1-Benzyl-2-phenyl-1H-benzimidazole

Kong, L.

doi:10.1107/S1600536809001238

organic compounds

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Volume 65| Part 2| February 2009| Page o316

doi:10.1107/S1600536809001238

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1-Benzyl-2-phenyl-1H-benzimidazole

Lingqian Kong ^a ^*

^aDongchang College, Liaocheng University, Liaocheng 250059, People's Republic of China
^*Correspondence e-mail: konglingqian08@163.com

(Received 7 December 2008; accepted 10 January 2009; online 14 January 2009)

The title compound, C₂₀H₁₆N₂, has been synthesized by the reaction of benzaldehyde with o-phenylendiamine and L-proline. The benzimidazole group makes a dihedral angle of 29.04 (1)° with the attached benzene ring, and is approximately perpendicular to the plane of the benzyl group [dihedral angle = 88.9 (1)°] The crystal packing exhibits no unusually short intermolecular contacts.

Related literature

For background literature concerning benzimidazole compounds, see: Zarrinmayeh et al. (1998 ); Spasov et al. (1999 ). For a related structure, see: Yang et al. (2007 ).

Experimental

Crystal data

C₂₀H₁₆N₂
M_r = 284.35
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.338 (3) Å
b = 8.085 (3) Å
c = 30.190 (12) Å
V = 1547.0 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 298 (2) K
0.63 × 0.55 × 0.47 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.956, T_max = 0.967
6729 measured reflections
1631 independent reflections
1221 reflections with I > 2σ(I)
R_int = 0.073

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.115
S = 1.14
1631 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809001238/bi2334sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809001238/bi2334Isup2.hkl

checkCIF report

Comment top

The benzimidazole group is of significant importance in medicinal chemistry. Several publications report benzimidazole-containing compounds showing biological activities such as selective neuropeptide receptor antagonism (Zarrinmayeh, et al.,1998). Substituted benzimidazole derivatives have found commercial applications in veterinary medicine as anthelmintic agents and in diverse human therapeutic areas such as treatment of ulcers and as antihistaminics (Spasov, et al.,1999).

In the crystal structure of the title compound, the imidazole ring is almost coplanar with the benzene ring (C2/C3/C4/C5/C6/C7): the C1—N1—C3—C2 and C1—N2—C2—C3 torsion angles are 0.0 (3)° and -0.8 (3)°, respectively. The dihedral angles between the imidazole ring and the benzene rings (C2/C3/C4/C5/C6/C7) and (C15/C16/C17/C18/C19/C20) are 2.84 (1)° and 29.54 (1)°, respectively. There are no significantly short intermolecular contacts.

Related literature top

For background literature concerning benzimidazole compounds, see: Zarrinmayeh et al. (1998); Spasov et al. (1999). For a related structure, see: Yang et al. (2007).

Experimental top

o-Phenylendiamine (5 mmol), benzaldehyde (10 mmol), L-proline (1 mmol) and 10 ml ethanol were mixed in a 50 ml flask. After stirring for 4 h at 373 K, the resulting mixture was recrystalized from ethanol, affording the title compound as an orange crystalline solid. Elemental analysis calculated: C 84.48, H 5.67, N 9.85%; found: C 84.38, H 5.54, N 9.77%.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure showing 30% probability displacement ellipsoids for non-H atoms.

1-Benzyl-2-phenyl-1H-benzimidazole top

Crystal data top

C₂₀H₁₆N₂	F(000) = 600
M_r = 284.35	D_x = 1.221 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1704 reflections
a = 6.338 (3) Å	θ = 2.6–21.8°
b = 8.085 (3) Å	µ = 0.07 mm⁻¹
c = 30.190 (12) Å	T = 298 K
V = 1547.0 (10) Å³	Block, orange
Z = 4	0.63 × 0.55 × 0.47 mm

Data collection top

Bruker SMART CCD diffractometer	1631 independent reflections
Radiation source: fine-focus sealed tube	1221 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.073
ϕ and ω scans	θ_max = 25.1°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
T_min = 0.956, T_max = 0.967	k = −9→7
6729 measured reflections	l = −26→36

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0509P)²] where P = (F_o² + 2F_c²)/3
1631 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₀H₁₆N₂	V = 1547.0 (10) Å³
M_r = 284.35	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.338 (3) Å	µ = 0.07 mm⁻¹
b = 8.085 (3) Å	T = 298 K
c = 30.190 (12) Å	0.63 × 0.55 × 0.47 mm

Data collection top

Bruker SMART CCD diffractometer	1631 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1221 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.967	R_int = 0.073
6729 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.14	Δρ_max = 0.14 e Å⁻³
1631 reflections	Δρ_min = −0.16 e Å⁻³
199 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	0.2537 (4)	−0.0386 (3)	0.13584 (8)	0.0404 (6)
N2	0.5764 (4)	−0.1478 (3)	0.14294 (9)	0.0457 (7)
C1	0.4421 (5)	−0.0765 (3)	0.11598 (10)	0.0383 (7)
C2	0.4713 (5)	−0.1607 (3)	0.18323 (11)	0.0421 (8)
C3	0.2703 (5)	−0.0923 (3)	0.17932 (10)	0.0406 (7)
C4	0.1274 (6)	−0.0905 (4)	0.21384 (12)	0.0543 (9)
H4	−0.0051	−0.0422	0.2110	0.065*
C5	0.1920 (7)	−0.1639 (5)	0.25254 (13)	0.0678 (11)
H5	0.1002	−0.1667	0.2766	0.081*
C6	0.3909 (7)	−0.2340 (5)	0.25674 (13)	0.0683 (12)
H6	0.4288	−0.2824	0.2835	0.082*
C7	0.5324 (7)	−0.2341 (4)	0.22272 (12)	0.0588 (10)
H7	0.6651	−0.2816	0.2259	0.071*
C8	0.0616 (5)	0.0304 (4)	0.11706 (11)	0.0422 (8)
H8A	−0.0587	−0.0290	0.1290	0.051*
H8B	0.0630	0.0134	0.0853	0.051*
C9	0.0341 (5)	0.2130 (3)	0.12639 (10)	0.0352 (7)
C10	0.1930 (5)	0.3114 (4)	0.14264 (11)	0.0484 (9)
H10	0.3250	0.2656	0.1482	0.058*
C11	0.1592 (6)	0.4782 (4)	0.15079 (13)	0.0574 (10)
H11	0.2680	0.5430	0.1620	0.069*
C12	−0.0329 (6)	0.5478 (4)	0.14239 (12)	0.0551 (9)
H12	−0.0550	0.6597	0.1477	0.066*
C13	−0.1927 (6)	0.4519 (4)	0.12605 (12)	0.0559 (10)
H13	−0.3239	0.4988	0.1203	0.067*
C14	−0.1601 (5)	0.2856 (4)	0.11803 (11)	0.0479 (9)
H14	−0.2698	0.2215	0.1069	0.057*
C15	0.4924 (5)	−0.0445 (4)	0.06922 (10)	0.0422 (8)
C16	0.6356 (5)	−0.1483 (4)	0.04824 (12)	0.0538 (9)
H16	0.6957	−0.2351	0.0640	0.065*
C17	0.6904 (6)	−0.1255 (6)	0.00461 (13)	0.0721 (12)
H17	0.7854	−0.1972	−0.0089	0.087*
C18	0.6052 (7)	0.0028 (5)	−0.01897 (14)	0.0737 (13)
H18	0.6398	0.0174	−0.0487	0.088*
C19	0.4695 (7)	0.1087 (5)	0.00140 (12)	0.0730 (12)
H19	0.4147	0.1976	−0.0144	0.088*
C20	0.4119 (6)	0.0867 (4)	0.04484 (11)	0.0555 (9)
H20	0.3183	0.1603	0.0580	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0385 (15)	0.0347 (14)	0.0479 (17)	0.0033 (12)	−0.0049 (14)	−0.0007 (12)
N2	0.0378 (14)	0.0455 (16)	0.0537 (17)	0.0033 (13)	−0.0038 (14)	0.0020 (13)
C1	0.0364 (17)	0.0306 (16)	0.0480 (18)	0.0017 (14)	−0.0020 (16)	−0.0081 (13)
C2	0.0455 (19)	0.0329 (16)	0.048 (2)	−0.0025 (15)	−0.0023 (17)	−0.0001 (14)
C3	0.0487 (19)	0.0315 (16)	0.0416 (19)	−0.0025 (15)	−0.0015 (16)	0.0004 (14)
C4	0.058 (2)	0.051 (2)	0.054 (2)	0.0026 (18)	0.0044 (19)	−0.0065 (18)
C5	0.082 (3)	0.075 (3)	0.047 (2)	−0.008 (3)	0.014 (2)	−0.0034 (19)
C6	0.087 (3)	0.070 (3)	0.048 (2)	−0.006 (2)	−0.012 (2)	0.0142 (19)
C7	0.062 (2)	0.054 (2)	0.061 (2)	0.0028 (19)	−0.012 (2)	0.0057 (18)
C8	0.0329 (16)	0.0359 (16)	0.058 (2)	0.0006 (13)	−0.0057 (15)	−0.0050 (14)
C9	0.0362 (16)	0.0308 (15)	0.0386 (16)	−0.0016 (13)	0.0000 (15)	0.0013 (12)
C10	0.0438 (19)	0.0394 (19)	0.062 (2)	−0.0019 (15)	−0.0084 (18)	−0.0063 (15)
C11	0.062 (2)	0.037 (2)	0.073 (3)	−0.0080 (18)	−0.009 (2)	−0.0133 (17)
C12	0.064 (2)	0.0332 (18)	0.068 (2)	0.0079 (18)	0.006 (2)	−0.0025 (16)
C13	0.048 (2)	0.048 (2)	0.072 (2)	0.0140 (17)	0.000 (2)	0.0042 (18)
C14	0.0406 (19)	0.0438 (19)	0.059 (2)	0.0001 (15)	−0.0070 (17)	−0.0045 (16)
C15	0.0456 (19)	0.0395 (16)	0.0415 (18)	−0.0051 (16)	0.0004 (15)	−0.0052 (14)
C16	0.051 (2)	0.058 (2)	0.052 (2)	0.0088 (18)	−0.0033 (19)	−0.0058 (18)
C17	0.066 (3)	0.085 (3)	0.066 (3)	0.009 (2)	0.015 (2)	−0.018 (2)
C18	0.082 (3)	0.095 (3)	0.045 (2)	−0.008 (3)	0.015 (2)	−0.002 (2)
C19	0.084 (3)	0.081 (3)	0.054 (2)	0.003 (3)	−0.001 (2)	0.014 (2)
C20	0.060 (2)	0.056 (2)	0.051 (2)	0.0035 (18)	0.0035 (19)	0.0005 (17)

Geometric parameters (Å, º) top

N1—C1	1.371 (4)	C10—C11	1.387 (5)
N1—C3	1.387 (4)	C10—H10	0.930
N1—C8	1.454 (4)	C11—C12	1.365 (5)
N2—C1	1.311 (4)	C11—H11	0.930
N2—C2	1.391 (4)	C12—C13	1.368 (5)
C1—C15	1.470 (4)	C12—H12	0.930
C2—C7	1.387 (4)	C13—C14	1.382 (4)
C2—C3	1.394 (4)	C13—H13	0.930
C3—C4	1.381 (4)	C14—H14	0.930
C4—C5	1.373 (5)	C15—C20	1.388 (4)
C4—H4	0.930	C15—C16	1.389 (4)
C5—C6	1.388 (5)	C16—C17	1.375 (5)
C5—H5	0.930	C16—H16	0.930
C6—C7	1.363 (5)	C17—C18	1.369 (6)
C6—H6	0.930	C17—H17	0.930
C7—H7	0.930	C18—C19	1.360 (6)
C8—C9	1.513 (4)	C18—H18	0.930
C8—H8A	0.970	C19—C20	1.373 (5)
C8—H8B	0.970	C19—H19	0.930
C9—C10	1.374 (4)	C20—H20	0.930
C9—C14	1.387 (4)

C1—N1—C3	106.1 (2)	C9—C10—C11	120.8 (3)
C1—N1—C8	130.1 (3)	C9—C10—H10	119.6
C3—N1—C8	123.6 (3)	C11—C10—H10	119.6
C1—N2—C2	105.4 (3)	C12—C11—C10	120.4 (3)
N2—C1—N1	113.1 (3)	C12—C11—H11	119.8
N2—C1—C15	122.2 (3)	C10—C11—H11	119.8
N1—C1—C15	124.7 (3)	C11—C12—C13	119.6 (3)
C7—C2—C3	119.8 (3)	C11—C12—H12	120.2
C7—C2—N2	130.6 (3)	C13—C12—H12	120.2
C3—C2—N2	109.5 (3)	C12—C13—C14	120.3 (3)
C4—C3—N1	131.4 (3)	C12—C13—H13	119.9
C4—C3—C2	122.7 (3)	C14—C13—H13	119.9
N1—C3—C2	105.9 (3)	C13—C14—C9	120.8 (3)
C5—C4—C3	116.2 (4)	C13—C14—H14	119.6
C5—C4—H4	121.9	C9—C14—H14	119.6
C3—C4—H4	121.9	C20—C15—C16	117.4 (3)
C4—C5—C6	121.7 (4)	C20—C15—C1	124.3 (3)
C4—C5—H5	119.2	C16—C15—C1	118.2 (3)
C6—C5—H5	119.2	C17—C16—C15	121.4 (3)
C7—C6—C5	121.9 (4)	C17—C16—H16	119.3
C7—C6—H6	119.0	C15—C16—H16	119.3
C5—C6—H6	119.0	C18—C17—C16	120.0 (4)
C6—C7—C2	117.6 (4)	C18—C17—H17	120.0
C6—C7—H7	121.2	C16—C17—H17	120.0
C2—C7—H7	121.2	C19—C18—C17	119.4 (4)
N1—C8—C9	113.4 (2)	C19—C18—H18	120.3
N1—C8—H8A	108.9	C17—C18—H18	120.3
C9—C8—H8A	108.9	C18—C19—C20	121.2 (4)
N1—C8—H8B	108.9	C18—C19—H19	119.4
C9—C8—H8B	108.9	C20—C19—H19	119.4
H8A—C8—H8B	107.7	C19—C20—C15	120.5 (3)
C10—C9—C14	118.1 (3)	C19—C20—H20	119.7
C10—C9—C8	123.2 (3)	C15—C20—H20	119.7
C14—C9—C8	118.8 (3)

C2—N2—C1—N1	0.9 (3)	C3—N1—C8—C9	83.9 (3)
C2—N2—C1—C15	−178.4 (3)	N1—C8—C9—C10	12.9 (4)
C3—N1—C1—N2	−0.6 (3)	N1—C8—C9—C14	−167.4 (3)
C8—N1—C1—N2	−175.6 (3)	C14—C9—C10—C11	0.6 (5)
C3—N1—C1—C15	178.6 (3)	C8—C9—C10—C11	−179.7 (3)
C8—N1—C1—C15	3.6 (5)	C9—C10—C11—C12	−0.6 (6)
C1—N2—C2—C7	175.9 (3)	C10—C11—C12—C13	0.3 (6)
C1—N2—C2—C3	−0.8 (3)	C11—C12—C13—C14	−0.1 (6)
C1—N1—C3—C4	−177.9 (3)	C12—C13—C14—C9	0.1 (5)
C8—N1—C3—C4	−2.4 (5)	C10—C9—C14—C13	−0.3 (5)
C1—N1—C3—C2	0.0 (3)	C8—C9—C14—C13	180.0 (3)
C8—N1—C3—C2	175.5 (2)	N2—C1—C15—C20	−149.6 (3)
C7—C2—C3—C4	1.6 (4)	N1—C1—C15—C20	31.2 (5)
N2—C2—C3—C4	178.6 (3)	N2—C1—C15—C16	28.0 (4)
C7—C2—C3—N1	−176.6 (3)	N1—C1—C15—C16	−151.2 (3)
N2—C2—C3—N1	0.5 (3)	C20—C15—C16—C17	−2.1 (5)
N1—C3—C4—C5	176.1 (3)	C1—C15—C16—C17	−179.9 (3)
C2—C3—C4—C5	−1.5 (5)	C15—C16—C17—C18	0.7 (6)
C3—C4—C5—C6	0.8 (5)	C16—C17—C18—C19	1.2 (7)
C4—C5—C6—C7	−0.1 (6)	C17—C18—C19—C20	−1.8 (6)
C5—C6—C7—C2	0.1 (5)	C18—C19—C20—C15	0.4 (6)
C3—C2—C7—C6	−0.8 (5)	C16—C15—C20—C19	1.5 (5)
N2—C2—C7—C6	−177.2 (3)	C1—C15—C20—C19	179.2 (3)
C1—N1—C8—C9	−101.8 (4)

Experimental details

Crystal data
Chemical formula	C₂₀H₁₆N₂
M_r	284.35
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	6.338 (3), 8.085 (3), 30.190 (12)
V (Å³)	1547.0 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.63 × 0.55 × 0.47

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.956, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	6729, 1631, 1221
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.115, 1.14
No. of reflections	1631
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.16

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This project was supported by the Foundation of Dongchang College, Liaocheng University (grant No. DCLG2008002).

References

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