2-Trifluoro-methyl-1H-benzimidazol-3-ium perchlorate.

In the title salt, C(8)H(6)F(3)N(2) (+)·ClO(4) (-), the atoms of the benzimidazole ring (including H atoms) are nearly coplanar (r.m.s. deviation of the fitted atoms = 0.0122 Å) and the triflouromethyl group lies out of this plane. The perchlorate anion adopts a distorted tetra-hedral conformation with the Cl-O bond distances ranging from 1.412 (3) to 1.439 (2) Å. The benzimidazolium cations are linked to adjacent anions by inter-molecular N-H⋯O hydrogen bonds, forming chains.

Related literature

For background to mol­ecular–ionic compounds, see: Yu et al. (2004 ▶); Chen et al. (2009 ▶); Ge et al. (2007 ▶).

Experimental

Crystal data

C8H6F3N2 +·ClO4 −

M = 286.60

Triclinic,

a = 7.6274 (15) Å

b = 9.0614 (18) Å

c = 9.3838 (19) Å

α = 61.80 (3)°

β = 81.98 (3)°

γ = 75.85 (3)°

V = 554.0 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.40 mm−1

T = 293 K

0.36 × 0.32 × 0.28 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.963, T max = 0.971

5756 measured reflections

2535 independent reflections

1980 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.140

S = 1.04

2535 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811039298/go2027sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039298/go2027Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811039298/go2027Isup3.cml

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

C8H6F3N2+·ClO4−	V = 554.0 (3) Å3
Mr = 286.60	Z = 2
Triclinic, P1	F(000) = 288
Hall symbol: -P 1	Dx = 1.718 Mg m−3
a = 7.6274 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.0614 (18) Å	θ = 3.4–26°
c = 9.3838 (19) Å	µ = 0.40 mm−1
α = 61.80 (3)°	T = 293 K
β = 81.98 (3)°	Block, colourless
γ = 75.85 (3)°	0.36 × 0.32 × 0.28 mm

Rigaku Mercury2 diffractometer	2535 independent reflections
Radiation source: fine-focus sealed tube	1980 reflections with I > 2σ(I)
graphite	Rint = 0.026
CCD_Profile_fitting scans	θmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −9→9
Tmin = 0.963, Tmax = 0.971	k = −11→11
5756 measured reflections	l = −12→12

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0636P)2 + 0.384P] where P = (Fo2 + 2Fc2)/3
2535 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

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.

	x	y	z	Uiso*/Ueq
F1	0.3287 (4)	0.0295 (2)	0.1487 (2)	0.0793 (7)
F2	0.4027 (3)	0.2471 (3)	−0.0564 (2)	0.0697 (6)
F3	0.1269 (3)	0.2305 (3)	−0.0094 (3)	0.0791 (7)
N1	0.2447 (3)	0.4517 (3)	0.1052 (3)	0.0430 (5)
H1A	0.2375	0.5249	0.0045	0.052*
N2	0.2695 (3)	0.2099 (3)	0.3226 (2)	0.0379 (5)
H2A	0.2802	0.1020	0.3852	0.046*
C1	0.2548 (3)	0.3343 (3)	0.3721 (3)	0.0374 (5)
C2	0.2378 (4)	0.4892 (3)	0.2328 (3)	0.0395 (6)
C3	0.2214 (4)	0.6432 (4)	0.2384 (4)	0.0534 (7)
H3	0.2090	0.7476	0.1453	0.064*
C4	0.2248 (5)	0.6313 (4)	0.3883 (4)	0.0603 (8)
H4	0.2148	0.7308	0.3976	0.072*
C5	0.2429 (5)	0.4748 (4)	0.5284 (4)	0.0593 (8)
H5	0.2448	0.4737	0.6277	0.071*
C6	0.2577 (4)	0.3237 (4)	0.5248 (3)	0.0510 (7)
H6	0.2691	0.2199	0.6185	0.061*
C7	0.2639 (3)	0.2848 (3)	0.1636 (3)	0.0376 (5)
C8	0.2812 (4)	0.1957 (4)	0.0614 (3)	0.0483 (7)
Cl1	0.21788 (9)	0.83165 (8)	−0.28977 (7)	0.0426 (2)
O1	0.3244 (3)	0.8661 (3)	−0.4364 (2)	0.0571 (6)
O2	0.1589 (4)	0.6730 (3)	−0.2310 (3)	0.0692 (7)
O3	0.3197 (4)	0.8220 (5)	−0.1699 (3)	0.0965 (10)
O4	0.0612 (4)	0.9641 (3)	−0.3218 (3)	0.0806 (8)

	U11	U22	U33	U12	U13	U23
F1	0.131 (2)	0.0469 (11)	0.0617 (12)	−0.0124 (11)	−0.0017 (12)	−0.0287 (9)
F2	0.0740 (13)	0.0940 (15)	0.0507 (10)	−0.0281 (11)	0.0205 (9)	−0.0414 (10)
F3	0.0649 (12)	0.1233 (19)	0.0777 (14)	−0.0174 (12)	−0.0104 (10)	−0.0676 (14)
N1	0.0551 (13)	0.0378 (11)	0.0265 (10)	−0.0127 (10)	0.0002 (9)	−0.0058 (9)
N2	0.0466 (12)	0.0319 (10)	0.0273 (10)	−0.0068 (9)	−0.0029 (9)	−0.0071 (8)
C1	0.0396 (13)	0.0364 (13)	0.0318 (12)	−0.0081 (10)	−0.0015 (10)	−0.0118 (10)
C2	0.0442 (14)	0.0383 (13)	0.0316 (12)	−0.0115 (11)	−0.0005 (10)	−0.0112 (10)
C3	0.068 (2)	0.0385 (14)	0.0502 (17)	−0.0166 (14)	−0.0008 (14)	−0.0149 (13)
C4	0.076 (2)	0.0521 (18)	0.065 (2)	−0.0212 (16)	0.0012 (17)	−0.0337 (16)
C5	0.076 (2)	0.068 (2)	0.0453 (16)	−0.0156 (17)	−0.0024 (15)	−0.0339 (16)
C6	0.0646 (18)	0.0515 (16)	0.0323 (13)	−0.0109 (14)	−0.0049 (12)	−0.0149 (12)
C7	0.0389 (13)	0.0394 (13)	0.0291 (12)	−0.0098 (10)	0.0010 (10)	−0.0111 (10)
C8	0.0560 (17)	0.0536 (16)	0.0374 (14)	−0.0143 (13)	0.0025 (12)	−0.0219 (13)
Cl1	0.0500 (4)	0.0392 (3)	0.0302 (3)	−0.0106 (3)	−0.0028 (2)	−0.0079 (2)
O1	0.0636 (13)	0.0512 (12)	0.0351 (10)	−0.0059 (10)	0.0047 (9)	−0.0067 (9)
O2	0.0965 (18)	0.0503 (13)	0.0569 (14)	−0.0310 (12)	0.0130 (13)	−0.0178 (11)
O3	0.091 (2)	0.158 (3)	0.0524 (14)	−0.057 (2)	−0.0063 (14)	−0.0410 (17)
O4	0.0728 (16)	0.0586 (15)	0.0820 (18)	0.0036 (12)	0.0105 (14)	−0.0207 (13)

F1—C8	1.312 (4)	C3—C4	1.363 (4)
F2—C8	1.317 (3)	C3—H3	0.9300
F3—C8	1.328 (4)	C4—C5	1.397 (5)
N1—C7	1.318 (3)	C4—H4	0.9300
N1—C2	1.382 (3)	C5—C6	1.362 (4)
N1—H1A	0.86	C5—H5	0.9300
N2—C7	1.318 (3)	C6—H6	0.9300
N2—C1	1.385 (3)	C7—C8	1.495 (4)
N2—H2A	0.86	Cl1—O3	1.412 (3)
C1—C2	1.385 (3)	Cl1—O4	1.420 (3)
C1—C6	1.393 (4)	Cl1—O1	1.434 (2)
C2—C3	1.395 (4)	Cl1—O2	1.439 (2)
C7—N1—C2	108.6 (2)	C4—C5—H5	118.8
C7—N1—H1A	125.7	C5—C6—C1	115.8 (3)
C2—N1—H1A	125.8	C5—C6—H6	122.1
C7—N2—C1	108.5 (2)	C1—C6—H6	122.1
C7—N2—H2A	125.8	N2—C7—N1	110.3 (2)
C1—N2—H2A	125.7	N2—C7—C8	125.6 (2)
N2—C1—C2	106.3 (2)	N1—C7—C8	124.1 (2)
N2—C1—C6	131.7 (2)	F1—C8—F2	108.7 (3)
C2—C1—C6	121.9 (3)	F1—C8—F3	108.6 (3)
N1—C2—C1	106.3 (2)	F2—C8—F3	106.2 (2)
N1—C2—C3	132.0 (2)	F1—C8—C7	110.7 (2)
C1—C2—C3	121.6 (3)	F2—C8—C7	111.0 (2)
C4—C3—C2	116.0 (3)	F3—C8—C7	111.4 (2)
C4—C3—H3	122.0	O3—Cl1—O4	110.0 (2)
C2—C3—H3	122.0	O3—Cl1—O1	110.25 (16)
C3—C4—C5	122.2 (3)	O4—Cl1—O1	109.06 (15)
C3—C4—H4	118.9	O3—Cl1—O2	109.08 (18)
C5—C4—H4	118.9	O4—Cl1—O2	107.71 (17)
C6—C5—C4	122.4 (3)	O1—Cl1—O2	110.65 (15)
C6—C5—H5	118.8
C7—N2—C1—C2	0.7 (3)	N2—C1—C6—C5	178.7 (3)
C7—N2—C1—C6	−178.2 (3)	C2—C1—C6—C5	0.0 (4)
C7—N1—C2—C1	0.2 (3)	C1—N2—C7—N1	−0.6 (3)
C7—N1—C2—C3	179.0 (3)	C1—N2—C7—C8	178.0 (2)
N2—C1—C2—N1	−0.5 (3)	C2—N1—C7—N2	0.2 (3)
C6—C1—C2—N1	178.5 (3)	C2—N1—C7—C8	−178.4 (2)
N2—C1—C2—C3	−179.4 (2)	N2—C7—C8—F1	−9.0 (4)
C6—C1—C2—C3	−0.5 (4)	N1—C7—C8—F1	169.4 (3)
N1—C2—C3—C4	−178.0 (3)	N2—C7—C8—F2	−129.8 (3)
C1—C2—C3—C4	0.6 (4)	N1—C7—C8—F2	48.6 (4)
C2—C3—C4—C5	−0.2 (5)	N2—C7—C8—F3	112.1 (3)
C3—C4—C5—C6	−0.2 (6)	N1—C7—C8—F3	−69.5 (3)
C4—C5—C6—C1	0.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.86	2.05	2.891 (3)	164
N1—H1A···O3	0.86	2.59	3.254 (4)	135
N2—H2A···O1i	0.86	1.98	2.822 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2	0.86	2.05	2.891 (3)	164
N1—H1A⋯O3	0.86	2.59	3.254 (4)	135
N2—H2A⋯O1i	0.86	1.98	2.822 (3)	167

Symmetry code: (i) .