N,N,N,N-Tetra-kis(2,3,4,5,6-penta-fluoro-benzo-yl)pyridine-2,6-diamine.

The title compound, C(33)H(3)F(20)N(3)O(4), is a highly fluorinated organic imide that was isolated as an unexpected product from the reaction of 2,6-diamino-pyridine with 2,3,4,5,6-penta-fluoro-benzoyl chloride in a 1:2 molar ratio. The mol-ecule is located on a twofold axis and one of its symmetry-independent 2,3,4,5,6-penta-fluoro-benzoyl groups is disordered over two sets of sites, the occupancy of the major component being 0.773 (3). In the major component, the dihedral angle between the perfluoro-phenyl groups is 63.64 (10)°, and these groups form dihedral angles of 67.14 (7) and 21.1 (2)° with the pyridine core. Short inter-molecular C-H⋯O and C-H⋯N contacts are found in the crystal structure.

Related literature

For preparation of 2-acyl­amino­pyridines and their structures, see: Ośmiałowski et al. (2010a ▶,b ▶). For related structures, see: Kovalevsky et al. (1999 ▶).

Experimental

Crystal data

C33H3F20N3O4

M = 885.38

Monoclinic,

a = 21.2370 (5) Å

b = 6.3940 (1) Å

c = 23.1045 (5) Å

β = 100.585 (1)°

V = 3083.96 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 123 K

0.30 × 0.18 × 0.16 mm

Data collection

Bruker–Nonius KappaCCD with an APEXII detector diffractometer

7138 measured reflections

3785 independent reflections

2526 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.133

S = 1.05

3785 reflections

366 parameters

97 restraints

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.42 e Å−3

Data collection: COLLECT (Bruker, 2008 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811048768/gk2434sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048768/gk2434Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811048768/gk2434Isup3.cml

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

C33H3F20N3O4	F(000) = 1736
Mr = 885.38	Dx = 1.907 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4030 reflections
a = 21.2370 (5) Å	θ = 0.4–28.3°
b = 6.3940 (1) Å	µ = 0.21 mm−1
c = 23.1045 (5) Å	T = 123 K
β = 100.585 (1)°	Block, colourless
V = 3083.96 (11) Å3	0.30 × 0.18 × 0.16 mm
Z = 4

Bruker–Nonius KappaCCD with an APEXII detector diffractometer	2526 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.039
graphite	θmax = 28.2°, θmin = 1.8°
Detector resolution: 9 pixels mm-1	h = −27→28
φ and ω scans	k = −8→8
7138 measured reflections	l = −30→30
3785 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0381P)2 + 7.2159P] where P = (Fo2 + 2Fc2)/3
3785 reflections	(Δ/σ)max < 0.001
366 parameters	Δρmax = 0.35 e Å−3
97 restraints	Δρmin = −0.42 e Å−3

Experimental. 13C NMR (CDCl3): δ (ppm) = 159.4, 149.1, 144.5, 142.4, 141.7, 138.7, 136.6, 123.8, 110.5.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	Occ. (<1)
F1	0.86727 (7)	0.9378 (2)	0.69841 (7)	0.0376 (4)
F2	0.78577 (10)	0.8370 (3)	0.59909 (7)	0.0616 (5)
F3	0.72661 (9)	0.4583 (3)	0.58930 (7)	0.0579 (5)
F4	0.75118 (6)	0.1782 (2)	0.67885 (7)	0.0362 (4)
F5	0.82680 (7)	0.2875 (2)	0.78079 (6)	0.0345 (4)
O1	0.87489 (9)	0.8475 (3)	0.82339 (8)	0.0380 (4)
N7	0.93905 (9)	0.5589 (3)	0.82488 (9)	0.0330 (5)
N1	1.0000	0.5463 (4)	0.7500	0.0278 (6)
C2	0.97130 (10)	0.4368 (4)	0.78664 (11)	0.0303 (5)
C3	0.97017 (12)	0.2207 (4)	0.78901 (14)	0.0392 (7)
H3	0.9496	0.1495	0.8165	0.047*
C4	1.0000	0.1126 (6)	0.7500	0.0450 (11)
H4	1.0000	−0.0360	0.7500	0.054*
C8	0.88798 (11)	0.6875 (4)	0.80002 (11)	0.0295 (5)
C9	0.84960 (10)	0.6158 (4)	0.74248 (10)	0.0253 (5)
C10	0.83779 (11)	0.7515 (4)	0.69504 (11)	0.0293 (5)
C11	0.79688 (13)	0.6999 (4)	0.64361 (11)	0.0373 (6)
C12	0.76727 (13)	0.5075 (4)	0.63878 (11)	0.0368 (6)
C13	0.77919 (11)	0.3668 (4)	0.68450 (11)	0.0294 (5)
C14	0.81941 (10)	0.4222 (4)	0.73576 (10)	0.0257 (5)
O2	1.02137 (19)	0.5421 (8)	0.9007 (2)	0.0851 (16)	0.773 (2)
C15	0.9663 (3)	0.5901 (8)	0.8850 (2)	0.0484 (16)	0.773 (2)
F6	0.96821 (11)	0.9929 (4)	0.93716 (10)	0.0545 (6)	0.773 (2)
F7	0.90327 (13)	1.0815 (4)	1.02541 (11)	0.0641 (8)	0.773 (2)
F8	0.82644 (14)	0.7899 (4)	1.06022 (10)	0.0548 (7)	0.773 (2)
F9	0.81043 (14)	0.4137 (4)	1.00624 (12)	0.0565 (7)	0.773 (2)
F10	0.87435 (13)	0.3237 (4)	0.91753 (12)	0.0533 (7)	0.773 (2)
C16	0.92394 (13)	0.6546 (4)	0.92708 (10)	0.0413 (10)	0.773 (2)
C17	0.93101 (11)	0.8490 (4)	0.95442 (11)	0.0429 (9)	0.773 (2)
C18	0.89756 (12)	0.8949 (3)	0.99922 (10)	0.0451 (9)	0.773 (2)
C19	0.85705 (12)	0.7464 (4)	1.01668 (10)	0.0432 (9)	0.773 (2)
C20	0.84999 (14)	0.5520 (4)	0.98934 (13)	0.0407 (11)	0.773 (2)
C21	0.88343 (15)	0.5061 (3)	0.94454 (13)	0.0381 (12)	0.773 (2)
O2B	1.0322 (5)	0.4514 (16)	0.8935 (5)	0.041 (3)	0.227 (2)
C15B	0.9785 (6)	0.524 (2)	0.8821 (5)	0.027 (4)	0.227 (2)
F6B	1.0454 (3)	0.7631 (12)	0.9763 (3)	0.048 (2)	0.227 (2)
F7B	0.9953 (4)	0.8597 (13)	1.0711 (3)	0.060 (2)	0.227 (2)
F8B	0.8734 (5)	0.7549 (14)	1.0761 (3)	0.059 (2)	0.227 (2)
F9B	0.8023 (5)	0.5329 (19)	0.9872 (4)	0.058 (3)	0.227 (2)
F10B	0.8522 (4)	0.4215 (13)	0.8935 (3)	0.0397 (18)	0.227 (2)
C16B	0.9465 (4)	0.6015 (14)	0.9305 (3)	0.029 (3)	0.227 (2)
C17B	0.9844 (3)	0.7046 (14)	0.9773 (3)	0.040 (2)	0.227 (2)
C18B	0.9591 (4)	0.7582 (14)	1.0267 (3)	0.043 (3)	0.227 (2)
C19B	0.8959 (4)	0.7086 (15)	1.0293 (3)	0.042 (3)	0.227 (2)
C20B	0.8581 (3)	0.6055 (17)	0.9825 (4)	0.034 (3)	0.227 (2)
C21B	0.8833 (4)	0.5519 (16)	0.9331 (4)	0.025 (3)	0.227 (2)

	U11	U22	U33	U12	U13	U23
F1	0.0398 (8)	0.0247 (7)	0.0498 (9)	−0.0086 (6)	0.0121 (7)	0.0033 (7)
F2	0.0912 (14)	0.0489 (11)	0.0402 (9)	−0.0188 (10)	0.0006 (9)	0.0136 (8)
F3	0.0692 (12)	0.0568 (12)	0.0403 (9)	−0.0210 (10)	−0.0093 (8)	−0.0015 (9)
F4	0.0296 (7)	0.0285 (8)	0.0512 (9)	−0.0101 (6)	0.0095 (6)	−0.0078 (7)
F5	0.0346 (7)	0.0277 (8)	0.0409 (8)	−0.0072 (6)	0.0062 (6)	0.0061 (6)
O1	0.0464 (11)	0.0271 (9)	0.0434 (10)	−0.0083 (8)	0.0159 (8)	−0.0102 (8)
N7	0.0269 (10)	0.0343 (12)	0.0373 (11)	−0.0054 (9)	0.0049 (9)	−0.0024 (10)
N1	0.0174 (12)	0.0214 (14)	0.0433 (17)	0.000	0.0021 (12)	0.000
C2	0.0179 (10)	0.0263 (12)	0.0447 (14)	−0.0012 (10)	0.0000 (10)	0.0012 (11)
C3	0.0236 (12)	0.0271 (13)	0.0656 (19)	−0.0033 (10)	0.0042 (12)	0.0084 (13)
C4	0.0240 (17)	0.0192 (17)	0.089 (3)	0.000	0.0020 (19)	0.000
C8	0.0276 (11)	0.0245 (12)	0.0386 (13)	−0.0081 (10)	0.0118 (10)	−0.0014 (11)
C9	0.0219 (10)	0.0237 (11)	0.0331 (12)	−0.0003 (9)	0.0118 (9)	−0.0031 (10)
C10	0.0304 (12)	0.0201 (11)	0.0400 (14)	−0.0056 (10)	0.0140 (11)	−0.0031 (11)
C11	0.0457 (15)	0.0356 (15)	0.0319 (13)	−0.0049 (12)	0.0105 (11)	0.0059 (12)
C12	0.0383 (14)	0.0381 (15)	0.0329 (13)	−0.0081 (12)	0.0033 (11)	−0.0051 (12)
C13	0.0256 (11)	0.0241 (12)	0.0408 (14)	−0.0059 (10)	0.0121 (10)	−0.0057 (11)
C14	0.0228 (10)	0.0230 (12)	0.0330 (12)	0.0016 (9)	0.0095 (9)	−0.0003 (10)
O2	0.040 (2)	0.106 (4)	0.094 (3)	0.032 (2)	−0.0279 (18)	−0.061 (3)
C15	0.035 (2)	0.041 (3)	0.062 (3)	0.009 (2)	−0.011 (2)	−0.026 (2)
F6	0.0586 (14)	0.0444 (14)	0.0607 (15)	−0.0048 (12)	0.0116 (12)	−0.0191 (12)
F7	0.0776 (17)	0.0436 (14)	0.0734 (17)	−0.0001 (13)	0.0204 (13)	−0.0319 (13)
F8	0.0691 (17)	0.0515 (15)	0.0451 (13)	0.0136 (13)	0.0142 (12)	−0.0149 (11)
F9	0.0761 (18)	0.0438 (16)	0.0508 (16)	0.0007 (15)	0.0151 (14)	−0.0041 (13)
F10	0.0680 (17)	0.0360 (14)	0.0561 (16)	0.0013 (12)	0.0117 (13)	−0.0186 (12)
C16	0.038 (2)	0.036 (2)	0.043 (2)	0.0126 (18)	−0.0102 (16)	−0.0140 (17)
C17	0.0409 (18)	0.0379 (19)	0.045 (2)	0.0075 (16)	−0.0048 (16)	−0.0116 (17)
C18	0.050 (2)	0.0365 (19)	0.044 (2)	0.0138 (17)	−0.0044 (16)	−0.0166 (17)
C19	0.047 (2)	0.044 (2)	0.0341 (18)	0.0151 (18)	−0.0019 (16)	−0.0082 (17)
C20	0.055 (3)	0.029 (2)	0.033 (2)	0.0114 (19)	−0.006 (2)	−0.0009 (18)
C21	0.048 (2)	0.023 (2)	0.037 (2)	0.0125 (17)	−0.0080 (18)	−0.0023 (18)
O2B	0.040 (5)	0.030 (5)	0.044 (5)	0.004 (4)	−0.016 (4)	0.017 (4)
C15B	0.030 (8)	0.027 (8)	0.024 (6)	−0.005 (6)	0.005 (5)	0.009 (6)
F6B	0.048 (4)	0.050 (5)	0.040 (4)	−0.003 (4)	−0.007 (3)	0.011 (4)
F7B	0.083 (6)	0.049 (5)	0.038 (4)	0.001 (5)	−0.012 (4)	−0.003 (4)
F8B	0.077 (6)	0.065 (6)	0.038 (4)	0.022 (5)	0.020 (4)	−0.007 (4)
F9B	0.067 (6)	0.076 (7)	0.036 (5)	−0.012 (6)	0.018 (4)	−0.005 (5)
F10B	0.055 (5)	0.038 (4)	0.025 (3)	−0.013 (4)	0.004 (3)	−0.006 (3)
C16B	0.042 (6)	0.023 (5)	0.020 (4)	0.001 (5)	0.002 (4)	0.000 (4)
C17B	0.053 (6)	0.031 (5)	0.032 (5)	−0.001 (5)	0.000 (4)	0.003 (4)
C18B	0.060 (6)	0.039 (5)	0.027 (5)	0.007 (5)	−0.001 (5)	−0.002 (4)
C19B	0.059 (6)	0.045 (6)	0.024 (5)	0.006 (5)	0.015 (5)	−0.001 (4)
C20B	0.046 (6)	0.021 (5)	0.037 (5)	0.005 (5)	0.009 (5)	0.014 (5)
C21B	0.044 (6)	0.009 (4)	0.020 (5)	0.003 (4)	0.001 (4)	0.002 (4)

F1—C10	1.341 (3)	C15—C16	1.498 (6)
F2—C11	1.339 (3)	F6—C17	1.321 (3)
F3—C12	1.338 (3)	F7—C18	1.333 (3)
F4—C13	1.340 (3)	F8—C19	1.324 (3)
F5—C14	1.338 (3)	F9—C20	1.327 (4)
O1—C8	1.213 (3)	F10—C21	1.320 (3)
N7—C8	1.398 (3)	C16—C17	1.3900
N7—C15	1.417 (6)	C16—C21	1.3900
N7—C2	1.443 (3)	C17—C18	1.3900
N7—C15B	1.446 (12)	C18—C19	1.3900
N1—C2i	1.330 (3)	C19—C20	1.3900
N1—C2	1.330 (3)	C20—C21	1.3900
C2—C3	1.383 (4)	O2B—C15B	1.215 (14)
C3—C4	1.379 (3)	C15B—C16B	1.497 (13)
C3—H3	0.9500	F6B—C17B	1.353 (9)
C4—C3i	1.379 (3)	F7B—C18B	1.332 (10)
C4—H4	0.9500	F8B—C19B	1.294 (9)
C8—C9	1.498 (3)	F9B—C20B	1.294 (12)
C9—C10	1.384 (3)	F10B—C21B	1.321 (9)
C9—C14	1.389 (3)	C16B—C17B	1.3900
C10—C11	1.377 (4)	C16B—C21B	1.3900
C11—C12	1.377 (4)	C17B—C18B	1.3900
C12—C13	1.375 (4)	C18B—C19B	1.3900
C13—C14	1.374 (3)	C19B—C20B	1.3900
O2—C15	1.200 (6)	C20B—C21B	1.3900
C8—N7—C15	117.8 (3)	C17—C16—C21	120.0
C8—N7—C2	119.1 (2)	C17—C16—C15	120.9 (3)
C15—N7—C2	121.5 (3)	C21—C16—C15	118.5 (3)
C8—N7—C15B	138.0 (6)	F6—C17—C16	120.4 (2)
C2—N7—C15B	102.4 (6)	F6—C17—C18	119.6 (2)
C2i—N1—C2	116.5 (3)	C16—C17—C18	120.0
N1—C2—C3	124.4 (3)	F7—C18—C19	119.3 (2)
N1—C2—N7	115.5 (2)	F7—C18—C17	120.7 (2)
C3—C2—N7	120.2 (2)	C19—C18—C17	120.0
C4—C3—C2	117.5 (3)	F8—C19—C18	119.6 (2)
C4—C3—H3	121.3	F8—C19—C20	120.4 (2)
C2—C3—H3	121.3	C18—C19—C20	120.0
C3—C4—C3i	119.8 (4)	F9—C20—C21	121.1 (2)
C3—C4—H4	120.1	F9—C20—C19	118.9 (2)
C3i—C4—H4	120.1	C21—C20—C19	120.0
O1—C8—N7	122.5 (2)	F10—C21—C20	119.2 (2)
O1—C8—C9	121.4 (2)	F10—C21—C16	120.7 (2)
N7—C8—C9	116.1 (2)	C20—C21—C16	120.0
C10—C9—C14	117.2 (2)	O2B—C15B—N7	128.4 (11)
C10—C9—C8	120.1 (2)	O2B—C15B—C16B	120.1 (11)
C14—C9—C8	122.4 (2)	N7—C15B—C16B	111.4 (9)
F1—C10—C11	118.5 (2)	C17B—C16B—C21B	120.0
F1—C10—C9	119.7 (2)	C17B—C16B—C15B	117.5 (7)
C11—C10—C9	121.8 (2)	C21B—C16B—C15B	122.0 (7)
F2—C11—C12	120.6 (2)	F6B—C17B—C18B	117.5 (6)
F2—C11—C10	120.0 (2)	F6B—C17B—C16B	122.5 (6)
C12—C11—C10	119.4 (2)	C18B—C17B—C16B	120.0
F3—C12—C13	120.1 (2)	F7B—C18B—C17B	119.8 (7)
F3—C12—C11	119.5 (2)	F7B—C18B—C19B	120.2 (7)
C13—C12—C11	120.4 (2)	C17B—C18B—C19B	120.0
F4—C13—C14	120.7 (2)	F8B—C19B—C20B	120.6 (8)
F4—C13—C12	119.9 (2)	F8B—C19B—C18B	119.4 (8)
C14—C13—C12	119.4 (2)	C20B—C19B—C18B	120.0
F5—C14—C13	118.0 (2)	F9B—C20B—C19B	120.8 (8)
F5—C14—C9	120.1 (2)	F9B—C20B—C21B	118.5 (8)
C13—C14—C9	121.8 (2)	C19B—C20B—C21B	120.0
O2—C15—N7	117.4 (5)	F10B—C21B—C20B	120.3 (7)
O2—C15—C16	122.8 (5)	F10B—C21B—C16B	118.6 (7)
N7—C15—C16	119.3 (4)	C20B—C21B—C16B	120.0
C2i—N1—C2—C3	0.57 (19)	C21—C16—C17—C18	0.0
C2i—N1—C2—N7	−178.4 (2)	C15—C16—C17—C18	−171.1 (3)
C8—N7—C2—N1	62.2 (3)	F6—C17—C18—F7	−0.9 (3)
C15—N7—C2—N1	−103.0 (4)	C16—C17—C18—F7	−179.2 (3)
C15B—N7—C2—N1	−111.0 (6)	F6—C17—C18—C19	178.4 (3)
C8—N7—C2—C3	−116.9 (3)	C16—C17—C18—C19	0.0
C15—N7—C2—C3	78.0 (4)	F7—C18—C19—F8	−2.2 (3)
C15B—N7—C2—C3	70.0 (6)	C17—C18—C19—F8	178.6 (3)
N1—C2—C3—C4	−1.1 (4)	F7—C18—C19—C20	179.3 (3)
N7—C2—C3—C4	177.85 (18)	C17—C18—C19—C20	0.0
C2—C3—C4—C3i	0.50 (17)	F8—C19—C20—F9	2.3 (3)
C15—N7—C8—O1	15.2 (4)	C18—C19—C20—F9	−179.1 (3)
C2—N7—C8—O1	−150.5 (2)	F8—C19—C20—C21	−178.6 (3)
C15B—N7—C8—O1	19.5 (9)	C18—C19—C20—C21	0.0
C15—N7—C8—C9	−164.5 (3)	F9—C20—C21—F10	1.7 (3)
C2—N7—C8—C9	29.8 (3)	C19—C20—C21—F10	−177.5 (3)
C15B—N7—C8—C9	−160.2 (8)	F9—C20—C21—C16	179.1 (3)
O1—C8—C9—C10	51.4 (3)	C19—C20—C21—C16	0.0
N7—C8—C9—C10	−128.9 (2)	C17—C16—C21—F10	177.4 (3)
O1—C8—C9—C14	−122.1 (3)	C15—C16—C21—F10	−11.2 (4)
N7—C8—C9—C14	57.6 (3)	C17—C16—C21—C20	0.0
C14—C9—C10—F1	−177.86 (19)	C15—C16—C21—C20	171.3 (3)
C8—C9—C10—F1	8.3 (3)	C8—N7—C15B—O2B	−155.9 (9)
C14—C9—C10—C11	1.3 (4)	C2—N7—C15B—O2B	15.1 (14)
C8—C9—C10—C11	−172.6 (2)	C8—N7—C15B—C16B	20.5 (14)
F1—C10—C11—F2	−2.1 (4)	C2—N7—C15B—C16B	−168.5 (7)
C9—C10—C11—F2	178.8 (2)	O2B—C15B—C16B—C17B	37.7 (14)
F1—C10—C11—C12	178.5 (2)	N7—C15B—C16B—C17B	−139.0 (8)
C9—C10—C11—C12	−0.6 (4)	O2B—C15B—C16B—C21B	−134.5 (10)
F2—C11—C12—F3	−0.6 (4)	N7—C15B—C16B—C21B	48.8 (11)
C10—C11—C12—F3	178.8 (3)	C21B—C16B—C17B—F6B	−177.6 (9)
F2—C11—C12—C13	179.6 (2)	C15B—C16B—C17B—F6B	10.0 (10)
C10—C11—C12—C13	−1.1 (4)	C21B—C16B—C17B—C18B	0.0
F3—C12—C13—F4	1.6 (4)	C15B—C16B—C17B—C18B	−172.3 (9)
C11—C12—C13—F4	−178.6 (2)	F6B—C17B—C18B—F7B	−1.2 (9)
F3—C12—C13—C14	−177.9 (2)	C16B—C17B—C18B—F7B	−179.0 (9)
C11—C12—C13—C14	2.0 (4)	F6B—C17B—C18B—C19B	177.8 (9)
F4—C13—C14—F5	−3.7 (3)	C16B—C17B—C18B—C19B	0.0
C12—C13—C14—F5	175.7 (2)	F7B—C18B—C19B—F8B	−2.6 (11)
F4—C13—C14—C9	179.26 (19)	C17B—C18B—C19B—F8B	178.4 (10)
C12—C13—C14—C9	−1.3 (4)	F7B—C18B—C19B—C20B	179.0 (9)
C10—C9—C14—F5	−177.3 (2)	C17B—C18B—C19B—C20B	0.0
C8—C9—C14—F5	−3.6 (3)	F8B—C19B—C20B—F9B	−7.9 (12)
C10—C9—C14—C13	−0.3 (3)	C18B—C19B—C20B—F9B	170.5 (12)
C8—C9—C14—C13	173.4 (2)	F8B—C19B—C20B—C21B	−178.4 (10)
C8—N7—C15—O2	−153.1 (5)	C18B—C19B—C20B—C21B	0.0
C2—N7—C15—O2	12.2 (7)	F9B—C20B—C21B—F10B	−3.3 (10)
C8—N7—C15—C16	34.5 (6)	C19B—C20B—C21B—F10B	167.5 (10)
C2—N7—C15—C16	−160.2 (3)	F9B—C20B—C21B—C16B	−170.7 (11)
O2—C15—C16—C17	73.5 (6)	C19B—C20B—C21B—C16B	0.0
N7—C15—C16—C17	−114.5 (4)	C17B—C16B—C21B—F10B	−167.7 (10)
O2—C15—C16—C21	−97.7 (6)	C15B—C16B—C21B—F10B	4.3 (11)
N7—C15—C16—C21	74.2 (5)	C17B—C16B—C21B—C20B	0.0
C21—C16—C17—F6	−178.4 (3)	C15B—C16B—C21B—C20B	172.0 (9)
C15—C16—C17—F6	10.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N1ii	0.95	2.67	3.621 (5)	180
C3—H3···O1ii	0.95	2.52	3.318 (3)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯N1i	0.95	2.67	3.621 (5)	180
C3—H3⋯O1i	0.95	2.52	3.318 (3)	141

Symmetry code: (i) .