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

Ihe title salt, C(8)H(6)F(3)N(2) (+)·NO(3) (-), the F atoms of the triflouromethyl group are disordered over two sets of sites in a 0.58 (2):0.42 (2) ratio. In the crystal, N-H⋯O hydrogen bonds link the cations and anions into chains running parallel to the b axis. There is π-π stacking between symmetry-related benzene rings with a centroid-centroid distance of 3.949 (3) Å. The crystal studied was a non-merohedral twin, with a 19% minor component.

Related literature

The title compound was synthesized as part of a search for potential ferroelectric compouns. For background to ferroelectric complexes, see: Fu et al. (2011 ▶); Zhang et al. (2010 ▶). For related structures, see: Liu (2011a ▶,b ▶, 2012 ▶). For the separation of the non-merohedrally twinned diffraction data, see: Spek (2009 ▶).

Experimental

Crystal data

C8H6F3N2 +·NO3 −

M = 249.16

Triclinic,

a = 7.2745 (15) Å

b = 9.0962 (18) Å

c = 9.4502 (19) Å

α = 61.53 (3)°

β = 71.18 (3)°

γ = 82.41 (3)°

V = 520.1 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.16 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.969, T max = 0.969

1828 measured reflections

1828 independent reflections

910 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.227

S = 1.01

1828 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.27 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: PLATON (Spek, 2009) ▶; software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812009415/go2046sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009415/go2046Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812009415/go2046Isup3.cml

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

C8H6F3N2+·NO3−	V = 520.1 (3) Å3
Mr = 249.16	Z = 2
Triclinic, P1	F(000) = 252
Hall symbol: -P 1	Dx = 1.591 Mg m−3
a = 7.2745 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.0962 (18) Å	θ = 3.3–25.0°
c = 9.4502 (19) Å	µ = 0.16 mm−1
α = 61.53 (3)°	T = 293 K
β = 71.18 (3)°	Block, colourless
γ = 82.41 (3)°	0.20 × 0.20 × 0.20 mm

Rigaku SCXmini diffractometer	1828 independent reflections
Radiation source: fine-focus sealed tube	910 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
CCD_Profile_fitting scans	θmax = 25.0°, θmin = 3.3°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −8→8
Tmin = 0.969, Tmax = 0.969	k = −10→10
1828 measured reflections	l = −9→11

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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.227	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.1061P)2] where P = (Fo2 + 2Fc2)/3
1828 reflections	(Δ/σ)max < 0.001
183 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.27 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 > 2sigma(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	Occ. (<1)
N2	0.2477 (5)	0.3645 (4)	0.4631 (4)	0.0551 (10)
H2A	0.2479	0.4361	0.4981	0.066*
O2	0.2968 (6)	0.7956 (4)	0.5882 (4)	0.0824 (12)
O1	0.2843 (6)	0.5588 (4)	0.5979 (5)	0.0849 (12)
N3	0.2467 (5)	0.1269 (4)	0.4602 (4)	0.0541 (10)
H3A	0.2470	0.0209	0.4932	0.065*
N1	0.2547 (6)	0.7095 (5)	0.5303 (5)	0.0586 (11)
O3	0.1883 (5)	0.7778 (5)	0.4106 (5)	0.0839 (12)
F1	0.343 (3)	−0.0238 (12)	0.7647 (14)	0.104 (7)	0.58 (2)
F2	0.331 (4)	0.1984 (11)	0.7662 (17)	0.108 (7)	0.58 (2)
F3	0.0708 (17)	0.077 (4)	0.8311 (11)	0.166 (11)	0.58 (2)
F1'	0.396 (2)	0.077 (7)	0.7605 (16)	0.187 (17)	0.42 (2)
F2'	0.144 (5)	0.1946 (18)	0.8128 (15)	0.110 (8)	0.42 (2)
F3'	0.132 (4)	−0.0270 (19)	0.8115 (17)	0.107 (8)	0.42 (2)
C2	0.2467 (6)	0.2011 (5)	0.5524 (6)	0.0531 (12)
C3	0.2462 (7)	0.2518 (5)	0.3017 (5)	0.0523 (12)
C8	0.2483 (6)	0.4019 (5)	0.3024 (5)	0.0520 (12)
C7	0.2462 (7)	0.5527 (6)	0.1610 (6)	0.0681 (14)
H7	0.2462	0.6545	0.1619	0.082*
C5	0.2441 (8)	0.3936 (8)	0.0199 (6)	0.0781 (16)
H5	0.2447	0.3947	−0.0791	0.094*
C6	0.2442 (8)	0.5454 (7)	0.0225 (7)	0.0778 (16)
H6	0.2428	0.6445	−0.0741	0.093*
C1	0.2396 (12)	0.1092 (7)	0.7352 (7)	0.0659 (14)
C4	0.2431 (8)	0.2420 (7)	0.1588 (6)	0.0698 (15)
H4	0.2405	0.1405	0.1580	0.084*

	U11	U22	U33	U12	U13	U23
N2	0.073 (3)	0.041 (2)	0.063 (2)	0.0001 (18)	−0.026 (2)	−0.029 (2)
O2	0.130 (3)	0.050 (2)	0.090 (3)	0.009 (2)	−0.050 (2)	−0.041 (2)
O1	0.140 (3)	0.042 (2)	0.093 (3)	0.010 (2)	−0.050 (2)	−0.0389 (19)
N3	0.071 (3)	0.038 (2)	0.060 (2)	−0.0001 (17)	−0.019 (2)	−0.0276 (19)
N1	0.071 (3)	0.051 (3)	0.060 (3)	−0.005 (2)	−0.015 (2)	−0.031 (2)
O3	0.097 (3)	0.085 (3)	0.081 (3)	0.003 (2)	−0.045 (2)	−0.036 (2)
F1	0.20 (2)	0.049 (5)	0.082 (5)	0.045 (7)	−0.079 (9)	−0.028 (4)
F2	0.21 (2)	0.068 (5)	0.084 (6)	−0.002 (6)	−0.088 (10)	−0.037 (4)
F3	0.094 (7)	0.26 (3)	0.055 (5)	−0.013 (14)	0.003 (5)	−0.021 (12)
F1'	0.094 (11)	0.33 (4)	0.063 (7)	0.00 (2)	−0.033 (7)	−0.02 (2)
F2'	0.19 (3)	0.076 (8)	0.065 (7)	0.019 (9)	−0.025 (10)	−0.044 (6)
F3'	0.18 (2)	0.066 (7)	0.063 (7)	−0.045 (9)	−0.021 (9)	−0.015 (5)
C2	0.063 (3)	0.041 (3)	0.060 (3)	0.003 (2)	−0.022 (2)	−0.025 (2)
C3	0.065 (3)	0.043 (3)	0.054 (3)	0.003 (2)	−0.024 (2)	−0.023 (2)
C8	0.058 (3)	0.048 (3)	0.055 (3)	0.001 (2)	−0.022 (2)	−0.025 (2)
C7	0.079 (4)	0.052 (3)	0.071 (3)	0.000 (2)	−0.025 (3)	−0.024 (3)
C5	0.087 (4)	0.093 (4)	0.051 (3)	0.005 (3)	−0.026 (3)	−0.028 (3)
C6	0.104 (5)	0.059 (3)	0.066 (3)	0.000 (3)	−0.040 (3)	−0.016 (3)
C1	0.093 (5)	0.053 (4)	0.059 (4)	0.003 (3)	−0.028 (4)	−0.029 (3)
C4	0.082 (4)	0.075 (4)	0.068 (3)	0.002 (3)	−0.025 (3)	−0.044 (3)

N2—C2	1.314 (5)	F2'—C1	1.303 (13)
N2—C8	1.388 (5)	F3'—C1	1.309 (15)
N2—H2A	0.8600	C2—C1	1.504 (6)
O2—N1	1.260 (4)	C3—C8	1.371 (6)
O1—N1	1.228 (5)	C3—C4	1.402 (6)
N3—C2	1.333 (5)	C8—C7	1.388 (6)
N3—C3	1.384 (5)	C7—C6	1.346 (7)
N3—H3A	0.8600	C7—H7	0.9300
N1—O3	1.226 (5)	C5—C4	1.377 (7)
F1—C1	1.295 (12)	C5—C6	1.393 (8)
F2—C1	1.297 (12)	C5—H5	0.9300
F3—C1	1.240 (10)	C6—H6	0.9300
F1'—C1	1.206 (14)	C4—H4	0.9300
C2—N2—C8	108.3 (3)	C5—C6—H6	119.1
C2—N2—H2A	125.9	F1'—C1—F3	132.5 (9)
C8—N2—H2A	125.9	F1'—C1—F1	48 (2)
C2—N3—C3	107.4 (3)	F3—C1—F1	112.0 (13)
C2—N3—H3A	126.3	F1'—C1—F2	55 (2)
C3—N3—H3A	126.3	F3—C1—F2	110.2 (11)
O3—N1—O1	123.2 (4)	F1—C1—F2	102.3 (10)
O3—N1—O2	119.6 (4)	F1'—C1—F2'	108.7 (16)
O1—N1—O2	117.2 (4)	F3—C1—F2'	54.6 (9)
N2—C2—N3	110.6 (4)	F1—C1—F2'	139.1 (9)
N2—C2—C1	125.0 (4)	F2—C1—F2'	59.5 (9)
N3—C2—C1	124.3 (4)	F1'—C1—F3'	110.3 (19)
C8—C3—N3	107.3 (4)	F3—C1—F3'	49.3 (11)
C8—C3—C4	122.1 (4)	F1—C1—F3'	67.9 (9)
N3—C3—C4	130.6 (4)	F2—C1—F3'	141.3 (8)
C3—C8—N2	106.5 (4)	F2'—C1—F3'	102.4 (12)
C3—C8—C7	121.4 (4)	F1'—C1—C2	115.1 (8)
N2—C8—C7	132.1 (4)	F3—C1—C2	112.3 (7)
C6—C7—C8	117.2 (5)	F1—C1—C2	110.6 (6)
C6—C7—H7	121.4	F2—C1—C2	108.9 (6)
C8—C7—H7	121.4	F2'—C1—C2	110.0 (7)
C4—C5—C6	122.3 (5)	F3'—C1—C2	109.6 (7)
C4—C5—H5	118.9	C5—C4—C3	115.1 (5)
C6—C5—H5	118.9	C5—C4—H4	122.4
C7—C6—C5	121.8 (5)	C3—C4—H4	122.4
C7—C6—H6	119.1
C8—N2—C2—N3	0.0 (5)	N2—C2—C1—F1'	−92 (3)
C8—N2—C2—C1	−178.0 (5)	N3—C2—C1—F1'	90 (3)
C3—N3—C2—N2	−0.5 (5)	N2—C2—C1—F3	90 (2)
C3—N3—C2—C1	177.6 (5)	N3—C2—C1—F3	−88 (2)
C2—N3—C3—C8	0.7 (5)	N2—C2—C1—F1	−144.3 (11)
C2—N3—C3—C4	−178.9 (5)	N3—C2—C1—F1	38.0 (13)
N3—C3—C8—N2	−0.7 (5)	N2—C2—C1—F2	−32.6 (16)
C4—C3—C8—N2	179.0 (4)	N3—C2—C1—F2	149.7 (13)
N3—C3—C8—C7	−179.3 (4)	N2—C2—C1—F2'	31 (2)
C4—C3—C8—C7	0.4 (7)	N3—C2—C1—F2'	−146.9 (18)
C2—N2—C8—C3	0.4 (5)	N2—C2—C1—F3'	142.8 (16)
C2—N2—C8—C7	178.8 (5)	N3—C2—C1—F3'	−35.0 (17)
C3—C8—C7—C6	−0.7 (8)	C6—C5—C4—C3	−1.2 (8)
N2—C8—C7—C6	−178.8 (5)	C8—C3—C4—C5	0.5 (7)
C8—C7—C6—C5	0.0 (8)	N3—C3—C4—C5	−179.8 (5)
C4—C5—C6—C7	1.0 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.86	2.703 (5)	168
N3—H3A···O2i	0.86	1.84	2.682 (5)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.86	1.86	2.703 (5)	168
N3—H3A⋯O2i	0.86	1.84	2.682 (5)	165

Symmetry code: (i) .