1-(4-Fluoro-benz-yl)-2-(pyridin-2-yl)-1H-benzimidazole.

In the title compound, C19H14FN3, the dihedral angles between the benzimidazole unit (r.m.s. deviation= 0.017 Å) and the pyridine and benzene rings are 24.46 (4) and 81.87 (3)°, respectively. In the crystal, mol-ecules are stacked along the a-axis direction by C-H⋯π inter-actions.

Related literature

For the use of 2-(2-pyrid­yl)benzimidazole in coordination chemistry, see: Boca et al. (1997 ▶); De Castro et al. (1991 ▶); Khalil et al. (2001 ▶); Maekawa et al. (1994 ▶). For deprotonation of the NH group in 2-(2-pyrid­yl)benzimidazole, see: Chiswell et al. (1964 ▶); Harkins et al. (1956 ▶); Haga (1983 ▶). For functionalization of 2-(2-pyrid­yl)benzimidazole, see: Ali et al. (1998 ▶); Hossain et al. (2001 ▶); Sahin et al. (2010 ▶). For related structures, see: Çelik et al. (2007 ▶, 2009 ▶).

Experimental

Crystal data

C19H14FN3

M = 303.33

Monoclinic,

a = 4.7363 (5) Å

b = 15.4102 (17) Å

c = 20.953 (2) Å

β = 95.363 (8)°

V = 1522.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.2 × 0.2 × 0.2 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.984, T max = 0.984

13325 measured reflections

3133 independent reflections

2355 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.103

S = 0.93

3133 reflections

208 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814005947/bq2393sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814005947/bq2393Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814005947/bq2393Isup3.cml

CCDC reference: 992223

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

C19H14FN3	F(000) = 632
Mr = 303.33	Dx = 1.323 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 0 reflections
a = 4.7363 (5) Å	θ = 2.4–26.7°
b = 15.4102 (17) Å	µ = 0.09 mm−1
c = 20.953 (2) Å	T = 296 K
β = 95.363 (8)°	Stick, orange
V = 1522.6 (3) Å3	0.2 × 0.2 × 0.2 mm
Z = 4

Bruker APEXII CCD diffractometer	3133 independent reflections
Radiation source: sealed tube	2355 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 26.7°, θmin = 2.4°
Absorption correction: multi-scan (Blessing, 1995)	h = −5→5
Tmin = 0.984, Tmax = 0.984	k = −19→18
13325 measured reflections	l = −26→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)] = 0.038	Hydrogen site location: mixed
wR(F2) = 0.103	H-atom parameters constrained
S = 0.93	w = 1/[σ2(Fo2) + (0.0502P)2 + 0.1779P] where P = (Fo2 + 2Fc2)/3
3133 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.14 e Å−3
1 restraint	Δρmin = −0.17 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
N1	0.3612 (2)	0.95634 (7)	0.32306 (5)	0.0598 (3)
N2	0.1288 (2)	1.03423 (7)	0.24400 (6)	0.0669 (3)
C14	0.3980 (3)	0.81860 (8)	0.38380 (6)	0.0574 (3)
C6	0.0419 (3)	1.05982 (8)	0.30241 (7)	0.0629 (3)
C5	0.1882 (3)	1.01343 (8)	0.35209 (7)	0.0607 (3)
C13	0.5514 (3)	0.89547 (9)	0.35911 (7)	0.0661 (4)
H13A	0.6512	0.9256	0.3951	0.079*
H13B	0.6915	0.8750	0.3317	0.079*
C7	0.3181 (3)	0.97274 (8)	0.25818 (7)	0.0602 (3)
C17	0.1266 (4)	0.67652 (9)	0.42898 (8)	0.0785 (4)
F	−0.0115 (3)	0.60689 (7)	0.45190 (6)	0.1195 (4)
C1	−0.1590 (3)	1.12201 (9)	0.31618 (9)	0.0762 (4)
H1	−0.2638	1.1521	0.2836	0.091*
C4	0.1534 (3)	1.02938 (10)	0.41615 (8)	0.0719 (4)
H4	0.2555	0.9989	0.4490	0.086*
C15	0.2114 (3)	0.76997 (10)	0.34407 (7)	0.0736 (4)
H15	0.1766	0.7856	0.3012	0.088*
N3	0.5846 (3)	0.85244 (9)	0.22169 (7)	0.0831 (4)
C19	0.4444 (3)	0.79317 (11)	0.44710 (7)	0.0770 (4)
H19	0.5696	0.8248	0.4749	0.092*
C16	0.0746 (4)	0.69844 (11)	0.36643 (8)	0.0856 (5)
H16	−0.0506	0.6661	0.3391	0.103*
C8	0.4713 (3)	0.93024 (9)	0.20851 (7)	0.0635 (4)
C11	0.7609 (4)	0.85310 (15)	0.11857 (10)	0.0983 (6)
H11	0.8632	0.8251	0.0889	0.118*
C2	−0.1960 (4)	1.13709 (10)	0.37944 (10)	0.0835 (5)
H2	−0.3286	1.1781	0.3897	0.100*
C18	0.3089 (4)	0.72168 (11)	0.47001 (8)	0.0865 (5)
H18	0.3423	0.7050	0.5127	0.104*
C3	−0.0396 (4)	1.09246 (11)	0.42858 (9)	0.0818 (5)
H3	−0.0664	1.1056	0.4709	0.098*
C9	0.4926 (4)	0.97168 (11)	0.15093 (8)	0.0861 (5)
H9	0.4076	1.0254	0.1428	0.103*
C12	0.7260 (4)	0.81593 (13)	0.17637 (10)	0.0989 (6)
H12	0.8060	0.7615	0.1848	0.119*
C10	0.6421 (5)	0.93216 (14)	0.10555 (9)	0.1017 (6)
H10	0.6613	0.9593	0.0665	0.122*

	U11	U22	U33	U12	U13	U23
N1	0.0538 (6)	0.0525 (6)	0.0728 (7)	−0.0057 (5)	0.0044 (5)	−0.0023 (5)
N2	0.0652 (7)	0.0542 (6)	0.0812 (8)	−0.0007 (6)	0.0058 (6)	0.0017 (5)
C14	0.0518 (7)	0.0561 (7)	0.0633 (8)	0.0052 (6)	−0.0008 (6)	−0.0061 (6)
C6	0.0578 (7)	0.0471 (7)	0.0847 (9)	−0.0100 (6)	0.0115 (7)	−0.0031 (6)
C5	0.0533 (7)	0.0503 (7)	0.0792 (9)	−0.0144 (6)	0.0099 (6)	−0.0060 (6)
C13	0.0524 (7)	0.0691 (9)	0.0748 (9)	−0.0043 (6)	−0.0048 (6)	−0.0033 (7)
C7	0.0565 (7)	0.0506 (7)	0.0730 (9)	−0.0085 (6)	0.0037 (6)	−0.0018 (6)
C17	0.1041 (12)	0.0522 (8)	0.0826 (10)	0.0003 (8)	0.0259 (9)	−0.0004 (7)
F	0.1701 (11)	0.0738 (6)	0.1201 (9)	−0.0228 (7)	0.0432 (8)	0.0116 (6)
C1	0.0679 (9)	0.0543 (8)	0.1076 (12)	−0.0041 (7)	0.0143 (8)	−0.0013 (8)
C4	0.0684 (9)	0.0682 (9)	0.0801 (10)	−0.0188 (8)	0.0117 (7)	−0.0090 (7)
C15	0.0845 (10)	0.0723 (9)	0.0620 (8)	−0.0157 (8)	−0.0036 (7)	−0.0007 (7)
N3	0.0868 (9)	0.0744 (9)	0.0890 (9)	0.0175 (7)	0.0135 (7)	−0.0045 (7)
C19	0.0821 (10)	0.0777 (10)	0.0679 (9)	0.0005 (8)	−0.0102 (7)	−0.0059 (7)
C16	0.1046 (12)	0.0715 (10)	0.0801 (10)	−0.0271 (9)	0.0046 (9)	−0.0079 (8)
C8	0.0572 (8)	0.0603 (8)	0.0726 (9)	−0.0070 (6)	0.0036 (6)	−0.0066 (7)
C11	0.0899 (12)	0.1126 (15)	0.0951 (13)	0.0017 (12)	0.0224 (10)	−0.0276 (11)
C2	0.0741 (10)	0.0606 (9)	0.1198 (14)	−0.0072 (8)	0.0304 (10)	−0.0160 (9)
C18	0.1154 (13)	0.0768 (11)	0.0666 (9)	0.0084 (10)	0.0046 (9)	0.0092 (8)
C3	0.0811 (11)	0.0713 (10)	0.0966 (12)	−0.0190 (9)	0.0276 (9)	−0.0210 (9)
C9	0.1051 (13)	0.0737 (10)	0.0802 (10)	−0.0003 (9)	0.0134 (9)	0.0007 (8)
C12	0.0997 (13)	0.0955 (13)	0.1023 (13)	0.0277 (11)	0.0142 (11)	−0.0161 (11)
C10	0.1226 (16)	0.1067 (15)	0.0795 (11)	−0.0147 (13)	0.0283 (11)	−0.0091 (10)

N1—C7	1.3790 (17)	C4—H4	0.9300
N1—C5	1.3815 (17)	C15—C16	1.382 (2)
N1—C13	1.4612 (17)	C15—H15	0.9300
N2—C7	1.3192 (17)	N3—C8	1.3319 (19)
N2—C6	1.3845 (18)	N3—C12	1.336 (2)
C14—C15	1.3778 (18)	C19—C18	1.383 (2)
C14—C19	1.381 (2)	C19—H19	0.9300
C14—C13	1.5065 (19)	C16—H16	0.9300
C6—C5	1.393 (2)	C8—C9	1.377 (2)
C6—C1	1.399 (2)	C11—C10	1.359 (3)
C5—C4	1.389 (2)	C11—C12	1.364 (3)
C13—H13A	0.9700	C11—H11	0.9300
C13—H13B	0.9700	C2—C3	1.392 (2)
C7—C8	1.4765 (19)	C2—H2	0.9300
C17—C18	1.353 (2)	C18—H18	0.9300
C17—C16	1.354 (2)	C3—H3	0.9300
C17—F	1.3671 (18)	C9—C10	1.379 (2)
C1—C2	1.373 (2)	C9—H9	0.9300
C1—H1	0.9300	C12—H12	0.9300
C4—C3	1.376 (2)	C10—H10	0.9300
C7—N1—C5	106.14 (11)	C16—C15—H15	119.2
C7—N1—C13	130.90 (12)	C8—N3—C12	116.78 (15)
C5—N1—C13	122.93 (12)	C14—C19—C18	121.46 (14)
C7—N2—C6	104.92 (12)	C14—C19—H19	119.3
C15—C14—C19	117.49 (13)	C18—C19—H19	119.3
C15—C14—C13	121.54 (12)	C17—C16—C15	118.58 (15)
C19—C14—C13	120.95 (12)	C17—C16—H16	120.7
N2—C6—C5	110.25 (12)	C15—C16—H16	120.7
N2—C6—C1	129.90 (14)	N3—C8—C9	122.55 (15)
C5—C6—C1	119.85 (14)	N3—C8—C7	117.91 (13)
N1—C5—C4	131.82 (14)	C9—C8—C7	119.54 (14)
N1—C5—C6	105.78 (12)	C10—C11—C12	118.21 (18)
C4—C5—C6	122.37 (14)	C10—C11—H11	120.9
N1—C13—C14	112.85 (10)	C12—C11—H11	120.9
N1—C13—H13A	109.0	C1—C2—C3	121.54 (15)
C14—C13—H13A	109.0	C1—C2—H2	119.2
N1—C13—H13B	109.0	C3—C2—H2	119.2
C14—C13—H13B	109.0	C17—C18—C19	118.58 (15)
H13A—C13—H13B	107.8	C17—C18—H18	120.7
N2—C7—N1	112.87 (12)	C19—C18—H18	120.7
N2—C7—C8	121.89 (13)	C4—C3—C2	121.72 (16)
N1—C7—C8	125.19 (13)	C4—C3—H3	119.1
C18—C17—C16	122.33 (15)	C2—C3—H3	119.1
C18—C17—F	118.58 (15)	C8—C9—C10	118.93 (17)
C16—C17—F	119.09 (16)	C8—C9—H9	120.5
C2—C1—C6	117.76 (16)	C10—C9—H9	120.5
C2—C1—H1	121.1	N3—C12—C11	124.37 (18)
C6—C1—H1	121.1	N3—C12—H12	117.8
C3—C4—C5	116.67 (16)	C11—C12—H12	117.8
C3—C4—H4	121.7	C11—C10—C9	119.15 (18)
C5—C4—H4	121.7	C11—C10—H10	120.4
C14—C15—C16	121.56 (14)	C9—C10—H10	120.4
C14—C15—H15	119.2
C7—N2—C6—C5	1.27 (14)	C19—C14—C15—C16	0.1 (2)
C7—N2—C6—C1	−178.94 (13)	C13—C14—C15—C16	178.76 (15)
C7—N1—C5—C4	−176.42 (14)	C15—C14—C19—C18	−0.1 (2)
C13—N1—C5—C4	1.7 (2)	C13—C14—C19—C18	−178.73 (14)
C7—N1—C5—C6	1.84 (13)	C18—C17—C16—C15	−0.5 (3)
C13—N1—C5—C6	179.92 (11)	F—C17—C16—C15	178.77 (15)
N2—C6—C5—N1	−1.96 (14)	C14—C15—C16—C17	0.2 (3)
C1—C6—C5—N1	178.22 (11)	C12—N3—C8—C9	0.9 (2)
N2—C6—C5—C4	176.50 (12)	C12—N3—C8—C7	−178.95 (14)
C1—C6—C5—C4	−3.32 (19)	N2—C7—C8—N3	−158.51 (13)
C7—N1—C13—C14	−106.39 (15)	N1—C7—C8—N3	24.2 (2)
C5—N1—C13—C14	76.04 (15)	N2—C7—C8—C9	21.6 (2)
C15—C14—C13—N1	50.84 (18)	N1—C7—C8—C9	−155.75 (14)
C19—C14—C13—N1	−130.59 (14)	C6—C1—C2—C3	0.1 (2)
C6—N2—C7—N1	−0.06 (15)	C16—C17—C18—C19	0.6 (3)
C6—N2—C7—C8	−177.69 (11)	F—C17—C18—C19	−178.74 (15)
C5—N1—C7—N2	−1.16 (14)	C14—C19—C18—C17	−0.2 (3)
C13—N1—C7—N2	−179.03 (12)	C5—C4—C3—C2	1.1 (2)
C5—N1—C7—C8	176.39 (12)	C1—C2—C3—C4	−1.9 (2)
C13—N1—C7—C8	−1.5 (2)	N3—C8—C9—C10	−1.4 (3)
N2—C6—C1—C2	−177.38 (14)	C7—C8—C9—C10	178.46 (15)
C5—C6—C1—C2	2.40 (19)	C8—N3—C12—C11	0.1 (3)
N1—C5—C4—C3	179.55 (13)	C10—C11—C12—N3	−0.7 (3)
C6—C5—C4—C3	1.5 (2)	C12—C11—C10—C9	0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···Cgi	0.97	2.94	3.486 (2)	117

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯Cg i	0.97	2.94	3.486 (2)	117

Symmetry code: (i) .