Tris(4-bromo­phenyl)aminium hexa­chloridoantimonate (`Magic Blue'): a strong oxidant with low inner-sphere reorganization

Both the radical cation tris­(4-bromo­phenyl)aminium hexa­chloridoantimonate (`Magic Blue'), (C₁₈H₁₂Br₃N)[SbCl₆], (I), and neutral tris­(4-bromo­phenyl)amine, C₁₈H₁₂Br₃N, (II), show extremely similar three-bladed propeller structures with planar N atoms. Key geometric features, such as the C-N bond distances and the angles between the planes of the aryl groups and the central NC₃ plane, are identical within experimental uncertainty in the two structures. This contrasts with the significant structural changes observed on oxidation of more electron-rich triaryl­amines, where resonance contributes to the stabilization of the radical cation, and suggests that, in general, more strongly oxidizing triaryl­aminium cations will have lower inner-sphere reorganization energies than their lower-potential analogues.

Computing details

For both compounds, data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 and SAINT (Bruker, 2007); data reduction: SAINT and XPREP (Bruker, 2007; Sheldrick, 2008b); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: XP in SHELXTL (Sheldrick, 2008b); software used to prepare material for publication: XCIF (Sheldrick, 2008b) and publCIF (Westrip, 2010).

(I) tris(4-bromophenyl)aminium hexachloridoantimonate

Crystal data

(C18H12Br3N)[SbCl6]	Dx = 2.259 Mg m^−3
Mr = 816.47	Melting point: 142 K
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2n2ab	Cell parameters from 2305 reflections
a = 17.4052 (7) Å	θ = 8.1–48.2°
b = 16.4768 (7) Å	µ = 6.82 mm^−1
c = 16.7408 (7) Å	T = 100 K
V = 4801.0 (3) Å^3	Plate, dark blue
Z = 8	0.13 × 0.13 × 0.02 mm
F(000) = 3080

Data collection

Bruker d8 APEXII CCD area-detector diffractometer	4956 independent reflections
Radiation source: fine-focus sealed tube	3422 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.078
Detector resolution: 8.33 pixels mm^-1	θmax = 26.6°, θmin = 1.7°
φ and ω scans	h = −21→19
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	k = −19→20
Tmin = 0.478, Tmax = 0.905	l = −21→20
35891 measured reflections

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.075	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0233P)^2 + 16.244P] where P = (Fo^2 + 2Fc^2)/3
4956 reflections	(Δ/σ)max = 0.001
262 parameters	Δρmax = 0.80 e Å^−3
0 restraints	Δρmin = −1.01 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Br1	0.62040 (3)	1.00266 (3)	0.25091 (3)	0.01835 (13)
Br2	0.35656 (3)	0.73785 (4)	−0.22699 (3)	0.02345 (14)
Br3	0.90465 (3)	0.52184 (3)	−0.01022 (3)	0.01952 (14)
N1	0.6239 (2)	0.7354 (2)	0.0027 (2)	0.0136 (9)
C11	0.6229 (3)	0.7955 (3)	0.0630 (3)	0.0147 (11)
C12	0.6927 (3)	0.8317 (3)	0.0867 (3)	0.0173 (12)
H12	0.7399	0.8145	0.0638	0.021*
C13	0.6914 (3)	0.8928 (3)	0.1441 (3)	0.0177 (12)
H13	0.7377	0.9178	0.1614	0.021*
C14	0.6208 (3)	0.9164 (3)	0.1755 (3)	0.0167 (12)
C15	0.5523 (3)	0.8809 (3)	0.1533 (3)	0.0158 (12)
H15	0.5052	0.8977	0.1767	0.019*
C16	0.5538 (3)	0.8205 (3)	0.0964 (3)	0.0150 (12)
H16	0.5072	0.7957	0.0799	0.018*
C21	0.5649 (3)	0.7341 (3)	−0.0549 (3)	0.0131 (11)
C22	0.5364 (3)	0.8081 (3)	−0.0825 (3)	0.0164 (12)
H22	0.5581	0.8578	−0.0647	0.020*
C23	0.4762 (3)	0.8080 (3)	−0.1361 (3)	0.0181 (12)
H23	0.4559	0.8578	−0.1556	0.022*
C24	0.4455 (3)	0.7348 (3)	−0.1613 (3)	0.0177 (12)
C25	0.4762 (3)	0.6606 (3)	−0.1378 (3)	0.0158 (12)
H25	0.4563	0.6112	−0.1585	0.019*
C26	0.5359 (3)	0.6601 (3)	−0.0842 (3)	0.0168 (12)
H26	0.5575	0.6101	−0.0670	0.020*
C31	0.6846 (3)	0.6787 (3)	0.0004 (3)	0.0142 (11)
C32	0.7123 (3)	0.6525 (3)	−0.0733 (3)	0.0161 (12)
H32	0.6873	0.6687	−0.1212	0.019*
C33	0.7762 (3)	0.6033 (3)	−0.0765 (3)	0.0163 (12)
H33	0.7954	0.5845	−0.1263	0.020*
C34	0.8115 (3)	0.5819 (3)	−0.0059 (3)	0.0167 (12)
C35	0.7824 (3)	0.6029 (3)	0.0686 (3)	0.0170 (12)
H35	0.8059	0.5838	0.1162	0.020*
C36	0.7181 (3)	0.6524 (3)	0.0716 (3)	0.0145 (12)
H36	0.6970	0.6683	0.1216	0.017*
Sb1	0.36682 (2)	0.61836 (2)	0.12001 (2)	0.01525 (10)
Cl1	0.36472 (9)	0.71403 (9)	0.22551 (8)	0.0279 (3)
Cl2	0.36738 (8)	0.53009 (8)	0.00832 (8)	0.0225 (3)
Cl3	0.50192 (8)	0.61034 (9)	0.12681 (9)	0.0257 (3)
Cl4	0.35646 (8)	0.50825 (9)	0.21047 (8)	0.0259 (3)
Cl5	0.23013 (8)	0.62534 (8)	0.11370 (8)	0.0229 (3)
Cl6	0.37386 (7)	0.72812 (8)	0.02831 (8)	0.0174 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0207 (3)	0.0148 (2)	0.0195 (3)	−0.0001 (2)	−0.0005 (2)	−0.0022 (2)
Br2	0.0149 (3)	0.0328 (3)	0.0226 (3)	0.0014 (3)	−0.0040 (2)	−0.0037 (3)
Br3	0.0128 (3)	0.0158 (3)	0.0299 (3)	0.0034 (2)	−0.0008 (2)	−0.0006 (2)
N1	0.012 (2)	0.013 (2)	0.016 (2)	−0.0011 (19)	0.0016 (19)	−0.0014 (19)
C11	0.015 (3)	0.010 (2)	0.019 (3)	0.001 (2)	0.003 (2)	0.001 (2)
C12	0.009 (3)	0.020 (3)	0.023 (3)	0.003 (2)	0.000 (2)	−0.002 (3)
C13	0.016 (3)	0.011 (3)	0.026 (3)	0.004 (2)	−0.005 (2)	0.003 (2)
C14	0.016 (3)	0.017 (3)	0.017 (3)	−0.001 (2)	0.000 (2)	0.003 (2)
C15	0.016 (3)	0.017 (3)	0.014 (3)	0.004 (2)	−0.001 (2)	0.000 (2)
C16	0.008 (3)	0.014 (3)	0.022 (3)	0.001 (2)	−0.004 (2)	0.002 (2)
C21	0.007 (3)	0.018 (3)	0.015 (3)	−0.002 (2)	−0.003 (2)	−0.002 (2)
C22	0.016 (3)	0.013 (3)	0.019 (3)	−0.004 (2)	0.002 (2)	−0.002 (2)
C23	0.015 (3)	0.014 (3)	0.025 (3)	0.006 (2)	0.002 (2)	0.005 (3)
C24	0.012 (3)	0.026 (3)	0.015 (3)	0.005 (2)	0.001 (2)	−0.006 (3)
C25	0.012 (3)	0.015 (3)	0.020 (3)	−0.006 (2)	0.002 (2)	−0.004 (2)
C26	0.016 (3)	0.015 (3)	0.020 (3)	−0.002 (2)	0.001 (2)	0.002 (2)
C31	0.012 (3)	0.008 (2)	0.023 (3)	−0.001 (2)	0.002 (2)	−0.002 (2)
C32	0.016 (3)	0.010 (3)	0.023 (3)	0.001 (2)	−0.003 (2)	−0.002 (2)
C33	0.016 (3)	0.012 (3)	0.021 (3)	0.000 (2)	0.001 (2)	−0.002 (2)
C34	0.016 (3)	0.007 (3)	0.027 (3)	−0.003 (2)	0.001 (3)	−0.001 (2)
C35	0.019 (3)	0.012 (3)	0.021 (3)	−0.004 (2)	−0.003 (2)	0.002 (2)
C36	0.013 (3)	0.015 (3)	0.015 (3)	0.001 (2)	−0.003 (2)	−0.001 (2)
Sb1	0.01276 (18)	0.01335 (18)	0.01963 (19)	−0.00057 (15)	−0.00059 (16)	0.00085 (15)
Cl1	0.0358 (9)	0.0249 (7)	0.0229 (8)	−0.0026 (7)	0.0001 (7)	−0.0063 (6)
Cl2	0.0262 (8)	0.0156 (6)	0.0258 (7)	−0.0024 (6)	0.0018 (6)	−0.0039 (6)
Cl3	0.0136 (7)	0.0283 (8)	0.0353 (9)	0.0008 (6)	−0.0034 (6)	0.0061 (7)
Cl4	0.0253 (8)	0.0227 (7)	0.0297 (8)	−0.0029 (6)	−0.0032 (6)	0.0094 (6)
Cl5	0.0142 (7)	0.0255 (8)	0.0290 (8)	−0.0012 (6)	0.0008 (6)	0.0054 (7)
Cl6	0.0150 (7)	0.0132 (6)	0.0239 (7)	−0.0008 (6)	0.0003 (6)	0.0026 (6)

Geometric parameters (Å, º)

Br1—C14	1.901 (5)	C23—H23	0.9500
Br2—C24	1.899 (5)	C24—C25	1.390 (7)
Br3—C34	1.900 (5)	C25—C26	1.372 (7)
N1—C21	1.409 (6)	C25—H25	0.9500
N1—C31	1.410 (6)	C26—H26	0.9500
N1—C11	1.414 (6)	C31—C32	1.394 (7)
C11—C16	1.389 (7)	C31—C36	1.396 (7)
C11—C12	1.409 (7)	C32—C33	1.377 (7)
C12—C13	1.392 (7)	C32—H32	0.9500
C12—H12	0.9500	C33—C34	1.379 (7)
C13—C14	1.392 (7)	C33—H33	0.9500
C13—H13	0.9500	C34—C35	1.390 (7)
C14—C15	1.379 (7)	C35—C36	1.386 (7)
C15—C16	1.377 (7)	C35—H35	0.9500
C15—H15	0.9500	C36—H36	0.9500
C16—H16	0.9500	Sb1—Cl3	2.3580 (14)
C21—C22	1.395 (7)	Sb1—Cl1	2.3676 (14)
C21—C26	1.408 (7)	Sb1—Cl2	2.3688 (14)
C22—C23	1.380 (7)	Sb1—Cl4	2.3701 (14)
C22—H22	0.9500	Sb1—Cl6	2.3754 (13)
C23—C24	1.386 (7)	Sb1—Cl5	2.3842 (14)
C21—N1—C31	121.1 (4)	C25—C26—C21	119.6 (5)
C21—N1—C11	119.3 (4)	C25—C26—H26	120.2
C31—N1—C11	119.6 (4)	C21—C26—H26	120.2
C16—C11—C12	120.5 (5)	C32—C31—C36	121.0 (5)
C16—C11—N1	120.4 (5)	C32—C31—N1	119.2 (5)
C12—C11—N1	119.1 (5)	C36—C31—N1	119.7 (5)
C13—C12—C11	119.1 (5)	C33—C32—C31	119.8 (5)
C13—C12—H12	120.4	C33—C32—H32	120.1
C11—C12—H12	120.4	C31—C32—H32	120.1
C12—C13—C14	118.5 (5)	C32—C33—C34	118.5 (5)
C12—C13—H13	120.8	C32—C33—H33	120.7
C14—C13—H13	120.8	C34—C33—H33	120.7
C15—C14—C13	122.9 (5)	C33—C34—C35	122.9 (5)
C15—C14—Br1	119.5 (4)	C33—C34—Br3	118.8 (4)
C13—C14—Br1	117.6 (4)	C35—C34—Br3	118.4 (4)
C16—C15—C14	118.5 (5)	C36—C35—C34	118.3 (5)
C16—C15—H15	120.8	C36—C35—H35	120.8
C14—C15—H15	120.8	C34—C35—H35	120.8
C15—C16—C11	120.6 (5)	C35—C36—C31	119.3 (5)
C15—C16—H16	119.7	C35—C36—H36	120.4
C11—C16—H16	119.7	C31—C36—H36	120.4
C22—C21—C26	120.9 (5)	Cl3—Sb1—Cl1	90.96 (5)
C22—C21—N1	118.2 (5)	Cl3—Sb1—Cl2	89.97 (5)
C26—C21—N1	120.9 (5)	Cl1—Sb1—Cl2	176.07 (5)
C23—C22—C21	119.0 (5)	Cl3—Sb1—Cl4	90.12 (5)
C23—C22—H22	120.5	Cl1—Sb1—Cl4	91.83 (5)
C21—C22—H22	120.5	Cl2—Sb1—Cl4	91.99 (5)
C22—C23—C24	119.4 (5)	Cl3—Sb1—Cl6	91.29 (5)
C22—C23—H23	120.3	Cl1—Sb1—Cl6	88.62 (5)
C24—C23—H23	120.3	Cl2—Sb1—Cl6	87.54 (5)
C23—C24—C25	122.1 (5)	Cl4—Sb1—Cl6	178.52 (5)
C23—C24—Br2	117.9 (4)	Cl3—Sb1—Cl5	179.50 (5)
C25—C24—Br2	120.0 (4)	Cl1—Sb1—Cl5	89.17 (5)
C26—C25—C24	118.8 (5)	Cl2—Sb1—Cl5	89.93 (5)
C26—C25—H25	120.6	Cl4—Sb1—Cl5	89.39 (5)
C24—C25—H25	120.6	Cl6—Sb1—Cl5	89.20 (5)

(II) 4-bromo-N,N-bis(4-bromophenyl)aniline

Crystal data

C18H12Br3N	F(000) = 928
Mr = 482.02	Dx = 1.960 Mg m^−3
Monoclinic, P21/c	Melting point = 141–143 K
Hall symbol: -P2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.3970 (6) Å	Cell parameters from 2872 reflections
b = 16.0352 (15) Å	θ = 7.2–52.8°
c = 11.3688 (7) Å	µ = 7.40 mm^−1
β = 107.534 (4)°	T = 100 K
V = 1633.5 (2) Å^3	Needle, brown
Z = 4	0.17 × 0.12 × 0.10 mm

Data collection

Bruker d8 APEXII CCD area-detector diffractometer	3379 independent reflections
Radiation source: fine-focus sealed tube	2692 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
Detector resolution: 8.33 pixels mm^-1	θmax = 26.5°, θmin = 2.3°
φ and ω scans	h = −11→9
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	k = −20→19
Tmin = 0.366, Tmax = 0.525	l = −14→14
13565 measured reflections

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.064	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0233P)^2 + 1.6729P] where P = (Fo^2 + 2Fc^2)/3
3379 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 1.02 e Å^−3
0 restraints	Δρmin = −0.57 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Br1	−0.11627 (4)	0.00634 (2)	0.11657 (3)	0.02229 (10)
Br3	0.43055 (4)	0.11736 (3)	1.02807 (3)	0.02652 (11)
Br2	0.99074 (4)	0.26014 (3)	0.37581 (3)	0.02854 (11)
N1	0.4493 (3)	0.12544 (19)	0.4997 (2)	0.0154 (6)
C11	0.3189 (3)	0.0978 (2)	0.4082 (3)	0.0149 (7)
C12	0.2277 (4)	0.0385 (2)	0.4383 (3)	0.0159 (7)
H12	0.2547	0.0162	0.5195	0.019*
C13	0.0981 (4)	0.0115 (2)	0.3518 (3)	0.0181 (8)
H13	0.0351	−0.0281	0.3735	0.022*
C14	0.0620 (3)	0.0432 (2)	0.2332 (3)	0.0160 (7)
C15	0.1517 (3)	0.1012 (2)	0.2009 (3)	0.0144 (7)
H15	0.1263	0.1219	0.1189	0.017*
C16	0.2786 (3)	0.1288 (2)	0.2887 (3)	0.0141 (7)
H16	0.3396	0.1697	0.2671	0.017*
C31	0.4482 (4)	0.1271 (2)	0.6243 (3)	0.0150 (7)
C32	0.5689 (4)	0.0950 (2)	0.7179 (3)	0.0162 (7)
H32	0.6537	0.0739	0.6986	0.019*
C33	0.5649 (4)	0.0939 (2)	0.8377 (3)	0.0190 (8)
H33	0.6475	0.0730	0.9016	0.023*
C34	0.4403 (4)	0.1232 (2)	0.8644 (3)	0.0180 (8)
C35	0.3207 (4)	0.1560 (2)	0.7737 (3)	0.0197 (8)
H35	0.2357	0.1764	0.7934	0.024*
C36	0.3266 (4)	0.1586 (2)	0.6540 (3)	0.0181 (8)
H36	0.2461	0.1825	0.5912	0.022*
C21	0.5765 (3)	0.1551 (2)	0.4704 (3)	0.0142 (7)
C22	0.6151 (4)	0.1242 (2)	0.3699 (3)	0.0160 (7)
H22	0.5561	0.0818	0.3201	0.019*
C23	0.7386 (3)	0.1548 (2)	0.3417 (3)	0.0158 (7)
H23	0.7637	0.1342	0.2722	0.019*
C24	0.8245 (3)	0.2152 (2)	0.4156 (3)	0.0169 (8)
C25	0.7925 (4)	0.2451 (2)	0.5188 (3)	0.0168 (7)
H25	0.8546	0.2857	0.5705	0.020*
C26	0.6684 (4)	0.2146 (2)	0.5450 (3)	0.0162 (7)
H26	0.6450	0.2347	0.6156	0.019*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.01616 (18)	0.0284 (2)	0.01923 (18)	−0.00391 (16)	0.00064 (13)	−0.00418 (16)
Br3	0.0317 (2)	0.0387 (3)	0.01188 (16)	−0.01430 (18)	0.01065 (15)	−0.00500 (16)
Br2	0.01948 (19)	0.0449 (3)	0.0240 (2)	−0.01078 (18)	0.01084 (15)	−0.00133 (18)
N1	0.0129 (14)	0.0255 (18)	0.0078 (12)	−0.0019 (12)	0.0032 (11)	−0.0005 (12)
C11	0.0140 (17)	0.018 (2)	0.0131 (16)	0.0015 (14)	0.0052 (13)	−0.0022 (14)
C12	0.0184 (17)	0.017 (2)	0.0134 (16)	0.0037 (14)	0.0063 (14)	0.0035 (14)
C13	0.0149 (17)	0.021 (2)	0.0188 (17)	−0.0022 (15)	0.0058 (14)	−0.0024 (15)
C14	0.0104 (16)	0.021 (2)	0.0141 (16)	0.0016 (14)	−0.0008 (13)	−0.0049 (14)
C15	0.0149 (17)	0.017 (2)	0.0117 (15)	0.0029 (14)	0.0046 (13)	0.0022 (14)
C16	0.0146 (17)	0.014 (2)	0.0151 (16)	−0.0001 (14)	0.0063 (13)	0.0021 (14)
C31	0.0189 (17)	0.015 (2)	0.0118 (15)	−0.0033 (15)	0.0049 (13)	−0.0028 (14)
C32	0.0125 (17)	0.022 (2)	0.0148 (16)	−0.0005 (14)	0.0045 (13)	−0.0003 (14)
C33	0.0186 (18)	0.023 (2)	0.0127 (16)	−0.0035 (15)	−0.0001 (14)	0.0012 (15)
C34	0.0232 (18)	0.022 (2)	0.0099 (15)	−0.0070 (15)	0.0058 (14)	−0.0013 (14)
C35	0.0204 (18)	0.021 (2)	0.0217 (18)	−0.0012 (15)	0.0118 (15)	−0.0005 (16)
C36	0.0173 (18)	0.021 (2)	0.0165 (16)	0.0019 (15)	0.0059 (14)	0.0009 (15)
C21	0.0123 (16)	0.018 (2)	0.0120 (15)	0.0017 (14)	0.0033 (13)	0.0051 (14)
C22	0.0187 (17)	0.017 (2)	0.0115 (15)	0.0017 (15)	0.0027 (13)	0.0000 (14)
C23	0.0185 (18)	0.021 (2)	0.0086 (15)	0.0051 (15)	0.0046 (13)	0.0031 (14)
C24	0.0104 (16)	0.023 (2)	0.0181 (17)	0.0003 (14)	0.0058 (14)	0.0045 (15)
C25	0.0147 (17)	0.017 (2)	0.0160 (16)	−0.0018 (15)	0.0015 (13)	0.0029 (15)
C26	0.0175 (17)	0.017 (2)	0.0125 (16)	0.0024 (15)	0.0031 (13)	−0.0014 (14)

Geometric parameters (Å, º)

Br1—C14	1.891 (3)	C32—C33	1.373 (4)
Br3—C34	1.893 (3)	C32—H32	0.9500
Br2—C24	1.895 (3)	C33—C34	1.378 (5)
N1—C21	1.416 (4)	C33—H33	0.9500
N1—C11	1.419 (4)	C34—C35	1.380 (5)
N1—C31	1.420 (4)	C35—C36	1.379 (4)
C11—C16	1.388 (4)	C35—H35	0.9500
C11—C12	1.390 (5)	C36—H36	0.9500
C12—C13	1.384 (5)	C21—C22	1.390 (4)
C12—H12	0.9500	C21—C26	1.391 (5)
C13—C14	1.384 (5)	C22—C23	1.383 (4)
C13—H13	0.9500	C22—H22	0.9500
C14—C15	1.378 (5)	C23—C24	1.374 (5)
C15—C16	1.377 (4)	C23—H23	0.9500
C15—H15	0.9500	C24—C25	1.382 (5)
C16—H16	0.9500	C25—C26	1.377 (5)
C31—C36	1.381 (4)	C25—H25	0.9500
C31—C32	1.399 (4)	C26—H26	0.9500
C21—N1—C11	122.4 (3)	C34—C33—H33	120.2
C21—N1—C31	119.3 (3)	C33—C34—C35	121.4 (3)
C11—N1—C31	118.2 (3)	C33—C34—Br3	119.7 (2)
C16—C11—C12	118.7 (3)	C35—C34—Br3	118.9 (2)
C16—C11—N1	121.8 (3)	C36—C35—C34	118.9 (3)
C12—C11—N1	119.6 (3)	C36—C35—H35	120.6
C13—C12—C11	121.0 (3)	C34—C35—H35	120.6
C13—C12—H12	119.5	C35—C36—C31	120.8 (3)
C11—C12—H12	119.5	C35—C36—H36	119.6
C14—C13—C12	118.8 (3)	C31—C36—H36	119.6
C14—C13—H13	120.6	C22—C21—C26	118.5 (3)
C12—C13—H13	120.6	C22—C21—N1	121.5 (3)
C15—C14—C13	121.2 (3)	C26—C21—N1	120.0 (3)
C15—C14—Br1	120.5 (2)	C23—C22—C21	120.7 (3)
C13—C14—Br1	118.3 (3)	C23—C22—H22	119.7
C16—C15—C14	119.3 (3)	C21—C22—H22	119.7
C16—C15—H15	120.3	C24—C23—C22	119.2 (3)
C14—C15—H15	120.3	C24—C23—H23	120.4
C15—C16—C11	121.0 (3)	C22—C23—H23	120.4
C15—C16—H16	119.5	C23—C24—C25	121.7 (3)
C11—C16—H16	119.5	C23—C24—Br2	119.8 (2)
C36—C31—C32	119.3 (3)	C25—C24—Br2	118.5 (3)
C36—C31—N1	120.4 (3)	C26—C25—C24	118.4 (3)
C32—C31—N1	120.3 (3)	C26—C25—H25	120.8
C33—C32—C31	120.1 (3)	C24—C25—H25	120.8
C33—C32—H32	120.0	C25—C26—C21	121.5 (3)
C31—C32—H32	120.0	C25—C26—H26	119.3
C32—C33—C34	119.5 (3)	C21—C26—H26	119.3
C32—C33—H33	120.2