1,1′-[(1,3-Dihydroxypropane-2,2-diyl)dimethylene]dipyridinium bis­(hexa­fluoro­phosphate)

Yuan, A.; Zheng, C.; Zhuang, L.; Wang, C.; Wang, G.

doi:10.1107/S1600536811013080

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1104

doi:10.1107/S1600536811013080

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1,1′-[(1,3-Dihydroxypropane-2,2-diyl)dimethylene]dipyridinium bis(hexafluorophosphate)

Ai-lin Yuan,^a Chun-ling Zheng,^a Ling-hua Zhuang,^b Chang-sheng Wang ^a and Guo-wei Wang ^a ^*

^aDepartment of Light Chemical Engineering, College of Food Science and Light Industry, Nanjing University of Technology, Nanjing 210009, People's Republic of China, and ^bDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: kingwell2004@sina.com.cn

(Received 8 February 2011; accepted 7 April 2011; online 13 April 2011)

The title compound, C₁₅H₂₀N₂O₂²⁺·2PF₆⁻, was prepared by anion exchange of two bromide ions in the ionic liquid 2,2′-bis-(pyridinium-1-ylmethyl)-propane-1,3-diol dibromide with potassium hexafluorophosphate. 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

C₁₅H₂₀N₂O₂²⁺·2PF₆⁻
M_r = 550.27
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.053
wR(F²) = 0.141
S = 1.04
3835 reflections
372 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

Ionic liquids (ILs) have enjoyed vast research interests in recent years because of their unique physicochemical properties (Welton, 1999). Geminal dicationic ionic liquids have been shown to possess superior properties in terms of thermal stability and volatility compared to traditional ionic liquids (ILs) (Liang et al., 2008). Consequently, they have been proposed as solvents in high-temperature reactions, as novel high-temperature lubricants or ultrastable separation phases (Yang et al., 2010).

As part of our ongoing studies on new geminal dicationic ionic liquids (Geng et al., 2010; Yuan et al., 2010), we here report the crystal structure of the title compound (I).

The atom-numbering scheme of (I) is shown in Fig.1. Intramolecular C—H···O hydrogen bonds are observed between the methylene groups next to the pyridine N atoms ans the hydroxy groups. All bond lengths are within normal ranges (Allen et al., 1987). The two pyridine rings are planar (r.m.s. deviations = 0.008 and 0.004 Å) and make a dihedral angle of 44.0 (2)°. (Table 1, Fig. 1).

Related literature top

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 the title compound, see: Yuan et al. (2010). For bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of pyridine (1.98 g, 25 mmol) and 2,2-bis-(bromomethyl)-propane-1,3-diol (2.60 g, 10 mmol) was stirred vigorously at 387 K for 16 h. After cooling to room temperature, the crude product was washed with acetonitrile. The resulting solid collected by filtration was treated with water (20 ml) as well as KPF₆ (3.68 g, 20 mmol) and the reaction mixture was stirred at room temperature for 1 h. After filtration, the white solid was washed with ethanol and dried in vacuo to give the title compound (I) (4.82 g, 88%). M.p. 508–510 K. Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of a methanolic solution. ¹H NMR (DMSO, δ, p.p.m.) 8.92 (t, 4 H), 8.68 (m, 2 H), 8.20 (m, 4 H), 5.57 (s, 2 H) 4.79 (s, 4 H), 3.16 (s, 4 H).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); 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 (Sheldrick, 2008).

Figures top

Fig. 1. A view of the molecular structure of (I) showing the atom-numbering scheme and 30% displacement ellipsoids. Dashed lines indicte hydrogen bonds.

1,1'-[(1,3-Dihydroxypropane-2,2-diyl)dimethylene]dipyridinium bis(hexafluorophosphate) top

Crystal data top

C₁₅H₂₀N₂O₂²⁺·2PF₆⁻	F(000) = 1112
M_r = 550.27	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0676P)² + 0.894P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3835 reflections	Δρ_max = 0.36 e Å⁻³
372 parameters	Δρ_min = −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)

Crystal data top

C₁₅H₂₀N₂O₂²⁺·2PF₆⁻	V = 2087.3 (7) Å³
M_r = 550.27	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.955 (2) Å	µ = 0.33 mm⁻¹
b = 13.796 (3) Å	T = 293 K
c = 12.707 (3) Å	0.30 × 0.20 × 0.10 mm
β = 95.17 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2564 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.031
T_min = 0.907, T_max = 0.968	3 standard reflections every 200 reflections
4027 measured reflections	intensity decay: 1%
3835 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.04	Δρ_max = 0.36 e Å⁻³
3835 reflections	Δρ_min = −0.26 e Å⁻³
372 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1/2, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₂₀N₂O₂²⁺·2PF₆⁻
M_r	550.27
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	11.955 (2), 13.796 (3), 12.707 (3)
β (°)	95.17 (3)
V (Å³)	2087.3 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.907, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	4027, 3835, 2564
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.141, 1.04
No. of reflections	3835
No. of parameters	372
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.26

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo,1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x+1/2, −y+3/2, z+1/2.

Acknowledgements

We acknowledge the National Natural Science Foundation of China (No. 51003047) and the Foundation for Young Teachers Scholarship of Nanjing University of Technology, Jiangsu, China (No. 39729005) for financial support. The authors thank the Centre of Testing and Analysis, Nanjing University, for the data collection.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Geng, H., Zhuang, L., Zhang, J., Wang, G. & Yuan, A. (2010). Acta Cryst. E66, o1267. Web of Science CSD CrossRef IUCr Journals Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Liang, J., Dong, S., Cang, H. & Wang, J. (2008). Acta Cryst. E64, o2480. Web of Science CSD CrossRef IUCr Journals Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Welton, T. (1999). Chem. Rev. 99, 2071–2083. Web of Science CrossRef PubMed CAS Google Scholar
Yang, X. Z., Wang, J. & Zhang, Z. Z. (2010). J. Chem. Eng. Data, 55, 586–588. CrossRef CAS Google Scholar
Yuan, A.-L., Wang, C.-S., Zhuang, L.-H. & Wang, G.-W. (2010). Acta Cryst. E66, o3282. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 5| May 2011| Page o1104

doi:10.1107/S1600536811013080

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1,1′-[(1,3-Di­hydroxypropane-2,2-diyl)di­methylene]dipyridinium bis­­(hexa­fluoro­phosphate)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1,1′-[(1,3-Dihydroxypropane-2,2-diyl)dimethylene]dipyridinium bis(hexafluorophosphate)