5,6-Dimethyl-2-(pyridin-2-yl)-1-[(pyri-din-2-yl)meth-yl]-1H-benzimidazole.

The title compound, C20H18N4, was obtained via the condensation of 4,5-di-methyl-benzene-1,2-di-amine with pyridine-2-carbaldehyde. The plane of the 2-(pyridin-2-yl) substitutent is canted by 2.75 (11)° from the plane of the benzimidazole system. The mol-ecule exhibits an S(6) C-H⋯N intra-molecular hydrogen-bond motif. In the crystal, C-H⋯N hydrogen bonds link pairs of mol-ecules related by a crystallographic inversion center, forming R 2 (2)(20) rings. Additional weak C-H⋯N hydrogen bonds result in C(9) chains parallel to [001].

Related literature

Reich et al. (2004 ▶) provide examples of inter­molecular aldimine coupling. For a discussion of the biological activity of benzimidazole derivatives, see: López-Rodríguez et al. (1999 ▶); Horton et al. (2003 ▶). For the structure of 2-(pyridin-4-yl)-1H-benzimidazole, see: Geiger & Bond (2013 ▶), and for its trihydrate, see: Huang et al. (2004 ▶). For the structure of 5,6-di­methyl­benzimidazole, see: Lee & Scheidt (1986 ▶).

Experimental

Crystal data

C20H18N4

M = 314.38

Monoclinic,

a = 35.544 (4) Å

b = 6.1194 (5) Å

c = 16.5050 (19) Å

β = 113.273 (4)°

V = 3297.9 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 200 K

0.60 × 0.30 × 0.06 mm

Data collection

Bruker SMART X2S benchtop diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.45, T max = 1.00

8660 measured reflections

3501 independent reflections

2402 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.154

S = 1.03

3501 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814003870/fk2079sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814003870/fk2079Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814003870/fk2079Isup3.mol

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814003870/fk2079Isup4.cml

CCDC reference: 987895

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

C20H18N4	F(000) = 1328
Mr = 314.38	Dx = 1.266 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 35.544 (4) Å	Cell parameters from 3800 reflections
b = 6.1194 (5) Å	θ = 2.5–26.8°
c = 16.5050 (19) Å	µ = 0.08 mm−1
β = 113.273 (4)°	T = 200 K
V = 3297.9 (6) Å3	Prism, colourless
Z = 8	0.60 × 0.30 × 0.06 mm

Bruker SMART X2S benchtop diffractometer	3501 independent reflections
Radiation source: XOS X-beam microfocus source	2402 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.061
Detector resolution: 8.3330 pixels mm-1	θmax = 27.1°, θmin = 2.5°
ω scans	h = −45→45
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −7→6
Tmin = 0.45, Tmax = 1.00	l = −21→21
8660 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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0585P)2 + 1.1674P] where P = (Fo2 + 2Fc2)/3
3501 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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	0.12573 (5)	0.1608 (2)	0.70519 (10)	0.0282 (4)
N2	0.12580 (5)	0.4886 (3)	0.76699 (11)	0.0310 (4)
N3	0.03658 (5)	0.2057 (3)	0.61214 (13)	0.0482 (5)
N4	0.11122 (5)	−0.1414 (3)	0.50291 (12)	0.0366 (4)
C1	0.16607 (6)	0.2056 (3)	0.76024 (13)	0.0289 (4)
C2	0.16544 (6)	0.4083 (3)	0.79875 (13)	0.0298 (4)
C3	0.20184 (6)	0.4972 (3)	0.85981 (14)	0.0345 (5)
H3	0.2016	0.635	0.8861	0.041*
C4	0.23817 (6)	0.3845 (3)	0.88192 (14)	0.0342 (5)
C5	0.23848 (6)	0.1778 (3)	0.84098 (14)	0.0355 (5)
C6	0.20272 (6)	0.0883 (3)	0.78064 (14)	0.0335 (5)
H6	0.2029	−0.0487	0.7537	0.04*
C7	0.10284 (6)	0.3384 (3)	0.71141 (13)	0.0299 (4)
C8	0.05821 (6)	0.3659 (3)	0.66471 (14)	0.0333 (5)
C9	0.04023 (7)	0.5580 (4)	0.67726 (17)	0.0437 (6)
H9	0.0565	0.6686	0.7156	0.052*
C10	−0.00146 (7)	0.5856 (4)	0.63336 (18)	0.0517 (6)
H10	−0.0143	0.7159	0.6407	0.062*
C11	−0.02436 (7)	0.4211 (4)	0.57853 (17)	0.0524 (6)
H11	−0.0531	0.4356	0.5475	0.063*
C12	−0.00429 (7)	0.2366 (4)	0.57030 (18)	0.0554 (7)
H12	−0.0201	0.1234	0.5329	0.067*
C13	0.11412 (6)	−0.0225 (3)	0.64333 (13)	0.0310 (4)
H13A	0.0858	−0.0675	0.6326	0.037*
H13B	0.1324	−0.1478	0.6704	0.037*
C14	0.11648 (5)	0.0312 (3)	0.55631 (12)	0.0254 (4)
C15	0.12293 (6)	0.2405 (3)	0.53268 (13)	0.0315 (5)
H15	0.1266	0.3593	0.5721	0.038*
C16	0.12391 (6)	0.2736 (3)	0.45063 (15)	0.0371 (5)
H16	0.1286	0.4156	0.4332	0.045*
C17	0.11803 (7)	0.0989 (3)	0.39455 (14)	0.0399 (5)
H17	0.1183	0.1176	0.3377	0.048*
C18	0.11168 (8)	−0.1032 (4)	0.42288 (15)	0.0451 (6)
H18	0.1074	−0.2233	0.3838	0.054*
C41	0.27737 (6)	0.4761 (4)	0.94972 (17)	0.0465 (6)
H41A	0.2716	0.6146	0.9724	0.07*
H41B	0.297	0.5013	0.9224	0.07*
H41C	0.289	0.372	0.9984	0.07*
C51	0.27837 (7)	0.0560 (4)	0.86530 (17)	0.0480 (6)
H51A	0.2736	−0.0797	0.8311	0.072*
H51B	0.2896	0.0213	0.9284	0.072*
H51C	0.2979	0.1472	0.8522	0.072*

	U11	U22	U33	U12	U13	U23
N1	0.0317 (8)	0.0268 (9)	0.0281 (9)	−0.0039 (7)	0.0139 (7)	−0.0029 (7)
N2	0.0330 (8)	0.0303 (9)	0.0319 (10)	−0.0014 (7)	0.0151 (7)	−0.0027 (7)
N3	0.0370 (10)	0.0491 (12)	0.0518 (13)	−0.0056 (9)	0.0103 (9)	−0.0130 (10)
N4	0.0512 (10)	0.0269 (9)	0.0325 (10)	−0.0042 (8)	0.0173 (8)	−0.0045 (8)
C1	0.0338 (10)	0.0298 (11)	0.0237 (10)	−0.0032 (8)	0.0119 (8)	0.0023 (8)
C2	0.0323 (10)	0.0297 (11)	0.0298 (11)	−0.0004 (8)	0.0148 (8)	0.0025 (8)
C3	0.0363 (10)	0.0311 (11)	0.0375 (13)	−0.0045 (9)	0.0161 (9)	−0.0048 (9)
C4	0.0360 (11)	0.0357 (11)	0.0319 (12)	−0.0044 (9)	0.0143 (9)	0.0024 (9)
C5	0.0366 (11)	0.0362 (12)	0.0358 (12)	0.0027 (9)	0.0165 (9)	0.0086 (10)
C6	0.0413 (11)	0.0270 (10)	0.0348 (12)	0.0028 (9)	0.0177 (9)	0.0015 (9)
C7	0.0347 (10)	0.0313 (11)	0.0267 (11)	−0.0021 (8)	0.0155 (8)	0.0003 (9)
C8	0.0333 (10)	0.0379 (12)	0.0298 (11)	−0.0050 (9)	0.0138 (9)	0.0002 (9)
C9	0.0394 (12)	0.0399 (13)	0.0543 (15)	−0.0011 (10)	0.0210 (11)	−0.0060 (11)
C10	0.0393 (12)	0.0505 (14)	0.0666 (18)	0.0025 (11)	0.0224 (12)	−0.0015 (13)
C11	0.0298 (11)	0.0626 (16)	0.0607 (17)	−0.0003 (11)	0.0134 (11)	0.0003 (13)
C12	0.0367 (12)	0.0593 (16)	0.0602 (18)	−0.0044 (11)	0.0082 (11)	−0.0119 (13)
C13	0.0401 (10)	0.0241 (10)	0.0303 (11)	−0.0057 (8)	0.0154 (9)	−0.0039 (8)
C14	0.0222 (8)	0.0240 (10)	0.0284 (10)	0.0005 (7)	0.0084 (7)	−0.0018 (8)
C15	0.0380 (10)	0.0244 (10)	0.0346 (12)	−0.0002 (8)	0.0169 (9)	−0.0002 (8)
C16	0.0465 (12)	0.0291 (11)	0.0415 (13)	0.0054 (9)	0.0236 (10)	0.0082 (9)
C17	0.0543 (13)	0.0425 (13)	0.0284 (12)	0.0073 (10)	0.0222 (10)	0.0047 (10)
C18	0.0663 (15)	0.0369 (12)	0.0358 (13)	0.0026 (11)	0.0241 (11)	−0.0092 (10)
C41	0.0340 (11)	0.0510 (14)	0.0512 (15)	−0.0066 (10)	0.0135 (11)	−0.0021 (11)
C51	0.0426 (12)	0.0496 (14)	0.0510 (16)	0.0097 (11)	0.0174 (11)	0.0069 (12)

N1—C7	1.385 (2)	C10—C11	1.383 (4)
N1—C1	1.388 (2)	C10—H10	0.95
N1—C13	1.462 (2)	C11—C12	1.371 (3)
N2—C7	1.327 (2)	C11—H11	0.95
N2—C2	1.385 (2)	C12—H12	0.95
N3—C8	1.333 (3)	C13—C14	1.508 (3)
N3—C12	1.353 (3)	C13—H13A	0.99
N4—C14	1.341 (2)	C13—H13B	0.99
N4—C18	1.348 (3)	C14—C15	1.384 (3)
C1—C2	1.398 (3)	C15—C16	1.383 (3)
C1—C6	1.407 (3)	C15—H15	0.95
C2—C3	1.398 (3)	C16—C17	1.375 (3)
C3—C4	1.380 (3)	C16—H16	0.95
C3—H3	0.95	C17—C18	1.372 (3)
C4—C5	1.436 (3)	C17—H17	0.95
C4—C41	1.509 (3)	C18—H18	0.95
C5—C6	1.381 (3)	C41—H41A	0.98
C5—C51	1.509 (3)	C41—H41B	0.98
C6—H6	0.95	C41—H41C	0.98
C7—C8	1.474 (3)	C51—H51A	0.98
C8—C9	1.392 (3)	C51—H51B	0.98
C9—C10	1.379 (3)	C51—H51C	0.98
C9—H9	0.95
C7—N1—C1	106.36 (15)	C10—C11—H11	121.0
C7—N1—C13	129.91 (17)	N3—C12—C11	124.1 (2)
C1—N1—C13	122.81 (16)	N3—C12—H12	118.0
C7—N2—C2	105.77 (16)	C11—C12—H12	118.0
C8—N3—C12	117.1 (2)	N1—C13—C14	113.04 (15)
C14—N4—C18	117.07 (17)	N1—C13—H13A	109.0
N1—C1—C2	105.94 (16)	C14—C13—H13A	109.0
N1—C1—C6	132.48 (18)	N1—C13—H13B	109.0
C2—C1—C6	121.58 (18)	C14—C13—H13B	109.0
N2—C2—C1	109.84 (17)	H13A—C13—H13B	107.8
N2—C2—C3	130.41 (18)	N4—C14—C15	122.64 (17)
C1—C2—C3	119.75 (17)	N4—C14—C13	114.13 (16)
C4—C3—C2	119.94 (19)	C15—C14—C13	123.22 (16)
C4—C3—H3	120.0	C16—C15—C14	118.86 (18)
C2—C3—H3	120.0	C16—C15—H15	120.6
C3—C4—C5	119.74 (19)	C14—C15—H15	120.6
C3—C4—C41	120.26 (19)	C17—C16—C15	119.26 (18)
C5—C4—C41	119.99 (18)	C17—C16—H16	120.4
C6—C5—C4	120.85 (18)	C15—C16—H16	120.4
C6—C5—C51	119.74 (19)	C18—C17—C16	118.25 (19)
C4—C5—C51	119.41 (19)	C18—C17—H17	120.9
C5—C6—C1	118.13 (18)	C16—C17—H17	120.9
C5—C6—H6	120.9	N4—C18—C17	123.9 (2)
C1—C6—H6	120.9	N4—C18—H18	118.1
N2—C7—N1	112.07 (17)	C17—C18—H18	118.1
N2—C7—C8	121.56 (17)	C4—C41—H41A	109.5
N1—C7—C8	126.37 (18)	C4—C41—H41B	109.5
N3—C8—C9	122.5 (2)	H41A—C41—H41B	109.5
N3—C8—C7	118.75 (18)	C4—C41—H41C	109.5
C9—C8—C7	118.74 (19)	H41A—C41—H41C	109.5
C10—C9—C8	119.1 (2)	H41B—C41—H41C	109.5
C10—C9—H9	120.4	C5—C51—H51A	109.5
C8—C9—H9	120.4	C5—C51—H51B	109.5
C9—C10—C11	119.2 (2)	H51A—C51—H51B	109.5
C9—C10—H10	120.4	C5—C51—H51C	109.5
C11—C10—H10	120.4	H51A—C51—H51C	109.5
C12—C11—C10	118.0 (2)	H51B—C51—H51C	109.5
C12—C11—H11	121.0
C7—N1—C1—C2	1.14 (19)	C1—N1—C7—C8	180.00 (18)
C13—N1—C1—C2	171.16 (16)	C13—N1—C7—C8	10.9 (3)
C7—N1—C1—C6	−179.63 (19)	C12—N3—C8—C9	0.1 (3)
C13—N1—C1—C6	−9.6 (3)	C12—N3—C8—C7	−179.9 (2)
C7—N2—C2—C1	0.6 (2)	N2—C7—C8—N3	−177.59 (18)
C7—N2—C2—C3	−179.1 (2)	N1—C7—C8—N3	1.5 (3)
N1—C1—C2—N2	−1.1 (2)	N2—C7—C8—C9	2.3 (3)
C6—C1—C2—N2	179.58 (17)	N1—C7—C8—C9	−178.59 (18)
N1—C1—C2—C3	178.63 (18)	N3—C8—C9—C10	−0.5 (3)
C6—C1—C2—C3	−0.7 (3)	C7—C8—C9—C10	179.6 (2)
N2—C2—C3—C4	179.53 (19)	C8—C9—C10—C11	0.5 (4)
C1—C2—C3—C4	−0.1 (3)	C9—C10—C11—C12	−0.1 (4)
C2—C3—C4—C5	1.0 (3)	C8—N3—C12—C11	0.3 (4)
C2—C3—C4—C41	−178.20 (19)	C10—C11—C12—N3	−0.3 (4)
C3—C4—C5—C6	−1.0 (3)	C7—N1—C13—C14	82.2 (2)
C41—C4—C5—C6	178.14 (19)	C1—N1—C13—C14	−85.3 (2)
C3—C4—C5—C51	179.78 (19)	C18—N4—C14—C15	−1.2 (3)
C41—C4—C5—C51	−1.1 (3)	C18—N4—C14—C13	177.96 (18)
C4—C5—C6—C1	0.2 (3)	N1—C13—C14—N4	171.72 (16)
C51—C5—C6—C1	179.41 (18)	N1—C13—C14—C15	−9.1 (3)
N1—C1—C6—C5	−178.49 (19)	N4—C14—C15—C16	0.2 (3)
C2—C1—C6—C5	0.6 (3)	C13—C14—C15—C16	−178.92 (18)
C2—N2—C7—N1	0.2 (2)	C14—C15—C16—C17	0.7 (3)
C2—N2—C7—C8	179.37 (17)	C15—C16—C17—C18	−0.5 (3)
C1—N1—C7—N2	−0.8 (2)	C14—N4—C18—C17	1.4 (3)
C13—N1—C7—N2	−169.90 (17)	C16—C17—C18—N4	−0.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···N3	0.99	2.35	2.948 (3)	118
C11—H11···N4i	0.95	2.61	3.315 (3)	131
C17—H17···N2ii	0.95	2.74	3.368 (3)	125

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯N3	0.99	2.35	2.948 (3)	118
C11—H11⋯N4i	0.95	2.61	3.315 (3)	131
C17—H17⋯N2ii	0.95	2.74	3.368 (3)	125

Symmetry codes: (i) ; (ii) .