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ISSN: 2056-9890

9-Bromo-9-borafluorene

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[Kaufmann, L., Vitze, H., Bolte, M., Lerner, H.-W. & Wagner, M. (2008). Organometallics, 27, 6215-6221.]). The title compound was obtained by treatment of 9,9-dimethyl-9-silafluorene (Mewes et al., 2009[Mewes, J., Lerner, H.-W. & Bolte, M. (2009). Acta Cryst. E65, o451.]) with BBr3 following a modified literature procedure (Gross et al., 1987[Gross, U. & Kaufmann, D. (1987). Chem. Ber. 120, 991-994.]).

[Scheme 1]

Experimental

Crystal data
  • C12H8BBr

  • Mr = 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[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]; Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.509, Tmax = 0.887

  • 20875 measured reflections

  • 5204 independent reflections

  • 3565 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.46 e Å−3

  • Δρmin = −0.61 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2183 Friedel pairs

  • Flack parameter: 0.320 (19)

Data collection: X-AREA (Stoe & Cie, 2001[Stoe & Cie (2001). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

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).

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 °).

Refinement top

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.

Structure description top

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).

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
[Figure 1] 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.
[Figure 2] Fig. 2. Packing diagram with view onto the bc plane. Hydrogen atoms omitted for clarity.
[Figure 3] Fig. 3. The formation of the title compound.
9-Bromo-9-borafluorene top
Crystal data top
C12H8BBrF(000) = 5760
Mr = 242.90Dx = 1.634 Mg m3
Orthorhombic, Fdd2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2dCell parameters from 9350 reflections
a = 34.939 (3) Åθ = 2.4–25.3°
b = 85.482 (4) ŵ = 4.11 mm1
c = 3.9672 (2) ÅT = 173 K
V = 11848.7 (13) Å3Needle, yellow
Z = 480.19 × 0.03 × 0.03 mm
Data collection top
Stoe IPDS II two-circle
diffractometer
5204 independent reflections
Radiation source: fine-focus sealed tube3565 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.080
ω scansθmax = 25.1°, θmin = 2.2°
Absorption correction: multi-scan
(MULABS; Spek, 2009; Blessing, 1995)
h = 4040
Tmin = 0.509, Tmax = 0.887k = 10090
20875 measured reflectionsl = 44
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-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 reflectionsΔρmax = 0.46 e Å3
380 parametersΔρmin = 0.61 e Å3
1 restraintAbsolute structure: Flack (1983), 2183 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.320 (19)
Crystal data top
C12H8BBrV = 11848.7 (13) Å3
Mr = 242.90Z = 48
Orthorhombic, Fdd2Mo Kα radiation
a = 34.939 (3) ŵ = 4.11 mm1
b = 85.482 (4) ÅT = 173 K
c = 3.9672 (2) Å0.19 × 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)
Tmin = 0.509, Tmax = 0.887Rint = 0.080
20875 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.100Δρmax = 0.46 e Å3
S = 0.86Δρmin = 0.61 e Å3
5204 reflectionsAbsolute structure: Flack (1983), 2183 Friedel pairs
380 parametersAbsolute 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
xyzUiso*/Ueq
Br10.57091 (3)0.512885 (9)0.9579 (2)0.0389 (2)
B10.5914 (3)0.49518 (11)0.727 (2)0.032 (2)
C10.5689 (2)0.48119 (9)0.5713 (18)0.0265 (18)
C20.5971 (2)0.47105 (9)0.434 (2)0.0265 (17)
C30.5857 (2)0.45687 (10)0.277 (2)0.033 (2)
H30.60420.44990.18770.039*
C40.5470 (2)0.45348 (10)0.258 (2)0.036 (2)
H40.53890.44400.15350.043*
C50.5196 (2)0.46368 (10)0.390 (2)0.039 (2)
H50.49330.46110.37140.047*
C60.5304 (2)0.47751 (9)0.546 (2)0.034 (2)
H60.51150.48440.63570.041*
C110.6343 (2)0.49174 (9)0.656 (2)0.0298 (18)
C120.6363 (2)0.47732 (8)0.486 (2)0.0286 (18)
C130.6714 (2)0.47142 (10)0.378 (2)0.035 (2)
H130.67270.46180.25790.042*
C140.7045 (2)0.47980 (10)0.449 (2)0.036 (2)
H140.72860.47580.37720.044*
C150.7029 (3)0.49375 (11)0.621 (2)0.043 (2)
H150.72600.49930.66770.052*
C160.6681 (2)0.49993 (10)0.729 (2)0.036 (2)
H160.66720.50950.84950.044*
Br1A0.69438 (3)0.598421 (10)1.03380 (19)0.0392 (2)
B1A0.6694 (3)0.58003 (12)0.884 (2)0.031 (2)
C1A0.6268 (2)0.57608 (9)0.914 (2)0.0327 (19)
C2A0.6208 (2)0.56131 (9)0.758 (2)0.0249 (17)
C3A0.5844 (2)0.55494 (9)0.739 (2)0.033 (2)
H3A0.58040.54520.62860.040*
C4A0.5537 (2)0.56287 (10)0.882 (2)0.038 (2)
H4A0.52870.55850.87000.046*
C5A0.5592 (2)0.57729 (10)1.045 (2)0.038 (2)
H5A0.53820.58251.14730.046*
C6A0.5955 (2)0.58378 (10)1.055 (2)0.034 (2)
H6A0.59910.59371.15910.040*
C11A0.6880 (2)0.56560 (8)0.705 (2)0.0293 (18)
C12A0.6578 (2)0.55499 (9)0.631 (2)0.0257 (19)
C13A0.6650 (2)0.54106 (9)0.464 (2)0.0334 (19)
H13A0.64470.53410.41070.040*
C14A0.7021 (3)0.53746 (10)0.375 (2)0.035 (2)
H14A0.70730.52770.26900.041*
C15A0.7320 (2)0.54767 (9)0.438 (3)0.038 (2)
H15A0.75720.54510.36900.045*
C16A0.7247 (2)0.56172 (10)0.603 (2)0.036 (2)
H16A0.74520.56870.64720.043*
Br1B0.57408 (3)0.680334 (9)0.0716 (3)0.0384 (2)
B1B0.5983 (3)0.66204 (11)0.112 (2)0.030 (2)
C1B0.6416 (2)0.65923 (9)0.1237 (19)0.027 (2)
C2B0.6472 (2)0.64463 (9)0.291 (2)0.0259 (18)
C3B0.6835 (2)0.63877 (11)0.351 (2)0.033 (2)
H3B0.68690.62920.47010.040*
C4B0.7149 (2)0.64705 (11)0.235 (2)0.038 (2)
H4B0.73990.64300.26980.046*
C5B0.7102 (2)0.66116 (10)0.068 (2)0.034 (2)
H5B0.73200.66670.01070.041*
C6B0.6739 (2)0.66719 (9)0.014 (2)0.035 (2)
H6B0.67110.67690.09920.042*
C11B0.5793 (2)0.64763 (9)0.276 (2)0.0284 (18)
C12B0.6090 (2)0.63775 (9)0.3814 (19)0.0258 (19)
C13B0.6010 (2)0.62372 (9)0.542 (2)0.0292 (18)
H13B0.62120.61710.61620.035*
C14B0.5630 (2)0.61940 (10)0.593 (2)0.032 (2)
H14B0.55720.60970.69700.039*
C15B0.5334 (2)0.62921 (9)0.493 (2)0.0304 (19)
H15B0.50760.62620.53200.036*
C16B0.5409 (2)0.64345 (10)0.336 (2)0.033 (2)
H16B0.52060.65020.27180.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0557 (5)0.0268 (4)0.0342 (5)0.0070 (4)0.0007 (5)0.0021 (5)
B10.048 (6)0.031 (5)0.017 (5)0.004 (4)0.004 (4)0.007 (4)
C10.030 (4)0.022 (4)0.028 (4)0.000 (3)0.001 (4)0.002 (3)
C20.034 (4)0.021 (4)0.025 (4)0.003 (3)0.002 (4)0.002 (4)
C30.039 (5)0.029 (4)0.031 (5)0.007 (4)0.004 (4)0.004 (4)
C40.043 (5)0.026 (4)0.039 (6)0.001 (4)0.008 (5)0.001 (4)
C50.029 (4)0.038 (5)0.049 (6)0.003 (4)0.006 (4)0.010 (5)
C60.041 (5)0.028 (4)0.033 (5)0.002 (4)0.006 (4)0.007 (4)
C110.042 (5)0.027 (4)0.020 (4)0.004 (3)0.000 (4)0.010 (4)
C120.042 (5)0.020 (4)0.023 (5)0.004 (3)0.002 (4)0.006 (4)
C130.041 (5)0.024 (4)0.039 (6)0.003 (4)0.005 (4)0.016 (4)
C140.029 (5)0.046 (5)0.034 (5)0.003 (4)0.004 (4)0.009 (5)
C150.045 (6)0.045 (6)0.039 (6)0.012 (4)0.012 (4)0.017 (5)
C160.038 (5)0.035 (4)0.037 (5)0.004 (3)0.005 (5)0.001 (5)
Br1A0.0505 (5)0.0286 (4)0.0386 (5)0.0069 (4)0.0025 (4)0.0062 (4)
B1A0.043 (6)0.039 (5)0.012 (5)0.004 (4)0.004 (4)0.004 (4)
C1A0.040 (5)0.023 (4)0.036 (5)0.001 (3)0.003 (4)0.010 (4)
C2A0.026 (4)0.032 (4)0.017 (4)0.002 (3)0.003 (3)0.007 (4)
C3A0.039 (5)0.025 (4)0.034 (5)0.003 (3)0.015 (4)0.006 (4)
C4A0.031 (4)0.041 (5)0.042 (6)0.002 (4)0.007 (4)0.008 (4)
C5A0.040 (5)0.043 (5)0.032 (5)0.012 (4)0.007 (4)0.009 (4)
C6A0.039 (5)0.032 (4)0.029 (5)0.010 (4)0.003 (4)0.004 (4)
C11A0.032 (4)0.022 (4)0.034 (4)0.001 (3)0.003 (4)0.002 (4)
C12A0.029 (4)0.020 (4)0.028 (5)0.003 (3)0.005 (4)0.003 (3)
C13A0.044 (5)0.023 (4)0.033 (5)0.001 (4)0.002 (4)0.002 (4)
C14A0.050 (5)0.027 (4)0.027 (5)0.002 (4)0.003 (4)0.003 (4)
C15A0.044 (5)0.028 (4)0.040 (5)0.015 (4)0.002 (5)0.001 (5)
C16A0.035 (5)0.031 (5)0.043 (6)0.008 (4)0.001 (4)0.002 (4)
Br1B0.0501 (5)0.0283 (4)0.0369 (5)0.0083 (4)0.0004 (4)0.0072 (5)
B1B0.031 (5)0.034 (5)0.026 (6)0.002 (4)0.003 (4)0.000 (4)
C1B0.031 (4)0.029 (4)0.023 (5)0.004 (3)0.004 (3)0.003 (3)
C2B0.036 (4)0.023 (4)0.018 (4)0.005 (3)0.002 (4)0.000 (4)
C3B0.033 (5)0.033 (5)0.033 (5)0.004 (4)0.000 (4)0.001 (4)
C4B0.024 (4)0.059 (6)0.032 (5)0.003 (4)0.003 (4)0.013 (5)
C5B0.032 (5)0.040 (5)0.030 (5)0.007 (4)0.000 (4)0.008 (4)
C6B0.043 (5)0.027 (4)0.035 (5)0.004 (4)0.005 (5)0.011 (4)
C11B0.029 (4)0.034 (4)0.022 (4)0.001 (3)0.003 (4)0.000 (4)
C12B0.031 (4)0.023 (4)0.024 (5)0.001 (3)0.000 (4)0.005 (4)
C13B0.035 (5)0.020 (4)0.033 (5)0.006 (3)0.005 (4)0.000 (4)
C14B0.046 (5)0.023 (4)0.028 (5)0.002 (4)0.004 (4)0.001 (3)
C15B0.030 (4)0.027 (4)0.034 (5)0.012 (4)0.002 (4)0.005 (4)
C16B0.040 (5)0.030 (4)0.029 (5)0.004 (4)0.002 (4)0.002 (4)
Geometric parameters (Å, º) top
Br1—B11.909 (10)C5A—H5A0.9500
B1—C111.554 (12)C6A—H6A0.9500
B1—C11.557 (12)C11A—C16A1.384 (11)
C1—C61.386 (10)C11A—C12A1.421 (10)
C1—C21.422 (11)C12A—C13A1.387 (11)
C2—C31.420 (11)C13A—C14A1.377 (12)
C2—C121.482 (10)C13A—H13A0.9500
C3—C41.387 (11)C14A—C15A1.382 (12)
C3—H30.9500C14A—H14A0.9500
C4—C51.394 (12)C15A—C16A1.392 (12)
C4—H40.9500C15A—H15A0.9500
C5—C61.387 (12)C16A—H16A0.9500
C5—H50.9500Br1B—B1B1.920 (10)
C6—H60.9500B1B—C1B1.534 (12)
C11—C161.402 (11)B1B—C11B1.543 (12)
C11—C121.408 (11)C1B—C6B1.387 (11)
C12—C131.396 (11)C1B—C2B1.428 (11)
C13—C141.388 (12)C2B—C3B1.384 (11)
C13—H130.9500C2B—C12B1.504 (11)
C14—C151.376 (13)C3B—C4B1.383 (12)
C14—H140.9500C3B—H3B0.9500
C15—C161.395 (13)C4B—C5B1.386 (12)
C15—H150.9500C4B—H4B0.9500
C16—H160.9500C5B—C6B1.385 (12)
Br1A—B1A1.892 (10)C5B—H5B0.9500
B1A—C1A1.533 (13)C6B—H6B0.9500
B1A—C11A1.565 (12)C11B—C12B1.402 (10)
C1A—C6A1.392 (11)C11B—C16B1.408 (11)
C1A—C2A1.421 (11)C12B—C13B1.386 (11)
C2A—C3A1.387 (10)C13B—C14B1.396 (11)
C2A—C12A1.488 (11)C13B—H13B0.9500
C3A—C4A1.390 (12)C14B—C15B1.389 (11)
C3A—H3A0.9500C14B—H14B0.9500
C4A—C5A1.404 (13)C15B—C16B1.391 (11)
C4A—H4A0.9500C15B—H15B0.9500
C5A—C6A1.386 (12)C16B—H16B0.9500
C11—B1—C1105.7 (7)C1A—C6A—H6A119.4
C11—B1—Br1126.7 (6)C16A—C11A—C12A118.4 (7)
C1—B1—Br1127.6 (6)C16A—C11A—B1A134.8 (7)
C6—C1—C2120.5 (7)C12A—C11A—B1A106.8 (7)
C6—C1—B1133.8 (7)C13A—C12A—C11A120.7 (7)
C2—C1—B1105.7 (7)C13A—C12A—C2A129.2 (7)
C3—C2—C1119.5 (7)C11A—C12A—C2A110.1 (7)
C3—C2—C12129.0 (7)C14A—C13A—C12A119.0 (8)
C1—C2—C12111.5 (7)C14A—C13A—H13A120.5
C4—C3—C2118.5 (7)C12A—C13A—H13A120.5
C4—C3—H3120.7C13A—C14A—C15A121.6 (8)
C2—C3—H3120.7C13A—C14A—H14A119.2
C3—C4—C5121.1 (8)C15A—C14A—H14A119.2
C3—C4—H4119.4C14A—C15A—C16A119.4 (8)
C5—C4—H4119.4C14A—C15A—H15A120.3
C6—C5—C4121.1 (8)C16A—C15A—H15A120.3
C6—C5—H5119.5C11A—C16A—C15A120.8 (8)
C4—C5—H5119.5C11A—C16A—H16A119.6
C1—C6—C5119.2 (8)C15A—C16A—H16A119.6
C1—C6—H6120.4C1B—B1B—C11B106.6 (7)
C5—C6—H6120.4C1B—B1B—Br1B125.0 (6)
C16—C11—C12119.7 (7)C11B—B1B—Br1B128.3 (6)
C16—C11—B1132.9 (8)C6B—C1B—C2B117.5 (8)
C12—C11—B1107.4 (7)C6B—C1B—B1B135.7 (8)
C13—C12—C11120.4 (7)C2B—C1B—B1B106.7 (7)
C13—C12—C2129.7 (7)C3B—C2B—C1B121.5 (8)
C11—C12—C2109.8 (7)C3B—C2B—C12B129.2 (7)
C14—C13—C12119.0 (8)C1B—C2B—C12B109.2 (7)
C14—C13—H13120.5C4B—C3B—C2B118.9 (8)
C12—C13—H13120.5C4B—C3B—H3B120.6
C15—C14—C13121.0 (8)C2B—C3B—H3B120.6
C15—C14—H14119.5C3B—C4B—C5B120.7 (8)
C13—C14—H14119.5C3B—C4B—H4B119.6
C14—C15—C16121.0 (8)C5B—C4B—H4B119.6
C14—C15—H15119.5C4B—C5B—C6B120.4 (8)
C16—C15—H15119.5C4B—C5B—H5B119.8
C15—C16—C11118.9 (8)C6B—C5B—H5B119.8
C15—C16—H16120.5C5B—C6B—C1B120.9 (8)
C11—C16—H16120.5C5B—C6B—H6B119.5
C1A—B1A—C11A105.3 (7)C1B—C6B—H6B119.5
C1A—B1A—Br1A127.3 (6)C12B—C11B—C16B120.0 (7)
C11A—B1A—Br1A127.4 (6)C12B—C11B—B1B106.8 (6)
C6A—C1A—C2A118.6 (7)C16B—C11B—B1B133.2 (7)
C6A—C1A—B1A133.7 (8)C13B—C12B—C11B120.7 (7)
C2A—C1A—B1A107.7 (7)C13B—C12B—C2B128.7 (7)
C3A—C2A—C1A120.5 (7)C11B—C12B—C2B110.6 (7)
C3A—C2A—C12A129.4 (7)C12B—C13B—C14B119.1 (7)
C1A—C2A—C12A110.1 (6)C12B—C13B—H13B120.4
C2A—C3A—C4A119.6 (8)C14B—C13B—H13B120.4
C2A—C3A—H3A120.2C15B—C14B—C13B120.5 (7)
C4A—C3A—H3A120.2C15B—C14B—H14B119.8
C3A—C4A—C5A120.8 (8)C13B—C14B—H14B119.8
C3A—C4A—H4A119.6C14B—C15B—C16B121.1 (7)
C5A—C4A—H4A119.6C14B—C15B—H15B119.5
C6A—C5A—C4A119.2 (8)C16B—C15B—H15B119.5
C6A—C5A—H5A120.4C15B—C16B—C11B118.6 (7)
C4A—C5A—H5A120.4C15B—C16B—H16B120.7
C5A—C6A—C1A121.3 (8)C11B—C16B—H16B120.7
C5A—C6A—H6A119.4
C11—B1—C1—C6178.9 (8)C1A—B1A—C11A—C12A2.1 (9)
Br1—B1—C1—C61.4 (14)Br1A—B1A—C11A—C12A178.0 (6)
C11—B1—C1—C20.7 (8)C16A—C11A—C12A—C13A0.4 (12)
Br1—B1—C1—C2179.0 (6)B1A—C11A—C12A—C13A178.6 (8)
C6—C1—C2—C31.4 (12)C16A—C11A—C12A—C2A179.7 (8)
B1—C1—C2—C3178.9 (8)B1A—C11A—C12A—C2A1.4 (9)
C6—C1—C2—C12179.4 (7)C3A—C2A—C12A—C13A0.6 (14)
B1—C1—C2—C120.3 (9)C1A—C2A—C12A—C13A179.9 (8)
C1—C2—C3—C41.1 (12)C3A—C2A—C12A—C11A179.5 (8)
C12—C2—C3—C4179.9 (8)C1A—C2A—C12A—C11A0.2 (9)
C2—C3—C4—C50.1 (13)C11A—C12A—C13A—C14A1.4 (13)
C3—C4—C5—C60.5 (14)C2A—C12A—C13A—C14A178.6 (8)
C2—C1—C6—C50.8 (12)C12A—C13A—C14A—C15A2.5 (13)
B1—C1—C6—C5179.6 (8)C13A—C14A—C15A—C16A2.0 (13)
C4—C5—C6—C10.2 (13)C12A—C11A—C16A—C15A1.0 (13)
C1—B1—C11—C16179.1 (9)B1A—C11A—C16A—C15A178.6 (9)
Br1—B1—C11—C161.2 (14)C14A—C15A—C16A—C11A0.1 (14)
C1—B1—C11—C120.9 (9)C11B—B1B—C1B—C6B177.9 (9)
Br1—B1—C11—C12178.8 (7)Br1B—B1B—C1B—C6B2.7 (14)
C16—C11—C12—C132.3 (13)C11B—B1B—C1B—C2B1.7 (9)
B1—C11—C12—C13177.6 (7)Br1B—B1B—C1B—C2B177.6 (6)
C16—C11—C12—C2179.2 (7)C6B—C1B—C2B—C3B1.8 (11)
B1—C11—C12—C20.8 (9)B1B—C1B—C2B—C3B178.5 (8)
C3—C2—C12—C134.1 (14)C6B—C1B—C2B—C12B178.6 (7)
C1—C2—C12—C13176.8 (8)B1B—C1B—C2B—C12B1.1 (8)
C3—C2—C12—C11179.4 (9)C1B—C2B—C3B—C4B2.3 (12)
C1—C2—C12—C110.3 (10)C12B—C2B—C3B—C4B178.1 (8)
C11—C12—C13—C141.6 (12)C2B—C3B—C4B—C5B1.5 (12)
C2—C12—C13—C14177.8 (8)C3B—C4B—C5B—C6B0.1 (13)
C12—C13—C14—C150.3 (13)C4B—C5B—C6B—C1B0.5 (12)
C13—C14—C15—C160.2 (14)C2B—C1B—C6B—C5B0.3 (11)
C14—C15—C16—C110.5 (13)B1B—C1B—C6B—C5B180.0 (9)
C12—C11—C16—C151.8 (13)C1B—B1B—C11B—C12B1.7 (9)
B1—C11—C16—C15178.2 (8)Br1B—B1B—C11B—C12B177.6 (6)
C11A—B1A—C1A—C6A178.2 (9)C1B—B1B—C11B—C16B179.9 (9)
Br1A—B1A—C1A—C6A1.7 (14)Br1B—B1B—C11B—C16B0.8 (14)
C11A—B1A—C1A—C2A2.0 (9)C16B—C11B—C12B—C13B0.9 (12)
Br1A—B1A—C1A—C2A178.1 (6)B1B—C11B—C12B—C13B179.6 (7)
C6A—C1A—C2A—C3A1.7 (12)C16B—C11B—C12B—C2B179.7 (7)
B1A—C1A—C2A—C3A178.2 (7)B1B—C11B—C12B—C2B1.0 (9)
C6A—C1A—C2A—C12A178.9 (7)C3B—C2B—C12B—C13B1.2 (14)
B1A—C1A—C2A—C12A1.2 (9)C1B—C2B—C12B—C13B179.2 (8)
C1A—C2A—C3A—C4A1.9 (12)C3B—C2B—C12B—C11B179.6 (8)
C12A—C2A—C3A—C4A178.9 (8)C1B—C2B—C12B—C11B0.1 (9)
C2A—C3A—C4A—C5A0.3 (13)C11B—C12B—C13B—C14B0.9 (12)
C3A—C4A—C5A—C6A1.6 (13)C2B—C12B—C13B—C14B178.3 (8)
C4A—C5A—C6A—C1A1.8 (13)C12B—C13B—C14B—C15B1.8 (12)
C2A—C1A—C6A—C5A0.2 (12)C13B—C14B—C15B—C16B0.8 (12)
B1A—C1A—C6A—C5A180.0 (9)C14B—C15B—C16B—C11B1.1 (12)
C1A—B1A—C11A—C16A179.9 (9)C12B—C11B—C16B—C15B1.9 (12)
Br1A—B1A—C11A—C16A0.2 (15)B1B—C11B—C16B—C15B179.8 (9)

Experimental details

Crystal data
Chemical formulaC12H8BBr
Mr242.90
Crystal system, space groupOrthorhombic, Fdd2
Temperature (K)173
a, b, c (Å)34.939 (3), 85.482 (4), 3.9672 (2)
V3)11848.7 (13)
Z48
Radiation typeMo Kα
µ (mm1)4.11
Crystal size (mm)0.19 × 0.03 × 0.03
Data collection
DiffractometerStoe IPDS II two-circle
diffractometer
Absorption correctionMulti-scan
(MULABS; Spek, 2009; Blessing, 1995)
Tmin, Tmax0.509, 0.887
No. of measured, independent and
observed [I > 2σ(I)] reflections
20875, 5204, 3565
Rint0.080
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.100, 0.86
No. of reflections5204
No. of parameters380
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.46, 0.61
Absolute structureFlack (1983), 2183 Friedel pairs
Absolute structure parameter0.320 (19)

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

 

References

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

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