2-Trifluoro-methyl-1H-benzimidazole.

The asymmetric unit of the title compound, C(8)H(5)F(3)N(2), consists of two half-mol-ecules, one lies on a mirror plane and the other is generated by twofold rotation symmetry, with the axis running through the trifluoro-methyl C atom and the attached benzimidazole C atom. The two 2-trifluoro-methyl-1H-benzimidazole mol-ecules are connected by N-H⋯N hydrogen bonds involving the disordered NH H atoms into chains running parallel to the c axis. One of the trifluoro-methyl groups is disordered over two orientations of equal occupancy.

Related literature

For background to ferroelectric complexes, see: Fu et al. (2011 ▶); Zhang et al. (2010 ▶). For related structures, see: Liu (2011a ▶,b ▶, 2012a ▶,b ▶,c ▶). For graph-set analysis, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C8H5F3N2

M = 186.14

Orthorhombic,

a = 11.859 (2) Å

b = 7.2154 (14) Å

c = 19.508 (4) Å

V = 1669.2 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.14 mm−1

T = 293 K

0.36 × 0.32 × 0.28 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.952, T max = 0.962

13301 measured reflections

1523 independent reflections

983 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.168

S = 1.04

1523 reflections

129 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.23 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: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812017357/go2052sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017357/go2052Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812017357/go2052Isup3.cml

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

C8H5F3N2	F(000) = 752
Mr = 186.14	Dx = 1.481 Mg m−3
Orthorhombic, Pbcm	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2c 2b	θ = 0–25°
a = 11.859 (2) Å	µ = 0.14 mm−1
b = 7.2154 (14) Å	T = 293 K
c = 19.508 (4) Å	Block, colourless
V = 1669.2 (5) Å3	0.36 × 0.32 × 0.28 mm
Z = 8

Rigaku SCXmini diffractometer	1523 independent reflections
Radiation source: fine-focus sealed tube	983 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.074
CCD_Profile_fitting scans	θmax = 25.0°, θmin = 3.3°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −14→14
Tmin = 0.952, Tmax = 0.962	k = −8→8
13301 measured reflections	l = −23→22

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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0577P)2 + 1.2173P] where P = (Fo2 + 2Fc2)/3
1523 reflections	(Δ/σ)max < 0.001
129 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.23 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)
C2	0.2645 (4)	0.2500	0.5000	0.0595 (12)
C1	0.14185 (18)	0.2500	0.5000	0.101 (2)
F1A	0.09271 (18)	0.1770	0.5534	0.157 (4)	0.50
F1B	0.09835 (18)	0.1655	0.4469	0.191 (5)	0.50
F1C	0.10542 (18)	0.4210	0.4964	0.213 (5)	0.50
N1	0.3246 (2)	0.2091 (3)	0.55507 (11)	0.0576 (7)
H1A	0.3000	0.1795	0.5951	0.069*	0.50
C3	0.4353 (2)	0.2242 (4)	0.53443 (14)	0.0495 (7)
C4	0.5347 (3)	0.1964 (5)	0.5697 (2)	0.0760 (11)
H4	0.5350	0.1606	0.6155	0.091*
C5	0.6321 (3)	0.2236 (6)	0.5345 (2)	0.0986 (16)
H5	0.7006	0.2067	0.5568	0.118*
F10A	0.3495 (3)	0.4573 (4)	0.80332 (12)	0.1403 (12)
F10B	0.4734 (4)	0.3146 (6)	0.7500	0.1557 (19)
N4	0.2610 (2)	0.1033 (4)	0.69268 (12)	0.0641 (8)
H4A	0.2749	0.1364	0.6512	0.077*	0.50
C9	0.3662 (6)	0.3519 (8)	0.7500	0.0806 (17)
C10	0.2953 (4)	0.1861 (6)	0.7500	0.0605 (12)
C12	0.1984 (3)	−0.0467 (5)	0.71420 (15)	0.0623 (9)
C13	0.1394 (3)	−0.1800 (6)	0.6772 (2)	0.0855 (12)
H13	0.1382	−0.1800	0.6295	0.103*
C14	0.0830 (4)	−0.3113 (7)	0.7148 (2)	0.1073 (16)
H14	0.0434	−0.4036	0.6917	0.129*

	U11	U22	U33	U12	U13	U23
C2	0.059 (3)	0.076 (3)	0.044 (3)	0.000	0.000	−0.002 (2)
C1	0.066 (4)	0.134 (6)	0.102 (5)	0.000	0.000	0.004 (4)
F1A	0.078 (4)	0.304 (13)	0.088 (5)	−0.044 (9)	0.024 (5)	0.041 (5)
F1B	0.075 (5)	0.376 (17)	0.121 (6)	−0.035 (10)	−0.039 (5)	−0.054 (7)
F1C	0.089 (5)	0.263 (10)	0.288 (12)	0.077 (6)	0.034 (12)	0.078 (11)
N1	0.0703 (17)	0.0672 (18)	0.0354 (13)	−0.0017 (13)	−0.0008 (13)	0.0038 (11)
C3	0.0575 (18)	0.0449 (17)	0.0461 (15)	0.0004 (14)	−0.0057 (14)	−0.0042 (13)
C4	0.082 (3)	0.062 (2)	0.084 (2)	0.0088 (19)	−0.026 (2)	−0.0089 (19)
C5	0.070 (2)	0.068 (3)	0.158 (5)	0.011 (2)	−0.030 (2)	−0.033 (3)
F10A	0.216 (3)	0.113 (2)	0.0923 (18)	−0.069 (2)	0.0224 (18)	−0.0384 (15)
F10B	0.097 (3)	0.117 (3)	0.252 (6)	−0.040 (3)	0.000	0.000
N4	0.081 (2)	0.0755 (19)	0.0357 (13)	−0.0105 (15)	0.0007 (13)	−0.0028 (13)
C9	0.117 (5)	0.082 (4)	0.043 (3)	−0.027 (4)	0.000	0.000
C10	0.076 (3)	0.069 (3)	0.037 (2)	−0.010 (3)	0.000	0.000
C12	0.059 (2)	0.073 (2)	0.0549 (17)	−0.0047 (17)	0.0013 (15)	−0.0026 (16)
C13	0.076 (3)	0.098 (3)	0.083 (3)	−0.012 (2)	−0.001 (2)	−0.025 (2)
C14	0.087 (3)	0.099 (3)	0.135 (4)	−0.030 (2)	−0.005 (2)	−0.022 (3)

C2—N1i	1.323 (3)	C5—H5	0.9300
C2—N1	1.323 (3)	F10A—C9	1.303 (4)
C2—C1	1.454 (5)	F10B—C9	1.300 (7)
C1—F1Ai	1.3052	N4—C10	1.331 (3)
C1—F1A	1.3053	N4—C12	1.378 (4)
C1—F1B	1.3079	N4—H4A	0.8600
C1—F1Bi	1.3079	C9—F10Aii	1.304 (4)
C1—F1Ci	1.3095	C9—C10	1.462 (7)
C1—F1C	1.3095	C10—N4ii	1.331 (3)
N1—C3	1.377 (4)	C12—C13	1.392 (5)
N1—H1A	0.8600	C12—C12ii	1.397 (6)
C3—C4	1.380 (4)	C13—C14	1.372 (6)
C3—C3i	1.394 (5)	C13—H13	0.9300
C4—C5	1.359 (5)	C14—C14ii	1.375 (9)
C4—H4	0.9300	C14—H14	0.9300
C5—C5i	1.399 (9)
N1i—C2—N1	114.7 (4)	C4—C5—C5i	121.8 (2)
N1i—C2—C1	122.6 (2)	C4—C5—H5	119.1
N1—C2—C1	122.6 (2)	C5i—C5—H5	119.1
F1A—C1—F1B	105.6	C10—N4—C12	105.1 (3)
F1Ai—C1—F1Bi	105.6	C10—N4—H4A	127.4
F1Ai—C1—F1Ci	106.0	C12—N4—H4A	127.4
F1Bi—C1—F1Ci	105.4	F10B—C9—F10A	105.6 (4)
F1A—C1—F1C	106.0	F10B—C9—F10Aii	105.6 (4)
F1B—C1—F1C	105.4	F10A—C9—F10Aii	105.9 (5)
F1Ai—C1—C2	116.522 (6)	F10B—C9—C10	113.1 (5)
F1A—C1—C2	116.519 (5)	F10A—C9—C10	113.0 (3)
F1B—C1—C2	113.229 (5)	F10Aii—C9—C10	113.0 (3)
F1Bi—C1—C2	113.230 (5)	N4—C10—N4ii	114.3 (4)
F1Ci—C1—C2	109.263 (5)	N4—C10—C9	122.9 (2)
F1C—C1—C2	109.262 (5)	N4ii—C10—C9	122.9 (2)
C2—N1—C3	105.0 (3)	N4—C12—C13	131.0 (3)
C2—N1—H1A	127.5	N4—C12—C12ii	107.74 (16)
C3—N1—H1A	127.5	C13—C12—C12ii	121.3 (2)
N1—C3—C4	131.0 (3)	C14—C13—C12	116.4 (4)
N1—C3—C3i	107.64 (15)	C14—C13—H13	121.8
C4—C3—C3i	121.3 (2)	C12—C13—H13	121.8
C5—C4—C3	116.9 (4)	C13—C14—C14ii	122.3 (2)
C5—C4—H4	121.5	C13—C14—H14	118.9
C3—C4—H4	121.5	C14ii—C14—H14	118.9
N1i—C2—C1—F1Ai	−11.43 (13)	N1—C3—C4—C5	−179.7 (3)
N1—C2—C1—F1Ai	168.57 (13)	C3i—C3—C4—C5	0.7 (5)
N1i—C2—C1—F1A	168.57 (13)	C3—C4—C5—C5i	−0.4 (7)
N1—C2—C1—F1A	−11.43 (13)	C12—N4—C10—N4ii	0.2 (5)
N1i—C2—C1—F1B	45.84 (13)	C12—N4—C10—C9	179.2 (5)
N1—C2—C1—F1B	−134.16 (13)	F10B—C9—C10—N4	−89.5 (4)
N1i—C2—C1—F1Bi	−134.16 (13)	F10A—C9—C10—N4	150.6 (4)
N1—C2—C1—F1Bi	45.84 (13)	F10Aii—C9—C10—N4	30.4 (8)
N1i—C2—C1—F1Ci	108.66 (13)	F10B—C9—C10—N4ii	89.5 (4)
N1—C2—C1—F1Ci	−71.34 (13)	F10A—C9—C10—N4ii	−30.4 (8)
N1i—C2—C1—F1C	−71.34 (13)	F10Aii—C9—C10—N4ii	−150.6 (4)
N1—C2—C1—F1C	108.66 (13)	C10—N4—C12—C13	178.1 (4)
N1i—C2—N1—C3	−0.07 (14)	C10—N4—C12—C12ii	−0.1 (3)
C1—C2—N1—C3	179.93 (14)	N4—C12—C13—C14	−178.8 (4)
C2—N1—C3—C4	−179.4 (3)	C12ii—C12—C13—C14	−0.8 (4)
C2—N1—C3—C3i	0.2 (3)	C12—C13—C14—C14ii	0.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N4	0.86	2.03	2.891 (3)	173
N4—H4A···N1	0.86	2.03	2.891 (3)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N4	0.86	2.03	2.891 (3)	173
N4—H4A⋯N1	0.86	2.03	2.891 (3)	174