10,10′-Di­bromo-9,9′-bianthryl

In the title compound, C₂₈H₁₆Br₂, the two anthryl moieties are almost perpendicular to each other; the dihedral angles between the anthryl planes are 89.42 (9) and 82.36 (7)° in the two independent molecules, one of which lies on a crystallographic twofold rotation axis. An interesting feature of the crystal structure is the presence of C—H...π interactions.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.012 Å
• R factor = 0.064
• wR factor = 0.175
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full too Low ..............      24.98 Deg.
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.49

Alert level C
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....        C17
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         12
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C28 H16 Br2
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C28 H16 Br2

   2 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: WinGX (Farrugia, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (Version 6a; McArdle, 1995); software used to prepare material for publication: SHELXL97.

10,10'-Dibromo-9,9'-bianthryl

Crystal data

C28H16Br2	F(000) = 3048
Mr = 512.23	Dx = 1.669 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 24.818 (6) Å	θ = 9.4–10.5°
b = 20.677 (4) Å	µ = 3.99 mm^−1
c = 14.473 (5) Å	T = 298 K
β = 124.59 (2)°	Rectangular blocks, brown
V = 6114 (3) Å^3	0.58 × 0.46 × 0.40 mm
Z = 12

Data collection

Enraf-Nonius MACH3 four-circle diffractometer	3109 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
Graphite monochromator	θmax = 25.0°, θmin = 1.4°
ω scans	h = 0→29
Absorption correction: ψ scan (North et al., 1968)	k = 0→24
Tmin = 0.127, Tmax = 0.203	l = −17→14
5669 measured reflections	3 standard reflections every 90 min
5380 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.175	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0738P)^2 + 27.1434P] where P = (Fo^2 + 2Fc^2)/3
5380 reflections	(Δ/σ)max = 0.001
406 parameters	Δρmax = 0.60 e Å^−3
0 restraints	Δρmin = −0.74 e Å^−3

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 (Ų)

	x	y	z	Uiso*/Ueq
Br3	0.00782 (6)	0.37956 (6)	0.88265 (8)	0.0981 (4)
Br2	−0.48257 (5)	0.36138 (5)	0.63677 (9)	0.1005 (4)
Br1	−0.12950 (4)	0.75366 (4)	1.01323 (10)	0.0964 (4)
C1	−0.1958 (4)	0.6835 (4)	1.1182 (7)	0.071 (2)
H1	−0.1660	0.7173	1.1517	0.085*
C2	−0.2200 (4)	0.6580 (4)	1.1721 (7)	0.072 (2)
H2	−0.2068	0.6744	1.2418	0.086*
C3	−0.2647 (4)	0.6076 (4)	1.1254 (6)	0.064 (2)
H3	−0.2807	0.5902	1.1646	0.077*
C4	−0.2854 (3)	0.5831 (3)	1.0232 (6)	0.0492 (17)
H4	−0.3156	0.5496	0.9927	0.059*
C5	−0.2609 (3)	0.6087 (3)	0.9626 (6)	0.0421 (16)
C6	−0.2826 (3)	0.5850 (3)	0.8550 (5)	0.0385 (15)
C7	−0.2587 (3)	0.6097 (3)	0.7956 (6)	0.0456 (17)
C8	−0.2791 (4)	0.5866 (4)	0.6887 (7)	0.0572 (19)
H8	−0.3106	0.5543	0.6558	0.069*
C9	−0.2550 (4)	0.6094 (4)	0.6324 (7)	0.067 (2)
H9	−0.2700	0.5936	0.5615	0.080*
C10	−0.2060 (5)	0.6579 (5)	0.6835 (10)	0.083 (3)
H10	−0.1880	0.6729	0.6461	0.099*
C11	−0.1849 (4)	0.6827 (4)	0.7838 (9)	0.073 (3)
H11	−0.1533	0.7150	0.8139	0.088*
C12	−0.2100 (3)	0.6606 (3)	0.8459 (7)	0.056 (2)
C13	−0.1906 (3)	0.6851 (3)	0.9515 (7)	0.061 (2)
C14	−0.2142 (3)	0.6605 (3)	1.0108 (6)	0.0525 (19)
C15	−0.4206 (3)	0.6098 (4)	0.7140 (6)	0.0560 (19)
H15	−0.3906	0.6434	0.7483	0.067*
C16	−0.4854 (4)	0.6243 (4)	0.6445 (7)	0.070 (2)
H16	−0.4995	0.6671	0.6313	0.084*
C17	−0.5308 (4)	0.5731 (6)	0.5932 (8)	0.090 (3)
H17	−0.5751	0.5827	0.5451	0.108*
C18	−0.5119 (4)	0.5111 (5)	0.6116 (7)	0.074 (2)
H18	−0.5435	0.4789	0.5769	0.089*
C19	−0.4450 (3)	0.4934 (4)	0.6825 (6)	0.0552 (19)
C20	−0.4207 (4)	0.4294 (4)	0.7071 (6)	0.058 (2)
C21	−0.3555 (4)	0.4145 (3)	0.7755 (6)	0.0496 (18)
C22	−0.3287 (5)	0.3505 (3)	0.8040 (7)	0.066 (2)
H22	−0.3576	0.3158	0.7738	0.079*
C23	−0.2642 (5)	0.3374 (4)	0.8720 (7)	0.067 (2)
H23	−0.2492	0.2949	0.8882	0.080*
C24	−0.2203 (4)	0.3896 (3)	0.9176 (7)	0.0595 (19)
H24	−0.1756	0.3815	0.9636	0.071*
C25	−0.2417 (3)	0.4513 (3)	0.8961 (5)	0.0462 (17)
H25	−0.2114	0.4848	0.9279	0.055*
C26	−0.3093 (3)	0.4665 (3)	0.8265 (5)	0.0399 (15)
C27	−0.3316 (3)	0.5313 (3)	0.8042 (5)	0.0407 (15)
C28	−0.3975 (3)	0.5456 (3)	0.7357 (5)	0.0454 (16)
C29	−0.0735 (4)	0.2836 (5)	0.9297 (6)	0.073 (3)
H29	−0.0731	0.2831	0.8658	0.088*
C30	−0.1123 (4)	0.2407 (4)	0.9369 (7)	0.075 (3)
H30	−0.1378	0.2118	0.8785	0.090*
C31	−0.1143 (3)	0.2396 (3)	1.0282 (7)	0.058 (2)
H31	−0.1415	0.2102	1.0315	0.069*
C32	−0.0770 (3)	0.2810 (3)	1.1157 (6)	0.0489 (17)
H32	−0.0786	0.2790	1.1783	0.059*
C33	−0.0355 (3)	0.3276 (3)	1.1124 (5)	0.0408 (15)
C34	0.0023 (3)	0.3712 (3)	1.2011 (5)	0.0429 (16)
C35	0.0423 (3)	0.4160 (3)	1.1949 (6)	0.0432 (16)
C36	0.0818 (3)	0.4605 (3)	1.2833 (6)	0.0509 (18)
H36	0.0807	0.4595	1.3464	0.061*
C37	0.1211 (3)	0.5045 (4)	1.2794 (7)	0.065 (2)
H37	0.1463	0.5331	1.3385	0.078*
C38	0.1230 (4)	0.5059 (5)	1.1846 (9)	0.079 (3)
H38	0.1502	0.5356	1.1817	0.095*
C39	0.0868 (4)	0.4658 (4)	1.0980 (8)	0.073 (3)
H39	0.0888	0.4686	1.0360	0.087*
C40	0.0450 (3)	0.4190 (3)	1.0992 (6)	0.0510 (18)
C41	0.0066 (4)	0.3760 (4)	1.0123 (6)	0.060 (2)
C42	−0.0333 (3)	0.3294 (4)	1.0154 (5)	0.0512 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br3	0.1237 (9)	0.1322 (9)	0.0675 (6)	0.0577 (7)	0.0717 (6)	0.0370 (6)
Br2	0.0997 (8)	0.1055 (8)	0.0842 (7)	−0.0679 (6)	0.0449 (6)	−0.0301 (6)
Br1	0.0593 (5)	0.0446 (5)	0.1468 (10)	−0.0159 (4)	0.0355 (6)	−0.0002 (5)
C1	0.061 (5)	0.053 (5)	0.065 (6)	−0.006 (4)	0.016 (5)	−0.017 (4)
C2	0.068 (6)	0.074 (6)	0.059 (5)	0.000 (5)	0.028 (5)	−0.027 (5)
C3	0.063 (5)	0.074 (6)	0.054 (5)	0.006 (4)	0.033 (4)	−0.009 (4)
C4	0.048 (4)	0.043 (4)	0.053 (4)	−0.001 (3)	0.026 (4)	−0.008 (3)
C5	0.040 (4)	0.027 (3)	0.051 (4)	0.001 (3)	0.021 (3)	−0.005 (3)
C6	0.037 (3)	0.030 (3)	0.049 (4)	0.010 (3)	0.024 (3)	0.013 (3)
C7	0.045 (4)	0.029 (3)	0.061 (5)	0.008 (3)	0.029 (4)	0.014 (3)
C8	0.063 (5)	0.050 (4)	0.068 (5)	0.000 (4)	0.043 (4)	0.010 (4)
C9	0.081 (6)	0.061 (5)	0.082 (6)	0.016 (5)	0.061 (5)	0.014 (5)
C10	0.082 (7)	0.069 (6)	0.133 (9)	0.026 (5)	0.082 (7)	0.049 (6)
C11	0.070 (6)	0.045 (5)	0.120 (8)	0.005 (4)	0.064 (6)	0.028 (5)
C12	0.046 (4)	0.027 (4)	0.093 (6)	0.009 (3)	0.039 (4)	0.025 (4)
C13	0.045 (4)	0.030 (4)	0.082 (6)	0.002 (3)	0.021 (4)	0.003 (4)
C14	0.043 (4)	0.032 (4)	0.065 (5)	0.003 (3)	0.020 (4)	0.005 (4)
C15	0.039 (4)	0.071 (5)	0.058 (5)	0.008 (4)	0.027 (4)	0.016 (4)
C16	0.052 (5)	0.092 (6)	0.075 (6)	0.021 (5)	0.040 (5)	0.038 (5)
C17	0.031 (4)	0.151 (10)	0.075 (6)	0.020 (6)	0.023 (5)	0.038 (7)
C18	0.045 (5)	0.113 (8)	0.056 (5)	−0.019 (5)	0.024 (4)	−0.007 (5)
C19	0.046 (4)	0.082 (6)	0.041 (4)	−0.012 (4)	0.026 (4)	0.000 (4)
C20	0.060 (5)	0.069 (5)	0.052 (5)	−0.028 (4)	0.036 (4)	−0.013 (4)
C21	0.063 (5)	0.046 (4)	0.054 (4)	−0.022 (4)	0.042 (4)	−0.016 (3)
C22	0.106 (7)	0.032 (4)	0.082 (6)	−0.020 (4)	0.067 (6)	−0.010 (4)
C23	0.092 (7)	0.032 (4)	0.086 (6)	0.000 (4)	0.056 (6)	−0.004 (4)
C24	0.072 (5)	0.043 (4)	0.069 (5)	0.004 (4)	0.043 (4)	0.004 (4)
C25	0.051 (4)	0.037 (4)	0.050 (4)	−0.003 (3)	0.029 (4)	−0.007 (3)
C26	0.054 (4)	0.033 (4)	0.045 (4)	−0.010 (3)	0.035 (3)	−0.001 (3)
C27	0.049 (4)	0.040 (4)	0.038 (4)	−0.011 (3)	0.027 (3)	−0.005 (3)
C28	0.044 (4)	0.052 (4)	0.042 (4)	−0.002 (3)	0.025 (3)	−0.002 (3)
C29	0.083 (6)	0.080 (6)	0.040 (5)	0.038 (5)	0.025 (5)	0.004 (4)
C30	0.075 (6)	0.063 (6)	0.047 (5)	0.021 (5)	0.012 (5)	−0.018 (4)
C31	0.051 (5)	0.038 (4)	0.061 (5)	−0.003 (3)	0.018 (4)	−0.011 (4)
C32	0.054 (4)	0.040 (4)	0.046 (4)	0.015 (3)	0.024 (4)	0.004 (3)
C33	0.043 (4)	0.036 (4)	0.038 (4)	0.014 (3)	0.020 (3)	0.004 (3)
C34	0.041 (4)	0.037 (4)	0.040 (4)	0.014 (3)	0.017 (3)	0.009 (3)
C35	0.044 (4)	0.039 (4)	0.049 (4)	0.012 (3)	0.028 (3)	0.012 (3)
C36	0.050 (4)	0.048 (4)	0.058 (5)	0.004 (3)	0.033 (4)	0.006 (4)
C37	0.052 (5)	0.051 (5)	0.084 (6)	−0.008 (4)	0.034 (5)	0.003 (4)
C38	0.063 (6)	0.078 (6)	0.101 (8)	0.001 (5)	0.049 (6)	0.035 (6)
C39	0.063 (5)	0.090 (7)	0.080 (6)	0.023 (5)	0.049 (5)	0.041 (6)
C40	0.054 (4)	0.050 (4)	0.055 (5)	0.019 (4)	0.035 (4)	0.018 (4)
C41	0.069 (5)	0.071 (5)	0.053 (5)	0.042 (4)	0.042 (4)	0.024 (4)
C42	0.055 (4)	0.054 (4)	0.034 (4)	0.029 (4)	0.019 (4)	0.009 (4)

Geometric parameters (Å, º)

Br3—C41	1.895 (7)	C19—C28	1.456 (9)
Br3—C40	2.838 (8)	C20—C21	1.369 (10)
Br2—C20	1.896 (7)	C21—C22	1.433 (10)
Br1—C13	1.889 (7)	C21—C26	1.435 (8)
C1—C2	1.332 (11)	C22—C23	1.348 (11)
C1—C14	1.431 (11)	C22—H22	0.9300
C1—H1	0.9300	C23—C24	1.404 (11)
C2—C3	1.387 (11)	C23—H23	0.9300
C2—H2	0.9300	C24—C25	1.350 (9)
C3—C4	1.358 (10)	C24—H24	0.9300
C3—H3	0.9300	C25—C26	1.417 (9)
C4—C5	1.423 (9)	C25—H25	0.9300
C4—H4	0.9300	C26—C27	1.416 (9)
C5—C6	1.415 (9)	C27—C28	1.379 (9)
C5—C14	1.435 (9)	C29—C30	1.357 (12)
C6—C7	1.391 (9)	C29—C42	1.423 (11)
C6—C27	1.496 (8)	C29—H29	0.9300
C7—C8	1.410 (10)	C30—C31	1.350 (11)
C7—C12	1.448 (9)	C30—H30	0.9300
C8—C9	1.340 (10)	C31—C32	1.365 (9)
C8—H8	0.9300	C31—H31	0.9300
C9—C10	1.418 (13)	C32—C33	1.430 (9)
C9—H9	0.9300	C32—H32	0.9300
C10—C11	1.335 (13)	C33—C34	1.406 (9)
C10—H10	0.9300	C33—C42	1.435 (9)
C11—C12	1.428 (11)	C34—C35	1.395 (9)
C11—H11	0.9300	C34—C34^i	1.484 (13)
C12—C13	1.410 (11)	C35—C36	1.422 (9)
C13—C14	1.381 (11)	C35—C40	1.427 (9)
C15—C16	1.361 (10)	C36—C37	1.359 (9)
C15—C28	1.408 (9)	C36—H36	0.9300
C15—H15	0.9300	C37—C38	1.399 (12)
C16—C17	1.411 (13)	C37—H37	0.9300
C16—H16	0.9300	C38—C39	1.336 (12)
C17—C18	1.338 (13)	C38—H38	0.9300
C17—H17	0.9300	C39—C40	1.426 (11)
C18—C19	1.417 (11)	C39—H39	0.9300
C18—H18	0.9300	C40—C41	1.386 (11)
C19—C20	1.415 (11)	C41—C42	1.401 (11)
C2—C1—C14	122.3 (8)	C23—C22—C21	124.1 (7)
C2—C1—H1	118.9	C23—C22—H22	117.9
C14—C1—H1	118.9	C21—C22—H22	117.9
C1—C2—C3	120.9 (8)	C22—C23—C24	118.1 (7)
C1—C2—H2	119.6	C22—C23—H23	120.9
C3—C2—H2	119.6	C24—C23—H23	120.9
C4—C3—C2	120.9 (8)	C25—C24—C23	121.3 (8)
C4—C3—H3	119.6	C25—C24—H24	119.3
C2—C3—H3	119.6	C23—C24—H24	119.3
C3—C4—C5	120.2 (7)	C24—C25—C26	121.8 (6)
C3—C4—H4	119.9	C24—C25—H25	119.1
C5—C4—H4	119.9	C26—C25—H25	119.1
C6—C5—C4	121.3 (6)	C27—C26—C25	121.6 (6)
C6—C5—C14	119.5 (6)	C27—C26—C21	119.8 (6)
C4—C5—C14	119.2 (6)	C25—C26—C21	118.5 (6)
C7—C6—C5	121.6 (6)	C28—C27—C26	121.2 (6)
C7—C6—C27	118.8 (6)	C28—C27—C6	119.7 (6)
C5—C6—C27	119.6 (5)	C26—C27—C6	119.1 (5)
C6—C7—C8	122.8 (6)	C27—C28—C15	121.9 (6)
C6—C7—C12	118.8 (7)	C27—C28—C19	119.7 (6)
C8—C7—C12	118.4 (6)	C15—C28—C19	118.4 (6)
C9—C8—C7	122.8 (7)	C30—C29—C42	123.0 (8)
C9—C8—H8	118.6	C30—C29—H29	118.5
C7—C8—H8	118.6	C42—C29—H29	118.5
C8—C9—C10	118.5 (8)	C31—C30—C29	120.5 (8)
C8—C9—H9	120.7	C31—C30—H30	119.7
C10—C9—H9	120.7	C29—C30—H30	119.7
C11—C10—C9	122.0 (8)	C30—C31—C32	121.1 (8)
C11—C10—H10	119.0	C30—C31—H31	119.5
C9—C10—H10	119.0	C32—C31—H31	119.5
C10—C11—C12	121.3 (8)	C31—C32—C33	120.8 (7)
C10—C11—H11	119.3	C31—C32—H32	119.6
C12—C11—H11	119.3	C33—C32—H32	119.6
C13—C12—C11	124.3 (8)	C34—C33—C32	121.5 (6)
C13—C12—C7	118.8 (7)	C34—C33—C42	120.0 (6)
C11—C12—C7	116.9 (8)	C32—C33—C42	118.6 (6)
C14—C13—C12	122.5 (7)	C35—C34—C33	119.9 (6)
C14—C13—Br1	119.4 (6)	C35—C34—C34^i	120.2 (5)
C12—C13—Br1	118.1 (6)	C33—C34—C34^i	119.9 (6)
C13—C14—C1	124.6 (7)	C34—C35—C36	121.7 (6)
C13—C14—C5	118.8 (7)	C34—C35—C40	121.2 (6)
C1—C14—C5	116.5 (7)	C36—C35—C40	117.1 (6)
C16—C15—C28	122.3 (8)	C37—C36—C35	122.8 (7)
C16—C15—H15	118.9	C37—C36—H36	118.6
C28—C15—H15	118.9	C35—C36—H36	118.6
C15—C16—C17	118.6 (8)	C36—C37—C38	118.7 (8)
C15—C16—H16	120.7	C36—C37—H37	120.7
C17—C16—H16	120.7	C38—C37—H37	120.7
C18—C17—C16	121.9 (8)	C39—C38—C37	121.8 (8)
C18—C17—H17	119.0	C39—C38—H38	119.1
C16—C17—H17	119.0	C37—C38—H38	119.1
C17—C18—C19	121.7 (8)	C38—C39—C40	121.1 (8)
C17—C18—H18	119.2	C38—C39—H39	119.4
C19—C18—H18	119.2	C40—C39—H39	119.4
C20—C19—C18	125.5 (7)	C41—C40—C39	123.8 (7)
C20—C19—C28	117.4 (6)	C41—C40—C35	117.8 (7)
C18—C19—C28	117.1 (7)	C39—C40—C35	118.5 (7)
C21—C20—C19	123.5 (6)	C40—C41—C42	123.1 (7)
C21—C20—Br2	119.0 (6)	C40—C41—Br3	118.9 (6)
C19—C20—Br2	117.4 (6)	C42—C41—Br3	117.9 (6)
C20—C21—C22	125.5 (7)	C41—C42—C29	125.9 (7)
C20—C21—C26	118.3 (7)	C41—C42—C33	118.0 (7)
C22—C21—C26	116.1 (7)	C29—C42—C33	116.0 (8)
C14—C1—C2—C3	0.0 (13)	C22—C21—C26—C27	−179.1 (6)
C1—C2—C3—C4	−0.6 (12)	C20—C21—C26—C25	−179.2 (6)
C2—C3—C4—C5	0.6 (11)	C22—C21—C26—C25	2.5 (9)
C3—C4—C5—C6	−178.7 (6)	C25—C26—C27—C28	179.6 (6)
C3—C4—C5—C14	0.0 (9)	C21—C26—C27—C28	1.3 (9)
C4—C5—C6—C7	−179.7 (6)	C25—C26—C27—C6	0.3 (9)
C14—C5—C6—C7	1.6 (9)	C21—C26—C27—C6	−178.0 (6)
C4—C5—C6—C27	−0.9 (9)	C7—C6—C27—C28	−89.0 (7)
C14—C5—C6—C27	−179.6 (5)	C5—C6—C27—C28	92.2 (7)
C5—C6—C7—C8	179.4 (6)	C7—C6—C27—C26	90.3 (7)
C27—C6—C7—C8	0.6 (9)	C5—C6—C27—C26	−88.5 (7)
C5—C6—C7—C12	0.3 (9)	C26—C27—C28—C15	179.0 (6)
C27—C6—C7—C12	−178.5 (5)	C6—C27—C28—C15	−1.7 (10)
C6—C7—C8—C9	−178.5 (7)	C26—C27—C28—C19	−1.9 (9)
C12—C7—C8—C9	0.6 (10)	C6—C27—C28—C19	177.5 (6)
C7—C8—C9—C10	1.1 (11)	C16—C15—C28—C27	178.5 (7)
C8—C9—C10—C11	−2.1 (12)	C16—C15—C28—C19	−0.6 (10)
C9—C10—C11—C12	1.1 (13)	C20—C19—C28—C27	1.9 (9)
C10—C11—C12—C13	−179.3 (8)	C18—C19—C28—C27	−178.9 (6)
C10—C11—C12—C7	0.7 (11)	C20—C19—C28—C15	−178.9 (6)
C6—C7—C12—C13	−2.4 (9)	C18—C19—C28—C15	0.2 (9)
C8—C7—C12—C13	178.4 (6)	C42—C29—C30—C31	−0.2 (12)
C6—C7—C12—C11	177.6 (6)	C29—C30—C31—C32	−0.6 (12)
C8—C7—C12—C11	−1.5 (9)	C30—C31—C32—C33	1.0 (10)
C11—C12—C13—C14	−177.4 (7)	C31—C32—C33—C34	178.9 (6)
C7—C12—C13—C14	2.7 (10)	C31—C32—C33—C42	−0.7 (9)
C11—C12—C13—Br1	2.3 (9)	C32—C33—C34—C35	−180.0 (5)
C7—C12—C13—Br1	−177.6 (4)	C42—C33—C34—C35	−0.4 (9)
C12—C13—C14—C1	179.7 (7)	C32—C33—C34—C34^i	−2.4 (9)
Br1—C13—C14—C1	0.1 (10)	C42—C33—C34—C34^i	177.2 (6)
C12—C13—C14—C5	−0.7 (10)	C33—C34—C35—C36	−179.3 (6)
Br1—C13—C14—C5	179.6 (5)	C34^i—C34—C35—C36	3.0 (9)
C2—C1—C14—C13	−179.9 (8)	C33—C34—C35—C40	0.8 (9)
C2—C1—C14—C5	0.6 (11)	C34^i—C34—C35—C40	−176.9 (6)
C6—C5—C14—C13	−1.4 (9)	C34—C35—C36—C37	179.9 (6)
C4—C5—C14—C13	179.9 (6)	C40—C35—C36—C37	−0.2 (10)
C6—C5—C14—C1	178.1 (6)	C35—C36—C37—C38	−0.2 (11)
C4—C5—C14—C1	−0.5 (9)	C36—C37—C38—C39	0.7 (12)
C28—C15—C16—C17	0.2 (11)	C37—C38—C39—C40	−0.9 (13)
C15—C16—C17—C18	0.6 (13)	C38—C39—C40—C41	−179.7 (7)
C16—C17—C18—C19	−1.0 (14)	C38—C39—C40—C35	0.5 (11)
C17—C18—C19—C20	179.7 (8)	C34—C35—C40—C41	0.1 (9)
C17—C18—C19—C28	0.6 (11)	C36—C35—C40—C41	−179.8 (6)
C18—C19—C20—C21	179.4 (7)	C34—C35—C40—C39	180.0 (6)
C28—C19—C20—C21	−1.5 (10)	C36—C35—C40—C39	0.1 (9)
C18—C19—C20—Br2	1.5 (10)	C39—C40—C41—C42	178.8 (6)
C28—C19—C20—Br2	−179.4 (5)	C35—C40—C41—C42	−1.4 (10)
C19—C20—C21—C22	179.1 (7)	C39—C40—C41—Br3	−0.9 (9)
Br2—C20—C21—C22	−3.0 (10)	C35—C40—C41—Br3	178.9 (4)
C19—C20—C21—C26	1.0 (10)	C40—C41—C42—C29	−179.5 (7)
Br2—C20—C21—C26	178.9 (5)	Br3—C41—C42—C29	0.2 (9)
C20—C21—C22—C23	−179.8 (8)	C40—C41—C42—C33	1.7 (9)
C26—C21—C22—C23	−1.7 (11)	Br3—C41—C42—C33	−178.6 (4)
C21—C22—C23—C24	−0.2 (12)	C30—C29—C42—C41	−178.3 (7)
C22—C23—C24—C25	1.2 (12)	C30—C29—C42—C33	0.5 (10)
C23—C24—C25—C26	−0.2 (11)	C34—C33—C42—C41	−0.8 (9)
C24—C25—C26—C27	180.0 (6)	C32—C33—C42—C41	178.8 (6)
C24—C25—C26—C21	−1.7 (10)	C34—C33—C42—C29	−179.7 (6)
C20—C21—C26—C27	−0.9 (9)	C32—C33—C42—C29	−0.1 (8)

Symmetry code: (i) −x, y, −z+5/2.