5-(4-Fluoro-phen-yl)-2H-pyrazol-1-ium 2,2,2-tri-fluoro-acetate.

The title salt, C9H8FN2 (+)·C2F3O2 (-), crystallizes with two independent cations (A and B) and two independent anions (C and D) in the asymmetric unit. In the cations, the dihedral angles between the benzene and pyrazolium rings are 23.7 (3)° in cation A and 1.8 (8)° in cation B. In the crystal, each anion links to the two cations via N-H⋯O hydrogen bonds, forming a U-shaped unit with an R 4 (4)(14) ring motif. These U-shaped units stack along the a axis and are linked via C-H⋯O and C-H⋯F hydrogen bonds, forming slabs lying parallel to (100). Within the slabs there are π-π inter-actions between the pyrazolium rings [inter-centroid distance = 3.6326 (15) Å] and between the benzene rings [inter-centroid distance = 3.7244 (16) Å]. In the anions, the F atoms of the tri-fluoro-methyl groups are disordered over two sets of sites, with refined occupancy ratios of 0.58 (3):0.42, 0.540 (14):0.46 (14), and 0.55 (2):0.45 (2) for anion C, and 0.73 (5):0.27 (5), 0.63 (5):0.37 (5), and 0.57 (8):0.43 (8) for anion D.

Related literature

For general background to pyrazole derivatives and their pharmacological activities, see: Ohno et al. (2004 ▶); Patel et al. (2010 ▶); Siu et al. (2008 ▶); Sullivan et al. (2006 ▶); Ragavan et al. (2009 ▶, 2010 ▶). For related structures, see: Abdul-Ghani et al. (1995 ▶); Ge et al. (2011 ▶); Han et al. (2011 ▶); Jasinski et al. (2010 ▶); Yamuna et al. (2013 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C9H8FN2 +·C2F3O2 −

M = 276.19

Monoclinic,

a = 6.7828 (2) Å

b = 16.8263 (6) Å

c = 10.4004 (4) Å

β = 93.354 (3)°

V = 1184.96 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.15 mm−1

T = 173 K

0.32 × 0.14 × 0.12 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.867, T max = 1.000

13825 measured reflections

7270 independent reflections

5352 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.110

S = 1.02

7270 reflections

419 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814005200/su2707sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814005200/su2707Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814005200/su2707Isup3.cml

CCDC reference: 990481

Additional supporting information: crystallographic information; 3D view; checkCIF report

C9H8FN2+·C2F3O2−	F(000) = 560
Mr = 276.19	Dx = 1.548 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 6.7828 (2) Å	Cell parameters from 3244 reflections
b = 16.8263 (6) Å	θ = 3.0–32.8°
c = 10.4004 (4) Å	µ = 0.15 mm−1
β = 93.354 (3)°	T = 173 K
V = 1184.96 (8) Å3	Block, colourless
Z = 4	0.32 × 0.14 × 0.12 mm

Agilent Xcalibur (Eos, Gemini) diffractometer	7270 independent reflections
Radiation source: Enhance (Mo) X-ray Source	5352 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1	Rint = 0.029
ω scans	θmax = 32.9°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	h = −9→9
Tmin = 0.867, Tmax = 1.000	k = −24→23
13825 measured reflections	l = −15→15

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.110	w = 1/[σ2(Fo2) + (0.0401P)2 + 0.1594P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
7270 reflections	Δρmax = 0.18 e Å−3
419 parameters	Δρmin = −0.21 e Å−3
1 restraint

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
F1D	0.7862 (10)	0.7079 (9)	0.8704 (15)	0.089 (4)	0.73 (5)
F1DA	0.793 (4)	0.668 (4)	0.912 (3)	0.123 (11)	0.27 (5)
F2D	0.6499 (18)	0.7180 (7)	0.6830 (13)	0.112 (4)	0.63 (5)
F2DA	0.686 (5)	0.7292 (9)	0.731 (5)	0.152 (11)	0.37 (5)
F3D	0.558 (2)	0.6299 (6)	0.823 (2)	0.081 (4)	0.57 (8)
F3DA	0.543 (3)	0.6355 (16)	0.788 (5)	0.114 (7)	0.43 (8)
O1D	1.0279 (3)	0.63369 (12)	0.7099 (2)	0.0408 (5)
O2D	0.7848 (3)	0.54440 (13)	0.6797 (2)	0.0499 (6)
C1D	0.8581 (4)	0.60784 (15)	0.7155 (3)	0.0335 (5)
C2D	0.7130 (5)	0.6654 (2)	0.7773 (4)	0.0560 (9)
F1C	0.7172 (16)	0.7924 (4)	0.330 (2)	0.144 (9)	0.58 (3)
F1CA	0.743 (2)	0.7792 (12)	0.237 (2)	0.121 (8)	0.42 (3)
F2C	0.4749 (11)	0.7172 (5)	0.3343 (11)	0.095 (5)	0.540 (14)
F2CA	0.624 (3)	0.7661 (11)	0.4070 (14)	0.179 (9)	0.460 (14)
F3C	0.628 (2)	0.7258 (9)	0.1734 (6)	0.116 (5)	0.55 (2)
F3CA	0.503 (3)	0.7082 (5)	0.248 (3)	0.214 (16)	0.45 (2)
O1C	0.9686 (3)	0.67332 (13)	0.3635 (2)	0.0491 (5)
O2C	0.7104 (3)	0.59074 (12)	0.3406 (2)	0.0547 (6)
C1C	0.7934 (5)	0.65565 (15)	0.3406 (3)	0.0365 (6)
C2C	0.6556 (6)	0.72546 (19)	0.3014 (4)	0.0599 (10)
F1B	0.6835 (3)	0.37120 (13)	−0.20823 (17)	0.0577 (5)
N1B	0.8500 (3)	0.42473 (13)	0.5212 (2)	0.0329 (5)
H1B	0.844 (5)	0.461 (2)	0.589 (4)	0.058 (10)*
N2B	0.8131 (3)	0.44327 (13)	0.3969 (2)	0.0284 (4)
H2B	0.783 (7)	0.492 (3)	0.375 (4)	0.077 (14)*
C1B	0.8796 (4)	0.34634 (17)	0.5313 (3)	0.0372 (6)
H1BA	0.9083	0.3185	0.6073	0.045*
C2B	0.8602 (4)	0.31413 (16)	0.4097 (3)	0.0349 (6)
H2BA	0.8738	0.2609	0.3881	0.042*
C3B	0.8161 (3)	0.37683 (15)	0.3249 (2)	0.0266 (5)
C4B	0.7787 (3)	0.37670 (16)	0.1853 (2)	0.0270 (5)
C5B	0.7429 (3)	0.44680 (16)	0.1155 (3)	0.0309 (5)
H5B	0.7399	0.4951	0.1587	0.037*
C6B	0.7119 (4)	0.44506 (18)	−0.0168 (3)	0.0360 (6)
H6B	0.6890	0.4916	−0.0635	0.043*
C7B	0.7158 (4)	0.3729 (2)	−0.0777 (3)	0.0391 (6)
C8B	0.7496 (5)	0.30331 (18)	−0.0135 (3)	0.0443 (7)
H8B	0.7517	0.2554	−0.0581	0.053*
C9B	0.7808 (4)	0.30496 (16)	0.1193 (3)	0.0364 (6)
H9B	0.8032	0.2578	0.1645	0.044*
F1A	0.1746 (3)	0.46388 (14)	−0.16103 (17)	0.0633 (6)
N1A	0.2469 (3)	0.54317 (14)	0.5635 (2)	0.0342 (5)
H1A	0.179 (5)	0.578 (2)	0.622 (3)	0.054 (10)*
N2A	0.2056 (3)	0.55446 (14)	0.4364 (2)	0.0304 (4)
H2A	0.127 (5)	0.594 (2)	0.412 (3)	0.045 (9)*
C1A	0.3425 (4)	0.47499 (18)	0.5801 (3)	0.0374 (6)
H1AA	0.3878	0.4537	0.6589	0.045*
C2A	0.3641 (4)	0.44055 (17)	0.4604 (3)	0.0334 (5)
H2AA	0.4243	0.3923	0.4433	0.040*
C3A	0.2767 (3)	0.49337 (14)	0.3714 (2)	0.0272 (5)
C4A	0.2539 (3)	0.48770 (15)	0.2306 (2)	0.0287 (5)
C5A	0.2251 (4)	0.55489 (17)	0.1529 (3)	0.0375 (6)
H5A	0.2229	0.6051	0.1902	0.045*
C6A	0.1999 (5)	0.5467 (2)	0.0206 (3)	0.0444 (7)
H6A	0.1812	0.5911	−0.0320	0.053*
C7A	0.2032 (4)	0.47215 (19)	−0.0312 (3)	0.0410 (7)
C8A	0.2336 (4)	0.40478 (18)	0.0413 (3)	0.0379 (6)
H8A	0.2373	0.3550	0.0028	0.045*
C9A	0.2588 (4)	0.41308 (16)	0.1737 (3)	0.0305 (5)
H9A	0.2792	0.3682	0.2250	0.037*

	U11	U22	U33	U12	U13	U23
F1D	0.075 (4)	0.083 (6)	0.109 (6)	−0.001 (3)	0.018 (3)	−0.066 (5)
F1DA	0.160 (17)	0.13 (3)	0.076 (13)	0.036 (13)	0.030 (9)	−0.068 (16)
F2D	0.148 (6)	0.081 (6)	0.106 (6)	0.084 (6)	0.007 (6)	0.008 (4)
F2DA	0.215 (19)	0.022 (5)	0.23 (2)	0.023 (8)	0.147 (18)	0.008 (9)
F3D	0.083 (7)	0.041 (5)	0.126 (7)	−0.002 (4)	0.070 (6)	−0.009 (6)
F3DA	0.043 (6)	0.118 (14)	0.184 (17)	−0.015 (6)	0.031 (8)	−0.081 (11)
O1D	0.0453 (11)	0.0305 (10)	0.0475 (12)	−0.0042 (9)	0.0114 (9)	−0.0045 (8)
O2D	0.0491 (12)	0.0356 (11)	0.0655 (15)	−0.0043 (9)	0.0070 (10)	−0.0206 (10)
C1D	0.0442 (15)	0.0257 (12)	0.0309 (13)	0.0004 (10)	0.0038 (11)	−0.0035 (10)
C2D	0.052 (2)	0.0357 (17)	0.082 (3)	−0.0051 (14)	0.0195 (18)	−0.0178 (17)
F1C	0.095 (7)	0.019 (3)	0.30 (2)	0.009 (3)	−0.123 (10)	−0.021 (6)
F1CA	0.131 (9)	0.084 (10)	0.146 (15)	0.002 (7)	−0.019 (9)	0.085 (10)
F2C	0.053 (4)	0.064 (5)	0.171 (10)	0.032 (4)	0.036 (6)	0.030 (5)
F2CA	0.23 (2)	0.111 (11)	0.197 (12)	0.118 (12)	−0.002 (11)	−0.057 (9)
F3C	0.133 (9)	0.148 (10)	0.064 (4)	0.069 (8)	−0.023 (4)	0.032 (4)
F3CA	0.142 (14)	0.033 (4)	0.44 (4)	−0.005 (7)	−0.221 (19)	0.004 (11)
O1C	0.0460 (12)	0.0312 (11)	0.0684 (15)	0.0051 (9)	−0.0115 (10)	−0.0022 (9)
O2C	0.0573 (14)	0.0239 (11)	0.0811 (17)	0.0021 (9)	−0.0101 (12)	0.0003 (10)
C1C	0.0483 (16)	0.0226 (12)	0.0370 (14)	0.0065 (11)	−0.0096 (12)	−0.0027 (10)
C2C	0.058 (2)	0.0259 (15)	0.092 (3)	0.0019 (14)	−0.028 (2)	0.0049 (16)
F1B	0.0747 (14)	0.0629 (12)	0.0345 (9)	−0.0106 (11)	−0.0057 (9)	−0.0004 (9)
N1B	0.0306 (11)	0.0331 (12)	0.0351 (13)	0.0018 (8)	0.0032 (9)	−0.0047 (9)
N2B	0.0262 (10)	0.0213 (10)	0.0378 (12)	0.0013 (8)	0.0036 (8)	−0.0006 (8)
C1B	0.0400 (15)	0.0345 (14)	0.0371 (15)	0.0060 (11)	0.0019 (12)	0.0019 (11)
C2B	0.0432 (15)	0.0234 (12)	0.0382 (15)	0.0047 (11)	0.0043 (11)	−0.0005 (10)
C3B	0.0228 (10)	0.0219 (10)	0.0357 (13)	0.0012 (9)	0.0056 (9)	0.0003 (10)
C4B	0.0209 (10)	0.0265 (11)	0.0339 (12)	−0.0020 (9)	0.0033 (9)	0.0002 (10)
C5B	0.0256 (11)	0.0259 (12)	0.0414 (15)	−0.0006 (9)	0.0040 (10)	0.0013 (10)
C6B	0.0297 (12)	0.0397 (15)	0.0385 (15)	−0.0012 (11)	0.0013 (11)	0.0099 (12)
C7B	0.0376 (14)	0.0469 (16)	0.0323 (14)	−0.0073 (13)	−0.0018 (11)	0.0001 (12)
C8B	0.057 (2)	0.0367 (16)	0.0384 (16)	−0.0037 (13)	−0.0010 (13)	−0.0072 (12)
C9B	0.0437 (15)	0.0268 (13)	0.0383 (15)	−0.0012 (11)	−0.0005 (11)	−0.0014 (11)
F1A	0.0772 (14)	0.0833 (16)	0.0299 (10)	0.0056 (12)	0.0085 (9)	−0.0018 (9)
N1A	0.0292 (11)	0.0404 (13)	0.0329 (12)	0.0009 (9)	0.0015 (9)	−0.0032 (9)
N2A	0.0259 (10)	0.0298 (11)	0.0351 (12)	−0.0004 (8)	−0.0022 (8)	−0.0005 (9)
C1A	0.0323 (13)	0.0458 (17)	0.0345 (14)	0.0048 (11)	0.0035 (11)	0.0057 (12)
C2A	0.0287 (12)	0.0380 (14)	0.0341 (14)	0.0049 (10)	0.0056 (10)	0.0066 (11)
C3A	0.0213 (10)	0.0277 (12)	0.0326 (13)	−0.0024 (9)	0.0018 (9)	0.0012 (9)
C4A	0.0227 (11)	0.0315 (13)	0.0319 (13)	−0.0015 (9)	0.0029 (9)	0.0016 (10)
C5A	0.0430 (15)	0.0320 (14)	0.0375 (15)	−0.0048 (11)	0.0015 (12)	0.0031 (11)
C6A	0.0466 (16)	0.0470 (17)	0.0398 (17)	−0.0019 (14)	0.0046 (13)	0.0131 (13)
C7A	0.0358 (14)	0.059 (2)	0.0292 (14)	0.0001 (13)	0.0064 (11)	−0.0013 (13)
C8A	0.0323 (13)	0.0418 (15)	0.0405 (16)	−0.0011 (11)	0.0100 (12)	−0.0076 (12)
C9A	0.0249 (11)	0.0323 (13)	0.0348 (14)	0.0000 (9)	0.0056 (10)	0.0020 (10)

F1D—C2D	1.281 (8)	C4B—C9B	1.389 (4)
F1DA—C2D	1.47 (3)	C5B—H5B	0.9300
F2D—C2D	1.371 (9)	C5B—C6B	1.380 (4)
F2DA—C2D	1.19 (2)	C6B—H6B	0.9300
F3D—C2D	1.324 (11)	C6B—C7B	1.370 (4)
F3DA—C2D	1.270 (18)	C7B—C8B	1.361 (4)
O1D—C1D	1.236 (3)	C8B—H8B	0.9300
O2D—C1D	1.226 (3)	C8B—C9B	1.385 (4)
C1D—C2D	1.546 (4)	C9B—H9B	0.9300
F1C—C2C	1.232 (6)	F1A—C7A	1.360 (3)
F1CA—C2C	1.291 (11)	N1A—H1A	0.98 (4)
F2C—C2C	1.299 (7)	N1A—N2A	1.349 (3)
F2CA—C2C	1.322 (11)	N1A—C1A	1.324 (4)
F3C—C2C	1.333 (8)	N2A—H2A	0.88 (4)
F3CA—C2C	1.183 (8)	N2A—C3A	1.336 (3)
O1C—C1C	1.234 (4)	C1A—H1AA	0.9300
O2C—C1C	1.229 (3)	C1A—C2A	1.389 (4)
C1C—C2C	1.541 (4)	C2A—H2AA	0.9300
F1B—C7B	1.363 (3)	C2A—C3A	1.390 (4)
N1B—H1B	0.94 (4)	C3A—C4A	1.467 (3)
N1B—N2B	1.340 (3)	C4A—C5A	1.397 (4)
N1B—C1B	1.337 (3)	C4A—C9A	1.389 (4)
N2B—H2B	0.87 (5)	C5A—H5A	0.9300
N2B—C3B	1.346 (3)	C5A—C6A	1.384 (4)
C1B—H1BA	0.9300	C6A—H6A	0.9300
C1B—C2B	1.375 (4)	C6A—C7A	1.366 (4)
C2B—H2BA	0.9300	C7A—C8A	1.371 (4)
C2B—C3B	1.396 (4)	C8A—H8A	0.9300
C3B—C4B	1.459 (3)	C8A—C9A	1.384 (4)
C4B—C5B	1.399 (4)	C9A—H9A	0.9300
O1D—C1D—C2D	114.6 (2)	C4B—C5B—H5B	119.6
O2D—C1D—O1D	130.8 (3)	C6B—C5B—C4B	120.8 (3)
O2D—C1D—C2D	114.5 (3)	C6B—C5B—H5B	119.6
F1D—C2D—F2D	105.7 (11)	C5B—C6B—H6B	120.9
F1D—C2D—F3D	105.0 (11)	C7B—C6B—C5B	118.3 (3)
F1D—C2D—C1D	115.9 (5)	C7B—C6B—H6B	120.9
F1DA—C2D—C1D	101.8 (14)	F1B—C7B—C6B	118.2 (3)
F2D—C2D—C1D	106.7 (6)	C8B—C7B—F1B	118.9 (3)
F2DA—C2D—F1DA	114 (4)	C8B—C7B—C6B	122.9 (3)
F2DA—C2D—F3DA	106 (3)	C7B—C8B—H8B	120.6
F2DA—C2D—C1D	119.1 (13)	C7B—C8B—C9B	118.9 (3)
F3D—C2D—F2D	109.2 (10)	C9B—C8B—H8B	120.6
F3D—C2D—C1D	114.0 (6)	C4B—C9B—H9B	119.8
F3DA—C2D—F1DA	103 (3)	C8B—C9B—C4B	120.3 (3)
F3DA—C2D—C1D	113.0 (9)	C8B—C9B—H9B	119.8
O1C—C1C—C2C	115.4 (2)	N2A—N1A—H1A	117 (2)
O2C—C1C—O1C	130.5 (3)	C1A—N1A—H1A	133 (2)
O2C—C1C—C2C	114.0 (3)	C1A—N1A—N2A	108.7 (2)
F1C—C2C—F2C	110.2 (10)	N1A—N2A—H2A	118 (2)
F1C—C2C—F3C	105.3 (12)	C3A—N2A—N1A	109.1 (2)
F1C—C2C—C1C	116.2 (4)	C3A—N2A—H2A	132 (2)
F1CA—C2C—F2CA	99.9 (15)	N1A—C1A—H1AA	125.6
F1CA—C2C—C1C	112.3 (6)	N1A—C1A—C2A	108.7 (2)
F2C—C2C—F3C	100.6 (7)	C2A—C1A—H1AA	125.6
F2C—C2C—C1C	114.6 (5)	C1A—C2A—H2AA	127.3
F2CA—C2C—C1C	107.5 (6)	C1A—C2A—C3A	105.5 (2)
F3C—C2C—C1C	108.3 (4)	C3A—C2A—H2AA	127.3
F3CA—C2C—F1CA	110.5 (16)	N2A—C3A—C2A	107.9 (2)
F3CA—C2C—F2CA	109.4 (17)	N2A—C3A—C4A	122.3 (2)
F3CA—C2C—C1C	116.0 (5)	C2A—C3A—C4A	129.7 (2)
N2B—N1B—H1B	124 (2)	C5A—C4A—C3A	121.9 (2)
C1B—N1B—H1B	127 (2)	C9A—C4A—C3A	118.7 (2)
C1B—N1B—N2B	108.9 (2)	C9A—C4A—C5A	119.4 (2)
N1B—N2B—H2B	120 (3)	C4A—C5A—H5A	120.0
N1B—N2B—C3B	109.6 (2)	C6A—C5A—C4A	120.0 (3)
C3B—N2B—H2B	130 (3)	C6A—C5A—H5A	120.0
N1B—C1B—H1BA	125.9	C5A—C6A—H6A	120.7
N1B—C1B—C2B	108.1 (3)	C7A—C6A—C5A	118.7 (3)
C2B—C1B—H1BA	125.9	C7A—C6A—H6A	120.7
C1B—C2B—H2BA	126.6	F1A—C7A—C6A	118.8 (3)
C1B—C2B—C3B	106.8 (2)	F1A—C7A—C8A	118.0 (3)
C3B—C2B—H2BA	126.6	C6A—C7A—C8A	123.2 (3)
N2B—C3B—C2B	106.6 (2)	C7A—C8A—H8A	121.0
N2B—C3B—C4B	123.2 (2)	C7A—C8A—C9A	118.0 (3)
C2B—C3B—C4B	130.2 (2)	C9A—C8A—H8A	121.0
C5B—C4B—C3B	122.0 (2)	C4A—C9A—H9A	119.7
C9B—C4B—C3B	119.1 (2)	C8A—C9A—C4A	120.7 (2)
C9B—C4B—C5B	118.9 (2)	C8A—C9A—H9A	119.7
O1D—C1D—C2D—F1D	−35.8 (11)	C1B—C2B—C3B—C4B	−179.3 (2)
O1D—C1D—C2D—F1DA	−67 (3)	C2B—C3B—C4B—C5B	−177.8 (2)
O1D—C1D—C2D—F2D	81.5 (8)	C2B—C3B—C4B—C9B	1.4 (4)
O1D—C1D—C2D—F2DA	58 (3)	C3B—C4B—C5B—C6B	178.7 (2)
O1D—C1D—C2D—F3D	−157.9 (12)	C3B—C4B—C9B—C8B	−178.7 (2)
O1D—C1D—C2D—F3DA	−177 (3)	C4B—C5B—C6B—C7B	0.5 (4)
O2D—C1D—C2D—F1D	144.7 (11)	C5B—C4B—C9B—C8B	0.6 (4)
O2D—C1D—C2D—F1DA	113 (3)	C5B—C6B—C7B—F1B	179.5 (2)
O2D—C1D—C2D—F2D	−98.0 (8)	C5B—C6B—C7B—C8B	−0.3 (4)
O2D—C1D—C2D—F2DA	−121 (3)	C6B—C7B—C8B—C9B	0.3 (5)
O2D—C1D—C2D—F3D	22.6 (12)	C7B—C8B—C9B—C4B	−0.4 (4)
O2D—C1D—C2D—F3DA	4 (3)	C9B—C4B—C5B—C6B	−0.6 (3)
O1C—C1C—C2C—F1C	−19.2 (15)	F1A—C7A—C8A—C9A	−178.7 (2)
O1C—C1C—C2C—F1CA	33.1 (15)	N1A—N2A—C3A—C2A	0.9 (3)
O1C—C1C—C2C—F2C	−149.6 (7)	N1A—N2A—C3A—C4A	179.4 (2)
O1C—C1C—C2C—F2CA	−75.8 (14)	N1A—C1A—C2A—C3A	0.7 (3)
O1C—C1C—C2C—F3C	99.0 (9)	N2A—N1A—C1A—C2A	−0.1 (3)
O1C—C1C—C2C—F3CA	161 (2)	N2A—C3A—C4A—C5A	24.1 (4)
O2C—C1C—C2C—F1C	162.5 (15)	N2A—C3A—C4A—C9A	−155.1 (2)
O2C—C1C—C2C—F1CA	−145.2 (14)	C1A—N1A—N2A—C3A	−0.5 (3)
O2C—C1C—C2C—F2C	32.1 (8)	C1A—C2A—C3A—N2A	−0.9 (3)
O2C—C1C—C2C—F2CA	105.9 (13)	C1A—C2A—C3A—C4A	−179.3 (2)
O2C—C1C—C2C—F3C	−79.3 (9)	C2A—C3A—C4A—C5A	−157.8 (3)
O2C—C1C—C2C—F3CA	−17 (2)	C2A—C3A—C4A—C9A	23.0 (4)
F1B—C7B—C8B—C9B	−179.5 (3)	C3A—C4A—C5A—C6A	−178.6 (2)
N1B—N2B—C3B—C2B	−0.9 (3)	C3A—C4A—C9A—C8A	178.6 (2)
N1B—N2B—C3B—C4B	179.2 (2)	C4A—C5A—C6A—C7A	0.2 (4)
N1B—C1B—C2B—C3B	−0.3 (3)	C5A—C4A—C9A—C8A	−0.6 (4)
N2B—N1B—C1B—C2B	−0.2 (3)	C5A—C6A—C7A—F1A	178.7 (3)
N2B—C3B—C4B—C5B	2.1 (3)	C5A—C6A—C7A—C8A	−1.1 (5)
N2B—C3B—C4B—C9B	−178.6 (2)	C6A—C7A—C8A—C9A	1.1 (4)
C1B—N1B—N2B—C3B	0.7 (3)	C7A—C8A—C9A—C4A	−0.2 (4)
C1B—C2B—C3B—N2B	0.7 (3)	C9A—C4A—C5A—C6A	0.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1B—H1B···O2D	0.94 (4)	1.75 (4)	2.656 (3)	162 (4)
N2B—H2B···O2C	0.87 (5)	1.77 (5)	2.634 (3)	175 (4)
N1A—H1A···O1Di	0.98 (4)	1.69 (4)	2.665 (3)	170 (3)
N2A—H2A···O1Ci	0.88 (4)	1.77 (4)	2.649 (3)	180 (4)
C1B—H1BA···O1Cii	0.93	2.59	3.256 (3)	129
C2B—H2BA···O1Dii	0.93	2.48	3.384 (3)	165
C5B—H5B···O2C	0.93	2.50	3.385 (4)	159
C9A—H9A···F2DAiii	0.93	2.39	3.26 (3)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1B—H1B⋯O2D	0.94 (4)	1.75 (4)	2.656 (3)	162 (4)
N2B—H2B⋯O2C	0.87 (5)	1.77 (5)	2.634 (3)	175 (4)
N1A—H1A⋯O1D i	0.98 (4)	1.69 (4)	2.665 (3)	170 (3)
N2A—H2A⋯O1C i	0.88 (4)	1.77 (4)	2.649 (3)	180 (4)
C1B—H1BA⋯O1C ii	0.93	2.59	3.256 (3)	129
C2B—H2BA⋯O1D ii	0.93	2.48	3.384 (3)	165
C5B—H5B⋯O2C	0.93	2.50	3.385 (4)	159
C9A—H9A⋯F2DA iii	0.93	2.39	3.26 (3)	156

Symmetry codes: (i) ; (ii) ; (iii) .