9-Bromo-9-borafluorene.

The title compound, C(12)H(8)BBr, crystallizes with three essentially planar mol-ecules (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 mol-ecules. 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 = 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 ▶).

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

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

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

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)

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	0.57091 (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*

	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)

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)