4-(1H-Benzimidazol-2-yl)benzonitrile.

The mol-ecule of the title compound, C(14)H(9)N(3), is essentially planar, the dihedral angle formed by the benzimidazole ring system with the benzene ring being 3.87 (3)°. In the crystal packing, mol-ecules are linked into zigzag chains running parallel to the b axis by inter-molecular N-H⋯N hydrogen-bond inter-actions.

Related literature

For related literature, see: Gallagher et al. (2001 ▶); Howarth & Hanlon (2001 ▶); Kazak et al. (2006 ▶); Li et al. (1998 ▶); Íkizler & Sancak (1992 ▶).

Experimental

Crystal data

C14H9N3

M = 219.24

Monoclinic,

a = 7.2172 (10) Å

b = 11.818 (2) Å

c = 12.719 (2) Å

β = 92.057 (7)°

V = 1084.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 (2) K

0.35 × 0.15 × 0.10 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.910, T max = 1.000 (expected range = 0.903–0.992)

11203 measured reflections

2581 independent reflections

2073 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.118

S = 1.08

2581 reflections

159 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.17 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808012932/rz2211sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012932/rz2211Isup2.hkl

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

C14H9N3	F000 = 456
Mr = 219.24	Dx = 1.343 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2461 reflections
a = 7.2172 (10) Å	θ = 3.2–27.5º
b = 11.818 (2) Å	µ = 0.08 mm−1
c = 12.719 (2) Å	T = 293 (2) K
β = 92.057 (7)º	Prism, colourless
V = 1084.1 (3) Å3	0.35 × 0.15 × 0.10 mm
Z = 4

Rigaku Mercury2 (2x2 bin mode) diffractometer	2581 independent reflections
Radiation source: fine-focus sealed tube	2073 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.037
Detector resolution: 13.6612 pixels mm-1	θmax = 27.9º
T = 293(2) K	θmin = 2.4º
CCD_Profile_fitting scans	h = −9→9
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)	k = −15→15
Tmin = 0.911, Tmax = 1.000	l = −16→16
11203 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.046	w = 1/[σ2(Fo2) + (0.056P)2 + 0.1336P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.118	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.16 e Å−3
2581 reflections	Δρmin = −0.17 e Å−3
159 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.115 (7)
Secondary atom site location: difference Fourier map

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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
N2	0.23276 (15)	0.98417 (9)	−0.07818 (9)	0.0381 (3)
C8	0.14908 (17)	0.84634 (11)	0.06171 (10)	0.0367 (3)
N1	0.08189 (15)	0.82641 (9)	−0.12784 (8)	0.0404 (3)
C7	0.15245 (17)	0.88501 (10)	−0.04772 (10)	0.0360 (3)
N3	0.11261 (18)	0.68424 (11)	0.45407 (10)	0.0543 (3)
C11	0.13598 (18)	0.76582 (11)	0.26664 (10)	0.0389 (3)
C6	0.21340 (17)	0.98948 (10)	−0.18604 (10)	0.0363 (3)
C9	0.23427 (19)	0.90578 (12)	0.14485 (10)	0.0439 (3)
H9A	0.2963	0.9730	0.1315	0.053*
C1	0.11833 (17)	0.89042 (11)	−0.21590 (10)	0.0377 (3)
C5	0.2689 (2)	1.06900 (11)	−0.25904 (11)	0.0443 (3)
H5A	0.3300	1.1351	−0.2384	0.053*
C14	0.12508 (18)	0.72221 (12)	0.37201 (11)	0.0425 (3)
C13	0.05688 (19)	0.74595 (12)	0.08336 (11)	0.0432 (3)
H13A	−0.0015	0.7058	0.0287	0.052*
C12	0.05122 (19)	0.70550 (12)	0.18459 (11)	0.0436 (3)
H12A	−0.0093	0.6378	0.1980	0.052*
C10	0.2277 (2)	0.86617 (12)	0.24669 (11)	0.0459 (3)
H10A	0.2846	0.9066	0.3017	0.055*
C4	0.2292 (2)	1.04531 (13)	−0.36315 (11)	0.0496 (4)
H4A	0.2652	1.0964	−0.4142	0.060*
C3	0.1362 (2)	0.94670 (13)	−0.39450 (11)	0.0492 (4)
H3A	0.1134	0.9332	−0.4658	0.059*
C2	0.07759 (19)	0.86882 (12)	−0.32224 (10)	0.0451 (3)
H2B	0.0131	0.8041	−0.3435	0.054*
H2A	0.281 (2)	1.0377 (15)	−0.0336 (13)	0.058 (5)*

	U11	U22	U33	U12	U13	U23
N2	0.0439 (6)	0.0349 (6)	0.0354 (6)	0.0001 (4)	0.0010 (5)	−0.0012 (4)
C8	0.0358 (6)	0.0391 (7)	0.0352 (7)	0.0032 (5)	0.0033 (5)	0.0003 (5)
N1	0.0455 (6)	0.0407 (6)	0.0349 (6)	−0.0031 (5)	−0.0001 (4)	0.0003 (4)
C7	0.0377 (6)	0.0355 (6)	0.0350 (7)	0.0035 (5)	0.0025 (5)	0.0001 (5)
N3	0.0641 (8)	0.0563 (8)	0.0425 (7)	−0.0005 (6)	0.0002 (6)	0.0094 (6)
C11	0.0391 (7)	0.0420 (7)	0.0357 (7)	0.0050 (5)	0.0029 (5)	0.0042 (5)
C6	0.0382 (6)	0.0351 (7)	0.0357 (7)	0.0050 (5)	0.0020 (5)	0.0003 (5)
C9	0.0535 (8)	0.0389 (7)	0.0393 (8)	−0.0058 (6)	−0.0006 (6)	0.0025 (5)
C1	0.0394 (6)	0.0375 (7)	0.0360 (7)	0.0042 (5)	−0.0002 (5)	0.0023 (5)
C5	0.0502 (8)	0.0360 (7)	0.0468 (8)	0.0010 (6)	0.0028 (6)	0.0046 (6)
C14	0.0468 (8)	0.0425 (7)	0.0381 (7)	0.0035 (5)	0.0011 (6)	0.0026 (5)
C13	0.0463 (7)	0.0464 (8)	0.0369 (7)	−0.0059 (6)	0.0000 (5)	−0.0026 (6)
C12	0.0461 (7)	0.0434 (7)	0.0414 (7)	−0.0061 (6)	0.0034 (6)	0.0025 (6)
C10	0.0549 (8)	0.0448 (8)	0.0376 (7)	−0.0049 (6)	−0.0038 (6)	−0.0009 (6)
C4	0.0590 (9)	0.0472 (8)	0.0430 (8)	0.0079 (6)	0.0050 (6)	0.0122 (6)
C3	0.0611 (9)	0.0508 (8)	0.0354 (7)	0.0113 (7)	−0.0042 (6)	0.0050 (6)
C2	0.0519 (8)	0.0439 (7)	0.0390 (7)	0.0023 (6)	−0.0058 (6)	−0.0016 (6)

N2—C7	1.3696 (16)	C9—C10	1.3798 (19)
N2—C6	1.3754 (17)	C9—H9A	0.9300
N2—H2A	0.910 (17)	C1—C2	1.3972 (18)
C8—C13	1.3926 (19)	C5—C4	1.374 (2)
C8—C9	1.3940 (19)	C5—H5A	0.9300
C8—C7	1.4661 (17)	C13—C12	1.3756 (18)
N1—C7	1.3191 (16)	C13—H13A	0.9300
N1—C1	1.3846 (16)	C12—H12A	0.9300
N3—C14	1.1427 (17)	C10—H10A	0.9300
C11—C10	1.3861 (19)	C4—C3	1.396 (2)
C11—C12	1.3877 (19)	C4—H4A	0.9300
C11—C14	1.4407 (18)	C3—C2	1.378 (2)
C6—C5	1.3901 (18)	C3—H3A	0.9300
C6—C1	1.4025 (18)	C2—H2B	0.9300
C7—N2—C6	107.00 (11)	C4—C5—C6	116.80 (13)
C7—N2—H2A	125.0 (10)	C4—C5—H5A	121.6
C6—N2—H2A	127.8 (10)	C6—C5—H5A	121.6
C13—C8—C9	118.70 (12)	N3—C14—C11	177.40 (16)
C13—C8—C7	118.53 (12)	C12—C13—C8	120.77 (13)
C9—C8—C7	122.77 (12)	C12—C13—H13A	119.6
C7—N1—C1	105.01 (11)	C8—C13—H13A	119.6
N1—C7—N2	112.72 (11)	C13—C12—C11	119.89 (13)
N1—C7—C8	123.42 (12)	C13—C12—H12A	120.1
N2—C7—C8	123.84 (11)	C11—C12—H12A	120.1
C10—C11—C12	120.16 (12)	C11—C10—C9	119.67 (13)
C10—C11—C14	121.25 (12)	C11—C10—H10A	120.2
C12—C11—C14	118.59 (12)	C9—C10—H10A	120.2
N2—C6—C5	132.50 (12)	C5—C4—C3	121.81 (13)
N2—C6—C1	105.27 (11)	C5—C4—H4A	119.1
C5—C6—C1	122.23 (12)	C3—C4—H4A	119.1
C10—C9—C8	120.80 (13)	C2—C3—C4	121.54 (14)
C10—C9—H9A	119.6	C2—C3—H3A	119.2
C8—C9—H9A	119.6	C4—C3—H3A	119.2
N1—C1—C2	130.07 (12)	C3—C2—C1	117.69 (13)
N1—C1—C6	110.01 (11)	C3—C2—H2B	121.2
C2—C1—C6	119.91 (12)	C1—C2—H2B	121.2

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···N1	0.93	2.54	2.861 (2)	101
N2—H2A···N3i	0.910 (17)	2.14 (2)	3.033 (2)	169.1 (15)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯N1	0.93	2.54	2.861 (2)	101
N2—H2A⋯N3i	0.910 (17)	2.14 (2)	3.033 (2)	169.1 (15)

Symmetry code: (i) .