1-(2,6-Diiso-propyl-phen-yl)-1H-benzimidazole.

In the title compound, C19H22N2, both the benzimidazole unit and the 2,6-diiso-propyl-phenyl group are essentially planar [maximum deviations from the least-squares planes of 0.005 (1) and 0.009 (1) Å, respectively]. The dihedral angle between the two planes is 79.6 (7)°. In the crystal, mol-ecules are linked into chains along the a-axis direction by weak C-H⋯N inter-actions. The crystal structure also features C-H⋯π inter-actions, which link the chains into a three-dimensional network.

Related literature

For the properties of related compounds, see: Shi et al. (2013 ▶); Cross et al. (1995 ▶); Akpinar et al. (2010 ▶); Wang et al. (2007 ▶); Mason et al. (1999 ▶). For bond lengths and angles in related structures, see: Jayamoorthy et al. (2013 ▶); Fathima et al. (2013 ▶); Geiger & Nellist (2013 ▶).

Experimental

Crystal data

C19H22N2

M = 278.39

Orthorhombic,

a = 6.6471 (8) Å

b = 14.1216 (18) Å

c = 17.285 (2) Å

V = 1622.5 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 173 K

0.44 × 0.42 × 0.28 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.971, T max = 0.982

9716 measured reflections

3551 independent reflections

3133 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.088

S = 1.08

3551 reflections

194 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; 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 datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813020473/bg2510sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813020473/bg2510Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813020473/bg2510Isup3.cml

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

C19H22N2	F(000) = 600
Mr = 278.39	Dx = 1.140 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5376 reflections
a = 6.6471 (8) Å	θ = 2.4–27.1°
b = 14.1216 (18) Å	µ = 0.07 mm−1
c = 17.285 (2) Å	T = 173 K
V = 1622.5 (4) Å3	Block, colorless
Z = 4	0.44 × 0.42 × 0.28 mm

Bruker APEXII CCD area-detector diffractometer	3551 independent reflections
Radiation source: fine-focus sealed tube	3133 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
Detector resolution: 0 pixels mm-1	θmax = 27.1°, θmin = 1.9°
phi and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −18→16
Tmin = 0.971, Tmax = 0.982	l = −18→22
9716 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0411P)2 + 0.2264P] where P = (Fo2 + 2Fc2)/3
3551 reflections	(Δ/σ)max < 0.001
194 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.16 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	1.2274 (2)	0.79599 (10)	0.29080 (8)	0.0303 (3)
H1	1.2920	0.7885	0.3394	0.036*
N1	1.32623 (17)	0.80167 (9)	0.22581 (7)	0.0335 (3)
C2	1.17791 (19)	0.81252 (9)	0.17010 (8)	0.0262 (3)
N2	1.02227 (16)	0.80177 (8)	0.28307 (6)	0.0243 (2)
C3	1.1940 (2)	0.82181 (10)	0.08970 (8)	0.0327 (3)
H3	1.3217	0.8218	0.0650	0.039*
C4	1.0203 (2)	0.83093 (11)	0.04764 (8)	0.0366 (3)
H4	1.0285	0.8375	−0.0070	0.044*
C5	0.8308 (2)	0.83080 (11)	0.08327 (8)	0.0347 (3)
H5	0.7138	0.8373	0.0522	0.042*
C6	0.8096 (2)	0.82147 (10)	0.16281 (8)	0.0284 (3)
H6	0.6814	0.8211	0.1872	0.034*
C7	0.9866 (2)	0.81270 (8)	0.20455 (7)	0.0234 (3)
C8	0.87636 (19)	0.80084 (9)	0.34461 (7)	0.0227 (3)
C9	0.8510 (2)	0.88320 (9)	0.38878 (7)	0.0254 (3)
C10	0.9634 (2)	0.97431 (10)	0.37135 (8)	0.0324 (3)
H10	1.0380	0.9652	0.3217	0.039*
C11	0.8185 (3)	1.05673 (13)	0.36039 (13)	0.0604 (6)
H11A	0.7243	1.0419	0.3185	0.091*
H11B	0.8946	1.1140	0.3472	0.091*
H11C	0.7436	1.0674	0.4084	0.091*
C12	1.1172 (4)	0.99708 (15)	0.43400 (12)	0.0645 (6)
H12A	1.0480	1.0063	0.4835	0.097*
H12B	1.1898	1.0550	0.4202	0.097*
H12C	1.2127	0.9445	0.4386	0.097*
C13	0.7136 (2)	0.87915 (10)	0.44978 (8)	0.0303 (3)
H13	0.6941	0.9334	0.4815	0.036*
C14	0.6056 (2)	0.79775 (11)	0.46485 (8)	0.0315 (3)
H14	0.5136	0.7963	0.5069	0.038*
C15	0.6306 (2)	0.71811 (10)	0.41892 (8)	0.0292 (3)
H15	0.5532	0.6630	0.4292	0.035*
C16	0.76747 (19)	0.71788 (10)	0.35795 (7)	0.0249 (3)
C17	0.8059 (2)	0.62843 (10)	0.31125 (8)	0.0303 (3)
H17	0.8567	0.6479	0.2592	0.036*
C18	0.9704 (3)	0.56985 (11)	0.35044 (10)	0.0421 (4)
H18A	1.0924	0.6083	0.3557	0.063*
H18B	0.9999	0.5138	0.3189	0.063*
H18C	0.9244	0.5499	0.4018	0.063*
C19	0.6166 (3)	0.56884 (13)	0.29914 (12)	0.0534 (5)
H19A	0.5719	0.5432	0.3489	0.080*
H19B	0.6465	0.5166	0.2636	0.080*
H19C	0.5101	0.6085	0.2771	0.080*

	U11	U22	U33	U12	U13	U23
C1	0.0239 (6)	0.0333 (8)	0.0338 (7)	0.0025 (6)	−0.0026 (6)	0.0005 (6)
N1	0.0241 (6)	0.0388 (7)	0.0375 (7)	0.0032 (5)	0.0041 (5)	0.0009 (5)
C2	0.0238 (6)	0.0226 (6)	0.0324 (7)	−0.0001 (5)	0.0043 (5)	−0.0012 (5)
N2	0.0211 (5)	0.0284 (6)	0.0234 (5)	0.0027 (5)	0.0009 (4)	−0.0005 (4)
C3	0.0331 (7)	0.0323 (8)	0.0325 (7)	−0.0025 (6)	0.0124 (6)	−0.0023 (6)
C4	0.0451 (9)	0.0407 (8)	0.0239 (7)	−0.0053 (7)	0.0070 (7)	−0.0005 (6)
C5	0.0328 (8)	0.0425 (8)	0.0286 (7)	−0.0065 (7)	−0.0041 (6)	0.0019 (6)
C6	0.0232 (6)	0.0348 (8)	0.0271 (7)	−0.0021 (6)	0.0015 (5)	−0.0005 (6)
C7	0.0265 (6)	0.0193 (6)	0.0244 (6)	−0.0011 (5)	0.0041 (5)	−0.0013 (5)
C8	0.0197 (6)	0.0294 (7)	0.0189 (6)	0.0034 (5)	−0.0001 (5)	0.0015 (5)
C9	0.0260 (6)	0.0271 (7)	0.0232 (6)	0.0022 (5)	−0.0026 (5)	0.0014 (5)
C10	0.0404 (8)	0.0262 (7)	0.0305 (7)	−0.0017 (6)	0.0044 (6)	−0.0009 (5)
C11	0.0707 (13)	0.0352 (9)	0.0754 (13)	0.0121 (9)	0.0173 (11)	0.0173 (9)
C12	0.0756 (14)	0.0544 (12)	0.0634 (13)	−0.0329 (11)	−0.0177 (11)	0.0042 (9)
C13	0.0354 (7)	0.0303 (7)	0.0254 (7)	0.0052 (6)	0.0029 (6)	−0.0026 (6)
C14	0.0283 (7)	0.0431 (8)	0.0232 (7)	0.0030 (6)	0.0054 (5)	0.0025 (6)
C15	0.0271 (7)	0.0322 (7)	0.0283 (7)	−0.0034 (6)	−0.0003 (6)	0.0056 (6)
C16	0.0249 (6)	0.0274 (7)	0.0226 (6)	0.0028 (5)	−0.0039 (5)	0.0014 (5)
C17	0.0374 (8)	0.0274 (7)	0.0262 (7)	−0.0015 (6)	−0.0019 (6)	−0.0018 (5)
C18	0.0470 (10)	0.0309 (8)	0.0485 (9)	0.0066 (7)	−0.0081 (8)	−0.0062 (7)
C19	0.0466 (10)	0.0429 (10)	0.0706 (13)	−0.0067 (8)	−0.0106 (10)	−0.0192 (9)

C1—N1	1.3038 (18)	C11—H11A	0.9800
C1—N2	1.3725 (16)	C11—H11B	0.9800
C1—H1	0.9500	C11—H11C	0.9800
N1—C2	1.3868 (18)	C12—H12A	0.9800
C2—C3	1.400 (2)	C12—H12B	0.9800
C2—C7	1.4044 (18)	C12—H12C	0.9800
N2—C7	1.3865 (16)	C13—C14	1.380 (2)
N2—C8	1.4396 (15)	C13—H13	0.9500
C3—C4	1.370 (2)	C14—C15	1.387 (2)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.402 (2)	C15—C16	1.3924 (19)
C4—H4	0.9500	C15—H15	0.9500
C5—C6	1.388 (2)	C16—C17	1.5207 (19)
C5—H5	0.9500	C17—C19	1.528 (2)
C6—C7	1.3857 (18)	C17—C18	1.529 (2)
C6—H6	0.9500	C17—H17	1.0000
C8—C16	1.3963 (19)	C18—H18A	0.9800
C8—C9	1.4013 (18)	C18—H18B	0.9800
C9—C13	1.3961 (19)	C18—H18C	0.9800
C9—C10	1.5181 (19)	C19—H19A	0.9800
C10—C11	1.522 (2)	C19—H19B	0.9800
C10—C12	1.524 (2)	C19—H19C	0.9800
C10—H10	1.0000
N1—C1—N2	114.39 (12)	C10—C11—H11C	109.5
N1—C1—H1	122.8	H11A—C11—H11C	109.5
N2—C1—H1	122.8	H11B—C11—H11C	109.5
C1—N1—C2	104.30 (11)	C10—C12—H12A	109.5
N1—C2—C3	130.20 (12)	C10—C12—H12B	109.5
N1—C2—C7	110.46 (11)	H12A—C12—H12B	109.5
C3—C2—C7	119.33 (12)	C10—C12—H12C	109.5
C1—N2—C7	105.78 (11)	H12A—C12—H12C	109.5
C1—N2—C8	126.64 (11)	H12B—C12—H12C	109.5
C7—N2—C8	127.52 (11)	C14—C13—C9	121.13 (13)
C4—C3—C2	118.11 (13)	C14—C13—H13	119.4
C4—C3—H3	120.9	C9—C13—H13	119.4
C2—C3—H3	120.9	C13—C14—C15	120.34 (12)
C3—C4—C5	121.57 (13)	C13—C14—H14	119.8
C3—C4—H4	119.2	C15—C14—H14	119.8
C5—C4—H4	119.2	C14—C15—C16	120.90 (13)
C6—C5—C4	121.77 (14)	C14—C15—H15	119.5
C6—C5—H5	119.1	C16—C15—H15	119.5
C4—C5—H5	119.1	C15—C16—C8	117.50 (12)
C7—C6—C5	115.96 (12)	C15—C16—C17	120.90 (12)
C7—C6—H6	122.0	C8—C16—C17	121.48 (11)
C5—C6—H6	122.0	C16—C17—C19	113.06 (12)
C6—C7—N2	131.68 (12)	C16—C17—C18	109.53 (11)
C6—C7—C2	123.26 (11)	C19—C17—C18	110.57 (13)
N2—C7—C2	105.06 (11)	C16—C17—H17	107.8
C16—C8—C9	122.96 (11)	C19—C17—H17	107.8
C16—C8—N2	118.61 (11)	C18—C17—H17	107.8
C9—C8—N2	118.43 (11)	C17—C18—H18A	109.5
C13—C9—C8	117.14 (12)	C17—C18—H18B	109.5
C13—C9—C10	120.43 (12)	H18A—C18—H18B	109.5
C8—C9—C10	122.42 (12)	C17—C18—H18C	109.5
C9—C10—C11	111.19 (13)	H18A—C18—H18C	109.5
C9—C10—C12	111.60 (13)	H18B—C18—H18C	109.5
C11—C10—C12	110.58 (15)	C17—C19—H19A	109.5
C9—C10—H10	107.8	C17—C19—H19B	109.5
C11—C10—H10	107.8	H19A—C19—H19B	109.5
C12—C10—H10	107.8	C17—C19—H19C	109.5
C10—C11—H11A	109.5	H19A—C19—H19C	109.5
C10—C11—H11B	109.5	H19B—C19—H19C	109.5
H11A—C11—H11B	109.5
N2—C1—N1—C2	0.30 (16)	C7—N2—C8—C9	−100.77 (14)
C1—N1—C2—C3	−179.65 (15)	C16—C8—C9—C13	1.78 (19)
C1—N1—C2—C7	−0.23 (15)	N2—C8—C9—C13	−177.79 (12)
N1—C1—N2—C7	−0.25 (16)	C16—C8—C9—C10	−177.13 (12)
N1—C1—N2—C8	−177.75 (12)	N2—C8—C9—C10	3.30 (18)
N1—C2—C3—C4	179.48 (14)	C13—C9—C10—C11	−54.09 (19)
C7—C2—C3—C4	0.1 (2)	C8—C9—C10—C11	124.78 (15)
C2—C3—C4—C5	−0.2 (2)	C13—C9—C10—C12	69.89 (19)
C3—C4—C5—C6	0.0 (2)	C8—C9—C10—C12	−111.24 (16)
C4—C5—C6—C7	0.2 (2)	C8—C9—C13—C14	−1.0 (2)
C5—C6—C7—N2	−179.57 (13)	C10—C9—C13—C14	177.94 (13)
C5—C6—C7—C2	−0.32 (19)	C9—C13—C14—C15	−0.5 (2)
C1—N2—C7—C6	179.44 (14)	C13—C14—C15—C16	1.4 (2)
C8—N2—C7—C6	−3.1 (2)	C14—C15—C16—C8	−0.60 (19)
C1—N2—C7—C2	0.09 (14)	C14—C15—C16—C17	175.54 (13)
C8—N2—C7—C2	177.56 (12)	C9—C8—C16—C15	−1.00 (18)
N1—C2—C7—C6	−179.34 (13)	N2—C8—C16—C15	178.57 (11)
C3—C2—C7—C6	0.16 (19)	C9—C8—C16—C17	−177.12 (12)
N1—C2—C7—N2	0.09 (14)	N2—C8—C16—C17	2.45 (18)
C3—C2—C7—N2	179.58 (12)	C15—C16—C17—C19	36.52 (19)
C1—N2—C8—C16	−103.40 (15)	C8—C16—C17—C19	−147.49 (14)
C7—N2—C8—C16	79.63 (16)	C15—C16—C17—C18	−87.28 (16)
C1—N2—C8—C9	76.19 (17)	C8—C16—C17—C18	88.71 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···N1i	0.95	2.47	3.4040 (18)	168
C14—H14···Cg3ii	0.95	2.68	3.5908 (16)	150
C18—H18B···Cg2iii	0.98	2.79	3.5314 (17)	125

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 and C8/C9/C13–C16 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯N1i	0.95	2.47	3.4040 (18)	168
C14—H14⋯Cg3ii	0.95	2.68	3.5908 (16)	150
C18—H18B⋯Cg2iii	0.98	2.79	3.5314 (17)	125

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