1-Phenyl-2-[4-(trifluoro-meth-yl)phen-yl]-1H-benzimidazole.

In the title mol-ecule, C(20)H(13)F(3)N(2), the benzimidazole unit is close to being planar [maximum deviation = 0.012 (1) Å] and forms dihedral angles of 31.43 (7) and 61.45 (9)° with the 4-(trifluoromethyl)phenyl and 1-phenyl rings, respectively; the dihedral angle between these rings is 60.94 (10)°. In the crystal, C-H⋯F hydrogen bonds link the mol-ecules into chains along the c-axis direction. The CF(3) group is rotationally disordered with an occupancy ratio of 0.557 (8):0.443 (8) for the F atoms.

Related literature

For the properties of related compounds, see: Bu et al. (1996 ▶); Cross et al. (1995 ▶); Fu et al. (2011 ▶); Zhang et al. (2010 ▶). For bond lengths and angles in related structures, see: Yoon et al. (2011 ▶); Kassim et al. (2012 ▶).

Experimental

Crystal data

C20H13F3N2

M = 338.32

Triclinic,

a = 8.7179 (4) Å

b = 9.6796 (5) Å

c = 11.3612 (6) Å

α = 67.654 (2)°

β = 68.123 (2)°

γ = 85.013 (2)°

V = 821.20 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker,2008 ▶) T min = 0.960, T max = 0.986

16592 measured reflections

2889 independent reflections

2338 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.105

S = 1.03

2889 reflections

255 parameters

36 restraints

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: APEX2 and SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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: PLATON.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813000834/bv2218sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000834/bv2218Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813000834/bv2218Isup3.cml

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

C20H13F3N2	Z = 2
Mr = 338.32	F(000) = 348
Triclinic, P1	Dx = 1.368 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7179 (4) Å	Cell parameters from 7057 reflections
b = 9.6796 (5) Å	θ = 2.3–27.1°
c = 11.3612 (6) Å	µ = 0.11 mm−1
α = 67.654 (2)°	T = 293 K
β = 68.123 (2)°	Block, colourless
γ = 85.013 (2)°	0.30 × 0.20 × 0.20 mm
V = 821.20 (7) Å3

Bruker Kappa APEXII diffractometer	2889 independent reflections
Radiation source: fine focus sealed tube	2338 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 18.4 pixels mm-1	θmax = 25.0°, θmin = 2.3°
ω and φ scan	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker,2008)	k = −11→11
Tmin = 0.960, Tmax = 0.986	l = −13→13
16592 measured reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0469P)2 + 0.1406P] where P = (Fo2 + 2Fc2)/3
2889 reflections	(Δ/σ)max = 0.001
255 parameters	Δρmax = 0.15 e Å−3
36 restraints	Δρmin = −0.14 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	Occ. (<1)
C1	−0.1427 (3)	0.2068 (3)	1.5614 (2)	0.0834 (5)
C2	−0.04295 (19)	0.28680 (17)	1.41364 (16)	0.0618 (4)
C3	0.0815 (2)	0.39161 (19)	1.37506 (17)	0.0672 (4)
H3	0.1005	0.4140	1.4414	0.081*
C4	0.17792 (19)	0.46346 (18)	1.23902 (17)	0.0614 (4)
H4	0.2612	0.5346	1.2139	0.074*
C5	0.15171 (17)	0.43049 (15)	1.13943 (15)	0.0523 (4)
C6	0.02360 (19)	0.32742 (17)	1.17905 (16)	0.0590 (4)
H6	0.0027	0.3061	1.1130	0.071*
C7	−0.0730 (2)	0.25634 (18)	1.31517 (17)	0.0635 (4)
H7	−0.1587	0.1876	1.3406	0.076*
C8	0.25824 (17)	0.51116 (15)	0.99601 (15)	0.0524 (4)
C9	0.40857 (19)	0.68454 (16)	0.81207 (16)	0.0575 (4)
C10	0.4994 (2)	0.81574 (18)	0.71278 (18)	0.0711 (5)
H10	0.5086	0.8970	0.7349	0.085*
C11	0.5744 (2)	0.8215 (2)	0.58197 (19)	0.0782 (5)
H11	0.6351	0.9086	0.5140	0.094*
C12	0.5625 (2)	0.7008 (2)	0.54771 (18)	0.0774 (5)
H12	0.6156	0.7090	0.4573	0.093*
C13	0.4747 (2)	0.56999 (19)	0.64349 (17)	0.0682 (5)
H13	0.4676	0.4887	0.6207	0.082*
C14	0.39737 (18)	0.56482 (16)	0.77574 (15)	0.0549 (4)
C15	0.27055 (17)	0.30532 (15)	0.90658 (15)	0.0539 (4)
C16	0.1858 (2)	0.28353 (19)	0.83389 (17)	0.0663 (4)
H16	0.1456	0.3645	0.7795	0.080*
C17	0.1609 (2)	0.1411 (2)	0.8421 (2)	0.0855 (6)
H17	0.1055	0.1259	0.7918	0.103*
C18	0.2174 (3)	0.0223 (2)	0.9239 (3)	0.0940 (7)
H18	0.1999	−0.0738	0.9296	0.113*
C19	0.2999 (2)	0.0440 (2)	0.9977 (2)	0.0926 (7)
H19	0.3362	−0.0377	1.0547	0.111*
C20	0.3294 (2)	0.18642 (18)	0.9882 (2)	0.0743 (5)
H20	0.3882	0.2016	1.0363	0.089*
N1	0.32109 (16)	0.64829 (13)	0.95021 (13)	0.0604 (4)
N2	0.29987 (15)	0.45366 (12)	0.89494 (12)	0.0530 (3)
F1	−0.2223 (12)	0.0892 (8)	1.5887 (4)	0.142 (3)	0.557 (8)
F2	−0.2557 (8)	0.2984 (5)	1.6041 (5)	0.1329 (18)	0.557 (8)
F3	−0.0570 (6)	0.1792 (13)	1.6361 (4)	0.160 (3)	0.557 (8)
F1'	−0.2976 (8)	0.1695 (15)	1.5888 (7)	0.155 (4)	0.443 (8)
F2'	−0.1517 (17)	0.2719 (7)	1.6418 (4)	0.140 (3)	0.443 (8)
F3'	−0.0821 (14)	0.0771 (8)	1.6144 (5)	0.160 (3)	0.443 (8)

	U11	U22	U33	U12	U13	U23
F1	0.203 (7)	0.116 (3)	0.0732 (19)	−0.092 (4)	−0.010 (3)	−0.018 (3)
F2	0.122 (3)	0.158 (4)	0.084 (2)	0.009 (3)	0.007 (2)	−0.053 (2)
F3	0.141 (3)	0.231 (7)	0.069 (2)	−0.037 (4)	−0.056 (2)	0.013 (4)
N1	0.0698 (8)	0.0499 (7)	0.0627 (8)	0.0024 (6)	−0.0207 (6)	−0.0258 (6)
N2	0.0609 (7)	0.0454 (7)	0.0545 (7)	0.0035 (5)	−0.0201 (6)	−0.0220 (6)
C1	0.0916 (14)	0.0895 (15)	0.0642 (12)	−0.0089 (12)	−0.0223 (11)	−0.0268 (11)
C2	0.0670 (10)	0.0589 (9)	0.0589 (10)	0.0050 (7)	−0.0227 (8)	−0.0224 (8)
C3	0.0728 (10)	0.0776 (11)	0.0603 (10)	0.0032 (8)	−0.0255 (8)	−0.0340 (9)
C4	0.0620 (9)	0.0639 (9)	0.0656 (10)	−0.0008 (7)	−0.0222 (8)	−0.0321 (8)
C5	0.0559 (8)	0.0482 (8)	0.0580 (9)	0.0100 (6)	−0.0232 (7)	−0.0247 (7)
C6	0.0647 (9)	0.0606 (9)	0.0600 (9)	0.0036 (7)	−0.0265 (8)	−0.0278 (8)
C7	0.0651 (9)	0.0593 (9)	0.0648 (10)	−0.0033 (7)	−0.0218 (8)	−0.0227 (8)
C8	0.0570 (8)	0.0473 (8)	0.0590 (9)	0.0084 (6)	−0.0240 (7)	−0.0248 (7)
C9	0.0622 (9)	0.0488 (8)	0.0607 (9)	0.0044 (7)	−0.0212 (7)	−0.0215 (7)
C10	0.0803 (11)	0.0526 (9)	0.0746 (12)	−0.0029 (8)	−0.0221 (9)	−0.0227 (8)
C11	0.0835 (12)	0.0625 (10)	0.0695 (12)	−0.0103 (9)	−0.0175 (9)	−0.0122 (9)
C12	0.0835 (12)	0.0795 (12)	0.0583 (10)	−0.0090 (10)	−0.0138 (9)	−0.0236 (9)
C13	0.0758 (10)	0.0674 (10)	0.0616 (10)	−0.0032 (8)	−0.0189 (8)	−0.0293 (9)
C14	0.0579 (8)	0.0492 (8)	0.0578 (9)	0.0039 (6)	−0.0209 (7)	−0.0206 (7)
C15	0.0528 (8)	0.0470 (8)	0.0604 (9)	0.0042 (6)	−0.0135 (7)	−0.0259 (7)
C16	0.0696 (10)	0.0668 (10)	0.0642 (10)	−0.0043 (8)	−0.0179 (8)	−0.0313 (8)
C17	0.0841 (12)	0.0859 (14)	0.0873 (14)	−0.0208 (11)	−0.0080 (10)	−0.0510 (12)
C18	0.0763 (12)	0.0638 (12)	0.1207 (18)	−0.0121 (10)	0.0082 (12)	−0.0525 (13)
C19	0.0771 (12)	0.0520 (10)	0.1213 (18)	0.0141 (9)	−0.0182 (12)	−0.0242 (11)
C20	0.0694 (10)	0.0558 (10)	0.0954 (13)	0.0136 (8)	−0.0318 (10)	−0.0268 (9)
F3'	0.229 (7)	0.098 (4)	0.084 (3)	0.048 (4)	−0.030 (4)	0.003 (2)
F2'	0.226 (8)	0.108 (4)	0.063 (2)	−0.050 (4)	−0.005 (4)	−0.042 (3)
F1'	0.107 (4)	0.209 (9)	0.089 (3)	−0.058 (4)	−0.023 (2)	0.008 (5)

F1—C1	1.258 (9)	C11—C12	1.387 (3)
F1'—C1	1.319 (8)	C12—C13	1.369 (3)
F2—C1	1.346 (7)	C13—C14	1.382 (2)
F2'—C1	1.270 (8)	C15—C20	1.374 (2)
F3—C1	1.271 (6)	C15—C16	1.373 (2)
F3'—C1	1.328 (9)	C16—C17	1.377 (3)
N1—C8	1.312 (2)	C17—C18	1.363 (4)
N1—C9	1.380 (2)	C18—C19	1.369 (4)
N2—C8	1.3785 (19)	C19—C20	1.381 (3)
N2—C14	1.381 (2)	C3—H3	0.9300
N2—C15	1.428 (2)	C4—H4	0.9300
C1—C2	1.488 (3)	C6—H6	0.9300
C2—C3	1.377 (3)	C7—H7	0.9300
C2—C7	1.375 (2)	C10—H10	0.9300
C3—C4	1.377 (2)	C11—H11	0.9300
C4—C5	1.384 (2)	C12—H12	0.9300
C5—C8	1.469 (2)	C13—H13	0.9300
C5—C6	1.387 (2)	C16—H16	0.9300
C6—C7	1.377 (2)	C17—H17	0.9300
C9—C14	1.392 (2)	C18—H18	0.9300
C9—C10	1.390 (2)	C19—H19	0.9300
C10—C11	1.363 (3)	C20—H20	0.9300
C8—N1—C9	105.22 (13)	N2—C14—C13	131.82 (16)
C8—N2—C14	106.09 (12)	C9—C14—C13	122.50 (15)
C8—N2—C15	129.34 (12)	N2—C15—C16	119.38 (15)
C14—N2—C15	124.15 (12)	N2—C15—C20	119.91 (15)
F1—C1—F2	106.3 (5)	C16—C15—C20	120.70 (16)
F1—C1—F3	109.8 (6)	C15—C16—C17	119.60 (18)
F1—C1—C2	114.8 (3)	C16—C17—C18	120.1 (2)
F2—C1—F3	104.2 (6)	C17—C18—C19	120.2 (2)
F2—C1—C2	108.4 (3)	C18—C19—C20	120.4 (2)
F3—C1—C2	112.5 (3)	C15—C20—C19	118.9 (2)
F1'—C1—C2	114.9 (3)	C2—C3—H3	120.00
F2'—C1—C2	117.1 (4)	C4—C3—H3	120.00
F3'—C1—C2	112.0 (4)	C3—C4—H4	120.00
F1'—C1—F2'	104.8 (8)	C5—C4—H4	120.00
F1'—C1—F3'	103.7 (8)	C5—C6—H6	120.00
F2'—C1—F3'	102.8 (6)	C7—C6—H6	120.00
C1—C2—C3	119.76 (17)	C2—C7—H7	120.00
C1—C2—C7	120.63 (18)	C6—C7—H7	120.00
C3—C2—C7	119.62 (15)	C9—C10—H10	121.00
C2—C3—C4	120.44 (16)	C11—C10—H10	121.00
C3—C4—C5	120.38 (17)	C10—C11—H11	119.00
C4—C5—C6	118.73 (14)	C12—C11—H11	119.00
C4—C5—C8	117.86 (14)	C11—C12—H12	119.00
C6—C5—C8	123.37 (14)	C13—C12—H12	119.00
C5—C6—C7	120.67 (16)	C12—C13—H13	122.00
C2—C7—C6	120.13 (17)	C14—C13—H13	122.00
N1—C8—N2	112.81 (13)	C15—C16—H16	120.00
N1—C8—C5	122.94 (14)	C17—C16—H16	120.00
N2—C8—C5	124.24 (14)	C16—C17—H17	120.00
N1—C9—C10	130.14 (16)	C18—C17—H17	120.00
N1—C9—C14	110.21 (14)	C17—C18—H18	120.00
C10—C9—C14	119.65 (15)	C19—C18—H18	120.00
C9—C10—C11	117.88 (17)	C18—C19—H19	120.00
C10—C11—C12	121.69 (18)	C20—C19—H19	120.00
C11—C12—C13	121.68 (17)	C15—C20—H20	121.00
C12—C13—C14	116.59 (17)	C19—C20—H20	121.00
N2—C14—C9	105.68 (13)
C9—N1—C8—C5	−178.47 (15)	C3—C4—C5—C8	179.82 (16)
C8—N1—C9—C10	179.79 (19)	C6—C5—C8—N1	147.01 (17)
C9—N1—C8—N2	0.13 (19)	C4—C5—C8—N2	150.81 (16)
C8—N1—C9—C14	−0.27 (19)	C8—C5—C6—C7	−179.41 (16)
C8—N2—C14—C9	−0.22 (18)	C4—C5—C6—C7	−1.7 (3)
C15—N2—C14—C9	−173.36 (15)	C4—C5—C8—N1	−30.8 (2)
C14—N2—C15—C20	114.16 (19)	C6—C5—C8—N2	−31.4 (3)
C14—N2—C8—N1	0.06 (19)	C5—C6—C7—C2	−0.2 (3)
C15—N2—C8—C5	−8.7 (3)	N1—C9—C10—C11	−179.91 (19)
C8—N2—C14—C13	179.45 (19)	C14—C9—C10—C11	0.2 (3)
C14—N2—C8—C5	178.63 (15)	N1—C9—C14—N2	0.31 (19)
C8—N2—C15—C20	−57.3 (2)	C10—C9—C14—N2	−179.74 (16)
C15—N2—C8—N1	172.71 (15)	C10—C9—C14—C13	0.6 (3)
C14—N2—C15—C16	−64.8 (2)	N1—C9—C14—C13	−179.40 (16)
C8—N2—C15—C16	123.79 (18)	C9—C10—C11—C12	−0.5 (3)
C15—N2—C14—C13	6.3 (3)	C10—C11—C12—C13	0.1 (3)
F1—C1—C2—C3	−162.7 (5)	C11—C12—C13—C14	0.6 (3)
F1—C1—C2—C7	16.9 (6)	C12—C13—C14—N2	179.49 (18)
F3—C1—C2—C3	−36.2 (7)	C12—C13—C14—C9	−0.9 (3)
F2—C1—C2—C3	78.6 (4)	N2—C15—C16—C17	178.39 (17)
F2—C1—C2—C7	−101.9 (4)	C20—C15—C16—C17	−0.5 (3)
F3—C1—C2—C7	143.4 (6)	N2—C15—C20—C19	−179.86 (19)
C7—C2—C3—C4	−1.4 (3)	C16—C15—C20—C19	−1.0 (3)
C3—C2—C7—C6	1.7 (3)	C15—C16—C17—C18	1.2 (3)
C1—C2—C3—C4	178.2 (2)	C16—C17—C18—C19	−0.3 (4)
C1—C2—C7—C6	−177.9 (2)	C17—C18—C19—C20	−1.2 (4)
C2—C3—C4—C5	−0.5 (3)	C18—C19—C20—C15	1.8 (4)
C3—C4—C5—C6	2.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···F3i	0.93	2.54	3.429 (6)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯F3i	0.93	2.54	3.429 (6)	160

Symmetry code: (i) .