Flunarizinium isonicotinate.

In the cation of the title salt {systematic name: 4-[bis-(4-fluoro-phen-yl)meth-yl]-1-[(2E)-3-phenyl-prop-2-en-1-yl]piperazin-1-ium pyridine-4-carboxyl-ate}, C26H27F2N2 (+)·C6H4NO2 (-), the piperazine ring is in a slightly distorted chair conformation. The dihedral angle between the mean planes of the fluoro-substituted benzene rings is 81.9 (1)° and these benzene rings form dihedral angles of 6.5 (1) and 87.8 (1)° with the phenyl ring. In the crystal, a single N-H⋯O hydrogen bond links the cation and the anion. In addition, weak C-H⋯O hydrogen bonds and π-π stacking inter-actions involving one of the fluoro-substituted benzene rings and the phenyl ring, with a centroid-centroid distance of 3.700 (7) Å, link mol-ecules along [100].

Related literature

For the bioligical activities of flunarizine, see: Amery (1983 ▶); Holmes et al. (1984 ▶). For related structures, see: Kavitha et al. (2013a ▶,b ▶,c ▶,d ▶). For puckering parameters, see Cremer & Pople (1975 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C26H27F2N2 +·C6H4NO2 −

M = 527.60

Monoclinic,

a = 11.0023 (3) Å

b = 10.6435 (3) Å

c = 11.3393 (3) Å

β = 92.481 (3)°

V = 1326.63 (6) Å3

Z = 2

Cu Kα radiation

μ = 0.76 mm−1

T = 173 K

0.22 × 0.12 × 0.06 mm

Data collection

Agilent Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.781, T max = 1.000

8232 measured reflections

3403 independent reflections

3238 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.110

S = 1.02

3403 reflections

357 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 857 Friedel pairs

Absolute structure parameter: 0.2 (2)

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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814010423/lh5702sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814010423/lh5702Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814010423/lh5702Isup3.cml

CCDC reference: 1001665

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

C26H27F2N2+·C6H4NO2−	F(000) = 556
Mr = 527.60	Dx = 1.321 Mg m−3
Monoclinic, Pc	Cu Kα radiation, λ = 1.54184 Å
a = 11.0023 (3) Å	Cell parameters from 4115 reflections
b = 10.6435 (3) Å	θ = 4.0–71.5°
c = 11.3393 (3) Å	µ = 0.76 mm−1
β = 92.481 (3)°	T = 173 K
V = 1326.63 (6) Å3	Block, colourless
Z = 2	0.22 × 0.12 × 0.06 mm

Agilent Eos Gemini diffractometer	3403 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3238 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1	Rint = 0.042
ω scans	θmax = 71.3°, θmin = 4.0°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	h = −13→7
Tmin = 0.781, Tmax = 1.000	k = −12→13
8232 measured reflections	l = −13→13

Refinement on F2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0764P)2 + 0.0707P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.040	(Δ/σ)max < 0.001
wR(F2) = 0.110	Δρmax = 0.18 e Å−3
S = 1.02	Δρmin = −0.20 e Å−3
3403 reflections	Extinction correction: SHELXL2012 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
357 parameters	Extinction coefficient: 0.0050 (8)
2 restraints	Absolute structure: Classical Flack method preferred over Parsons because s.u. lower. 857 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.2 (2)
Hydrogen site location: mixed

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
F1A	−0.1154 (2)	1.19666 (19)	0.98648 (18)	0.0538 (5)
F2A	0.0248 (2)	1.5040 (2)	0.2592 (2)	0.0696 (7)
N1A	0.2572 (2)	1.0742 (2)	0.58937 (19)	0.0263 (5)
N2A	0.4826 (2)	0.9352 (2)	0.5718 (2)	0.0272 (5)
H2A	0.461 (4)	0.877 (4)	0.513 (4)	0.048 (10)*
C1A	0.1259 (2)	1.0983 (2)	0.5668 (2)	0.0270 (5)
H1A	0.0897	1.0231	0.5298	0.032*
C2A	0.0641 (2)	1.1206 (2)	0.6827 (2)	0.0271 (5)
C3A	0.1256 (3)	1.1748 (2)	0.7798 (2)	0.0291 (5)
H3A	0.2080	1.1932	0.7763	0.035*
C4A	0.0650 (3)	1.2017 (2)	0.8823 (3)	0.0336 (6)
H4A	0.1062	1.2378	0.9472	0.040*
C5A	−0.0561 (3)	1.1741 (3)	0.8856 (3)	0.0362 (6)
C6A	−0.1212 (3)	1.1206 (3)	0.7915 (3)	0.0375 (7)
H6A	−0.2037	1.1033	0.7959	0.045*
C7A	−0.0596 (3)	1.0937 (3)	0.6905 (3)	0.0323 (6)
H7A	−0.1016	1.0569	0.6264	0.039*
C8A	0.1019 (2)	1.2089 (2)	0.4835 (2)	0.0286 (5)
C9A	0.0496 (3)	1.1870 (3)	0.3720 (3)	0.0350 (6)
H9A	0.0320	1.1052	0.3482	0.042*
C10A	0.0231 (3)	1.2866 (4)	0.2952 (3)	0.0441 (8)
H10A	−0.0122	1.2723	0.2204	0.053*
C11A	0.0504 (3)	1.4057 (3)	0.3327 (3)	0.0460 (8)
C12A	0.1034 (3)	1.4311 (3)	0.4423 (3)	0.0454 (8)
H12A	0.1216	1.5132	0.4649	0.054*
C13A	0.1292 (3)	1.3318 (3)	0.5183 (3)	0.0366 (6)
H13A	0.1649	1.3471	0.5927	0.044*
C14A	0.3274 (2)	1.0792 (3)	0.4828 (2)	0.0301 (6)
H14A	0.3156	1.1601	0.4446	0.036*
H14B	0.2991	1.0145	0.4281	0.036*
C15A	0.4611 (3)	1.0600 (3)	0.5144 (2)	0.0297 (6)
H15A	0.5070	1.0650	0.4434	0.036*
H15B	0.4895	1.1261	0.5676	0.036*
C16A	0.4061 (2)	0.9246 (2)	0.6769 (2)	0.0280 (5)
H16A	0.4332	0.9853	0.7362	0.034*
H16B	0.4148	0.8413	0.7108	0.034*
C17A	0.2741 (3)	0.9485 (2)	0.6415 (2)	0.0286 (5)
H17A	0.2463	0.8855	0.5847	0.034*
H17B	0.2253	0.9412	0.7104	0.034*
C18A	0.6153 (3)	0.9189 (3)	0.6037 (3)	0.0338 (6)
H18A	0.6603	0.9180	0.5321	0.041*
H18B	0.6435	0.9900	0.6508	0.041*
C19A	0.6416 (3)	0.8002 (3)	0.6713 (3)	0.0328 (6)
H19A	0.6247	0.7235	0.6349	0.039*
C20A	0.6877 (3)	0.8008 (3)	0.7806 (3)	0.0324 (6)
H20A	0.7019	0.8796	0.8139	0.039*
C21A	0.7198 (2)	0.6926 (3)	0.8567 (2)	0.0306 (6)
C22A	0.7056 (3)	0.5679 (3)	0.8189 (3)	0.0360 (6)
H22A	0.6718	0.5512	0.7440	0.043*
C23A	0.7412 (3)	0.4696 (3)	0.8918 (3)	0.0420 (7)
H23A	0.7306	0.3872	0.8658	0.050*
C24A	0.7929 (3)	0.4928 (3)	1.0041 (3)	0.0439 (7)
H24A	0.8182	0.4263	1.0523	0.053*
C25A	0.8064 (3)	0.6152 (3)	1.0436 (3)	0.0420 (7)
H25A	0.8398	0.6314	1.1188	0.050*
C26A	0.7696 (3)	0.7141 (3)	0.9699 (3)	0.0353 (6)
H26A	0.7785	0.7963	0.9969	0.042*
O1B	0.4163 (2)	0.2192 (2)	0.9087 (2)	0.0479 (6)
O2B	0.5711 (2)	0.1759 (2)	0.7956 (2)	0.0434 (5)
N1B	0.3838 (3)	0.5717 (3)	0.6228 (4)	0.0636 (10)
C1B	0.4838 (3)	0.2391 (3)	0.8226 (2)	0.0326 (6)
C2B	0.4475 (3)	0.3537 (3)	0.7500 (2)	0.0328 (6)
C3B	0.4993 (3)	0.3812 (3)	0.6435 (3)	0.0438 (7)
H3B	0.5574	0.3281	0.6132	0.053*
C4B	0.4628 (4)	0.4892 (4)	0.5830 (3)	0.0604 (11)
H4B	0.4956	0.5046	0.5102	0.072*
C5B	0.3354 (4)	0.5444 (4)	0.7234 (4)	0.0584 (10)
H5B	0.2787	0.6003	0.7518	0.070*
C6B	0.3624 (3)	0.4388 (3)	0.7899 (3)	0.0401 (7)
H6B	0.3244	0.4246	0.8603	0.048*

	U11	U22	U33	U12	U13	U23
F1A	0.0610 (13)	0.0588 (12)	0.0435 (11)	0.0125 (10)	0.0239 (9)	0.0020 (9)
F2A	0.0701 (15)	0.0701 (14)	0.0688 (15)	0.0143 (11)	0.0076 (12)	0.0431 (12)
N1A	0.0251 (11)	0.0285 (10)	0.0256 (11)	0.0021 (8)	0.0031 (8)	0.0020 (8)
N2A	0.0258 (12)	0.0318 (11)	0.0238 (11)	0.0027 (9)	−0.0002 (8)	−0.0024 (9)
C1A	0.0282 (13)	0.0253 (12)	0.0272 (13)	−0.0001 (10)	−0.0023 (10)	−0.0015 (10)
C2A	0.0277 (13)	0.0240 (12)	0.0296 (13)	0.0034 (10)	0.0017 (10)	0.0034 (9)
C3A	0.0301 (13)	0.0258 (12)	0.0316 (13)	0.0011 (10)	0.0017 (10)	0.0002 (9)
C4A	0.0445 (16)	0.0266 (12)	0.0295 (13)	0.0066 (11)	0.0006 (12)	−0.0001 (10)
C5A	0.0448 (17)	0.0306 (13)	0.0345 (14)	0.0099 (12)	0.0149 (12)	0.0086 (11)
C6A	0.0300 (14)	0.0377 (15)	0.0452 (17)	0.0050 (12)	0.0074 (12)	0.0109 (12)
C7A	0.0305 (14)	0.0316 (13)	0.0342 (14)	0.0005 (10)	−0.0029 (11)	0.0066 (11)
C8A	0.0257 (12)	0.0324 (13)	0.0277 (13)	0.0044 (11)	0.0021 (10)	0.0024 (10)
C9A	0.0313 (14)	0.0428 (15)	0.0309 (14)	0.0020 (11)	0.0016 (11)	0.0018 (12)
C10A	0.0341 (16)	0.067 (2)	0.0311 (15)	0.0048 (14)	−0.0008 (12)	0.0123 (14)
C11A	0.0438 (18)	0.0467 (18)	0.0480 (19)	0.0079 (14)	0.0085 (14)	0.0221 (15)
C12A	0.0536 (19)	0.0324 (15)	0.0510 (19)	0.0035 (14)	0.0122 (15)	0.0096 (13)
C13A	0.0435 (17)	0.0324 (15)	0.0340 (15)	0.0027 (12)	0.0029 (12)	0.0029 (11)
C14A	0.0310 (14)	0.0338 (13)	0.0255 (13)	0.0031 (11)	0.0032 (11)	0.0035 (10)
C15A	0.0310 (14)	0.0338 (13)	0.0243 (13)	−0.0010 (11)	0.0036 (10)	0.0020 (10)
C16A	0.0305 (14)	0.0298 (12)	0.0238 (12)	0.0038 (10)	0.0019 (10)	0.0026 (10)
C17A	0.0293 (13)	0.0290 (12)	0.0277 (13)	0.0011 (10)	0.0032 (10)	0.0037 (10)
C18A	0.0260 (14)	0.0421 (15)	0.0332 (15)	0.0021 (11)	0.0007 (11)	−0.0016 (11)
C19A	0.0269 (14)	0.0351 (14)	0.0363 (15)	0.0047 (11)	0.0005 (11)	−0.0066 (11)
C20A	0.0276 (13)	0.0329 (14)	0.0368 (14)	−0.0007 (11)	0.0023 (11)	−0.0035 (11)
C21A	0.0220 (12)	0.0361 (14)	0.0338 (15)	−0.0008 (10)	0.0030 (10)	0.0008 (11)
C22A	0.0325 (15)	0.0396 (15)	0.0357 (15)	−0.0031 (12)	−0.0024 (12)	−0.0045 (12)
C23A	0.0389 (17)	0.0326 (14)	0.0545 (19)	0.0005 (13)	0.0029 (14)	−0.0015 (13)
C24A	0.0395 (17)	0.0445 (17)	0.0476 (18)	0.0031 (13)	0.0013 (14)	0.0131 (14)
C25A	0.0391 (16)	0.0529 (18)	0.0338 (14)	0.0006 (14)	−0.0025 (12)	0.0029 (13)
C26A	0.0339 (15)	0.0368 (15)	0.0351 (15)	−0.0031 (12)	0.0015 (12)	−0.0028 (11)
O1B	0.0465 (13)	0.0533 (13)	0.0444 (13)	0.0075 (11)	0.0073 (10)	0.0189 (10)
O2B	0.0362 (12)	0.0411 (11)	0.0529 (13)	0.0060 (9)	0.0027 (10)	−0.0053 (9)
N1B	0.0457 (18)	0.068 (2)	0.077 (2)	−0.0050 (15)	−0.0011 (16)	0.0407 (18)
C1B	0.0317 (14)	0.0346 (14)	0.0311 (13)	−0.0056 (12)	−0.0023 (11)	−0.0033 (11)
C2B	0.0324 (14)	0.0361 (14)	0.0294 (13)	−0.0091 (11)	−0.0023 (10)	−0.0008 (11)
C3B	0.0436 (17)	0.0529 (18)	0.0353 (15)	−0.0173 (14)	0.0043 (13)	−0.0030 (13)
C4B	0.057 (2)	0.087 (3)	0.0363 (18)	−0.026 (2)	−0.0027 (16)	0.0219 (18)
C5B	0.045 (2)	0.050 (2)	0.081 (3)	0.0008 (16)	0.0043 (19)	0.0200 (19)
C6B	0.0408 (17)	0.0391 (15)	0.0407 (17)	−0.0044 (13)	0.0048 (13)	0.0056 (12)

F1A—C5A	1.363 (3)	C16A—H16A	0.9700
F2A—C11A	1.360 (4)	C16A—H16B	0.9700
N1A—C1A	1.479 (3)	C16A—C17A	1.511 (4)
N1A—C14A	1.463 (3)	C17A—H17A	0.9700
N1A—C17A	1.471 (3)	C17A—H17B	0.9700
N2A—H2A	0.94 (4)	C18A—H18A	0.9700
N2A—C15A	1.493 (3)	C18A—H18B	0.9700
N2A—C16A	1.492 (3)	C18A—C19A	1.499 (4)
N2A—C18A	1.499 (3)	C19A—H19A	0.9300
C1A—H1A	0.9800	C19A—C20A	1.319 (4)
C1A—C2A	1.524 (3)	C20A—H20A	0.9300
C1A—C8A	1.525 (3)	C20A—C21A	1.472 (4)
C2A—C3A	1.392 (4)	C21A—C22A	1.401 (4)
C2A—C7A	1.398 (4)	C21A—C26A	1.393 (4)
C3A—H3A	0.9300	C22A—H22A	0.9300
C3A—C4A	1.395 (4)	C22A—C23A	1.379 (4)
C4A—H4A	0.9300	C23A—H23A	0.9300
C4A—C5A	1.366 (4)	C23A—C24A	1.395 (5)
C5A—C6A	1.381 (5)	C24A—H24A	0.9300
C6A—H6A	0.9300	C24A—C25A	1.383 (5)
C6A—C7A	1.386 (4)	C25A—H25A	0.9300
C7A—H7A	0.9300	C25A—C26A	1.393 (4)
C8A—C9A	1.387 (4)	C26A—H26A	0.9300
C8A—C13A	1.394 (4)	O1B—C1B	1.270 (4)
C9A—H9A	0.9300	O2B—C1B	1.223 (4)
C9A—C10A	1.395 (4)	N1B—C4B	1.329 (6)
C10A—H10A	0.9300	N1B—C5B	1.311 (5)
C10A—C11A	1.366 (5)	C1B—C2B	1.515 (4)
C11A—C12A	1.377 (5)	C2B—C3B	1.388 (4)
C12A—H12A	0.9300	C2B—C6B	1.392 (4)
C12A—C13A	1.385 (4)	C3B—H3B	0.9300
C13A—H13A	0.9300	C3B—C4B	1.389 (6)
C14A—H14A	0.9700	C4B—H4B	0.9300
C14A—H14B	0.9700	C5B—H5B	0.9300
C14A—C15A	1.512 (4)	C5B—C6B	1.379 (5)
C15A—H15A	0.9700	C6B—H6B	0.9300
C15A—H15B	0.9700
C14A—N1A—C1A	113.4 (2)	H15A—C15A—H15B	108.0
C14A—N1A—C17A	107.66 (19)	N2A—C16A—H16A	109.6
C17A—N1A—C1A	109.43 (19)	N2A—C16A—H16B	109.6
C15A—N2A—H2A	104 (2)	N2A—C16A—C17A	110.1 (2)
C15A—N2A—C18A	110.1 (2)	H16A—C16A—H16B	108.2
C16A—N2A—H2A	113 (2)	C17A—C16A—H16A	109.6
C16A—N2A—C15A	109.35 (19)	C17A—C16A—H16B	109.6
C16A—N2A—C18A	112.1 (2)	N1A—C17A—C16A	111.3 (2)
C18A—N2A—H2A	108 (2)	N1A—C17A—H17A	109.4
N1A—C1A—H1A	108.0	N1A—C17A—H17B	109.4
N1A—C1A—C2A	110.3 (2)	C16A—C17A—H17A	109.4
N1A—C1A—C8A	112.5 (2)	C16A—C17A—H17B	109.4
C2A—C1A—H1A	108.0	H17A—C17A—H17B	108.0
C2A—C1A—C8A	110.0 (2)	N2A—C18A—H18A	109.1
C8A—C1A—H1A	108.0	N2A—C18A—H18B	109.1
C3A—C2A—C1A	121.8 (2)	H18A—C18A—H18B	107.8
C3A—C2A—C7A	118.5 (2)	C19A—C18A—N2A	112.7 (2)
C7A—C2A—C1A	119.6 (2)	C19A—C18A—H18A	109.1
C2A—C3A—H3A	119.6	C19A—C18A—H18B	109.1
C2A—C3A—C4A	120.7 (3)	C18A—C19A—H19A	118.8
C4A—C3A—H3A	119.6	C20A—C19A—C18A	122.3 (3)
C3A—C4A—H4A	120.6	C20A—C19A—H19A	118.8
C5A—C4A—C3A	118.7 (3)	C19A—C20A—H20A	115.9
C5A—C4A—H4A	120.6	C19A—C20A—C21A	128.3 (3)
F1A—C5A—C4A	119.2 (3)	C21A—C20A—H20A	115.9
F1A—C5A—C6A	118.0 (3)	C22A—C21A—C20A	122.7 (3)
C4A—C5A—C6A	122.8 (3)	C26A—C21A—C20A	119.1 (2)
C5A—C6A—H6A	121.0	C26A—C21A—C22A	118.1 (3)
C5A—C6A—C7A	117.9 (3)	C21A—C22A—H22A	119.6
C7A—C6A—H6A	121.0	C23A—C22A—C21A	120.7 (3)
C2A—C7A—H7A	119.3	C23A—C22A—H22A	119.6
C6A—C7A—C2A	121.4 (3)	C22A—C23A—H23A	119.8
C6A—C7A—H7A	119.3	C22A—C23A—C24A	120.4 (3)
C9A—C8A—C1A	119.3 (2)	C24A—C23A—H23A	119.8
C9A—C8A—C13A	119.4 (3)	C23A—C24A—H24A	120.1
C13A—C8A—C1A	121.3 (2)	C25A—C24A—C23A	119.7 (3)
C8A—C9A—H9A	119.7	C25A—C24A—H24A	120.1
C8A—C9A—C10A	120.6 (3)	C24A—C25A—H25A	120.2
C10A—C9A—H9A	119.7	C24A—C25A—C26A	119.6 (3)
C9A—C10A—H10A	120.9	C26A—C25A—H25A	120.2
C11A—C10A—C9A	118.3 (3)	C21A—C26A—C25A	121.4 (3)
C11A—C10A—H10A	120.9	C21A—C26A—H26A	119.3
F2A—C11A—C10A	119.1 (3)	C25A—C26A—H26A	119.3
F2A—C11A—C12A	118.1 (3)	C5B—N1B—C4B	116.4 (3)
C10A—C11A—C12A	122.8 (3)	O1B—C1B—C2B	113.8 (3)
C11A—C12A—H12A	120.7	O2B—C1B—O1B	126.3 (3)
C11A—C12A—C13A	118.6 (3)	O2B—C1B—C2B	119.9 (3)
C13A—C12A—H12A	120.7	C3B—C2B—C1B	122.3 (3)
C8A—C13A—H13A	119.9	C3B—C2B—C6B	116.9 (3)
C12A—C13A—C8A	120.3 (3)	C6B—C2B—C1B	120.8 (2)
C12A—C13A—H13A	119.9	C2B—C3B—H3B	120.6
N1A—C14A—H14A	109.7	C2B—C3B—C4B	118.9 (3)
N1A—C14A—H14B	109.7	C4B—C3B—H3B	120.6
N1A—C14A—C15A	110.0 (2)	N1B—C4B—C3B	124.0 (3)
H14A—C14A—H14B	108.2	N1B—C4B—H4B	118.0
C15A—C14A—H14A	109.7	C3B—C4B—H4B	118.0
C15A—C14A—H14B	109.7	N1B—C5B—H5B	117.6
N2A—C15A—C14A	111.0 (2)	N1B—C5B—C6B	124.8 (4)
N2A—C15A—H15A	109.4	C6B—C5B—H5B	117.6
N2A—C15A—H15B	109.4	C2B—C6B—H6B	120.5
C14A—C15A—H15A	109.4	C5B—C6B—C2B	119.0 (3)
C14A—C15A—H15B	109.4	C5B—C6B—H6B	120.5
F1A—C5A—C6A—C7A	−177.8 (2)	C14A—N1A—C1A—C8A	−44.2 (3)
F2A—C11A—C12A—C13A	179.6 (3)	C14A—N1A—C17A—C16A	61.8 (3)
N1A—C1A—C2A—C3A	30.7 (3)	C15A—N2A—C16A—C17A	54.7 (3)
N1A—C1A—C2A—C7A	−153.4 (2)	C15A—N2A—C18A—C19A	175.0 (2)
N1A—C1A—C8A—C9A	112.3 (3)	C16A—N2A—C15A—C14A	−55.8 (3)
N1A—C1A—C8A—C13A	−69.0 (3)	C16A—N2A—C18A—C19A	53.1 (3)
N1A—C14A—C15A—N2A	60.2 (3)	C17A—N1A—C1A—C2A	72.5 (3)
N2A—C16A—C17A—N1A	−59.2 (3)	C17A—N1A—C1A—C8A	−164.4 (2)
N2A—C18A—C19A—C20A	−116.8 (3)	C17A—N1A—C14A—C15A	−61.5 (3)
C1A—N1A—C14A—C15A	177.2 (2)	C18A—N2A—C15A—C14A	−179.3 (2)
C1A—N1A—C17A—C16A	−174.5 (2)	C18A—N2A—C16A—C17A	177.0 (2)
C1A—C2A—C3A—C4A	175.8 (2)	C18A—C19A—C20A—C21A	−179.0 (2)
C1A—C2A—C7A—C6A	−175.5 (2)	C19A—C20A—C21A—C22A	0.9 (4)
C1A—C8A—C9A—C10A	178.0 (3)	C19A—C20A—C21A—C26A	179.0 (3)
C1A—C8A—C13A—C12A	−178.2 (3)	C20A—C21A—C22A—C23A	177.5 (3)
C2A—C1A—C8A—C9A	−124.4 (3)	C20A—C21A—C26A—C25A	−177.2 (3)
C2A—C1A—C8A—C13A	54.3 (3)	C21A—C22A—C23A—C24A	−0.5 (5)
C2A—C3A—C4A—C5A	−0.1 (4)	C22A—C21A—C26A—C25A	1.0 (4)
C3A—C2A—C7A—C6A	0.5 (4)	C22A—C23A—C24A—C25A	1.3 (5)
C3A—C4A—C5A—F1A	178.1 (2)	C23A—C24A—C25A—C26A	−0.9 (5)
C3A—C4A—C5A—C6A	−0.1 (4)	C24A—C25A—C26A—C21A	−0.3 (5)
C4A—C5A—C6A—C7A	0.4 (4)	C26A—C21A—C22A—C23A	−0.6 (4)
C5A—C6A—C7A—C2A	−0.7 (4)	O1B—C1B—C2B—C3B	−171.0 (3)
C7A—C2A—C3A—C4A	−0.1 (4)	O1B—C1B—C2B—C6B	11.0 (4)
C8A—C1A—C2A—C3A	−93.9 (3)	O2B—C1B—C2B—C3B	9.0 (4)
C8A—C1A—C2A—C7A	82.0 (3)	O2B—C1B—C2B—C6B	−169.0 (3)
C8A—C9A—C10A—C11A	0.2 (4)	N1B—C5B—C6B—C2B	0.4 (6)
C9A—C8A—C13A—C12A	0.5 (4)	C1B—C2B—C3B—C4B	−178.9 (3)
C9A—C10A—C11A—F2A	−179.8 (3)	C1B—C2B—C6B—C5B	177.5 (3)
C9A—C10A—C11A—C12A	0.5 (5)	C2B—C3B—C4B—N1B	2.7 (6)
C10A—C11A—C12A—C13A	−0.7 (5)	C3B—C2B—C6B—C5B	−0.6 (5)
C11A—C12A—C13A—C8A	0.1 (5)	C4B—N1B—C5B—C6B	1.2 (6)
C13A—C8A—C9A—C10A	−0.7 (4)	C5B—N1B—C4B—C3B	−2.8 (6)
C14A—N1A—C1A—C2A	−167.3 (2)	C6B—C2B—C3B—C4B	−0.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2A···O1Bi	0.94 (4)	1.62 (4)	2.557 (3)	176 (4)
C6A—H6A···O2Bii	0.93	2.60	3.439 (4)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2A—H2A⋯O1B i	0.94 (4)	1.62 (4)	2.557 (3)	176 (4)
C6A—H6A⋯O2B ii	0.93	2.60	3.439 (4)	151

Symmetry codes: (i) ; (ii) .