2-[4-(Tri-fluoro-meth-yl)phen-yl]-1H-benzimidazole.

In the title compound, C14H9F3N2, the mean planes of the benzimidazole ring system and the tri-fluoro-methyl-substituted benzene ring form a dihedral angle of 30.1 (1)°. In the crystal, mol-ecules are linked by N-H⋯N hydrogen bonds into chains along [010]. Weak C-H⋯F hydrogen bonds and a weak C-H⋯π inter-action connect the chains into a two-dimensional network parallel to (001).

Related literature

For therapeutic and medicinal properties of benzimidazole derivatives, see: Ozden et al. (2004 ▶); Easman et al. (2001 ▶); Thakurdesai et al. (2007 ▶); Ansari & Lal (2009 ▶). For the bioactivity of fluorine-containing compounds, see: Ulrich (2004 ▶). For related structures, see: Jian et al. (2006 ▶); Rosepriya et al. (2011 ▶); Fathima et al. (2013 ▶); Krishnamurthy et al. (2013 ▶); Rashid et al. (2007 ▶).

Experimental

Crystal data

C14H9F3N2

M = 262.23

Orthorhombic,

a = 9.2292 (9) Å

b = 9.8117 (10) Å

c = 25.347 (2) Å

V = 2295.2 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.13 mm−1

T = 296 K

0.18 × 0.16 × 0.16 mm

Data collection

Bruker SMART APEX CCD detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.978, T max = 0.980

13079 measured reflections

2501 independent reflections

1671 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.159

S = 0.90

2501 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.33 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and CAMERON (Watkin et al., 1996 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814012963/lh5706sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814012963/lh5706Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814012963/lh5706Isup3.cml

CCDC reference: 1006709

Additional supporting information: crystallographic information; 3D view; checkCIF report

C14H9F3N2	F(000) = 1072
Mr = 262.23	Dx = 1.518 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1671 reflections
a = 9.2292 (9) Å	θ = 2.7–27.0°
b = 9.8117 (10) Å	µ = 0.13 mm−1
c = 25.347 (2) Å	T = 296 K
V = 2295.2 (4) Å3	Block, yellow
Z = 8	0.18 × 0.16 × 0.16 mm

Bruker SMART APEX CCD detector diffractometer	2501 independent reflections
Radiation source: fine-focus sealed tube	1671 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.070
ω scans	θmax = 27.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −11→11
Tmin = 0.978, Tmax = 0.980	k = −12→12
13079 measured reflections	l = −32→23

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H-atom parameters constrained
S = 0.90	w = 1/[σ2(Fo2) + (0.0847P)2 + 2.1194P] where P = (Fo2 + 2Fc2)/3
2501 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
N1	0.7803 (2)	0.34060 (19)	−0.15282 (8)	0.0231 (5)
H1	0.7333	0.2656	−0.1490	0.028*
N2	0.8319 (2)	0.56324 (19)	−0.14790 (8)	0.0226 (5)
F1	0.13831 (19)	0.43903 (16)	−0.01444 (8)	0.0575 (6)
F2	0.09362 (17)	0.6088 (2)	−0.06475 (7)	0.0547 (6)
F3	0.20033 (18)	0.63865 (18)	0.00860 (7)	0.0495 (5)
C1	1.0744 (3)	0.5460 (3)	−0.19449 (10)	0.0266 (6)
H1A	1.0979	0.6380	−0.1922	0.032*
C2	1.1659 (3)	0.4549 (3)	−0.21894 (10)	0.0282 (6)
H2	1.2515	0.4866	−0.2339	0.034*
C3	1.1332 (3)	0.3152 (2)	−0.22181 (9)	0.0271 (6)
H3	1.1975	0.2567	−0.2387	0.033*
C4	1.0077 (3)	0.2629 (2)	−0.20016 (9)	0.0251 (5)
H4	0.9867	0.1703	−0.2014	0.030*
C5	0.9137 (2)	0.3561 (2)	−0.17622 (9)	0.0221 (5)
C6	0.9454 (2)	0.4960 (2)	−0.17332 (9)	0.0225 (5)
C7	0.7369 (2)	0.4661 (2)	−0.13685 (9)	0.0220 (5)
C8	0.5975 (2)	0.4891 (2)	−0.11017 (9)	0.0229 (5)
C9	0.4787 (3)	0.4059 (3)	−0.12079 (10)	0.0303 (6)
H9	0.4874	0.3348	−0.1449	0.036*
C10	0.3482 (3)	0.4286 (3)	−0.09573 (11)	0.0316 (6)
H10	0.2691	0.3729	−0.1029	0.038*
C11	0.3353 (3)	0.5344 (2)	−0.05983 (10)	0.0261 (6)
C12	0.4518 (3)	0.6180 (2)	−0.04903 (9)	0.0274 (6)
H12	0.4422	0.6892	−0.0251	0.033*
C13	0.5836 (3)	0.5953 (2)	−0.07410 (9)	0.0252 (5)
H13	0.6625	0.6512	−0.0668	0.030*
C14	0.1920 (3)	0.5553 (3)	−0.03327 (10)	0.0292 (6)

	U11	U22	U33	U12	U13	U23
N1	0.0221 (10)	0.0181 (10)	0.0291 (11)	−0.0002 (8)	0.0020 (8)	0.0001 (8)
N2	0.0218 (10)	0.0200 (10)	0.0261 (11)	−0.0003 (8)	0.0011 (8)	−0.0008 (8)
F1	0.0508 (11)	0.0331 (10)	0.0887 (15)	−0.0011 (8)	0.0391 (10)	0.0039 (9)
F2	0.0301 (9)	0.0918 (15)	0.0422 (10)	0.0208 (9)	0.0039 (7)	0.0117 (9)
F3	0.0369 (10)	0.0623 (12)	0.0493 (10)	−0.0021 (8)	0.0102 (7)	−0.0253 (8)
C1	0.0237 (12)	0.0237 (13)	0.0325 (14)	−0.0018 (10)	0.0010 (10)	0.0015 (10)
C2	0.0226 (12)	0.0305 (14)	0.0315 (14)	−0.0013 (10)	0.0050 (10)	0.0051 (11)
C3	0.0264 (13)	0.0268 (13)	0.0283 (13)	0.0057 (10)	0.0013 (10)	−0.0019 (10)
C4	0.0268 (12)	0.0210 (12)	0.0275 (13)	0.0021 (10)	−0.0014 (10)	0.0004 (9)
C5	0.0204 (12)	0.0231 (12)	0.0228 (12)	0.0015 (9)	−0.0018 (9)	0.0009 (9)
C6	0.0220 (12)	0.0224 (12)	0.0230 (12)	0.0036 (9)	−0.0025 (9)	0.0005 (9)
C7	0.0215 (12)	0.0220 (12)	0.0226 (12)	0.0017 (9)	−0.0037 (10)	−0.0015 (9)
C8	0.0219 (12)	0.0220 (12)	0.0248 (12)	0.0015 (9)	−0.0009 (9)	0.0023 (9)
C9	0.0265 (13)	0.0255 (13)	0.0390 (15)	−0.0012 (10)	0.0022 (11)	−0.0092 (10)
C10	0.0248 (13)	0.0322 (15)	0.0378 (15)	−0.0050 (11)	0.0007 (11)	−0.0071 (11)
C11	0.0248 (13)	0.0253 (13)	0.0282 (13)	0.0026 (10)	0.0021 (10)	0.0007 (10)
C12	0.0306 (13)	0.0235 (13)	0.0282 (13)	0.0012 (10)	0.0028 (10)	−0.0051 (9)
C13	0.0255 (12)	0.0226 (12)	0.0274 (13)	−0.0024 (10)	−0.0006 (10)	−0.0014 (9)
C14	0.0299 (13)	0.0246 (13)	0.0332 (14)	0.0015 (10)	0.0017 (11)	−0.0005 (10)

N1—C7	1.357 (3)	C4—C5	1.399 (3)
N1—C5	1.375 (3)	C4—H4	0.9300
N1—H1	0.8600	C5—C6	1.406 (3)
N2—C7	1.325 (3)	C7—C8	1.471 (3)
N2—C6	1.395 (3)	C8—C13	1.393 (3)
F1—C14	1.332 (3)	C8—C9	1.393 (3)
F2—C14	1.318 (3)	C9—C10	1.379 (4)
F3—C14	1.342 (3)	C9—H9	0.9300
C1—C2	1.377 (3)	C10—C11	1.386 (3)
C1—C6	1.395 (3)	C10—H10	0.9300
C1—H1A	0.9300	C11—C12	1.380 (3)
C2—C3	1.405 (4)	C11—C14	1.498 (3)
C2—H2	0.9300	C12—C13	1.391 (3)
C3—C4	1.380 (3)	C12—H12	0.9300
C3—H3	0.9300	C13—H13	0.9300
C7—N1—C5	107.02 (19)	C13—C8—C9	119.5 (2)
C7—N1—H1	126.5	C13—C8—C7	119.8 (2)
C5—N1—H1	126.5	C9—C8—C7	120.7 (2)
C7—N2—C6	104.73 (18)	C10—C9—C8	120.2 (2)
C2—C1—C6	117.9 (2)	C10—C9—H9	119.9
C2—C1—H1A	121.0	C8—C9—H9	119.9
C6—C1—H1A	121.0	C9—C10—C11	119.9 (2)
C1—C2—C3	121.7 (2)	C9—C10—H10	120.1
C1—C2—H2	119.2	C11—C10—H10	120.1
C3—C2—H2	119.2	C12—C11—C10	120.6 (2)
C4—C3—C2	121.5 (2)	C12—C11—C14	121.2 (2)
C4—C3—H3	119.3	C10—C11—C14	118.3 (2)
C2—C3—H3	119.3	C11—C12—C13	119.8 (2)
C3—C4—C5	116.7 (2)	C11—C12—H12	120.1
C3—C4—H4	121.6	C13—C12—H12	120.1
C5—C4—H4	121.6	C12—C13—C8	120.0 (2)
N1—C5—C4	132.1 (2)	C12—C13—H13	120.0
N1—C5—C6	105.74 (19)	C8—C13—H13	120.0
C4—C5—C6	122.2 (2)	F2—C14—F1	107.5 (2)
N2—C6—C1	130.7 (2)	F2—C14—F3	106.0 (2)
N2—C6—C5	109.3 (2)	F1—C14—F3	105.1 (2)
C1—C6—C5	120.0 (2)	F2—C14—C11	113.0 (2)
N2—C7—N1	113.2 (2)	F1—C14—C11	111.8 (2)
N2—C7—C8	124.5 (2)	F3—C14—C11	112.9 (2)
N1—C7—C8	122.3 (2)
C6—C1—C2—C3	−1.3 (4)	N1—C7—C8—C13	150.3 (2)
C1—C2—C3—C4	−0.1 (4)	N2—C7—C8—C9	149.8 (2)
C2—C3—C4—C5	1.2 (3)	N1—C7—C8—C9	−30.0 (3)
C7—N1—C5—C4	−179.0 (2)	C13—C8—C9—C10	−0.1 (4)
C7—N1—C5—C6	−0.3 (2)	C7—C8—C9—C10	−179.7 (2)
C3—C4—C5—N1	177.6 (2)	C8—C9—C10—C11	0.0 (4)
C3—C4—C5—C6	−1.0 (3)	C9—C10—C11—C12	0.3 (4)
C7—N2—C6—C1	179.2 (2)	C9—C10—C11—C14	−179.7 (2)
C7—N2—C6—C5	−0.6 (2)	C10—C11—C12—C13	−0.4 (4)
C2—C1—C6—N2	−178.2 (2)	C14—C11—C12—C13	179.6 (2)
C2—C1—C6—C5	1.5 (3)	C11—C12—C13—C8	0.3 (4)
N1—C5—C6—N2	0.5 (2)	C9—C8—C13—C12	−0.1 (4)
C4—C5—C6—N2	179.4 (2)	C7—C8—C13—C12	179.6 (2)
N1—C5—C6—C1	−179.2 (2)	C12—C11—C14—F2	106.1 (3)
C4—C5—C6—C1	−0.3 (3)	C10—C11—C14—F2	−73.9 (3)
C6—N2—C7—N1	0.4 (3)	C12—C11—C14—F1	−132.4 (3)
C6—N2—C7—C8	−179.4 (2)	C10—C11—C14—F1	47.6 (3)
C5—N1—C7—N2	−0.1 (3)	C12—C11—C14—F3	−14.1 (3)
C5—N1—C7—C8	179.7 (2)	C10—C11—C14—F3	165.8 (2)
N2—C7—C8—C13	−29.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2i	0.86	2.07	2.914 (3)	165
C12—H12···F1ii	0.93	2.57	3.374 (3)	144
C13—H13···F3iii	0.93	2.55	3.275 (4)	134
C2—H2···Cgiv	0.93	2.94	3.700 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the N1/C5/C6/N2/C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2i	0.86	2.07	2.914 (3)	165
C12—H12⋯F1ii	0.93	2.57	3.374 (3)	144
C13—H13⋯F3iii	0.93	2.55	3.275 (4)	134
C2—H2⋯Cg iv	0.93	2.94	3.700 (3)	140

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