3,3′-Dibenzyl-1,1′-[naphthalene-1,4-diylbis(methyl­ene)]di(1H-imidazol-3-ium) bis­(hexa­fluoro­phosphate)

Liu, C.-L.; Huang, K.

doi:10.1107/S1600536811032132

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2343

doi:10.1107/S1600536811032132

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3,3′-Dibenzyl-1,1′-[naphthalene-1,4-diylbis(methylene)]di(1H-imidazol-3-ium) bis(hexafluorophosphate)

Chang-Lu Liu ^a ^* and Kun Huang ^a

^aDepartment of Chemistry and Chemical Engineering, Sichuan University of Arts and Science, Dazhou 635000, People's Republic of China
^*Correspondence e-mail: dzliuchl@163.com

(Received 5 July 2011; accepted 8 August 2011; online 17 August 2011)

In the title N-heterocyclic carbene compound, C₃₂H₃₀N₄²⁺·2PF₆⁻, the mean plane of the naphthalene ring system makes dihedral angles of 79.15 (15) and 76.85 (16) with the imidazole rings and 56.15 (19) and 80.56 (16)° with the benzene rings. An intramolecular C—H⋯N hydrogen bond occurs. The crystal structure is stabilized by C—H⋯F interactions. In addition, π–π interactions [centroid–centroid distances = 3.848 (1) and 3.574 (3) Å] are observed. The nine equatorial F atoms in the two PF₆⁻ anions were disordered over two positions with occupancy ratios of 0.545 (10):0.455 (10) and 0.793 (11):0.207 (11) in the two anions.

Related literature

For the first free carbenes isolated, see: Arduengo et al. (1991 ). For the application of N-heterocyclic carbene ligands in transmetalation, see: Lin et al. (2009 ); Saito et al. (2011 ); Wang et al. (2005 ). For the synthesis of the title compound, see: Saito et al. (2011). For related structures, see: Saito et al. (2011). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₃₂H₃₀N₄²⁺·2PF₆⁻
M_r = 760.54
Monoclinic, C 2/c
a = 33.8250 (9) Å
b = 11.6062 (3) Å
c = 17.6986 (5) Å
β = 101.158 (1)°
V = 6816.8 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.20 × 0.20 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.957, T_max = 0.967
5990 measured reflections
5990 independent reflections
4848 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.163
S = 1.04
5990 reflections
534 parameters
106 restraints
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯F3ⁱ	0.93	2.41	3.229 (6)	147
C7—H7A⋯F1ⁱⁱ	0.97	2.54	3.375 (5)	144
C7—H7B⋯F2ⁱⁱⁱ	0.97	2.47	3.184 (5)	130
C9—H9⋯F4	0.93	2.45	3.358 (6)	164
C10—H10⋯F7	0.93	2.47	3.384 (10)	166
C14—H14⋯F10^iv	0.93	2.55	3.453 (11)	165
C18—H18⋯F11	0.93	2.46	3.252 (12)	143
C18—H18⋯N3	0.93	2.62	3.102 (4)	113
C23—H23⋯F4	0.93	2.37	3.241 (6)	156
C24—H24⋯F9ⁱ	0.93	2.53	3.258 (15)	136
C25—H25⋯F2^v	0.93	2.49	3.374 (6)	158
Symmetry codes: (i) $[x, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y-1, z; (iv) x, y+1, z; (v) $[x, -y+2, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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/S1600536811032132/su2293sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811032132/su2293Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811032132/su2293Isup3.cml

checkCIF report

Comment top

Two decades have passed since the first free N-heterocyclic carbene (NHC) was disclosed by Arduengo and coworks (Arduengo et al., 1991). 1,3-disubstituted imidazolium salts play important roles in synthesis of transition metal NHC's (Lin et al., 2009; Saito et al., 2011; Wang et al., 2005). Herein, we report on the crystal structure of the title compound, a new NHC precursor.

The molecular structure of the title compound is shown in Fig. 1. Bond lengths (Allen et al., 1987) and angles in the cation are normal. The mean plane of the naphthalene ring [A = (N1,N2,C23—C24)] makes dihedral angles with the mean planes of the imidazole rings [B = (N1,N2,C23—C25); C = (N3,N4,C8—C10)] and the benzene rings [D = (C27—C32); E = (C1—C6)] of A/B = 79.15 (15) °, A/C = 76.85 (16) °, A/D = 56.15 (19) °, and A/E = 80.56 (16)°. The PF₆^- anions are disordered with two postitions found for nine F atoms (F4—F6, F7—F12) in the equitorial planes.

In the crystal there are weak π···π interactions involving the imidazole, benzene and naphthalene rings with centroid-centroid distances, Cg1···Cg3ⁱ, Cg5···Cg5ⁱⁱ of 3.847 (2) and 3.5744 (19) Å, respectively [symmetry codes: (i) x, y + 1, z; (ii) -x, y, -z + 1/2. Cg1 centroid of the imidazole ring (N1,N2,C23—C24); Cg3 centroid of ring (C1—C6); Cg5 centroid of ring (C16—C21)]. In addition, a number of C—H···F hydrogen bonds are observed (Table 1 and Fig. 2).

Related literature top

For the first free carbenes isolated, see: Arduengo et al. (1991). For the application of N-heterocyclic carbene ligands in transmetalation, see: Lin et al. (2009); Saito et al. (2011); Wang et al. (2005). For the synthesis of the title compound, see: Saito et al. (2011). For related structures, see: Saito et al. (2011). For standard bond lengths, see: Allen et al. (1987).

Experimental top

The title compound was prepared according to the reported procedures (Saito et al., 2011). Colourless single crystals suitable for X-ray diffraction were obtained by recrystallization from acetonitrile and ethyl ether (v/v = 1:1).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 the title compound with atom numbering. The displacement ellipsoids are drawn at the 30% probability level. Only the major components of the disordered fluorine atoms are shown.
	Fig. 2. Crystal packing of the title compound viewed along the b axis, showing the C—H···F interactions (dashed lines) involving the cations and anions [H atoms not involved in these interactions have been omitted for clarity].

3-benzyl-1-({4-[(3-benzyl-1H-imidazol-3-ium-1-yl)methyl]naphthalen- 1-yl}methyl)-1H-imidazol-3-ium bis(hexafluorophosphate) top

Crystal data top

C₃₂H₃₀N₄²⁺·2PF₆⁻	F(000) = 3104
M_r = 760.54	D_x = 1.482 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9587 reflections
a = 33.8250 (9) Å	θ = 2.4–27.5°
b = 11.6062 (3) Å	µ = 0.22 mm⁻¹
c = 17.6986 (5) Å	T = 296 K
β = 101.158 (1)°	Block, colourless
V = 6816.8 (3) Å³	0.20 × 0.20 × 0.15 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	5990 independent reflections
Radiation source: fine-focus sealed tube	4848 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −40→39
T_min = 0.957, T_max = 0.967	k = 0→13
5990 measured reflections	l = 0→20

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.163	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0576P)² + 12.5479P] where P = (F_o² + 2F_c²)/3
5990 reflections	(Δ/σ)_max = 0.004
534 parameters	Δρ_max = 0.43 e Å⁻³
106 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₃₂H₃₀N₄²⁺·2PF₆⁻	V = 6816.8 (3) Å³
M_r = 760.54	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 33.8250 (9) Å	µ = 0.22 mm⁻¹
b = 11.6062 (3) Å	T = 296 K
c = 17.6986 (5) Å	0.20 × 0.20 × 0.15 mm
β = 101.158 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5990 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	4848 reflections with I > 2σ(I)
T_min = 0.957, T_max = 0.967	R_int = 0.029
5990 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	106 restraints
wR(F²) = 0.163	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0576P)² + 12.5479P] where P = (F_o² + 2F_c²)/3
5990 reflections	Δρ_max = 0.43 e Å⁻³
534 parameters	Δρ_min = −0.25 e Å⁻³

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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)
N1	0.08264 (7)	0.9657 (2)	0.37930 (14)	0.0574 (9)
N2	0.14129 (8)	0.9374 (2)	0.44984 (15)	0.0617 (9)
N3	0.11786 (8)	0.5263 (2)	0.15155 (14)	0.0592 (9)
N4	0.15515 (8)	0.3862 (2)	0.20370 (16)	0.0632 (10)
C1	0.15298 (16)	0.2279 (4)	0.4641 (3)	0.0944 (19)
C2	0.12019 (14)	0.2474 (4)	0.4077 (3)	0.0909 (17)
C3	0.12467 (12)	0.2595 (3)	0.3324 (2)	0.0790 (14)
C4	0.16251 (11)	0.2531 (3)	0.3133 (2)	0.0694 (11)
C5	0.19513 (12)	0.2329 (3)	0.3711 (3)	0.0883 (17)
C6	0.19023 (15)	0.2197 (4)	0.4466 (3)	0.1003 (17)
C7	0.16755 (12)	0.2689 (3)	0.2311 (2)	0.0781 (16)
C8	0.17466 (11)	0.4866 (3)	0.2285 (2)	0.0734 (14)
C9	0.15153 (10)	0.5735 (3)	0.1960 (2)	0.0684 (11)
C10	0.12119 (10)	0.4129 (3)	0.15704 (18)	0.0620 (11)
C11	0.08189 (11)	0.5901 (3)	0.11210 (18)	0.0682 (11)
C12	0.07110 (9)	0.6843 (3)	0.16312 (17)	0.0577 (10)
C13	0.07231 (10)	0.7958 (3)	0.14081 (18)	0.0644 (11)
C14	0.06459 (10)	0.8860 (3)	0.18869 (19)	0.0659 (12)
C15	0.05548 (9)	0.8652 (3)	0.25894 (18)	0.0578 (10)
C16	0.05272 (8)	0.7490 (3)	0.28405 (17)	0.0539 (10)
C17	0.06026 (9)	0.6572 (3)	0.23542 (17)	0.0555 (10)
C18	0.05654 (10)	0.5432 (3)	0.2607 (2)	0.0685 (12)
C19	0.04682 (11)	0.5197 (3)	0.3299 (2)	0.0804 (16)
C20	0.03969 (11)	0.6100 (4)	0.3780 (2)	0.0758 (14)
C21	0.04222 (9)	0.7207 (3)	0.35529 (19)	0.0647 (11)
C22	0.04995 (10)	0.9646 (3)	0.31026 (19)	0.0689 (11)
C23	0.12086 (9)	0.9425 (3)	0.37841 (18)	0.0597 (11)
C24	0.07865 (11)	0.9759 (3)	0.45441 (19)	0.0667 (12)
C25	0.11500 (11)	0.9584 (3)	0.49870 (19)	0.0686 (11)
C26	0.18335 (10)	0.8995 (4)	0.4714 (2)	0.0794 (14)
C27	0.18627 (11)	0.7727 (4)	0.48956 (19)	0.0740 (14)
C28	0.16502 (17)	0.6915 (4)	0.4413 (3)	0.126 (2)
C29	0.1689 (2)	0.5760 (5)	0.4574 (3)	0.145 (3)
C30	0.19425 (18)	0.5390 (5)	0.5218 (3)	0.118 (3)
C31	0.21537 (13)	0.6164 (5)	0.5702 (3)	0.100 (2)
C32	0.21155 (11)	0.7333 (4)	0.5550 (2)	0.0830 (16)
P2	0.01796 (3)	0.22512 (7)	0.09338 (5)	0.0606 (3)
F7	0.0471 (3)	0.2620 (10)	0.0432 (4)	0.150 (5)	0.545 (10)
F8	−0.0064 (5)	0.1822 (15)	0.1482 (8)	0.218 (7)	0.545 (10)
F9	0.0099 (3)	0.1149 (13)	0.0461 (12)	0.211 (7)	0.545 (10)
F10	0.0551 (4)	0.1765 (9)	0.1469 (9)	0.194 (6)	0.545 (10)
F11	0.0261 (2)	0.3391 (8)	0.1372 (8)	0.126 (4)	0.545 (10)
F12	−0.0194 (3)	0.2793 (10)	0.0455 (8)	0.176 (5)	0.545 (10)
F7'	0.0197 (5)	0.3549 (9)	0.0831 (11)	0.182 (7)	0.455 (10)
F8'	−0.0224 (3)	0.2198 (11)	0.1211 (10)	0.139 (6)	0.455 (10)
F9'	0.0171 (4)	0.0931 (7)	0.0937 (9)	0.145 (5)	0.455 (10)
F10'	0.0597 (3)	0.2222 (14)	0.0719 (12)	0.176 (7)	0.455 (10)
F11'	0.0399 (6)	0.246 (2)	0.1736 (5)	0.221 (9)	0.455 (10)
F12'	−0.0018 (5)	0.2177 (15)	0.0093 (5)	0.173 (6)	0.455 (10)
P1	0.19770 (3)	0.92074 (8)	0.20869 (5)	0.0678 (3)
F1	0.23389 (10)	0.8405 (3)	0.2363 (2)	0.1598 (16)
F2	0.16208 (12)	1.0041 (3)	0.1833 (3)	0.198 (2)
F3	0.17942 (15)	0.8392 (3)	0.14383 (19)	0.190 (2)
F4	0.17314 (15)	0.8443 (4)	0.2571 (3)	0.126 (2)	0.793 (11)
F5	0.2123 (2)	0.9987 (4)	0.2799 (3)	0.144 (3)	0.793 (11)
F6	0.2185 (3)	0.9949 (9)	0.1582 (5)	0.224 (5)	0.793 (11)
F4'	0.1816 (8)	0.937 (3)	0.2751 (11)	0.196 (13)	0.207 (11)
F5'	0.2303 (5)	1.015 (2)	0.230 (2)	0.178 (12)	0.207 (11)
F6'	0.2236 (9)	0.916 (2)	0.1454 (17)	0.178 (12)	0.207 (11)
H1	0.14990	0.22020	0.51500	0.1130*
H2	0.09470	0.25260	0.41990	0.1090*
H3	0.10210	0.27200	0.29400	0.0940*
H5	0.22080	0.22810	0.35960	0.1060*
H6	0.21250	0.20520	0.48530	0.1200*
H7A	0.19550	0.25660	0.22780	0.0940*
H7B	0.15130	0.21250	0.19850	0.0940*
H8	0.19940	0.49320	0.26180	0.0880*
H9	0.15730	0.65160	0.20250	0.0820*
H10	0.10240	0.36020	0.13180	0.0740*
H11A	0.05940	0.53740	0.09870	0.0820*
H11B	0.08720	0.62350	0.06480	0.0820*
H13	0.07840	0.81270	0.09300	0.0770*
H14	0.06570	0.96170	0.17200	0.0790*
H18	0.06090	0.48250	0.22900	0.0820*
H19	0.04490	0.44370	0.34540	0.0970*
H20	0.03320	0.59390	0.42560	0.0910*
H21	0.03690	0.77970	0.38740	0.0780*
H22A	0.05020	1.03630	0.28220	0.0830*
H22B	0.02410	0.95790	0.32590	0.0830*
H23	0.13160	0.93150	0.33440	0.0720*
H24	0.05500	0.99210	0.47170	0.0800*
H25	0.12130	0.96010	0.55220	0.0820*
H26A	0.19670	0.94270	0.51600	0.0960*
H26B	0.19720	0.91550	0.42940	0.0960*
H28	0.14770	0.71560	0.39670	0.1510*
H29	0.15400	0.52290	0.42410	0.1740*
H30	0.19710	0.46060	0.53240	0.1410*
H31	0.23270	0.59100	0.61440	0.1200*
H32	0.22620	0.78570	0.58930	0.0990*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0562 (15)	0.0533 (15)	0.0632 (15)	0.0026 (12)	0.0131 (12)	−0.0050 (12)
N2	0.0576 (15)	0.0639 (17)	0.0618 (15)	−0.0065 (13)	0.0073 (12)	−0.0049 (13)
N3	0.0649 (16)	0.0524 (16)	0.0626 (15)	−0.0048 (12)	0.0183 (13)	−0.0055 (12)
N4	0.0701 (17)	0.0515 (16)	0.0719 (17)	−0.0020 (13)	0.0232 (14)	−0.0047 (13)
C1	0.117 (4)	0.082 (3)	0.084 (3)	−0.017 (3)	0.019 (3)	0.009 (2)
C2	0.097 (3)	0.084 (3)	0.099 (3)	−0.006 (2)	0.037 (3)	0.015 (2)
C3	0.073 (2)	0.075 (2)	0.090 (3)	−0.0007 (19)	0.018 (2)	0.013 (2)
C4	0.079 (2)	0.0464 (18)	0.085 (2)	−0.0022 (16)	0.0215 (19)	0.0030 (16)
C5	0.074 (3)	0.079 (3)	0.111 (3)	−0.007 (2)	0.016 (2)	0.010 (2)
C6	0.095 (3)	0.100 (3)	0.096 (3)	−0.018 (3)	−0.006 (3)	0.016 (3)
C7	0.096 (3)	0.051 (2)	0.094 (3)	0.0088 (18)	0.035 (2)	0.0017 (18)
C8	0.061 (2)	0.060 (2)	0.098 (3)	−0.0064 (17)	0.0125 (18)	−0.0120 (19)
C9	0.063 (2)	0.0527 (19)	0.090 (2)	−0.0108 (16)	0.0163 (18)	−0.0066 (17)
C10	0.073 (2)	0.0528 (19)	0.0645 (19)	−0.0110 (16)	0.0239 (17)	−0.0107 (15)
C11	0.080 (2)	0.067 (2)	0.0560 (18)	0.0009 (17)	0.0092 (16)	−0.0028 (16)
C12	0.0560 (18)	0.0601 (19)	0.0536 (17)	0.0000 (14)	0.0023 (13)	0.0000 (14)
C13	0.069 (2)	0.068 (2)	0.0545 (17)	0.0042 (16)	0.0075 (15)	0.0092 (15)
C14	0.070 (2)	0.055 (2)	0.068 (2)	0.0103 (16)	0.0018 (16)	0.0089 (16)
C15	0.0480 (16)	0.0588 (19)	0.0619 (18)	0.0072 (14)	−0.0010 (13)	−0.0019 (15)
C16	0.0405 (15)	0.0602 (18)	0.0576 (17)	0.0005 (13)	0.0014 (12)	−0.0029 (14)
C17	0.0492 (16)	0.0578 (19)	0.0571 (17)	−0.0045 (14)	0.0044 (13)	−0.0016 (14)
C18	0.073 (2)	0.058 (2)	0.077 (2)	−0.0109 (16)	0.0205 (17)	−0.0041 (17)
C19	0.087 (3)	0.067 (2)	0.093 (3)	−0.014 (2)	0.032 (2)	0.010 (2)
C20	0.077 (2)	0.085 (3)	0.070 (2)	−0.013 (2)	0.0255 (18)	0.002 (2)
C21	0.0586 (19)	0.073 (2)	0.0627 (19)	−0.0069 (16)	0.0122 (15)	−0.0082 (16)
C22	0.0598 (19)	0.065 (2)	0.077 (2)	0.0142 (16)	0.0009 (16)	−0.0039 (17)
C23	0.0579 (18)	0.062 (2)	0.0599 (18)	0.0012 (15)	0.0132 (15)	−0.0041 (15)
C24	0.069 (2)	0.063 (2)	0.073 (2)	−0.0040 (17)	0.0257 (18)	−0.0052 (17)
C25	0.083 (2)	0.069 (2)	0.0571 (18)	−0.0074 (18)	0.0215 (17)	−0.0061 (16)
C26	0.057 (2)	0.095 (3)	0.079 (2)	−0.0070 (19)	−0.0048 (17)	−0.007 (2)
C27	0.066 (2)	0.089 (3)	0.062 (2)	0.0104 (19)	−0.0002 (16)	−0.0031 (18)
C28	0.158 (5)	0.086 (3)	0.104 (3)	0.012 (3)	−0.050 (3)	−0.008 (3)
C29	0.189 (6)	0.084 (4)	0.132 (5)	0.017 (4)	−0.040 (4)	−0.013 (3)
C30	0.142 (5)	0.099 (4)	0.112 (4)	0.037 (3)	0.023 (3)	0.011 (3)
C31	0.082 (3)	0.143 (5)	0.076 (3)	0.041 (3)	0.019 (2)	0.027 (3)
C32	0.062 (2)	0.126 (4)	0.061 (2)	0.012 (2)	0.0122 (17)	−0.002 (2)
P2	0.0639 (5)	0.0547 (5)	0.0654 (5)	−0.0080 (4)	0.0180 (4)	−0.0066 (4)
F7	0.154 (9)	0.226 (11)	0.091 (4)	−0.023 (7)	0.079 (5)	0.025 (5)
F8	0.262 (15)	0.250 (14)	0.184 (9)	−0.128 (11)	0.148 (11)	0.007 (9)
F9	0.140 (8)	0.190 (11)	0.327 (15)	−0.072 (8)	0.104 (10)	−0.211 (11)
F10	0.179 (9)	0.119 (7)	0.234 (13)	0.039 (6)	−0.083 (9)	0.055 (7)
F11	0.098 (5)	0.096 (6)	0.199 (10)	−0.032 (4)	0.067 (6)	−0.091 (7)
F12	0.108 (5)	0.225 (10)	0.163 (9)	0.055 (6)	−0.052 (6)	−0.001 (8)
F7'	0.224 (13)	0.058 (5)	0.272 (16)	−0.011 (5)	0.066 (13)	0.018 (8)
F8'	0.068 (4)	0.125 (7)	0.241 (17)	−0.014 (4)	0.074 (6)	−0.067 (9)
F9'	0.141 (7)	0.052 (4)	0.234 (14)	0.006 (4)	0.016 (8)	0.056 (7)
F10'	0.067 (5)	0.176 (10)	0.302 (17)	−0.047 (6)	0.077 (8)	−0.168 (11)
F11'	0.270 (18)	0.32 (2)	0.057 (4)	−0.155 (15)	−0.011 (6)	−0.022 (8)
F12'	0.241 (14)	0.191 (12)	0.062 (4)	−0.058 (10)	−0.034 (5)	0.015 (5)
P1	0.0671 (6)	0.0703 (6)	0.0606 (5)	−0.0036 (4)	−0.0012 (4)	0.0045 (4)
F1	0.118 (2)	0.166 (3)	0.189 (3)	0.069 (2)	0.014 (2)	0.005 (3)
F2	0.156 (3)	0.117 (3)	0.268 (5)	0.044 (2)	−0.091 (3)	0.005 (3)
F3	0.270 (5)	0.171 (4)	0.106 (2)	−0.068 (3)	−0.018 (3)	−0.047 (2)
F4	0.164 (4)	0.092 (3)	0.146 (4)	−0.013 (3)	0.092 (3)	0.009 (2)
F5	0.181 (6)	0.097 (3)	0.124 (4)	0.006 (3)	−0.046 (4)	−0.043 (3)
F6	0.271 (10)	0.221 (9)	0.187 (7)	−0.097 (8)	0.065 (6)	0.100 (7)
F4'	0.21 (2)	0.30 (3)	0.119 (12)	−0.03 (2)	0.136 (14)	−0.061 (18)
F5'	0.055 (8)	0.21 (2)	0.26 (3)	−0.054 (10)	0.007 (13)	0.01 (2)
F6'	0.21 (2)	0.14 (2)	0.23 (2)	0.038 (19)	0.160 (19)	−0.010 (19)

Geometric parameters (Å, º) top

P2—F8'	1.539 (12)	C15—C22	1.502 (5)
P2—F9'	1.533 (8)	C15—C16	1.429 (5)
P2—F10'	1.532 (12)	C16—C17	1.423 (5)
P2—F11'	1.489 (11)	C16—C21	1.413 (4)
P2—F12'	1.511 (9)	C17—C18	1.410 (5)
P2—F11	1.531 (11)	C18—C19	1.356 (5)
P2—F12	1.515 (12)	C19—C20	1.400 (5)
P2—F7'	1.520 (11)	C20—C21	1.354 (6)
P2—F7	1.511 (9)	C24—C25	1.340 (5)
P2—F8	1.476 (16)	C26—C27	1.506 (6)
P2—F9	1.524 (17)	C27—C28	1.377 (6)
P2—F10	1.528 (14)	C27—C32	1.378 (5)
P1—F1	1.541 (4)	C28—C29	1.372 (7)
P1—F2	1.543 (4)	C29—C30	1.357 (8)
P1—F3	1.524 (4)	C30—C31	1.347 (8)
P1—F6	1.509 (10)	C31—C32	1.384 (7)
P1—F4	1.577 (5)	C1—H1	0.9300
P1—F5	1.552 (5)	C2—H2	0.9300
P1—F6'	1.55 (3)	C3—H3	0.9300
P1—F4'	1.40 (2)	C5—H5	0.9300
P1—F5'	1.55 (2)	C6—H6	0.9300
N1—C22	1.481 (4)	C7—H7B	0.9700
N1—C23	1.324 (4)	C7—H7A	0.9700
N1—C24	1.367 (4)	C8—H8	0.9300
N2—C23	1.320 (4)	C9—H9	0.9300
N2—C25	1.377 (4)	C10—H10	0.9300
N2—C26	1.467 (4)	C11—H11B	0.9700
N3—C10	1.323 (4)	C11—H11A	0.9700
N3—C9	1.367 (4)	C13—H13	0.9300
N3—C11	1.479 (4)	C14—H14	0.9300
N4—C10	1.315 (4)	C18—H18	0.9300
N4—C7	1.478 (4)	C19—H19	0.9300
N4—C8	1.369 (4)	C20—H20	0.9300
C1—C6	1.358 (8)	C21—H21	0.9300
C1—C2	1.360 (7)	C22—H22A	0.9700
C2—C3	1.377 (6)	C22—H22B	0.9700
C3—C4	1.388 (6)	C23—H23	0.9300
C4—C5	1.372 (6)	C24—H24	0.9300
C4—C7	1.508 (5)	C25—H25	0.9300
C5—C6	1.386 (7)	C26—H26A	0.9700
C8—C9	1.336 (5)	C26—H26B	0.9700
C11—C12	1.507 (5)	C28—H28	0.9300
C12—C13	1.356 (5)	C29—H29	0.9300
C12—C17	1.433 (4)	C30—H30	0.9300
C13—C14	1.403 (5)	C31—H31	0.9300
C14—C15	1.359 (5)	C32—H32	0.9300

F8—P2—F11	91.6 (8)	C14—C15—C22	119.6 (3)
F8—P2—F12	89.8 (8)	C15—C16—C21	122.7 (3)
F9—P2—F10	93.9 (7)	C17—C16—C21	118.1 (3)
F9—P2—F11	177.2 (9)	C15—C16—C17	119.2 (3)
F9—P2—F12	90.0 (7)	C12—C17—C18	122.9 (3)
F10—P2—F11	87.7 (6)	C16—C17—C18	118.2 (3)
F10—P2—F12	175.5 (7)	C12—C17—C16	118.9 (3)
F11—P2—F12	88.5 (6)	C17—C18—C19	121.8 (3)
F7'—P2—F8'	97.8 (8)	C18—C19—C20	119.9 (3)
F7'—P2—F9'	173.0 (9)	C19—C20—C21	120.1 (3)
F7'—P2—F10'	86.2 (9)	C16—C21—C20	121.8 (3)
F7'—P2—F11'	85.9 (11)	N1—C22—C15	110.2 (3)
F7'—P2—F12'	87.6 (10)	N1—C23—N2	109.2 (3)
F8'—P2—F9'	86.6 (7)	N1—C24—C25	107.7 (3)
F8'—P2—F10'	174.5 (9)	N2—C25—C24	106.9 (3)
F8'—P2—F11'	90.7 (10)	N2—C26—C27	111.6 (3)
F8'—P2—F12'	93.5 (9)	C26—C27—C28	122.1 (3)
F9'—P2—F10'	89.9 (8)	C26—C27—C32	120.6 (4)
F9'—P2—F11'	99.5 (11)	C28—C27—C32	117.3 (4)
F9'—P2—F12'	86.7 (9)	C27—C28—C29	121.5 (5)
F10'—P2—F11'	85.8 (11)	C28—C29—C30	120.2 (5)
F10'—P2—F12'	90.4 (10)	C29—C30—C31	119.6 (5)
F11'—P2—F12'	172.8 (11)	C30—C31—C32	120.8 (5)
F7—P2—F12	97.0 (6)	C27—C32—C31	120.5 (4)
F8—P2—F9	90.8 (9)	C2—C1—H1	120.00
F8—P2—F10	88.0 (8)	C6—C1—H1	120.00
F7—P2—F8	173.2 (7)	C3—C2—H2	120.00
F7—P2—F9	89.0 (7)	C1—C2—H2	120.00
F7—P2—F10	85.3 (6)	C2—C3—H3	120.00
F7—P2—F11	88.8 (6)	C4—C3—H3	120.00
F1—P1—F2	178.0 (2)	C4—C5—H5	120.00
F1—P1—F3	92.6 (2)	C6—C5—H5	120.00
F1—P1—F4	87.6 (2)	C5—C6—H6	120.00
F2—P1—F5	88.8 (3)	C1—C6—H6	120.00
F2—P1—F6	84.1 (4)	N4—C7—H7B	110.00
F2—P1—F4'	75.6 (12)	C4—C7—H7A	110.00
F2—P1—F5'	96.2 (8)	H7A—C7—H7B	108.00
F2—P1—F6'	109.3 (10)	C4—C7—H7B	110.00
F3—P1—F4	83.1 (2)	N4—C7—H7A	110.00
F3—P1—F5	173.1 (3)	N4—C8—H8	126.00
F3—P1—F6	94.4 (4)	C9—C8—H8	126.00
F3—P1—F4'	123.3 (12)	C8—C9—H9	126.00
F3—P1—F5'	142.1 (12)	N3—C9—H9	126.00
F3—P1—F6'	68.7 (10)	N3—C10—H10	125.00
F4—P1—F5	90.3 (3)	N4—C10—H10	125.00
F4—P1—F6	176.0 (4)	N3—C11—H11A	110.00
F5—P1—F6	92.1 (4)	N3—C11—H11B	110.00
F4'—P1—F5'	94.3 (17)	H11A—C11—H11B	108.00
F4'—P1—F6'	167.6 (16)	C12—C11—H11B	110.00
F5'—P1—F6'	74.1 (15)	C12—C11—H11A	110.00
F1—P1—F5	89.2 (3)	C12—C13—H13	119.00
F1—P1—F6	95.7 (4)	C14—C13—H13	119.00
F1—P1—F4'	103.3 (12)	C13—C14—H14	119.00
F1—P1—F5'	82.2 (8)	C15—C14—H14	119.00
F1—P1—F6'	71.5 (10)	C17—C18—H18	119.00
F2—P1—F3	89.4 (2)	C19—C18—H18	119.00
F2—P1—F4	92.7 (2)	C20—C19—H19	120.00
C22—N1—C24	127.2 (3)	C18—C19—H19	120.00
C23—N1—C24	108.0 (3)	C19—C20—H20	120.00
C22—N1—C23	124.3 (3)	C21—C20—H20	120.00
C23—N2—C25	108.2 (3)	C20—C21—H21	119.00
C23—N2—C26	124.4 (3)	C16—C21—H21	119.00
C25—N2—C26	127.0 (3)	N1—C22—H22A	110.00
C9—N3—C10	107.9 (3)	C15—C22—H22B	110.00
C9—N3—C11	126.1 (3)	H22A—C22—H22B	108.00
C10—N3—C11	125.7 (3)	N1—C22—H22B	110.00
C7—N4—C8	126.2 (3)	C15—C22—H22A	110.00
C7—N4—C10	125.5 (3)	N1—C23—H23	125.00
C8—N4—C10	108.0 (3)	N2—C23—H23	125.00
C2—C1—C6	120.4 (5)	C25—C24—H24	126.00
C1—C2—C3	120.0 (5)	N1—C24—H24	126.00
C2—C3—C4	120.6 (4)	C24—C25—H25	127.00
C5—C4—C7	121.0 (4)	N2—C25—H25	127.00
C3—C4—C7	120.7 (3)	N2—C26—H26A	109.00
C3—C4—C5	118.3 (3)	N2—C26—H26B	109.00
C4—C5—C6	120.6 (4)	C27—C26—H26B	109.00
C1—C6—C5	120.1 (5)	H26A—C26—H26B	108.00
N4—C7—C4	110.5 (3)	C27—C26—H26A	109.00
N4—C8—C9	107.4 (3)	C29—C28—H28	119.00
N3—C9—C8	107.4 (3)	C27—C28—H28	119.00
N3—C10—N4	109.4 (3)	C28—C29—H29	120.00
N3—C11—C12	110.7 (3)	C30—C29—H29	120.00
C11—C12—C13	119.6 (3)	C29—C30—H30	120.00
C11—C12—C17	120.6 (3)	C31—C30—H30	120.00
C13—C12—C17	119.8 (3)	C32—C31—H31	120.00
C12—C13—C14	121.1 (3)	C30—C31—H31	120.00
C13—C14—C15	121.5 (3)	C27—C32—H32	120.00
C14—C15—C16	119.5 (3)	C31—C32—H32	120.00
C16—C15—C22	120.9 (3)

C23—N1—C22—C15	40.0 (4)	C11—C12—C13—C14	−176.5 (3)
C24—N1—C22—C15	−131.3 (3)	C17—C12—C13—C14	2.4 (5)
C22—N1—C23—N2	−172.6 (3)	C11—C12—C17—C16	176.1 (3)
C24—N1—C23—N2	0.1 (4)	C11—C12—C17—C18	−4.1 (5)
C22—N1—C24—C25	172.4 (3)	C13—C12—C17—C16	−2.8 (5)
C23—N1—C24—C25	−0.1 (4)	C13—C12—C17—C18	176.9 (3)
C25—N2—C23—N1	−0.1 (4)	C12—C13—C14—C15	−0.3 (5)
C26—N2—C23—N1	172.1 (3)	C13—C14—C15—C16	−1.5 (5)
C23—N2—C25—C24	0.0 (4)	C13—C14—C15—C22	176.3 (3)
C26—N2—C25—C24	−171.9 (3)	C14—C15—C16—C17	1.1 (4)
C23—N2—C26—C27	−93.1 (4)	C14—C15—C16—C21	−178.1 (3)
C25—N2—C26—C27	77.6 (4)	C22—C15—C16—C17	−176.7 (3)
C10—N3—C9—C8	−0.6 (4)	C22—C15—C16—C21	4.2 (5)
C11—N3—C9—C8	172.5 (3)	C14—C15—C22—N1	−112.9 (3)
C9—N3—C10—N4	0.8 (4)	C16—C15—C22—N1	64.8 (4)
C11—N3—C10—N4	−172.3 (3)	C15—C16—C17—C12	1.1 (4)
C9—N3—C11—C12	−40.9 (4)	C15—C16—C17—C18	−178.7 (3)
C10—N3—C11—C12	131.0 (3)	C21—C16—C17—C12	−179.8 (3)
C8—N4—C7—C4	68.7 (4)	C21—C16—C17—C18	0.5 (4)
C10—N4—C7—C4	−103.9 (4)	C15—C16—C21—C20	179.9 (3)
C7—N4—C8—C9	−173.3 (3)	C17—C16—C21—C20	0.7 (5)
C10—N4—C8—C9	0.3 (4)	C12—C17—C18—C19	179.0 (3)
C7—N4—C10—N3	172.9 (3)	C16—C17—C18—C19	−1.2 (5)
C8—N4—C10—N3	−0.7 (4)	C17—C18—C19—C20	0.8 (5)
C6—C1—C2—C3	−0.3 (7)	C18—C19—C20—C21	0.5 (6)
C2—C1—C6—C5	1.0 (7)	C19—C20—C21—C16	−1.2 (5)
C1—C2—C3—C4	−0.6 (6)	N1—C24—C25—N2	0.0 (4)
C2—C3—C4—C5	0.9 (5)	N2—C26—C27—C28	49.1 (5)
C2—C3—C4—C7	−178.7 (4)	N2—C26—C27—C32	−132.8 (3)
C3—C4—C5—C6	−0.2 (5)	C26—C27—C28—C29	178.0 (5)
C7—C4—C5—C6	179.3 (4)	C32—C27—C28—C29	−0.2 (7)
C3—C4—C7—N4	63.1 (4)	C26—C27—C32—C31	−177.6 (4)
C5—C4—C7—N4	−116.5 (4)	C28—C27—C32—C31	0.7 (6)
C4—C5—C6—C1	−0.7 (6)	C27—C28—C29—C30	−0.4 (9)
N4—C8—C9—N3	0.2 (4)	C28—C29—C30—C31	0.5 (9)
N3—C11—C12—C13	117.3 (3)	C29—C30—C31—C32	−0.1 (8)
N3—C11—C12—C17	−61.7 (4)	C30—C31—C32—C27	−0.6 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···F3ⁱ	0.93	2.41	3.229 (6)	147
C7—H7A···F1ⁱⁱ	0.97	2.54	3.375 (5)	144
C7—H7B···F2ⁱⁱⁱ	0.97	2.47	3.184 (5)	130
C9—H9···F4	0.93	2.45	3.358 (6)	164
C10—H10···F7	0.93	2.47	3.384 (10)	166
C14—H14···F10^iv	0.93	2.55	3.453 (11)	165
C18—H18···F11	0.93	2.46	3.252 (12)	143
C18—H18···N3	0.93	2.62	3.102 (4)	113
C23—H23···F4	0.93	2.37	3.241 (6)	156
C24—H24···F9ⁱ	0.93	2.53	3.258 (15)	136
C25—H25···F2^v	0.93	2.49	3.374 (6)	158

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

Experimental details

Crystal data
Chemical formula	C₃₂H₃₀N₄²⁺·2PF₆⁻
M_r	760.54
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	33.8250 (9), 11.6062 (3), 17.6986 (5)
β (°)	101.158 (1)
V (Å³)	6816.8 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.20 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.957, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	5990, 5990, 4848
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.163, 1.04
No. of reflections	5990
No. of parameters	534
No. of restraints	106
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0576P)² + 12.5479P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.25

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), 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
C1—H1···F3ⁱ	0.93	2.41	3.229 (6)	147
C7—H7A···F1ⁱⁱ	0.97	2.54	3.375 (5)	144
C7—H7B···F2ⁱⁱⁱ	0.97	2.47	3.184 (5)	130
C9—H9···F4	0.93	2.45	3.358 (6)	164
C10—H10···F7	0.93	2.47	3.384 (10)	166
C14—H14···F10^iv	0.93	2.55	3.453 (11)	165
C18—H18···F11	0.93	2.46	3.252 (12)	143
C18—H18···N3	0.93	2.62	3.102 (4)	113
C23—H23···F4	0.93	2.37	3.241 (6)	156
C24—H24···F9ⁱ	0.93	2.53	3.258 (15)	136
C25—H25···F2^v	0.93	2.49	3.374 (6)	158

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

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. Google Scholar
Arduengo, A. J., Harlow, R. L. & Kline, M. (1991). J. Am. Chem. Soc. 113, 361—363. Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lin, J. C. Y., Huang, R. T. W., Lee, C. S., Bhattacharyya, A., Hwang, W. S. & Lin, I. J. B. (2009). Chem. Rev. 109, 3561—3598. Google Scholar
Saito, S., Saika, M., Yamasaki, R., Azumaya, I. & Masu, H. (2011). Organometallics, 30, 1366–1373. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, J. W., Xu, F. B., Li, Q. S., Song, H. B. & Zhang, Z. Z. (2005). Inorg. Chem. Commun. 8, 1053–1055. Google Scholar

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Volume 67| Part 9| September 2011| Page o2343

doi:10.1107/S1600536811032132

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

3,3′-Di­benzyl-1,1′-[naphthalene-1,4-diylbis(methyl­ene)]di(1H-imidazol-3-ium) bis­­(hexa­fluoro­phosphate)

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Experimental

Crystal data

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organic compounds

3,3′-Dibenzyl-1,1′-[naphthalene-1,4-diylbis(methylene)]di(1H-imidazol-3-ium) bis(hexafluorophosphate)