1-(4-tert-Butyl-benz-yl)-2-(4-tert-butyl-phen-yl)-1H-benzimidazole.

In the mol-ecule of the title compound, C(28)H(32)N(2), the benzimidazole ring system is almost planar [maximum deviation = 0.0221 (15) Å] and forms dihedral angles of 85.86 (4) and 32.09 (6)° with the benzene rings. In the crystal structure, mol-ecules are linked into chains running parallel to the a axis by inter-molecular C-H⋯N hydrogen bonds. The methyl groups of a tert-butyl group are rotationally disordered over two positions with refined site-occupancy factors of 0.636 (4) and 0.364 (4).

Related literature

For the biological and pharmaceutical properties of benzimidazole derivatives, see: Matsuno et al. (2000 ▶). Garuti et al. (1999 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C28H32N2

M = 396.56

Monoclinic,

a = 6.2142 (5) Å

b = 21.1112 (13) Å

c = 17.4624 (12) Å

β = 92.869 (6)°

V = 2288.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.20 × 0.20 × 0.10 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.987, T max = 0.993

24819 measured reflections

5239 independent reflections

4315 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.135

S = 1.09

5239 reflections

302 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.18 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/S1600536809045668/rz2378sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045668/rz2378Isup2.hkl

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

C28H32N2	F(000) = 856
Mr = 396.56	Dx = 1.151 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3426 reflections
a = 6.2142 (5) Å	θ = 2.3–27.5°
b = 21.1112 (13) Å	µ = 0.07 mm−1
c = 17.4624 (12) Å	T = 293 K
β = 92.869 (6)°	Block, colourless
V = 2288.0 (3) Å3	0.20 × 0.20 × 0.10 mm
Z = 4

Rigaku SCXmini diffractometer	5239 independent reflections
Radiation source: fine-focus sealed tube	4315 reflections with I > 2σ(I)
graphite	Rint = 0.047
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.3°
ω scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −27→27
Tmin = 0.987, Tmax = 0.993	l = −22→22
24819 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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0431P)2 + 0.936P] where P = (Fo2 + 2Fc2)/3
5239 reflections	(Δ/σ)max < 0.001
302 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.18 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	Occ. (<1)
N1	0.7010 (2)	0.17678 (6)	0.27399 (7)	0.0256 (3)
N2	1.0343 (2)	0.14275 (6)	0.31033 (7)	0.0298 (3)
C1	0.7112 (3)	0.17535 (7)	0.35346 (9)	0.0270 (3)
C2	0.5570 (3)	0.18846 (8)	0.40650 (10)	0.0346 (4)
H2B	0.4192	0.2021	0.3913	0.041*
C3	0.6195 (3)	0.18016 (9)	0.48290 (10)	0.0392 (4)
H3A	0.5214	0.1884	0.5201	0.047*
C4	0.8268 (3)	0.15961 (9)	0.50544 (10)	0.0382 (4)
H4A	0.8632	0.1547	0.5574	0.046*
C5	0.9793 (3)	0.14633 (8)	0.45281 (10)	0.0344 (4)
H5A	1.1170	0.1328	0.4684	0.041*
C6	0.9185 (3)	0.15411 (7)	0.37498 (9)	0.0282 (3)
C7	0.8992 (2)	0.15635 (7)	0.25137 (9)	0.0258 (3)
C8	0.9583 (2)	0.14654 (7)	0.17169 (9)	0.0272 (3)
C9	0.8876 (3)	0.18418 (8)	0.10959 (9)	0.0310 (4)
H9A	0.7887	0.2164	0.1168	0.037*
C10	0.9638 (3)	0.17391 (9)	0.03713 (10)	0.0355 (4)
H10A	0.9141	0.1995	−0.0033	0.043*
C11	1.1119 (3)	0.12648 (8)	0.02342 (10)	0.0344 (4)
C12	1.1810 (3)	0.08896 (8)	0.08579 (10)	0.0370 (4)
H12A	1.2802	0.0568	0.0785	0.044*
C13	1.1055 (3)	0.09845 (8)	0.15806 (10)	0.0335 (4)
H13A	1.1537	0.0723	0.1982	0.040*
C14	1.1974 (3)	0.11519 (9)	−0.05650 (10)	0.0424 (5)
C15	1.4372 (5)	0.1228 (2)	−0.0550 (2)	0.0569 (10)	0.636 (4)
H15A	1.4726	0.1670	−0.0576	0.085*	0.636 (4)
H15B	1.4930	0.1011	−0.0980	0.085*	0.636 (4)
H15C	1.4996	0.1051	−0.0083	0.085*	0.636 (4)
C16	1.1017 (6)	0.16598 (17)	−0.11722 (17)	0.0508 (9)	0.636 (4)
H16A	0.9475	0.1625	−0.1212	0.076*	0.636 (4)
H16B	1.1587	0.1580	−0.1664	0.076*	0.636 (4)
H16C	1.1414	0.2079	−0.1004	0.076*	0.636 (4)
C17	1.1189 (8)	0.0513 (2)	−0.0846 (2)	0.0687 (14)	0.636 (4)
H17A	0.9695	0.0541	−0.1011	0.103*	0.636 (4)
H17B	1.1360	0.0209	−0.0438	0.103*	0.636 (4)
H17C	1.2014	0.0381	−0.1268	0.103*	0.636 (4)
C16'	1.3128 (12)	0.1723 (4)	−0.0785 (4)	0.073 (2)	0.364 (4)
H16D	1.2128	0.2068	−0.0851	0.109*	0.364 (4)
H16E	1.3811	0.1648	−0.1258	0.109*	0.364 (4)
H16F	1.4201	0.1828	−0.0391	0.109*	0.364 (4)
C15'	1.3773 (13)	0.0576 (4)	−0.0524 (3)	0.077 (3)	0.364 (4)
H15D	1.3107	0.0193	−0.0360	0.116*	0.364 (4)
H15E	1.4934	0.0688	−0.0166	0.116*	0.364 (4)
H15F	1.4323	0.0514	−0.1023	0.116*	0.364 (4)
C17'	1.0230 (11)	0.0946 (4)	−0.1102 (3)	0.0593 (19)	0.364 (4)
H17D	0.9132	0.1266	−0.1137	0.089*	0.364 (4)
H17E	0.9627	0.0558	−0.0922	0.089*	0.364 (4)
H17F	1.0787	0.0879	−0.1598	0.089*	0.364 (4)
C18	0.5117 (2)	0.19700 (7)	0.22771 (9)	0.0276 (3)
H18A	0.3834	0.1845	0.2533	0.033*
H18B	0.5100	0.1753	0.1787	0.033*
C19	0.5039 (2)	0.26793 (7)	0.21354 (8)	0.0244 (3)
C20	0.6751 (3)	0.30771 (8)	0.23238 (10)	0.0345 (4)
H20A	0.7992	0.2912	0.2568	0.041*
C21	0.6647 (3)	0.37210 (8)	0.21545 (10)	0.0354 (4)
H21A	0.7823	0.3976	0.2292	0.042*
C22	0.4846 (2)	0.39941 (7)	0.17869 (9)	0.0255 (3)
C23	0.3127 (3)	0.35908 (8)	0.16148 (11)	0.0380 (4)
H23A	0.1875	0.3756	0.1379	0.046*
C24	0.3214 (3)	0.29478 (8)	0.17827 (11)	0.0370 (4)
H24A	0.2026	0.2694	0.1656	0.044*
C25	0.4755 (3)	0.47028 (7)	0.15925 (10)	0.0314 (4)
C26	0.6985 (3)	0.49533 (9)	0.14043 (12)	0.0454 (5)
H26A	0.7489	0.4729	0.0970	0.068*
H26B	0.7974	0.4891	0.1838	0.068*
H26C	0.6887	0.5397	0.1287	0.068*
C27	0.3234 (3)	0.48367 (9)	0.08955 (12)	0.0474 (5)
H27A	0.3723	0.4612	0.0459	0.071*
H27B	0.3218	0.5283	0.0791	0.071*
H27C	0.1806	0.4699	0.1000	0.071*
C28	0.3968 (4)	0.50619 (9)	0.22849 (12)	0.0586 (6)
H28A	0.2570	0.4909	0.2404	0.088*
H28B	0.3882	0.5506	0.2168	0.088*
H28C	0.4959	0.4997	0.2717	0.088*

	U11	U22	U33	U12	U13	U23
N1	0.0275 (7)	0.0240 (6)	0.0255 (7)	0.0003 (5)	0.0032 (5)	0.0028 (5)
N2	0.0303 (7)	0.0312 (7)	0.0280 (7)	0.0019 (5)	0.0030 (6)	0.0021 (6)
C1	0.0328 (8)	0.0225 (7)	0.0259 (8)	−0.0023 (6)	0.0048 (6)	0.0025 (6)
C2	0.0335 (9)	0.0364 (9)	0.0344 (9)	0.0014 (7)	0.0075 (7)	0.0009 (7)
C3	0.0449 (11)	0.0425 (10)	0.0311 (9)	−0.0027 (8)	0.0118 (8)	−0.0010 (8)
C4	0.0482 (11)	0.0403 (10)	0.0263 (9)	−0.0046 (8)	0.0030 (7)	0.0035 (7)
C5	0.0375 (9)	0.0350 (9)	0.0306 (9)	−0.0009 (7)	0.0007 (7)	0.0044 (7)
C6	0.0321 (8)	0.0255 (8)	0.0271 (8)	−0.0018 (6)	0.0038 (6)	0.0023 (6)
C7	0.0281 (8)	0.0217 (7)	0.0277 (8)	−0.0012 (6)	0.0038 (6)	0.0016 (6)
C8	0.0281 (8)	0.0261 (8)	0.0276 (8)	−0.0049 (6)	0.0029 (6)	−0.0006 (6)
C9	0.0323 (9)	0.0304 (8)	0.0303 (9)	−0.0015 (7)	0.0032 (7)	0.0001 (7)
C10	0.0395 (10)	0.0388 (9)	0.0282 (9)	−0.0057 (7)	0.0023 (7)	0.0015 (7)
C11	0.0351 (9)	0.0387 (9)	0.0300 (9)	−0.0102 (7)	0.0067 (7)	−0.0082 (7)
C12	0.0371 (10)	0.0354 (9)	0.0391 (10)	0.0023 (7)	0.0076 (8)	−0.0077 (8)
C13	0.0353 (9)	0.0323 (9)	0.0330 (9)	0.0015 (7)	0.0034 (7)	−0.0003 (7)
C14	0.0468 (11)	0.0484 (11)	0.0333 (10)	−0.0098 (9)	0.0136 (8)	−0.0078 (8)
C15	0.048 (2)	0.078 (3)	0.047 (2)	0.0041 (18)	0.0199 (15)	0.0108 (18)
C16	0.056 (2)	0.070 (2)	0.0278 (15)	−0.0027 (17)	0.0097 (14)	0.0037 (15)
C17	0.105 (4)	0.059 (2)	0.045 (2)	−0.023 (2)	0.032 (2)	−0.0254 (19)
C16'	0.081 (6)	0.077 (5)	0.063 (4)	−0.019 (4)	0.041 (4)	−0.001 (4)
C15'	0.095 (6)	0.103 (6)	0.036 (3)	0.056 (5)	0.024 (3)	0.003 (4)
C17'	0.069 (4)	0.073 (5)	0.036 (3)	0.006 (3)	0.002 (3)	−0.015 (3)
C18	0.0254 (8)	0.0258 (8)	0.0316 (8)	−0.0026 (6)	−0.0001 (6)	0.0012 (6)
C19	0.0251 (8)	0.0247 (7)	0.0236 (7)	−0.0008 (6)	0.0039 (6)	−0.0004 (6)
C20	0.0289 (9)	0.0296 (8)	0.0437 (10)	−0.0010 (6)	−0.0107 (7)	0.0043 (7)
C21	0.0303 (9)	0.0272 (8)	0.0476 (11)	−0.0054 (6)	−0.0080 (7)	0.0018 (7)
C22	0.0273 (8)	0.0250 (7)	0.0243 (8)	0.0017 (6)	0.0041 (6)	−0.0007 (6)
C23	0.0271 (9)	0.0309 (9)	0.0548 (11)	0.0012 (7)	−0.0097 (8)	0.0059 (8)
C24	0.0260 (8)	0.0303 (9)	0.0538 (11)	−0.0057 (7)	−0.0074 (7)	0.0032 (8)
C25	0.0382 (9)	0.0248 (8)	0.0316 (9)	0.0022 (7)	0.0056 (7)	0.0022 (7)
C26	0.0454 (11)	0.0331 (9)	0.0576 (12)	−0.0072 (8)	0.0028 (9)	0.0099 (9)
C27	0.0487 (12)	0.0408 (10)	0.0525 (12)	0.0016 (9)	−0.0011 (9)	0.0176 (9)
C28	0.1005 (19)	0.0285 (9)	0.0493 (12)	0.0113 (10)	0.0287 (12)	0.0019 (9)

N1—C7	1.3816 (19)	C17—H17A	0.9600
N1—C1	1.386 (2)	C17—H17B	0.9600
N1—C18	1.4571 (19)	C17—H17C	0.9600
N2—C7	1.327 (2)	C16'—H16D	0.9600
N2—C6	1.390 (2)	C16'—H16E	0.9600
C1—C2	1.393 (2)	C16'—H16F	0.9600
C1—C6	1.398 (2)	C15'—H15D	0.9600
C2—C3	1.382 (2)	C15'—H15E	0.9600
C2—H2B	0.9300	C15'—H15F	0.9600
C3—C4	1.397 (3)	C17'—H17D	0.9600
C3—H3A	0.9300	C17'—H17E	0.9600
C4—C5	1.381 (2)	C17'—H17F	0.9600
C4—H4A	0.9300	C18—C19	1.518 (2)
C5—C6	1.402 (2)	C18—H18A	0.9700
C5—H5A	0.9300	C18—H18B	0.9700
C7—C8	1.471 (2)	C19—C20	1.382 (2)
C8—C13	1.395 (2)	C19—C24	1.385 (2)
C8—C9	1.397 (2)	C20—C21	1.392 (2)
C9—C10	1.390 (2)	C20—H20A	0.9300
C9—H9A	0.9300	C21—C22	1.387 (2)
C10—C11	1.389 (2)	C21—H21A	0.9300
C10—H10A	0.9300	C22—C23	1.387 (2)
C11—C12	1.397 (3)	C22—C25	1.535 (2)
C11—C14	1.536 (2)	C23—C24	1.389 (2)
C12—C13	1.383 (2)	C23—H23A	0.9300
C12—H12A	0.9300	C24—H24A	0.9300
C13—H13A	0.9300	C25—C28	1.528 (2)
C14—C17'	1.463 (6)	C25—C27	1.530 (2)
C14—C16'	1.465 (7)	C25—C26	1.534 (2)
C14—C15	1.498 (4)	C26—H26A	0.9600
C14—C17	1.508 (4)	C26—H26B	0.9600
C14—C16	1.601 (4)	C26—H26C	0.9600
C14—C15'	1.650 (6)	C27—H27A	0.9600
C15—H15A	0.9600	C27—H27B	0.9600
C15—H15B	0.9600	C27—H27C	0.9600
C15—H15C	0.9600	C28—H28A	0.9600
C16—H16A	0.9600	C28—H28B	0.9600
C16—H16B	0.9600	C28—H28C	0.9600
C16—H16C	0.9600
C7—N1—C1	106.40 (13)	C14—C17—H17A	109.5
C7—N1—C18	129.74 (13)	C14—C17—H17B	109.5
C1—N1—C18	123.86 (13)	H17A—C17—H17B	109.5
C7—N2—C6	105.05 (13)	C14—C17—H17C	109.5
N1—C1—C2	131.48 (15)	H17A—C17—H17C	109.5
N1—C1—C6	105.77 (13)	H17B—C17—H17C	109.5
C2—C1—C6	122.70 (15)	C14—C16'—H16D	109.5
C3—C2—C1	116.56 (16)	C14—C16'—H16E	109.5
C3—C2—H2B	121.7	H16D—C16'—H16E	109.5
C1—C2—H2B	121.7	C14—C16'—H16F	109.5
C2—C3—C4	121.47 (16)	H16D—C16'—H16F	109.5
C2—C3—H3A	119.3	H16E—C16'—H16F	109.5
C4—C3—H3A	119.3	C14—C15'—H15D	109.5
C5—C4—C3	121.94 (16)	C14—C15'—H15E	109.5
C5—C4—H4A	119.0	H15D—C15'—H15E	109.5
C3—C4—H4A	119.0	C14—C15'—H15F	109.5
C4—C5—C6	117.44 (16)	H15D—C15'—H15F	109.5
C4—C5—H5A	121.3	H15E—C15'—H15F	109.5
C6—C5—H5A	121.3	C14—C17'—H17D	109.5
N2—C6—C1	110.16 (13)	C14—C17'—H17E	109.5
N2—C6—C5	129.95 (15)	H17D—C17'—H17E	109.5
C1—C6—C5	119.88 (15)	C14—C17'—H17F	109.5
N2—C7—N1	112.61 (14)	H17D—C17'—H17F	109.5
N2—C7—C8	121.68 (14)	H17E—C17'—H17F	109.5
N1—C7—C8	125.63 (14)	N1—C18—C19	113.43 (12)
C13—C8—C9	117.69 (15)	N1—C18—H18A	108.9
C13—C8—C7	117.42 (14)	C19—C18—H18A	108.9
C9—C8—C7	124.78 (14)	N1—C18—H18B	108.9
C10—C9—C8	120.65 (16)	C19—C18—H18B	108.9
C10—C9—H9A	119.7	H18A—C18—H18B	107.7
C8—C9—H9A	119.7	C20—C19—C24	117.44 (14)
C11—C10—C9	121.88 (16)	C20—C19—C18	122.86 (14)
C11—C10—H10A	119.1	C24—C19—C18	119.67 (14)
C9—C10—H10A	119.1	C19—C20—C21	121.05 (15)
C10—C11—C12	117.05 (15)	C19—C20—H20A	119.5
C10—C11—C14	122.04 (17)	C21—C20—H20A	119.5
C12—C11—C14	120.91 (16)	C22—C21—C20	122.13 (15)
C13—C12—C11	121.63 (16)	C22—C21—H21A	118.9
C13—C12—H12A	119.2	C20—C21—H21A	118.9
C11—C12—H12A	119.2	C23—C22—C21	116.09 (14)
C12—C13—C8	121.10 (16)	C23—C22—C25	122.07 (14)
C12—C13—H13A	119.5	C21—C22—C25	121.83 (14)
C8—C13—H13A	119.5	C22—C23—C24	122.19 (15)
C17'—C14—C16'	115.7 (5)	C22—C23—H23A	118.9
C17'—C14—C15	138.4 (3)	C24—C23—H23A	118.9
C16'—C14—C15	54.3 (4)	C19—C24—C23	121.07 (15)
C17'—C14—C17	46.3 (3)	C19—C24—H24A	119.5
C16'—C14—C17	143.7 (3)	C23—C24—H24A	119.5
C15—C14—C17	114.0 (3)	C28—C25—C27	109.18 (16)
C17'—C14—C11	110.5 (3)	C28—C25—C26	109.07 (16)
C16'—C14—C11	107.9 (3)	C27—C25—C26	107.14 (15)
C15—C14—C11	110.84 (19)	C28—C25—C22	108.57 (14)
C17—C14—C11	108.26 (19)	C27—C25—C22	111.76 (14)
C17'—C14—C16	62.4 (3)	C26—C25—C22	111.08 (14)
C16'—C14—C16	56.3 (4)	C25—C26—H26A	109.5
C15—C14—C16	106.1 (2)	C25—C26—H26B	109.5
C17—C14—C16	106.3 (3)	H26A—C26—H26B	109.5
C11—C14—C16	111.34 (18)	C25—C26—H26C	109.5
C17'—C14—C15'	106.7 (4)	H26A—C26—H26C	109.5
C16'—C14—C15'	106.2 (5)	H26B—C26—H26C	109.5
C15—C14—C15'	53.6 (4)	C25—C27—H27A	109.5
C17—C14—C15'	64.1 (4)	C25—C27—H27B	109.5
C11—C14—C15'	109.8 (2)	H27A—C27—H27B	109.5
C16—C14—C15'	138.6 (3)	C25—C27—H27C	109.5
C14—C15—H15A	109.5	H27A—C27—H27C	109.5
C14—C15—H15B	109.5	H27B—C27—H27C	109.5
H15A—C15—H15B	109.5	C25—C28—H28A	109.5
C14—C15—H15C	109.5	C25—C28—H28B	109.5
H15A—C15—H15C	109.5	H28A—C28—H28B	109.5
H15B—C15—H15C	109.5	C25—C28—H28C	109.5
C14—C16—H16A	109.5	H28A—C28—H28C	109.5
C14—C16—H16B	109.5	H28B—C28—H28C	109.5
C14—C16—H16C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···N2i	0.97	2.59	3.553 (2)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18A⋯N2i	0.97	2.59	3.553 (2)	174

Symmetry code: (i) .