1,1'-(Hexane-1,6-di-yl)dipyridinium bis-(hexa-fluoro-phosphate).

The asymmetric unit of the title compound, C(16)H(22)N(2) (2+)·2PF(6) (-), contains one half-mol-ecule and a hexa-fluoro-phosphate anion. In the crystal structure, inter-molecular C-H⋯F hydrogen bonds link the mol-ecules. The F atoms in the hexa-fluoro-phosphate anion are disordered over two positions and were refined with occupancies of 0.43 (2) and 0.57 (2).

Related literature

For general background, see: Jared et al. (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H22N2 2+·2PF6 −

M = 532.30 (3)

Triclinic,

a = 7.9140 (16) Å

b = 9.2930 (18) Å

c = 9.4870 (19) Å

α = 65.13 (3)°

β = 65.46 (3)°

γ = 74.37 (3)°

V = 572.0 (3) Å3

Z = 1

Mo Kα radiation

μ = 0.29 mm−1

T = 298 (2) K

0.30 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.917, T max = 0.944

2172 measured reflections

2014 independent reflections

1499 reflections with I > 2σ(I)

R int = 0.047

3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.166

S = 1.00

2014 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; 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 I, global, x1. DOI: 10.1107/S1600536808039639/hk2581sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039639/hk2581Isup2.hkl

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

C16H22N22+·2P1F6–	Z = 1
Mr = 532.30 (3)	F000 = 270
Triclinic, P1	Dx = 1.545 Mg m−3
Hall symbol: -P 1	Melting point: 513 K
a = 7.9140 (16) Å	Mo Kα radiation λ = 0.71073 Å
b = 9.2930 (18) Å	Cell parameters from 25 reflections
c = 9.4870 (19) Å	θ = 10–12º
α = 65.13 (3)º	µ = 0.29 mm−1
β = 65.46 (3)º	T = 298 (2) K
γ = 74.37 (3)º	Block, colorless
V = 572.0 (3) Å3	0.30 × 0.30 × 0.20 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.047
Radiation source: fine-focus sealed tube	θmax = 25.1º
Monochromator: graphite	θmin = 2.4º
T = 298(2) K	h = −8→9
ω/2θ scans	k = −9→10
Absorption correction: ψ scan(North et al., 1968)	l = 0→11
Tmin = 0.917, Tmax = 0.944	3 standard reflections
2172 measured reflections	every 120 min
2014 independent reflections	intensity decay: none
1499 reflections with I > 2σ(I)

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)] = 0.065	H-atom parameters constrained
wR(F2) = 0.166	w = 1/[σ2(Fo2) + (0.06P)2 + 0.95P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2014 reflections	Δρmax = 0.30 e Å−3
200 parameters	Δρmin = −0.38 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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)
P	0.16995 (14)	0.79005 (13)	0.78487 (13)	0.0539 (4)
N	0.6355 (4)	0.7536 (4)	0.2462 (4)	0.0472 (8)
F1	−0.006 (3)	0.696 (3)	0.842 (2)	0.156 (6)	0.43 (2)
F2	0.369 (2)	0.8457 (19)	0.721 (2)	0.104 (5)	0.43 (2)
F3	0.034 (2)	0.8894 (16)	0.8982 (15)	0.091 (4)	0.43 (2)
F4	0.215 (2)	0.645 (2)	0.939 (2)	0.076 (4)	0.43 (2)
F5	0.126 (2)	0.936 (2)	0.635 (2)	0.078 (4)	0.43 (2)
F6	0.223 (3)	0.677 (3)	0.684 (2)	0.076 (4)	0.43 (2)
F1'	−0.0338 (9)	0.7809 (16)	0.8155 (14)	0.118 (4)	0.57 (2)
F2'	0.375 (2)	0.785 (2)	0.775 (2)	0.144 (5)	0.57 (2)
F3'	0.127 (2)	0.9036 (12)	0.8910 (13)	0.098 (3)	0.57 (2)
F4'	0.150 (2)	0.6338 (18)	0.9501 (17)	0.090 (4)	0.57 (2)
F5'	0.195 (2)	0.9495 (17)	0.6211 (17)	0.094 (4)	0.57 (2)
F6'	0.2820 (19)	0.6854 (19)	0.6687 (18)	0.082 (4)	0.57 (2)
C1	0.6255 (6)	0.6893 (5)	0.1468 (5)	0.0607 (11)
H1A	0.7227	0.6159	0.1113	0.073*
C2	0.4732 (7)	0.7312 (6)	0.0972 (6)	0.0735 (13)
H2A	0.4661	0.6866	0.0288	0.088*
C3	0.3292 (6)	0.8420 (6)	0.1517 (6)	0.0751 (14)
H3A	0.2260	0.8736	0.1179	0.090*
C4	0.3402 (6)	0.9030 (6)	0.2537 (6)	0.0721 (13)
H4A	0.2428	0.9751	0.2913	0.087*
C5	0.4934 (5)	0.8603 (5)	0.3029 (5)	0.0543 (10)
H5A	0.5003	0.9029	0.3730	0.065*
C6	0.7977 (5)	0.7070 (5)	0.3014 (5)	0.0580 (10)
H6A	0.8387	0.8022	0.2896	0.070*
H6B	0.8998	0.6558	0.2307	0.070*
C7	0.7536 (5)	0.5942 (5)	0.4801 (5)	0.0563 (10)
H7A	0.7184	0.4969	0.4908	0.068*
H7B	0.6475	0.6434	0.5502	0.068*
C8	0.9189 (5)	0.5519 (5)	0.5406 (5)	0.0602 (11)
H8A	0.9628	0.6498	0.5183	0.072*
H8B	0.8761	0.4963	0.6595	0.072*

	U11	U22	U33	U12	U13	U23
P	0.0470 (6)	0.0550 (6)	0.0538 (6)	0.0051 (4)	−0.0114 (5)	−0.0263 (5)
N	0.0332 (15)	0.0466 (17)	0.0475 (17)	−0.0002 (13)	−0.0093 (13)	−0.0107 (14)
F1	0.136 (9)	0.160 (11)	0.165 (9)	−0.050 (8)	−0.033 (7)	−0.049 (8)
F2	0.082 (6)	0.104 (7)	0.133 (9)	−0.045 (5)	−0.035 (6)	−0.030 (6)
F3	0.101 (8)	0.077 (5)	0.074 (5)	0.016 (5)	−0.007 (5)	−0.048 (4)
F4	0.085 (8)	0.067 (5)	0.077 (7)	−0.003 (6)	−0.043 (6)	−0.016 (4)
F5	0.070 (6)	0.080 (7)	0.059 (5)	0.015 (5)	−0.024 (5)	−0.015 (4)
F6	0.097 (9)	0.078 (5)	0.083 (8)	−0.014 (6)	−0.038 (7)	−0.046 (5)
F1'	0.041 (3)	0.113 (7)	0.173 (7)	−0.002 (3)	−0.039 (3)	−0.027 (5)
F2'	0.118 (6)	0.180 (10)	0.147 (8)	−0.033 (7)	−0.069 (6)	−0.036 (7)
F3'	0.126 (7)	0.088 (4)	0.086 (4)	0.000 (5)	−0.021 (5)	−0.058 (3)
F4'	0.090 (7)	0.068 (4)	0.074 (4)	0.010 (5)	−0.009 (5)	−0.022 (3)
F5'	0.124 (8)	0.077 (4)	0.069 (4)	−0.014 (6)	−0.023 (6)	−0.023 (3)
F6'	0.074 (6)	0.078 (5)	0.075 (4)	0.002 (4)	0.003 (4)	−0.043 (3)
C1	0.064 (3)	0.052 (2)	0.057 (2)	0.0000 (19)	−0.015 (2)	−0.022 (2)
C2	0.084 (3)	0.086 (3)	0.066 (3)	−0.017 (3)	−0.040 (3)	−0.023 (3)
C3	0.051 (3)	0.095 (4)	0.066 (3)	−0.015 (2)	−0.031 (2)	−0.002 (3)
C4	0.042 (2)	0.083 (3)	0.066 (3)	0.014 (2)	−0.014 (2)	−0.021 (2)
C5	0.050 (2)	0.056 (2)	0.053 (2)	0.0118 (18)	−0.0171 (18)	−0.0268 (19)
C6	0.0340 (19)	0.066 (3)	0.066 (3)	−0.0019 (17)	−0.0187 (18)	−0.017 (2)
C7	0.0339 (19)	0.074 (3)	0.057 (2)	0.0055 (18)	−0.0156 (17)	−0.027 (2)
C8	0.044 (2)	0.082 (3)	0.060 (2)	0.009 (2)	−0.0230 (19)	−0.035 (2)

P—F1'	1.535 (7)	C3—C4	1.350 (7)
P—F6	1.567 (19)	C3—H3A	0.9300
P—F2'	1.575 (15)	C4—C5	1.379 (6)
P—F3	1.582 (11)	C4—H4A	0.9300
P—F2	1.583 (14)	C5—N	1.372 (5)
P—F5	1.588 (16)	C5—H5A	0.9300
P—F6'	1.604 (14)	N—C6	1.476 (5)
P—F4'	1.611 (14)	C6—C7	1.518 (6)
P—F4	1.612 (18)	C6—H6A	0.9700
P—F5'	1.617 (14)	C6—H6B	0.9700
P—F1	1.619 (15)	C7—C8	1.534 (5)
P—F3'	1.631 (9)	C7—H7A	0.9700
C1—N	1.347 (5)	C7—H7B	0.9700
C1—C2	1.375 (6)	C8—C8i	1.518 (7)
C1—H1A	0.9300	C8—H8A	0.9700
C2—C3	1.397 (7)	C8—H8B	0.9700
C2—H2A	0.9300
F1'—P—F6	85.7 (10)	F4—P—F1	83.6 (8)
F1'—P—F2'	173.4 (6)	F5'—P—F1	116.5 (8)
F6—P—F2'	95.7 (10)	F1'—P—F3'	97.5 (6)
F1'—P—F3	70.4 (7)	F6—P—F3'	176.5 (11)
F6—P—F3	156.1 (13)	F2'—P—F3'	80.9 (7)
F2'—P—F3	107.8 (9)	F2—P—F3'	78.8 (9)
F1'—P—F2	164.7 (6)	F5—P—F3'	92.5 (8)
F6—P—F2	98.4 (9)	F6'—P—F3'	160.7 (10)
F3—P—F2	105.1 (10)	F4'—P—F3'	90.4 (7)
F1'—P—F5	76.2 (6)	F4—P—F3'	86.1 (8)
F6—P—F5	89.5 (10)	F5'—P—F3'	88.0 (6)
F2'—P—F5	110.2 (6)	F1—P—F3'	112.6 (7)
F3—P—F5	86.5 (8)	N—C1—C2	120.6 (4)
F2—P—F5	89.1 (7)	N—C1—H1A	119.7
F1'—P—F6'	101.7 (9)	C2—C1—H1A	119.7
F2'—P—F6'	80.1 (9)	C1—C2—C3	118.7 (4)
F3—P—F6'	172.1 (12)	C1—C2—H2A	120.7
F2—P—F6'	82.4 (8)	C3—C2—H2A	120.7
F5—P—F6'	91.2 (9)	C4—C3—C2	119.8 (4)
F1'—P—F4'	86.0 (5)	C4—C3—H3A	120.1
F6—P—F4'	88.5 (9)	C2—C3—H3A	120.1
F2'—P—F4'	87.5 (6)	C3—C4—C5	121.1 (4)
F3—P—F4'	88.2 (7)	C3—C4—H4A	119.4
F2—P—F4'	108.7 (6)	C5—C4—H4A	119.4
F5—P—F4'	162.2 (6)	N—C5—C4	118.6 (4)
F6'—P—F4'	91.8 (7)	N—C5—H5A	120.7
F1'—P—F4	104.3 (6)	C4—C5—H5A	120.7
F6—P—F4	91.8 (10)	C1—N—C5	121.2 (3)
F2'—P—F4	69.2 (7)	C1—N—C6	120.7 (3)
F3—P—F4	92.5 (9)	C5—N—C6	118.1 (3)
F2—P—F4	90.3 (7)	N—C6—C7	112.5 (3)
F5—P—F4	178.6 (11)	N—C6—H6A	109.1
F6'—P—F4	90.0 (9)	C7—C6—H6A	109.1
F1'—P—F5'	95.7 (6)	N—C6—H6B	109.1
F6—P—F5'	93.0 (9)	C7—C6—H6B	109.1
F2'—P—F5'	90.7 (6)	H6A—C6—H6B	107.8
F3—P—F5'	91.0 (7)	C6—C7—C8	112.7 (3)
F2—P—F5'	69.5 (6)	C6—C7—H7A	109.0
F6'—P—F5'	89.2 (8)	C8—C7—H7A	109.0
F4'—P—F5'	177.8 (7)	C6—C7—H7B	109.0
F4—P—F5'	159.8 (6)	C8—C7—H7B	109.0
F6—P—F1	69.9 (12)	H7A—C7—H7B	107.8
F2'—P—F1	149.1 (8)	C8i—C8—C7	113.4 (4)
F3—P—F1	87.2 (7)	C8i—C8—H8A	108.9
F2—P—F1	166.6 (10)	C7—C8—H8A	108.9
F5—P—F1	97.2 (9)	C8i—C8—H8B	108.9
F6'—P—F1	85.7 (11)	C7—C8—H8B	108.9
F4'—P—F1	65.6 (7)	H8A—C8—H8B	107.7

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···F4'ii	0.93	2.48	3.333 (17)	153
C2—H2A···F2'iii	0.93	2.53	3.267 (18)	137
C3—H3A···F3'iii	0.93	2.47	3.257 (15)	142
C4—H4A···F1'iv	0.93	2.52	3.287 (14)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯F4′i	0.93	2.48	3.333 (17)	153
C2—H2A⋯F2′ii	0.93	2.53	3.267 (18)	137
C3—H3A⋯F3′ii	0.93	2.47	3.257 (15)	142
C4—H4A⋯F1′iii	0.93	2.52	3.287 (14)	140

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