1-{2-[2-(1H-Benzimidazol-1-yl)eth­oxy]eth­yl}-1H-benzimidazol-3-ium hexa­fluoro­phosphate

Sun, S.-F.; Xu, J.; Qin, D.-B.

doi:10.1107/S1600536810014534

organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page o1171

https://doi.org/10.1107/S1600536810014534

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1-{2-[2-(1H-Benzimidazol-1-yl)ethoxy]ethyl}-1H-benzimidazol-3-ium hexafluorophosphate

Sheng-Fu Sun,^a Jin Xu ^a and Da-Bin Qin ^a ^*

^aSchool of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
^*Correspondence e-mail: qindabincwnu@yahoo.com.cn

(Received 31 March 2010; accepted 20 April 2010; online 24 April 2010)

In the title salt, C₁₈H₁₉N₄O⁺·PF₆⁻, the dihedral angle between the benzimidazolium and benzimidazole ring systems is 16.24 (2)°. In the cation, a π–π interaction is observed between the imidazolium ring and the benzene ring of the benzimidazole ring system [centroid–centroid distance = 3.5713 (11) Å]. The PF₆⁻ ion is disordered over two sites, with occupancies of 0.895 (2) and 0.105 (2). In the crystal structure, pairs of N—H⋯N hydrogen bonds link the cations, forming centrosymmetric dimers. The dimers are linked via π–π interactions [centroid–centroid distance = 3.5606 (11) Å]. In addition, C—H⋯F hydrogen bonds are observed.

Related literature

For the synthesis, see: Zeng et al. (2008 ). For general background to benzimidazole derivatives, see: Pal et al. (2007 ); Murru et al. (2009 ).

Experimental

Crystal data

C₁₈H₁₉N₄O⁺·PF₆⁻
M_r = 452.34
Monoclinic, P 2₁ /c
a = 10.5347 (18) Å
b = 13.771 (2) Å
c = 13.353 (2) Å
β = 92.507 (2)°
V = 1935.3 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 93 K
0.37 × 0.33 × 0.27 mm

Data collection

Rigaku SPIDER diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.923, T_max = 0.943
11885 measured reflections
3959 independent reflections
3445 reflections with I > 2σ(I)
R_int = 0.026
Standard reflections: 0

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.080
S = 1.00
3959 reflections
303 parameters
21 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N4ⁱ	1.05 (2)	1.68 (2)	2.724 (2)	176 (2)
C4—H4⋯F3ⁱⁱ	0.95	2.41	3.130 (2)	133
C7—H7⋯F4ⁱⁱⁱ	0.95	2.23	3.100 (2)	152
C9—H9B⋯F2ⁱⁱⁱ	0.99	2.40	3.340 (2)	159
C11—H11A⋯F2^iv	0.99	2.51	3.066 (2)	116
C16—H16⋯F4^v	0.95	2.39	3.300 (2)	161
C18—H18⋯F6	0.95	2.38	3.298 (2)	163
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x, -y+1, -z+1; (iv) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (v) x+1, y, z.

Data collection: RAPID-AUTO (Rigaku/MSC, 2004 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810014534/ci5075sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810014534/ci5075Isup2.hkl

checkCIF report

Comment top

Benzimidazole derivatives are an important class of heterocycles that are present in a number of biologically active compounds. These derivatives are also used as cyclic N-heterocyclic carbene (NHC) precursors (Murru et al., 2009). A benzimidazole N-donor dinuclear palladacycle complex is used as an efficient Suzuki coupling catalyst (Pal et al., 2007).

Bond lengths and angles in the ionic pairs (Fig. 1) are within normal ranges. The benzimidazolium and benzimidazole ring systems make a dihedral angle of 16.24 (2)°. In the cation, a π–π interaction is observed between N1/C1/C6/N2C7 and C12-C17 rings, with the ring centroids being separated by 3.5713 (11) Å.

In the crystal structure, pairs of N—H···N hydrogen bonds link cations to form centrosymmetric dimers. The dimers are linked via π–π interactions between the N1/C1/C6/N2C7 ring at (x, y, z) and the C12-C17 ring at (1-x, y-1/2, 1/2-z), with their centroids separated by 3.5606 (11) Å. In addition, C—H···F hydrogen bonds are observed (Table 1).

Related literature top

For the synthesis, see: Zeng et al. (2008). For general background to benzimidazole derivatives, see: Pal et al. (2007); Murru et al. (2009).

Experimental top

The title compound was prepared according to the reported procedure of Zeng et al.. (2008). Colourless single crystals suitable for X-ray diffraction were obtained by recrystallization from acetonitrile and ethyl ether.

Structure description top

For the synthesis, see: Zeng et al. (2008). For general background to benzimidazole derivatives, see: Pal et al. (2007); Murru et al. (2009).

Computing details top

Data collection: RAPID-AUTO (Rigaku/MSC, 2004); cell refinement: RAPID-AUTO (Rigaku/MSC, 2004); data reduction: RAPID-AUTO (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 30% probability level. C-bound H atoms have been omitted. For clarity, only the major disorder component is shown.

1-{2-[2-(1H-Benzimidazol-1-yl)ethoxy]ethyl}-1H- benzimidazol-3-ium hexafluorophosphate top

Crystal data top

C₁₈H₁₉N₄O⁺·PF₆⁻	F(000) = 928
M_r = 452.34	D_x = 1.553 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5714 reflections
a = 10.5347 (18) Å	θ = 3.1–27.5°
b = 13.771 (2) Å	µ = 0.22 mm⁻¹
c = 13.353 (2) Å	T = 93 K
β = 92.507 (2)°	Block, colourless
V = 1935.3 (6) Å³	0.37 × 0.33 × 0.27 mm
Z = 4

Data collection top

Rigaku SPIDER diffractometer	3959 independent reflections
Radiation source: Rotating Anode	3445 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 26.4°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −13→10
T_min = 0.923, T_max = 0.943	k = −13→17
11885 measured reflections	l = −15→16

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0259P)² + 0.968P] where P = (F_o² + 2F_c²)/3
3959 reflections	(Δ/σ)_max = 0.001
303 parameters	Δρ_max = 0.34 e Å⁻³
21 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₈H₁₉N₄O⁺·PF₆⁻	V = 1935.3 (6) Å³
M_r = 452.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.5347 (18) Å	µ = 0.22 mm⁻¹
b = 13.771 (2) Å	T = 93 K
c = 13.353 (2) Å	0.37 × 0.33 × 0.27 mm
β = 92.507 (2)°

Data collection top

Rigaku SPIDER diffractometer	3959 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3445 reflections with I > 2σ(I)
T_min = 0.923, T_max = 0.943	R_int = 0.026
11885 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	21 restraints
wR(F²) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.34 e Å⁻³
3959 reflections	Δρ_min = −0.28 e Å⁻³
303 parameters

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 > 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)
O1	0.20360 (11)	0.51931 (8)	0.18156 (8)	0.0247 (3)
N1	0.53426 (13)	0.40531 (10)	0.31178 (10)	0.0243 (3)
N2	0.41920 (13)	0.39824 (9)	0.17089 (10)	0.0218 (3)
N3	0.26475 (13)	0.62988 (10)	0.35541 (10)	0.0253 (3)
N4	0.39492 (14)	0.60700 (10)	0.48994 (10)	0.0294 (3)
C1	0.61864 (16)	0.39760 (11)	0.23507 (12)	0.0229 (3)
C2	0.75022 (16)	0.39314 (12)	0.23627 (13)	0.0285 (4)
H2	0.8005	0.3964	0.2970	0.034*
C3	0.80419 (17)	0.38372 (13)	0.14435 (14)	0.0319 (4)
H3	0.8941	0.3801	0.1420	0.038*
C4	0.73059 (17)	0.37927 (13)	0.05438 (13)	0.0311 (4)
H4	0.7718	0.3730	−0.0072	0.037*
C5	0.60018 (16)	0.38377 (12)	0.05330 (12)	0.0262 (4)
H5	0.5499	0.3808	−0.0075	0.031*
C6	0.54567 (15)	0.39293 (11)	0.14572 (12)	0.0218 (3)
C7	0.41753 (16)	0.40521 (11)	0.27069 (12)	0.0245 (4)
H7	0.3424	0.4095	0.3073	0.029*
C8	0.31129 (15)	0.39532 (12)	0.09736 (12)	0.0242 (4)
H8A	0.3030	0.3288	0.0698	0.029*
H8B	0.3286	0.4397	0.0412	0.029*
C9	0.18818 (16)	0.42403 (12)	0.14171 (13)	0.0262 (4)
H9A	0.1185	0.4231	0.0895	0.031*
H9B	0.1668	0.3780	0.1954	0.031*
C10	0.10406 (16)	0.54786 (12)	0.24439 (12)	0.0272 (4)
H10A	0.0890	0.4968	0.2947	0.033*
H10B	0.0243	0.5584	0.2039	0.033*
C11	0.14574 (16)	0.64079 (13)	0.29557 (12)	0.0277 (4)
H11A	0.1568	0.6916	0.2442	0.033*
H11B	0.0783	0.6627	0.3397	0.033*
C12	0.38716 (16)	0.64002 (11)	0.32253 (12)	0.0231 (3)
C13	0.43309 (16)	0.65920 (12)	0.22830 (12)	0.0262 (4)
H13	0.3775	0.6687	0.1712	0.031*
C14	0.56322 (17)	0.66369 (12)	0.22204 (13)	0.0295 (4)
H14	0.5982	0.6764	0.1590	0.035*
C15	0.64530 (18)	0.64993 (12)	0.30653 (14)	0.0314 (4)
H15	0.7345	0.6539	0.2994	0.038*
C16	0.59940 (17)	0.63079 (12)	0.39979 (13)	0.0294 (4)
H16	0.6553	0.6214	0.4567	0.035*
C17	0.46803 (17)	0.62576 (11)	0.40726 (12)	0.0249 (4)
C18	0.27606 (18)	0.61067 (13)	0.45479 (12)	0.0299 (4)
H18	0.2053	0.6008	0.4953	0.036*
P1	−0.07196 (5)	0.71567 (4)	0.57610 (4)	0.02117 (17)	0.8952 (16)
F1	−0.10379 (15)	0.71525 (12)	0.45828 (8)	0.0350 (3)	0.8952 (16)
F2	−0.03912 (12)	0.71374 (11)	0.69440 (8)	0.0393 (4)	0.8952 (16)
F3	0.05729 (13)	0.77151 (12)	0.55925 (10)	0.0540 (4)	0.8952 (16)
F4	−0.19885 (12)	0.65494 (12)	0.59425 (9)	0.0479 (4)	0.8952 (16)
F5	−0.14535 (18)	0.81437 (11)	0.58739 (10)	0.0589 (5)	0.8952 (16)
F6	0.00255 (14)	0.61439 (10)	0.56578 (10)	0.0509 (4)	0.8952 (16)
P1'	−0.0834 (6)	0.7250 (5)	0.5725 (5)	0.141 (8)	0.1048 (16)
F1'	−0.0918 (11)	0.7157 (9)	0.4533 (4)	0.0350 (3)	0.1048 (16)
F2'	−0.0730 (10)	0.7334 (8)	0.6921 (5)	0.0393 (4)	0.1048 (16)
F3'	−0.0180 (10)	0.8283 (6)	0.5636 (8)	0.0540 (4)	0.1048 (16)
F4'	−0.1434 (9)	0.6186 (6)	0.5824 (8)	0.0479 (4)	0.1048 (16)
F5'	−0.2196 (8)	0.7721 (8)	0.5714 (8)	0.0589 (5)	0.1048 (16)
F6'	0.0549 (7)	0.6755 (8)	0.5745 (8)	0.0509 (4)	0.1048 (16)
H1N	0.560 (2)	0.4037 (15)	0.3887 (16)	0.052 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0252 (6)	0.0252 (6)	0.0238 (6)	−0.0009 (5)	0.0013 (5)	−0.0021 (5)
N1	0.0294 (8)	0.0246 (7)	0.0183 (7)	0.0024 (6)	−0.0043 (6)	−0.0007 (6)
N2	0.0255 (7)	0.0219 (7)	0.0177 (6)	0.0001 (6)	−0.0024 (5)	−0.0005 (5)
N3	0.0272 (8)	0.0310 (8)	0.0175 (7)	0.0061 (6)	−0.0033 (6)	−0.0007 (6)
N4	0.0360 (9)	0.0325 (8)	0.0192 (7)	0.0027 (6)	−0.0050 (6)	0.0010 (6)
C1	0.0294 (9)	0.0190 (8)	0.0200 (8)	0.0016 (6)	−0.0023 (7)	−0.0006 (6)
C2	0.0285 (9)	0.0297 (9)	0.0266 (9)	0.0011 (7)	−0.0083 (7)	0.0012 (7)
C3	0.0248 (9)	0.0350 (10)	0.0357 (10)	0.0030 (7)	0.0004 (8)	0.0041 (8)
C4	0.0323 (10)	0.0361 (10)	0.0252 (9)	0.0054 (8)	0.0048 (8)	0.0035 (8)
C5	0.0319 (10)	0.0281 (9)	0.0184 (8)	0.0021 (7)	−0.0026 (7)	0.0003 (7)
C6	0.0246 (9)	0.0180 (8)	0.0225 (8)	0.0011 (6)	−0.0026 (7)	−0.0001 (6)
C7	0.0301 (9)	0.0235 (8)	0.0198 (8)	0.0017 (7)	0.0007 (7)	−0.0002 (7)
C8	0.0261 (9)	0.0254 (9)	0.0204 (8)	−0.0013 (7)	−0.0059 (7)	−0.0011 (7)
C9	0.0259 (9)	0.0268 (9)	0.0255 (9)	−0.0024 (7)	−0.0030 (7)	−0.0015 (7)
C10	0.0230 (9)	0.0346 (10)	0.0240 (9)	0.0024 (7)	0.0012 (7)	0.0020 (7)
C11	0.0249 (9)	0.0357 (10)	0.0222 (8)	0.0076 (7)	−0.0027 (7)	−0.0003 (7)
C12	0.0281 (9)	0.0199 (8)	0.0207 (8)	0.0022 (7)	−0.0044 (7)	−0.0031 (6)
C13	0.0329 (10)	0.0262 (9)	0.0189 (8)	−0.0019 (7)	−0.0055 (7)	−0.0033 (7)
C14	0.0347 (10)	0.0285 (9)	0.0254 (9)	−0.0061 (7)	0.0015 (8)	−0.0051 (7)
C15	0.0288 (10)	0.0287 (9)	0.0362 (10)	−0.0045 (7)	−0.0039 (8)	−0.0048 (8)
C16	0.0332 (10)	0.0246 (9)	0.0294 (9)	−0.0008 (7)	−0.0120 (8)	−0.0027 (7)
C17	0.0325 (9)	0.0202 (8)	0.0212 (8)	0.0013 (7)	−0.0056 (7)	−0.0019 (6)
C18	0.0360 (10)	0.0346 (10)	0.0189 (8)	0.0048 (8)	−0.0004 (7)	0.0013 (7)
P1	0.0156 (3)	0.0302 (3)	0.0175 (4)	−0.0041 (2)	−0.0011 (2)	0.0053 (3)
F1	0.0370 (7)	0.0499 (7)	0.0182 (5)	0.0021 (5)	0.0012 (4)	0.0020 (5)
F2	0.0360 (9)	0.0587 (9)	0.0220 (5)	−0.0174 (6)	−0.0105 (5)	0.0105 (5)
F3	0.0427 (9)	0.0789 (11)	0.0405 (8)	−0.0350 (8)	0.0021 (6)	0.0096 (7)
F4	0.0266 (8)	0.0901 (11)	0.0269 (6)	−0.0273 (7)	−0.0006 (6)	0.0019 (7)
F5	0.0895 (13)	0.0551 (10)	0.0322 (8)	0.0370 (9)	0.0014 (8)	−0.0026 (7)
F6	0.0558 (9)	0.0451 (9)	0.0519 (8)	0.0174 (7)	0.0044 (7)	0.0118 (7)
P1'	0.167 (16)	0.22 (2)	0.030 (7)	−0.026 (15)	−0.032 (8)	0.006 (9)
F1'	0.0370 (7)	0.0499 (7)	0.0182 (5)	0.0021 (5)	0.0012 (4)	0.0020 (5)
F2'	0.0360 (9)	0.0587 (9)	0.0220 (5)	−0.0174 (6)	−0.0105 (5)	0.0105 (5)
F3'	0.0427 (9)	0.0789 (11)	0.0405 (8)	−0.0350 (8)	0.0021 (6)	0.0096 (7)
F4'	0.0266 (8)	0.0901 (11)	0.0269 (6)	−0.0273 (7)	−0.0006 (6)	0.0019 (7)
F5'	0.0895 (13)	0.0551 (10)	0.0322 (8)	0.0370 (9)	0.0014 (8)	−0.0026 (7)
F6'	0.0558 (9)	0.0451 (9)	0.0519 (8)	0.0174 (7)	0.0044 (7)	0.0118 (7)

Geometric parameters (Å, º) top

O1—C9	1.4224 (19)	C10—C11	1.507 (2)
O1—C10	1.4266 (19)	C10—H10A	0.99
N1—C7	1.325 (2)	C10—H10B	0.99
N1—C1	1.389 (2)	C11—H11A	0.99
N1—H1N	1.05 (2)	C11—H11B	0.99
N2—C7	1.337 (2)	C12—C13	1.393 (2)
N2—C6	1.390 (2)	C12—C17	1.400 (2)
N2—C8	1.470 (2)	C13—C14	1.378 (2)
N3—C18	1.353 (2)	C13—H13	0.95
N3—C12	1.387 (2)	C14—C15	1.404 (2)
N3—C11	1.465 (2)	C14—H14	0.95
N4—C18	1.319 (2)	C15—C16	1.381 (3)
N4—C17	1.398 (2)	C15—H15	0.95
C1—C2	1.387 (2)	C16—C17	1.394 (2)
C1—C6	1.392 (2)	C16—H16	0.95
C2—C3	1.381 (2)	C18—H18	0.95
C2—H2	0.95	P1—F5	1.5742 (14)
C3—C4	1.402 (3)	P1—F3	1.5883 (13)
C3—H3	0.95	P1—F1	1.5942 (12)
C4—C5	1.375 (2)	P1—F2	1.6025 (12)
C4—H4	0.95	P1—F4	1.6041 (12)
C5—C6	1.389 (2)	P1—F6	1.6092 (14)
C5—H5	0.95	P1'—F5'	1.574 (3)
C7—H7	0.95	P1'—F3'	1.588 (3)
C8—C9	1.502 (2)	P1'—F1'	1.595 (3)
C8—H8A	0.99	P1'—F2'	1.601 (3)
C8—H8B	0.99	P1'—F4'	1.603 (3)
C9—H9A	0.99	P1'—F6'	1.608 (3)
C9—H9B	0.99

C9—O1—C10	113.54 (12)	C10—C11—H11B	109.1
C7—N1—C1	107.87 (14)	H11A—C11—H11B	107.8
C7—N1—H1N	126.9 (11)	N3—C12—C13	132.02 (15)
C1—N1—H1N	125.0 (11)	N3—C12—C17	105.74 (14)
C7—N2—C6	107.41 (13)	C13—C12—C17	122.24 (16)
C7—N2—C8	128.63 (14)	C14—C13—C12	116.68 (16)
C6—N2—C8	123.95 (13)	C14—C13—H13	121.7
C18—N3—C12	106.67 (14)	C12—C13—H13	121.7
C18—N3—C11	126.26 (15)	C13—C14—C15	121.63 (16)
C12—N3—C11	127.04 (13)	C13—C14—H14	119.2
C18—N4—C17	105.03 (14)	C15—C14—H14	119.2
C2—C1—N1	131.78 (15)	C16—C15—C14	121.52 (17)
C2—C1—C6	121.47 (15)	C16—C15—H15	119.2
N1—C1—C6	106.75 (14)	C14—C15—H15	119.2
C3—C2—C1	116.36 (16)	C15—C16—C17	117.52 (16)
C3—C2—H2	121.8	C15—C16—H16	121.2
C1—C2—H2	121.8	C17—C16—H16	121.2
C2—C3—C4	122.12 (17)	C16—C17—N4	130.48 (16)
C2—C3—H3	118.9	C16—C17—C12	120.41 (16)
C4—C3—H3	118.9	N4—C17—C12	109.11 (15)
C5—C4—C3	121.46 (16)	N4—C18—N3	113.45 (16)
C5—C4—H4	119.3	N4—C18—H18	123.3
C3—C4—H4	119.3	N3—C18—H18	123.3
C4—C5—C6	116.52 (16)	F5—P1—F3	91.33 (10)
C4—C5—H5	121.7	F5—P1—F1	90.84 (8)
C6—C5—H5	121.7	F3—P1—F1	90.37 (7)
C5—C6—N2	131.09 (15)	F5—P1—F2	90.33 (7)
C5—C6—C1	122.08 (15)	F3—P1—F2	89.90 (7)
N2—C6—C1	106.83 (14)	F1—P1—F2	178.79 (8)
N1—C7—N2	111.14 (15)	F5—P1—F4	91.13 (10)
N1—C7—H7	124.4	F3—P1—F4	177.42 (10)
N2—C7—H7	124.4	F1—P1—F4	90.37 (7)
N2—C8—C9	112.67 (13)	F2—P1—F4	89.30 (6)
N2—C8—H8A	109.1	F5—P1—F6	179.35 (8)
C9—C8—H8A	109.1	F3—P1—F6	89.03 (8)
N2—C8—H8B	109.1	F1—P1—F6	89.69 (8)
C9—C8—H8B	109.1	F2—P1—F6	89.14 (8)
H8A—C8—H8B	107.8	F4—P1—F6	88.51 (9)
O1—C9—C8	107.68 (13)	F5'—P1'—F3'	91.6 (3)
O1—C9—H9A	110.2	F5'—P1'—F1'	90.8 (3)
C8—C9—H9A	110.2	F3'—P1'—F1'	90.2 (3)
O1—C9—H9B	110.2	F5'—P1'—F2'	90.1 (3)
C8—C9—H9B	110.2	F3'—P1'—F2'	89.9 (3)
H9A—C9—H9B	108.5	F1'—P1'—F2'	179.1 (4)
O1—C10—C11	107.08 (13)	F5'—P1'—F4'	90.8 (3)
O1—C10—H10A	110.3	F3'—P1'—F4'	177.5 (4)
C11—C10—H10A	110.3	F1'—P1'—F4'	90.2 (3)
O1—C10—H10B	110.3	F2'—P1'—F4'	89.6 (3)
C11—C10—H10B	110.3	F5'—P1'—F6'	179.1 (4)
H10A—C10—H10B	108.6	F3'—P1'—F6'	89.2 (3)
N3—C11—C10	112.69 (14)	F1'—P1'—F6'	89.7 (3)
N3—C11—H11A	109.1	F2'—P1'—F6'	89.5 (3)
C10—C11—H11A	109.1	F4'—P1'—F6'	88.4 (3)
N3—C11—H11B	109.1

C7—N1—C1—C2	−179.03 (17)	C9—O1—C10—C11	169.54 (13)
C7—N1—C1—C6	0.03 (17)	C18—N3—C11—C10	−94.78 (19)
N1—C1—C2—C3	178.85 (16)	C12—N3—C11—C10	87.35 (19)
C6—C1—C2—C3	−0.1 (2)	O1—C10—C11—N3	−58.98 (17)
C1—C2—C3—C4	0.3 (3)	C18—N3—C12—C13	179.45 (17)
C2—C3—C4—C5	−0.2 (3)	C11—N3—C12—C13	−2.3 (3)
C3—C4—C5—C6	0.0 (2)	C18—N3—C12—C17	0.01 (17)
C4—C5—C6—N2	−179.17 (16)	C11—N3—C12—C17	178.22 (15)
C4—C5—C6—C1	0.2 (2)	N3—C12—C13—C14	−179.43 (16)
C7—N2—C6—C5	179.09 (16)	C17—C12—C13—C14	−0.1 (2)
C8—N2—C6—C5	−0.4 (3)	C12—C13—C14—C15	−0.2 (2)
C7—N2—C6—C1	−0.31 (17)	C13—C14—C15—C16	0.3 (3)
C8—N2—C6—C1	−179.76 (13)	C14—C15—C16—C17	−0.1 (2)
C2—C1—C6—C5	−0.1 (2)	C15—C16—C17—N4	179.34 (16)
N1—C1—C6—C5	−179.29 (14)	C15—C16—C17—C12	−0.2 (2)
C2—C1—C6—N2	179.35 (14)	C18—N4—C17—C16	−179.82 (17)
N1—C1—C6—N2	0.17 (17)	C18—N4—C17—C12	−0.29 (18)
C1—N1—C7—N2	−0.23 (18)	N3—C12—C17—C16	179.76 (14)
C6—N2—C7—N1	0.34 (18)	C13—C12—C17—C16	0.3 (2)
C8—N2—C7—N1	179.76 (14)	N3—C12—C17—N4	0.17 (17)
C7—N2—C8—C9	13.2 (2)	C13—C12—C17—N4	−179.34 (14)
C6—N2—C8—C9	−167.43 (14)	C17—N4—C18—N3	0.31 (19)
C10—O1—C9—C8	−167.47 (13)	C12—N3—C18—N4	−0.21 (19)
N2—C8—C9—O1	58.10 (17)	C11—N3—C18—N4	−178.43 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N4ⁱ	1.05 (2)	1.68 (2)	2.724 (2)	176 (2)
C4—H4···F3ⁱⁱ	0.95	2.41	3.130 (2)	133
C7—H7···F4ⁱⁱⁱ	0.95	2.23	3.100 (2)	152
C9—H9B···F2ⁱⁱⁱ	0.99	2.40	3.340 (2)	159
C11—H11A···F2^iv	0.99	2.51	3.066 (2)	116
C16—H16···F4^v	0.95	2.39	3.300 (2)	161
C18—H18···F6	0.95	2.38	3.298 (2)	163

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₉N₄O⁺·PF₆⁻
M_r	452.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	93
a, b, c (Å)	10.5347 (18), 13.771 (2), 13.353 (2)
β (°)	92.507 (2)
V (Å³)	1935.3 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.37 × 0.33 × 0.27

Data collection
Diffractometer	Rigaku SPIDER
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.923, 0.943
No. of measured, independent and observed [I > 2σ(I)] reflections	11885, 3959, 3445
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.080, 1.00
No. of reflections	3959
No. of parameters	303
No. of restraints	21
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.28

Computer programs: RAPID-AUTO (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N4ⁱ	1.05 (2)	1.68 (2)	2.724 (2)	176 (2)
C4—H4···F3ⁱⁱ	0.95	2.41	3.130 (2)	133
C7—H7···F4ⁱⁱⁱ	0.95	2.23	3.100 (2)	152
C9—H9B···F2ⁱⁱⁱ	0.99	2.40	3.340 (2)	159
C11—H11A···F2^iv	0.99	2.51	3.066 (2)	116
C16—H16···F4^v	0.95	2.39	3.300 (2)	161
C18—H18···F6	0.95	2.38	3.298 (2)	163

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

Acknowledgements

The authors thank the Scientific Researching Fund Projects of China West Normal University (grant No. 06B003) and the Youth Fund Projects of Sichuan Educational Department (grant No. 2006B039) for financial support.

References

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Murru, S., Patel, B. K., Le Bras, J. & Muzart, J. (2009). J. Org. Chem. 74, 2217–2220. Web of Science CrossRef PubMed CAS Google Scholar
Pal, S., Hwang, W.-S., Lin, I. J. B. & Lee, C.-S. (2007). J. Mol. Catal. A, 269, 197–922. CrossRef CAS Google Scholar
Rigaku/MSC (2004). RAPID-AUTO. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zeng, A., Phillips, B. S., Xiao, J.-C. & Jean'ne, M. S. (2008). Chem. Mater. 20, 2719–2726. Web of Science CrossRef CAS Google Scholar

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

1-{2-[2-(1H-Benzimidazol-1-yl)eth­­oxy]eth­yl}-1H-benzimidazol-3-ium hexa­fluoro­phosphate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-{2-[2-(1H-Benzimidazol-1-yl)ethoxy]ethyl}-1H-benzimidazol-3-ium hexafluorophosphate