1-{2-[2-(1H-Benzimidazol-1-yl)eth-oxy]eth-yl}-1H-benzimidazol-3-ium hexa-fluoro-phosphate.

In the title salt, C(18)H(19)N(4)O(+)·PF(6) (-), the dihedral angle between the benzimidazolium and benzimidazole ring systems is 16.24 (2)°. In the cation, a π-π inter-action is observed between the imidazolium ring and the benzene ring of the benzimidazole ring system [centroid-centroid distance = 3.5713 (11) Å]. The PF(6) (-) ion is disordered over two sites, with occupancies of 0.895 (2) and 0.105 (2). In the crystal structure, pairs of N-H⋯N hydrogen bonds link the cations, forming centrosymmetric dimers. The dimers are linked via π-π inter-actions [centroid-centroid distance = 3.5606 (11) Å]. In addition, C-H⋯F hydrogen bonds are observed.

Related literature

For the synthesis, see: Zeng et al. (2008 ▶). For general background to benzimidazole derivatives, see: Pal et al. (2007 ▶); Murru et al. (2009 ▶).

Experimental

Crystal data

C18H19N4O+·PF6 −

M = 452.34

Monoclinic,

a = 10.5347 (18) Å

b = 13.771 (2) Å

c = 13.353 (2) Å

β = 92.507 (2)°

V = 1935.3 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 93 K

0.37 × 0.33 × 0.27 mm

Data collection

Rigaku SPIDER diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.923, T max = 0.943

11885 measured reflections

3959 independent reflections

3445 reflections with I > 2σ(I)

R int = 0.026

Standard reflections: 0

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.080

S = 1.00

3959 reflections

303 parameters

21 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.28 e Å−3

Data collection: RAPID-AUTO (Rigaku/MSC, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810014534/ci5075sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014534/ci5075Isup2.hkl

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

C18H19N4O+·PF6−	F(000) = 928
Mr = 452.34	Dx = 1.553 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5714 reflections
a = 10.5347 (18) Å	θ = 3.1–27.5°
b = 13.771 (2) Å	µ = 0.22 mm−1
c = 13.353 (2) Å	T = 93 K
β = 92.507 (2)°	Block, colourless
V = 1935.3 (6) Å3	0.37 × 0.33 × 0.27 mm
Z = 4

Rigaku SPIDER diffractometer	3959 independent reflections
Radiation source: Rotating Anode	3445 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 26.4°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −13→10
Tmin = 0.923, Tmax = 0.943	k = −13→17
11885 measured reflections	l = −15→16

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0259P)2 + 0.968P] where P = (Fo2 + 2Fc2)/3
3959 reflections	(Δ/σ)max = 0.001
303 parameters	Δρmax = 0.34 e Å−3
21 restraints	Δρmin = −0.28 e Å−3

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. 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 > σ(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)
O1	0.20360 (11)	0.51931 (8)	0.18156 (8)	0.0247 (3)
N1	0.53426 (13)	0.40531 (10)	0.31178 (10)	0.0243 (3)
N2	0.41920 (13)	0.39824 (9)	0.17089 (10)	0.0218 (3)
N3	0.26475 (13)	0.62988 (10)	0.35541 (10)	0.0253 (3)
N4	0.39492 (14)	0.60700 (10)	0.48994 (10)	0.0294 (3)
C1	0.61864 (16)	0.39760 (11)	0.23507 (12)	0.0229 (3)
C2	0.75022 (16)	0.39314 (12)	0.23627 (13)	0.0285 (4)
H2	0.8005	0.3964	0.2970	0.034*
C3	0.80419 (17)	0.38372 (13)	0.14435 (14)	0.0319 (4)
H3	0.8941	0.3801	0.1420	0.038*
C4	0.73059 (17)	0.37927 (13)	0.05438 (13)	0.0311 (4)
H4	0.7718	0.3730	−0.0072	0.037*
C5	0.60018 (16)	0.38377 (12)	0.05330 (12)	0.0262 (4)
H5	0.5499	0.3808	−0.0075	0.031*
C6	0.54567 (15)	0.39293 (11)	0.14572 (12)	0.0218 (3)
C7	0.41753 (16)	0.40521 (11)	0.27069 (12)	0.0245 (4)
H7	0.3424	0.4095	0.3073	0.029*
C8	0.31129 (15)	0.39532 (12)	0.09736 (12)	0.0242 (4)
H8A	0.3030	0.3288	0.0698	0.029*
H8B	0.3286	0.4397	0.0412	0.029*
C9	0.18818 (16)	0.42403 (12)	0.14171 (13)	0.0262 (4)
H9A	0.1185	0.4231	0.0895	0.031*
H9B	0.1668	0.3780	0.1954	0.031*
C10	0.10406 (16)	0.54786 (12)	0.24439 (12)	0.0272 (4)
H10A	0.0890	0.4968	0.2947	0.033*
H10B	0.0243	0.5584	0.2039	0.033*
C11	0.14574 (16)	0.64079 (13)	0.29557 (12)	0.0277 (4)
H11A	0.1568	0.6916	0.2442	0.033*
H11B	0.0783	0.6627	0.3397	0.033*
C12	0.38716 (16)	0.64002 (11)	0.32253 (12)	0.0231 (3)
C13	0.43309 (16)	0.65920 (12)	0.22830 (12)	0.0262 (4)
H13	0.3775	0.6687	0.1712	0.031*
C14	0.56322 (17)	0.66369 (12)	0.22204 (13)	0.0295 (4)
H14	0.5982	0.6764	0.1590	0.035*
C15	0.64530 (18)	0.64993 (12)	0.30653 (14)	0.0314 (4)
H15	0.7345	0.6539	0.2994	0.038*
C16	0.59940 (17)	0.63079 (12)	0.39979 (13)	0.0294 (4)
H16	0.6553	0.6214	0.4567	0.035*
C17	0.46803 (17)	0.62576 (11)	0.40726 (12)	0.0249 (4)
C18	0.27606 (18)	0.61067 (13)	0.45479 (12)	0.0299 (4)
H18	0.2053	0.6008	0.4953	0.036*
P1	−0.07196 (5)	0.71567 (4)	0.57610 (4)	0.02117 (17)	0.8952 (16)
F1	−0.10379 (15)	0.71525 (12)	0.45828 (8)	0.0350 (3)	0.8952 (16)
F2	−0.03912 (12)	0.71374 (11)	0.69440 (8)	0.0393 (4)	0.8952 (16)
F3	0.05729 (13)	0.77151 (12)	0.55925 (10)	0.0540 (4)	0.8952 (16)
F4	−0.19885 (12)	0.65494 (12)	0.59425 (9)	0.0479 (4)	0.8952 (16)
F5	−0.14535 (18)	0.81437 (11)	0.58739 (10)	0.0589 (5)	0.8952 (16)
F6	0.00255 (14)	0.61439 (10)	0.56578 (10)	0.0509 (4)	0.8952 (16)
P1'	−0.0834 (6)	0.7250 (5)	0.5725 (5)	0.141 (8)	0.1048 (16)
F1'	−0.0918 (11)	0.7157 (9)	0.4533 (4)	0.0350 (3)	0.1048 (16)
F2'	−0.0730 (10)	0.7334 (8)	0.6921 (5)	0.0393 (4)	0.1048 (16)
F3'	−0.0180 (10)	0.8283 (6)	0.5636 (8)	0.0540 (4)	0.1048 (16)
F4'	−0.1434 (9)	0.6186 (6)	0.5824 (8)	0.0479 (4)	0.1048 (16)
F5'	−0.2196 (8)	0.7721 (8)	0.5714 (8)	0.0589 (5)	0.1048 (16)
F6'	0.0549 (7)	0.6755 (8)	0.5745 (8)	0.0509 (4)	0.1048 (16)
H1N	0.560 (2)	0.4037 (15)	0.3887 (16)	0.052 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0252 (6)	0.0252 (6)	0.0238 (6)	−0.0009 (5)	0.0013 (5)	−0.0021 (5)
N1	0.0294 (8)	0.0246 (7)	0.0183 (7)	0.0024 (6)	−0.0043 (6)	−0.0007 (6)
N2	0.0255 (7)	0.0219 (7)	0.0177 (6)	0.0001 (6)	−0.0024 (5)	−0.0005 (5)
N3	0.0272 (8)	0.0310 (8)	0.0175 (7)	0.0061 (6)	−0.0033 (6)	−0.0007 (6)
N4	0.0360 (9)	0.0325 (8)	0.0192 (7)	0.0027 (6)	−0.0050 (6)	0.0010 (6)
C1	0.0294 (9)	0.0190 (8)	0.0200 (8)	0.0016 (6)	−0.0023 (7)	−0.0006 (6)
C2	0.0285 (9)	0.0297 (9)	0.0266 (9)	0.0011 (7)	−0.0083 (7)	0.0012 (7)
C3	0.0248 (9)	0.0350 (10)	0.0357 (10)	0.0030 (7)	0.0004 (8)	0.0041 (8)
C4	0.0323 (10)	0.0361 (10)	0.0252 (9)	0.0054 (8)	0.0048 (8)	0.0035 (8)
C5	0.0319 (10)	0.0281 (9)	0.0184 (8)	0.0021 (7)	−0.0026 (7)	0.0003 (7)
C6	0.0246 (9)	0.0180 (8)	0.0225 (8)	0.0011 (6)	−0.0026 (7)	−0.0001 (6)
C7	0.0301 (9)	0.0235 (8)	0.0198 (8)	0.0017 (7)	0.0007 (7)	−0.0002 (7)
C8	0.0261 (9)	0.0254 (9)	0.0204 (8)	−0.0013 (7)	−0.0059 (7)	−0.0011 (7)
C9	0.0259 (9)	0.0268 (9)	0.0255 (9)	−0.0024 (7)	−0.0030 (7)	−0.0015 (7)
C10	0.0230 (9)	0.0346 (10)	0.0240 (9)	0.0024 (7)	0.0012 (7)	0.0020 (7)
C11	0.0249 (9)	0.0357 (10)	0.0222 (8)	0.0076 (7)	−0.0027 (7)	−0.0003 (7)
C12	0.0281 (9)	0.0199 (8)	0.0207 (8)	0.0022 (7)	−0.0044 (7)	−0.0031 (6)
C13	0.0329 (10)	0.0262 (9)	0.0189 (8)	−0.0019 (7)	−0.0055 (7)	−0.0033 (7)
C14	0.0347 (10)	0.0285 (9)	0.0254 (9)	−0.0061 (7)	0.0015 (8)	−0.0051 (7)
C15	0.0288 (10)	0.0287 (9)	0.0362 (10)	−0.0045 (7)	−0.0039 (8)	−0.0048 (8)
C16	0.0332 (10)	0.0246 (9)	0.0294 (9)	−0.0008 (7)	−0.0120 (8)	−0.0027 (7)
C17	0.0325 (9)	0.0202 (8)	0.0212 (8)	0.0013 (7)	−0.0056 (7)	−0.0019 (6)
C18	0.0360 (10)	0.0346 (10)	0.0189 (8)	0.0048 (8)	−0.0004 (7)	0.0013 (7)
P1	0.0156 (3)	0.0302 (3)	0.0175 (4)	−0.0041 (2)	−0.0011 (2)	0.0053 (3)
F1	0.0370 (7)	0.0499 (7)	0.0182 (5)	0.0021 (5)	0.0012 (4)	0.0020 (5)
F2	0.0360 (9)	0.0587 (9)	0.0220 (5)	−0.0174 (6)	−0.0105 (5)	0.0105 (5)
F3	0.0427 (9)	0.0789 (11)	0.0405 (8)	−0.0350 (8)	0.0021 (6)	0.0096 (7)
F4	0.0266 (8)	0.0901 (11)	0.0269 (6)	−0.0273 (7)	−0.0006 (6)	0.0019 (7)
F5	0.0895 (13)	0.0551 (10)	0.0322 (8)	0.0370 (9)	0.0014 (8)	−0.0026 (7)
F6	0.0558 (9)	0.0451 (9)	0.0519 (8)	0.0174 (7)	0.0044 (7)	0.0118 (7)
P1'	0.167 (16)	0.22 (2)	0.030 (7)	−0.026 (15)	−0.032 (8)	0.006 (9)
F1'	0.0370 (7)	0.0499 (7)	0.0182 (5)	0.0021 (5)	0.0012 (4)	0.0020 (5)
F2'	0.0360 (9)	0.0587 (9)	0.0220 (5)	−0.0174 (6)	−0.0105 (5)	0.0105 (5)
F3'	0.0427 (9)	0.0789 (11)	0.0405 (8)	−0.0350 (8)	0.0021 (6)	0.0096 (7)
F4'	0.0266 (8)	0.0901 (11)	0.0269 (6)	−0.0273 (7)	−0.0006 (6)	0.0019 (7)
F5'	0.0895 (13)	0.0551 (10)	0.0322 (8)	0.0370 (9)	0.0014 (8)	−0.0026 (7)
F6'	0.0558 (9)	0.0451 (9)	0.0519 (8)	0.0174 (7)	0.0044 (7)	0.0118 (7)

O1—C9	1.4224 (19)	C10—C11	1.507 (2)
O1—C10	1.4266 (19)	C10—H10A	0.99
N1—C7	1.325 (2)	C10—H10B	0.99
N1—C1	1.389 (2)	C11—H11A	0.99
N1—H1N	1.05 (2)	C11—H11B	0.99
N2—C7	1.337 (2)	C12—C13	1.393 (2)
N2—C6	1.390 (2)	C12—C17	1.400 (2)
N2—C8	1.470 (2)	C13—C14	1.378 (2)
N3—C18	1.353 (2)	C13—H13	0.95
N3—C12	1.387 (2)	C14—C15	1.404 (2)
N3—C11	1.465 (2)	C14—H14	0.95
N4—C18	1.319 (2)	C15—C16	1.381 (3)
N4—C17	1.398 (2)	C15—H15	0.95
C1—C2	1.387 (2)	C16—C17	1.394 (2)
C1—C6	1.392 (2)	C16—H16	0.95
C2—C3	1.381 (2)	C18—H18	0.95
C2—H2	0.95	P1—F5	1.5742 (14)
C3—C4	1.402 (3)	P1—F3	1.5883 (13)
C3—H3	0.95	P1—F1	1.5942 (12)
C4—C5	1.375 (2)	P1—F2	1.6025 (12)
C4—H4	0.95	P1—F4	1.6041 (12)
C5—C6	1.389 (2)	P1—F6	1.6092 (14)
C5—H5	0.95	P1'—F5'	1.574 (3)
C7—H7	0.95	P1'—F3'	1.588 (3)
C8—C9	1.502 (2)	P1'—F1'	1.595 (3)
C8—H8A	0.99	P1'—F2'	1.601 (3)
C8—H8B	0.99	P1'—F4'	1.603 (3)
C9—H9A	0.99	P1'—F6'	1.608 (3)
C9—H9B	0.99
C9—O1—C10	113.54 (12)	C10—C11—H11B	109.1
C7—N1—C1	107.87 (14)	H11A—C11—H11B	107.8
C7—N1—H1N	126.9 (11)	N3—C12—C13	132.02 (15)
C1—N1—H1N	125.0 (11)	N3—C12—C17	105.74 (14)
C7—N2—C6	107.41 (13)	C13—C12—C17	122.24 (16)
C7—N2—C8	128.63 (14)	C14—C13—C12	116.68 (16)
C6—N2—C8	123.95 (13)	C14—C13—H13	121.7
C18—N3—C12	106.67 (14)	C12—C13—H13	121.7
C18—N3—C11	126.26 (15)	C13—C14—C15	121.63 (16)
C12—N3—C11	127.04 (13)	C13—C14—H14	119.2
C18—N4—C17	105.03 (14)	C15—C14—H14	119.2
C2—C1—N1	131.78 (15)	C16—C15—C14	121.52 (17)
C2—C1—C6	121.47 (15)	C16—C15—H15	119.2
N1—C1—C6	106.75 (14)	C14—C15—H15	119.2
C3—C2—C1	116.36 (16)	C15—C16—C17	117.52 (16)
C3—C2—H2	121.8	C15—C16—H16	121.2
C1—C2—H2	121.8	C17—C16—H16	121.2
C2—C3—C4	122.12 (17)	C16—C17—N4	130.48 (16)
C2—C3—H3	118.9	C16—C17—C12	120.41 (16)
C4—C3—H3	118.9	N4—C17—C12	109.11 (15)
C5—C4—C3	121.46 (16)	N4—C18—N3	113.45 (16)
C5—C4—H4	119.3	N4—C18—H18	123.3
C3—C4—H4	119.3	N3—C18—H18	123.3
C4—C5—C6	116.52 (16)	F5—P1—F3	91.33 (10)
C4—C5—H5	121.7	F5—P1—F1	90.84 (8)
C6—C5—H5	121.7	F3—P1—F1	90.37 (7)
C5—C6—N2	131.09 (15)	F5—P1—F2	90.33 (7)
C5—C6—C1	122.08 (15)	F3—P1—F2	89.90 (7)
N2—C6—C1	106.83 (14)	F1—P1—F2	178.79 (8)
N1—C7—N2	111.14 (15)	F5—P1—F4	91.13 (10)
N1—C7—H7	124.4	F3—P1—F4	177.42 (10)
N2—C7—H7	124.4	F1—P1—F4	90.37 (7)
N2—C8—C9	112.67 (13)	F2—P1—F4	89.30 (6)
N2—C8—H8A	109.1	F5—P1—F6	179.35 (8)
C9—C8—H8A	109.1	F3—P1—F6	89.03 (8)
N2—C8—H8B	109.1	F1—P1—F6	89.69 (8)
C9—C8—H8B	109.1	F2—P1—F6	89.14 (8)
H8A—C8—H8B	107.8	F4—P1—F6	88.51 (9)
O1—C9—C8	107.68 (13)	F5'—P1'—F3'	91.6 (3)
O1—C9—H9A	110.2	F5'—P1'—F1'	90.8 (3)
C8—C9—H9A	110.2	F3'—P1'—F1'	90.2 (3)
O1—C9—H9B	110.2	F5'—P1'—F2'	90.1 (3)
C8—C9—H9B	110.2	F3'—P1'—F2'	89.9 (3)
H9A—C9—H9B	108.5	F1'—P1'—F2'	179.1 (4)
O1—C10—C11	107.08 (13)	F5'—P1'—F4'	90.8 (3)
O1—C10—H10A	110.3	F3'—P1'—F4'	177.5 (4)
C11—C10—H10A	110.3	F1'—P1'—F4'	90.2 (3)
O1—C10—H10B	110.3	F2'—P1'—F4'	89.6 (3)
C11—C10—H10B	110.3	F5'—P1'—F6'	179.1 (4)
H10A—C10—H10B	108.6	F3'—P1'—F6'	89.2 (3)
N3—C11—C10	112.69 (14)	F1'—P1'—F6'	89.7 (3)
N3—C11—H11A	109.1	F2'—P1'—F6'	89.5 (3)
C10—C11—H11A	109.1	F4'—P1'—F6'	88.4 (3)
N3—C11—H11B	109.1
C7—N1—C1—C2	−179.03 (17)	C9—O1—C10—C11	169.54 (13)
C7—N1—C1—C6	0.03 (17)	C18—N3—C11—C10	−94.78 (19)
N1—C1—C2—C3	178.85 (16)	C12—N3—C11—C10	87.35 (19)
C6—C1—C2—C3	−0.1 (2)	O1—C10—C11—N3	−58.98 (17)
C1—C2—C3—C4	0.3 (3)	C18—N3—C12—C13	179.45 (17)
C2—C3—C4—C5	−0.2 (3)	C11—N3—C12—C13	−2.3 (3)
C3—C4—C5—C6	0.0 (2)	C18—N3—C12—C17	0.01 (17)
C4—C5—C6—N2	−179.17 (16)	C11—N3—C12—C17	178.22 (15)
C4—C5—C6—C1	0.2 (2)	N3—C12—C13—C14	−179.43 (16)
C7—N2—C6—C5	179.09 (16)	C17—C12—C13—C14	−0.1 (2)
C8—N2—C6—C5	−0.4 (3)	C12—C13—C14—C15	−0.2 (2)
C7—N2—C6—C1	−0.31 (17)	C13—C14—C15—C16	0.3 (3)
C8—N2—C6—C1	−179.76 (13)	C14—C15—C16—C17	−0.1 (2)
C2—C1—C6—C5	−0.1 (2)	C15—C16—C17—N4	179.34 (16)
N1—C1—C6—C5	−179.29 (14)	C15—C16—C17—C12	−0.2 (2)
C2—C1—C6—N2	179.35 (14)	C18—N4—C17—C16	−179.82 (17)
N1—C1—C6—N2	0.17 (17)	C18—N4—C17—C12	−0.29 (18)
C1—N1—C7—N2	−0.23 (18)	N3—C12—C17—C16	179.76 (14)
C6—N2—C7—N1	0.34 (18)	C13—C12—C17—C16	0.3 (2)
C8—N2—C7—N1	179.76 (14)	N3—C12—C17—N4	0.17 (17)
C7—N2—C8—C9	13.2 (2)	C13—C12—C17—N4	−179.34 (14)
C6—N2—C8—C9	−167.43 (14)	C17—N4—C18—N3	0.31 (19)
C10—O1—C9—C8	−167.47 (13)	C12—N3—C18—N4	−0.21 (19)
N2—C8—C9—O1	58.10 (17)	C11—N3—C18—N4	−178.43 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N4i	1.05 (2)	1.68 (2)	2.724 (2)	176 (2)
C4—H4···F3ii	0.95	2.41	3.130 (2)	133
C7—H7···F4iii	0.95	2.23	3.100 (2)	152
C9—H9B···F2iii	0.99	2.40	3.340 (2)	159
C11—H11A···F2iv	0.99	2.51	3.066 (2)	116
C16—H16···F4v	0.95	2.39	3.300 (2)	161
C18—H18···F6	0.95	2.38	3.298 (2)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N4i	1.05 (2)	1.68 (2)	2.724 (2)	176 (2)
C4—H4⋯F3ii	0.95	2.41	3.130 (2)	133
C7—H7⋯F4iii	0.95	2.23	3.100 (2)	152
C9—H9B⋯F2iii	0.99	2.40	3.340 (2)	159
C11—H11A⋯F2iv	0.99	2.51	3.066 (2)	116
C16—H16⋯F4v	0.95	2.39	3.300 (2)	161
C18—H18⋯F6	0.95	2.38	3.298 (2)	163

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