Acta Crystallographica Section E: Structure Reports Online

Acta Crystallogr Sect E Struct Rep Online. 66(Pt 2): o444-o444

9-Bromo-9-borafluorene

Alexander Hübnera, Hans-Wolfram Lernera, Matthias Wagnera, Michael Boltea*

a. Institut 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

© Hübner et al. 2010

DOI: 10.1107/S1600536810001625

Published online: 23 January 2010

Abstract

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,

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[F ² > 2σ(F ²)] = 0.051

wR(F ²) = 0.100

S = 0.86

5204 reflections

380 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.46 e Å⁻³

Δρmin = −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 ▶).

Supplementary Material

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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FK2010).

supplementary crystallographic information

Comment

Polyferrocenylenes with bridging elements ERx (e. g. ERx = 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).

Experimental

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 °).

Refinement

Hydrogen atoms were located in a difference Fourier map but they were included in calculated positions [C—H = 0.95 Å] and refined as riding [Uiso(H) = 1.2Ueq(C)]. The crystal turned out to be a racemic twin with a ratio of of 0.680 (19)/0.320 (19) for the two twin components.

Figures

Fig. 1.View larger versionFig. 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.View larger versionFig. 2. Packing diagram with view onto the bc plane. Hydrogen atoms omitted for clarity.

Fig. 3.View larger versionFig. 3. The formation of the title compound.

Crystal data

See full table

Data collection

See full table

Refinement

See full table

Special details

See full table

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

See full table

Atomic displacement parameters (Å²)

See full table

Geometric parameters (Å, °)

See full table

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References

Blessing, R. H. (1995). Acta Cryst. A51, 33–38.

Flack, H. D. (1983). Acta Cryst. A39, 876–881.

Gross, U. & Kaufmann, D. (1987). Chem. Ber.120, 991–994.

Kaufmann, L., Vitze, H., Bolte, M., Lerner, H.-W. & Wagner, M. (2008). Organometallics, 27, 6215–6221.

Mewes, J., Lerner, H.-W. & Bolte, M. (2009). Acta Cryst. E65, o451.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2009). Acta Cryst. D65, 148–155.

Stoe & Cie (2001). X-AREA and X-RED Stoe & Cie, Darmstadt, Germany.

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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.

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Fig. 2.

Packing diagram with view onto the bc plane. Hydrogen atoms omitted for clarity.

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Fig. 3.

The formation of the title compound.

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C₁₂H₈BBr | F(000) = 5760
Mr = 242.90 | Dx = 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

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

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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(Fo²) + (0.0328P)²] where P = (Fo² + 2Fc²)/3
S = 0.86 | (Δ/σ)max = 0.002
5204 reflections | Δρmax = 0.46 e Å⁻³
380 parameters | Δρmin = −0.61 e Å⁻³
1 restraint | Absolute structure: Flack (1983), 2183 Friedel pairs
Primary atom site location: structure-invariant direct methods | Flack parameter: 0.320 (19)

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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.

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| x | y | z | Uiso*/Ueq |
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* |

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| U ¹¹ | U ²² | U ³³ | U ¹² | U ¹³ | U ²³
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)

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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)

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