2-(2-Aza­bicyclo­[3.2.1]octa-3,6-dien-2-yl)-1,3-di­meth­oxy­imidazolium hexa­fluorido­phosphate

Haslinger, S.; Laus, G.; Wurst, K.; Schottenberger, H.

doi:10.1107/S2414314616014103

organic compounds

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ISSN: 2414-3146

Volume 1| Part 9| September 2016| x161410

doi:10.1107/S2414314616014103

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2-(2-Azabicyclo[3.2.1]octa-3,6-dien-2-yl)-1,3-dimethoxyimidazolium hexafluoridophosphate

Simone Haslinger,^a Gerhard Laus,^a ^* Klaus Wurst ^a and Herwig Schottenberger ^a

^aUniversity of Innsbruck, Faculty of Chemistry and Pharmacy, Innrain 80, 6020 Innsbruck, Austria
^*Correspondence e-mail: gerhard.laus@uibk.ac.at

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 1 September 2016; accepted 5 September 2016; online 9 September 2016)

The title salt, C₁₂H₁₆N₃O₂⁺·PF₆⁻, was obtained by the dipolar cycloaddition of norbornadiene to 2-azido-1,3-dimethoxyimidazolium hexafluoridophosphate. The methoxy groups attached to the imidazolium ring of the cation adopt an anti conformation [displacements of the C atoms from the ring plane = 1.386 (4) and −1.404 (3) Å]. In the crystal, weak inter-ionic C—H⋯F contacts are observed. The structure was refined as a two-component twin. Positional disorder of the fluorine atoms of the PF₆ anion was observed, the occupancy ratio being 0.562 (16):0.438 (16).

Keywords: azide; cycloaddition; imidazole; norbornadiene; crystal structure.

CCDC reference: 1502503

Structure description

The 1,3-dipolar cycloaddition of strained alkenes such as norbornene or norbornadiene to azidoazolium salts with concomitant loss of dinitrogen affords tricyclic aziridines or bicyclic azaoctadienes, respectively (Laus, Kahlenberg et al., 2016 ; Laus, Kostner et al., 2016 ). Thus, the title compound was obtained from bicyclo[2.2.1]hepta-2,5-diene (norbornadiene) and 2-azido-1,3-dimethoxyimidazolium hexafluoridophosphate.

Conformational syn/anti isomerism in related 1,3-di(alkyloxy)imidazolium salts has been noticed previously (Laus et al., 2007 ; Laus, Kahlenberg et al., 2010 ; Laus, Wurst et al., 2010 ; Froschauer et al., 2013 ; Rietzler et al., 2015 ; Partl et al., 2016 ). Here, the methoxy groups of the norbornadiene adduct adopt an anti conformation (Fig. 1). The C4 atom is displaced from the ring plane by 1.386 (4), and C5 by −1.404 (3) Å. A C4—O1⋯O2—C5 pseudo dihedral angle of 168.4 (3)° is found.

Figure 1
The molecular structure of the cation of the title compound, showing 50% probability displacement ellipsoids. The anion is not shown.

There are no directional classical hydrogen bonds in this structure. At the most, weak C—H⋯F interactions (H2⋯F5 = 2.36, H3⋯F6 = 2.42 and H5A⋯F5 = 2.53 Å) shorter than the sum of van der Waals radii between the imidazole H atoms and negatively polarized F atoms are worth mentioning (Table 1; Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯F5ⁱ	0.95	2.36	3.242 (12)	154
C2—H2⋯F5Aⁱ	0.95	2.36	3.23 (2)	153
C3—H3⋯F6	0.95	2.42	3.365 (11)	171
C4—H4A⋯F6Aⁱⁱ	0.98	2.49	3.21 (2)	131
C4—H4B⋯F2Aⁱⁱⁱ	0.98	2.51	3.383 (17)	148
C5—H5A⋯F5^iv	0.98	2.53	3.134 (11)	120
C5—H5A⋯F5A^iv	0.98	2.34	3.02 (2)	125
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+1, -z+1; (iii) -x+2, -y+1, -z+1; (iv) -x+3, -y, -z+1.

Figure 2
Crystal packing of the title compound. The C—H⋯F interactions are shown as dashed lines.

Synthesis and crystallization

A solution of 2-azido-1,3-dimethoxyimidazolium hexafluoridophosphate (0.38 g, 1.2 mmol; Laus et al., 2007) and norbornadiene (0.13 g, 1.4 mmol) in acetone (20 ml) was stirred for 18 h at room temperature. The volatiles were removed under reduced pressure, and the residue was crystallized from H₂O/acetone. ¹H NMR (300 MHz, DMSO-d₆): δ 1.86 (d, J = 10.6 Hz, 1H), 2.00 (m, 1H), 2.87 (m, 1H), 4.12 (s, 6H), 4.76 (s, 1H), 5.40 (td, J = 6.4, 1.3 Hz, 1H), 5.68 (dd, J = 2.3, 5.5 Hz, 1H), 6.06 (dd, J = 0.9, 7.7 Hz, 1H), 6.41 (dd, J = 2.7, 5.4 Hz, 1H), 8.00 (s, 2H) p.p.m. ¹³C NMR (75 MHz, DMSO-d₆): δ 35.2, 36.2, 63.8, 68.0 (2 C), 109.6, 112.4 (2 C), 121.2, 122.4, 134.8, 139.4 p.p.m. IR (neat): ν 3173, 3151, 1627, 1614, 827 cm⁻¹.

Refinement

The structure was refined as a two-component twin with non-merohedral twinning by 180 degrees about the reciprocal axis 0 0 1. In addition, positional disorder of the fluorine atoms of the PF₆ anion was observed; the occupancy ratio of 0.562 (16):0.438 (16) for the two orientations was obtained by refinement with a free variable. Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₂H₁₆N₃O₂⁺·PF₆⁻
M_r	379.25
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	173
a, b, c (Å)	7.4207 (6), 8.8159 (7), 12.5246 (10)
α, β, γ (°)	86.873 (3), 87.735 (3), 77.166 (3)
V (Å³)	797.39 (11)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.25
Crystal size (mm)	0.18 × 0.17 × 0.09

Data collection
Diffractometer	Bruker D8 QUEST PHOTON 100
Absorption correction	Multi-scan (DIFABS; Bruker, 2014 )
T_min, T_max	0.792, 0.862
No. of measured, independent and observed [I > 2σ(I)] reflections	2774, 2774, 2501
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.124, 1.12
No. of reflections	2774
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.31
Computer programs: APEX2 (Bruker, 2014), SAINT (Bruker, 2014), SHELXS2014/7 (Sheldrick, 2008 ), SHELXL2014/7 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ), Mercury (Macrae et al., 2006 ).

Structural data

CCDC reference: 1502503

Crystal structure: contains datablock I. DOI: 10.1107/S2414314616014103/hb4076sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616014103/hb4076Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616014103/hb4076Isup3.mol

Supporting information file. DOI: 10.1107/S2414314616014103/hb4076Isup4.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS2014/7 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: Mercury (Macrae et al., 2006).

2-(2-Azabicyclo[3.2.1]octa-3,6-dien-2-yl)-1,3-dimethoxyimidazolium hexafluoridophosphate top

Crystal data top

C₁₂H₁₆N₃O₂⁺·PF₆⁻	Z = 2
M_r = 379.25	F(000) = 388
Triclinic, P1	D_x = 1.580 Mg m⁻³
a = 7.4207 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.8159 (7) Å	Cell parameters from 4024 reflections
c = 12.5246 (10) Å	θ = 2.8–25.3°
α = 86.873 (3)°	µ = 0.25 mm⁻¹
β = 87.735 (3)°	T = 173 K
γ = 77.166 (3)°	Prism, brown
V = 797.39 (11) Å³	0.18 × 0.17 × 0.09 mm

Data collection top

Bruker D8 QUEST PHOTON 100 diffractometer	2774 measured reflections
Radiation source: Incoatec Microfocus	2774 independent reflections
Multi layered optics monochromator	2501 reflections with I > 2σ(I)
Detector resolution: 10.4 pixels mm^-1	θ_max = 25.0°, θ_min = 2.4°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (DIFABS; Bruker, 2014)	k = −10→10
T_min = 0.792, T_max = 0.862	l = 0→14

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.054	H-atom parameters constrained
wR(F²) = 0.124	w = 1/[σ²(F_o²) + (0.031P)² + 0.897P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max < 0.001
2774 reflections	Δρ_max = 0.40 e Å⁻³
273 parameters	Δρ_min = −0.31 e Å⁻³

Special details top

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. Refined as a 2-component twin with non-merohedral twinning by 180 degrees about the reciprocal axis 0 0 1. Programs like "cell_now" and "twinabs" (Bruker) were used for cell search of twin components and absorption correction. Positional disorder of the fluorine atoms of PF6; ratio of 56:44 was obtained by using refinement with free variable.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.4239 (4)	0.2863 (3)	0.7117 (3)	0.0505 (8)
O2	1.0715 (3)	0.2143 (3)	0.6834 (3)	0.0429 (7)
N1	0.6012 (4)	0.2657 (4)	0.6683 (3)	0.0417 (8)
N2	0.8907 (4)	0.2373 (4)	0.6560 (3)	0.0367 (8)
N3	0.7628 (4)	0.2455 (4)	0.8350 (2)	0.0372 (8)
C1	0.7505 (6)	0.2487 (5)	0.7279 (3)	0.0335 (8)
C2	0.6461 (7)	0.2612 (5)	0.5602 (4)	0.0513 (11)
H2	0.5639	0.2666	0.5032	0.062*
C3	0.8300 (7)	0.2476 (5)	0.5526 (3)	0.0470 (11)
H3	0.9036	0.2454	0.4887	0.056*
C4	0.3311 (7)	0.4469 (5)	0.6979 (5)	0.0724 (16)
H4A	0.2053	0.4614	0.7287	0.109*
H4B	0.3989	0.5117	0.7342	0.109*
H4C	0.3256	0.4774	0.6215	0.109*
C5	1.1633 (6)	0.0519 (4)	0.6758 (4)	0.0513 (11)
H5A	1.2927	0.0374	0.6957	0.077*
H5B	1.1011	−0.0124	0.7244	0.077*
H5C	1.1583	0.0208	0.6022	0.077*
C6	0.6429 (6)	0.1744 (5)	0.9028 (3)	0.0462 (10)
H6	0.5642	0.1171	0.8733	0.055*
C7	0.6429 (8)	0.1896 (6)	1.0083 (4)	0.0650 (14)
H7	0.5667	0.1398	1.0544	0.078*
C8	0.7627 (11)	0.2851 (7)	1.0546 (4)	0.0775 (17)
H8	0.7280	0.3147	1.1298	0.093*
C9	0.9570 (10)	0.1996 (7)	1.0392 (5)	0.0832 (19)
H9	1.0245	0.1315	1.0923	0.100*
C10	1.0243 (8)	0.2281 (6)	0.9454 (5)	0.0685 (15)
H10	1.1462	0.1852	0.9198	0.082*
C11	0.8821 (6)	0.3375 (5)	0.8847 (3)	0.0428 (10)
H11	0.9348	0.4058	0.8315	0.051*
C12	0.7620 (8)	0.4288 (6)	0.9721 (4)	0.0673 (15)
H12A	0.6363	0.4779	0.9477	0.081*
H12B	0.8201	0.5082	1.0009	0.081*
P1	1.26751 (15)	0.24411 (11)	0.32028 (8)	0.0327 (2)
F1	1.2604 (10)	0.1998 (16)	0.4404 (5)	0.095 (5)	0.562 (16)
F2	1.2768 (14)	0.2929 (17)	0.1975 (5)	0.104 (4)	0.562 (16)
F3	1.2520 (13)	0.4160 (9)	0.3478 (14)	0.115 (5)	0.562 (16)
F4	1.285 (2)	0.0749 (9)	0.2887 (15)	0.137 (7)	0.562 (16)
F5	1.4859 (13)	0.2220 (13)	0.3286 (9)	0.068 (3)	0.562 (16)
F6	1.0517 (15)	0.2681 (14)	0.3144 (8)	0.066 (3)	0.562 (16)
F1A	1.201 (3)	0.1183 (18)	0.387 (2)	0.205 (11)	0.438 (16)
F2A	1.315 (2)	0.382 (2)	0.258 (2)	0.159 (9)	0.438 (16)
F3A	1.232 (2)	0.341 (2)	0.4227 (13)	0.134 (7)	0.438 (16)
F4A	1.305 (2)	0.139 (3)	0.2291 (15)	0.149 (9)	0.438 (16)
F5A	1.470 (2)	0.177 (3)	0.345 (2)	0.184 (11)	0.438 (16)
F6A	1.067 (2)	0.318 (3)	0.2936 (18)	0.135 (8)	0.438 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0267 (15)	0.0486 (17)	0.078 (2)	−0.0131 (13)	−0.0037 (14)	0.0034 (15)
O2	0.0269 (13)	0.0386 (14)	0.0639 (19)	−0.0073 (11)	0.0018 (14)	−0.0100 (15)
N1	0.0323 (17)	0.0449 (18)	0.051 (2)	−0.0143 (14)	−0.0047 (17)	−0.0025 (17)
N2	0.0301 (17)	0.0390 (17)	0.042 (2)	−0.0095 (13)	0.0010 (14)	−0.0058 (14)
N3	0.0345 (19)	0.0411 (19)	0.0392 (17)	−0.0147 (14)	0.0014 (14)	−0.0049 (15)
C1	0.0320 (19)	0.0313 (19)	0.0403 (19)	−0.0141 (15)	−0.0001 (18)	−0.0009 (17)
C2	0.060 (3)	0.055 (3)	0.042 (3)	−0.017 (2)	−0.016 (2)	−0.005 (2)
C3	0.060 (3)	0.047 (2)	0.037 (2)	−0.017 (2)	−0.001 (2)	−0.0073 (19)
C4	0.047 (3)	0.050 (3)	0.121 (5)	−0.011 (2)	0.010 (3)	−0.017 (3)
C5	0.044 (2)	0.035 (2)	0.072 (3)	−0.0010 (17)	−0.001 (2)	−0.010 (2)
C6	0.047 (2)	0.047 (2)	0.047 (3)	−0.017 (2)	0.009 (2)	−0.003 (2)
C7	0.087 (4)	0.055 (3)	0.057 (3)	−0.029 (3)	0.021 (3)	−0.006 (2)
C8	0.120 (5)	0.078 (4)	0.045 (3)	−0.041 (4)	0.012 (4)	−0.023 (3)
C9	0.124 (6)	0.079 (4)	0.058 (4)	−0.044 (4)	−0.029 (4)	0.002 (3)
C10	0.077 (4)	0.059 (3)	0.077 (4)	−0.025 (3)	−0.030 (3)	−0.005 (3)
C11	0.048 (2)	0.039 (2)	0.046 (2)	−0.0162 (18)	0.0029 (19)	−0.0122 (18)
C12	0.093 (4)	0.059 (3)	0.055 (3)	−0.025 (3)	0.014 (3)	−0.024 (3)
P1	0.0377 (5)	0.0274 (4)	0.0329 (5)	−0.0070 (3)	−0.0026 (5)	−0.0024 (5)
F1	0.080 (5)	0.183 (13)	0.025 (3)	−0.041 (6)	−0.002 (3)	0.031 (5)
F2	0.110 (6)	0.161 (12)	0.034 (3)	−0.025 (6)	0.000 (4)	0.028 (5)
F3	0.099 (6)	0.040 (4)	0.210 (15)	−0.021 (4)	0.032 (8)	−0.048 (6)
F4	0.138 (8)	0.028 (4)	0.252 (19)	−0.028 (4)	0.020 (11)	−0.052 (6)
F5	0.040 (4)	0.099 (6)	0.068 (5)	−0.024 (5)	0.001 (3)	−0.010 (4)
F6	0.044 (4)	0.099 (7)	0.064 (4)	−0.028 (4)	0.005 (3)	−0.028 (5)
F1A	0.31 (3)	0.088 (9)	0.22 (2)	−0.074 (12)	0.124 (19)	0.038 (11)
F2A	0.155 (13)	0.109 (12)	0.22 (2)	−0.067 (10)	−0.010 (13)	0.107 (14)
F3A	0.165 (12)	0.127 (15)	0.110 (12)	−0.009 (10)	0.000 (9)	−0.101 (11)
F4A	0.136 (11)	0.19 (2)	0.117 (13)	−0.003 (14)	−0.002 (10)	−0.141 (14)
F5A	0.098 (12)	0.169 (16)	0.24 (2)	0.101 (11)	−0.103 (13)	−0.121 (14)
F6A	0.047 (8)	0.133 (14)	0.208 (17)	0.017 (8)	−0.059 (9)	0.014 (11)

Geometric parameters (Å, º) top

O1—N1	1.380 (4)	C8—C9	1.481 (9)
O1—C4	1.435 (5)	C8—C12	1.590 (8)
O2—N2	1.366 (4)	C8—H8	1.0000
O2—C5	1.449 (4)	C9—C10	1.293 (9)
N1—C1	1.336 (5)	C9—H9	0.9500
N1—C2	1.382 (6)	C10—C11	1.467 (7)
N2—C1	1.339 (5)	C10—H10	0.9500
N2—C3	1.379 (5)	C11—C12	1.529 (6)
N3—C1	1.347 (5)	C11—H11	1.0000
N3—C6	1.426 (5)	C12—H12A	0.9900
N3—C11	1.499 (5)	C12—H12B	0.9900
C2—C3	1.343 (6)	P1—F4A	1.489 (9)
C2—H2	0.9500	P1—F2A	1.504 (9)
C3—H3	0.9500	P1—F1A	1.511 (10)
C4—H4A	0.9800	P1—F5A	1.523 (15)
C4—H4B	0.9800	P1—F6A	1.528 (15)
C4—H4C	0.9800	P1—F1	1.535 (5)
C5—H5A	0.9800	P1—F4	1.540 (7)
C5—H5B	0.9800	P1—F3	1.550 (7)
C5—H5C	0.9800	P1—F3A	1.562 (9)
C6—C7	1.335 (6)	P1—F6	1.572 (11)
C6—H6	0.9500	P1—F2	1.577 (6)
C7—C8	1.504 (8)	P1—F5	1.596 (9)
C7—H7	0.9500

N1—O1—C4	109.6 (3)	C8—C9—H9	123.8
N2—O2—C5	110.5 (3)	C9—C10—C11	109.0 (6)
C1—N1—O1	123.0 (4)	C9—C10—H10	125.5
C1—N1—C2	112.1 (4)	C11—C10—H10	125.5
O1—N1—C2	124.9 (4)	C10—C11—N3	108.0 (4)
C1—N2—O2	123.3 (3)	C10—C11—C12	103.2 (4)
C1—N2—C3	111.7 (3)	N3—C11—C12	106.1 (4)
O2—N2—C3	124.9 (3)	C10—C11—H11	113.0
C1—N3—C6	120.6 (3)	N3—C11—H11	113.0
C1—N3—C11	120.1 (3)	C12—C11—H11	113.0
C6—N3—C11	118.7 (3)	C11—C12—C8	96.9 (4)
N1—C1—N2	104.0 (3)	C11—C12—H12A	112.4
N1—C1—N3	129.5 (4)	C8—C12—H12A	112.4
N2—C1—N3	126.5 (4)	C11—C12—H12B	112.4
C3—C2—N1	105.7 (4)	C8—C12—H12B	112.4
C3—C2—H2	127.2	H12A—C12—H12B	109.9
N1—C2—H2	127.2	F4A—P1—F2A	95.0 (11)
C2—C3—N2	106.4 (4)	F4A—P1—F1A	89.4 (11)
C2—C3—H3	126.8	F2A—P1—F1A	173.8 (11)
N2—C3—H3	126.8	F4A—P1—F5A	84.3 (10)
O1—C4—H4A	109.5	F2A—P1—F5A	91.4 (12)
O1—C4—H4B	109.5	F1A—P1—F5A	93.4 (13)
H4A—C4—H4B	109.5	F4A—P1—F6A	96.4 (10)
O1—C4—H4C	109.5	F2A—P1—F6A	85.9 (10)
H4A—C4—H4C	109.5	F1A—P1—F6A	89.3 (11)
H4B—C4—H4C	109.5	F5A—P1—F6A	177.3 (12)
O2—C5—H5A	109.5	F1—P1—F4	92.9 (7)
O2—C5—H5B	109.5	F1—P1—F3	89.2 (7)
H5A—C5—H5B	109.5	F4—P1—F3	177.9 (8)
O2—C5—H5C	109.5	F4A—P1—F3A	174.9 (11)
H5A—C5—H5C	109.5	F2A—P1—F3A	89.6 (11)
H5B—C5—H5C	109.5	F1A—P1—F3A	86.2 (9)
C7—C6—N3	119.1 (4)	F5A—P1—F3A	93.4 (10)
C7—C6—H6	120.4	F6A—P1—F3A	86.1 (10)
N3—C6—H6	120.4	F1—P1—F6	91.1 (5)
C6—C7—C8	120.4 (4)	F4—P1—F6	88.4 (7)
C6—C7—H7	119.8	F3—P1—F6	92.1 (5)
C8—C7—H7	119.8	F1—P1—F2	178.7 (7)
C9—C8—C7	107.0 (5)	F4—P1—F2	88.3 (7)
C9—C8—C12	99.4 (5)	F3—P1—F2	89.6 (7)
C7—C8—C12	106.2 (4)	F6—P1—F2	89.5 (5)
C9—C8—H8	114.3	F1—P1—F5	88.0 (5)
C7—C8—H8	114.3	F4—P1—F5	92.6 (7)
C12—C8—H8	114.3	F3—P1—F5	87.0 (5)
C10—C9—C8	112.4 (6)	F6—P1—F5	178.7 (5)
C10—C9—H9	123.8	F2—P1—F5	91.3 (5)

C4—O1—N1—C1	103.4 (5)	O2—N2—C3—C2	176.5 (3)
C4—O1—N1—C2	−76.1 (5)	C1—N3—C6—C7	−171.9 (5)
C5—O2—N2—C1	99.9 (4)	C11—N3—C6—C7	−1.1 (7)
C5—O2—N2—C3	−78.3 (5)	N3—C6—C7—C8	2.1 (8)
O1—N1—C1—N2	−178.0 (3)	C6—C7—C8—C9	−69.0 (7)
C2—N1—C1—N2	1.6 (5)	C6—C7—C8—C12	36.5 (7)
O1—N1—C1—N3	1.0 (7)	C7—C8—C9—C10	84.2 (6)
C2—N1—C1—N3	−179.4 (4)	C12—C8—C9—C10	−26.1 (6)
O2—N2—C1—N1	−178.2 (3)	C8—C9—C10—C11	−0.1 (7)
C3—N2—C1—N1	0.2 (5)	C9—C10—C11—N3	−84.2 (5)
O2—N2—C1—N3	2.7 (6)	C9—C10—C11—C12	27.8 (5)
C3—N2—C1—N3	−178.9 (4)	C1—N3—C11—C10	−119.4 (5)
C6—N3—C1—N1	36.2 (6)	C6—N3—C11—C10	69.8 (5)
C11—N3—C1—N1	−134.4 (4)	C1—N3—C11—C12	130.6 (4)
C6—N3—C1—N2	−144.9 (4)	C6—N3—C11—C12	−40.2 (5)
C11—N3—C1—N2	44.4 (6)	C10—C11—C12—C8	−40.5 (5)
C1—N1—C2—C3	−2.7 (5)	N3—C11—C12—C8	72.9 (5)
O1—N1—C2—C3	176.9 (3)	C9—C8—C12—C11	39.0 (5)
N1—C2—C3—N2	2.6 (4)	C7—C8—C12—C11	−71.9 (5)
C1—N2—C3—C2	−1.8 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···F5ⁱ	0.95	2.36	3.242 (12)	154
C2—H2···F5Aⁱ	0.95	2.36	3.23 (2)	153
C3—H3···F6	0.95	2.42	3.365 (11)	171
C4—H4A···F6Aⁱⁱ	0.98	2.49	3.21 (2)	131
C4—H4B···F2Aⁱⁱⁱ	0.98	2.51	3.383 (17)	148
C5—H5A···F5^iv	0.98	2.53	3.134 (11)	120
C5—H5A···F5A^iv	0.98	2.34	3.02 (2)	125

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+1; (iii) −x+2, −y+1, −z+1; (iv) −x+3, −y, −z+1.

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