1,1'-[(1,3-Dihydroxypropane-2,2-diyl)dimethylene]dipyridinium bis-(hexa-fluoro-phosphate).

The title compound, C(15)H(20)N(2)O(2) (2+)·2PF(6) (-), was prepared by anion exchange of two bromide ions in the ionic liquid 2,2'-bis-(pyridinium-1-ylmeth-yl)-propane-1,3-diol dibromide with potassium hexa-fluoro-phosphate. The two pyridine rings are planar (r.m.s. deviations = 0.008 and 0.00440 Å) and make a dihedral angle of 44.0 (2)°. Intermolecular O-H⋯F and C-H⋯F interactions occur. The four F atoms in each anion were refined as disordered over two sets of sites with an occupancy ration of 0.700 (19):0.300 (19).

Related literature

For properties and applications of ionic liquids, see: Welton (1999 ▶). For dicationic ionic liquids, see: Liang et al. (2008 ▶); Geng et al. (2010 ▶); Yuan et al. (2010 ▶); Yang et al. (2010 ▶). For the synthesis of dicationic ionic liquids, see: Yuan et al. (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H20N2O2 2+·2PF6 −

M = 550.27

Monoclinic,

a = 11.955 (2) Å

b = 13.796 (3) Å

c = 12.707 (3) Å

β = 95.17 (3)°

V = 2087.3 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.907, T max = 0.968

4027 measured reflections

3835 independent reflections

2564 reflections with I > 2σ(I)

R int = 0.031

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.141

S = 1.04

3835 reflections

372 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo,1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811013080/im2266sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013080/im2266Isup2.hkl

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

C15H20N2O22+·2PF6−	F(000) = 1112
Mr = 550.27	Dx = 1.751 Mg m−3
Monoclinic, P21/n	Melting point = 508–510 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 11.955 (2) Å	Cell parameters from 25 reflections
b = 13.796 (3) Å	θ = 9–13°
c = 12.707 (3) Å	µ = 0.33 mm−1
β = 95.17 (3)°	T = 293 K
V = 2087.3 (7) Å3	Block, colorless
Z = 4	0.30 × 0.20 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	2564 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
graphite	θmax = 25.4°, θmin = 2.2°
ω/2θ scans	h = 0→14
Absorption correction: ψ scan (North et al., 1968)	k = 0→16
Tmin = 0.907, Tmax = 0.968	l = −15→15
4027 measured reflections	3 standard reflections every 200 reflections
3835 independent reflections	intensity decay: 1%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053	H-atom parameters constrained
wR(F2) = 0.141	w = 1/[σ2(Fo2) + (0.0676P)2 + 0.894P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3835 reflections	Δρmax = 0.36 e Å−3
372 parameters	Δρmin = −0.26 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0115 (12)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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)
C1	0.7687 (3)	0.3662 (2)	0.7039 (3)	0.0524 (8)
H1B	0.8189	0.3301	0.6679	0.063*
C2	0.6564 (3)	0.3615 (3)	0.6737 (3)	0.0634 (10)
H2B	0.6302	0.3240	0.6158	0.076*
C3	0.5825 (3)	0.4116 (3)	0.7286 (3)	0.0684 (11)
H3A	0.5056	0.4069	0.7100	0.082*
C4	0.6229 (3)	0.4692 (3)	0.8114 (3)	0.0659 (10)
H4A	0.5738	0.5046	0.8492	0.079*
C5	0.7352 (3)	0.4739 (3)	0.8378 (3)	0.0523 (8)
H5A	0.7630	0.5135	0.8934	0.063*
C6	0.9277 (3)	0.4206 (2)	0.8207 (2)	0.0443 (7)
H6A	0.9569	0.3568	0.8060	0.053*
H6B	0.9362	0.4296	0.8967	0.053*
C7	0.9999 (2)	0.4972 (2)	0.7698 (2)	0.0366 (7)
C8	0.9657 (3)	0.5992 (2)	0.7975 (3)	0.0491 (8)
H8A	1.0165	0.6459	0.7703	0.059*
H8B	0.8903	0.6127	0.7662	0.059*
C9	0.9929 (3)	0.4856 (2)	0.6495 (2)	0.0457 (8)
H9A	0.9157	0.4930	0.6198	0.055*
H9B	1.0380	0.5349	0.6191	0.055*
C10	1.1185 (2)	0.4719 (2)	0.8195 (2)	0.0416 (7)
H10A	1.1182	0.4741	0.8958	0.050*
H10B	1.1355	0.4058	0.8004	0.050*
C11	1.2419 (3)	0.6103 (2)	0.8503 (3)	0.0504 (8)
H11A	1.2049	0.6237	0.9100	0.060*
C12	1.3296 (3)	0.6672 (3)	0.8268 (3)	0.0621 (10)
H12A	1.3531	0.7187	0.8706	0.074*
C13	1.3824 (3)	0.6479 (3)	0.7383 (3)	0.0649 (10)
H13A	1.4421	0.6862	0.7213	0.078*
C14	1.3471 (3)	0.5719 (3)	0.6748 (3)	0.0609 (10)
H14A	1.3821	0.5587	0.6140	0.073*
C15	1.2606 (3)	0.5161 (2)	0.7011 (3)	0.0496 (8)
H15A	1.2369	0.4639	0.6584	0.060*
F1	0.8561 (10)	0.3151 (7)	0.4690 (8)	0.077 (2)	0.700 (19)
F2	0.8566 (7)	0.0817 (6)	0.4416 (8)	0.095 (2)	0.700 (19)
F3	0.7337 (10)	0.1917 (9)	0.4717 (10)	0.111 (4)	0.700 (19)
F4	0.9805 (9)	0.2016 (13)	0.4446 (10)	0.156 (5)	0.700 (19)
F1'	0.886 (3)	0.3061 (18)	0.448 (2)	0.107 (10)	0.300 (19)
F2'	0.867 (3)	0.0966 (17)	0.4638 (19)	0.174 (13)	0.300 (19)
F3'	0.742 (2)	0.2191 (19)	0.455 (3)	0.111 (8)	0.300 (19)
F4'	1.0133 (16)	0.1966 (19)	0.4436 (13)	0.083 (4)	0.300 (19)
F5	0.8379 (3)	0.2040 (2)	0.33183 (18)	0.1135 (10)
F6	0.8902 (3)	0.19322 (18)	0.57857 (18)	0.1019 (9)
F7	0.7615 (12)	0.6122 (8)	0.5469 (9)	0.134 (4)	0.700 (19)
F8	0.5398 (6)	0.7270 (5)	0.5386 (7)	0.087 (2)	0.700 (19)
F9	0.5816 (5)	0.5722 (6)	0.5350 (8)	0.079 (2)	0.700 (19)
F10	0.7152 (4)	0.7742 (5)	0.5546 (4)	0.0600 (16)	0.700 (19)
F7'	0.783 (3)	0.620 (3)	0.5484 (16)	0.144 (13)	0.300 (19)
F8'	0.5348 (13)	0.701 (2)	0.5434 (19)	0.152 (11)	0.300 (19)
F9'	0.631 (4)	0.558 (2)	0.535 (2)	0.211 (15)	0.300 (19)
F10'	0.710 (2)	0.7468 (16)	0.5498 (16)	0.178 (15)	0.300 (19)
F11	0.6508 (2)	0.67341 (18)	0.41995 (16)	0.0884 (8)
F12	0.6571 (2)	0.6637 (2)	0.66872 (17)	0.0994 (9)
N1	0.8068 (2)	0.42241 (18)	0.78490 (19)	0.0401 (6)
N2	1.2088 (2)	0.53542 (17)	0.78851 (19)	0.0391 (6)
O1	0.9697 (2)	0.60654 (18)	0.91006 (18)	0.0683 (7)
H1A	0.9511	0.6613	0.9264	0.102*
O2	1.0330 (2)	0.39234 (18)	0.62617 (18)	0.0614 (7)
H2A	1.0300	0.3852	0.5619	0.092*
P1	0.86380 (8)	0.19842 (7)	0.45439 (7)	0.0540 (3)
P2	0.65577 (8)	0.66706 (6)	0.54479 (6)	0.0474 (3)

	U11	U22	U33	U12	U13	U23
C1	0.061 (2)	0.0469 (19)	0.050 (2)	−0.0083 (17)	0.0084 (16)	−0.0058 (16)
C2	0.065 (3)	0.060 (2)	0.063 (2)	−0.017 (2)	−0.0047 (19)	−0.0065 (19)
C3	0.049 (2)	0.069 (3)	0.085 (3)	−0.007 (2)	−0.005 (2)	0.012 (2)
C4	0.055 (2)	0.071 (3)	0.073 (3)	0.006 (2)	0.0133 (19)	0.003 (2)
C5	0.056 (2)	0.055 (2)	0.0466 (19)	0.0023 (17)	0.0099 (16)	0.0003 (16)
C6	0.0475 (19)	0.0442 (18)	0.0407 (17)	0.0027 (15)	0.0015 (14)	0.0090 (14)
C7	0.0403 (17)	0.0352 (16)	0.0338 (15)	−0.0004 (13)	0.0009 (12)	0.0023 (12)
C8	0.053 (2)	0.0432 (19)	0.050 (2)	0.0045 (15)	0.0001 (15)	0.0020 (15)
C9	0.0509 (19)	0.051 (2)	0.0345 (16)	−0.0036 (15)	−0.0014 (14)	0.0063 (14)
C10	0.0473 (18)	0.0388 (17)	0.0377 (16)	−0.0003 (14)	−0.0014 (13)	0.0045 (13)
C11	0.054 (2)	0.052 (2)	0.0449 (19)	−0.0033 (16)	0.0038 (15)	−0.0099 (15)
C12	0.055 (2)	0.060 (2)	0.071 (3)	−0.0092 (18)	0.0026 (19)	−0.0154 (19)
C13	0.049 (2)	0.058 (2)	0.089 (3)	−0.0039 (18)	0.015 (2)	0.006 (2)
C14	0.051 (2)	0.071 (3)	0.063 (2)	0.0043 (19)	0.0186 (18)	−0.001 (2)
C15	0.048 (2)	0.054 (2)	0.0475 (19)	0.0074 (16)	0.0065 (15)	−0.0106 (16)
F1	0.109 (5)	0.053 (3)	0.066 (4)	0.004 (3)	−0.012 (4)	0.003 (2)
F2	0.141 (5)	0.050 (3)	0.088 (5)	0.010 (3)	−0.032 (3)	−0.037 (3)
F3	0.079 (4)	0.123 (8)	0.137 (6)	−0.047 (5)	0.039 (4)	−0.036 (6)
F4	0.027 (5)	0.255 (9)	0.188 (7)	0.012 (5)	0.012 (4)	−0.044 (6)
F1'	0.15 (2)	0.068 (11)	0.107 (14)	−0.060 (13)	0.004 (11)	−0.009 (8)
F2'	0.40 (3)	0.052 (9)	0.055 (8)	−0.032 (11)	−0.054 (11)	−0.024 (7)
F3'	0.058 (11)	0.084 (11)	0.194 (18)	0.014 (10)	0.019 (10)	0.027 (10)
F4'	0.014 (8)	0.159 (11)	0.076 (7)	0.005 (7)	0.009 (5)	−0.018 (6)
F5	0.157 (3)	0.137 (3)	0.0422 (14)	0.001 (2)	−0.0148 (15)	−0.0030 (14)
F6	0.180 (3)	0.0738 (16)	0.0473 (14)	0.0147 (17)	−0.0141 (15)	−0.0025 (11)
F7	0.088 (6)	0.116 (6)	0.196 (9)	0.047 (4)	−0.005 (5)	−0.029 (5)
F8	0.100 (6)	0.066 (3)	0.094 (4)	0.035 (3)	0.009 (3)	−0.011 (2)
F9	0.095 (4)	0.056 (4)	0.087 (4)	−0.028 (2)	0.010 (2)	−0.005 (3)
F10	0.088 (3)	0.043 (3)	0.050 (2)	−0.032 (2)	0.0108 (17)	−0.0115 (18)
F7'	0.085 (12)	0.27 (3)	0.083 (11)	0.101 (15)	0.022 (8)	0.049 (13)
F8'	0.034 (8)	0.29 (3)	0.130 (14)	−0.055 (12)	0.014 (7)	0.024 (15)
F9'	0.47 (5)	0.050 (9)	0.121 (15)	−0.05 (2)	0.08 (3)	−0.008 (8)
F10'	0.35 (4)	0.089 (12)	0.075 (8)	−0.151 (17)	0.050 (11)	−0.032 (7)
F11	0.131 (2)	0.0975 (18)	0.0378 (12)	−0.0269 (16)	0.0152 (12)	−0.0127 (11)
F12	0.151 (2)	0.109 (2)	0.0386 (13)	−0.0268 (18)	0.0083 (13)	0.0125 (12)
N1	0.0438 (15)	0.0395 (14)	0.0369 (13)	−0.0014 (12)	0.0040 (11)	0.0062 (11)
N2	0.0394 (14)	0.0395 (14)	0.0378 (14)	0.0011 (11)	−0.0003 (11)	−0.0022 (11)
O1	0.094 (2)	0.0608 (16)	0.0497 (15)	0.0114 (14)	0.0054 (13)	−0.0156 (12)
O2	0.0687 (16)	0.0663 (17)	0.0485 (14)	0.0037 (13)	0.0019 (12)	−0.0185 (12)
P1	0.0626 (7)	0.0553 (6)	0.0426 (5)	−0.0065 (5)	−0.0043 (4)	−0.0053 (4)
P2	0.0626 (6)	0.0428 (5)	0.0374 (5)	−0.0009 (4)	0.0071 (4)	−0.0009 (4)

C1—N1	1.336 (4)	C12—C13	1.365 (5)
C1—C2	1.364 (5)	C12—H12A	0.9300
C1—H1B	0.9300	C13—C14	1.365 (5)
C2—C3	1.362 (6)	C13—H13A	0.9300
C2—H2B	0.9300	C14—C15	1.355 (5)
C3—C4	1.372 (6)	C14—H14A	0.9300
C3—H3A	0.9300	C15—N2	1.346 (4)
C4—C5	1.356 (5)	C15—H15A	0.9300
C4—H4A	0.9300	F1—P1	1.624 (10)
C5—N1	1.339 (4)	F2—P1	1.620 (9)
C5—H5A	0.9300	F3—P1	1.593 (12)
C6—N1	1.476 (4)	F4—P1	1.412 (10)
C6—C7	1.542 (4)	F1'—P1	1.51 (2)
C6—H6A	0.9700	F2'—P1	1.41 (2)
C6—H6B	0.9700	F3'—P1	1.49 (2)
C7—C8	1.516 (4)	F4'—P1	1.805 (18)
C7—C9	1.532 (4)	F5—P1	1.562 (2)
C7—C10	1.539 (4)	F6—P1	1.583 (2)
C8—O1	1.430 (4)	F7—P2	1.471 (12)
C8—H8A	0.9700	F8—P2	1.610 (6)
C8—H8B	0.9700	F9—P2	1.580 (8)
C9—O2	1.414 (4)	F10—P2	1.639 (7)
C9—H9A	0.9700	F7'—P2	1.65 (3)
C9—H9B	0.9700	F8'—P2	1.517 (19)
C10—N2	1.472 (4)	F9'—P2	1.54 (3)
C10—H10A	0.9700	F10'—P2	1.276 (19)
C10—H10B	0.9700	F11—P2	1.585 (2)
C11—N2	1.336 (4)	F12—P2	1.574 (2)
C11—C12	1.364 (5)	O1—H1A	0.8200
C11—H11A	0.9300	O2—H2A	0.8200
N1—C1—C2	120.2 (3)	C13—C14—H14A	120.2
N1—C1—H1B	119.9	N2—C15—C14	120.6 (3)
C2—C1—H1B	119.9	N2—C15—H15A	119.7
C3—C2—C1	119.9 (4)	C14—C15—H15A	119.7
C3—C2—H2B	120.0	C1—N1—C5	120.4 (3)
C1—C2—H2B	120.0	C1—N1—C6	118.9 (3)
C2—C3—C4	119.2 (4)	C5—N1—C6	120.5 (3)
C2—C3—H3A	120.4	C11—N2—C15	120.3 (3)
C4—C3—H3A	120.4	C11—N2—C10	119.3 (3)
C5—C4—C3	119.4 (4)	C15—N2—C10	120.4 (3)
C5—C4—H4A	120.3	C8—O1—H1A	109.5
C3—C4—H4A	120.3	C9—O2—H2A	109.5
N1—C5—C4	120.9 (3)	F2'—P1—F3'	102.4 (17)
N1—C5—H5A	119.5	F2'—P1—F1'	168.1 (19)
C4—C5—H5A	119.5	F3'—P1—F1'	89.3 (15)
N1—C6—C7	115.4 (2)	F2'—P1—F5	97.8 (10)
N1—C6—H6A	108.4	F4—P1—F5	91.1 (5)
C7—C6—H6A	108.4	F4—P1—F6	88.8 (5)
N1—C6—H6B	108.4	F5—P1—F6	179.74 (18)
C7—C6—H6B	108.4	F4—P1—F3	176.7 (8)
H6A—C6—H6B	107.5	F5—P1—F3	91.9 (5)
C8—C7—C9	109.6 (2)	F6—P1—F3	88.2 (5)
C8—C7—C10	111.9 (2)	F4—P1—F2	93.8 (8)
C9—C7—C10	110.6 (2)	F5—P1—F2	86.9 (4)
C8—C7—C6	111.5 (3)	F6—P1—F2	93.4 (4)
C9—C7—C6	111.3 (2)	F3—P1—F2	85.0 (5)
C10—C7—C6	101.7 (2)	F4—P1—F1	92.6 (8)
O1—C8—C7	108.2 (2)	F5—P1—F1	93.2 (4)
O1—C8—H8A	110.1	F6—P1—F1	86.5 (4)
C7—C8—H8A	110.1	F3—P1—F1	88.6 (6)
O1—C8—H8B	110.1	F2—P1—F1	173.6 (5)
C7—C8—H8B	110.1	F2'—P1—F4'	88.2 (16)
H8A—C8—H8B	108.4	F3'—P1—F4'	168.9 (13)
O2—C9—C7	108.4 (2)	F1'—P1—F4'	80.2 (15)
O2—C9—H9A	110.0	F10'—P2—F8'	102.6 (19)
C7—C9—H9A	110.0	F10'—P2—F9'	160 (3)
O2—C9—H9B	110.0	F8'—P2—F9'	96.8 (16)
C7—C9—H9B	110.0	F7—P2—F12	92.0 (5)
H9A—C9—H9B	108.4	F7—P2—F9	92.9 (7)
N2—C10—C7	115.2 (2)	F12—P2—F9	90.6 (4)
N2—C10—H10A	108.5	F7—P2—F11	90.1 (5)
C7—C10—H10A	108.5	F12—P2—F11	177.84 (16)
N2—C10—H10B	108.5	F9—P2—F11	89.8 (4)
C7—C10—H10B	108.5	F7—P2—F8	178.3 (6)
H10A—C10—H10B	107.5	F12—P2—F8	89.7 (3)
N2—C11—C12	120.6 (3)	F9—P2—F8	86.9 (4)
N2—C11—H11A	119.7	F11—P2—F8	88.2 (3)
C12—C11—H11A	119.7	F7—P2—F10	95.5 (6)
C11—C12—C13	119.3 (3)	F12—P2—F10	89.1 (2)
C11—C12—H12A	120.4	F9—P2—F10	171.5 (3)
C13—C12—H12A	120.4	F11—P2—F10	90.2 (2)
C14—C13—C12	119.7 (3)	F8—P2—F10	84.6 (3)
C14—C13—H13A	120.1	F10'—P2—F7'	82.6 (18)
C12—C13—H13A	120.1	F8'—P2—F7'	174.6 (16)
C15—C14—C13	119.5 (3)	F9'—P2—F7'	78 (2)
C15—C14—H14A	120.2
N1—C1—C2—C3	−2.2 (6)	N2—C11—C12—C13	1.0 (5)
C1—C2—C3—C4	2.3 (6)	C11—C12—C13—C14	−0.1 (6)
C2—C3—C4—C5	−0.8 (6)	C12—C13—C14—C15	−0.6 (6)
C3—C4—C5—N1	−0.8 (6)	C13—C14—C15—N2	0.6 (5)
N1—C6—C7—C8	63.2 (3)	C2—C1—N1—C5	0.6 (5)
N1—C6—C7—C9	−59.6 (3)	C2—C1—N1—C6	175.6 (3)
N1—C6—C7—C10	−177.4 (2)	C4—C5—N1—C1	0.9 (5)
C9—C7—C8—O1	178.2 (2)	C4—C5—N1—C6	−174.0 (3)
C10—C7—C8—O1	−58.7 (3)	C7—C6—N1—C1	92.4 (3)
C6—C7—C8—O1	54.4 (3)	C7—C6—N1—C5	−92.7 (3)
C8—C7—C9—O2	175.8 (2)	C12—C11—N2—C15	−1.0 (5)
C10—C7—C9—O2	51.9 (3)	C12—C11—N2—C10	176.3 (3)
C6—C7—C9—O2	−60.4 (3)	C14—C15—N2—C11	0.2 (5)
C8—C7—C10—N2	−59.2 (3)	C14—C15—N2—C10	−177.1 (3)
C9—C7—C10—N2	63.4 (3)	C7—C10—N2—C11	95.2 (3)
C6—C7—C10—N2	−178.3 (2)	C7—C10—N2—C15	−87.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6B···O1	0.97	2.47	2.831 (5)	102
C10—H10B···O2	0.97	2.44	2.796 (5)	102
O1—H1A···F8i	0.82	2.29	2.898 (8)	131
O2—H2A···F1	0.82	2.49	2.973 (11)	119
C1—H1B···F6	0.93	2.40	3.280 (4)	158
C11—H11A···F10i	0.93	2.31	3.087 (7)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6B⋯O1	0.97	2.47	2.831 (5)	102
C10—H10B⋯O2	0.97	2.44	2.796 (5)	102
O1—H1A⋯F8i	0.82	2.29	2.898 (8)	131
O2—H2A⋯F1	0.82	2.49	2.973 (11)	119
C1—H1B⋯F6	0.93	2.40	3.280 (4)	158
C11—H11A⋯F10i	0.93	2.31	3.087 (7)	141

Symmetry code: (i) .