2-(3,4-Di-fluoro-phen-yl)-1H-benzimidazole.

In the title mol-ecule, C13H8F2N2, the dihedral angle between the benzimidazole ring system and the di-fluoro-substituted benzene ring is 30.0 (1)°. In the crystal, mol-ecules are linked by N-H⋯N hydrogen bonds, forming chains along [010]. In addition, weak C-H⋯F hydrogen bonds connect chains into a two-dimensional network parallel to (001). A weak C-H⋯π inter-action is observed between an H atom of the benzimidazole ring sytem and the π system of the di-fluoro-substituted benzene ring.

Related literature

For the therapeutic and medicinal properties of benzimidazole derivatives, see: Chimirri et al. (1991 ▶); Ishihara et al. (1994 ▶); Kubo et al. (1993 ▶). For related structures, see: Rashid et al. (2007 ▶); Jayamoorthy et al. (2012 ▶); Yoon et al. (2012 ▶); Fathima et al. (2013 ▶).

Experimental

Crystal data

C13H8F2N2

M = 230.21

Orthorhombic,

a = 8.7195 (17) Å

b = 9.9454 (19) Å

c = 23.389 (4) Å

V = 2028.2 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.12 mm−1

T = 100 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 = 0.982, T max = 0.984

13072 measured reflections

2209 independent reflections

1558 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.156

S = 1.01

2209 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.31 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/S1600536813028559/lh5659sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813028559/lh5659Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813028559/lh5659Isup3.cml

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

C13H8F2N2	F(000) = 944
Mr = 230.21	Dx = 1.508 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2209 reflections
a = 8.7195 (17) Å	θ = 2.9–27.0°
b = 9.9454 (19) Å	µ = 0.12 mm−1
c = 23.389 (4) Å	T = 100 K
V = 2028.2 (7) Å3	Block, yellow
Z = 8	0.18 × 0.16 × 0.16 mm

Bruker SMART APEX CCD detector diffractometer	2209 independent reflections
Radiation source: fine-focus sealed tube	1558 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.067
ω scans	θmax = 27.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −11→10
Tmin = 0.982, Tmax = 0.984	k = −11→12
13072 measured reflections	l = −28→29

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0725P)2 + 2.7172P] where P = (Fo2 + 2Fc2)/3
2209 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.31 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
F1	0.14852 (18)	0.58743 (18)	0.48006 (8)	0.0366 (5)
F2	0.38138 (19)	0.75233 (17)	0.50344 (7)	0.0341 (5)
N1	0.8188 (2)	0.5958 (2)	0.36510 (9)	0.0174 (5)
H1	0.8081	0.6819	0.3727	0.021*
N2	0.7666 (2)	0.3748 (2)	0.36264 (9)	0.0182 (5)
C1	0.9394 (3)	0.5363 (2)	0.33662 (11)	0.0177 (5)
C2	0.7191 (3)	0.4952 (2)	0.37920 (10)	0.0160 (5)
C3	1.1638 (3)	0.4987 (3)	0.28151 (11)	0.0211 (6)
H3A	1.2526	0.5311	0.2624	0.025*
C4	1.1307 (3)	0.3607 (3)	0.28051 (11)	0.0219 (6)
H4	1.1975	0.3017	0.2605	0.026*
C5	1.0038 (3)	0.3082 (3)	0.30778 (11)	0.0204 (6)
H5	0.9838	0.2143	0.3076	0.025*
C6	0.9064 (3)	0.3973 (2)	0.33543 (11)	0.0175 (5)
C7	1.0692 (3)	0.5888 (3)	0.30993 (11)	0.0212 (6)
H7	1.0918	0.6822	0.3111	0.025*
C8	0.5694 (3)	0.5218 (2)	0.40631 (11)	0.0185 (5)
C9	0.4478 (3)	0.4362 (3)	0.39494 (12)	0.0228 (6)
H9	0.4632	0.3615	0.3703	0.027*
C10	0.3033 (3)	0.4573 (3)	0.41895 (13)	0.0268 (6)
H10	0.2201	0.3988	0.4106	0.032*
C11	0.2849 (3)	0.5654 (3)	0.45506 (12)	0.0233 (6)
C12	0.4062 (3)	0.6501 (3)	0.46667 (12)	0.0216 (6)
C13	0.5477 (3)	0.6304 (2)	0.44261 (11)	0.0188 (5)
H13	0.6298	0.6902	0.4507	0.023*

	U11	U22	U33	U12	U13	U23
F1	0.0223 (9)	0.0372 (10)	0.0504 (11)	−0.0001 (7)	0.0114 (8)	−0.0089 (8)
F2	0.0312 (9)	0.0280 (9)	0.0430 (10)	0.0038 (8)	0.0066 (8)	−0.0127 (8)
N1	0.0202 (11)	0.0083 (9)	0.0236 (11)	0.0000 (8)	0.0013 (9)	−0.0010 (8)
N2	0.0216 (11)	0.0125 (10)	0.0204 (11)	0.0017 (9)	−0.0007 (9)	−0.0011 (8)
C1	0.0205 (13)	0.0122 (11)	0.0204 (13)	0.0040 (10)	−0.0022 (10)	0.0001 (10)
C2	0.0184 (12)	0.0117 (11)	0.0178 (12)	−0.0012 (10)	−0.0026 (10)	0.0017 (9)
C3	0.0179 (12)	0.0194 (13)	0.0261 (14)	0.0004 (11)	0.0063 (11)	0.0005 (11)
C4	0.0233 (13)	0.0178 (13)	0.0247 (14)	0.0055 (11)	0.0006 (11)	0.0001 (11)
C5	0.0245 (13)	0.0128 (12)	0.0240 (13)	0.0013 (10)	−0.0030 (11)	0.0002 (10)
C6	0.0185 (12)	0.0134 (12)	0.0205 (13)	−0.0027 (10)	−0.0031 (10)	0.0023 (10)
C7	0.0252 (14)	0.0113 (12)	0.0270 (14)	−0.0007 (10)	0.0031 (11)	0.0012 (10)
C8	0.0206 (13)	0.0146 (12)	0.0202 (13)	−0.0004 (10)	−0.0031 (10)	0.0047 (10)
C9	0.0278 (14)	0.0150 (12)	0.0257 (14)	−0.0007 (11)	0.0017 (11)	−0.0045 (11)
C10	0.0221 (14)	0.0246 (14)	0.0337 (15)	−0.0055 (12)	−0.0037 (12)	0.0003 (12)
C11	0.0164 (13)	0.0255 (14)	0.0281 (14)	0.0026 (11)	0.0041 (11)	0.0033 (11)
C12	0.0233 (13)	0.0134 (12)	0.0280 (15)	0.0041 (10)	−0.0010 (11)	−0.0011 (10)
C13	0.0183 (13)	0.0125 (12)	0.0257 (14)	−0.0008 (10)	−0.0002 (11)	0.0022 (10)

F1—C11	1.344 (3)	C4—H4	0.9500
F2—C12	1.349 (3)	C5—C6	1.388 (4)
N1—C2	1.366 (3)	C5—H5	0.9500
N1—C1	1.378 (3)	C7—H7	0.9500
N1—H1	0.8800	C8—C9	1.386 (4)
N2—C2	1.326 (3)	C8—C13	1.386 (4)
N2—C6	1.393 (3)	C9—C10	1.396 (4)
C1—C7	1.394 (4)	C9—H9	0.9500
C1—C6	1.412 (3)	C10—C11	1.376 (4)
C2—C8	1.474 (4)	C10—H10	0.9500
C3—C7	1.388 (4)	C11—C12	1.379 (4)
C3—C4	1.403 (4)	C12—C13	1.371 (4)
C3—H3A	0.9500	C13—H13	0.9500
C4—C5	1.380 (4)
C2—N1—C1	106.7 (2)	C3—C7—C1	117.1 (2)
C2—N1—H1	126.6	C3—C7—H7	121.5
C1—N1—H1	126.6	C1—C7—H7	121.5
C2—N2—C6	105.2 (2)	C9—C8—C13	119.5 (2)
N1—C1—C7	132.4 (2)	C9—C8—C2	118.9 (2)
N1—C1—C6	105.9 (2)	C13—C8—C2	121.6 (2)
C7—C1—C6	121.6 (2)	C8—C9—C10	121.4 (2)
N2—C2—N1	113.1 (2)	C8—C9—H9	119.3
N2—C2—C8	124.4 (2)	C10—C9—H9	119.3
N1—C2—C8	122.4 (2)	C11—C10—C9	118.0 (2)
C7—C3—C4	121.2 (2)	C11—C10—H10	121.0
C7—C3—H3A	119.4	C9—C10—H10	121.0
C4—C3—H3A	119.4	F1—C11—C10	119.8 (2)
C5—C4—C3	121.8 (2)	F1—C11—C12	119.5 (2)
C5—C4—H4	119.1	C10—C11—C12	120.6 (2)
C3—C4—H4	119.1	F2—C12—C13	120.9 (2)
C4—C5—C6	117.7 (2)	F2—C12—C11	117.6 (2)
C4—C5—H5	121.1	C13—C12—C11	121.4 (2)
C6—C5—H5	121.1	C12—C13—C8	119.1 (2)
C5—C6—N2	130.2 (2)	C12—C13—H13	120.5
C5—C6—C1	120.6 (2)	C8—C13—H13	120.5
N2—C6—C1	109.1 (2)
C2—N1—C1—C7	176.2 (3)	C6—C1—C7—C3	0.7 (4)
C2—N1—C1—C6	−0.7 (3)	N2—C2—C8—C9	−26.6 (4)
C6—N2—C2—N1	−0.5 (3)	N1—C2—C8—C9	148.7 (2)
C6—N2—C2—C8	175.3 (2)	N2—C2—C8—C13	153.6 (2)
C1—N1—C2—N2	0.7 (3)	N1—C2—C8—C13	−31.1 (4)
C1—N1—C2—C8	−175.1 (2)	C13—C8—C9—C10	0.5 (4)
C7—C3—C4—C5	−0.3 (4)	C2—C8—C9—C10	−179.4 (2)
C3—C4—C5—C6	1.6 (4)	C8—C9—C10—C11	−0.8 (4)
C4—C5—C6—N2	175.1 (2)	C9—C10—C11—F1	−178.5 (2)
C4—C5—C6—C1	−1.6 (4)	C9—C10—C11—C12	0.4 (4)
C2—N2—C6—C5	−177.0 (3)	F1—C11—C12—F2	0.3 (4)
C2—N2—C6—C1	0.0 (3)	C10—C11—C12—F2	−178.5 (2)
N1—C1—C6—C5	177.8 (2)	F1—C11—C12—C13	179.2 (2)
C7—C1—C6—C5	0.5 (4)	C10—C11—C12—C13	0.4 (4)
N1—C1—C6—N2	0.4 (3)	F2—C12—C13—C8	178.2 (2)
C7—C1—C6—N2	−176.8 (2)	C11—C12—C13—C8	−0.7 (4)
C4—C3—C7—C1	−0.8 (4)	C9—C8—C13—C12	0.3 (4)
N1—C1—C7—C3	−175.7 (3)	C2—C8—C13—C12	−179.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2i	0.88	2.04	2.874 (3)	158
C13—H13···F2ii	0.95	2.51	3.379 (3)	153
C3—H3A···Cgiii	0.95	2.89	3.529 (3)	125

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the ring C9–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2i	0.88	2.04	2.874 (3)	158
C13—H13⋯F2ii	0.95	2.51	3.379 (3)	153
C3—H3A⋯Cg iii	0.95	2.89	3.529 (3)	125

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