1-(2,3,4,5,6-Penta-methyl-benz-yl)-2-(pyridin-2-yl)-1H-benzimidazole.

In the title compound, C24H25N3, the benzimidazole ring system is essentially planar, with an r.m.s. deviation of 0.017 Å, and forms dihedral angles of 7.81 (5) and 87.61 (4)° with the pyridine and benzene rings, respectively. An intra-molecular C-H⋯N hydrogen bond is observed. In the crystal, mol-ecules are stacked along the a axis by weak C-H⋯π inter-actions.

Related literature

For the use of 2-(2-pyrid­yl)benzimidazole in coordination chemistry, see: Sahin et al. (2010 ▶); Harkins et al. (1956 ▶); Chiswell et al. (1964 ▶); De Castro et al. (1991 ▶); Maekawa et al. (1994 ▶); Khalil et al. (2001 ▶); Boca et al. (1997 ▶). For the use of N—N-type ligand systems involving 2,2′-bi­pyridine, see: Lippert (1999 ▶); Wong & Giandomenico (1999 ▶), Kelland & Farrell (2000 ▶). For related structures, see: Çelik et al. (2007 ▶, 2009 ▶, 2014 ▶).

Experimental

Crystal data

C24H25N3

M = 355.47

Monoclinic,

a = 5.3470 (3) Å

b = 21.0622 (12) Å

c = 17.0379 (9) Å

β = 97.699 (3)°

V = 1901.50 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 296 K

0.25 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.982, T max = 0.989

25354 measured reflections

3741 independent reflections

3056 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.150

S = 1.04

3741 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.24 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: SHELXL2013 (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/S1600536814007934/rz5115sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814007934/rz5115Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814007934/rz5115Isup3.cml

CCDC reference: 996309

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

C24H25N3	F(000) = 760
Mr = 355.47	Dx = 1.242 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 5.3470 (3) Å	Cell parameters from 1276 reflections
b = 21.0622 (12) Å	θ = 2.3–31.5°
c = 17.0379 (9) Å	µ = 0.07 mm−1
β = 97.699 (3)°	T = 296 K
V = 1901.50 (18) Å3	Prism, yellow
Z = 4	0.25 × 0.20 × 0.15 mm

Bruker APEXII CCD diffractometer	3056 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
φ and ω scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (Blessing, 1995)	h = −6→6
Tmin = 0.982, Tmax = 0.989	k = −25→25
25354 measured reflections	l = −21→20
3741 independent 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0775P)2 + 0.5927P] where P = (Fo2 + 2Fc2)/3
3741 reflections	(Δ/σ)max < 0.001
254 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.17 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.

	x	y	z	Uiso*/Ueq
C1	1.0873 (5)	0.86580 (11)	0.44231 (14)	0.0724 (6)
H1	1.2174	0.8428	0.4246	0.087*
C2	1.0060 (5)	0.91952 (12)	0.40152 (14)	0.0737 (6)
H2	1.0790	0.9327	0.3577	0.088*
C3	0.8151 (5)	0.95308 (12)	0.42706 (16)	0.0842 (7)
H3	0.7548	0.9900	0.4011	0.101*
C4	0.7133 (5)	0.93151 (10)	0.49165 (15)	0.0771 (7)
H4	0.5809	0.9535	0.5094	0.092*
C5	0.8068 (3)	0.87716 (7)	0.53054 (11)	0.0465 (4)
C6	0.6926 (3)	0.85653 (7)	0.60059 (10)	0.0452 (4)
C7	0.4595 (4)	0.86110 (8)	0.69313 (11)	0.0507 (4)
C8	0.2891 (4)	0.87790 (10)	0.74483 (13)	0.0658 (6)
H8	0.2014	0.9161	0.7387	0.079*
C9	0.2541 (4)	0.83708 (10)	0.80460 (13)	0.0667 (6)
H9	0.1414	0.8477	0.8396	0.080*
C10	0.3850 (4)	0.77962 (10)	0.81392 (12)	0.0598 (5)
H10	0.3597	0.7531	0.8558	0.072*
C11	0.5507 (4)	0.76104 (9)	0.76284 (10)	0.0505 (4)
H11	0.6360	0.7225	0.7690	0.061*
C12	0.5841 (3)	0.80251 (8)	0.70185 (10)	0.0432 (4)
C13	0.8894 (3)	0.74472 (7)	0.62583 (10)	0.0422 (4)
H13A	1.0264	0.7410	0.6691	0.051*
H13B	0.9632	0.7525	0.5777	0.051*
C14	0.7459 (3)	0.68215 (7)	0.61734 (9)	0.0370 (4)
C15	0.5434 (3)	0.67529 (7)	0.55618 (9)	0.0391 (4)
C16	0.4047 (3)	0.61901 (8)	0.54888 (10)	0.0452 (4)
C17	0.4753 (3)	0.56796 (8)	0.59946 (11)	0.0471 (4)
C18	0.6838 (3)	0.57318 (7)	0.65801 (10)	0.0448 (4)
C19	0.8190 (3)	0.63066 (7)	0.66771 (10)	0.0412 (4)
C20	0.4783 (4)	0.72858 (9)	0.49769 (10)	0.0511 (4)
H20A	0.406 (3)	0.7111 (2)	0.4472 (7)	0.077*
H20B	0.630 (2)	0.7521 (5)	0.4912 (6)	0.077*
H20C	0.357 (2)	0.7567 (5)	0.5172 (5)	0.077*
C21	0.1762 (4)	0.61342 (11)	0.48609 (14)	0.0703 (6)
H21A	0.2254 (10)	0.5965 (8)	0.4399 (8)	0.105*
H21B	0.106 (2)	0.6535 (6)	0.4754 (8)	0.105*
H21C	0.057 (2)	0.5868 (8)	0.5043 (5)	0.105*
C22	0.3235 (5)	0.50692 (10)	0.59025 (15)	0.0710 (6)
H22A	0.314 (3)	0.4923 (5)	0.5373 (9)	0.107*
H22B	0.158 (3)	0.5146 (2)	0.6025 (10)	0.107*
H22C	0.403 (2)	0.4757 (5)	0.6251 (9)	0.107*
C23	0.7616 (5)	0.51661 (9)	0.71064 (13)	0.0655 (6)
H23A	0.626 (2)	0.5047 (5)	0.7383 (8)	0.098*
H23B	0.904 (3)	0.5276 (3)	0.7476 (8)	0.098*
H23C	0.803 (3)	0.4820 (6)	0.6790 (5)	0.098*
C24	1.0435 (4)	0.63574 (10)	0.73176 (13)	0.0630 (5)
H24A	1.168 (2)	0.6592 (7)	0.7134 (4)	0.094*
H24B	1.104 (2)	0.5960 (6)	0.7452 (7)	0.094*
H24C	0.9950 (10)	0.6551 (7)	0.7754 (7)	0.094*
N1	0.9926 (3)	0.84413 (8)	0.50574 (10)	0.0616 (4)
N2	0.5315 (3)	0.89400 (7)	0.63031 (10)	0.0561 (4)
N3	0.7309 (3)	0.79969 (6)	0.64092 (8)	0.0406 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0797 (15)	0.0651 (13)	0.0780 (14)	0.0052 (11)	0.0312 (12)	0.0205 (11)
C2	0.0844 (16)	0.0737 (14)	0.0641 (13)	−0.0104 (12)	0.0138 (12)	0.0232 (11)
C3	0.1041 (19)	0.0620 (14)	0.0871 (17)	0.0111 (13)	0.0152 (15)	0.0351 (13)
C4	0.0940 (17)	0.0516 (12)	0.0889 (16)	0.0184 (11)	0.0244 (14)	0.0216 (11)
C5	0.0539 (10)	0.0329 (8)	0.0517 (10)	−0.0066 (7)	0.0031 (8)	0.0006 (7)
C6	0.0522 (10)	0.0305 (8)	0.0519 (10)	−0.0019 (7)	0.0034 (8)	−0.0032 (7)
C7	0.0580 (11)	0.0396 (9)	0.0551 (10)	−0.0025 (8)	0.0099 (9)	−0.0119 (8)
C8	0.0756 (14)	0.0522 (11)	0.0726 (13)	0.0050 (10)	0.0212 (11)	−0.0188 (10)
C9	0.0737 (14)	0.0657 (13)	0.0651 (13)	−0.0053 (11)	0.0261 (11)	−0.0210 (11)
C10	0.0732 (13)	0.0590 (11)	0.0490 (10)	−0.0122 (10)	0.0152 (9)	−0.0084 (9)
C11	0.0582 (11)	0.0457 (9)	0.0476 (10)	−0.0050 (8)	0.0070 (8)	−0.0042 (7)
C12	0.0451 (9)	0.0397 (8)	0.0442 (9)	−0.0072 (7)	0.0038 (7)	−0.0087 (7)
C13	0.0405 (9)	0.0345 (8)	0.0514 (9)	0.0012 (6)	0.0059 (7)	0.0014 (7)
C14	0.0395 (8)	0.0319 (7)	0.0407 (8)	0.0008 (6)	0.0096 (6)	−0.0031 (6)
C15	0.0416 (8)	0.0382 (8)	0.0389 (8)	0.0030 (6)	0.0108 (7)	−0.0045 (6)
C16	0.0441 (9)	0.0449 (9)	0.0479 (9)	−0.0036 (7)	0.0108 (7)	−0.0122 (7)
C17	0.0536 (10)	0.0381 (9)	0.0538 (10)	−0.0077 (7)	0.0227 (8)	−0.0116 (7)
C18	0.0574 (10)	0.0339 (8)	0.0473 (9)	0.0041 (7)	0.0230 (8)	−0.0003 (7)
C19	0.0453 (9)	0.0367 (8)	0.0426 (8)	0.0044 (7)	0.0094 (7)	0.0000 (6)
C20	0.0573 (11)	0.0504 (10)	0.0441 (9)	0.0048 (8)	0.0010 (8)	0.0003 (8)
C21	0.0589 (12)	0.0747 (14)	0.0738 (14)	−0.0118 (11)	−0.0033 (11)	−0.0163 (11)
C22	0.0808 (15)	0.0505 (11)	0.0862 (15)	−0.0231 (10)	0.0274 (12)	−0.0111 (10)
C23	0.0940 (16)	0.0398 (10)	0.0665 (13)	0.0052 (10)	0.0247 (11)	0.0093 (9)
C24	0.0675 (13)	0.0540 (11)	0.0624 (12)	0.0037 (9)	−0.0094 (10)	0.0093 (9)
N1	0.0691 (10)	0.0521 (9)	0.0671 (10)	0.0057 (8)	0.0216 (8)	0.0180 (8)
N2	0.0697 (10)	0.0346 (7)	0.0650 (10)	0.0040 (7)	0.0129 (8)	−0.0039 (7)
N3	0.0456 (7)	0.0305 (6)	0.0455 (7)	−0.0029 (5)	0.0056 (6)	−0.0021 (5)

C1—N1	1.334 (3)	C13—H13B	0.9700
C1—C2	1.368 (3)	C14—C19	1.405 (2)
C1—H1	0.9300	C14—C15	1.406 (2)
C2—C3	1.360 (4)	C15—C16	1.395 (2)
C2—H2	0.9300	C15—C20	1.510 (2)
C3—C4	1.369 (3)	C16—C17	1.398 (3)
C3—H3	0.9300	C16—C21	1.517 (3)
C4—C5	1.382 (3)	C17—C18	1.397 (3)
C4—H4	0.9300	C17—C22	1.517 (2)
C5—N1	1.328 (2)	C18—C19	1.408 (2)
C5—C6	1.477 (3)	C18—C23	1.515 (2)
C6—N2	1.319 (2)	C19—C24	1.514 (3)
C6—N3	1.382 (2)	C20—H20A	0.968 (12)
C7—N2	1.373 (2)	C20—H20B	0.968 (13)
C7—C8	1.395 (3)	C20—H20C	0.968 (12)
C7—C12	1.401 (2)	C21—H21A	0.933 (14)
C8—C9	1.365 (3)	C21—H21B	0.933 (14)
C8—H8	0.9300	C21—H21C	0.933 (14)
C9—C10	1.396 (3)	C22—H22A	0.948 (14)
C9—H9	0.9300	C22—H22B	0.948 (14)
C10—C11	1.379 (3)	C22—H22C	0.948 (14)
C10—H10	0.9300	C23—H23A	0.951 (14)
C11—C12	1.387 (2)	C23—H23B	0.951 (14)
C11—H11	0.9300	C23—H23C	0.951 (13)
C12—N3	1.384 (2)	C24—H24A	0.915 (14)
C13—N3	1.478 (2)	C24—H24B	0.915 (13)
C13—C14	1.522 (2)	C24—H24C	0.915 (13)
C13—H13A	0.9700
N1—C1—C2	124.4 (2)	C15—C16—C17	120.14 (16)
N1—C1—H1	117.8	C15—C16—C21	119.82 (17)
C2—C1—H1	117.8	C17—C16—C21	120.05 (16)
C3—C2—C1	117.9 (2)	C18—C17—C16	120.23 (15)
C3—C2—H2	121.0	C18—C17—C22	120.34 (17)
C1—C2—H2	121.0	C16—C17—C22	119.42 (18)
C2—C3—C4	118.7 (2)	C17—C18—C19	119.95 (15)
C2—C3—H3	120.6	C17—C18—C23	119.35 (16)
C4—C3—H3	120.6	C19—C18—C23	120.69 (17)
C3—C4—C5	120.2 (2)	C14—C19—C18	119.69 (15)
C3—C4—H4	119.9	C14—C19—C24	120.95 (15)
C5—C4—H4	119.9	C18—C19—C24	119.35 (15)
N1—C5—C4	121.30 (19)	C15—C20—H20A	109.5
N1—C5—C6	120.74 (15)	C15—C20—H20B	109.5
C4—C5—C6	117.96 (18)	H20A—C20—H20B	109.5
N2—C6—N3	112.86 (16)	C15—C20—H20C	109.5
N2—C6—C5	119.77 (15)	H20A—C20—H20C	109.5
N3—C6—C5	127.37 (15)	H20B—C20—H20C	109.5
N2—C7—C8	129.74 (18)	C16—C21—H21A	109.5
N2—C7—C12	110.39 (16)	C16—C21—H21B	109.5
C8—C7—C12	119.87 (18)	H21A—C21—H21B	109.5
C9—C8—C7	118.6 (2)	C16—C21—H21C	109.5
C9—C8—H8	120.7	H21A—C21—H21C	109.5
C7—C8—H8	120.7	H21B—C21—H21C	109.5
C8—C9—C10	120.93 (19)	C17—C22—H22A	109.5
C8—C9—H9	119.5	C17—C22—H22B	109.5
C10—C9—H9	119.5	H22A—C22—H22B	109.5
C11—C10—C9	121.92 (19)	C17—C22—H22C	109.5
C11—C10—H10	119.0	H22A—C22—H22C	109.5
C9—C10—H10	119.0	H22B—C22—H22C	109.5
C10—C11—C12	116.88 (18)	C18—C23—H23A	109.5
C10—C11—H11	121.6	C18—C23—H23B	109.5
C12—C11—H11	121.6	H23A—C23—H23B	109.5
N3—C12—C11	132.66 (16)	C18—C23—H23C	109.5
N3—C12—C7	105.53 (15)	H23A—C23—H23C	109.5
C11—C12—C7	121.80 (17)	H23B—C23—H23C	109.5
N3—C13—C14	113.67 (13)	C19—C24—H24A	109.5
N3—C13—H13A	108.8	C19—C24—H24B	109.5
C14—C13—H13A	108.8	H24A—C24—H24B	109.5
N3—C13—H13B	108.8	C19—C24—H24C	109.5
C14—C13—H13B	108.8	H24A—C24—H24C	109.5
H13A—C13—H13B	107.7	H24B—C24—H24C	109.5
C19—C14—C15	119.78 (14)	C5—N1—C1	117.39 (17)
C19—C14—C13	120.99 (14)	C6—N2—C7	105.26 (15)
C15—C14—C13	119.19 (14)	C6—N3—C12	105.94 (13)
C16—C15—C14	120.06 (15)	C6—N3—C13	129.98 (14)
C16—C15—C20	119.99 (15)	C12—N3—C13	124.08 (13)
C14—C15—C20	119.95 (14)
N1—C1—C2—C3	−0.2 (4)	C15—C16—C17—C22	−179.52 (16)
C1—C2—C3—C4	−0.3 (4)	C21—C16—C17—C22	0.7 (3)
C2—C3—C4—C5	1.0 (4)	C16—C17—C18—C19	1.9 (2)
C3—C4—C5—N1	−1.2 (4)	C22—C17—C18—C19	−178.06 (16)
C3—C4—C5—C6	179.1 (2)	C16—C17—C18—C23	−178.23 (16)
N1—C5—C6—N2	171.36 (17)	C22—C17—C18—C23	1.8 (2)
C4—C5—C6—N2	−9.0 (3)	C15—C14—C19—C18	−1.9 (2)
N1—C5—C6—N3	−9.7 (3)	C13—C14—C19—C18	−179.49 (14)
C4—C5—C6—N3	169.96 (19)	C15—C14—C19—C24	177.28 (16)
N2—C7—C8—C9	−178.4 (2)	C13—C14—C19—C24	−0.3 (2)
C12—C7—C8—C9	1.9 (3)	C17—C18—C19—C14	−1.2 (2)
C7—C8—C9—C10	−0.1 (3)	C23—C18—C19—C14	178.93 (15)
C8—C9—C10—C11	−1.2 (3)	C17—C18—C19—C24	179.62 (16)
C9—C10—C11—C12	0.7 (3)	C23—C18—C19—C24	−0.3 (2)
C10—C11—C12—N3	−179.82 (17)	C4—C5—N1—C1	0.7 (3)
C10—C11—C12—C7	1.1 (3)	C6—C5—N1—C1	−179.67 (18)
N2—C7—C12—N3	−1.48 (19)	C2—C1—N1—C5	0.1 (4)
C8—C7—C12—N3	178.23 (17)	N3—C6—N2—C7	0.2 (2)
N2—C7—C12—C11	177.79 (16)	C5—C6—N2—C7	179.26 (15)
C8—C7—C12—C11	−2.5 (3)	C8—C7—N2—C6	−178.8 (2)
N3—C13—C14—C19	−121.53 (16)	C12—C7—N2—C6	0.8 (2)
N3—C13—C14—C15	60.88 (19)	N2—C6—N3—C12	−1.10 (19)
C19—C14—C15—C16	4.3 (2)	C5—C6—N3—C12	179.91 (16)
C13—C14—C15—C16	−178.05 (14)	N2—C6—N3—C13	178.34 (15)
C19—C14—C15—C20	−174.84 (15)	C5—C6—N3—C13	−0.7 (3)
C13—C14—C15—C20	2.8 (2)	C11—C12—N3—C6	−177.65 (18)
C14—C15—C16—C17	−3.6 (2)	C7—C12—N3—C6	1.50 (17)
C20—C15—C16—C17	175.52 (15)	C11—C12—N3—C13	2.9 (3)
C14—C15—C16—C21	176.10 (16)	C7—C12—N3—C13	−177.98 (14)
C20—C15—C16—C21	−4.7 (2)	C14—C13—N3—C6	−125.33 (17)
C15—C16—C17—C18	0.5 (2)	C14—C13—N3—C12	54.0 (2)
C21—C16—C17—C18	−179.21 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···Cgi	0.97	2.91	3.6941 (18)	139
C13—H13B···N1	0.97	2.30	3.029 (2)	131

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C7–C12 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯Cg i	0.97	2.91	3.6941 (18)	139
C13—H13B⋯N1	0.97	2.30	3.029 (2)	131

Symmetry code: (i) .