1-Benzyl-1H-benzimidazole.

In the title mol-ecule, C(14)H(12)N(2), the benzimidazole ring system is essentially planar (r.m.s. deviation = 0.024 Å). The dihedral angle between the imidazole ring and the benzyl ring is 85.77 (4)°. In the crystal, mol-ecules are linked into chains along the a axis by C-H⋯N hydrogen bonds. In addition, the packing is stabilized by C-H⋯π inter-actions involving both six-membered rings.

Related literature

For general background to benzimidazole derivatives, see: Ansari & Lal (2009 ▶). For the synthesis, see: Hayat et al. (2001 ▶).

Experimental

Crystal data

C14H12N2

M = 208.26

Monoclinic,

a = 6.2265 (10) Å

b = 8.1740 (13) Å

c = 20.975 (4) Å

β = 97.839 (2)°

V = 1057.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 93 K

0.57 × 0.50 × 0.37 mm

Data collection

Rigaku SPIDER diffractometer

Absorption correction: none

8358 measured reflections

2412 independent reflections

2198 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.093

S = 1.00

2412 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.25 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809039051/ci2926sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039051/ci2926Isup2.hkl

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

C14H12N2	F(000) = 440
Mr = 208.26	Dx = 1.308 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3307 reflections
a = 6.2265 (10) Å	θ = 3.2–27.5°
b = 8.1740 (13) Å	µ = 0.08 mm−1
c = 20.975 (4) Å	T = 93 K
β = 97.839 (2)°	Block, colourless
V = 1057.5 (3) Å3	0.57 × 0.50 × 0.37 mm
Z = 4

Rigaku SPIDER diffractometer	2198 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.022
graphite	θmax = 27.5°, θmin = 3.2°
ω scans	h = −8→8
8358 measured reflections	k = −10→10
2412 independent reflections	l = −27→27

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0482P)2 + 0.296P] where P = (Fo2 + 2Fc2)/3
2412 reflections	(Δ/σ)max = 0.001
145 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.25 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	0.41468 (13)	0.11825 (10)	0.58340 (4)	0.0151 (2)
N2	0.08985 (14)	0.00680 (11)	0.59213 (4)	0.0184 (2)
C2	0.21067 (16)	0.08189 (12)	0.55458 (5)	0.0164 (2)
H2	0.1602	0.1086	0.5110	0.020*
C4	0.22460 (16)	−0.00841 (12)	0.65071 (5)	0.0164 (2)
C5	0.18809 (18)	−0.08552 (13)	0.70781 (5)	0.0206 (2)
H5	0.0516	−0.1329	0.7122	0.025*
C6	0.35775 (19)	−0.09021 (14)	0.75762 (5)	0.0234 (3)
H6	0.3374	−0.1434	0.7966	0.028*
C7	0.55957 (19)	−0.01845 (14)	0.75220 (5)	0.0230 (3)
H7	0.6720	−0.0241	0.7876	0.028*
C8	0.59841 (17)	0.06012 (13)	0.69652 (5)	0.0190 (2)
H8	0.7338	0.1103	0.6929	0.023*
C9	0.42797 (16)	0.06166 (12)	0.64598 (5)	0.0153 (2)
C10	0.58686 (16)	0.19667 (13)	0.55403 (5)	0.0163 (2)
H10A	0.5488	0.1927	0.5067	0.020*
H10B	0.7223	0.1334	0.5653	0.020*
C11	0.62877 (16)	0.37280 (13)	0.57428 (5)	0.0148 (2)
C12	0.47606 (16)	0.46721 (13)	0.59998 (5)	0.0175 (2)
H12	0.3414	0.4201	0.6066	0.021*
C13	0.51869 (18)	0.63021 (13)	0.61606 (5)	0.0198 (2)
H13	0.4138	0.6936	0.6339	0.024*
C14	0.71437 (17)	0.70020 (13)	0.60598 (5)	0.0187 (2)
H14	0.7429	0.8119	0.6165	0.022*
C15	0.86811 (17)	0.60677 (13)	0.58054 (5)	0.0185 (2)
H15	1.0023	0.6544	0.5738	0.022*
C16	0.82598 (16)	0.44380 (13)	0.56497 (5)	0.0171 (2)
H16	0.9322	0.3801	0.5478	0.021*

	U11	U22	U33	U12	U13	U23
N1	0.0142 (4)	0.0141 (4)	0.0168 (4)	−0.0009 (3)	0.0017 (3)	−0.0012 (3)
N2	0.0160 (4)	0.0162 (4)	0.0226 (5)	−0.0005 (3)	0.0016 (3)	0.0004 (4)
C2	0.0155 (5)	0.0136 (5)	0.0195 (5)	0.0007 (4)	−0.0002 (4)	−0.0013 (4)
C4	0.0162 (5)	0.0131 (5)	0.0201 (5)	0.0014 (4)	0.0030 (4)	−0.0028 (4)
C5	0.0211 (5)	0.0181 (5)	0.0239 (5)	−0.0002 (4)	0.0084 (4)	−0.0008 (4)
C6	0.0305 (6)	0.0229 (6)	0.0178 (5)	0.0026 (5)	0.0074 (4)	0.0005 (4)
C7	0.0256 (6)	0.0248 (6)	0.0176 (5)	0.0029 (5)	−0.0006 (4)	−0.0033 (4)
C8	0.0171 (5)	0.0193 (5)	0.0205 (5)	−0.0003 (4)	0.0015 (4)	−0.0040 (4)
C9	0.0174 (5)	0.0119 (5)	0.0172 (5)	0.0017 (4)	0.0037 (4)	−0.0028 (4)
C10	0.0140 (5)	0.0167 (5)	0.0188 (5)	−0.0008 (4)	0.0043 (4)	−0.0016 (4)
C11	0.0154 (5)	0.0159 (5)	0.0129 (5)	0.0001 (4)	0.0009 (4)	0.0012 (4)
C12	0.0143 (5)	0.0187 (5)	0.0201 (5)	−0.0008 (4)	0.0039 (4)	0.0000 (4)
C13	0.0198 (5)	0.0173 (5)	0.0227 (5)	0.0031 (4)	0.0048 (4)	−0.0009 (4)
C14	0.0223 (5)	0.0143 (5)	0.0189 (5)	−0.0009 (4)	0.0010 (4)	0.0005 (4)
C15	0.0165 (5)	0.0198 (5)	0.0192 (5)	−0.0036 (4)	0.0027 (4)	0.0019 (4)
C16	0.0154 (5)	0.0196 (5)	0.0170 (5)	0.0009 (4)	0.0044 (4)	−0.0001 (4)

N1—C2	1.3630 (13)	C8—H8	0.95
N1—C9	1.3835 (13)	C10—C11	1.5137 (15)
N1—C10	1.4560 (13)	C10—H10A	0.99
N2—C2	1.3132 (14)	C10—H10B	0.99
N2—C4	1.3956 (13)	C11—C12	1.3892 (14)
C2—H2	0.95	C11—C16	1.3958 (14)
C4—C5	1.3992 (15)	C12—C13	1.3910 (15)
C4—C9	1.4055 (14)	C12—H12	0.95
C5—C6	1.3812 (16)	C13—C14	1.3881 (15)
C5—H5	0.95	C13—H13	0.95
C6—C7	1.4053 (17)	C14—C15	1.3870 (15)
C6—H6	0.95	C14—H14	0.95
C7—C8	1.3826 (16)	C15—C16	1.3881 (16)
C7—H7	0.95	C15—H15	0.95
C8—C9	1.3940 (14)	C16—H16	0.95
C2—N1—C9	106.23 (9)	N1—C10—C11	114.12 (8)
C2—N1—C10	127.14 (9)	N1—C10—H10A	108.7
C9—N1—C10	126.61 (8)	C11—C10—H10A	108.7
C2—N2—C4	104.17 (9)	N1—C10—H10B	108.7
N2—C2—N1	114.29 (9)	C11—C10—H10B	108.7
N2—C2—H2	122.9	H10A—C10—H10B	107.6
N1—C2—H2	122.9	C12—C11—C16	119.02 (10)
N2—C4—C5	130.19 (10)	C12—C11—C10	122.43 (9)
N2—C4—C9	109.93 (9)	C16—C11—C10	118.52 (9)
C5—C4—C9	119.80 (10)	C11—C12—C13	120.53 (10)
C6—C5—C4	117.59 (10)	C11—C12—H12	119.7
C6—C5—H5	121.2	C13—C12—H12	119.7
C4—C5—H5	121.2	C14—C13—C12	120.02 (10)
C5—C6—C7	121.82 (10)	C14—C13—H13	120.0
C5—C6—H6	119.1	C12—C13—H13	120.0
C7—C6—H6	119.1	C15—C14—C13	119.86 (10)
C8—C7—C6	121.57 (10)	C15—C14—H14	120.1
C8—C7—H7	119.2	C13—C14—H14	120.1
C6—C7—H7	119.2	C14—C15—C16	120.05 (10)
C7—C8—C9	116.34 (10)	C14—C15—H15	120.0
C7—C8—H8	121.8	C16—C15—H15	120.0
C9—C8—H8	121.8	C15—C16—C11	120.51 (10)
N1—C9—C8	131.71 (10)	C15—C16—H16	119.7
N1—C9—C4	105.38 (9)	C11—C16—H16	119.7
C8—C9—C4	122.85 (10)
C4—N2—C2—N1	−0.14 (12)	N2—C4—C9—N1	−0.51 (11)
C9—N1—C2—N2	−0.17 (12)	C5—C4—C9—N1	176.66 (9)
C10—N1—C2—N2	178.24 (9)	N2—C4—C9—C8	−177.95 (9)
C2—N2—C4—C5	−176.38 (11)	C5—C4—C9—C8	−0.78 (15)
C2—N2—C4—C9	0.40 (11)	C2—N1—C10—C11	105.93 (11)
N2—C4—C5—C6	176.02 (10)	C9—N1—C10—C11	−75.97 (12)
C9—C4—C5—C6	−0.49 (15)	N1—C10—C11—C12	−20.55 (13)
C4—C5—C6—C7	0.97 (16)	N1—C10—C11—C16	161.34 (9)
C5—C6—C7—C8	−0.20 (17)	C16—C11—C12—C13	0.16 (15)
C6—C7—C8—C9	−1.03 (16)	C10—C11—C12—C13	−177.95 (10)
C2—N1—C9—C8	177.52 (11)	C11—C12—C13—C14	0.52 (16)
C10—N1—C9—C8	−0.91 (17)	C12—C13—C14—C15	−0.72 (16)
C2—N1—C9—C4	0.41 (11)	C13—C14—C15—C16	0.24 (16)
C10—N1—C9—C4	−178.02 (9)	C14—C15—C16—C11	0.45 (15)
C7—C8—C9—N1	−175.17 (10)	C12—C11—C16—C15	−0.64 (15)
C7—C8—C9—C4	1.52 (15)	C10—C11—C16—C15	177.54 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···N2i	0.99	2.50	3.4890 (14)	173
C7—H7···Cg1ii	0.95	2.66	3.5220 (1)	151
C13—H13···Cg2iii	0.95	2.80	3.5660 (3)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯N2i	0.99	2.50	3.4890 (14)	173
C7—H7⋯Cg1ii	0.95	2.66	3.5220 (1)	151
C13—H13⋯Cg2iii	0.95	2.80	3.5660 (3)	139

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the C11–C16 and C4–C9 rings, respectively.