Halogen bonding in a series of Br(CF₂)_nBr–DABCO adducts (n = 4, 6, 8)

Halogen bonding (XB) is a highly-directional class of inter­molecular inter­actions that has been used as a powerful tool to drive the design of crystals in the solid phase. To date, the majority of XB donors have been iodine-containing compounds, with many fewer involving brominated analogues. We report the formation of adducts in the vapour phase from a series of di­bromo­perfluoro­alkyl compounds, BrCF₂(CF₂)_nCF₂Br (n = 2, 4, 6), and 1,4-di­aza­bicyclo­[2.2.2]octane (DABCO). Single-crystal X-ray diffraction studies of the colourless crystals identified 1,4-di­aza­bicyclo­[2.2.2]octa­ne–1,4-di­bromo­perfluoro­butane (1/1), C₄Br₂F₈·C₆H₁₂N₂, (I), 1,4-di­aza­bicyclo­[2.2.2]octa­ne–1,6-di­bromo­perfluoro­hex­ane (1/1), C₆Br₂F₁₂·C₆H₁₂N₂, (II), and 1,4-di­aza­bicyclo­[2.2.2]octa­ne–1,8-di­bromo­perfluoro­octane (1/1), C₈Br₂F₁₆·C₆H₁₂N₂, (III), each of which displays a one-dimensional halogen-bonded network. All three adducts exhibit N...Br distances less than the sum of the van der Waals radii, with butane analogue (I) showing the shortest N...Br halogen-bond distances yet reported between a bromo­perfluoro­carbon and a nitro­gen base [2.809 (3) and 2.818 (3) Å], which are 0.58 and 0.59 Å shorter than the sum of the van der Waals radii.

Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2015) for (I); CrysAlis PRO (Agilent, 2014) for (II), (III). Cell refinement: CrysAlis PRO (Rigaku OD, 2015) for (I); CrysAlis PRO (Agilent, 2014) for (II), (III). Data reduction: CrysAlis PRO (Rigaku OD, 2015) for (I); CrysAlis PRO (Agilent, 2014) for (II), (III). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for (I); SHELXT (Sheldrick, 2015a) for (II); SUPERFLIP (Palatinus & Chapuis, 2007; Palatinus & van der Lee, 2008; Palatinus et al., 2012) for (III). Program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b) for (I), (II); SHELXL97 (Sheldrick, 2008) for (III). For all structures, molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

1,4-Dibromoperfluorobutane–1,4-diazabicyclo[2.2.2]octane (1/1) (I)

Crystal data

C4Br2F8·C6H12N2	F(000) = 912
Mr = 472.04	Dx = 2.027 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.4659 (6) Å	Cell parameters from 1842 reflections
b = 11.0854 (6) Å	θ = 3.7–27.3°
c = 10.7955 (6) Å	µ = 5.32 mm^−1
β = 106.271 (5)°	T = 150 K
V = 1546.96 (15) Å^3	Block, colourless
Z = 4	0.2 × 0.2 × 0.15 mm

Data collection

SuperNova, Single source at offset, Eos diffractometer	3034 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	2260 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.046
Detector resolution: 8.0714 pixels mm^-1	θmax = 26.0°, θmin = 3.4°
ω scans	h = −14→16
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −13→12
Tmin = 0.025, Tmax = 1.000	l = −13→13
6191 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.064	w = 1/[σ^2(Fo^2) + (0.0076P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.93	(Δ/σ)max = 0.001
3034 reflections	Δρmax = 0.43 e Å^−3
199 parameters	Δρmin = −0.52 e Å^−3
0 restraints

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.47057 (3)	0.36072 (4)	0.13908 (5)	0.02488 (13)
Br2	−0.07338 (3)	0.33779 (4)	−0.18506 (5)	0.02532 (13)
C1	0.3492 (3)	0.3537 (4)	−0.0077 (5)	0.0282 (12)
C2	0.2501 (3)	0.3426 (4)	0.0330 (4)	0.0202 (10)
C3	0.1478 (3)	0.3489 (4)	−0.0796 (5)	0.0208 (10)
C4	0.0488 (3)	0.3080 (4)	−0.0446 (5)	0.0240 (11)
F1	0.35763 (18)	0.2579 (3)	−0.0792 (3)	0.0613 (10)
F2	0.34425 (18)	0.4521 (3)	−0.0793 (3)	0.0598 (10)
F3	0.25256 (16)	0.2386 (2)	0.0954 (3)	0.0434 (8)
F4	0.24725 (17)	0.4318 (2)	0.1146 (3)	0.0456 (8)
F5	0.15754 (17)	0.2775 (2)	−0.1749 (3)	0.0408 (8)
F6	0.13500 (16)	0.4625 (2)	−0.1215 (3)	0.0398 (8)
F7	0.05584 (16)	0.1913 (2)	−0.0158 (3)	0.0429 (8)
F8	0.04251 (17)	0.3683 (2)	0.0599 (3)	0.0387 (7)
C5	0.6632 (3)	0.2423 (4)	0.4059 (5)	0.0264 (11)
H5A	0.6997	0.1996	0.3510	0.032*
H5B	0.5974	0.1996	0.3992	0.032*
C6	0.5907 (3)	0.4310 (4)	0.4455 (4)	0.0297 (12)
H6A	0.5239	0.3917	0.4415	0.036*
H6B	0.5764	0.5153	0.4154	0.036*
C7	0.7404 (3)	0.4287 (4)	0.3691 (4)	0.0255 (11)
H7A	0.7268	0.5133	0.3400	0.031*
H7B	0.7763	0.3881	0.3122	0.031*
C8	0.7308 (3)	0.2414 (4)	0.5477 (5)	0.0291 (12)
H8A	0.6929	0.2007	0.6023	0.035*
H8B	0.7950	0.1953	0.5541	0.035*
C9	0.6604 (3)	0.4305 (4)	0.5864 (5)	0.0317 (12)
H9A	0.6763	0.5145	0.6166	0.038*
H9B	0.6233	0.3912	0.6428	0.038*
C10	0.8092 (3)	0.4258 (4)	0.5097 (5)	0.0309 (12)
H10A	0.8745	0.3831	0.5132	0.037*
H10B	0.8266	0.5094	0.5403	0.037*
N1	0.6416 (2)	0.3667 (3)	0.3606 (3)	0.0222 (9)
N2	0.7574 (2)	0.3650 (3)	0.5949 (4)	0.0219 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0157 (2)	0.0345 (3)	0.0208 (3)	−0.00078 (18)	−0.0007 (2)	0.0013 (2)
Br2	0.0159 (2)	0.0321 (3)	0.0241 (3)	−0.00058 (18)	−0.0007 (2)	−0.0016 (2)
C1	0.018 (2)	0.043 (3)	0.020 (3)	0.001 (2)	0.000 (2)	0.000 (3)
C2	0.022 (2)	0.020 (2)	0.015 (3)	−0.0026 (18)	−0.001 (2)	−0.004 (2)
C3	0.021 (2)	0.022 (2)	0.017 (3)	0.0005 (19)	0.001 (2)	0.002 (2)
C4	0.020 (2)	0.023 (2)	0.025 (3)	0.0026 (19)	0.001 (2)	0.002 (2)
F1	0.0250 (15)	0.104 (3)	0.049 (2)	0.0131 (15)	0.0010 (15)	−0.044 (2)
F2	0.0290 (15)	0.093 (2)	0.048 (2)	−0.0155 (15)	−0.0049 (15)	0.051 (2)
F3	0.0267 (14)	0.0503 (17)	0.043 (2)	−0.0060 (12)	−0.0069 (14)	0.0314 (17)
F4	0.0265 (14)	0.0638 (19)	0.040 (2)	0.0065 (13)	−0.0023 (14)	−0.0322 (18)
F5	0.0251 (14)	0.075 (2)	0.0210 (18)	0.0005 (13)	0.0039 (13)	−0.0220 (17)
F6	0.0230 (13)	0.0348 (15)	0.052 (2)	−0.0015 (11)	−0.0045 (14)	0.0251 (16)
F7	0.0246 (14)	0.0327 (15)	0.066 (3)	−0.0047 (12)	0.0033 (15)	0.0202 (16)
F8	0.0263 (14)	0.070 (2)	0.0196 (17)	0.0058 (13)	0.0058 (13)	−0.0084 (17)
C5	0.027 (2)	0.028 (3)	0.022 (3)	−0.001 (2)	0.003 (2)	−0.003 (2)
C6	0.026 (2)	0.041 (3)	0.021 (3)	0.008 (2)	0.003 (2)	0.003 (3)
C7	0.022 (2)	0.031 (3)	0.022 (3)	−0.004 (2)	0.004 (2)	0.000 (2)
C8	0.031 (2)	0.027 (3)	0.025 (3)	0.002 (2)	−0.001 (2)	−0.003 (2)
C9	0.026 (2)	0.046 (3)	0.022 (3)	0.010 (2)	0.006 (2)	−0.002 (3)
C10	0.023 (2)	0.036 (3)	0.030 (3)	−0.005 (2)	0.003 (2)	0.004 (3)
N1	0.0214 (18)	0.030 (2)	0.014 (2)	0.0003 (16)	0.0032 (17)	−0.0002 (19)
N2	0.0183 (18)	0.027 (2)	0.019 (2)	−0.0008 (15)	0.0032 (17)	−0.0009 (19)

Geometric parameters (Å, º)

Br1—C1	1.933 (4)	C6—H6A	0.9900
Br2—C4	1.928 (4)	C6—H6B	0.9900
C1—C2	1.523 (5)	C6—C9	1.547 (6)
C1—F1	1.336 (5)	C6—N1	1.472 (5)
C1—F2	1.328 (5)	C7—H7A	0.9900
C2—C3	1.562 (5)	C7—H7B	0.9900
C2—F3	1.331 (4)	C7—C10	1.541 (6)
C2—F4	1.333 (4)	C7—N1	1.477 (4)
C3—C4	1.551 (5)	C8—H8A	0.9900
C3—F5	1.334 (5)	C8—H8B	0.9900
C3—F6	1.333 (4)	C8—N2	1.471 (5)
C4—F7	1.328 (4)	C9—H9A	0.9900
C4—F8	1.334 (5)	C9—H9B	0.9900
C5—H5A	0.9900	C9—N2	1.475 (4)
C5—H5B	0.9900	C10—H10A	0.9900
C5—C8	1.546 (6)	C10—H10B	0.9900
C5—N1	1.465 (5)	C10—N2	1.465 (5)
C2—C1—Br1	112.0 (3)	N1—C6—H6A	109.5
F1—C1—Br1	108.5 (3)	N1—C6—H6B	109.5
F1—C1—C2	109.0 (3)	N1—C6—C9	110.5 (3)
F2—C1—Br1	109.7 (3)	H7A—C7—H7B	108.2
F2—C1—C2	109.2 (3)	C10—C7—H7A	109.8
F2—C1—F1	108.4 (4)	C10—C7—H7B	109.8
C1—C2—C3	115.2 (4)	N1—C7—H7A	109.8
F3—C2—C1	108.4 (3)	N1—C7—H7B	109.8
F3—C2—C3	108.9 (3)	N1—C7—C10	109.5 (3)
F3—C2—F4	108.0 (4)	C5—C8—H8A	109.5
F4—C2—C1	108.7 (3)	C5—C8—H8B	109.5
F4—C2—C3	107.4 (3)	H8A—C8—H8B	108.1
C4—C3—C2	115.4 (4)	N2—C8—C5	110.8 (3)
F5—C3—C2	108.5 (3)	N2—C8—H8A	109.5
F5—C3—C4	107.0 (3)	N2—C8—H8B	109.5
F6—C3—C2	107.9 (3)	C6—C9—H9A	109.6
F6—C3—C4	108.7 (3)	C6—C9—H9B	109.6
F6—C3—F5	109.3 (4)	H9A—C9—H9B	108.1
C3—C4—Br2	111.2 (3)	N2—C9—C6	110.2 (4)
F7—C4—Br2	109.9 (3)	N2—C9—H9A	109.6
F7—C4—C3	109.4 (3)	N2—C9—H9B	109.6
F7—C4—F8	107.9 (4)	C7—C10—H10A	109.3
F8—C4—Br2	109.7 (3)	C7—C10—H10B	109.3
F8—C4—C3	108.8 (3)	H10A—C10—H10B	108.0
H5A—C5—H5B	108.2	N2—C10—C7	111.6 (3)
C8—C5—H5A	109.6	N2—C10—H10A	109.3
C8—C5—H5B	109.6	N2—C10—H10B	109.3
N1—C5—H5A	109.6	C5—N1—C6	109.4 (3)
N1—C5—H5B	109.6	C5—N1—C7	109.0 (3)
N1—C5—C8	110.1 (3)	C6—N1—C7	107.7 (3)
H6A—C6—H6B	108.1	C8—N2—C9	108.1 (3)
C9—C6—H6A	109.5	C10—N2—C8	108.8 (3)
C9—C6—H6B	109.5	C10—N2—C9	107.7 (3)
Br1—C1—C2—C3	174.3 (3)	F5—C3—C4—Br2	−65.9 (4)
Br1—C1—C2—F3	−63.4 (4)	F5—C3—C4—F7	55.6 (5)
Br1—C1—C2—F4	53.8 (4)	F5—C3—C4—F8	173.2 (3)
C1—C2—C3—C4	166.2 (4)	F6—C3—C4—Br2	51.9 (4)
C1—C2—C3—F5	46.2 (5)	F6—C3—C4—F7	173.4 (4)
C1—C2—C3—F6	−72.1 (4)	F6—C3—C4—F8	−69.0 (5)
C2—C3—C4—Br2	173.3 (3)	C5—C8—N2—C9	60.2 (4)
C2—C3—C4—F7	−65.2 (5)	C5—C8—N2—C10	−56.5 (4)
C2—C3—C4—F8	52.4 (5)	C6—C9—N2—C8	−58.5 (5)
F1—C1—C2—C3	−65.6 (5)	C6—C9—N2—C10	59.0 (4)
F1—C1—C2—F3	56.7 (5)	C7—C10—N2—C8	58.4 (4)
F1—C1—C2—F4	173.9 (4)	C7—C10—N2—C9	−58.6 (4)
F2—C1—C2—C3	52.6 (5)	C8—C5—N1—C6	−57.3 (4)
F2—C1—C2—F3	174.9 (4)	C8—C5—N1—C7	60.3 (4)
F2—C1—C2—F4	−67.9 (5)	C9—C6—N1—C5	58.8 (4)
F3—C2—C3—C4	44.2 (5)	C9—C6—N1—C7	−59.5 (4)
F3—C2—C3—F5	−75.8 (4)	C10—C7—N1—C5	−58.5 (4)
F3—C2—C3—F6	165.9 (3)	C10—C7—N1—C6	60.0 (4)
F4—C2—C3—C4	−72.6 (4)	N1—C5—C8—N2	−2.2 (5)
F4—C2—C3—F5	167.4 (3)	N1—C6—C9—N2	−0.3 (5)
F4—C2—C3—F6	49.1 (4)	N1—C7—C10—N2	−1.0 (5)

1,6-Dibromoperfluorohexane–1,4-diazabicyclo[2.2.2]octane (1/1) (II)

Crystal data

C6Br2F12·C6H12N2	Z = 2
Mr = 572.06	F(000) = 552
Triclinic, P1	Dx = 2.121 Mg m^−3
a = 6.0096 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.4941 (8) Å	Cell parameters from 4386 reflections
c = 14.5016 (11) Å	θ = 3.9–27.1°
α = 92.051 (6)°	µ = 4.64 mm^−1
β = 101.375 (6)°	T = 100 K
γ = 90.507 (6)°	Block, colourless
V = 895.89 (11) Å^3	0.18 × 0.16 × 0.12 mm

Data collection

Xcalibur, Atlas diffractometer	3504 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2686 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
Detector resolution: 5.1636 pixels mm^-1	θmax = 26.0°, θmin = 3.4°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −12→12
Tmin = 0.769, Tmax = 1.000	l = −17→17
12221 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.049	H-atom parameters constrained
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + (0.021P)^2 + 2.803P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max = 0.001
3504 reflections	Δρmax = 0.94 e Å^−3
253 parameters	Δρmin = −0.72 e Å^−3
0 restraints

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.69172 (9)	0.45860 (5)	0.79186 (4)	0.01867 (17)
Br2	−0.13706 (9)	0.04259 (5)	0.20985 (4)	0.01959 (17)
F1	0.7975 (6)	0.4096 (5)	0.6225 (3)	0.0554 (14)
F2	0.7593 (7)	0.2410 (4)	0.6992 (3)	0.0600 (15)
F3	0.3387 (6)	0.4527 (4)	0.6086 (3)	0.0399 (10)
F4	0.3091 (7)	0.2778 (4)	0.6799 (2)	0.0442 (11)
F5	0.5053 (6)	0.3254 (4)	0.4718 (2)	0.0383 (10)
F6	0.4927 (6)	0.1494 (3)	0.5435 (3)	0.0388 (10)
F7	0.0458 (6)	0.3529 (3)	0.4598 (3)	0.0350 (10)
F8	0.0337 (6)	0.1758 (4)	0.5308 (2)	0.0326 (9)
F9	0.2375 (7)	0.2223 (4)	0.3250 (3)	0.0463 (12)
F10	0.2026 (6)	0.0481 (4)	0.3960 (3)	0.0392 (10)
F11	−0.2157 (8)	0.2589 (4)	0.3024 (3)	0.0672 (16)
F12	−0.2544 (6)	0.0894 (5)	0.3777 (3)	0.0560 (14)
C1	0.6716 (10)	0.3545 (6)	0.6780 (4)	0.0257 (15)
C2	0.4245 (9)	0.3390 (5)	0.6239 (4)	0.0166 (12)
C3	0.3941 (10)	0.2621 (6)	0.5280 (4)	0.0197 (13)
C4	0.1466 (9)	0.2400 (6)	0.4751 (4)	0.0182 (13)
C5	0.1192 (9)	0.1627 (6)	0.3800 (4)	0.0182 (13)
C6	−0.1253 (10)	0.1463 (6)	0.3240 (4)	0.0263 (15)
N1	0.7560 (7)	0.6409 (4)	0.9540 (3)	0.0157 (10)
N2	0.8071 (7)	0.8576 (4)	1.0479 (3)	0.0135 (10)
C7	0.9959 (8)	0.6855 (5)	0.9717 (4)	0.0154 (12)
H7A	1.0448	0.6926	0.9122	0.019*
H7B	1.0910	0.6238	1.0084	0.019*
C8	1.0238 (9)	0.8163 (6)	1.0254 (4)	0.0185 (13)
H8A	1.1358	0.8103	1.0831	0.022*
H8B	1.0779	0.8791	0.9871	0.022*
C9	0.6153 (9)	0.7392 (5)	0.9010 (4)	0.0175 (13)
H9A	0.4574	0.7116	0.8877	0.021*
H9B	0.6623	0.7507	0.8415	0.021*
C10	0.6408 (9)	0.8669 (5)	0.9587 (4)	0.0184 (13)
H10A	0.6897	0.9332	0.9218	0.022*
H10B	0.4947	0.8906	0.9724	0.022*
C11	0.6861 (9)	0.6296 (5)	1.0452 (4)	0.0166 (12)
H11A	0.7724	0.5633	1.0803	0.020*
H11B	0.5265	0.6057	1.0346	0.020*
C12	0.7259 (9)	0.7576 (5)	1.1030 (4)	0.0190 (13)
H12A	0.5852	0.7841	1.1206	0.023*
H12B	0.8372	0.7462	1.1602	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0226 (3)	0.0185 (4)	0.0139 (3)	−0.0010 (2)	0.0020 (2)	−0.0039 (2)
Br2	0.0238 (3)	0.0191 (4)	0.0138 (3)	0.0006 (2)	−0.0006 (2)	−0.0040 (2)
F1	0.029 (2)	0.109 (4)	0.030 (2)	−0.026 (2)	0.0163 (19)	−0.030 (2)
F2	0.063 (3)	0.039 (3)	0.057 (3)	0.034 (2)	−0.037 (2)	−0.027 (2)
F3	0.048 (2)	0.027 (2)	0.035 (2)	0.0166 (18)	−0.0128 (19)	−0.0137 (18)
F4	0.047 (2)	0.068 (3)	0.018 (2)	−0.033 (2)	0.0093 (18)	−0.006 (2)
F5	0.033 (2)	0.067 (3)	0.0161 (19)	−0.0233 (19)	0.0109 (16)	−0.0084 (19)
F6	0.042 (2)	0.023 (2)	0.041 (2)	0.0170 (17)	−0.0157 (18)	−0.0147 (18)
F7	0.038 (2)	0.027 (2)	0.032 (2)	0.0178 (16)	−0.0109 (17)	−0.0101 (17)
F8	0.030 (2)	0.053 (3)	0.0147 (18)	−0.0173 (17)	0.0070 (16)	−0.0038 (17)
F9	0.054 (3)	0.067 (3)	0.021 (2)	−0.036 (2)	0.0193 (19)	−0.011 (2)
F10	0.048 (2)	0.025 (2)	0.034 (2)	0.0192 (17)	−0.0139 (18)	−0.0131 (18)
F11	0.078 (3)	0.043 (3)	0.056 (3)	0.043 (2)	−0.043 (3)	−0.032 (2)
F12	0.030 (2)	0.107 (4)	0.032 (2)	−0.023 (2)	0.0144 (19)	−0.033 (2)
C1	0.030 (3)	0.025 (4)	0.021 (3)	0.004 (3)	0.003 (3)	−0.007 (3)
C2	0.020 (3)	0.015 (3)	0.015 (3)	0.001 (2)	0.004 (2)	0.002 (2)
C3	0.024 (3)	0.015 (3)	0.022 (3)	0.001 (2)	0.010 (3)	−0.002 (3)
C4	0.019 (3)	0.019 (3)	0.017 (3)	−0.001 (2)	0.003 (2)	0.003 (3)
C5	0.017 (3)	0.022 (4)	0.016 (3)	0.000 (2)	0.004 (2)	0.001 (3)
C6	0.024 (3)	0.028 (4)	0.025 (4)	0.007 (3)	0.001 (3)	−0.006 (3)
N1	0.016 (2)	0.017 (3)	0.013 (2)	−0.0002 (19)	0.001 (2)	−0.004 (2)
N2	0.016 (2)	0.008 (3)	0.016 (2)	−0.0036 (18)	0.0005 (19)	−0.0035 (19)
C7	0.012 (3)	0.019 (3)	0.014 (3)	0.003 (2)	0.001 (2)	−0.002 (2)
C8	0.017 (3)	0.023 (4)	0.014 (3)	−0.001 (2)	−0.001 (2)	0.001 (2)
C9	0.020 (3)	0.013 (3)	0.016 (3)	0.001 (2)	−0.003 (2)	−0.006 (2)
C10	0.022 (3)	0.016 (3)	0.016 (3)	0.005 (2)	0.001 (2)	−0.001 (2)
C11	0.019 (3)	0.012 (3)	0.019 (3)	−0.006 (2)	0.006 (2)	−0.002 (2)
C12	0.017 (3)	0.020 (3)	0.020 (3)	0.000 (2)	0.004 (2)	−0.001 (3)

Geometric parameters (Å, º)

Br1—C1	1.930 (6)	N1—C9	1.479 (7)
Br2—C6	1.937 (6)	N1—C11	1.472 (7)
F1—C1	1.349 (7)	N2—C8	1.468 (7)
F2—C1	1.328 (7)	N2—C10	1.476 (7)
F3—C2	1.313 (6)	N2—C12	1.477 (7)
F4—C2	1.343 (6)	C7—H7A	0.9700
F5—C3	1.341 (7)	C7—H7B	0.9700
F6—C3	1.334 (7)	C7—C8	1.545 (7)
F7—C4	1.341 (7)	C8—H8A	0.9700
F8—C4	1.346 (6)	C8—H8B	0.9700
F9—C5	1.337 (6)	C9—H9A	0.9700
F10—C5	1.318 (7)	C9—H9B	0.9700
F11—C6	1.327 (7)	C9—C10	1.545 (7)
F12—C6	1.351 (8)	C10—H10A	0.9700
C1—C2	1.541 (8)	C10—H10B	0.9700
C2—C3	1.560 (8)	C11—H11A	0.9700
C3—C4	1.545 (8)	C11—H11B	0.9700
C4—C5	1.553 (8)	C11—C12	1.549 (7)
C5—C6	1.537 (8)	C12—H12A	0.9700
N1—C7	1.482 (6)	C12—H12B	0.9700
F1—C1—Br1	108.9 (4)	C8—N2—C10	108.2 (4)
F1—C1—C2	109.2 (5)	C8—N2—C12	107.9 (4)
F2—C1—Br1	109.5 (4)	C10—N2—C12	108.0 (4)
F2—C1—F1	107.4 (5)	N1—C7—H7A	109.5
F2—C1—C2	110.1 (5)	N1—C7—H7B	109.5
C2—C1—Br1	111.6 (4)	N1—C7—C8	110.8 (4)
F3—C2—F4	109.0 (5)	H7A—C7—H7B	108.1
F3—C2—C1	108.7 (5)	C8—C7—H7A	109.5
F3—C2—C3	108.7 (5)	C8—C7—H7B	109.5
F4—C2—C1	107.0 (5)	N2—C8—C7	110.8 (4)
F4—C2—C3	108.3 (4)	N2—C8—H8A	109.5
C1—C2—C3	115.0 (5)	N2—C8—H8B	109.5
F5—C3—C2	107.9 (4)	C7—C8—H8A	109.5
F5—C3—C4	108.0 (5)	C7—C8—H8B	109.5
F6—C3—F5	107.7 (5)	H8A—C8—H8B	108.1
F6—C3—C2	108.4 (5)	N1—C9—H9A	109.6
F6—C3—C4	108.9 (4)	N1—C9—H9B	109.6
C4—C3—C2	115.7 (5)	N1—C9—C10	110.1 (4)
F7—C4—F8	107.2 (5)	H9A—C9—H9B	108.1
F7—C4—C3	109.3 (4)	C10—C9—H9A	109.6
F7—C4—C5	109.0 (5)	C10—C9—H9B	109.6
F8—C4—C3	108.4 (4)	N2—C10—C9	111.3 (4)
F8—C4—C5	107.5 (4)	N2—C10—H10A	109.4
C3—C4—C5	115.1 (5)	N2—C10—H10B	109.4
F9—C5—C4	108.4 (5)	C9—C10—H10A	109.4
F9—C5—C6	106.9 (5)	C9—C10—H10B	109.4
F10—C5—F9	108.8 (5)	H10A—C10—H10B	108.0
F10—C5—C4	109.1 (5)	N1—C11—H11A	109.5
F10—C5—C6	107.8 (5)	N1—C11—H11B	109.5
C6—C5—C4	115.6 (5)	N1—C11—C12	110.6 (4)
F11—C6—Br2	109.5 (4)	H11A—C11—H11B	108.1
F11—C6—F12	107.1 (5)	C12—C11—H11A	109.5
F11—C6—C5	110.6 (5)	C12—C11—H11B	109.5
F12—C6—Br2	108.7 (4)	N2—C12—C11	110.8 (4)
F12—C6—C5	109.4 (5)	N2—C12—H12A	109.5
C5—C6—Br2	111.5 (4)	N2—C12—H12B	109.5
C9—N1—C7	108.0 (4)	C11—C12—H12A	109.5
C11—N1—C7	108.5 (4)	C11—C12—H12B	109.5
C11—N1—C9	108.1 (4)	H12A—C12—H12B	108.1
Br1—C1—C2—F3	54.7 (6)	F10—C5—C6—Br2	−55.4 (6)
Br1—C1—C2—F4	−62.8 (5)	F10—C5—C6—F11	−177.4 (5)
Br1—C1—C2—C3	176.8 (4)	F10—C5—C6—F12	64.9 (6)
F1—C1—C2—F3	−65.8 (6)	C1—C2—C3—F5	−61.8 (6)
F1—C1—C2—F4	176.7 (5)	C1—C2—C3—F6	54.6 (6)
F1—C1—C2—C3	56.3 (7)	C1—C2—C3—C4	177.2 (5)
F2—C1—C2—F3	176.6 (5)	C2—C3—C4—F7	57.3 (6)
F2—C1—C2—F4	59.1 (6)	C2—C3—C4—F8	−59.3 (6)
F2—C1—C2—C3	−61.3 (7)	C2—C3—C4—C5	−179.7 (5)
F3—C2—C3—F5	60.3 (6)	C3—C4—C5—F9	−56.7 (6)
F3—C2—C3—F6	176.6 (4)	C3—C4—C5—F10	61.6 (6)
F3—C2—C3—C4	−60.8 (6)	C3—C4—C5—C6	−176.8 (5)
F4—C2—C3—F5	178.6 (5)	C4—C5—C6—Br2	−177.7 (4)
F4—C2—C3—F6	−65.1 (6)	C4—C5—C6—F11	60.3 (7)
F4—C2—C3—C4	57.5 (6)	C4—C5—C6—F12	−57.4 (7)
F5—C3—C4—F7	−63.7 (6)	N1—C7—C8—N2	2.6 (6)
F5—C3—C4—F8	179.7 (5)	N1—C9—C10—N2	3.2 (6)
F5—C3—C4—C5	59.3 (6)	N1—C11—C12—N2	4.1 (6)
F6—C3—C4—F7	179.6 (5)	C7—N1—C9—C10	−60.1 (5)
F6—C3—C4—F8	63.0 (6)	C7—N1—C11—C12	55.6 (6)
F6—C3—C4—C5	−57.4 (6)	C8—N2—C10—C9	56.6 (6)
F7—C4—C5—F9	66.4 (6)	C8—N2—C12—C11	−61.1 (5)
F7—C4—C5—F10	−175.2 (4)	C9—N1—C7—C8	57.2 (5)
F7—C4—C5—C6	−53.6 (7)	C9—N1—C11—C12	−61.3 (5)
F8—C4—C5—F9	−177.6 (5)	C10—N2—C8—C7	−59.6 (6)
F8—C4—C5—F10	−59.3 (6)	C10—N2—C12—C11	55.7 (6)
F8—C4—C5—C6	62.3 (7)	C11—N1—C7—C8	−59.7 (6)
F9—C5—C6—Br2	61.5 (6)	C11—N1—C9—C10	57.1 (5)
F9—C5—C6—F11	−60.6 (7)	C12—N2—C8—C7	57.0 (6)
F9—C5—C6—F12	−178.3 (5)	C12—N2—C10—C9	−60.0 (6)

1,8-Dibromoperfluorooctane–1,4-diazabicyclo[2.2.2]octane (1/1) (III)

Crystal data

C8Br2F16·C6H12N2	Z = 2
Mr = 672.08	F(000) = 648
Triclinic, P1	Dx = 2.157 Mg m^−3
a = 6.03367 (19) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.4836 (5) Å	Cell parameters from 4902 reflections
c = 16.4471 (9) Å	θ = 3.7–28.5°
α = 88.785 (4)°	µ = 4.07 mm^−1
β = 84.126 (3)°	T = 150 K
γ = 89.724 (3)°	Plate, colourless
V = 1034.65 (8) Å^3	0.14 × 0.08 × 0.04 mm

Data collection

SuperNova Single source at offset Eos diffractometer	4680 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3723 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.042
Detector resolution: 8.0714 pixels mm^-1	θmax = 27.5°, θmin = 3.4°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −13→13
Tmin = 0.622, Tmax = 1.000	l = −20→21
14918 measured reflections

Refinement

Refinement on F^2	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.122	w = 1/[σ^2(Fo^2) + (0.0543P)^2 + 1.8052P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
4680 reflections	Δρmax = 1.01 e Å^−3
307 parameters	Δρmin = −0.69 e Å^−3
0 restraints

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	1.23740 (7)	0.52567 (4)	0.18081 (3)	0.02372 (14)
Br2	0.31570 (7)	0.97270 (4)	0.81774 (3)	0.02532 (14)
F1	1.3167 (7)	0.7383 (4)	0.2593 (3)	0.0833 (16)
F2	1.3831 (5)	0.5669 (5)	0.3265 (2)	0.0725 (13)
F3	0.8768 (5)	0.6934 (4)	0.28024 (19)	0.0543 (10)
F4	0.9322 (5)	0.5136 (3)	0.34060 (19)	0.0451 (8)
F5	1.0979 (5)	0.8127 (3)	0.3973 (2)	0.0527 (10)
F6	1.1252 (5)	0.6296 (3)	0.45864 (18)	0.0488 (9)
F7	0.6478 (5)	0.7905 (3)	0.40831 (18)	0.0478 (9)
F8	0.6682 (5)	0.6037 (3)	0.4658 (2)	0.0432 (8)
F9	0.8583 (5)	0.8949 (3)	0.5291 (2)	0.0516 (10)
F10	0.8853 (5)	0.7085 (3)	0.58647 (18)	0.0528 (10)
F11	0.4022 (5)	0.8649 (4)	0.53924 (19)	0.0505 (9)
F12	0.4369 (5)	0.6839 (3)	0.6011 (2)	0.0546 (10)
F13	0.5997 (6)	0.9860 (3)	0.6536 (2)	0.0494 (9)
F14	0.6676 (6)	0.8086 (4)	0.71488 (19)	0.0603 (11)
F15	0.1540 (5)	0.9307 (5)	0.6751 (2)	0.0803 (15)
F16	0.2275 (8)	0.7598 (4)	0.7402 (3)	0.098 (2)
C7	1.2412 (8)	0.6223 (5)	0.2782 (3)	0.0330 (11)
C8	1.0085 (6)	0.6313 (4)	0.3270 (3)	0.0208 (9)
C9	1.0034 (7)	0.6992 (4)	0.4097 (3)	0.0228 (9)
C10	0.7661 (7)	0.7177 (4)	0.4556 (3)	0.0206 (9)
C11	0.7649 (7)	0.7810 (4)	0.5399 (3)	0.0225 (9)
C12	0.5298 (7)	0.7974 (4)	0.5869 (3)	0.0242 (9)
C13	0.5292 (7)	0.8682 (4)	0.6694 (3)	0.0219 (9)
C14	0.3021 (8)	0.8752 (5)	0.7208 (3)	0.0378 (13)
N1	0.7315 (5)	0.6447 (3)	−0.0400 (2)	0.0189 (7)
N2	0.7042 (5)	0.8534 (3)	0.0414 (2)	0.0189 (7)
C1	0.8227 (7)	0.6268 (4)	0.0389 (3)	0.0238 (9)
H1A	0.9790	0.6037	0.0296	0.029*
H1B	0.7448	0.5575	0.0696	0.029*
C2	0.4988 (6)	0.6868 (4)	−0.0243 (3)	0.0217 (9)
H2A	0.4133	0.6216	0.0075	0.026*
H2B	0.4356	0.6983	−0.0759	0.026*
C3	0.8580 (7)	0.7475 (4)	−0.0859 (3)	0.0238 (9)
H3A	0.7961	0.7640	−0.1372	0.029*
H3B	1.0119	0.7211	−0.0981	0.029*
C4	0.8483 (7)	0.8712 (4)	−0.0353 (3)	0.0243 (9)
H4A	0.9972	0.8935	−0.0233	0.029*
H4B	0.7914	0.9409	−0.0670	0.029*
C5	0.4823 (6)	0.8127 (4)	0.0220 (3)	0.0217 (9)
H5A	0.4188	0.8783	−0.0111	0.026*
H5B	0.3845	0.8016	0.0723	0.026*
C6	0.7980 (7)	0.7497 (4)	0.0891 (3)	0.0242 (9)
H6A	0.7012	0.7336	0.1390	0.029*
H6B	0.9427	0.7750	0.1040	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0275 (2)	0.0276 (3)	0.0159 (2)	0.00098 (16)	−0.00033 (16)	−0.00486 (18)
Br2	0.0299 (2)	0.0282 (3)	0.0170 (3)	−0.00127 (17)	0.00269 (17)	−0.00512 (18)
F1	0.106 (3)	0.060 (2)	0.071 (3)	−0.059 (2)	0.064 (2)	−0.044 (2)
F2	0.0323 (17)	0.149 (4)	0.040 (2)	0.029 (2)	−0.0150 (15)	−0.043 (2)
F3	0.059 (2)	0.087 (3)	0.0182 (17)	0.0405 (18)	−0.0105 (14)	−0.0067 (16)
F4	0.064 (2)	0.0318 (16)	0.0356 (19)	−0.0178 (14)	0.0164 (15)	−0.0122 (14)
F5	0.0584 (19)	0.0421 (18)	0.052 (2)	−0.0298 (15)	0.0295 (16)	−0.0262 (16)
F6	0.0370 (16)	0.093 (3)	0.0180 (16)	0.0294 (16)	−0.0096 (12)	−0.0065 (16)
F7	0.0454 (17)	0.080 (2)	0.0193 (16)	0.0333 (16)	−0.0079 (13)	−0.0037 (15)
F8	0.0454 (17)	0.0393 (17)	0.0413 (19)	−0.0196 (13)	0.0169 (14)	−0.0185 (14)
F9	0.0539 (18)	0.0433 (18)	0.052 (2)	−0.0283 (14)	0.0289 (16)	−0.0260 (16)
F10	0.0505 (18)	0.092 (3)	0.0169 (16)	0.0429 (18)	−0.0122 (13)	−0.0055 (16)
F11	0.0364 (16)	0.093 (3)	0.0236 (17)	0.0310 (16)	−0.0106 (13)	−0.0121 (17)
F12	0.063 (2)	0.0417 (18)	0.052 (2)	−0.0320 (15)	0.0318 (17)	−0.0249 (16)
F13	0.072 (2)	0.0342 (17)	0.0369 (19)	−0.0213 (15)	0.0241 (16)	−0.0136 (14)
F14	0.062 (2)	0.101 (3)	0.0196 (17)	0.049 (2)	−0.0153 (15)	−0.0143 (18)
F15	0.0312 (17)	0.165 (4)	0.049 (2)	0.033 (2)	−0.0147 (16)	−0.055 (3)
F16	0.133 (4)	0.071 (3)	0.075 (3)	−0.073 (3)	0.077 (3)	−0.050 (2)
C7	0.032 (2)	0.046 (3)	0.021 (3)	−0.009 (2)	0.0049 (19)	−0.012 (2)
C8	0.021 (2)	0.023 (2)	0.018 (2)	−0.0001 (16)	−0.0047 (16)	−0.0028 (18)
C9	0.021 (2)	0.029 (2)	0.018 (2)	−0.0047 (17)	−0.0010 (16)	−0.0028 (18)
C10	0.023 (2)	0.026 (2)	0.013 (2)	−0.0003 (16)	−0.0043 (16)	−0.0019 (17)
C11	0.022 (2)	0.027 (2)	0.019 (2)	−0.0018 (16)	−0.0033 (17)	−0.0048 (19)
C12	0.025 (2)	0.028 (2)	0.019 (2)	−0.0044 (17)	0.0010 (17)	−0.0046 (19)
C13	0.023 (2)	0.024 (2)	0.019 (2)	−0.0018 (16)	−0.0033 (16)	0.0005 (18)
C14	0.035 (3)	0.047 (3)	0.029 (3)	−0.012 (2)	0.012 (2)	−0.017 (2)
N1	0.0191 (16)	0.0215 (18)	0.0164 (19)	−0.0004 (13)	−0.0025 (13)	−0.0072 (15)
N2	0.0208 (17)	0.0172 (17)	0.018 (2)	0.0011 (13)	−0.0004 (13)	−0.0043 (14)
C1	0.030 (2)	0.021 (2)	0.022 (2)	0.0070 (17)	−0.0097 (18)	−0.0025 (18)
C2	0.0173 (19)	0.025 (2)	0.023 (2)	−0.0029 (15)	−0.0036 (16)	−0.0046 (18)
C3	0.026 (2)	0.025 (2)	0.019 (2)	−0.0050 (17)	0.0036 (17)	−0.0069 (18)
C4	0.025 (2)	0.022 (2)	0.024 (3)	−0.0053 (16)	0.0036 (17)	−0.0060 (18)
C5	0.0177 (19)	0.027 (2)	0.021 (2)	0.0033 (16)	−0.0028 (16)	−0.0040 (18)
C6	0.031 (2)	0.023 (2)	0.020 (2)	0.0058 (17)	−0.0081 (18)	−0.0033 (18)

Geometric parameters (Å, º)

Br1—C7	1.915 (5)	C12—C13	1.560 (6)
Br2—C14	1.921 (5)	C13—C14	1.537 (6)
F1—C7	1.321 (6)	N1—C1	1.469 (5)
F2—C7	1.347 (6)	N1—C2	1.469 (5)
F3—C8	1.321 (5)	N1—C3	1.472 (5)
F4—C8	1.326 (5)	N2—C4	1.466 (5)
F5—C9	1.325 (5)	N2—C5	1.474 (5)
F6—C9	1.346 (5)	N2—C6	1.471 (5)
F7—C10	1.334 (5)	C1—H1A	0.9700
F8—C10	1.336 (5)	C1—H1B	0.9700
F9—C11	1.323 (5)	C1—C6	1.543 (6)
F10—C11	1.333 (5)	C2—H2A	0.9700
F11—C12	1.343 (5)	C2—H2B	0.9700
F12—C12	1.323 (5)	C2—C5	1.536 (5)
F13—C13	1.320 (5)	C3—H3A	0.9700
F14—C13	1.323 (5)	C3—H3B	0.9700
F15—C14	1.348 (7)	C3—C4	1.554 (6)
F16—C14	1.314 (6)	C4—H4A	0.9700
C7—C8	1.547 (6)	C4—H4B	0.9700
C8—C9	1.547 (6)	C5—H5A	0.9700
C9—C10	1.562 (6)	C5—H5B	0.9700
C10—C11	1.549 (6)	C6—H6A	0.9700
C11—C12	1.555 (6)	C6—H6B	0.9700
F1—C7—Br1	109.7 (3)	F16—C14—F15	106.7 (5)
F1—C7—F2	107.2 (5)	F16—C14—C13	110.3 (4)
F1—C7—C8	109.4 (4)	C13—C14—Br2	112.0 (3)
F2—C7—Br1	109.2 (3)	C1—N1—C3	108.0 (3)
F2—C7—C8	108.7 (4)	C2—N1—C1	108.3 (3)
C8—C7—Br1	112.5 (3)	C2—N1—C3	108.0 (3)
F3—C8—F4	108.8 (4)	C4—N2—C5	108.6 (3)
F3—C8—C7	107.4 (4)	C4—N2—C6	108.2 (3)
F3—C8—C9	108.9 (3)	C6—N2—C5	107.8 (3)
F4—C8—C7	107.8 (3)	N1—C1—H1A	109.5
F4—C8—C9	108.7 (4)	N1—C1—H1B	109.5
C9—C8—C7	115.1 (3)	N1—C1—C6	110.9 (3)
F5—C9—F6	108.2 (4)	H1A—C1—H1B	108.0
F5—C9—C8	108.9 (4)	C6—C1—H1A	109.5
F5—C9—C10	108.4 (3)	C6—C1—H1B	109.5
F6—C9—C8	108.1 (3)	N1—C2—H2A	109.4
F6—C9—C10	108.0 (4)	N1—C2—H2B	109.4
C8—C9—C10	115.0 (3)	N1—C2—C5	111.1 (3)
F7—C10—F8	108.4 (4)	H2A—C2—H2B	108.0
F7—C10—C9	108.0 (4)	C5—C2—H2A	109.4
F7—C10—C11	108.6 (3)	C5—C2—H2B	109.4
F8—C10—C9	108.4 (3)	N1—C3—H3A	109.6
F8—C10—C11	109.1 (4)	N1—C3—H3B	109.6
C11—C10—C9	114.2 (3)	N1—C3—C4	110.4 (3)
F9—C11—F10	109.2 (4)	H3A—C3—H3B	108.1
F9—C11—C10	108.7 (4)	C4—C3—H3A	109.6
F9—C11—C12	108.4 (3)	C4—C3—H3B	109.6
F10—C11—C10	108.2 (3)	N2—C4—C3	110.6 (3)
F10—C11—C12	107.6 (4)	N2—C4—H4A	109.5
C10—C11—C12	114.7 (4)	N2—C4—H4B	109.5
F11—C12—C11	108.5 (4)	C3—C4—H4A	109.5
F11—C12—C13	107.7 (3)	C3—C4—H4B	109.5
F12—C12—F11	107.7 (4)	H4A—C4—H4B	108.1
F12—C12—C11	109.4 (3)	N2—C5—C2	110.6 (3)
F12—C12—C13	109.1 (4)	N2—C5—H5A	109.5
C11—C12—C13	114.2 (4)	N2—C5—H5B	109.5
F13—C13—F14	109.1 (4)	C2—C5—H5A	109.5
F13—C13—C12	108.6 (4)	C2—C5—H5B	109.5
F13—C13—C14	108.0 (4)	H5A—C5—H5B	108.1
F14—C13—C12	108.7 (4)	N2—C6—C1	110.5 (4)
F14—C13—C14	107.0 (4)	N2—C6—H6A	109.5
C14—C13—C12	115.4 (4)	N2—C6—H6B	109.5
F15—C14—Br2	108.7 (3)	C1—C6—H6A	109.5
F15—C14—C13	108.7 (4)	C1—C6—H6B	109.5
F16—C14—Br2	110.2 (4)	H6A—C6—H6B	108.1
Br1—C7—C8—F3	−63.1 (4)	F13—C13—C14—Br2	−55.0 (5)
Br1—C7—C8—F4	54.0 (5)	F13—C13—C14—F15	65.2 (5)
Br1—C7—C8—C9	175.5 (3)	F13—C13—C14—F16	−178.2 (5)
F1—C7—C8—F3	59.2 (5)	F14—C13—C14—Br2	62.4 (5)
F1—C7—C8—F4	176.2 (4)	F14—C13—C14—F15	−177.5 (4)
F1—C7—C8—C9	−62.3 (6)	F14—C13—C14—F16	−60.8 (6)
F2—C7—C8—F3	175.9 (4)	C7—C8—C9—F5	53.5 (5)
F2—C7—C8—F4	−67.0 (5)	C7—C8—C9—F6	−63.8 (5)
F2—C7—C8—C9	54.5 (5)	C7—C8—C9—C10	175.4 (4)
F3—C8—C9—F5	−67.1 (5)	C8—C9—C10—F7	−61.4 (5)
F3—C8—C9—F6	175.6 (4)	C8—C9—C10—F8	55.9 (5)
F3—C8—C9—C10	54.8 (5)	C8—C9—C10—C11	177.7 (4)
F4—C8—C9—F5	174.5 (3)	C9—C10—C11—F9	59.7 (5)
F4—C8—C9—F6	57.1 (4)	C9—C10—C11—F10	−58.8 (5)
F4—C8—C9—C10	−63.6 (5)	C9—C10—C11—C12	−178.8 (3)
F5—C9—C10—F7	60.8 (5)	C10—C11—C12—F11	−56.5 (5)
F5—C9—C10—F8	178.0 (4)	C10—C11—C12—F12	60.7 (5)
F5—C9—C10—C11	−60.1 (5)	C10—C11—C12—C13	−176.7 (4)
F6—C9—C10—F7	177.8 (4)	C11—C12—C13—F13	64.0 (5)
F6—C9—C10—F8	−64.9 (4)	C11—C12—C13—F14	−54.6 (5)
F6—C9—C10—C11	56.9 (5)	C11—C12—C13—C14	−174.8 (4)
F7—C10—C11—F9	−60.9 (5)	C12—C13—C14—Br2	−176.6 (3)
F7—C10—C11—F10	−179.4 (3)	C12—C13—C14—F15	−56.4 (5)
F7—C10—C11—C12	60.6 (5)	C12—C13—C14—F16	60.2 (6)
F8—C10—C11—F9	−178.8 (3)	N1—C1—C6—N2	−3.9 (5)
F8—C10—C11—F10	62.7 (4)	N1—C2—C5—N2	−2.6 (5)
F8—C10—C11—C12	−57.3 (5)	N1—C3—C4—N2	−3.7 (5)
F9—C11—C12—F11	65.1 (5)	C1—N1—C2—C5	59.6 (4)
F9—C11—C12—F12	−177.6 (4)	C1—N1—C3—C4	−56.4 (4)
F9—C11—C12—C13	−55.0 (5)	C2—N1—C1—C6	−55.8 (4)
F10—C11—C12—F11	−176.9 (4)	C2—N1—C3—C4	60.5 (4)
F10—C11—C12—F12	−59.6 (5)	C3—N1—C1—C6	60.9 (4)
F10—C11—C12—C13	62.9 (5)	C3—N1—C2—C5	−57.1 (4)
F11—C12—C13—F13	−56.6 (4)	C4—N2—C5—C2	59.9 (4)
F11—C12—C13—F14	−175.2 (4)	C4—N2—C6—C1	−56.5 (4)
F11—C12—C13—C14	64.6 (5)	C5—N2—C4—C3	−56.1 (4)
F12—C12—C13—F13	−173.3 (4)	C5—N2—C6—C1	60.8 (4)
F12—C12—C13—F14	68.1 (5)	C6—N2—C4—C3	60.7 (4)
F12—C12—C13—C14	−52.0 (5)	C6—N2—C5—C2	−57.2 (4)