2-Trifluoro-methyl-1H-benzimidazol-3-ium hydrogen sulfate.

In the crystal of the title mol-ecular salt, C(8)H(6)F(3)N(2) (+)·HSO(4) (-), cation-to-anion N-H⋯O hydrogen bonds generate [100] chains. Anion-to-anion O-H⋯O hydrogen bonds generate [001] helices and cross-link the chains into a three-dimensional network.

Related literature

For a related structure and background to mol­ecular salts, see: Liu (2011 ▶).

Experimental

Crystal data

C8H6F3N2 +·HSO4 −

M = 284.22

Hexagonal,

a = 9.4119 (13) Å

c = 21.960 (4) Å

V = 1684.7 (5) Å3

Z = 6

Mo Kα radiation

μ = 0.34 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury2 CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.935, T max = 0.935

14287 measured reflections

1977 independent reflections

1941 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.134

S = 1.11

1977 reflections

167 parameters

8 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.53 e Å−3

Δρmin = −0.25 e Å−3

Absolute structure: Flack (1983 ▶), 957 Friedel pairs

Flack parameter: 0.03 (16)

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 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811048811/hb6491sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048811/hb6491Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811048811/hb6491Isup3.cml

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

C8H6F3N2+·HSO4−	F(000) = 864
Mr = 284.22	Dx = 1.681 Mg m−3
Hexagonal, P65	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 65	θ = 3.1–27.6°
a = 9.4119 (13) Å	µ = 0.34 mm−1
c = 21.960 (4) Å	T = 293 K
V = 1684.7 (5) Å3	Block, colorless
Z = 6	0.20 × 0.20 × 0.20 mm

Rigaku Mercury2 CCD diffractometer	1977 independent reflections
Radiation source: fine-focus sealed tube	1941 reflections with I > 2σ(I)
graphite	Rint = 0.038
CCD_Profile_fitting scans	θmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −11→11
Tmin = 0.935, Tmax = 0.935	k = −11→11
14287 measured reflections	l = −26→26

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)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.134	w = 1/[σ2(Fo2) + (0.0593P)2 + 1.9666P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max < 0.001
1977 reflections	Δρmax = 0.53 e Å−3
167 parameters	Δρmin = −0.25 e Å−3
8 restraints	Absolute structure: Flack (1983), 957 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.03 (16)

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
S1	0.09970 (14)	0.72553 (17)	0.16867 (6)	0.0442 (3)
N1	0.4873 (5)	0.7391 (5)	0.1735 (2)	0.0418 (9)
H1A	0.3843	0.7058	0.1770	0.050*
N2	0.7169 (4)	0.7349 (5)	0.16388 (17)	0.0348 (8)
H2A	0.7835	0.6981	0.1596	0.042*
C3	0.6124 (6)	0.9017 (6)	0.1722 (2)	0.0418 (11)
C8	0.7613 (5)	0.9011 (6)	0.1675 (2)	0.0371 (10)
C4	0.6126 (7)	1.0512 (7)	0.1762 (3)	0.0508 (13)
H4	0.5152	1.0535	0.1792	0.061*
O3	−0.0637 (4)	0.6347 (5)	0.14218 (18)	0.0558 (11)
F3	0.5450 (5)	0.4034 (5)	0.1391 (3)	0.0928 (15)
C6	0.9082 (7)	1.1891 (7)	0.1712 (3)	0.0527 (13)
H6	1.0066	1.2883	0.1710	0.063*
O1	0.0866 (5)	0.8248 (5)	0.2230 (2)	0.0627 (11)
C5	0.7592 (8)	1.1907 (7)	0.1755 (3)	0.0589 (15)
H5	0.7623	1.2909	0.1780	0.071*
F1	0.3262 (5)	0.4077 (6)	0.1346 (3)	0.116 (2)
F2	0.4211 (10)	0.3991 (6)	0.2195 (2)	0.157 (3)
O4	0.1589 (5)	0.6207 (5)	0.19150 (19)	0.0571 (11)
C7	0.9120 (6)	1.0455 (7)	0.1670 (3)	0.0456 (11)
H7	1.0103	1.0448	0.1641	0.055*
C1	0.4609 (6)	0.4596 (7)	0.1670 (3)	0.0520 (13)
O2	0.2184 (6)	0.8507 (9)	0.1300 (3)	0.110 (2)
C2	0.5531 (5)	0.6434 (6)	0.1683 (2)	0.0373 (9)
H1	0.041 (10)	0.754 (9)	0.251 (3)	0.10 (3)*

	U11	U22	U33	U12	U13	U23
S1	0.0252 (5)	0.0626 (9)	0.0458 (6)	0.0227 (5)	0.0080 (5)	0.0144 (6)
N1	0.0295 (19)	0.051 (2)	0.051 (2)	0.0252 (19)	−0.0012 (18)	−0.0049 (19)
N2	0.0243 (17)	0.044 (2)	0.040 (2)	0.0205 (16)	0.0009 (16)	−0.0062 (18)
C3	0.037 (2)	0.050 (3)	0.043 (3)	0.025 (2)	0.001 (2)	−0.002 (2)
C8	0.037 (2)	0.043 (3)	0.037 (2)	0.024 (2)	−0.006 (2)	−0.005 (2)
C4	0.057 (3)	0.058 (3)	0.059 (3)	0.044 (3)	−0.002 (3)	0.003 (3)
O3	0.0362 (19)	0.087 (3)	0.059 (2)	0.042 (2)	−0.0057 (16)	−0.015 (2)
F3	0.070 (2)	0.058 (2)	0.158 (4)	0.038 (2)	0.018 (3)	−0.012 (3)
C6	0.044 (3)	0.045 (3)	0.062 (3)	0.017 (2)	0.006 (3)	0.009 (3)
O1	0.056 (3)	0.048 (2)	0.079 (3)	0.022 (2)	−0.009 (2)	−0.012 (2)
C5	0.073 (4)	0.052 (3)	0.070 (4)	0.045 (3)	−0.005 (3)	0.005 (3)
F1	0.047 (2)	0.070 (3)	0.213 (6)	0.0161 (19)	−0.039 (3)	−0.044 (3)
F2	0.246 (6)	0.055 (3)	0.072 (3)	0.002 (3)	0.038 (4)	0.009 (2)
O4	0.0403 (19)	0.074 (3)	0.072 (3)	0.039 (2)	0.0007 (17)	0.007 (2)
C7	0.030 (2)	0.055 (3)	0.050 (3)	0.020 (2)	−0.002 (2)	0.003 (2)
C1	0.036 (3)	0.043 (3)	0.067 (3)	0.012 (2)	0.014 (3)	−0.001 (3)
O2	0.057 (3)	0.155 (5)	0.108 (4)	0.045 (3)	0.032 (3)	0.093 (4)
C2	0.030 (2)	0.040 (2)	0.042 (2)	0.0176 (19)	0.0001 (19)	−0.010 (2)

S1—O2	1.429 (5)	C4—C5	1.348 (9)
S1—O4	1.444 (4)	C4—H4	0.9300
S1—O3	1.456 (4)	F3—C1	1.304 (6)
S1—O1	1.558 (5)	C6—C7	1.373 (8)
N1—C2	1.329 (6)	C6—C5	1.414 (8)
N1—C3	1.388 (6)	C6—H6	0.9300
N1—H1A	0.8600	O1—H1	0.86 (2)
N2—C2	1.341 (6)	C5—H5	0.9300
N2—C8	1.405 (6)	F1—C1	1.317 (8)
N2—H2A	0.8600	F2—C1	1.258 (8)
C3—C8	1.407 (6)	C7—H7	0.9300
C3—C4	1.409 (7)	C1—C2	1.499 (7)
C8—C7	1.390 (7)
O2—S1—O4	111.1 (3)	C3—C4—H4	121.2
O2—S1—O3	114.0 (3)	C7—C6—C5	122.0 (5)
O4—S1—O3	113.1 (3)	C7—C6—H6	119.0
O2—S1—O1	103.0 (4)	C5—C6—H6	119.0
O4—S1—O1	108.5 (3)	S1—O1—H1	104 (7)
O3—S1—O1	106.3 (2)	C4—C5—C6	121.9 (5)
C2—N1—C3	108.6 (4)	C4—C5—H5	119.1
C2—N1—H1A	125.7	C6—C5—H5	119.1
C3—N1—H1A	125.7	C6—C7—C8	116.5 (4)
C2—N2—C8	108.5 (3)	C6—C7—H7	121.8
C2—N2—H2A	125.8	C8—C7—H7	121.8
C8—N2—H2A	125.8	F2—C1—F3	110.5 (7)
N1—C3—C8	107.2 (4)	F2—C1—F1	108.3 (6)
N1—C3—C4	132.5 (4)	F3—C1—F1	105.2 (5)
C8—C3—C4	120.3 (5)	F2—C1—C2	112.0 (5)
C7—C8—N2	132.7 (4)	F3—C1—C2	111.0 (4)
C7—C8—C3	121.9 (4)	F1—C1—C2	109.5 (5)
N2—C8—C3	105.4 (4)	N1—C2—N2	110.3 (4)
C5—C4—C3	117.5 (5)	N1—C2—C1	125.9 (4)
C5—C4—H4	121.2	N2—C2—C1	123.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3i	0.86	1.85	2.707 (5)	173
N1—H1A···O4	0.86	1.88	2.740 (7)	174
O1—H1···O2ii	0.86 (2)	1.86 (6)	2.608 (7)	145 (9)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O3i	0.86	1.85	2.707 (5)	173
N1—H1A⋯O4	0.86	1.88	2.740 (7)	174
O1—H1⋯O2ii	0.86 (2)	1.86 (6)	2.608 (7)	145 (9)

Symmetry codes: (i) ; (ii) .