3,3'-Dicyclo-pentyl-1,1'-(1,3-phenyl-enedimethyl-ene)dibenzimidazol-1-ium bis-(hexa-fluoro-phosphate).

In the title compound, C(32)H(36)N(4) (2+)·2PF(6) (-), the cation and the anions each have crystallographic twofold rotation symmetry. The benzimidazole ring is almost planar [r.m.s. deviation = 0.0161 (1) Å] and makes a dihedral angle of 5.77 (4)° with its symmetry-related component and a dihedral angle of 80.96 (5)° with the central benzene ring. The cyclo-pentyl ring adopts a half-chair conformation. In the crystal, mol-ecules are linked into a three-dimensional network through C-H⋯F hydrogen bonds. A C-H⋯π inter-action is also observed.

Related literature

For the biological activity of benzimidazole, see: Shaharyar et al. (2012 ▶); Mohan et al. (2011 ▶). For related structures, see: Haque et al. (2011 ▶, 2012 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C32H36N4 2+·2PF6 −

M = 766.59

Orthorhombic,

a = 7.0699 (1) Å

b = 20.4852 (3) Å

c = 22.5416 (3) Å

V = 3264.66 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 100 K

0.44 × 0.13 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.903, T max = 0.974

19037 measured reflections

4758 independent reflections

4407 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.078

S = 1.05

4758 reflections

228 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), 2086 Friedel pairs

Flack parameter: 0.02 (7)

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

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681202274X/rz2756sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202274X/rz2756Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681202274X/rz2756Isup3.cml

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

C32H36N42+·2PF6−	F(000) = 1576
Mr = 766.59	Dx = 1.560 Mg m−3
Orthorhombic, C2221	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2c 2	Cell parameters from 9943 reflections
a = 7.0699 (1) Å	θ = 2.2–29.9°
b = 20.4852 (3) Å	µ = 0.23 mm−1
c = 22.5416 (3) Å	T = 100 K
V = 3264.66 (8) Å3	Block, colourless
Z = 4	0.44 × 0.13 × 0.11 mm

Bruker SMART APEXII CCD area-detector diffractometer	4758 independent reflections
Radiation source: fine-focus sealed tube	4407 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 30.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
Tmin = 0.903, Tmax = 0.974	k = −28→28
19037 measured reflections	l = −28→31

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032	H-atom parameters constrained
wR(F2) = 0.078	w = 1/[σ2(Fo2) + (0.0411P)2 + 1.0871P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
4758 reflections	Δρmax = 0.29 e Å−3
228 parameters	Δρmin = −0.24 e Å−3
0 restraints	Absolute structure: Flack (1983), 2086 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.02 (7)

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

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
P1	0.12643 (8)	0.0000	0.5000	0.01579 (10)
F1	−0.03216 (16)	0.05234 (5)	0.48352 (4)	0.0333 (2)
F2	0.28761 (15)	0.05230 (5)	0.48369 (4)	0.0313 (2)
F3	0.12649 (14)	0.02573 (5)	0.56726 (4)	0.02558 (19)
P2	0.0000	0.20928 (3)	0.7500	0.01858 (11)
F4	0.03085 (15)	0.26421 (5)	0.79953 (4)	0.0304 (2)
F5	−0.03160 (16)	0.15392 (5)	0.70063 (4)	0.0331 (2)
F6	0.22344 (14)	0.20932 (5)	0.73648 (4)	0.0307 (2)
N1	0.01439 (18)	0.21030 (6)	0.37157 (5)	0.0166 (2)
N2	−0.04694 (17)	0.31380 (6)	0.38710 (5)	0.0158 (2)
C1	0.0000	0.01437 (9)	0.2500	0.0217 (4)
H1A	0.0000	−0.0320	0.2500	0.026*
C2	0.0497 (2)	0.04841 (7)	0.30090 (7)	0.0187 (3)
H2A	0.0830	0.0252	0.3359	0.022*
C3	0.0511 (2)	0.11646 (6)	0.30090 (6)	0.0155 (3)
C4	0.0000	0.15040 (9)	0.2500	0.0171 (4)
H4A	0.0000	0.1968	0.2500	0.020*
C5	0.1218 (2)	0.15116 (6)	0.35629 (6)	0.0184 (3)
H5A	0.1158	0.1204	0.3901	0.022*
H5B	0.2561	0.1632	0.3504	0.022*
C6	−0.1642 (2)	0.21287 (7)	0.39812 (6)	0.0159 (3)
C7	−0.2882 (2)	0.16395 (7)	0.41598 (7)	0.0203 (3)
H7A	−0.2614	0.1191	0.4095	0.024*
C8	−0.4523 (2)	0.18423 (7)	0.44364 (7)	0.0215 (3)
H8A	−0.5404	0.1524	0.4568	0.026*
C9	−0.4927 (2)	0.25100 (7)	0.45287 (6)	0.0194 (3)
H9A	−0.6077	0.2628	0.4718	0.023*
C10	−0.3694 (2)	0.29965 (7)	0.43506 (6)	0.0168 (3)
H10A	−0.3966	0.3446	0.4411	0.020*
C11	−0.2030 (2)	0.27901 (6)	0.40778 (6)	0.0157 (3)
C12	0.0780 (2)	0.27128 (7)	0.36572 (6)	0.0173 (3)
H12A	0.1962	0.2828	0.3486	0.021*
C13	−0.0262 (2)	0.38548 (6)	0.38878 (7)	0.0187 (3)
H13A	−0.1242	0.4034	0.4163	0.022*
C14	−0.0516 (3)	0.41777 (8)	0.32852 (8)	0.0328 (4)
H14A	−0.1872	0.4213	0.3181	0.039*
H14B	0.0147	0.3929	0.2971	0.039*
C15	0.0376 (3)	0.48588 (8)	0.33678 (10)	0.0377 (5)
H15A	0.1187	0.4970	0.3024	0.045*
H15B	−0.0620	0.5196	0.3407	0.045*
C16	0.1564 (2)	0.48203 (7)	0.39385 (8)	0.0258 (3)
H16A	0.2848	0.4998	0.3871	0.031*
H16B	0.0956	0.5070	0.4262	0.031*
C17	0.1659 (2)	0.40913 (7)	0.40946 (7)	0.0233 (3)
H17A	0.2696	0.3870	0.3879	0.028*
H17B	0.1828	0.4024	0.4526	0.028*

	U11	U22	U33	U12	U13	U23
P1	0.0180 (2)	0.0139 (2)	0.0155 (2)	0.000	0.000	0.00104 (18)
F1	0.0360 (6)	0.0354 (5)	0.0287 (5)	0.0206 (4)	−0.0024 (4)	−0.0028 (4)
F2	0.0348 (6)	0.0286 (5)	0.0304 (5)	−0.0119 (4)	0.0112 (4)	0.0012 (4)
F3	0.0298 (5)	0.0311 (4)	0.0158 (4)	−0.0089 (4)	0.0008 (4)	−0.0032 (4)
P2	0.0195 (3)	0.0204 (2)	0.0159 (2)	0.000	−0.0036 (2)	0.000
F4	0.0330 (6)	0.0316 (5)	0.0266 (5)	0.0000 (4)	−0.0041 (4)	−0.0115 (4)
F5	0.0414 (6)	0.0304 (5)	0.0276 (5)	−0.0014 (5)	−0.0082 (5)	−0.0105 (4)
F6	0.0202 (5)	0.0419 (5)	0.0300 (6)	0.0038 (4)	−0.0009 (4)	−0.0035 (4)
N1	0.0196 (6)	0.0151 (5)	0.0152 (5)	−0.0003 (5)	0.0004 (5)	−0.0011 (4)
N2	0.0162 (6)	0.0144 (5)	0.0168 (6)	−0.0026 (4)	0.0024 (4)	−0.0011 (4)
C1	0.0268 (11)	0.0110 (8)	0.0273 (11)	0.000	−0.0015 (9)	0.000
C2	0.0206 (7)	0.0158 (6)	0.0197 (7)	0.0016 (5)	0.0000 (6)	0.0027 (5)
C3	0.0161 (6)	0.0135 (6)	0.0169 (6)	0.0001 (5)	0.0011 (5)	−0.0018 (5)
C4	0.0208 (9)	0.0116 (8)	0.0188 (9)	0.000	0.0011 (8)	0.000
C5	0.0219 (7)	0.0146 (6)	0.0186 (7)	0.0048 (6)	−0.0030 (6)	−0.0007 (5)
C6	0.0186 (7)	0.0180 (6)	0.0111 (6)	−0.0010 (5)	−0.0022 (5)	0.0007 (5)
C7	0.0241 (8)	0.0165 (6)	0.0202 (7)	−0.0031 (5)	−0.0041 (6)	0.0024 (5)
C8	0.0221 (7)	0.0226 (7)	0.0199 (7)	−0.0079 (6)	−0.0005 (6)	0.0058 (6)
C9	0.0168 (7)	0.0252 (7)	0.0163 (6)	−0.0033 (6)	0.0004 (6)	0.0029 (5)
C10	0.0183 (6)	0.0175 (6)	0.0145 (6)	−0.0002 (5)	0.0002 (5)	0.0004 (5)
C11	0.0194 (7)	0.0156 (6)	0.0121 (6)	−0.0036 (5)	−0.0014 (5)	0.0002 (5)
C12	0.0190 (7)	0.0182 (6)	0.0149 (6)	−0.0012 (5)	0.0012 (5)	−0.0004 (5)
C13	0.0191 (7)	0.0116 (5)	0.0253 (7)	−0.0020 (5)	0.0043 (6)	−0.0021 (5)
C14	0.0383 (10)	0.0226 (8)	0.0376 (10)	−0.0044 (7)	−0.0151 (8)	0.0105 (7)
C15	0.0298 (9)	0.0254 (8)	0.0578 (13)	−0.0078 (7)	−0.0142 (9)	0.0182 (8)
C16	0.0223 (8)	0.0176 (7)	0.0376 (9)	−0.0050 (5)	0.0037 (7)	−0.0022 (6)
C17	0.0241 (8)	0.0192 (7)	0.0267 (8)	−0.0060 (6)	−0.0051 (6)	−0.0001 (6)

P1—F1	1.5951 (10)	C5—H5A	0.9900
P1—F1i	1.5952 (10)	C5—H5B	0.9900
P1—F3	1.6051 (9)	C6—C7	1.391 (2)
P1—F3i	1.6051 (9)	C6—C11	1.3993 (19)
P1—F2	1.6067 (10)	C7—C8	1.381 (2)
P1—F2i	1.6067 (10)	C7—H7A	0.9500
P2—F4ii	1.6002 (10)	C8—C9	1.413 (2)
P2—F4	1.6002 (10)	C8—H8A	0.9500
P2—F5	1.6046 (10)	C9—C10	1.384 (2)
P2—F5ii	1.6046 (10)	C9—H9A	0.9500
P2—F6	1.6088 (10)	C10—C11	1.393 (2)
P2—F6ii	1.6088 (10)	C10—H10A	0.9500
N1—C12	1.3342 (18)	C12—H12A	0.9500
N1—C6	1.3981 (19)	C13—C17	1.515 (2)
N1—C5	1.4707 (17)	C13—C14	1.522 (2)
N2—C12	1.3307 (18)	C13—H13A	1.0000
N2—C11	1.3935 (18)	C14—C15	1.542 (2)
N2—C13	1.4762 (17)	C14—H14A	0.9900
C1—C2iii	1.3879 (18)	C14—H14B	0.9900
C1—C2	1.3879 (18)	C15—C16	1.538 (3)
C1—H1A	0.9500	C15—H15A	0.9900
C2—C3	1.3942 (19)	C15—H15B	0.9900
C2—H2A	0.9500	C16—C17	1.536 (2)
C3—C4	1.3894 (17)	C16—H16A	0.9900
C3—C5	1.5210 (19)	C16—H16B	0.9900
C4—C3iii	1.3894 (17)	C17—H17A	0.9900
C4—H4A	0.9500	C17—H17B	0.9900
F1—P1—F1i	90.68 (9)	H5A—C5—H5B	107.6
F1—P1—F3	89.97 (5)	C7—C6—N1	131.74 (13)
F1i—P1—F3	90.05 (5)	C7—C6—C11	121.94 (14)
F1—P1—F3i	90.05 (5)	N1—C6—C11	106.27 (12)
F1i—P1—F3i	89.97 (5)	C8—C7—C6	116.32 (13)
F3—P1—F3i	179.97 (8)	C8—C7—H7A	121.8
F1—P1—F2	89.83 (6)	C6—C7—H7A	121.8
F1i—P1—F2	179.47 (7)	C7—C8—C9	121.84 (14)
F3—P1—F2	89.83 (5)	C7—C8—H8A	119.1
F3i—P1—F2	90.15 (5)	C9—C8—H8A	119.1
F1—P1—F2i	179.47 (7)	C10—C9—C8	121.82 (14)
F1i—P1—F2i	89.83 (6)	C10—C9—H9A	119.1
F3—P1—F2i	90.15 (5)	C8—C9—H9A	119.1
F3i—P1—F2i	89.83 (5)	C9—C10—C11	116.20 (12)
F2—P1—F2i	89.66 (8)	C9—C10—H10A	121.9
F4ii—P2—F4	90.62 (8)	C11—C10—H10A	121.9
F4ii—P2—F5	89.66 (5)	C10—C11—N2	131.36 (12)
F4—P2—F5	179.64 (6)	C10—C11—C6	121.87 (13)
F4ii—P2—F5ii	179.64 (6)	N2—C11—C6	106.74 (12)
F4—P2—F5ii	89.66 (5)	N2—C12—N1	110.70 (13)
F5—P2—F5ii	90.05 (8)	N2—C12—H12A	124.6
F4ii—P2—F6	90.07 (6)	N1—C12—H12A	124.6
F4—P2—F6	89.89 (6)	N2—C13—C17	114.52 (12)
F5—P2—F6	90.33 (6)	N2—C13—C14	113.44 (12)
F5ii—P2—F6	89.72 (6)	C17—C13—C14	103.97 (13)
F4ii—P2—F6ii	89.88 (6)	N2—C13—H13A	108.2
F4—P2—F6ii	90.07 (6)	C17—C13—H13A	108.2
F5—P2—F6ii	89.71 (6)	C14—C13—H13A	108.2
F5ii—P2—F6ii	90.33 (6)	C13—C14—C15	103.71 (14)
F6—P2—F6ii	179.94 (9)	C13—C14—H14A	111.0
C12—N1—C6	108.13 (12)	C15—C14—H14A	111.0
C12—N1—C5	125.04 (13)	C13—C14—H14B	111.0
C6—N1—C5	126.70 (12)	C15—C14—H14B	111.0
C12—N2—C11	108.16 (11)	H14A—C14—H14B	109.0
C12—N2—C13	126.47 (12)	C16—C15—C14	106.14 (13)
C11—N2—C13	125.37 (12)	C16—C15—H15A	110.5
C2iii—C1—C2	119.68 (17)	C14—C15—H15A	110.5
C2iii—C1—H1A	120.2	C16—C15—H15B	110.5
C2—C1—H1A	120.2	C14—C15—H15B	110.5
C1—C2—C3	120.28 (14)	H15A—C15—H15B	108.7
C1—C2—H2A	119.9	C17—C16—C15	105.39 (13)
C3—C2—H2A	119.9	C17—C16—H16A	110.7
C4—C3—C2	119.91 (13)	C15—C16—H16A	110.7
C4—C3—C5	121.97 (12)	C17—C16—H16B	110.7
C2—C3—C5	118.01 (12)	C15—C16—H16B	110.7
C3iii—C4—C3	119.95 (17)	H16A—C16—H16B	108.8
C3iii—C4—H4A	120.0	C13—C17—C16	101.60 (12)
C3—C4—H4A	120.0	C13—C17—H17A	111.5
N1—C5—C3	114.05 (12)	C16—C17—H17A	111.5
N1—C5—H5A	108.7	C13—C17—H17B	111.5
C3—C5—H5A	108.7	C16—C17—H17B	111.5
N1—C5—H5B	108.7	H17A—C17—H17B	109.3
C3—C5—H5B	108.7
C2iii—C1—C2—C3	−0.43 (10)	C12—N2—C11—C6	0.54 (16)
C1—C2—C3—C4	0.9 (2)	C13—N2—C11—C6	−179.62 (13)
C1—C2—C3—C5	−175.19 (12)	C7—C6—C11—C10	−1.0 (2)
C2—C3—C4—C3iii	−0.43 (10)	N1—C6—C11—C10	−178.56 (12)
C5—C3—C4—C3iii	175.47 (15)	C7—C6—C11—N2	177.31 (13)
C12—N1—C5—C3	−108.17 (16)	N1—C6—C11—N2	−0.29 (15)
C6—N1—C5—C3	76.47 (17)	C11—N2—C12—N1	−0.60 (17)
C4—C3—C5—N1	42.77 (18)	C13—N2—C12—N1	179.57 (13)
C2—C3—C5—N1	−141.25 (14)	C6—N1—C12—N2	0.41 (16)
C12—N1—C6—C7	−177.33 (15)	C5—N1—C12—N2	−175.68 (13)
C5—N1—C6—C7	−1.3 (2)	C12—N2—C13—C17	−44.6 (2)
C12—N1—C6—C11	−0.06 (15)	C11—N2—C13—C17	135.57 (14)
C5—N1—C6—C11	175.94 (13)	C12—N2—C13—C14	74.5 (2)
N1—C6—C7—C8	177.12 (14)	C11—N2—C13—C14	−105.29 (17)
C11—C6—C7—C8	0.2 (2)	N2—C13—C14—C15	−162.32 (14)
C6—C7—C8—C9	0.5 (2)	C17—C13—C14—C15	−37.29 (18)
C7—C8—C9—C10	−0.5 (2)	C13—C14—C15—C16	15.5 (2)
C8—C9—C10—C11	−0.3 (2)	C14—C15—C16—C17	11.4 (2)
C9—C10—C11—N2	−176.85 (14)	N2—C13—C17—C16	168.57 (13)
C9—C10—C11—C6	1.0 (2)	C14—C13—C17—C16	44.24 (15)
C12—N2—C11—C10	178.59 (15)	C15—C16—C17—C13	−33.95 (17)
C13—N2—C11—C10	−1.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···F3i	0.95	2.44	3.3814 (18)	171
C5—H5B···F4iv	0.99	2.41	3.2670 (17)	145
C8—H8A···F2v	0.95	2.46	3.3912 (18)	167
C12—H12A···F4iv	0.95	2.42	3.2252 (17)	142
C13—H13A···F2vi	1.00	2.51	3.4090 (18)	150
C13—H13A···F3vi	1.00	2.31	3.2124 (17)	149
C9—H9A···Cg1vi	0.95	2.79	3.6416 (15)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯F3i	0.95	2.44	3.3814 (18)	171
C5—H5B⋯F4ii	0.99	2.41	3.2670 (17)	145
C8—H8A⋯F2iii	0.95	2.46	3.3912 (18)	167
C12—H12A⋯F4ii	0.95	2.42	3.2252 (17)	142
C13—H13A⋯F2iv	1.00	2.51	3.4090 (18)	150
C13—H13A⋯F3iv	1.00	2.31	3.2124 (17)	149
C9—H9A⋯Cg1iv	0.95	2.79	3.6416 (15)	149

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