4-[1-(4-Cyano-benz-yl)-1H-benzimidazol-2-yl]benzonitrile.

In the title compound, C(22)H(14)N(4), a new substituted benzimidazole, three inter-molecular C-H⋯N inter-actions link neighbouring mol-ecules into different dimers with R(2) (2)(12), R(2) (2)(8) and R(2) (2)(24) ring motifs. A fourth C-H⋯N inter-action links neighbouring mol-ecules along the c axis. There is also a short inter-molecular contact between the azomethine (C=N) segment of the benzimidazole ring and one of the C atoms of a neighbouring benzene ring [N⋯C = 3.191 (5), C⋯C = 3.364 (6) Å], which links the mol-ecules along the a axis. The two cyano-benzene rings are almost perpendicular to each other, with an inter-planar angle of 87.70 (7)°. The dihedral angles between the mean planes of the benzimidazole ring and the two outer benzene rings are 36.27 (16) and 86.70 (16)°. In the crystal structure, mol-ecules are stacked down the a axis with centroid-centroid distances of 3.906 (2)-3.912 (2) Å and inter-planar distances of 3.5040 (17) and 3.6235 (17) Å.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For benzimidazole chemistry, reaction mechanisms and their bioactivity, see, for example: Latif et al. (1983 ▶); Craigo et al. (1999 ▶); Gudmundsson et al. (2000 ▶); Trivedi et al. (2006); Kim et al. (1996 ▶); Ramla et al. (2006 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C22H14N4

M = 334.37

Monoclinic,

a = 5.0553 (4) Å

b = 17.3437 (10) Å

c = 19.6339 (14) Å

β = 97.653 (5)°

V = 1706.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.45 × 0.09 × 0.04 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.965, T max = 0.997

15641 measured reflections

2906 independent reflections

1490 reflections with I > 2σ(I)

R int = 0.153

Refinement

R[F 2 > 2σ(F 2)] = 0.079

wR(F 2) = 0.169

S = 1.07

2906 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006989/zl2173sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006989/zl2173Isup2.hkl

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

C22H14N4	F(000) = 696
Mr = 334.37	Dx = 1.302 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3931 reflections
a = 5.0553 (4) Å	θ = 2.4–30.2°
b = 17.3437 (10) Å	µ = 0.08 mm−1
c = 19.6339 (14) Å	T = 100 K
β = 97.653 (5)°	Needle, colourless
V = 1706.1 (2) Å3	0.45 × 0.09 × 0.04 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	2906 independent reflections
Radiation source: fine-focus sealed tube	1490 reflections with I > 2σ(I)
graphite	Rint = 0.153
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −6→6
Tmin = 0.965, Tmax = 0.997	k = −20→20
15641 measured reflections	l = −23→22

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.079	H-atom parameters constrained
wR(F2) = 0.169	w = 1/[σ2(Fo2) + (0.0473P)2 + 1.9898P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2906 reflections	Δρmax = 0.26 e Å−3
236 parameters	Δρmin = −0.35 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0124 (18)

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
N1	0.7041 (7)	0.41520 (18)	0.10705 (18)	0.0222 (9)
N2	0.8001 (6)	0.29462 (17)	0.14467 (17)	0.0196 (9)
N3	1.5730 (8)	0.3343 (2)	−0.1704 (2)	0.0366 (11)
N4	0.1768 (8)	−0.0990 (2)	0.05749 (19)	0.0328 (10)
C1	0.5702 (8)	0.3997 (2)	0.1633 (2)	0.0205 (10)
C2	0.3933 (8)	0.4456 (2)	0.1943 (2)	0.0250 (11)
H2A	0.3510	0.4953	0.1787	0.030*
C3	0.2841 (8)	0.4148 (2)	0.2487 (2)	0.0271 (11)
H3A	0.1639	0.4441	0.2697	0.033*
C4	0.3485 (8)	0.3408 (2)	0.2733 (2)	0.0272 (11)
H4A	0.2719	0.3223	0.3105	0.033*
C5	0.5240 (8)	0.2944 (2)	0.2434 (2)	0.0240 (11)
H5A	0.5681	0.2451	0.2597	0.029*
C6	0.6310 (8)	0.3255 (2)	0.1876 (2)	0.0197 (10)
C7	0.8349 (8)	0.3516 (2)	0.0971 (2)	0.0196 (10)
C8	0.9937 (8)	0.3425 (2)	0.0400 (2)	0.0183 (10)
C9	1.0085 (8)	0.2747 (2)	0.0032 (2)	0.0206 (11)
H9A	0.9193	0.2310	0.0153	0.025*
C10	1.1554 (8)	0.2718 (2)	−0.0515 (2)	0.0248 (11)
H10A	1.1656	0.2262	−0.0758	0.030*
C11	1.2870 (8)	0.3372 (2)	−0.0697 (2)	0.0207 (11)
C12	1.2703 (8)	0.4059 (2)	−0.0344 (2)	0.0228 (11)
H12A	1.3561	0.4499	−0.0473	0.027*
C13	1.1248 (8)	0.4079 (2)	0.0200 (2)	0.0229 (11)
H13A	1.1135	0.4538	0.0439	0.027*
C14	0.9363 (8)	0.2212 (2)	0.1570 (2)	0.0221 (11)
H14A	0.9987	0.2167	0.2057	0.026*
H14B	1.0918	0.2209	0.1329	0.026*
C15	0.7667 (8)	0.1513 (2)	0.1346 (2)	0.0193 (10)
C16	0.8439 (8)	0.0795 (2)	0.1615 (2)	0.0232 (11)
H16A	0.9962	0.0751	0.1935	0.028*
C17	0.6958 (8)	0.0145 (2)	0.1410 (2)	0.0256 (11)
H17A	0.7492	−0.0336	0.1589	0.031*
C18	0.4669 (8)	0.0212 (2)	0.0936 (2)	0.0217 (11)
C19	0.3883 (8)	0.0931 (2)	0.0667 (2)	0.0228 (11)
H19A	0.2349	0.0978	0.0351	0.027*
C20	0.5388 (8)	0.1572 (2)	0.0871 (2)	0.0208 (10)
H20A	0.4869	0.2052	0.0687	0.025*
C21	1.4437 (9)	0.3350 (2)	−0.1261 (3)	0.0281 (12)
C22	0.3071 (9)	−0.0458 (2)	0.0734 (2)	0.0256 (11)

	U11	U22	U33	U12	U13	U23
N1	0.028 (2)	0.016 (2)	0.023 (2)	0.0017 (16)	0.0025 (19)	−0.0006 (16)
N2	0.026 (2)	0.0127 (19)	0.019 (2)	0.0003 (15)	0.0024 (18)	−0.0026 (16)
N3	0.043 (3)	0.031 (2)	0.036 (3)	−0.0030 (19)	0.006 (2)	−0.001 (2)
N4	0.045 (3)	0.027 (2)	0.027 (2)	−0.006 (2)	0.006 (2)	−0.0006 (18)
C1	0.026 (2)	0.016 (3)	0.019 (3)	−0.0022 (19)	0.003 (2)	−0.003 (2)
C2	0.029 (3)	0.015 (2)	0.030 (3)	0.003 (2)	0.000 (2)	−0.006 (2)
C3	0.025 (2)	0.031 (3)	0.027 (3)	−0.004 (2)	0.007 (2)	−0.006 (2)
C4	0.032 (3)	0.026 (3)	0.026 (3)	−0.008 (2)	0.008 (2)	−0.006 (2)
C5	0.028 (3)	0.019 (2)	0.024 (3)	−0.003 (2)	−0.002 (2)	−0.003 (2)
C6	0.024 (2)	0.016 (2)	0.018 (3)	−0.0035 (19)	0.001 (2)	−0.005 (2)
C7	0.021 (2)	0.017 (2)	0.019 (3)	−0.0054 (19)	−0.005 (2)	0.000 (2)
C8	0.021 (2)	0.015 (2)	0.019 (3)	0.0019 (18)	0.001 (2)	0.003 (2)
C9	0.023 (2)	0.016 (3)	0.023 (3)	−0.0008 (18)	0.003 (2)	0.004 (2)
C10	0.032 (3)	0.022 (3)	0.019 (3)	0.002 (2)	−0.001 (2)	−0.001 (2)
C11	0.022 (2)	0.021 (3)	0.020 (3)	0.0000 (19)	0.004 (2)	0.005 (2)
C12	0.031 (3)	0.017 (3)	0.021 (3)	−0.0037 (19)	0.004 (2)	−0.002 (2)
C13	0.031 (3)	0.015 (2)	0.022 (3)	0.002 (2)	0.002 (2)	−0.002 (2)
C14	0.023 (2)	0.021 (2)	0.023 (3)	0.0009 (19)	0.003 (2)	0.0011 (19)
C15	0.023 (3)	0.016 (2)	0.019 (3)	0.0013 (18)	0.005 (2)	−0.0030 (19)
C16	0.026 (2)	0.020 (2)	0.024 (3)	−0.001 (2)	0.004 (2)	0.001 (2)
C17	0.026 (3)	0.019 (2)	0.032 (3)	0.003 (2)	0.004 (3)	0.001 (2)
C18	0.026 (3)	0.017 (2)	0.024 (3)	−0.0035 (19)	0.010 (2)	−0.004 (2)
C19	0.021 (2)	0.024 (3)	0.022 (3)	0.000 (2)	0.001 (2)	0.001 (2)
C20	0.027 (3)	0.015 (2)	0.021 (3)	0.0006 (19)	0.004 (2)	−0.0002 (19)
C21	0.035 (3)	0.019 (3)	0.030 (3)	−0.003 (2)	0.003 (3)	0.000 (2)
C22	0.033 (3)	0.023 (3)	0.022 (3)	−0.001 (2)	0.007 (2)	0.002 (2)

N1—C7	1.314 (5)	C10—C11	1.385 (5)
N1—C1	1.397 (5)	C10—H10A	0.9300
N2—C6	1.385 (5)	C11—C12	1.387 (5)
N2—C7	1.387 (5)	C11—C21	1.446 (6)
N2—C14	1.453 (5)	C12—C13	1.376 (5)
N3—C21	1.155 (5)	C12—H12A	0.9300
N4—C22	1.152 (5)	C13—H13A	0.9300
C1—C6	1.391 (5)	C14—C15	1.515 (5)
C1—C2	1.397 (5)	C14—H14A	0.9700
C2—C3	1.375 (6)	C14—H14B	0.9700
C2—H2A	0.9300	C15—C20	1.386 (5)
C3—C4	1.393 (6)	C15—C16	1.388 (5)
C3—H3A	0.9300	C16—C17	1.384 (5)
C4—C5	1.385 (6)	C16—H16A	0.9300
C4—H4A	0.9300	C17—C18	1.390 (5)
C5—C6	1.394 (6)	C17—H17A	0.9300
C5—H5A	0.9300	C18—C19	1.391 (5)
C7—C8	1.472 (6)	C18—C22	1.440 (6)
C8—C9	1.387 (5)	C19—C20	1.377 (5)
C8—C13	1.397 (5)	C19—H19A	0.9300
C9—C10	1.385 (5)	C20—H20A	0.9300
C9—H9A	0.9300
C7—N1—C1	105.2 (3)	C10—C11—C21	120.6 (4)
C6—N2—C7	106.1 (3)	C12—C11—C21	118.8 (4)
C6—N2—C14	123.7 (3)	C13—C12—C11	119.0 (4)
C7—N2—C14	129.6 (3)	C13—C12—H12A	120.5
C6—C1—C2	120.2 (4)	C11—C12—H12A	120.5
C6—C1—N1	109.9 (4)	C12—C13—C8	121.3 (4)
C2—C1—N1	129.8 (4)	C12—C13—H13A	119.3
C3—C2—C1	117.6 (4)	C8—C13—H13A	119.3
C3—C2—H2A	121.2	N2—C14—C15	114.6 (3)
C1—C2—H2A	121.2	N2—C14—H14A	108.6
C2—C3—C4	121.8 (4)	C15—C14—H14A	108.6
C2—C3—H3A	119.1	N2—C14—H14B	108.6
C4—C3—H3A	119.1	C15—C14—H14B	108.6
C5—C4—C3	121.5 (4)	H14A—C14—H14B	107.6
C5—C4—H4A	119.3	C20—C15—C16	119.3 (4)
C3—C4—H4A	119.3	C20—C15—C14	121.6 (3)
C4—C5—C6	116.4 (4)	C16—C15—C14	119.2 (4)
C4—C5—H5A	121.8	C17—C16—C15	120.4 (4)
C6—C5—H5A	121.8	C17—C16—H16A	119.8
N2—C6—C1	106.0 (4)	C15—C16—H16A	119.8
N2—C6—C5	131.6 (4)	C16—C17—C18	119.7 (4)
C1—C6—C5	122.4 (4)	C16—C17—H17A	120.1
N1—C7—N2	112.7 (4)	C18—C17—H17A	120.1
N1—C7—C8	122.6 (4)	C17—C18—C19	120.0 (4)
N2—C7—C8	124.6 (4)	C17—C18—C22	120.2 (4)
C9—C8—C13	118.8 (4)	C19—C18—C22	119.8 (4)
C9—C8—C7	124.0 (4)	C20—C19—C18	119.6 (4)
C13—C8—C7	117.1 (4)	C20—C19—H19A	120.2
C10—C9—C8	120.4 (4)	C18—C19—H19A	120.2
C10—C9—H9A	119.8	C19—C20—C15	120.9 (4)
C8—C9—H9A	119.8	C19—C20—H20A	119.6
C9—C10—C11	119.8 (4)	C15—C20—H20A	119.6
C9—C10—H10A	120.1	N3—C21—C11	178.5 (5)
C11—C10—H10A	120.1	N4—C22—C18	179.2 (5)
C10—C11—C12	120.7 (4)
C7—N1—C1—C6	1.5 (4)	N2—C7—C8—C13	−147.4 (4)
C7—N1—C1—C2	−177.1 (4)	C13—C8—C9—C10	1.3 (6)
C6—C1—C2—C3	−0.1 (6)	C7—C8—C9—C10	177.7 (4)
N1—C1—C2—C3	178.4 (4)	C8—C9—C10—C11	−0.3 (6)
C1—C2—C3—C4	0.9 (6)	C9—C10—C11—C12	−0.9 (6)
C2—C3—C4—C5	−0.7 (6)	C9—C10—C11—C21	179.3 (4)
C3—C4—C5—C6	−0.3 (6)	C10—C11—C12—C13	1.2 (6)
C7—N2—C6—C1	0.4 (4)	C21—C11—C12—C13	−179.0 (4)
C14—N2—C6—C1	172.4 (3)	C11—C12—C13—C8	−0.2 (6)
C7—N2—C6—C5	178.7 (4)	C9—C8—C13—C12	−1.0 (6)
C14—N2—C6—C5	−9.3 (6)	C7—C8—C13—C12	−177.7 (4)
C2—C1—C6—N2	177.5 (3)	C6—N2—C14—C15	81.2 (5)
N1—C1—C6—N2	−1.2 (4)	C7—N2—C14—C15	−108.9 (4)
C2—C1—C6—C5	−1.0 (6)	N2—C14—C15—C20	20.2 (5)
N1—C1—C6—C5	−179.7 (4)	N2—C14—C15—C16	−160.9 (4)
C4—C5—C6—N2	−177.0 (4)	C20—C15—C16—C17	0.2 (6)
C4—C5—C6—C1	1.1 (6)	C14—C15—C16—C17	−178.7 (4)
C1—N1—C7—N2	−1.3 (4)	C15—C16—C17—C18	−0.6 (6)
C1—N1—C7—C8	177.1 (3)	C16—C17—C18—C19	0.4 (6)
C6—N2—C7—N1	0.5 (4)	C16—C17—C18—C22	−178.2 (4)
C14—N2—C7—N1	−170.8 (4)	C17—C18—C19—C20	0.2 (6)
C6—N2—C7—C8	−177.8 (4)	C22—C18—C19—C20	178.7 (4)
C14—N2—C7—C8	10.9 (6)	C18—C19—C20—C15	−0.6 (6)
N1—C7—C8—C9	−142.1 (4)	C16—C15—C20—C19	0.3 (6)
N2—C7—C8—C9	36.1 (6)	C14—C15—C20—C19	179.3 (4)
N1—C7—C8—C13	34.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···N1i	0.93	2.62	3.425 (5)	146
C19—H19A···N4ii	0.93	2.57	3.502 (6)	175
C9—H9A···N4iii	0.93	2.71	3.361 (5)	128
C14—H14A···N3iv	0.97	2.57	3.502 (5)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯N1i	0.93	2.62	3.425 (5)	146
C19—H19A⋯N4ii	0.93	2.57	3.502 (6)	175
C9—H9A⋯N4iii	0.93	2.71	3.361 (5)	128
C14—H14A⋯N3iv	0.97	2.57	3.502 (5)	162

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