1,3-Bis[(3-allyl­imidazol-3-ium-1-yl)meth­yl]benzene bis­(hexa­fluoridophosphate)

Haque, R.A.; Ghdhayeb, M.Z.; Abdallah, H.H.; Quah, C.K.; Fun, H.-K.

doi:10.1107/S1600536810050683

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 1| January 2011| Pages o80-o81

https://doi.org/10.1107/S1600536810050683

Open

access

1,3-Bis[(3-allylimidazol-3-ium-1-yl)methyl]benzene bis(hexafluoridophosphate)

Rosenani A. Haque,^a Mohammed Z. Ghdhayeb,^a Hassan H. Abdallah,^a Ching Kheng Quah ^b ‡ and Hoong-Kun Fun ^b ^*§

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 23 November 2010; accepted 3 December 2010; online 11 December 2010)

In the title compound, C₂₀H₂₄N₄²⁺·2PF₆⁻, the ethene and 3-allylimidazolium moieties of the cation are disordered over two positions with refined site occupancies of 0.664 (19):0.336 (19) and 0.784 (7):0.216 (7), respectively, whereas four F atoms of one hexafluoridophosphate anion and all atoms in the other hexafluoridophosphate anion are disordered over two positions with refined site occupancies of 0.764 (5):0.2365) and 0.847 (9):0.153 (9), respectively. The benzene ring is inclined at angles of 78.2 (3), 81.3 (4) and 73.9 (12)° with the 1H-imidazol-3-ium ring and the major and minor components of the disordered 1H-imidazol-3-ium ring, respectively. In the crystal, the hexafluoridophosphate anions link the cations into two-dimensional networks parallel to (001) via intermolecular C—H⋯F hydrogen bonds. The crystal structure is further consolidated by π–π [centroid–centroid distance = 3.672 (3) Å] and C—H⋯π interactions.

Related literature

For general background to and the biological activity of carbene derivatives, see: Yang & Nolan (2001 ); Böhm et al. (2000 ); Jafarpour & Nolan (2001 ); Bourissou et al. (2000 ); Herrmann et al. (1996 , 1997 ); Arduengo et al. (1991 ); Danopoulos et al. (2002 ); Dias & Jin (1994 ); Caballero et al. (2001 ); Thompson et al. (1999 ); Melaiye et al. (2005 ). For bond-length data, see: Allen et al. (1987 ). For a related structure, see: Haque et al. (2010 ).

Experimental

Crystal data

C₂₀H₂₄N₄²⁺·2PF₆⁻
M_r = 610.37
Monoclinic, P 2₁ /c
a = 9.8748 (4) Å
b = 9.9098 (3) Å
c = 26.124 (1) Å
β = 101.138 (2)°
V = 2508.27 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 296 K
0.25 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.921, T_max = 0.924
35601 measured reflections
5217 independent reflections
4324 reflections with I > 2σ(I)
R_int = 0.059

Refinement

R[F² > 2σ(F²)] = 0.108
wR(F²) = 0.201
S = 1.14
5217 reflections
431 parameters
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the N3A/N4A/C15A–C17A and N3B/N4B/C15B–C17B rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯F7Aⁱ	0.93	2.40	3.276 (6)	156
C5—H5A⋯F5ⁱⁱ	0.93	2.51	3.320 (6)	146
C8—H8A⋯F11Aⁱⁱⁱ	0.93	2.27	3.107 (8)	150
C10—H10A⋯F7A	0.93	2.25	3.130 (6)	158
C16A—H16A⋯F6ⁱⁱⁱ	0.93	2.48	3.407 (9)	172
C20A—H20A⋯Cg2	0.93	2.89	3.489 (11)	123
C20B—H20C⋯Cg3	0.93	2.84	3.44 (5)	124
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x, y-1, z; (iii) x+1, y, z.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810050683/rz2529sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810050683/rz2529Isup2.hkl

checkCIF report

Comment top

Carbenes are compounds possessing a neutral divalent carbon atom with six electrons on its valence shell. N-heterocyclic carbenes (NHCs) are cyclic carbenes that are usually derived from the deprotonation of imidazolium salts. NHCs are strong σ-donating ligands (Yang & Nolan, 2001; Böhm et al., 2000) with negligible π -back bonding tendencies (Jafarpour & Nolan, 2001; Bourissou et al., 2000; Herrmann et al., 1996). The isolation of crystalline stable free NHC by Arduengo (Arduengo et al., 1991) provided information on their fundamental properties. Many researchers have since prepared free NHCs for use in other reactions (usually for metal complexation reactions). Danopoulos and co-worker (Danopoulos et al., 2002) isolated a stable phosphine-functionalised carbene. Various compounds that contain more than one carbene centres are known (Dias & Jin, 1994; Caballero et al. , 2001). Carbene have the ability to form complexes with many metals (Herrmann et al., 1997), of which transition metals are the most interesting due to their potentials for catalytic activity. All transition metals have been complexed with NHC and the applications of compounds came to focus in many areas including the medical and biological sciences (Thompson et al., 1999; Melaiye et al., 2005).

In the title molecule (Fig. 1), the phenyl (C1-C6) ring is inclined at angles of 78.2 (3), 81.3 (4) and 73.9 (12)° with 1H-imidazol-3-ium (N1/N2/C8-C10, maximum deviation = 0.005 (5) Å at atom C10) ring, major component of 1H-imidazol-3-ium (N3A/N4A/C15A-C17A, maximum deviation = 0.008 (8) Å at atom N3A) ring and minor component of 1H-imidazol-3-ium (N3B/N4B/C15B-C17B, maximum deviation = 0.01 (3) Å at atoms N3B/C15B/C16B) ring, respectively. The ethene (C12/C13) and 3-allylimidazolium (N3/N4/C15-C20) moieties of the cation are disordered over two positions with refined site-occupancies of 0.664 (19) : 0.336 (19) and 0.784 (7) : 0.216 (7), respectively, whereas four fluorine atoms (F1A-F4A) of the hexafluoridophosphate (A) and a full hexafluoridophosphate (B) anion are disordered over two positions with refined site-occupancies of 0.764 (5) : 0.236 (5) and 0.847 (9) : 0.153 (9), respectively. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to a related structure (Haque et al., 2010).

In the crystal packing (Fig. 2), the hexafluoridophosphate anions link the cations into two-dimensional networks parallel to (001) via intermolecular C3–H3A···F7A, C5–H5A···F5, C8–H8A···F11A, C10–H10A···F7A and C16A–H16A···F6 (Table 1) hydrogen bonds. π-π stacking interactions between the centroid of C1-C6 phenyl rings (Cg1), with Cg1···Cg1ⁱ distance of 3.672 (3) Å [symmetry code: (i) 1-X, 1-Y, -Z] are observed. The crystal structure is further consilidated by C20A–H20A···Cg2, C20B–H20C···Cg3 (Table 1) interactions, where Cg2 and Cg3 are the centroid of N3A/N4A/C15A-C17A and N3B/N4B/C15B-C17B rings, respectively.

Related literature top

For general background to and the biological activity of carbene derrivatives, see: Yang & Nolan (2001); Böhm et al. (2000); Jafarpour & Nolan (2001); Bourissou et al. (2000); Herrmann et al. (1996); Arduengo et al. (1991); Danopoulos et al. (2002); Dias & Jin (1994); Caballero et al. (2001); Herrmann et al. (1997); Thompson et al. (1999); Melaiye et al. (2005). For bond-length data, see: Allen et al. (1987). For a related structure, see: Haque et al. (2010).

Experimental top

A mixture of imidazole (9.0 g, 130 mmol) and sodium hydroxide (5.0 g, 120 mmol) in DMSO (30 ml) was heated to 90 °C for 2 h. The mixture was cooled to room temperature and a solution of 1,3-bis(bromomethyl)benzene (15.0 g, 57 mmol) in DMSO (30 mL) was added, heated at 40 °C (1 h) and then poured into water (400 mL) followed by cooling in ice. Recrystallisation from methanol/water gives 1,3-bis(N-imidazole-1-yl methyl)benzene (1) as a white solid (9.0 g, 75%). Further, a mixture of 1 (0.5 g, 2.1 mmol) and allyl bromide (0.5 g, 4.2 mmol) in acetonitrile (30 mL) was refluxed at 90 °C for 24 h. The solvent was removed under reduced pressure to give 2.2Br as a pale-brown oil which was then reacted with KPF₆ (0.22 g, 1.2 mmol) in 20 ml of methanol to yield the title compound. Recrystallisation from acetonitrile gives title compound as colourless solid. Yield: 0.4 g (60%). Crystals suitable for x-ray diffraction studies were obtained by slow evaporation of the salt solution in acetonitrile at room temperature.

Structure description top

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids for non-H atoms and the atom-numbering scheme. Both major and minor components of disorder are shown.
	Fig. 2. The crystal structure of the title compound, viewed along the c axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity. Only major component of disorder is shown.

3,3'-Diallyl-1,1'-[m-phenylenebis(methylidene)]diimidazol-3-ium bis(hexafluoridophosphate) top

Crystal data top

C₂₀H₂₄N₄²⁺·2PF₆⁻	F(000) = 1240
M_r = 610.37	D_x = 1.616 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9952 reflections
a = 9.8748 (4) Å	θ = 2.6–29.8°
b = 9.9098 (3) Å	µ = 0.28 mm⁻¹
c = 26.124 (1) Å	T = 296 K
β = 101.138 (2)°	Block, colourless
V = 2508.27 (16) Å³	0.25 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5217 independent reflections
Radiation source: fine-focus sealed tube	4324 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.059
φ and ω scans	θ_max = 26.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
T_min = 0.921, T_max = 0.924	k = −12→12
35601 measured reflections	l = −32→32

Refinement top

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)] = 0.108	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.201	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.P)² + 16.2482P] where P = (F_o² + 2F_c²)/3
5217 reflections	(Δ/σ)_max < 0.001
431 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

C₂₀H₂₄N₄²⁺·2PF₆⁻	V = 2508.27 (16) Å³
M_r = 610.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.8748 (4) Å	µ = 0.28 mm⁻¹
b = 9.9098 (3) Å	T = 296 K
c = 26.124 (1) Å	0.25 × 0.20 × 0.20 mm
β = 101.138 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5217 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4324 reflections with I > 2σ(I)
T_min = 0.921, T_max = 0.924	R_int = 0.059
35601 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.108	0 restraints
wR(F²) = 0.201	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.P)² + 16.2482P] where P = (F_o² + 2F_c²)/3
5217 reflections	Δρ_max = 0.55 e Å⁻³
431 parameters	Δρ_min = −0.56 e Å⁻³

Special details top

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	0.5923 (4)	0.5239 (4)	0.16321 (15)	0.0249 (9)
N2	0.5777 (4)	0.6625 (4)	0.22597 (14)	0.0263 (9)
C1	0.6305 (5)	0.5745 (5)	0.05490 (18)	0.0246 (10)
H1A	0.5974	0.6492	0.0702	0.030*
C2	0.6899 (5)	0.5907 (5)	0.01137 (18)	0.0296 (11)
C3	0.7363 (6)	0.4786 (6)	−0.01166 (19)	0.0371 (13)
H3A	0.7751	0.4891	−0.0411	0.044*
C4	0.7257 (5)	0.3512 (6)	0.0086 (2)	0.0364 (13)
H4A	0.7570	0.2765	−0.0072	0.044*
C5	0.6685 (5)	0.3349 (5)	0.0524 (2)	0.0311 (11)
H5A	0.6620	0.2494	0.0663	0.037*
C6	0.6204 (5)	0.4472 (5)	0.07570 (18)	0.0261 (10)
C7	0.5504 (6)	0.4246 (6)	0.1218 (2)	0.0381 (13)
H7A	0.4512	0.4292	0.1100	0.046*
H7B	0.5728	0.3349	0.1357	0.046*
C8	0.7251 (5)	0.5590 (6)	0.1867 (2)	0.0376 (13)
H8A	0.8062	0.5288	0.1774	0.045*
C9	0.7151 (5)	0.6452 (6)	0.2256 (2)	0.0359 (13)
H9A	0.7882	0.6858	0.2481	0.043*
C10	0.5055 (5)	0.5895 (5)	0.18780 (16)	0.0224 (10)
H10A	0.4097	0.5848	0.1794	0.027*
C11	0.5195 (6)	0.7522 (6)	0.26188 (19)	0.0385 (14)
H11A	0.5179	0.8445	0.2494	0.046*	0.664 (19)
H11B	0.5774	0.7490	0.2964	0.046*	0.664 (19)
H11C	0.5614	0.8395	0.2615	0.046*	0.336 (19)
H11D	0.5441	0.7173	0.2967	0.046*	0.336 (19)
C12A	0.3691 (10)	0.7065 (12)	0.2651 (4)	0.039 (2)	0.664 (19)
H12A	0.3593	0.6279	0.2835	0.046*	0.664 (19)
C13A	0.2577 (11)	0.7700 (13)	0.2440 (4)	0.055 (4)	0.664 (19)
H13A	0.2634	0.8489	0.2253	0.066*	0.664 (19)
H13B	0.1720	0.7367	0.2476	0.066*	0.664 (19)
C12B	0.3817 (18)	0.766 (2)	0.2496 (7)	0.031 (5)*	0.336 (19)
H12B	0.3441	0.8262	0.2233	0.037*	0.336 (19)
C13B	0.298 (3)	0.697 (2)	0.2737 (9)	0.050 (7)*	0.336 (19)
H13C	0.3340	0.6370	0.3000	0.061*	0.336 (19)
H13D	0.2030	0.7094	0.2642	0.061*	0.336 (19)
C14	0.7016 (6)	0.7302 (6)	−0.01020 (19)	0.0362 (13)
H14A	0.7142	0.7244	−0.0460	0.043*
H14B	0.6177	0.7806	−0.0097	0.043*
N3A	0.8163 (9)	0.7969 (9)	0.0208 (3)	0.028 (2)	0.784 (7)
N4A	0.9335 (6)	0.9437 (8)	0.0716 (2)	0.0304 (13)	0.784 (7)
C15A	0.9519 (7)	0.7540 (10)	0.0311 (4)	0.064 (3)	0.784 (7)
H15A	0.9869	0.6761	0.0186	0.077*	0.784 (7)
C16A	1.0226 (8)	0.8469 (9)	0.0623 (4)	0.061 (3)	0.784 (7)
H16A	1.1170	0.8454	0.0756	0.073*	0.784 (7)
C17A	0.8076 (7)	0.9105 (8)	0.0463 (3)	0.0297 (16)	0.784 (7)
H17A	0.7272	0.9592	0.0465	0.036*	0.784 (7)
C18A	0.9690 (7)	1.0591 (7)	0.1078 (3)	0.0380 (17)	0.784 (7)
H18A	0.9070	1.1336	0.0962	0.046*	0.784 (7)
H18B	1.0623	1.0886	0.1072	0.046*	0.784 (7)
C19A	0.9587 (8)	1.0219 (8)	0.1620 (3)	0.046 (2)	0.784 (7)
H19A	0.9747	1.0913	0.1864	0.056*	0.784 (7)
C20A	0.9300 (15)	0.9046 (13)	0.1798 (4)	0.074 (4)	0.784 (7)
H20A	0.9128	0.8310	0.1574	0.089*	0.784 (7)
H20B	0.9266	0.8944	0.2150	0.089*	0.784 (7)
N3B	0.815 (3)	0.834 (4)	0.0292 (13)	0.014 (7)*	0.216 (7)
N4B	0.981 (2)	0.896 (2)	0.0929 (9)	0.028 (5)*	0.216 (7)
C15B	0.833 (3)	0.969 (3)	0.0291 (12)	0.039 (7)*	0.216 (7)
H15B	0.7829	1.0269	0.0045	0.047*	0.216 (7)
C16B	0.933 (3)	1.011 (3)	0.0687 (11)	0.029 (7)*	0.216 (7)
H16B	0.9612	1.0991	0.0774	0.034*	0.216 (7)
C17B	0.913 (2)	0.792 (2)	0.0705 (8)	0.021 (5)*	0.216 (7)
H17B	0.9292	0.7032	0.0810	0.025*	0.216 (7)
C18B	1.079 (2)	0.897 (2)	0.1437 (8)	0.027 (5)*	0.216 (7)
H18C	1.1247	0.8105	0.1488	0.032*	0.216 (7)
H18D	1.1488	0.9652	0.1423	0.032*	0.216 (7)
C19B	1.015 (3)	0.925 (3)	0.1883 (10)	0.031 (6)*	0.216 (7)
H19B	1.0729	0.9232	0.2209	0.037*	0.216 (7)
C20B	0.883 (4)	0.952 (4)	0.1874 (18)	0.056 (12)*	0.216 (7)
H20C	0.8213	0.9552	0.1557	0.067*	0.216 (7)
H20D	0.8531	0.9685	0.2184	0.067*	0.216 (7)
P1A	0.44160 (14)	0.94789 (14)	0.10748 (6)	0.0324 (3)
F1A	0.4146 (8)	0.9819 (5)	0.1629 (2)	0.086 (2)	0.847 (9)
F2A	0.3010 (4)	1.0150 (5)	0.0787 (3)	0.073 (2)	0.847 (9)
F3A	0.4734 (6)	0.9122 (5)	0.0510 (2)	0.0663 (17)	0.847 (9)
F4A	0.5829 (5)	0.8749 (6)	0.1327 (2)	0.076 (2)	0.847 (9)
F5	0.5155 (4)	1.0898 (4)	0.10670 (16)	0.0693 (12)
F6	0.3674 (3)	0.8058 (3)	0.10771 (14)	0.0463 (9)
F1B	0.318 (3)	0.993 (3)	0.1411 (10)	0.045 (7)*	0.153 (9)
F2B	0.343 (3)	0.976 (2)	0.0549 (8)	0.037 (6)*	0.153 (9)
F3B	0.556 (3)	0.908 (2)	0.0792 (10)	0.045 (7)*	0.153 (9)
F4B	0.539 (2)	0.926 (2)	0.1628 (7)	0.026 (5)*	0.153 (9)
P2A	0.10000 (19)	0.4426 (3)	0.14929 (7)	0.0309 (6)	0.764 (5)
F7A	0.2000 (4)	0.5490 (5)	0.12970 (15)	0.0399 (12)	0.764 (5)
F8A	0.1804 (6)	0.3256 (6)	0.1277 (3)	0.079 (2)	0.764 (5)
F9A	0.0039 (8)	0.3374 (6)	0.1711 (3)	0.081 (2)	0.764 (5)
F10A	0.2148 (7)	0.4338 (6)	0.20314 (19)	0.0755 (19)	0.764 (5)
F11A	0.0331 (6)	0.5585 (6)	0.1761 (4)	0.099 (3)	0.764 (5)
F12A	−0.0023 (7)	0.4527 (10)	0.0967 (3)	0.127 (4)	0.764 (5)
P2B	0.0850 (6)	0.3710 (9)	0.1433 (2)	0.0242 (17)*	0.236 (5)
F7B	−0.0640 (14)	0.3262 (15)	0.1484 (5)	0.030 (3)*	0.236 (5)
F8B	0.1292 (17)	0.4035 (17)	0.2036 (6)	0.046 (4)*	0.236 (5)
F9B	0.0238 (18)	0.5234 (19)	0.1331 (7)	0.055 (5)*	0.236 (5)
F10B	0.0506 (14)	0.3422 (15)	0.0841 (5)	0.034 (3)*	0.236 (5)
F11B	0.1506 (15)	0.2290 (16)	0.1537 (6)	0.047 (4)*	0.236 (5)
F12B	0.2312 (14)	0.4321 (16)	0.1348 (5)	0.041 (4)*	0.236 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.030 (2)	0.022 (2)	0.0226 (19)	0.0010 (17)	0.0056 (16)	0.0028 (16)
N2	0.034 (2)	0.028 (2)	0.0154 (18)	0.0004 (18)	0.0001 (16)	0.0012 (16)
C1	0.025 (2)	0.023 (3)	0.026 (2)	0.0111 (19)	0.0041 (18)	−0.001 (2)
C2	0.034 (3)	0.036 (3)	0.017 (2)	0.012 (2)	0.0016 (19)	0.005 (2)
C3	0.042 (3)	0.052 (4)	0.019 (2)	0.014 (3)	0.011 (2)	−0.001 (2)
C4	0.037 (3)	0.044 (3)	0.026 (3)	0.021 (3)	0.001 (2)	−0.008 (2)
C5	0.034 (3)	0.024 (3)	0.032 (3)	0.010 (2)	−0.002 (2)	0.001 (2)
C6	0.029 (2)	0.027 (3)	0.022 (2)	0.003 (2)	0.0029 (18)	−0.005 (2)
C7	0.055 (3)	0.028 (3)	0.035 (3)	−0.013 (3)	0.020 (3)	−0.010 (2)
C8	0.027 (3)	0.039 (3)	0.046 (3)	0.001 (2)	0.006 (2)	−0.002 (3)
C9	0.030 (3)	0.044 (3)	0.028 (3)	0.001 (2)	−0.007 (2)	0.003 (2)
C10	0.029 (2)	0.024 (2)	0.015 (2)	−0.0006 (19)	0.0050 (17)	0.0024 (18)
C11	0.066 (4)	0.033 (3)	0.020 (3)	−0.005 (3)	0.018 (3)	−0.007 (2)
C12A	0.046 (6)	0.038 (6)	0.035 (5)	−0.007 (4)	0.017 (4)	−0.001 (4)
C13A	0.053 (7)	0.077 (8)	0.038 (6)	−0.005 (6)	0.016 (5)	−0.005 (5)
C14	0.042 (3)	0.043 (3)	0.021 (2)	0.005 (3)	0.000 (2)	0.010 (2)
N3A	0.034 (4)	0.025 (5)	0.026 (4)	0.000 (3)	0.009 (3)	0.003 (3)
N4A	0.030 (3)	0.025 (4)	0.037 (3)	−0.004 (3)	0.007 (3)	−0.003 (3)
C15A	0.021 (4)	0.065 (6)	0.109 (8)	−0.005 (4)	0.021 (4)	−0.049 (6)
C16A	0.022 (4)	0.058 (6)	0.099 (7)	−0.003 (4)	0.006 (4)	−0.044 (5)
C17A	0.024 (3)	0.026 (4)	0.041 (4)	−0.004 (3)	0.009 (3)	0.009 (4)
C18A	0.038 (4)	0.023 (4)	0.050 (4)	−0.003 (3)	0.001 (3)	−0.009 (3)
C19A	0.040 (4)	0.045 (5)	0.053 (5)	−0.004 (4)	0.007 (4)	−0.011 (4)
C20A	0.107 (11)	0.076 (9)	0.041 (5)	−0.039 (8)	0.016 (6)	−0.004 (5)
P1A	0.0294 (7)	0.0260 (7)	0.0402 (8)	−0.0003 (6)	0.0022 (6)	0.0082 (6)
F1A	0.150 (7)	0.056 (3)	0.067 (4)	−0.014 (4)	0.055 (4)	−0.009 (3)
F2A	0.031 (2)	0.048 (3)	0.137 (6)	0.011 (2)	0.007 (3)	0.046 (3)
F3A	0.079 (4)	0.070 (3)	0.056 (3)	−0.004 (3)	0.028 (3)	0.002 (3)
F4A	0.034 (2)	0.076 (4)	0.105 (5)	0.000 (2)	−0.015 (3)	0.037 (3)
F5	0.084 (3)	0.046 (2)	0.068 (3)	−0.031 (2)	−0.008 (2)	0.015 (2)
F6	0.0441 (19)	0.0322 (18)	0.058 (2)	−0.0076 (15)	−0.0021 (16)	0.0128 (16)
P2A	0.0319 (10)	0.0293 (14)	0.0350 (10)	0.0034 (9)	0.0153 (7)	0.0049 (9)
F7A	0.035 (2)	0.055 (3)	0.031 (2)	−0.010 (2)	0.0088 (17)	0.003 (2)
F8A	0.083 (4)	0.054 (4)	0.113 (5)	0.005 (3)	0.051 (4)	−0.025 (4)
F9A	0.104 (5)	0.070 (4)	0.087 (5)	−0.041 (4)	0.067 (4)	−0.015 (4)
F10A	0.097 (5)	0.082 (4)	0.039 (3)	−0.017 (4)	−0.008 (3)	0.025 (3)
F11A	0.057 (3)	0.063 (4)	0.198 (8)	−0.008 (3)	0.082 (4)	−0.032 (5)
F12A	0.086 (5)	0.165 (8)	0.095 (5)	−0.078 (5)	−0.070 (4)	0.070 (6)

Geometric parameters (Å, º) top

N1—C10	1.335 (6)	C15A—H15A	0.9300
N1—C8	1.381 (6)	C16A—H16A	0.9300
N1—C7	1.462 (6)	C17A—H17A	0.9300
N2—C10	1.323 (6)	C18A—C19A	1.487 (11)
N2—C9	1.370 (7)	C18A—H18A	0.9700
N2—C11	1.486 (6)	C18A—H18B	0.9700
C1—C6	1.385 (7)	C19A—C20A	1.303 (14)
C1—C2	1.386 (6)	C19A—H19A	0.9300
C1—H1A	0.9300	C20A—H20A	0.9300
C2—C3	1.383 (7)	C20A—H20B	0.9300
C2—C14	1.506 (7)	N3B—C15B	1.35 (5)
C3—C4	1.380 (8)	N3B—C17B	1.37 (4)
C3—H3A	0.9300	N4B—C17B	1.30 (3)
C4—C5	1.379 (7)	N4B—C16B	1.35 (4)
C4—H4A	0.9300	N4B—C18B	1.48 (3)
C5—C6	1.395 (7)	C15B—C16B	1.35 (4)
C5—H5A	0.9300	C15B—H15B	0.9300
C6—C7	1.517 (7)	C16B—H16B	0.9300
C7—H7A	0.9700	C17B—H17B	0.9300
C7—H7B	0.9700	C18B—C19B	1.45 (3)
C8—C9	1.344 (8)	C18B—H18C	0.9700
C8—H8A	0.9300	C18B—H18D	0.9700
C9—H9A	0.9300	C19B—C20B	1.32 (5)
C10—H10A	0.9300	C19B—H19B	0.9300
C11—C12B	1.343 (18)	C20B—H20C	0.9300
C11—C12A	1.570 (11)	C20B—H20D	0.9300
C11—H11A	0.9700	P1A—F3B	1.52 (2)
C11—H11B	0.9700	P1A—F2B	1.55 (2)
C11—H11C	0.9600	P1A—F1A	1.558 (5)
C11—H11D	0.9601	P1A—F5	1.586 (4)
C12A—C13A	1.294 (17)	P1A—F4B	1.587 (18)
C12A—H12A	0.9300	P1A—F6	1.588 (3)
C13A—H13A	0.9300	P1A—F2A	1.592 (4)
C13A—H13B	0.9300	P1A—F4A	1.597 (5)
C12B—C13B	1.32 (3)	P1A—F3A	1.606 (5)
C12B—H12B	0.9300	P1A—F1B	1.69 (2)
C13B—H13C	0.9300	P2A—F12A	1.543 (5)
C13B—H13D	0.9300	P2A—F11A	1.557 (6)
C14—N3A	1.422 (10)	P2A—F8A	1.570 (6)
C14—N3B	1.71 (3)	P2A—F9A	1.587 (5)
C14—H14A	0.9700	P2A—F7A	1.595 (4)
C14—H14B	0.9700	P2A—F10A	1.629 (5)
N3A—C17A	1.319 (11)	P2B—F10B	1.543 (14)
N3A—C15A	1.380 (11)	P2B—F11B	1.552 (17)
N4A—C17A	1.332 (9)	P2B—F7B	1.567 (15)
N4A—C16A	1.354 (10)	P2B—F8B	1.586 (17)
N4A—C18A	1.482 (9)	P2B—F12B	1.620 (15)
C15A—C16A	1.335 (11)	P2B—F9B	1.628 (19)

C10—N1—C8	107.8 (4)	C19A—C20A—H20A	120.0
C10—N1—C7	124.6 (4)	C19A—C20A—H20B	120.0
C8—N1—C7	127.4 (4)	H20A—C20A—H20B	120.0
C10—N2—C9	108.4 (4)	C15B—N3B—C17B	103 (3)
C10—N2—C11	125.8 (4)	C15B—N3B—C14	132 (3)
C9—N2—C11	125.7 (4)	C17B—N3B—C14	125 (3)
C6—C1—C2	120.1 (4)	C17B—N4B—C16B	111 (2)
C6—C1—H1A	120.0	C17B—N4B—C18B	127 (2)
C2—C1—H1A	120.0	C16B—N4B—C18B	121 (2)
C3—C2—C1	119.5 (5)	C16B—C15B—N3B	112 (3)
C3—C2—C14	121.3 (5)	C16B—C15B—H15B	123.8
C1—C2—C14	119.2 (5)	N3B—C15B—H15B	123.8
C4—C3—C2	120.8 (5)	C15B—C16B—N4B	104 (3)
C4—C3—H3A	119.6	C15B—C16B—H16B	128.1
C2—C3—H3A	119.6	N4B—C16B—H16B	128.1
C5—C4—C3	119.9 (5)	N4B—C17B—N3B	110 (2)
C5—C4—H4A	120.0	N4B—C17B—H17B	125.0
C3—C4—H4A	120.0	N3B—C17B—H17B	125.0
C4—C5—C6	119.8 (5)	C19B—C18B—N4B	114 (2)
C4—C5—H5A	120.1	C19B—C18B—H18C	108.7
C6—C5—H5A	120.1	N4B—C18B—H18C	108.7
C1—C6—C5	119.9 (4)	C19B—C18B—H18D	108.7
C1—C6—C7	121.6 (4)	N4B—C18B—H18D	108.7
C5—C6—C7	118.3 (5)	H18C—C18B—H18D	107.6
N1—C7—C6	112.4 (4)	C20B—C19B—C18B	127 (3)
N1—C7—H7A	109.1	C20B—C19B—H19B	116.6
C6—C7—H7A	109.1	C18B—C19B—H19B	116.6
N1—C7—H7B	109.1	C19B—C20B—H20C	120.0
C6—C7—H7B	109.1	C19B—C20B—H20D	120.0
H7A—C7—H7B	107.9	H20C—C20B—H20D	120.0
C9—C8—N1	107.1 (5)	F3B—P1A—F2B	90.9 (13)
C9—C8—H8A	126.4	F3B—P1A—F1A	141.7 (10)
N1—C8—H8A	126.4	F2B—P1A—F1A	126.4 (10)
C8—C9—N2	107.6 (5)	F3B—P1A—F5	80.5 (9)
C8—C9—H9A	126.2	F2B—P1A—F5	92.6 (9)
N2—C9—H9A	126.2	F1A—P1A—F5	88.9 (3)
N2—C10—N1	109.1 (4)	F3B—P1A—F4B	91.7 (12)
N2—C10—H10A	125.5	F2B—P1A—F4B	176.8 (12)
N1—C10—H10A	125.5	F1A—P1A—F4B	50.7 (7)
C12B—C11—N2	114.1 (8)	F5—P1A—F4B	86.0 (7)
N2—C11—C12A	110.2 (5)	F3B—P1A—F6	99.3 (9)
C12B—C11—H11A	82.7	F2B—P1A—F6	87.0 (8)
N2—C11—H11A	109.6	F1A—P1A—F6	91.5 (3)
C12A—C11—H11A	109.6	F5—P1A—F6	179.5 (2)
C12B—C11—H11B	127.9	F4B—P1A—F6	94.4 (7)
N2—C11—H11B	109.6	F3B—P1A—F2A	122.9 (10)
C12A—C11—H11B	109.6	F1A—P1A—F2A	93.3 (4)
H11A—C11—H11B	108.1	F5—P1A—F2A	89.1 (2)
C12B—C11—H11C	108.9	F4B—P1A—F2A	143.7 (8)
N2—C11—H11C	108.1	F6—P1A—F2A	90.7 (2)
C12A—C11—H11C	132.5	F3B—P1A—F4A	53.8 (10)
H11B—C11—H11C	82.0	F2B—P1A—F4A	142.9 (10)
C12B—C11—H11D	108.9	F1A—P1A—F4A	90.4 (4)
N2—C11—H11D	109.0	F5—P1A—F4A	92.3 (3)
C12A—C11—H11D	85.1	F6—P1A—F4A	87.9 (2)
H11A—C11—H11D	130.0	F2A—P1A—F4A	176.0 (4)
H11C—C11—H11D	107.7	F2B—P1A—F3A	54.9 (9)
C13A—C12A—C11	124.9 (11)	F1A—P1A—F3A	178.6 (4)
C13A—C12A—H12A	117.6	F5—P1A—F3A	90.7 (3)
C11—C12A—H12A	117.6	F4B—P1A—F3A	127.9 (8)
C12A—C13A—H13A	120.0	F6—P1A—F3A	88.9 (2)
C12A—C13A—H13B	120.0	F2A—P1A—F3A	88.0 (3)
H13A—C13A—H13B	120.0	F4A—P1A—F3A	88.2 (3)
C13B—C12B—C11	122 (2)	F3B—P1A—F1B	177.8 (13)
C13B—C12B—H12B	119.0	F2B—P1A—F1B	91.2 (12)
C11—C12B—H12B	119.0	F5—P1A—F1B	98.6 (9)
C12B—C13B—H13C	120.0	F4B—P1A—F1B	86.1 (11)
C12B—C13B—H13D	120.0	F6—P1A—F1B	81.7 (9)
H13C—C13B—H13D	120.0	F2A—P1A—F1B	59.1 (9)
N3A—C14—C2	108.9 (5)	F4A—P1A—F1B	124.3 (9)
C2—C14—N3B	114.6 (12)	F3A—P1A—F1B	145.4 (9)
N3A—C14—H14A	109.9	F12A—P2A—F11A	95.2 (5)
C2—C14—H14A	109.9	F12A—P2A—F8A	91.0 (5)
N3B—C14—H14A	115.0	F11A—P2A—F8A	173.8 (4)
N3A—C14—H14B	109.9	F12A—P2A—F9A	91.6 (4)
C2—C14—H14B	109.9	F11A—P2A—F9A	89.3 (3)
N3B—C14—H14B	98.2	F8A—P2A—F9A	91.3 (4)
H14A—C14—H14B	108.3	F12A—P2A—F7A	90.6 (3)
C17A—N3A—C15A	108.7 (7)	F11A—P2A—F7A	90.0 (3)
C17A—N3A—C14	124.2 (7)	F8A—P2A—F7A	89.2 (3)
C15A—N3A—C14	127.1 (8)	F9A—P2A—F7A	177.7 (3)
C17A—N4A—C16A	108.3 (7)	F12A—P2A—F10A	176.9 (4)
C17A—N4A—C18A	126.2 (7)	F11A—P2A—F10A	86.3 (4)
C16A—N4A—C18A	125.3 (6)	F8A—P2A—F10A	87.5 (4)
C16A—C15A—N3A	106.2 (7)	F9A—P2A—F10A	91.1 (4)
C16A—C15A—H15A	126.9	F7A—P2A—F10A	86.7 (3)
N3A—C15A—H15A	126.9	F10B—P2B—F11B	90.6 (9)
C15A—C16A—N4A	108.4 (7)	F10B—P2B—F7B	90.3 (8)
C15A—C16A—H16A	125.8	F11B—P2B—F7B	95.5 (9)
N4A—C16A—H16A	125.8	F10B—P2B—F8B	176.6 (9)
N3A—C17A—N4A	108.4 (7)	F11B—P2B—F8B	89.1 (8)
N3A—C17A—H17A	125.8	F7B—P2B—F8B	93.1 (8)
N4A—C17A—H17A	125.8	F10B—P2B—F12B	87.8 (7)
N4A—C18A—C19A	111.5 (6)	F11B—P2B—F12B	90.6 (8)
N4A—C18A—H18A	109.3	F7B—P2B—F12B	173.7 (9)
C19A—C18A—H18A	109.3	F8B—P2B—F12B	88.8 (8)
N4A—C18A—H18B	109.3	F10B—P2B—F9B	90.3 (9)
C19A—C18A—H18B	109.3	F11B—P2B—F9B	177.1 (10)
H18A—C18A—H18B	108.0	F7B—P2B—F9B	87.2 (9)
C20A—C19A—C18A	128.4 (8)	F8B—P2B—F9B	89.8 (10)
C20A—C19A—H19A	115.8	F12B—P2B—F9B	86.8 (9)
C18A—C19A—H19A	115.8

C6—C1—C2—C3	1.3 (7)	C3—C2—C14—N3B	−112.3 (13)
C6—C1—C2—C14	−179.2 (5)	C1—C2—C14—N3B	68.2 (14)
C1—C2—C3—C4	−0.9 (8)	C2—C14—N3A—C17A	−120.4 (7)
C14—C2—C3—C4	179.7 (5)	N3B—C14—N3A—C17A	1 (6)
C2—C3—C4—C5	−0.1 (8)	C2—C14—N3A—C15A	57.2 (10)
C3—C4—C5—C6	0.6 (8)	C17A—N3A—C15A—C16A	−1.1 (11)
C2—C1—C6—C5	−0.9 (7)	C14—N3A—C15A—C16A	−179.1 (8)
C2—C1—C6—C7	−177.2 (5)	N3A—C15A—C16A—N4A	0.5 (12)
C4—C5—C6—C1	−0.1 (7)	C17A—N4A—C16A—C15A	0.4 (12)
C4—C5—C6—C7	176.4 (5)	C18A—N4A—C16A—C15A	174.9 (8)
C10—N1—C7—C6	133.8 (5)	C15A—N3A—C17A—N4A	1.4 (9)
C8—N1—C7—C6	−51.7 (7)	C14—N3A—C17A—N4A	179.4 (7)
C1—C6—C7—N1	−45.3 (7)	C16A—N4A—C17A—N3A	−1.1 (9)
C5—C6—C7—N1	138.3 (5)	C18A—N4A—C17A—N3A	−175.5 (7)
C10—N1—C8—C9	0.4 (6)	C17A—N4A—C18A—C19A	87.4 (10)
C7—N1—C8—C9	−174.8 (5)	C16A—N4A—C18A—C19A	−86.1 (10)
N1—C8—C9—N2	0.2 (6)	N4A—C18A—C19A—C20A	3.4 (14)
C10—N2—C9—C8	−0.7 (6)	N3A—C14—N3B—C15B	133 (9)
C11—N2—C9—C8	−178.5 (5)	C2—C14—N3B—C15B	−164 (3)
C9—N2—C10—N1	1.0 (5)	N3A—C14—N3B—C17B	−47 (6)
C11—N2—C10—N1	178.7 (4)	C2—C14—N3B—C17B	15 (3)
C8—N1—C10—N2	−0.9 (5)	C17B—N3B—C15B—C16B	−2 (4)
C7—N1—C10—N2	174.5 (4)	C14—N3B—C15B—C16B	178 (3)
C10—N2—C11—C12B	−6.5 (13)	N3B—C15B—C16B—N4B	2 (4)
C9—N2—C11—C12B	170.9 (12)	C17B—N4B—C16B—C15B	−2 (3)
C10—N2—C11—C12A	23.7 (8)	C18B—N4B—C16B—C15B	−171 (2)
C9—N2—C11—C12A	−159.0 (6)	C16B—N4B—C17B—N3B	1 (3)
C12B—C11—C12A—C13A	−3.5 (16)	C18B—N4B—C17B—N3B	169 (2)
N2—C11—C12A—C13A	−107.0 (9)	C15B—N3B—C17B—N4B	1 (3)
N2—C11—C12B—C13B	99.6 (18)	C14—N3B—C17B—N4B	−179 (2)
C12A—C11—C12B—C13B	11.5 (14)	C17B—N4B—C18B—C19B	−90 (3)
C3—C2—C14—N3A	−101.3 (6)	C16B—N4B—C18B—C19B	78 (3)
C1—C2—C14—N3A	79.2 (7)	N4B—C18B—C19B—C20B	−2 (4)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the N3A/N4A/C15A–C17A and N3B/N4B/C15B–C17B rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···F7Aⁱ	0.93	2.40	3.276 (6)	156
C5—H5A···F5ⁱⁱ	0.93	2.51	3.320 (6)	146
C8—H8A···F11Aⁱⁱⁱ	0.93	2.27	3.107 (8)	150
C10—H10A···F7A	0.93	2.25	3.130 (6)	158
C16A—H16A···F6ⁱⁱⁱ	0.93	2.48	3.407 (9)	172
C20A—H20A···Cg2	0.93	2.89	3.489 (11)	123
C20B—H20C···Cg3	0.93	2.84	3.44 (5)	124

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, y−1, z; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₄N₄²⁺·2PF₆⁻
M_r	610.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.8748 (4), 9.9098 (3), 26.124 (1)
β (°)	101.138 (2)
V (Å³)	2508.27 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.25 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.921, 0.924
No. of measured, independent and observed [I > 2σ(I)] reflections	35601, 5217, 4324
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.108, 0.201, 1.14
No. of reflections	5217
No. of parameters	431
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.P)² + 16.2482P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.56

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the N3A/N4A/C15A–C17A and N3B/N4B/C15B–C17B rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···F7Aⁱ	0.93	2.40	3.276 (6)	156
C5—H5A···F5ⁱⁱ	0.93	2.51	3.320 (6)	146
C8—H8A···F11Aⁱⁱⁱ	0.93	2.27	3.107 (8)	150
C10—H10A···F7A	0.93	2.25	3.130 (6)	158
C16A—H16A···F6ⁱⁱⁱ	0.93	2.48	3.407 (9)	172
C20A—H20A···Cg2	0.93	2.89	3.489 (11)	123
C20B—H20C···Cg3	0.93	2.84	3.44 (5)	124

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, y−1, z; (iii) x+1, y, z.

Footnotes

‡Thomson Reuters ResearcherID: A-5525-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

RAH, MZG and HHA thank Universiti Sains Malaysia (USM) for the FRGS fund (203/PKIMIA/671115), short term grant (304/PKIMIA/639001) and RU grants (1001/PKIMIA/813023 and 1001/PKIMIA/811157). HKF and CKQ thank USM for the Research University Grant (No. 1001/PFIZIK/811160). CKQ also thanks USM for the award of a USM fellowship.

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. CSD CrossRef Web of Science Google Scholar
Arduengo, A. J., Harlow, R. L. & Kline, M. (1991). J. Am. Chem. Soc. 113, 361–363. CSD CrossRef CAS Web of Science Google Scholar
Böhm, V. P. W., Gstöttmayr, C. W. K., Weskamp, T. & Herrmann, W. A. (2000). J. Organomet Chem. 595, 186–190. Google Scholar
Bourissou, D., Guerret, O., Gabbaï, F. P. & Bertrand, G. (2000). Chem. Rev. 100, 39–91. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Caballero, A., Dìez-Barra, E., Jalón, F. A., Merino, S. & Tejeda, J. (2001). J. Organomet. Chem. 617, 395–398. Web of Science CrossRef Google Scholar
Danopoulos, A. A., Winston, S., Gelbrich, T., Hursthouse, M. B. & Tooze, R. P. (2002). J. Chem. Soc. Chem. Commun. pp. 482–483. CrossRef Google Scholar
Dias, H. V. & Jin, W. (1994). Tetrahedron Lett. 35, 1365–1366. CrossRef CAS Web of Science Google Scholar
Haque, R. A., Washeel, A., Teoh, S. G., Quah, C. K. & Fun, H.-K. (2010). Acta Cryst. E66, o2797–o2798. Web of Science CSD CrossRef IUCr Journals Google Scholar
Herrmann, W. A., Elison, M., Fischer, J., Köcher, C. & Artus, G. R. J. (1996). Chem. Eur. J. 2, 772–779. CrossRef CAS Web of Science Google Scholar
Herrmann, W. A., Goossen, L. J. & Spiegler, M. (1997). J. Organomet. Chem. 547, 357–366. Web of Science CSD CrossRef CAS Google Scholar
Jafarpour, L. & Nolan, S. P. (2001). Adv. Organomet. Chem. 46, 181–222. CrossRef Google Scholar
Melaiye, A., Sun, Z., Hindi, K., Milsted, M., Ely, D., Reneker, D. H., Tessier, C. A. & Youngs, W. J. (2005). J. Am. Chem. Soc. 127, 2285–2291. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thompson, K. H., McNeill, J. H. & Orvig, C. (1999). Chem. Rev. 99, 2561–2572. Web of Science CrossRef PubMed CAS Google Scholar
Yang, C. & Nolan, S. P. (2001). Synlett, 10, 1539–1542. CrossRef Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 1| January 2011| Pages o80-o81

https://doi.org/10.1107/S1600536810050683

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

1,3-Bis[(3-allyl­imidazol-3-ium-1-yl)meth­yl]benzene bis­­(hexa­fluoridophosphate)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

1,3-Bis[(3-allylimidazol-3-ium-1-yl)methyl]benzene bis(hexafluoridophosphate)