3,3'-Diethyl-1,1'-(1,4-phenyl-ene-dimethyl-ene)diimidazol-3-ium bis-(hexa-fluoro-phosphate).

In the title mol-ecular salt, C(18)H(24)N(4) (2+)·2PF(6) (-), the complete dication is generated by a crystallographic inversion centre. The central benzene ring makes a dihedral angle of 77.19 (9)° with each of the imidazole rings. In the crystal, C-H⋯F inter-actions link the cations and anions into layers lying parallel to the bc plane. The hexa-fluoro-phosphate anion is disordered over two sets of sites in a 0.520 (11):0.480 (11) ratio.

Related literature

For the properties of imidzole derivates, see: Shargel et al. (2006 ▶). For related structures, see: Haque et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C18H24N4 2+·2PF6 −

M = 586.35

Triclinic,

a = 8.5441 (5) Å

b = 8.6018 (5) Å

c = 9.5626 (6) Å

α = 67.913 (1)°

β = 77.928 (1)°

γ = 67.837 (1)°

V = 601.25 (6) Å3

Z = 1

Mo Kα radiation

μ = 0.29 mm−1

T = 297 K

0.28 × 0.25 × 0.12 mm

Data collection

Bruker APEX DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.925, T max = 0.966

12274 measured reflections

3996 independent reflections

2968 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.170

S = 1.04

3996 reflections

228 parameters

21 restraints

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812028966/hb6877sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028966/hb6877Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812028966/hb6877Isup3.cml

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

C18H24N42+·2PF6−	Z = 1
Mr = 586.35	F(000) = 298
Triclinic, P1	Dx = 1.619 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5441 (5) Å	Cell parameters from 3921 reflections
b = 8.6018 (5) Å	θ = 2.3–29.3°
c = 9.5626 (6) Å	µ = 0.29 mm−1
α = 67.913 (1)°	T = 297 K
β = 77.928 (1)°	Block, colourless
γ = 67.837 (1)°	0.28 × 0.25 × 0.12 mm
V = 601.25 (6) Å3

Bruker APEX DUO CCD diffractometer	3996 independent reflections
Radiation source: fine-focus sealed tube	2968 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
φ and ω scans	θmax = 31.7°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
Tmin = 0.925, Tmax = 0.966	k = −12→12
12274 measured reflections	l = −14→13

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.087P)2 + 0.1678P] where P = (Fo2 + 2Fc2)/3
3996 reflections	(Δ/σ)max = 0.026
228 parameters	Δρmax = 0.38 e Å−3
21 restraints	Δρmin = −0.36 e Å−3

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)
P1	0.2804 (5)	0.8326 (6)	0.7615 (5)	0.0638 (15)	0.520 (11)
F1	0.3579 (13)	0.9624 (13)	0.7737 (9)	0.131 (3)	0.520 (11)
F2	0.4136 (13)	0.7509 (17)	0.6579 (12)	0.199 (7)	0.520 (11)
F3	0.2044 (14)	0.6984 (10)	0.7644 (13)	0.163 (4)	0.520 (11)
F4	0.1422 (6)	0.8696 (10)	0.8921 (5)	0.107 (3)	0.520 (11)
F5	0.3982 (12)	0.7149 (17)	0.8932 (9)	0.166 (5)	0.520 (11)
F6	0.1612 (11)	0.9775 (11)	0.6426 (9)	0.114 (3)	0.520 (11)
P1X	0.2841 (4)	0.8298 (4)	0.7654 (4)	0.0360 (7)	0.480 (11)
F1X	0.3854 (13)	0.9578 (14)	0.718 (2)	0.203 (6)	0.480 (11)
F2X	0.4179 (9)	0.7801 (15)	0.6381 (8)	0.125 (4)	0.480 (11)
F3X	0.1751 (10)	0.7065 (9)	0.8061 (13)	0.142 (5)	0.480 (11)
F4X	0.1575 (11)	0.9329 (18)	0.8653 (13)	0.176 (5)	0.480 (11)
F5X	0.3981 (10)	0.6706 (12)	0.8876 (10)	0.124 (3)	0.480 (11)
F6X	0.1650 (13)	0.9487 (15)	0.6319 (9)	0.123 (4)	0.480 (11)
N1	0.7726 (2)	0.9473 (2)	0.78904 (17)	0.0434 (3)
N2	0.80090 (18)	0.67771 (18)	0.81853 (15)	0.0376 (3)
C1	0.5791 (3)	1.2530 (3)	0.7237 (4)	0.0789 (8)
H1A	0.5718	1.3735	0.6648	0.118*
H1B	0.5405	1.2453	0.8271	0.118*
H1C	0.5094	1.2165	0.6841	0.118*
C2	0.7574 (3)	1.1356 (3)	0.7159 (3)	0.0580 (5)
H2A	0.8010	1.1559	0.6108	0.070*
H2B	0.8255	1.1650	0.7653	0.070*
C3	0.7587 (3)	0.8606 (3)	0.9407 (2)	0.0568 (5)
H3A	0.7410	0.9089	1.0171	0.068*
C4	0.7751 (3)	0.6920 (3)	0.9598 (2)	0.0512 (5)
H4A	0.7700	0.6025	1.0515	0.061*
C5	0.7975 (2)	0.8345 (2)	0.71706 (19)	0.0424 (4)
H5A	0.8106	0.8607	0.6126	0.051*
C6	0.8154 (3)	0.5168 (2)	0.78841 (19)	0.0460 (4)
H6A	0.7027	0.5143	0.7890	0.055*
H6B	0.8726	0.4127	0.8689	0.055*
C7	0.9118 (2)	0.5083 (2)	0.63878 (17)	0.0375 (3)
C8	0.8268 (2)	0.5812 (3)	0.5089 (2)	0.0513 (5)
H8A	0.7099	0.6362	0.5139	0.062*
C9	1.0854 (3)	0.4272 (3)	0.6285 (2)	0.0512 (5)
H9A	1.1440	0.3775	0.7151	0.061*

	U11	U22	U33	U12	U13	U23
P1	0.061 (2)	0.066 (2)	0.052 (2)	−0.0193 (18)	−0.0073 (16)	−0.0066 (16)
F1	0.183 (8)	0.157 (6)	0.133 (5)	−0.118 (5)	0.029 (4)	−0.093 (5)
F2	0.131 (7)	0.242 (11)	0.180 (9)	0.076 (7)	−0.016 (6)	−0.158 (8)
F3	0.213 (9)	0.120 (5)	0.224 (8)	−0.102 (5)	−0.040 (7)	−0.070 (6)
F4	0.060 (2)	0.168 (5)	0.049 (2)	−0.027 (3)	0.0210 (15)	−0.013 (3)
F5	0.090 (5)	0.284 (12)	0.084 (4)	−0.030 (6)	−0.052 (4)	−0.026 (6)
F6	0.084 (4)	0.078 (3)	0.087 (5)	0.005 (2)	0.005 (3)	0.035 (3)
P1X	0.0345 (13)	0.0375 (13)	0.0373 (15)	−0.0150 (10)	0.0042 (10)	−0.0143 (11)
F1X	0.102 (5)	0.148 (7)	0.343 (16)	−0.096 (5)	−0.007 (7)	−0.013 (8)
F2X	0.073 (4)	0.213 (9)	0.061 (3)	−0.023 (5)	0.027 (3)	−0.055 (4)
F3X	0.088 (3)	0.092 (4)	0.196 (8)	−0.060 (3)	−0.062 (4)	0.064 (5)
F4X	0.115 (5)	0.273 (10)	0.239 (9)	−0.035 (6)	0.011 (5)	−0.231 (9)
F5X	0.070 (4)	0.105 (4)	0.107 (5)	−0.005 (3)	−0.011 (3)	0.041 (3)
F6X	0.089 (5)	0.178 (9)	0.048 (3)	−0.007 (5)	−0.026 (3)	−0.004 (4)
N1	0.0464 (8)	0.0408 (7)	0.0481 (8)	−0.0170 (6)	0.0016 (6)	−0.0202 (6)
N2	0.0450 (7)	0.0383 (7)	0.0311 (6)	−0.0158 (5)	0.0033 (5)	−0.0145 (5)
C1	0.0633 (15)	0.0511 (12)	0.114 (2)	−0.0112 (11)	−0.0112 (14)	−0.0229 (14)
C2	0.0608 (12)	0.0401 (9)	0.0745 (14)	−0.0204 (8)	0.0033 (10)	−0.0211 (9)
C3	0.0789 (14)	0.0595 (12)	0.0443 (10)	−0.0269 (10)	0.0003 (9)	−0.0286 (9)
C4	0.0739 (13)	0.0520 (10)	0.0319 (8)	−0.0240 (9)	−0.0003 (8)	−0.0170 (7)
C5	0.0519 (9)	0.0406 (8)	0.0356 (7)	−0.0179 (7)	0.0035 (6)	−0.0146 (6)
C6	0.0636 (11)	0.0412 (8)	0.0374 (8)	−0.0244 (8)	0.0100 (7)	−0.0177 (7)
C7	0.0481 (9)	0.0326 (7)	0.0328 (7)	−0.0135 (6)	0.0019 (6)	−0.0143 (6)
C8	0.0389 (9)	0.0648 (12)	0.0444 (9)	−0.0058 (8)	−0.0033 (7)	−0.0231 (9)
C9	0.0506 (10)	0.0611 (11)	0.0360 (8)	−0.0064 (8)	−0.0097 (7)	−0.0181 (8)

P1—F2	1.490 (7)	C1—H1A	0.9600
P1—F3	1.513 (6)	C1—H1B	0.9600
P1—F6	1.531 (7)	C1—H1C	0.9600
P1—F1	1.545 (6)	C2—H2A	0.9700
P1—F5	1.558 (7)	C2—H2B	0.9700
P1—F4	1.566 (5)	C3—C4	1.347 (3)
P1X—F4X	1.533 (6)	C3—H3A	0.9300
P1X—F1X	1.532 (7)	C4—H4A	0.9300
P1X—F2X	1.553 (6)	C5—H5A	0.9300
P1X—F3X	1.557 (6)	C6—C7	1.507 (2)
P1X—F5X	1.567 (6)	C6—H6A	0.9700
P1X—F6X	1.577 (6)	C6—H6B	0.9700
N1—C5	1.321 (2)	C7—C9	1.381 (3)
N1—C3	1.362 (3)	C7—C8	1.382 (2)
N1—C2	1.469 (2)	C8—C9i	1.383 (2)
N2—C5	1.327 (2)	C8—H8A	0.9300
N2—C4	1.367 (2)	C9—C8i	1.383 (2)
N2—C6	1.473 (2)	C9—H9A	0.9300
C1—C2	1.482 (3)
F2—P1—F3	82.7 (7)	C2—C1—H1A	109.5
F2—P1—F6	98.2 (6)	C2—C1—H1B	109.5
F3—P1—F6	90.4 (5)	H1A—C1—H1B	109.5
F2—P1—F1	100.0 (7)	C2—C1—H1C	109.5
F3—P1—F1	175.0 (6)	H1A—C1—H1C	109.5
F6—P1—F1	93.3 (6)	H1B—C1—H1C	109.5
F2—P1—F5	88.9 (6)	N1—C2—C1	111.63 (19)
F3—P1—F5	98.9 (7)	N1—C2—H2A	109.3
F6—P1—F5	169.0 (8)	C1—C2—H2A	109.3
F1—P1—F5	77.1 (6)	N1—C2—H2B	109.3
F2—P1—F4	165.7 (7)	C1—C2—H2B	109.3
F3—P1—F4	86.3 (5)	H2A—C2—H2B	108.0
F6—P1—F4	90.8 (5)	C4—C3—N1	107.53 (16)
F1—P1—F4	90.4 (4)	C4—C3—H3A	126.2
F5—P1—F4	83.8 (5)	N1—C3—H3A	126.2
F4X—P1X—F1X	90.9 (6)	C3—C4—N2	106.79 (17)
F4X—P1X—F2X	163.0 (8)	C3—C4—H4A	126.6
F1X—P1X—F2X	74.1 (7)	N2—C4—H4A	126.6
F4X—P1X—F3X	89.2 (5)	N1—C5—N2	108.71 (15)
F1X—P1X—F3X	176.8 (6)	N1—C5—H5A	125.6
F2X—P1X—F3X	105.3 (6)	N2—C5—H5A	125.6
F4X—P1X—F5X	100.5 (7)	N2—C6—C7	112.44 (14)
F1X—P1X—F5X	99.7 (6)	N2—C6—H6A	109.1
F2X—P1X—F5X	90.0 (5)	C7—C6—H6A	109.1
F3X—P1X—F5X	83.5 (5)	N2—C6—H6B	109.1
F4X—P1X—F6X	88.6 (6)	C7—C6—H6B	109.1
F1X—P1X—F6X	92.3 (7)	H6A—C6—H6B	107.8
F2X—P1X—F6X	84.2 (6)	C9—C7—C8	118.74 (15)
F3X—P1X—F6X	84.5 (5)	C9—C7—C6	121.03 (16)
F5X—P1X—F6X	164.7 (7)	C8—C7—C6	120.23 (17)
C5—N1—C3	108.48 (15)	C9i—C8—C7	120.44 (17)
C5—N1—C2	125.15 (17)	C9i—C8—H8A	119.8
C3—N1—C2	126.35 (17)	C7—C8—H8A	119.8
C5—N2—C4	108.49 (15)	C7—C9—C8i	120.82 (16)
C5—N2—C6	127.06 (14)	C7—C9—H9A	119.6
C4—N2—C6	124.27 (15)	C8i—C9—H9A	119.6
C5—N1—C2—C1	104.3 (3)	C6—N2—C5—N1	176.08 (17)
C3—N1—C2—C1	−73.6 (3)	C5—N2—C6—C7	29.1 (3)
C5—N1—C3—C4	−0.2 (3)	C4—N2—C6—C7	−156.30 (18)
C2—N1—C3—C4	178.0 (2)	N2—C6—C7—C9	90.2 (2)
N1—C3—C4—N2	0.6 (3)	N2—C6—C7—C8	−90.3 (2)
C5—N2—C4—C3	−0.9 (2)	C9—C7—C8—C9i	−0.1 (3)
C6—N2—C4—C3	−176.35 (19)	C6—C7—C8—C9i	−179.61 (18)
C3—N1—C5—N2	−0.4 (2)	C8—C7—C9—C8i	0.1 (3)
C2—N1—C5—N2	−178.59 (18)	C6—C7—C9—C8i	179.61 (18)
C4—N2—C5—N1	0.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···F1ii	0.93	2.49	3.408 (10)	170
C4—H4A···F3iii	0.93	2.48	3.369 (11)	160
C5—H5A···F6iv	0.93	2.32	3.211 (8)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯F1i	0.93	2.49	3.408 (10)	170
C4—H4A⋯F3ii	0.93	2.48	3.369 (11)	160
C5—H5A⋯F6iii	0.93	2.32	3.211 (8)	159

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