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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o444.
Published online 2010 January 23. doi:  10.1107/S1600536810001625
PMCID: PMC2979814

9-Bromo-9-borafluorene

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 [triangle]). The title compound was obtained by treatment of 9,9-dimethyl-9-silafluorene (Mewes et al., 2009 [triangle]) with BBr3 following a modified literature procedure (Gross et al., 1987 [triangle]).

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Object name is e-66-0o444-scheme1.jpg

Experimental

Crystal data

  • C12H8BBr
  • M r = 242.90
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o444-efi1.jpg
  • 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 [triangle]; Blessing, 1995 [triangle]) 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 [triangle]), 2183 Friedel pairs
  • Flack parameter: 0.320 (19)

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

Supplementary Material

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810001625/fk2010Isup2.hkl

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

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.
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.

Crystal data

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

Stoe IPDS II two-circle diffractometer5204 independent reflections
Radiation source: fine-focus sealed tube3565 reflections with I > 2σ(I)
graphiteRint = 0.080
ω scansθmax = 25.1°, θmin = 2.2°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)h = −40→40
Tmin = 0.509, Tmax = 0.887k = −100→90
20875 measured reflectionsl = −4→4

Refinement

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) = 0.100w = 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 methodsFlack parameter: 0.320 (19)

Special details

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)

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)
H5B0.73200.6667−0.01070.041*
C6B0.6739 (2)0.66719 (9)0.014 (2)0.035 (2)
H6B0.67110.6769−0.09920.042*
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)

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, °)

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—C6−178.9 (8)C1A—B1A—C11A—C12A2.1 (9)
Br1—B1—C1—C61.4 (14)Br1A—B1A—C11A—C12A−178.0 (6)
C11—B1—C1—C20.7 (8)C16A—C11A—C12A—C13A0.4 (12)
Br1—B1—C1—C2−179.0 (6)B1A—C11A—C12A—C13A178.6 (8)
C6—C1—C2—C3−1.4 (12)C16A—C11A—C12A—C2A−179.7 (8)
B1—C1—C2—C3178.9 (8)B1A—C11A—C12A—C2A−1.4 (9)
C6—C1—C2—C12179.4 (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—C41.1 (12)C3A—C2A—C12A—C11A179.5 (8)
C12—C2—C3—C4−179.9 (8)C1A—C2A—C12A—C11A0.2 (9)
C2—C3—C4—C5−0.1 (13)C11A—C12A—C13A—C14A1.4 (13)
C3—C4—C5—C6−0.5 (14)C2A—C12A—C13A—C14A−178.6 (8)
C2—C1—C6—C50.8 (12)C12A—C13A—C14A—C15A−2.5 (13)
B1—C1—C6—C5−179.6 (8)C13A—C14A—C15A—C16A2.0 (13)
C4—C5—C6—C10.2 (13)C12A—C11A—C16A—C15A−1.0 (13)
C1—B1—C11—C16179.1 (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—C6B177.9 (9)
Br1—B1—C11—C12178.8 (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—C13177.6 (7)Br1B—B1B—C1B—C2B177.6 (6)
C16—C11—C12—C2−179.2 (7)C6B—C1B—C2B—C3B1.8 (11)
B1—C11—C12—C20.8 (9)B1B—C1B—C2B—C3B−178.5 (8)
C3—C2—C12—C134.1 (14)C6B—C1B—C2B—C12B−178.6 (7)
C1—C2—C12—C13−176.8 (8)B1B—C1B—C2B—C12B1.1 (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—C4B178.1 (8)
C11—C12—C13—C141.6 (12)C2B—C3B—C4B—C5B1.5 (12)
C2—C12—C13—C14177.8 (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—C151.8 (13)C1B—B1B—C11B—C12B1.7 (9)
B1—C11—C16—C15−178.2 (8)Br1B—B1B—C11B—C12B−177.6 (6)
C11A—B1A—C1A—C6A178.2 (9)C1B—B1B—C11B—C16B−179.9 (9)
Br1A—B1A—C1A—C6A−1.7 (14)Br1B—B1B—C11B—C16B0.8 (14)
C11A—B1A—C1A—C2A−2.0 (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—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—C12A1.2 (9)C1B—C2B—C12B—C13B179.2 (8)
C1A—C2A—C3A—C4A−1.9 (12)C3B—C2B—C12B—C11B179.6 (8)
C12A—C2A—C3A—C4A178.9 (8)C1B—C2B—C12B—C11B−0.1 (9)
C2A—C3A—C4A—C5A0.3 (13)C11B—C12B—C13B—C14B0.9 (12)
C3A—C4A—C5A—C6A1.6 (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—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—C15B−1.9 (12)
Br1A—B1A—C11A—C16A−0.2 (15)B1B—C11B—C16B—C15B179.8 (9)

Footnotes

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

References

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