—C13B	−1.2 (14)
B1A—C1A—C2A—C12A	1.2 (9)	C1B—C2B—C12B—C13B	179.2 (8)
C1A—C2A—C3A—C4A	−1.9 (12)	C3B—C2B—C12B—C11B	179.6 (8)
C12A—C2A—C3A—C4A	178.9 (8)	C1B—C2B—C12B—C11B	−0.1 (9)
C2A—C3A—C4A—C5A	0.3 (13)	C11B—C12B—C13B—C14B	0.9 (12)
C3A—C4A—C5A—C6A	1.6 (13)	C2B—C12B—C13B—C14B	−178.3 (8)
C4A—C5A—C6A—C1A	−1.8 (13)	C12B—C13B—C14B—C15B	−1.8 (12)
C2A—C1A—C6A—C5A	0.2 (12)	C13B—C14B—C15B—C16B	0.8 (12)
B1A—C1A—C6A—C5A	180.0 (9)	C14B—C15B—C16B—C11B	1.1 (12)
C1A—B1A—C11A—C16A	179.9 (9)	C12B—C11B—C16B—C15B	−1.9 (12)
Br1A—B1A—C11A—C16A	−0.2 (15)	B1B—C11B—C16B—C15B	179.8 (9)

Experimental details

Crystal data
Chemical formula	C₁₂H₈BBr
M_r	242.90
Crystal system, space group	Orthorhombic, Fdd2
Temperature (K)	173
a, b, c (Å)	34.939 (3), 85.482 (4), 3.9672 (2)
V (Å³)	11848.7 (13)
Z	48
Radiation type	Mo Kα
µ (mm⁻¹)	4.11
Crystal size (mm)	0.19 × 0.03 × 0.03

Data collection
Diffractometer	Stoe IPDS II two-circle diffractometer
Absorption correction	Multi-scan (MULABS; Spek, 2009; Blessing, 1995)
T_min, T_max	0.509, 0.887
No. of measured, independent and observed [I > 2σ(I)] reflections	20875, 5204, 3565
R_int	0.080
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.100, 0.86
No. of reflections	5204
No. of parameters	380
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.61
Absolute structure	Flack (1983), 2183 Friedel pairs
Absolute structure parameter	0.320 (19)

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), XP (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

References

Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gross, U. & Kaufmann, D. (1987). Chem. Ber. 120, 991–994. CrossRef CAS Web of Science Google Scholar
Kaufmann, L., Vitze, H., Bolte, M., Lerner, H.-W. & Wagner, M. (2008). Organometallics, 27, 6215–6221. Web of Science CSD CrossRef CAS Google Scholar
Mewes, J., Lerner, H.-W. & Bolte, M. (2009). Acta Cryst. E65, o451. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2001). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany. Google Scholar