Propane-1,3-diaminium bis-(tetra-fluoro-borate)-18-crown-6 (1/2).

In the title compound, C(3)H(12)N(2) (2+)·2BF(4) (-)·2C(12)H(24)O(6), the central C atom of the propane-1,3-diammonium cation lies on a crystallographic twofold rotation axis. The terminal NH(3) (+) groups insert into the crown rings through strong N-H⋯O hydrogen-bonding inter-actions, resulting in the formation of a 1:2 supra-molecular [(C(3)H(12)N(2))·(C(12)H(24)O(6))(2)](2+) complex. The anions are linked to the supra-molecular complexes via weak C-H⋯F hydrogen bonds. The F atoms of the anion are disordered over two orientations with site occupancies of 0.5.

Related literature

For the structures and properties of a related compounds, see: Fu et al. (2011 ▶); Zhao (2012 ▶) and references therein.

Experimental

Crystal data

C3H12N2 2+·2BF4 −·2C12H24O6

M = 778.39

Monoclinic,

a = 22.615 (5) Å

b = 8.8423 (18) Å

c = 21.077 (4) Å

β = 113.41 (3)°

V = 3867.8 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 298 K

0.10 × 0.05 × 0.05 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.910, T max = 1.000

16100 measured reflections

3413 independent reflections

2018 reflections with I > 2σ(I)

R int = 0.079

Refinement

R[F 2 > 2σ(F 2)] = 0.077

wR(F 2) = 0.212

S = 1.13

3413 reflections

268 parameters

37 restraints

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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 datablock(s) I, global. DOI: 10.1107/S1600536812001572/rz2697sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812001572/rz2697Isup2.hkl

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

C3H12N22+·2BF4−·2C12H24O6	F(000) = 1656
Mr = 778.39	Dx = 1.337 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3410 reflections
a = 22.615 (5) Å	θ = 2.9–27.5°
b = 8.8423 (18) Å	µ = 0.12 mm−1
c = 21.077 (4) Å	T = 298 K
β = 113.41 (3)°	Block, colourless
V = 3867.8 (16) Å3	0.10 × 0.05 × 0.05 mm
Z = 4

Rigaku Mercury2 diffractometer	3413 independent reflections
Radiation source: fine-focus sealed tube	2018 reflections with I > 2σ(I)
graphite	Rint = 0.079
Detector resolution: 13.6612 pixels mm-1	θmax = 25.0°, θmin = 3.0°
CCD profile fitting scans	h = −26→26
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→10
Tmin = 0.910, Tmax = 1.000	l = −25→25
16100 measured reflections

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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.212	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.080P)2 + 3.2068P] where P = (Fo2 + 2Fc2)/3
3413 reflections	(Δ/σ)max < 0.001
268 parameters	Δρmax = 0.31 e Å−3
37 restraints	Δρmin = −0.22 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 > 2sigma(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)
O2	0.19727 (10)	0.6715 (3)	0.26770 (12)	0.0558 (6)
O3	0.15021 (11)	0.7740 (3)	0.12991 (13)	0.0650 (7)
N1	0.10547 (11)	0.9201 (3)	0.23703 (13)	0.0433 (7)
H1A	0.0918	0.9641	0.1957	0.065*
H1B	0.1379	0.8578	0.2419	0.065*
H1C	0.1189	0.9907	0.2698	0.065*
O1	0.22029 (12)	0.8928 (3)	0.37179 (12)	0.0646 (7)
O4	0.07376 (13)	1.0406 (3)	0.09880 (15)	0.0786 (9)
O5	0.10078 (13)	1.2567 (3)	0.20532 (18)	0.0850 (9)
O6	0.14972 (14)	1.1589 (3)	0.34468 (17)	0.0771 (8)
C2	0.25128 (17)	0.6683 (4)	0.3313 (2)	0.0652 (11)
H2A	0.2862	0.7248	0.3269	0.078*
H2B	0.2654	0.5647	0.3431	0.078*
C3	0.21010 (19)	0.5983 (4)	0.2141 (2)	0.0652 (11)
H3A	0.2180	0.4915	0.2244	0.078*
H3B	0.2483	0.6418	0.2112	0.078*
C6	0.0933 (2)	0.9686 (6)	0.0513 (2)	0.0876 (15)
H6A	0.1345	1.0089	0.0555	0.105*
H6B	0.0621	0.9881	0.0047	0.105*
C1	0.2343 (2)	0.7359 (5)	0.3861 (2)	0.0714 (12)
H1D	0.1971	0.6845	0.3879	0.086*
H1E	0.2700	0.7243	0.4306	0.086*
C7	0.0639 (2)	1.2022 (6)	0.0872 (3)	0.0953 (18)
H7A	0.1024	1.2499	0.0868	0.114*
H7B	0.0289	1.2203	0.0427	0.114*
C5	0.0984 (2)	0.8034 (5)	0.06412 (19)	0.0801 (13)
H5A	0.0580	0.7645	0.0633	0.096*
H5B	0.1075	0.7525	0.0282	0.096*
C10	0.1474 (3)	1.3118 (5)	0.3255 (3)	0.0974 (16)
H10A	0.1872	1.3399	0.3215	0.117*
H10B	0.1429	1.3738	0.3613	0.117*
C4	0.1550 (2)	0.6196 (5)	0.1473 (2)	0.0736 (12)
H4A	0.1616	0.5609	0.1118	0.088*
H4B	0.1157	0.5848	0.1509	0.088*
C11	0.2008 (3)	1.1288 (6)	0.4107 (2)	0.0910 (15)
H11A	0.1929	1.1804	0.4472	0.109*
H11B	0.2412	1.1654	0.4106	0.109*
C9	0.0925 (3)	1.3385 (5)	0.2604 (3)	0.0963 (17)
H9A	0.0528	1.3078	0.2641	0.116*
H9B	0.0895	1.4458	0.2499	0.116*
C8	0.0481 (2)	1.2698 (6)	0.1433 (4)	0.1030 (18)
H8A	0.0369	1.3756	0.1333	0.124*
H8B	0.0114	1.2179	0.1462	0.124*
C12	0.2061 (2)	0.9645 (6)	0.4233 (2)	0.0851 (13)
H12A	0.2395	0.9425	0.4684	0.102*
H12B	0.1654	0.9272	0.4224	0.102*
B1	0.0793 (3)	0.6074 (7)	0.4303 (3)	0.0773 (15)
C14	0.0000	0.9285 (5)	0.2500	0.0449 (11)
H14A	0.0184	0.9930	0.2904	0.054*
C13	0.05211 (15)	0.8336 (4)	0.2431 (2)	0.0552 (9)
H13A	0.0699	0.7687	0.2834	0.066*
H13B	0.0330	0.7690	0.2028	0.066*
F2	0.0550 (6)	0.5710 (10)	0.3586 (6)	0.090 (3)	0.50
F3	0.0439 (7)	0.5494 (15)	0.4626 (7)	0.110 (5)	0.50
F4	0.0679 (5)	0.7681 (8)	0.4203 (4)	0.118 (3)	0.50
F1	0.1357 (3)	0.5838 (17)	0.4687 (6)	0.163 (5)	0.50
F1'	0.1185 (8)	0.4723 (15)	0.4546 (6)	0.220 (6)	0.50
F2'	0.0789 (8)	0.5857 (18)	0.3725 (7)	0.172 (7)	0.50
F3'	0.0256 (7)	0.5942 (19)	0.4373 (9)	0.166 (7)	0.50
F4'	0.1152 (8)	0.7196 (18)	0.4632 (7)	0.186 (6)	0.50

	U11	U22	U33	U12	U13	U23
O2	0.0451 (13)	0.0560 (14)	0.0655 (16)	0.0094 (11)	0.0213 (12)	0.0071 (12)
O3	0.0583 (15)	0.0699 (17)	0.0626 (17)	−0.0108 (13)	0.0197 (13)	−0.0076 (13)
N1	0.0392 (14)	0.0452 (15)	0.0476 (15)	0.0051 (12)	0.0196 (12)	0.0064 (12)
O1	0.0721 (17)	0.0758 (17)	0.0456 (14)	−0.0101 (14)	0.0230 (13)	0.0011 (12)
O4	0.0700 (18)	0.088 (2)	0.0635 (18)	−0.0096 (15)	0.0110 (14)	0.0276 (16)
O5	0.0607 (18)	0.0645 (18)	0.128 (3)	0.0193 (14)	0.0355 (18)	0.0222 (17)
O6	0.093 (2)	0.0527 (16)	0.104 (2)	−0.0128 (15)	0.0591 (19)	−0.0153 (15)
C2	0.048 (2)	0.066 (2)	0.071 (3)	0.0021 (18)	0.011 (2)	0.024 (2)
C3	0.074 (3)	0.045 (2)	0.092 (3)	0.0139 (19)	0.049 (2)	0.0021 (19)
C6	0.069 (3)	0.125 (4)	0.045 (2)	−0.035 (3)	−0.002 (2)	0.018 (3)
C1	0.068 (3)	0.074 (3)	0.057 (2)	−0.004 (2)	0.009 (2)	0.027 (2)
C7	0.059 (3)	0.097 (4)	0.088 (3)	−0.019 (2)	−0.015 (2)	0.061 (3)
C5	0.069 (3)	0.112 (4)	0.044 (2)	−0.026 (2)	0.006 (2)	−0.014 (2)
C10	0.113 (4)	0.065 (3)	0.144 (5)	−0.001 (3)	0.083 (4)	−0.027 (3)
C4	0.078 (3)	0.072 (3)	0.081 (3)	−0.009 (2)	0.043 (3)	−0.023 (2)
C11	0.099 (3)	0.111 (4)	0.069 (3)	−0.025 (3)	0.040 (3)	−0.037 (3)
C9	0.100 (4)	0.046 (2)	0.183 (6)	0.021 (3)	0.100 (4)	0.011 (3)
C8	0.066 (3)	0.071 (3)	0.160 (6)	0.007 (2)	0.032 (4)	0.047 (3)
C12	0.087 (3)	0.108 (4)	0.062 (3)	−0.019 (3)	0.032 (2)	−0.012 (3)
B1	0.073 (4)	0.090 (4)	0.087 (4)	−0.020 (3)	0.051 (3)	−0.033 (3)
C14	0.038 (2)	0.038 (2)	0.059 (3)	0.000	0.020 (2)	0.000
C13	0.0443 (18)	0.0430 (18)	0.084 (3)	−0.0031 (16)	0.0320 (18)	−0.0038 (18)
F2	0.118 (7)	0.076 (4)	0.053 (4)	0.018 (4)	0.010 (4)	0.005 (3)
F3	0.155 (12)	0.100 (6)	0.111 (6)	−0.061 (7)	0.091 (7)	−0.012 (4)
F4	0.178 (8)	0.075 (4)	0.099 (5)	−0.020 (4)	0.052 (5)	−0.016 (3)
F1	0.057 (4)	0.207 (10)	0.160 (8)	−0.022 (5)	−0.025 (4)	0.059 (9)
F1'	0.347 (17)	0.195 (9)	0.148 (9)	0.138 (11)	0.131 (10)	0.066 (8)
F2'	0.168 (14)	0.252 (14)	0.091 (8)	0.078 (9)	0.048 (9)	−0.038 (7)
F3'	0.094 (7)	0.203 (15)	0.246 (18)	−0.048 (8)	0.115 (11)	−0.116 (11)
F4'	0.227 (13)	0.193 (9)	0.198 (12)	−0.162 (10)	0.146 (10)	−0.128 (10)

O2—C2	1.410 (4)	C10—C9	1.459 (7)
O2—C3	1.429 (4)	C10—H10A	0.9700
O3—C4	1.407 (5)	C10—H10B	0.9700
O3—C5	1.439 (4)	C4—H4A	0.9698
N1—C13	1.477 (4)	C4—H4B	0.9701
N1—H1A	0.8900	C11—C12	1.473 (7)
N1—H1B	0.8900	C11—H11A	0.9699
N1—H1C	0.8900	C11—H11B	0.9699
O1—C12	1.400 (5)	C9—H9A	0.9699
O1—C1	1.428 (5)	C9—H9B	0.9700
O4—C6	1.397 (6)	C8—H8A	0.9700
O4—C7	1.452 (5)	C8—H8B	0.9700
O5—C8	1.380 (6)	C12—H12A	0.9699
O5—C9	1.442 (6)	C12—H12B	0.9700
O6—C10	1.405 (5)	B1—F1	1.226 (9)
O6—C11	1.436 (6)	B1—F2'	1.228 (15)
C2—C1	1.481 (6)	B1—F3'	1.286 (14)
C2—H2A	0.9701	B1—F4'	1.296 (9)
C2—H2B	0.9700	B1—F3	1.342 (11)
C3—C4	1.475 (6)	B1—F2	1.423 (13)
C3—H3A	0.9699	B1—F4	1.445 (9)
C3—H3B	0.9699	B1—F1'	1.454 (11)
C6—C5	1.482 (6)	C14—C13	1.501 (4)
C6—H6A	0.9701	C14—C13i	1.501 (4)
C6—H6B	0.9700	C14—H14A	0.9700
C1—H1D	0.9701	C13—H13A	0.9701
C1—H1E	0.9699	C13—H13B	0.9700
C7—C8	1.490 (7)	F2—F2'	0.52 (3)
C7—H7A	0.9700	F3—F3'	0.66 (2)
C7—H7B	0.9699	F4—F4'	1.174 (18)
C5—H5A	0.9700	F1—F1'	1.058 (15)
C5—H5B	0.9700	F1—F4'	1.275 (16)
C2—O2—C3	111.8 (3)	O5—C9—C10	110.0 (4)
C4—O3—C5	112.0 (3)	O5—C9—H9A	110.2
C13—N1—H1A	109.5	C10—C9—H9A	110.3
C13—N1—H1B	109.5	O5—C9—H9B	109.1
H1A—N1—H1B	109.5	C10—C9—H9B	109.2
C13—N1—H1C	109.5	H9A—C9—H9B	108.0
H1A—N1—H1C	109.5	O5—C8—C7	109.2 (4)
H1B—N1—H1C	109.5	O5—C8—H8A	109.8
C12—O1—C1	112.1 (3)	C7—C8—H8A	109.7
C6—O4—C7	113.5 (4)	O5—C8—H8B	109.8
C8—O5—C9	112.4 (4)	C7—C8—H8B	109.9
C10—O6—C11	112.4 (4)	H8A—C8—H8B	108.4
O2—C2—C1	109.8 (3)	O1—C12—C11	109.5 (4)
O2—C2—H2A	109.3	O1—C12—H12A	109.9
C1—C2—H2A	109.9	C11—C12—H12A	110.5
O2—C2—H2B	109.6	O1—C12—H12B	109.8
C1—C2—H2B	109.9	C11—C12—H12B	108.8
H2A—C2—H2B	108.3	H12A—C12—H12B	108.4
O2—C3—C4	109.6 (3)	F1—B1—F2'	102.9 (11)
O2—C3—H3A	109.9	F1—B1—F3'	133.6 (11)
C4—C3—H3A	110.5	F2'—B1—F3'	117.7 (12)
O2—C3—H3B	109.6	F1—B1—F4'	60.7 (9)
C4—C3—H3B	109.0	F2'—B1—F4'	114.0 (11)
H3A—C3—H3B	108.1	F3'—B1—F4'	115.3 (10)
O4—C6—C5	110.0 (4)	F1—B1—F3	105.8 (9)
O4—C6—H6A	109.5	F2'—B1—F3	132.3 (11)
C5—C6—H6A	110.0	F4'—B1—F3	113.2 (9)
O4—C6—H6B	109.6	F1—B1—F2	121.6 (10)
C5—C6—H6B	109.4	F3'—B1—F2	96.7 (10)
H6A—C6—H6B	108.2	F4'—B1—F2	129.6 (9)
O1—C1—C2	109.4 (3)	F3—B1—F2	113.3 (9)
O1—C1—H1D	109.9	F1—B1—F4	110.0 (8)
C2—C1—H1D	109.9	F2'—B1—F4	94.5 (9)
O1—C1—H1E	109.6	F3'—B1—F4	89.1 (9)
C2—C1—H1E	109.8	F4'—B1—F4	50.4 (8)
H1D—C1—H1E	108.3	F3—B1—F4	110.0 (8)
O4—C7—C8	109.3 (4)	F2—B1—F4	95.5 (6)
O4—C7—H7A	110.5	F1—B1—F1'	45.5 (7)
C8—C7—H7A	109.4	F2'—B1—F1'	89.1 (9)
O4—C7—H7B	109.7	F3'—B1—F1'	110.9 (11)
C8—C7—H7B	109.8	F4'—B1—F1'	106.0 (12)
H7A—C7—H7B	108.1	F3—B1—F1'	84.9 (9)
O3—C5—C6	109.2 (3)	F2—B1—F1'	96.5 (7)
O3—C5—H5A	110.7	F4—B1—F1'	155.2 (9)
C6—C5—H5A	109.9	C13—C14—C13i	112.0 (4)
O3—C5—H5B	108.9	C13—C14—H14A	109.6
C6—C5—H5B	110.0	C13i—C14—H14A	108.8
H5A—C5—H5B	108.2	N1—C13—C14	114.8 (3)
O6—C10—C9	110.3 (4)	N1—C13—H13A	108.3
O6—C10—H10A	110.0	C14—C13—H13A	108.3
C9—C10—H10A	110.4	N1—C13—H13B	108.9
O6—C10—H10B	108.9	C14—C13—H13B	108.7
C9—C10—H10B	109.0	H13A—C13—H13B	107.6
H10A—C10—H10B	108.1	F2'—F2—B1	58 (3)
O3—C4—C3	108.7 (3)	F3'—F3—B1	70.8 (17)
O3—C4—H4A	109.7	F4'—F4—B1	58.2 (6)
C3—C4—H4A	109.7	F1'—F1—B1	78.7 (9)
O3—C4—H4B	110.6	F1'—F1—F4'	140.6 (13)
C3—C4—H4B	109.7	B1—F1—F4'	62.4 (7)
H4A—C4—H4B	108.5	F1—F1'—B1	55.8 (6)
O6—C11—C12	109.5 (4)	F2—F2'—B1	101 (3)
O6—C11—H11A	110.6	F3—F3'—B1	80 (2)
C12—C11—H11A	110.4	F4—F4'—F1	126.9 (10)
O6—C11—H11B	109.4	F4—F4'—B1	71.4 (8)
C12—C11—H11B	108.6	F1—F4'—B1	57.0 (6)
H11A—C11—H11B	108.2
C3—O2—C2—C1	−176.1 (3)	F4—B1—F1—F1'	−175.3 (10)
C2—O2—C3—C4	−173.6 (3)	F2'—B1—F1—F4'	110.5 (12)
C7—O4—C6—C5	−176.6 (3)	F3'—B1—F1—F4'	−98.1 (14)
C12—O1—C1—C2	−177.8 (3)	F3—B1—F1—F4'	−108.0 (10)
O2—C2—C1—O1	−65.5 (4)	F2—B1—F1—F4'	120.9 (11)
C6—O4—C7—C8	−175.9 (3)	F4—B1—F1—F4'	10.8 (9)
C4—O3—C5—C6	176.1 (4)	F1'—B1—F1—F4'	−173.9 (14)
O4—C6—C5—O3	−66.6 (4)	F4'—F1—F1'—B1	9(2)
C11—O6—C10—C9	−176.4 (4)	F2'—B1—F1'—F1	109.2 (14)
C5—O3—C4—C3	178.3 (3)	F3'—B1—F1'—F1	−131.3 (15)
O2—C3—C4—O3	66.2 (4)	F4'—B1—F1'—F1	−5.5 (13)
C10—O6—C11—C12	−172.4 (4)	F3—B1—F1'—F1	−118.2 (13)
C8—O5—C9—C10	175.9 (4)	F2—B1—F1'—F1	128.9 (12)
O6—C10—C9—O5	−65.0 (5)	F4—B1—F1'—F1	10 (2)
C9—O5—C8—C7	171.7 (3)	F1—B1—F2'—F2	155 (3)
O4—C7—C8—O5	65.7 (4)	F3'—B1—F2'—F2	−2(3)
C1—O1—C12—C11	172.4 (3)	F4'—B1—F2'—F2	−142 (3)
O6—C11—C12—O1	60.6 (5)	F3—B1—F2'—F2	29 (3)
C13i—C14—C13—N1	−179.2 (4)	F4—B1—F2'—F2	−94 (3)
F1—B1—F2—F2'	−29 (3)	F1'—B1—F2'—F2	111 (3)
F3'—B1—F2—F2'	178 (3)	F1—B1—F3'—F3	−20 (4)
F4'—B1—F2—F2'	47 (3)	F2'—B1—F3'—F3	128 (3)
F3—B1—F2—F2'	−157 (3)	F4'—B1—F3'—F3	−93 (3)
F4—B1—F2—F2'	88 (3)	F2—B1—F3'—F3	127 (3)
F1'—B1—F2—F2'	−70 (3)	F4—B1—F3'—F3	−137 (3)
F1—B1—F3—F3'	165 (3)	F1'—B1—F3'—F3	28 (3)
F2'—B1—F3—F3'	−70 (3)	B1—F4—F4'—F1	13.8 (11)
F4'—B1—F3—F3'	101 (3)	F1'—F1—F4'—F4	−25 (3)
F2—B1—F3—F3'	−59 (3)	B1—F1—F4'—F4	−15.7 (12)
F4—B1—F3—F3'	46 (3)	F1'—F1—F4'—B1	−9(2)
F1'—B1—F3—F3'	−154 (3)	F1—B1—F4'—F4	166.8 (11)
F1—B1—F4—F4'	−12.2 (10)	F2'—B1—F4'—F4	75.1 (12)
F2'—B1—F4—F4'	−117.7 (11)	F3'—B1—F4'—F4	−65.6 (13)
F3'—B1—F4—F4'	124.6 (11)	F3—B1—F4'—F4	−97.4 (11)
F3—B1—F4—F4'	104.0 (11)	F2—B1—F4'—F4	58.4 (14)
F2—B1—F4—F4'	−138.8 (9)	F1'—B1—F4'—F4	171.4 (9)
F1'—B1—F4—F4'	−20.1 (19)	F2'—B1—F4'—F1	−91.7 (13)
F2'—B1—F1—F1'	−75.6 (13)	F3'—B1—F4'—F1	127.6 (13)
F3'—B1—F1—F1'	76 (2)	F3—B1—F4'—F1	95.7 (11)
F4'—B1—F1—F1'	173.9 (14)	F2—B1—F4'—F1	−108.4 (14)
F3—B1—F1—F1'	65.9 (14)	F4—B1—F4'—F1	−166.8 (11)
F2—B1—F1—F1'	−65.2 (12)	F1'—B1—F4'—F1	4.5 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2	0.89	2.06	2.915 (3)	161
N1—H1A···O4	0.89	2.03	2.911 (4)	169
N1—H1C···O6	0.89	2.08	2.967 (4)	179
C12—H12B···F4'	0.97	2.48	3.316 (19)	144
C13—H13A···F2	0.97	2.47	3.346 (12)	150
C13—H13A···F2'	0.97	2.42	3.361 (16)	162
C5—H5A···F3'ii	0.97	2.41	3.350 (18)	162
C10—H10B···F1'iii	0.97	2.41	3.355 (17)	166
C10—H10B···F2'iii	0.97	2.44	3.235 (19)	139
C8—H8A···F3'iv	0.97	2.50	3.412 (14)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O2	0.89	2.06	2.915 (3)	161
N1—H1A⋯O4	0.89	2.03	2.911 (4)	169
N1—H1C⋯O6	0.89	2.08	2.967 (4)	179
C12—H12B⋯F4′	0.97	2.48	3.316 (19)	144
C13—H13A⋯F2	0.97	2.47	3.346 (12)	150
C13—H13A⋯F2′	0.97	2.42	3.361 (16)	162
C5—H5A⋯F3′i	0.97	2.41	3.350 (18)	162
C10—H10B⋯F1′ii	0.97	2.41	3.355 (17)	166
C10—H10B⋯F2′ii	0.97	2.44	3.235 (19)	139
C8—H8A⋯F3′iii	0.97	2.50	3.412 (14)	156

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