3,5-Bis(3-butylimidazolium-1-ylmethyl)toluene bis(hexafluorophosphate)

Haque, R.A.; Washeel, A.; Teoh, S.G.; Quah, C.K.; Fun, H.-K.

doi:10.1107/S1600536810040055

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 11| November 2010| Pages o2797-o2798

https://doi.org/10.1107/S1600536810040055

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3,5-Bis(3-butylimidazolium-1-ylmethyl)toluene bis(hexafluorophosphate)

Rosenani A. Haque,^a Abbas Washeel,^a Siang Guan Teoh,^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 30 September 2010; accepted 7 October 2010; online 13 October 2010)

In the title compound [systematic name: 3,3′-Dibutyl-1,1′-(5-methyl-m-phenylenedimethylene)diimidazol-1-ium bis(hexafluoridophosphate)], C₂₃H₃₄N₄²⁺·2PF₆⁻, the imidazole rings are inclined at angles of 68.06 (7) and 75.05 (8)° with respect to the central benzene ring. In the crystal, molecules are linked into one-dimensional columns along [010] via weak intermolecular C—H⋯F hydrogen bonds. The crystal structure is further consolidated by weak C—H⋯π(arene) interactions. One of the n-butyl groups is disordered over two sites with refined occupancies of 0.694 (5) and 0.306 (5). In addition, four of the F atoms of one of the PF₆⁻ cations are disordered over two sites with occupancies of 0.64 (3) and 0.36 (3).

Related literature

For general background to imidazoline-2-ylidenes, see: Arduengo et al. (1991 ). For the organometallic and coordination chemistry of N-heterocyclic carbene ligands, see: Chen et al. (2002 ); Zhou et al. (2008 ); Hahn & Jahnke (2008 ); Danopoulos et al. (2007 ); Bourissou et al. (2000 ); McGuinness & Cavell (2000 ); Garrison et al. (2001 ). For catalytic studies related to organic synthesis, see: Cavell & McGuinness (2004 ); Liu et al. (2007 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ). For standard bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₃H₃₄N₄²⁺·2PF₆⁻
M_r = 656.48
Monoclinic, P 2₁ /c
a = 9.6207 (1) Å
b = 11.1801 (1) Å
c = 27.9277 (3) Å
β = 102.416 (1)°
V = 2933.66 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 100 K
0.49 × 0.20 × 0.14 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.890, T_max = 0.967
45569 measured reflections
10399 independent reflections
7294 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.122
S = 1.03
10399 reflections
448 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯F4	0.93	2.42	3.0154 (16)	121
C8—H8A⋯F5	0.93	2.39	3.2700 (16)	157
C16—H16A⋯F3	0.93	2.31	3.1941 (16)	160
C16—H16A⋯F4	0.93	2.45	3.1677 (16)	134
C21A—H21B⋯F4	0.97	2.49	3.196 (2)	130
C3—H3A⋯F12ⁱ	0.93	2.44	3.3147 (16)	157
C5—H5A⋯F9Aⁱⁱ	0.93	2.55	3.420 (8)	156
C7—H7A⋯F10Aⁱⁱ	0.97	2.51	3.427 (6)	158
C9—H9A⋯F12ⁱⁱⁱ	0.93	2.48	3.2805 (17)	144
C12—H12A⋯F3^iv	0.97	2.53	3.3358 (18)	140
C18—H18A⋯F8A^v	0.93	2.38	3.148 (11)	140
C22A—H22C⋯Cg1^vi	0.96	2.76	3.535 (3)	138
C23—H23B⋯Cg1^vii	0.96	2.59	3.487 (2)	155
C22B—H22E⋯Cg1^vi	0.96	2.86	3.637 (8)	139
Symmetry codes: (i) x-1, y+1, z; (ii) x-1, y, z; (iii) -x+1, -y+1, -z+2; (iv) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (v) -x+1, -y+2, -z+2; (vi) x+1, y, z; (vii) -x, -y+2, -z+2.

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/S1600536810040055/lh5143sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810040055/lh5143Isup2.hkl

checkCIF report

Comment top

Since the discovery of stable imidazoline-2-ylidenes, which were isolated and structurally characterized by Arduengo et al. (1991), the organometallic and coordination chemistry of N-heterocyclic carbene (NHC) ligands have been receiving great attention in recent years and much interest has been generated in the chemistry of the metal complexes of these ligands (Chen et al., 2002; Zhou et al., 2008). NHC carbene, a strong σ-donor and a weak π-acceptor, strongly interacts with different transitions metals in various oxidation states (Hahn & Jahnke, 2008; Danopoulos et al., 2007). Heterocyclic carbenes derived from imidazolium ions form complexes with many transition metals; heterocyclic carbene complexes of Pd, Ni, Pt, Rh, Ru, Ag and Au have been reported (Bourissou et al., 2000; McGuinness & Cavell, 2000; Garrison et al., 2001). Extensive catalytic studies on the application to organic synthesis have also been reported (Cavell & McGuinness, 2004; Liu et al., 2007).

The title molecule (Fig. 1) consists of a 3,5-bis(3-butylimidazolium-1- ylmethyl)toluene cation and two hexafluorophosphate anions. Bond lengths (Allen et al., 1987) and angles are within normal ranges.The phenyl ring (C1-C6) is inclined at angles of 68.06 (7) and 75.05 (8) ° with respect to the N1/N2/C8/C9/C10 and N3/N4/C16/C17/C18 imidazole rings. The butyl group (C19-C22) of the cation and four fluorine atoms (F7-F10) of the hexafluorophosphate anion are disordered over two positions with refined site-occupancies of 0.694 (5) : 0.306 (5) and 0.64 (3) : 0.36 (3), respectively.

In the crystal structure, (Fig. 2), the molecules are linked into one-dimensional columns along [010] via intermolecular C–H···F hydrogen bonds (Table 1). The crystal structure is further consolidated by C–H···Cg1 (Table 1) interactions, Cg1 is the centroid of C1-C6 phenyl ring.

Related literature top

For general background to imidazoline-2-ylidenes, see: Arduengo et al. (1991). For the organometallic and coordination chemistry of N-heterocyclic carbene ligands, see: Chen et al. (2002); Zhou et al. (2008); Hahn & Jahnke (2008); Danopoulos et al. (2007); Bourissou et al. (2000); McGuinness & Cavell (2000); Garrison et al. (2001). For catalytic studies related to organic synthesis, see: Cavell & McGuinness (2004); Liu et al. (2007). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For standard bond-length data, see: Allen et al. (1987).

For related literature, see: Bourissou et al. (2000).

Experimental top

N-butylimidazole (0.9 g, 7.2 mmol) was added to a stirred solution of 3,5-bis(bromomethyl)toluene (1.0 g, 3.6 mmol) in 20 ml of 1,4-dioxane. The mixture was refluxed at 373 K for 24 h. The sticky product was isolated by decantation and washed with fresh 1,4-dioxane (2 x 5 ml) and diethyl ether (2 x 3 ml). The resulting bromide salt was converted directly to its hexafluorophosphate salt by metathesis reaction using KPF₆ (1.3 g, 7.2 mmol) in 20 ml of methanol. The colourless precipitate formed was collected and washed with distilled water (2 x 5 ml), and then recrystallized from acetonitrile to give colourless crystals. Yield: 1.9 g (79%), m. p.: 369-371 K. Crystals suitable for X-ray diffraction studies were obtained by slow evaporation of the salt solution in acetonitrile at 281 K.

Structure description top

For general background to imidazoline-2-ylidenes, see: Arduengo et al. (1991). For the organometallic and coordination chemistry of N-heterocyclic carbene ligands, see: Chen et al. (2002); Zhou et al. (2008); Hahn & Jahnke (2008); Danopoulos et al. (2007); Bourissou et al. (2000); McGuinness & Cavell (2000); Garrison et al. (2001). For catalytic studies related to organic synthesis, see: Cavell & McGuinness (2004); Liu et al. (2007). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For standard bond-length data, see: Allen et al. (1987).

For related literature, see: Bourissou et al. (2000).

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 disorder components are shown.
	Fig. 2. Part of the crystal structure of the title compound, viewed along the b axis. Only the major disorder component is shown. Intermolecular hydrogen bonds are shown in dashed lines.

3,3'-Dibutyl-1,1'-(5-methyl-m-phenylenedimethylene)diimidazol-1-ium bis(hexafluoridophosphate) top

Crystal data top

C₂₃H₃₄N₄²⁺·2PF₆⁻	F(000) = 1352
M_r = 656.48	D_x = 1.486 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9893 reflections
a = 9.6207 (1) Å	θ = 2.2–32.2°
b = 11.1801 (1) Å	µ = 0.25 mm⁻¹
c = 27.9277 (3) Å	T = 100 K
β = 102.416 (1)°	Block, colourless
V = 2933.66 (5) Å³	0.49 × 0.20 × 0.14 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	10399 independent reflections
Radiation source: fine-focus sealed tube	7294 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
φ and ω scans	θ_max = 32.3°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
T_min = 0.890, T_max = 0.967	k = −15→16
45569 measured reflections	l = −41→41

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0569P)² + 0.5709P] where P = (F_o² + 2F_c²)/3
10399 reflections	(Δ/σ)_max = 0.001
448 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₃H₃₄N₄²⁺·2PF₆⁻	V = 2933.66 (5) Å³
M_r = 656.48	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.6207 (1) Å	µ = 0.25 mm⁻¹
b = 11.1801 (1) Å	T = 100 K
c = 27.9277 (3) Å	0.49 × 0.20 × 0.14 mm
β = 102.416 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	10399 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	7294 reflections with I > 2σ(I)
T_min = 0.890, T_max = 0.967	R_int = 0.040
45569 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.03	Δρ_max = 0.39 e Å⁻³
10399 reflections	Δρ_min = −0.26 e Å⁻³
448 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.04726 (12)	0.72856 (9)	0.87680 (4)	0.0197 (2)
N2	0.25427 (13)	0.70746 (10)	0.85917 (4)	0.0242 (2)
N3	0.01110 (12)	1.25423 (9)	0.87615 (4)	0.0192 (2)
N4	0.22616 (13)	1.27303 (12)	0.86629 (5)	0.0289 (3)
C1	−0.12271 (14)	0.98508 (11)	0.87153 (5)	0.0201 (3)
H1A	−0.1079	0.9856	0.8397	0.024*
C2	−0.14332 (14)	1.09268 (11)	0.89438 (5)	0.0203 (2)
C3	−0.16796 (15)	1.09046 (12)	0.94182 (5)	0.0241 (3)
H3A	−0.1824	1.1620	0.9570	0.029*
C4	−0.17140 (17)	0.98323 (12)	0.96688 (6)	0.0262 (3)
C5	−0.14902 (16)	0.87688 (12)	0.94368 (5)	0.0257 (3)
H5A	−0.1506	0.8047	0.9601	0.031*
C6	−0.12428 (14)	0.87685 (11)	0.89618 (5)	0.0209 (3)
C7	−0.10445 (14)	0.75962 (12)	0.87112 (5)	0.0230 (3)
H7A	−0.1524	0.6963	0.8850	0.028*
H7B	−0.1480	0.7657	0.8365	0.028*
C8	0.12152 (15)	0.74404 (12)	0.84230 (5)	0.0219 (3)
H8A	0.0861	0.7755	0.8112	0.026*
C9	0.13609 (16)	0.67800 (12)	0.91727 (5)	0.0258 (3)
H9A	0.1115	0.6571	0.9466	0.031*
C10	0.26525 (16)	0.66465 (13)	0.90628 (5)	0.0272 (3)
H10A	0.3462	0.6327	0.9265	0.033*
C11	0.36527 (17)	0.70733 (14)	0.83004 (6)	0.0322 (3)
H11A	0.4518	0.7418	0.8495	0.039*
H11B	0.3345	0.7573	0.8013	0.039*
C12	0.39714 (16)	0.58281 (14)	0.81384 (6)	0.0296 (3)
H12A	0.3086	0.5432	0.7991	0.035*
H12B	0.4430	0.5366	0.8423	0.035*
C13	0.4934 (2)	0.58630 (18)	0.77702 (8)	0.0466 (5)
H13A	0.4506	0.6373	0.7497	0.056*
H13B	0.5843	0.6210	0.7926	0.056*
C14	0.5180 (2)	0.4634 (2)	0.75778 (8)	0.0551 (5)
H14A	0.5779	0.4700	0.7345	0.083*
H14B	0.4283	0.4289	0.7421	0.083*
H14C	0.5633	0.4133	0.7845	0.083*
C15	−0.13694 (14)	1.21063 (12)	0.86830 (5)	0.0223 (3)
H15A	−0.1752	1.2004	0.8335	0.027*
H15B	−0.1949	1.2693	0.8805	0.027*
C16	0.09876 (15)	1.22892 (12)	0.84694 (5)	0.0222 (3)
H16A	0.0747	1.1869	0.8176	0.027*
C17	0.08522 (17)	1.31852 (12)	0.91586 (5)	0.0270 (3)
H17A	0.0493	1.3482	0.9419	0.032*
C18	0.21968 (18)	1.32975 (14)	0.90954 (6)	0.0323 (3)
H18A	0.2942	1.3686	0.9305	0.039*
C19A	0.3539 (4)	1.2443 (3)	0.84464 (16)	0.0311 (7)	0.694 (5)
H19A	0.4058	1.3175	0.8418	0.047*	0.694 (5)
H19B	0.3214	1.2117	0.8120	0.047*	0.694 (5)
C20A	0.4534 (3)	1.1550 (2)	0.87594 (12)	0.0333 (7)	0.694 (5)
H20A	0.4875	1.1894	0.9082	0.040*	0.694 (5)
H20B	0.5352	1.1428	0.8614	0.040*	0.694 (5)
C21A	0.3866 (2)	1.0333 (2)	0.88191 (8)	0.0271 (6)	0.694 (5)
H21A	0.3007	1.0451	0.8942	0.041*	0.694 (5)
H21B	0.3600	0.9950	0.8501	0.041*	0.694 (5)
C22A	0.4863 (3)	0.9528 (3)	0.91641 (12)	0.0333 (6)	0.694 (5)
H22A	0.4374	0.8806	0.9215	0.040*	0.694 (5)
H22B	0.5185	0.9928	0.9472	0.040*	0.694 (5)
H22C	0.5666	0.9335	0.9025	0.040*	0.694 (5)
C19B	0.3518 (10)	1.2886 (6)	0.8487 (4)	0.0292 (15)	0.306 (5)
H19C	0.4196	1.3384	0.8707	0.044*	0.306 (5)
H19D	0.3316	1.3243	0.8163	0.044*	0.306 (5)
C20B	0.4073 (6)	1.1615 (5)	0.8473 (2)	0.0280 (13)	0.306 (5)
H20C	0.4935	1.1632	0.8346	0.034*	0.306 (5)
H20D	0.3372	1.1145	0.8249	0.034*	0.306 (5)
C21B	0.4395 (6)	1.1003 (5)	0.8976 (2)	0.0306 (14)	0.306 (5)
H21C	0.5222	1.1373	0.9183	0.046*	0.306 (5)
H21D	0.3594	1.1108	0.9131	0.046*	0.306 (5)
C22B	0.4668 (8)	0.9706 (7)	0.8925 (4)	0.049 (2)	0.306 (5)
H22D	0.4743	0.9320	0.9237	0.058*	0.306 (5)
H22E	0.5541	0.9602	0.8816	0.058*	0.306 (5)
H22F	0.3898	0.9359	0.8691	0.058*	0.306 (5)
C23	−0.2051 (2)	0.98208 (14)	1.01718 (6)	0.0348 (4)
H23A	−0.2508	1.0557	1.0225	0.052*
H23B	−0.1185	0.9735	1.0415	0.052*
H23C	−0.2673	0.9162	1.0196	0.052*
P1	0.03700 (4)	0.98649 (3)	0.736481 (13)	0.02052 (8)
F1	0.14427 (10)	1.08561 (8)	0.72469 (3)	0.0333 (2)
F2	0.13549 (10)	0.88117 (8)	0.72386 (3)	0.0322 (2)
F3	−0.06262 (9)	1.09104 (7)	0.75081 (3)	0.02749 (18)
F4	0.12345 (10)	0.98346 (7)	0.79273 (3)	0.0288 (2)
F5	−0.07193 (9)	0.88809 (8)	0.74956 (3)	0.02905 (19)
F6	−0.05042 (10)	0.98987 (7)	0.68110 (3)	0.02762 (19)
P2	0.70821 (4)	0.49928 (3)	0.947765 (13)	0.02189 (8)
F7A	0.5758 (12)	0.4191 (10)	0.9282 (3)	0.078 (2)	0.64 (3)
F8A	0.6652 (12)	0.5050 (9)	0.9993 (4)	0.0473 (18)	0.64 (3)
F9A	0.8492 (8)	0.5779 (7)	0.9694 (3)	0.0372 (10)	0.64 (3)
F10A	0.7584 (13)	0.4898 (3)	0.8965 (2)	0.0429 (14)	0.64 (3)
F7B	0.5535 (12)	0.4370 (13)	0.9296 (4)	0.052 (2)	0.36 (3)
F8B	0.689 (2)	0.5172 (17)	1.0023 (7)	0.050 (3)	0.36 (3)
F9B	0.8528 (13)	0.5644 (17)	0.9618 (8)	0.053 (3)	0.36 (3)
F10B	0.7239 (19)	0.4851 (9)	0.8938 (4)	0.056 (3)	0.36 (3)
F11	0.62602 (11)	0.62115 (9)	0.93069 (4)	0.0452 (3)
F12	0.79372 (13)	0.37811 (8)	0.96468 (4)	0.0462 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0263 (6)	0.0145 (5)	0.0190 (5)	0.0008 (4)	0.0065 (4)	−0.0006 (4)
N2	0.0266 (6)	0.0214 (5)	0.0256 (6)	0.0007 (5)	0.0077 (5)	0.0003 (5)
N3	0.0255 (6)	0.0136 (5)	0.0181 (5)	−0.0010 (4)	0.0040 (4)	0.0006 (4)
N4	0.0256 (6)	0.0331 (7)	0.0261 (6)	−0.0044 (5)	0.0013 (5)	0.0069 (5)
C1	0.0220 (6)	0.0206 (6)	0.0192 (6)	−0.0008 (5)	0.0080 (5)	−0.0014 (5)
C2	0.0231 (6)	0.0169 (5)	0.0221 (6)	0.0001 (5)	0.0075 (5)	0.0001 (5)
C3	0.0312 (7)	0.0176 (6)	0.0268 (7)	0.0000 (5)	0.0133 (6)	−0.0024 (5)
C4	0.0362 (8)	0.0212 (6)	0.0252 (7)	−0.0007 (5)	0.0159 (6)	−0.0009 (5)
C5	0.0352 (8)	0.0182 (6)	0.0269 (7)	−0.0015 (5)	0.0137 (6)	0.0022 (5)
C6	0.0235 (6)	0.0171 (6)	0.0238 (7)	−0.0005 (5)	0.0091 (5)	−0.0021 (5)
C7	0.0249 (7)	0.0180 (6)	0.0278 (7)	−0.0005 (5)	0.0097 (6)	−0.0027 (5)
C8	0.0287 (7)	0.0177 (6)	0.0196 (6)	0.0003 (5)	0.0060 (5)	0.0002 (5)
C9	0.0381 (8)	0.0210 (6)	0.0180 (6)	0.0027 (6)	0.0055 (6)	0.0025 (5)
C10	0.0322 (8)	0.0238 (7)	0.0238 (7)	0.0037 (6)	0.0025 (6)	0.0020 (5)
C11	0.0287 (8)	0.0318 (8)	0.0400 (9)	−0.0006 (6)	0.0160 (7)	0.0007 (7)
C12	0.0237 (7)	0.0362 (8)	0.0298 (8)	0.0016 (6)	0.0078 (6)	−0.0029 (6)
C13	0.0449 (10)	0.0491 (11)	0.0542 (12)	0.0066 (9)	0.0292 (9)	0.0007 (9)
C14	0.0530 (12)	0.0621 (13)	0.0593 (14)	0.0055 (10)	0.0320 (11)	−0.0127 (11)
C15	0.0240 (6)	0.0191 (6)	0.0244 (7)	0.0023 (5)	0.0065 (5)	0.0038 (5)
C16	0.0265 (7)	0.0204 (6)	0.0192 (6)	0.0005 (5)	0.0038 (5)	0.0005 (5)
C17	0.0444 (9)	0.0164 (6)	0.0182 (6)	−0.0023 (6)	0.0022 (6)	−0.0024 (5)
C18	0.0410 (9)	0.0254 (7)	0.0254 (7)	−0.0105 (6)	−0.0039 (6)	0.0028 (6)
C19A	0.0258 (13)	0.0306 (18)	0.0399 (16)	−0.0018 (16)	0.0136 (11)	0.0025 (16)
C20A	0.0234 (12)	0.0317 (13)	0.0454 (19)	−0.0030 (9)	0.0088 (12)	−0.0032 (12)
C21A	0.0245 (11)	0.0269 (12)	0.0288 (11)	−0.0001 (9)	0.0034 (9)	−0.0041 (9)
C22A	0.0267 (13)	0.0304 (13)	0.0396 (16)	0.0037 (10)	0.0005 (13)	−0.0037 (13)
C19B	0.027 (3)	0.025 (3)	0.034 (3)	−0.002 (3)	0.003 (2)	0.001 (3)
C20B	0.019 (2)	0.041 (3)	0.022 (3)	−0.007 (2)	0.002 (2)	−0.002 (2)
C21B	0.023 (2)	0.028 (3)	0.043 (3)	0.004 (2)	0.014 (2)	0.010 (2)
C22B	0.031 (4)	0.038 (4)	0.072 (6)	0.004 (3)	0.000 (4)	0.015 (4)
C23	0.0534 (10)	0.0283 (7)	0.0287 (8)	0.0001 (7)	0.0223 (7)	0.0005 (6)
P1	0.02485 (18)	0.01586 (15)	0.01977 (17)	−0.00042 (12)	0.00237 (13)	−0.00059 (12)
F1	0.0344 (5)	0.0262 (4)	0.0401 (5)	−0.0078 (4)	0.0098 (4)	0.0037 (4)
F2	0.0330 (5)	0.0254 (4)	0.0368 (5)	0.0078 (4)	0.0042 (4)	−0.0055 (4)
F3	0.0323 (4)	0.0242 (4)	0.0245 (4)	0.0060 (3)	0.0028 (3)	−0.0049 (3)
F4	0.0343 (5)	0.0232 (4)	0.0236 (4)	−0.0004 (3)	−0.0055 (4)	−0.0011 (3)
F5	0.0328 (5)	0.0250 (4)	0.0279 (4)	−0.0080 (3)	0.0032 (4)	0.0026 (3)
F6	0.0398 (5)	0.0230 (4)	0.0182 (4)	0.0021 (3)	0.0021 (4)	−0.0010 (3)
P2	0.02675 (18)	0.01888 (16)	0.01996 (17)	−0.00170 (13)	0.00483 (14)	−0.00076 (13)
F7A	0.074 (4)	0.063 (3)	0.079 (3)	−0.047 (3)	−0.024 (2)	0.005 (2)
F8A	0.057 (3)	0.057 (2)	0.037 (4)	0.0006 (17)	0.031 (3)	0.003 (2)
F9A	0.039 (2)	0.0269 (14)	0.0385 (18)	−0.0080 (11)	−0.0080 (11)	−0.0024 (12)
F10A	0.084 (4)	0.0229 (17)	0.0288 (16)	0.0030 (13)	0.0279 (19)	0.0019 (9)
F7B	0.027 (3)	0.067 (4)	0.058 (4)	−0.022 (3)	0.001 (2)	0.029 (3)
F8B	0.068 (7)	0.060 (5)	0.022 (3)	0.024 (5)	0.008 (3)	−0.013 (3)
F9B	0.015 (3)	0.049 (6)	0.088 (8)	−0.007 (3)	−0.005 (4)	0.023 (5)
F10B	0.057 (5)	0.095 (7)	0.021 (2)	0.026 (3)	0.015 (2)	0.011 (3)
F11	0.0385 (6)	0.0373 (5)	0.0541 (7)	0.0151 (4)	−0.0025 (5)	0.0061 (5)
F12	0.0840 (8)	0.0214 (4)	0.0350 (5)	0.0163 (5)	0.0168 (5)	0.0048 (4)

Geometric parameters (Å, º) top

N1—C8	1.3285 (17)	C17—C18	1.349 (2)
N1—C9	1.3828 (18)	C17—H17A	0.9300
N1—C7	1.4753 (17)	C18—H18A	0.9300
N2—C8	1.3272 (18)	C19A—C20A	1.522 (5)
N2—C10	1.3825 (18)	C19A—H19A	0.9700
N2—C11	1.4751 (19)	C19A—H19B	0.9700
N3—C16	1.3238 (17)	C20A—C21A	1.528 (3)
N3—C17	1.3837 (17)	C20A—H20A	0.9700
N3—C15	1.4764 (18)	C20A—H20B	0.9700
N4—C16	1.3238 (18)	C21A—C22A	1.504 (4)
N4—C18	1.378 (2)	C21A—H21A	0.9700
N4—C19B	1.410 (10)	C21A—H21B	0.9700
N4—C19A	1.516 (4)	C22A—H22A	0.9600
C1—C6	1.3938 (18)	C22A—H22B	0.9600
C1—C2	1.3959 (17)	C22A—H22C	0.9600
C1—H1A	0.9300	C19B—C20B	1.521 (9)
C2—C3	1.3954 (18)	C19B—H19C	0.9700
C2—C15	1.5141 (18)	C19B—H19D	0.9700
C3—C4	1.3921 (19)	C20B—C21B	1.532 (8)
C3—H3A	0.9300	C20B—H20C	0.9700
C4—C5	1.3927 (19)	C20B—H20D	0.9700
C4—C23	1.508 (2)	C21B—C22B	1.485 (9)
C5—C6	1.3972 (19)	C21B—H21C	0.9700
C5—H5A	0.9300	C21B—H21D	0.9700
C6—C7	1.5170 (18)	C22B—H22D	0.9600
C7—H7A	0.9700	C22B—H22E	0.9600
C7—H7B	0.9700	C22B—H22F	0.9600
C8—H8A	0.9300	C23—H23A	0.9600
C9—C10	1.351 (2)	C23—H23B	0.9600
C9—H9A	0.9300	C23—H23C	0.9600
C10—H10A	0.9300	P1—F6	1.5941 (9)
C11—C12	1.515 (2)	P1—F1	1.5960 (9)
C11—H11A	0.9700	P1—F2	1.5976 (9)
C11—H11B	0.9700	P1—F4	1.6120 (9)
C12—C13	1.525 (2)	P1—F5	1.6145 (9)
C12—H12A	0.9700	P1—F3	1.6154 (9)
C12—H12B	0.9700	P2—F9B	1.544 (13)
C13—C14	1.512 (3)	P2—F10B	1.556 (11)
C13—H13A	0.9700	P2—F7A	1.557 (6)
C13—H13B	0.9700	P2—F8A	1.583 (9)
C14—H14A	0.9600	P2—F8B	1.584 (16)
C14—H14B	0.9600	P2—F11	1.5959 (10)
C14—H14C	0.9600	P2—F12	1.6024 (10)
C15—H15A	0.9700	P2—F10A	1.610 (6)
C15—H15B	0.9700	P2—F9A	1.620 (7)
C16—H16A	0.9300	P2—F7B	1.622 (10)

C8—N1—C9	108.18 (12)	H20A—C20A—H20B	107.5
C8—N1—C7	124.42 (12)	C22A—C21A—C20A	112.2 (2)
C9—N1—C7	127.40 (12)	C22A—C21A—H21A	109.2
C8—N2—C10	108.38 (12)	C20A—C21A—H21A	109.2
C8—N2—C11	124.06 (13)	C22A—C21A—H21B	109.2
C10—N2—C11	127.46 (13)	C20A—C21A—H21B	109.2
C16—N3—C17	108.54 (12)	H21A—C21A—H21B	107.9
C16—N3—C15	124.05 (11)	N4—C19B—C20B	103.1 (5)
C17—N3—C15	127.23 (12)	N4—C19B—H19C	111.2
C16—N4—C18	108.47 (13)	C20B—C19B—H19C	111.2
C16—N4—C19B	133.8 (4)	N4—C19B—H19D	111.2
C18—N4—C19B	116.9 (4)	C20B—C19B—H19D	111.2
C16—N4—C19A	121.1 (2)	H19C—C19B—H19D	109.1
C18—N4—C19A	129.8 (2)	C19B—C20B—C21B	113.3 (6)
C19B—N4—C19A	19.6 (3)	C19B—C20B—H20C	108.9
C6—C1—C2	120.31 (12)	C21B—C20B—H20C	108.9
C6—C1—H1A	119.8	C19B—C20B—H20D	108.9
C2—C1—H1A	119.8	C21B—C20B—H20D	108.9
C3—C2—C1	119.25 (12)	H20C—C20B—H20D	107.7
C3—C2—C15	120.34 (12)	C22B—C21B—C20B	110.8 (7)
C1—C2—C15	120.41 (12)	C22B—C21B—H21C	109.5
C4—C3—C2	121.32 (12)	C20B—C21B—H21C	109.5
C4—C3—H3A	119.3	C22B—C21B—H21D	109.5
C2—C3—H3A	119.3	C20B—C21B—H21D	109.5
C3—C4—C5	118.60 (13)	H21C—C21B—H21D	108.1
C3—C4—C23	120.58 (13)	C21B—C22B—H22D	109.5
C5—C4—C23	120.77 (13)	C21B—C22B—H22E	109.5
C4—C5—C6	121.11 (13)	H22D—C22B—H22E	109.5
C4—C5—H5A	119.4	C21B—C22B—H22F	109.5
C6—C5—H5A	119.4	H22D—C22B—H22F	109.5
C1—C6—C5	119.40 (12)	H22E—C22B—H22F	109.5
C1—C6—C7	120.42 (12)	C4—C23—H23A	109.5
C5—C6—C7	120.14 (12)	C4—C23—H23B	109.5
N1—C7—C6	111.93 (11)	H23A—C23—H23B	109.5
N1—C7—H7A	109.2	C4—C23—H23C	109.5
C6—C7—H7A	109.2	H23A—C23—H23C	109.5
N1—C7—H7B	109.2	H23B—C23—H23C	109.5
C6—C7—H7B	109.2	F6—P1—F1	90.75 (5)
H7A—C7—H7B	107.9	F6—P1—F2	91.01 (5)
N2—C8—N1	109.20 (12)	F1—P1—F2	91.48 (5)
N2—C8—H8A	125.4	F6—P1—F4	179.23 (6)
N1—C8—H8A	125.4	F1—P1—F4	89.69 (5)
C10—C9—N1	107.24 (12)	F2—P1—F4	89.61 (5)
C10—C9—H9A	126.4	F6—P1—F5	90.17 (5)
N1—C9—H9A	126.4	F1—P1—F5	178.60 (5)
C9—C10—N2	107.00 (13)	F2—P1—F5	89.56 (5)
C9—C10—H10A	126.5	F4—P1—F5	89.38 (5)
N2—C10—H10A	126.5	F6—P1—F3	90.33 (5)
N2—C11—C12	112.49 (13)	F1—P1—F3	89.61 (5)
N2—C11—H11A	109.1	F2—P1—F3	178.26 (5)
C12—C11—H11A	109.1	F4—P1—F3	89.04 (5)
N2—C11—H11B	109.1	F5—P1—F3	89.34 (5)
C12—C11—H11B	109.1	F9B—P2—F10B	91.4 (7)
H11A—C11—H11B	107.8	F9B—P2—F7A	170.0 (7)
C11—C12—C13	111.65 (14)	F10B—P2—F7A	81.0 (6)
C11—C12—H12A	109.3	F9B—P2—F8A	98.5 (9)
C13—C12—H12A	109.3	F10B—P2—F8A	170.0 (7)
C11—C12—H12B	109.3	F7A—P2—F8A	89.3 (5)
C13—C12—H12B	109.3	F9B—P2—F8B	88.8 (9)
H12A—C12—H12B	108.0	F10B—P2—F8B	178.3 (8)
C14—C13—C12	112.36 (16)	F7A—P2—F8B	99.0 (8)
C14—C13—H13A	109.1	F8A—P2—F8B	9.7 (11)
C12—C13—H13A	109.1	F9B—P2—F11	92.0 (7)
C14—C13—H13B	109.1	F10B—P2—F11	86.7 (4)
C12—C13—H13B	109.1	F7A—P2—F11	94.1 (5)
H13A—C13—H13B	107.9	F8A—P2—F11	91.6 (4)
C13—C14—H14A	109.5	F8B—P2—F11	91.6 (7)
C13—C14—H14B	109.5	F9B—P2—F12	86.9 (7)
H14A—C14—H14B	109.5	F10B—P2—F12	92.8 (4)
C13—C14—H14C	109.5	F7A—P2—F12	86.9 (5)
H14A—C14—H14C	109.5	F8A—P2—F12	89.1 (4)
H14B—C14—H14C	109.5	F8B—P2—F12	88.9 (7)
N3—C15—C2	110.71 (11)	F11—P2—F12	178.80 (7)
N3—C15—H15A	109.5	F9B—P2—F10A	80.3 (7)
C2—C15—H15A	109.5	F10B—P2—F10A	11.7 (7)
N3—C15—H15B	109.5	F7A—P2—F10A	91.7 (4)
C2—C15—H15B	109.5	F8A—P2—F10A	177.3 (5)
H15A—C15—H15B	108.1	F8B—P2—F10A	168.9 (8)
N3—C16—N4	109.00 (12)	F11—P2—F10A	90.8 (2)
N3—C16—H16A	125.5	F12—P2—F10A	88.5 (2)
N4—C16—H16A	125.5	F9B—P2—F9A	9.4 (10)
C18—C17—N3	106.69 (13)	F10B—P2—F9A	99.8 (7)
C18—C17—H17A	126.7	F7A—P2—F9A	177.6 (5)
N3—C17—H17A	126.7	F8A—P2—F9A	90.0 (5)
C17—C18—N4	107.30 (13)	F8B—P2—F9A	80.3 (9)
C17—C18—H18A	126.4	F11—P2—F9A	88.3 (3)
N4—C18—H18A	126.4	F12—P2—F9A	90.8 (3)
N4—C19A—C20A	111.9 (3)	F10A—P2—F9A	88.9 (4)
N4—C19A—H19A	109.2	F9B—P2—F7B	175.9 (8)
C20A—C19A—H19A	109.2	F10B—P2—F7B	85.8 (7)
N4—C19A—H19B	109.2	F7A—P2—F7B	10.6 (9)
C20A—C19A—H19B	109.2	F8A—P2—F7B	84.3 (6)
H19A—C19A—H19B	107.9	F8B—P2—F7B	93.9 (9)
C19A—C20A—C21A	114.8 (3)	F11—P2—F7B	84.9 (5)
C19A—C20A—H20A	108.6	F12—P2—F7B	96.2 (5)
C21A—C20A—H20A	108.6	F10A—P2—F7B	97.1 (5)
C19A—C20A—H20B	108.6	F9A—P2—F7B	170.9 (6)
C21A—C20A—H20B	108.6

C6—C1—C2—C3	−1.1 (2)	N2—C11—C12—C13	170.61 (14)
C6—C1—C2—C15	178.02 (13)	C11—C12—C13—C14	−176.02 (17)
C1—C2—C3—C4	0.4 (2)	C16—N3—C15—C2	90.70 (15)
C15—C2—C3—C4	−178.69 (14)	C17—N3—C15—C2	−83.84 (16)
C2—C3—C4—C5	0.3 (2)	C3—C2—C15—N3	92.95 (15)
C2—C3—C4—C23	−177.08 (15)	C1—C2—C15—N3	−86.17 (15)
C3—C4—C5—C6	−0.3 (2)	C17—N3—C16—N4	0.59 (15)
C23—C4—C5—C6	177.02 (15)	C15—N3—C16—N4	−174.83 (11)
C2—C1—C6—C5	1.1 (2)	C18—N4—C16—N3	−0.45 (16)
C2—C1—C6—C7	178.94 (12)	C19B—N4—C16—N3	−169.1 (5)
C4—C5—C6—C1	−0.3 (2)	C19A—N4—C16—N3	171.83 (19)
C4—C5—C6—C7	−178.22 (14)	C16—N3—C17—C18	−0.49 (15)
C8—N1—C7—C6	−101.42 (15)	C15—N3—C17—C18	174.74 (12)
C9—N1—C7—C6	79.54 (16)	N3—C17—C18—N4	0.22 (16)
C1—C6—C7—N1	86.62 (16)	C16—N4—C18—C17	0.13 (17)
C5—C6—C7—N1	−95.51 (15)	C19B—N4—C18—C17	171.0 (4)
C10—N2—C8—N1	1.08 (16)	C19A—N4—C18—C17	−171.3 (2)
C11—N2—C8—N1	177.63 (12)	C16—N4—C19A—C20A	−105.3 (3)
C9—N1—C8—N2	−0.99 (15)	C18—N4—C19A—C20A	65.2 (3)
C7—N1—C8—N2	179.81 (11)	C19B—N4—C19A—C20A	119.3 (17)
C8—N1—C9—C10	0.52 (16)	N4—C19A—C20A—C21A	61.1 (4)
C7—N1—C9—C10	179.69 (12)	C19A—C20A—C21A—C22A	−175.4 (3)
N1—C9—C10—N2	0.13 (16)	C16—N4—C19B—C20B	−72.2 (7)
C8—N2—C10—C9	−0.73 (16)	C18—N4—C19B—C20B	119.9 (5)
C11—N2—C10—C9	−177.13 (14)	C19A—N4—C19B—C20B	−15.9 (11)
C8—N2—C11—C12	−105.44 (16)	N4—C19B—C20B—C21B	−60.3 (7)
C10—N2—C11—C12	70.44 (19)	C19B—C20B—C21B—C22B	169.3 (6)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···F4	0.93	2.42	3.0154 (16)	121
C8—H8A···F5	0.93	2.39	3.2700 (16)	157
C16—H16A···F3	0.93	2.31	3.1941 (16)	160
C16—H16A···F4	0.93	2.45	3.1677 (16)	134
C21A—H21B···F4	0.97	2.49	3.196 (2)	130
C3—H3A···F12ⁱ	0.93	2.44	3.3147 (16)	157
C5—H5A···F9Aⁱⁱ	0.93	2.55	3.420 (8)	156
C7—H7A···F10Aⁱⁱ	0.97	2.51	3.427 (6)	158
C9—H9A···F12ⁱⁱⁱ	0.93	2.48	3.2805 (17)	144
C12—H12A···F3^iv	0.97	2.53	3.3358 (18)	140
C18—H18A···F8A^v	0.93	2.38	3.148 (11)	140
C22A—H22C···Cg1^vi	0.96	2.76	3.535 (3)	138
C23—H23B···Cg1^vii	0.96	2.59	3.487 (2)	155
C22B—H22E···Cg1^vi	0.96	2.86	3.637 (8)	139

Symmetry codes: (i) x−1, y+1, z; (ii) x−1, y, z; (iii) −x+1, −y+1, −z+2; (iv) −x, y−1/2, −z+3/2; (v) −x+1, −y+2, −z+2; (vi) x+1, y, z; (vii) −x, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₃H₃₄N₄²⁺·2PF₆⁻
M_r	656.48
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.6207 (1), 11.1801 (1), 27.9277 (3)
β (°)	102.416 (1)
V (Å³)	2933.66 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.49 × 0.20 × 0.14

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.890, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	45569, 10399, 7294
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.751

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.122, 1.03
No. of reflections	10399
No. of parameters	448
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.26

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···F4	0.93	2.42	3.0154 (16)	121
C8—H8A···F5	0.93	2.39	3.2700 (16)	157
C16—H16A···F3	0.93	2.31	3.1941 (16)	160
C16—H16A···F4	0.93	2.45	3.1677 (16)	134
C21A—H21B···F4	0.97	2.49	3.196 (2)	130
C3—H3A···F12ⁱ	0.93	2.44	3.3147 (16)	157
C5—H5A···F9Aⁱⁱ	0.93	2.55	3.420 (8)	156
C7—H7A···F10Aⁱⁱ	0.97	2.51	3.427 (6)	158
C9—H9A···F12ⁱⁱⁱ	0.93	2.48	3.2805 (17)	144
C12—H12A···F3^iv	0.97	2.53	3.3358 (18)	140
C18—H18A···F8A^v	0.93	2.38	3.148 (11)	140
C22A—H22C···Cg1^vi	0.96	2.76	3.535 (3)	138
C23—H23B···Cg1^vii	0.96	2.59	3.487 (2)	155
C22B—H22E···Cg1^vi	0.96	2.86	3.637 (8)	139

Symmetry codes: (i) x−1, y+1, z; (ii) x−1, y, z; (iii) −x+1, −y+1, −z+2; (iv) −x, y−1/2, −z+3/2; (v) −x+1, −y+2, −z+2; (vi) x+1, y, z; (vii) −x, −y+2, −z+2.

Footnotes

‡Thomson Reuters ResearcherID: A-5525-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

RAH, AW and SGT thank Universiti Sains Malaysia (USM) for the FRGS fund (203/PKIMIA/671115), the short term grant (304/PKIMIA/639001) and the Research University Grant (1001/PKIMIA/813023). HKF and CKQ thank USM for the Research University Grant (1001/PFIZIK/811160) and CKQ also thanks USM for a research fellowship.

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Volume 66| Part 11| November 2010| Pages o2797-o2798

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