1-Benzyl-1H-benzimidazole

Lei, G.; Zhou, L.

doi:10.1107/S1600536809039051

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2613

https://doi.org/10.1107/S1600536809039051

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1-Benzyl-1H-benzimidazole

Gang Lei ^a ^* and Li Zhou ^a

^aSchool of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
^*Correspondence e-mail: leigang307@yahoo.com.cn

(Received 25 September 2009; accepted 25 September 2009; online 3 October 2009)

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⋯π interactions 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_r = 208.26
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.038
wR(F²) = 0.093
S = 1.00
2412 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.25 e Å⁻³

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) x+1, y, z; (ii) -x+1, -y-1, -z+1; (iii) x, y+1, z. Cg1 and Cg2 are the centroids of the C11–C16 and C4–C9 rings, respectively.

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809039051/ci2926Isup2.hkl

checkCIF report

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.

Structure description 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.

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

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

C₁₄H₁₂N₂	F(000) = 440
M_r = 208.26	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0482P)² + 0.296P] where P = (F_o² + 2F_c²)/3
2412 reflections	(Δ/σ)_max = 0.001
145 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₄H₁₂N₂	V = 1057.5 (3) Å³
M_r = 208.26	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.2265 (10) Å	µ = 0.08 mm⁻¹
b = 8.1740 (13) Å	T = 93 K
c = 20.975 (4) Å	0.57 × 0.50 × 0.37 mm
β = 97.839 (2)°

Data collection top

Rigaku SPIDER diffractometer	2198 reflections with I > 2σ(I)
8358 measured reflections	R_int = 0.022
2412 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.093	H-atom parameters constrained
S = 1.00	Δρ_max = 0.21 e Å⁻³
2412 reflections	Δρ_min = −0.25 e Å⁻³
145 parameters

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z; (ii) −x+1, −y−1, −z+1; (iii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂N₂
M_r	208.26
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	93
a, b, c (Å)	6.2265 (10), 8.1740 (13), 20.975 (4)
β (°)	97.839 (2)
V (Å³)	1057.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.57 × 0.50 × 0.37

Data collection
Diffractometer	Rigaku SPIDER
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8358, 2412, 2198
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.093, 1.00
No. of reflections	2412
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.25

Computer programs: RAPID-AUTO (Rigaku, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z; (ii) −x+1, −y−1, −z+1; (iii) x, y+1, z.

Acknowledgements

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

References

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