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Acta Cryst. (2009). E65, o2613    [ doi:10.1107/S1600536809039051 ]

1-Benzyl-1H-benzimidazole

G. Lei and L. Zhou

Abstract top

In the title molecule, C14H12N2, 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, molecules are linked into chains along the a axis by C-H...N hydrogen bonds. In addition, the packing is stabilized by C-H...[pi] interactions involving both six-membered rings.

Comment top

Benzimidazole derivatives are a class of important compounds which exhibit antimicrobial activity (Ansari & Lal, 2009). Here, we report the crystal structure of the title compound.

Bond lengths and angles in the title molecule are normal. The benzimidazole ring system is planar, with a maximum deviation of 0.035 (2)Å for atom C4. The imidazole ring and benzene ring in benzyl group are almost mutually perpendicular, with a dihedral angle of 85.77 (4)% (Fig. 1). The crystal packing is stabilized by C—H···N hydrogen bonds and C—H···π interactions (Cg1 is the centroid of the C11-C16 ring and Cg2 is the centroid of the C4—C9 ring) (Table 1).

Related literature top

For general background to benzimidazole derivatives, see: Ansari & Lal (2009). For the synthesis, see: Hayat et al. (2001). Cg1 and Cg2 are the centroids of the C11–C16 and C4–C9 rings, respectively.

Experimental top

The title compound was synthesized according to the method reported in the literature (Hayat et al., 2001). Colourless single crystals suitable for X-ray diffraction were obtained by slow evaporation of a methanol solution.

Refinement top

All H atoms were placed in calculated positions, with C-H = 0.95 or 0.99 Å, and refined using a riding model, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO (Rigaku, 2004); data reduction: RAPID-AUTO (Rigaku, 2004); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering.
1-Benzyl-1H-benzimidazole top
Crystal data top
C14H12N2F(000) = 440
Mr = 208.26Dx = 1.308 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3307 reflections
a = 6.2265 (10) Åθ = 3.2–27.5°
b = 8.1740 (13) ŵ = 0.08 mm−1
c = 20.975 (4) ÅT = 93 K
β = 97.839 (2)°Block, colourless
V = 1057.5 (3) Å30.57 × 0.50 × 0.37 mm
Z = 4
Data collection top
Rigaku SPIDER
diffractometer		2198 reflections with I > 2σ(I)
Radiation source: Rotating AnodeRint = 0.022
graphiteθmax = 27.5°, θmin = 3.2°
ω scansh = −8→8
8358 measured reflectionsk = −10→10
2412 independent reflectionsl = −27→27
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H-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 parametersΔρmax = 0.21 e Å−3
0 restraintsΔρmin = −0.25 e Å−3
Crystal data top
C14H12N2V = 1057.5 (3) Å3
Mr = 208.26Z = 4
Monoclinic, P21/nMo Kα radiation
a = 6.2265 (10) ŵ = 0.08 mm−1
b = 8.1740 (13) ÅT = 93 K
c = 20.975 (4) Å0.57 × 0.50 × 0.37 mm
β = 97.839 (2)°
Data collection top
Rigaku SPIDER
diffractometer		Rint = 0.022
8358 measured reflectionsθmax = 27.5°
2412 independent reflectionsStandard reflections: 0
2198 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.093Δρmax = 0.21 e Å−3
S = 1.00Δρmin = −0.25 e Å−3
2412 reflectionsAbsolute structure: ?
145 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.41468 (13)0.11825 (10)0.58340 (4)0.0151 (2)
N20.08985 (14)0.00680 (11)0.59213 (4)0.0184 (2)
C20.21067 (16)0.08189 (12)0.55458 (5)0.0164 (2)
H20.16020.10860.51100.020*
C40.22460 (16)−0.00841 (12)0.65071 (5)0.0164 (2)
C50.18809 (18)−0.08552 (13)0.70781 (5)0.0206 (2)
H50.0516−0.13290.71220.025*
C60.35775 (19)−0.09021 (14)0.75762 (5)0.0234 (3)
H60.3374−0.14340.79660.028*
C70.55957 (19)−0.01845 (14)0.75220 (5)0.0230 (3)
H70.6720−0.02410.78760.028*
C80.59841 (17)0.06012 (13)0.69652 (5)0.0190 (2)
H80.73380.11030.69290.023*
C90.42797 (16)0.06166 (12)0.64598 (5)0.0153 (2)
C100.58686 (16)0.19667 (13)0.55403 (5)0.0163 (2)
H10A0.54880.19270.50670.020*
H10B0.72230.13340.56530.020*
C110.62877 (16)0.37280 (13)0.57428 (5)0.0148 (2)
C120.47606 (16)0.46721 (13)0.59998 (5)0.0175 (2)
H120.34140.42010.60660.021*
C130.51869 (18)0.63021 (13)0.61606 (5)0.0198 (2)
H130.41380.69360.63390.024*
C140.71437 (17)0.70020 (13)0.60598 (5)0.0187 (2)
H140.74290.81190.61650.022*
C150.86811 (17)0.60677 (13)0.58054 (5)0.0185 (2)
H151.00230.65440.57380.022*
C160.82598 (16)0.44380 (13)0.56497 (5)0.0171 (2)
H160.93220.38010.54780.021*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0142 (4)0.0141 (4)0.0168 (4)−0.0009 (3)0.0017 (3)−0.0012 (3)
N20.0160 (4)0.0162 (4)0.0226 (5)−0.0005 (3)0.0016 (3)0.0004 (4)
C20.0155 (5)0.0136 (5)0.0195 (5)0.0007 (4)−0.0002 (4)−0.0013 (4)
C40.0162 (5)0.0131 (5)0.0201 (5)0.0014 (4)0.0030 (4)−0.0028 (4)
C50.0211 (5)0.0181 (5)0.0239 (5)−0.0002 (4)0.0084 (4)−0.0008 (4)
C60.0305 (6)0.0229 (6)0.0178 (5)0.0026 (5)0.0074 (4)0.0005 (4)
C70.0256 (6)0.0248 (6)0.0176 (5)0.0029 (5)−0.0006 (4)−0.0033 (4)
C80.0171 (5)0.0193 (5)0.0205 (5)−0.0003 (4)0.0015 (4)−0.0040 (4)
C90.0174 (5)0.0119 (5)0.0172 (5)0.0017 (4)0.0037 (4)−0.0028 (4)
C100.0140 (5)0.0167 (5)0.0188 (5)−0.0008 (4)0.0043 (4)−0.0016 (4)
C110.0154 (5)0.0159 (5)0.0129 (5)0.0001 (4)0.0009 (4)0.0012 (4)
C120.0143 (5)0.0187 (5)0.0201 (5)−0.0008 (4)0.0039 (4)0.0000 (4)
C130.0198 (5)0.0173 (5)0.0227 (5)0.0031 (4)0.0048 (4)−0.0009 (4)
C140.0223 (5)0.0143 (5)0.0189 (5)−0.0009 (4)0.0010 (4)0.0005 (4)
C150.0165 (5)0.0198 (5)0.0192 (5)−0.0036 (4)0.0027 (4)0.0019 (4)
C160.0154 (5)0.0196 (5)0.0170 (5)0.0009 (4)0.0044 (4)−0.0001 (4)
Geometric parameters (Å, °) top
N1—C21.3630 (13)C8—H80.95
N1—C91.3835 (13)C10—C111.5137 (15)
N1—C101.4560 (13)C10—H10A0.99
N2—C21.3132 (14)C10—H10B0.99
N2—C41.3956 (13)C11—C121.3892 (14)
C2—H20.95C11—C161.3958 (14)
C4—C51.3992 (15)C12—C131.3910 (15)
C4—C91.4055 (14)C12—H120.95
C5—C61.3812 (16)C13—C141.3881 (15)
C5—H50.95C13—H130.95
C6—C71.4053 (17)C14—C151.3870 (15)
C6—H60.95C14—H140.95
C7—C81.3826 (16)C15—C161.3881 (16)
C7—H70.95C15—H150.95
C8—C91.3940 (14)C16—H160.95
C2—N1—C9106.23 (9)N1—C10—C11114.12 (8)
C2—N1—C10127.14 (9)N1—C10—H10A108.7
C9—N1—C10126.61 (8)C11—C10—H10A108.7
C2—N2—C4104.17 (9)N1—C10—H10B108.7
N2—C2—N1114.29 (9)C11—C10—H10B108.7
N2—C2—H2122.9H10A—C10—H10B107.6
N1—C2—H2122.9C12—C11—C16119.02 (10)
N2—C4—C5130.19 (10)C12—C11—C10122.43 (9)
N2—C4—C9109.93 (9)C16—C11—C10118.52 (9)
C5—C4—C9119.80 (10)C11—C12—C13120.53 (10)
C6—C5—C4117.59 (10)C11—C12—H12119.7
C6—C5—H5121.2C13—C12—H12119.7
C4—C5—H5121.2C14—C13—C12120.02 (10)
C5—C6—C7121.82 (10)C14—C13—H13120.0
C5—C6—H6119.1C12—C13—H13120.0
C7—C6—H6119.1C15—C14—C13119.86 (10)
C8—C7—C6121.57 (10)C15—C14—H14120.1
C8—C7—H7119.2C13—C14—H14120.1
C6—C7—H7119.2C14—C15—C16120.05 (10)
C7—C8—C9116.34 (10)C14—C15—H15120.0
C7—C8—H8121.8C16—C15—H15120.0
C9—C8—H8121.8C15—C16—C11120.51 (10)
N1—C9—C8131.71 (10)C15—C16—H16119.7
N1—C9—C4105.38 (9)C11—C16—H16119.7
C8—C9—C4122.85 (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—N1176.66 (9)
C10—N1—C2—N2178.24 (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—C90.40 (11)C2—N1—C10—C11105.93 (11)
N2—C4—C5—C6176.02 (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—C70.97 (16)N1—C10—C11—C16161.34 (9)
C5—C6—C7—C8−0.20 (17)C16—C11—C12—C130.16 (15)
C6—C7—C8—C9−1.03 (16)C10—C11—C12—C13−177.95 (10)
C2—N1—C9—C8177.52 (11)C11—C12—C13—C140.52 (16)
C10—N1—C9—C8−0.91 (17)C12—C13—C14—C15−0.72 (16)
C2—N1—C9—C40.41 (11)C13—C14—C15—C160.24 (16)
C10—N1—C9—C4−178.02 (9)C14—C15—C16—C110.45 (15)
C7—C8—C9—N1−175.17 (10)C12—C11—C16—C15−0.64 (15)
C7—C8—C9—C41.52 (15)C10—C11—C16—C15177.54 (9)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C10—H10B···N2i0.992.503.4890 (14)173
C7—H7···Cg1ii0.952.663.5220 (1)151
C13—H13···Cg2iii0.952.803.5660 (3)139
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y−1, −z+1; (iii) x, y+1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C10—H10B···N2i0.992.503.4890 (14)173
C7—H7···Cg1ii0.952.663.5220 (1)151
C13—H13···Cg2iii0.952.803.5660 (3)139
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y−1, −z+1; (iii) x, y+1, z.
Acknowledgements top

The authors thank the Centre for Testing and Analysis, Cheng Du Branch of the Chinese Academy of Sciences, for analytical support.

references
References top

Ansari, K. F. & Lal, C. (2009). Eur. J. Med. Chem. 44, 4028–4033.

Hayat, S., Atta-ur-Rahman, Choudhary, M. I., Khan, K. M., Schumann, W. & Bayer, E. (2001). Tetrahedron, 57, 9951–9957.

Rigaku (2004). RAPID-AUTO. Rigaku/MSC Inc., The Woodlands, Texas, USA.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.