2-[4-(1H-1,2,4-Triazol-1-yl)phen­yl]-1H-benzimidazole

Cheng, L.-H.; Zheng, Z.; Han, Z.-L.; Wu, Z.-C.; Zhou, H.-P.

doi:10.1107/S1600536812037816

organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page o2890

https://doi.org/10.1107/S1600536812037816

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2-[4-(1H-1,2,4-Triazol-1-yl)phenyl]-1H-benzimidazole

Long-Huai Cheng,^a Zheng Zheng,^a Zhi-Li Han,^a Zhi-Chao Wu ^a and Hong-Ping Zhou ^a ^*

^aCollege of Chemistry and Chemical Engineering, Anhui University, Hefei 230039, People's Republic of China
^*Correspondence e-mail: zhpzhp@263.net

(Received 27 July 2012; accepted 3 September 2012; online 8 September 2012)

In the title compound, C₁₅H₁₁N₅, the benzimidazole ring system is nearly planar [maximum deviation = 0.039 (2) Å], and is oriented at a dihedral angle of 28.85 (10)° with respect to the benzene ring; the dihedral angle between the triazole and benzene rings is 17.30 (15)°. In the crystal N—H⋯N hydrogen bonds link the molecules into chains. Weak C—H⋯N interactions are also present.

Related literature

For the crystal structures of Co(II) and Pt(II) complexes with benzimidazole ligands, see: Xia et al. (2012 ); Qiu et al. (2011 ).

Experimental

Crystal data

C₁₅H₁₁N₅
M_r = 261.29
Orthorhombic, P b c a
a = 8.323 (5) Å
b = 10.002 (5) Å
c = 30.068 (5) Å
V = 2503 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
16453 measured reflections
2194 independent reflections
1563 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.171
S = 1.15
2194 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H19⋯N1ⁱ	0.86	2.06	2.877 (3)	159
C21—H21⋯N9ⁱⁱ	0.93	2.62	3.309 (5)	132
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) -x+2, -y+1, -z.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812037816/xu5598sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812037816/xu5598Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812037816/xu5598Isup3.cml

checkCIF report

Comment top

The derivatives of the title compound, (I), are often used as coordinating ligands in the metal complexes (Xia et al., 2012; Qiu et al., 2011). Herewith we presenet the crystal structure of (I).

In (I) (Fig.1), the imidazole ring is twisted out of the plane of benzene ring at 17.3 (1)°, the benzimidazole and benzene rings form a dihedral angle of 28.8 (1)°. In the crystal structure, intermolecular N—H···N hydrogen bonds link the molecules into chains.

Related literature top

For the crystal structures of Co(II) and Pt(II) complexes with benzimidazole ligands, see: Xia et al. (2012); Qiu et al. (2011).

Experimental top

A mixture of 4-(1H-1, 2, 4-triazol-1-yl)benzaldehyde (0.86 g, 5.0 mmol) and o-phenylenediamine (0.54 g, 5.0 mmol) was refluxed in ethanol (20 ml) over night. The yellow compound that formed was filtered, washed several times with dichloromethane and dried in air. The compound was recrystallized from methanol to give light yellow crystals. Yield: 1.08 g (83%).

Structure description top

The derivatives of the title compound, (I), are often used as coordinating ligands in the metal complexes (Xia et al., 2012; Qiu et al., 2011). Herewith we presenet the crystal structure of (I).

For the crystal structures of Co(II) and Pt(II) complexes with benzimidazole ligands, see: Xia et al. (2012); Qiu et al. (2011).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. : The molecular structure of the title molecule(I) showing 30% probability displacement ellipsoids.
	Fig. 2. : The H-bond diagram of the title molecule(I).

2-[4-(1H-1,2,4-Triazol-1-yl)phenyl]-1H-benzimidazole top

Crystal data top

C₁₅H₁₁N₅	F(000) = 1088
M_r = 261.29	D_x = 1.387 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2017 reflections
a = 8.323 (5) Å	θ = 2.7–21.7°
b = 10.002 (5) Å	µ = 0.09 mm⁻¹
c = 30.068 (5) Å	T = 298 K
V = 2503 (2) Å³	Block, yellow
Z = 8	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1563 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.053
Graphite monochromator	θ_max = 25.0°, θ_min = 1.4°
phi and ω scans	h = −9→9
16453 measured reflections	k = −11→11
2194 independent reflections	l = −35→34

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.171	H-atom parameters constrained
S = 1.15	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
2194 reflections	(Δ/σ)_max < 0.001
181 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₅H₁₁N₅	V = 2503 (2) Å³
M_r = 261.29	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 8.323 (5) Å	µ = 0.09 mm⁻¹
b = 10.002 (5) Å	T = 298 K
c = 30.068 (5) Å	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1563 reflections with I > 2σ(I)
16453 measured reflections	R_int = 0.053
2194 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.171	H-atom parameters constrained
S = 1.15	Δρ_max = 0.35 e Å⁻³
2194 reflections	Δρ_min = −0.22 e Å⁻³
181 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	0.1867 (2)	0.31253 (16)	0.15540 (6)	0.0393 (5)
N2	0.2336 (2)	0.09230 (16)	0.15838 (6)	0.0396 (5)
H19	0.2797	0.0163	0.1544	0.048*
C8	0.4410 (3)	0.2305 (2)	0.12203 (7)	0.0381 (6)
C5	0.0618 (3)	0.2523 (2)	0.17899 (7)	0.0375 (6)
C6	0.0911 (3)	0.1146 (2)	0.18041 (8)	0.0359 (6)
C7	0.2869 (3)	0.2113 (2)	0.14441 (8)	0.0381 (6)
C1	−0.0105 (3)	0.0285 (2)	0.20314 (8)	0.0441 (6)
H1	0.0080	−0.0632	0.2037	0.053*
C11	0.7386 (3)	0.2637 (2)	0.08161 (8)	0.0427 (6)
N8	0.9995 (3)	0.1770 (2)	0.05945 (9)	0.0628 (7)
N3	0.8913 (3)	0.2799 (2)	0.06084 (7)	0.0490 (6)
C12	0.6162 (3)	0.3542 (2)	0.07322 (9)	0.0494 (7)
H12	0.6332	0.4254	0.0539	0.059*
C4	−0.0694 (3)	0.3067 (2)	0.20085 (9)	0.0483 (7)
H4	−0.0893	0.3982	0.2002	0.058*
C10	0.7146 (3)	0.1580 (2)	0.11043 (9)	0.0524 (7)
H10	0.7977	0.0989	0.1167	0.063*
C13	0.4691 (3)	0.3382 (2)	0.09374 (9)	0.0468 (7)
H13	0.3877	0.4000	0.0886	0.056*
C9	0.5654 (3)	0.1414 (2)	0.12971 (9)	0.0527 (7)
H9	0.5480	0.0686	0.1483	0.063*
C2	−0.1397 (3)	0.0843 (2)	0.22475 (9)	0.0504 (7)
H2	−0.2092	0.0293	0.2406	0.060*
C21	0.9583 (4)	0.3865 (3)	0.04163 (10)	0.0667 (9)
H21	0.9075	0.4689	0.0387	0.080*
N9	1.1047 (3)	0.3612 (3)	0.02737 (10)	0.0760 (8)
C20	1.1220 (4)	0.2326 (3)	0.03917 (10)	0.0677 (9)
H20	1.2159	0.1854	0.0333	0.081*
C3	−0.1687 (3)	0.2213 (3)	0.22336 (9)	0.0525 (7)
H3	−0.2578	0.2556	0.2381	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0388 (12)	0.0302 (10)	0.0490 (12)	−0.0008 (8)	0.0043 (9)	−0.0020 (8)
N2	0.0419 (12)	0.0228 (9)	0.0541 (13)	0.0013 (8)	0.0022 (10)	0.0007 (8)
C8	0.0368 (13)	0.0322 (12)	0.0453 (14)	−0.0017 (10)	0.0023 (11)	−0.0011 (10)
C5	0.0385 (13)	0.0347 (12)	0.0393 (13)	−0.0021 (10)	0.0019 (11)	0.0003 (10)
C6	0.0377 (13)	0.0282 (11)	0.0416 (13)	−0.0022 (9)	−0.0020 (11)	−0.0001 (9)
C7	0.0362 (14)	0.0345 (12)	0.0437 (14)	−0.0039 (10)	−0.0011 (11)	−0.0003 (10)
C1	0.0483 (15)	0.0321 (12)	0.0520 (15)	−0.0048 (11)	0.0002 (12)	0.0038 (11)
C11	0.0395 (14)	0.0417 (13)	0.0468 (15)	−0.0035 (11)	0.0021 (12)	−0.0019 (11)
N8	0.0485 (15)	0.0668 (15)	0.0729 (17)	0.0092 (12)	0.0085 (13)	0.0012 (12)
N3	0.0439 (13)	0.0528 (13)	0.0503 (13)	−0.0005 (10)	0.0071 (10)	0.0040 (10)
C12	0.0512 (16)	0.0397 (13)	0.0573 (17)	−0.0023 (11)	0.0078 (13)	0.0093 (11)
C4	0.0512 (16)	0.0350 (13)	0.0587 (17)	0.0053 (11)	0.0104 (13)	−0.0004 (11)
C10	0.0428 (16)	0.0527 (16)	0.0617 (18)	0.0080 (11)	0.0041 (13)	0.0127 (13)
C13	0.0446 (15)	0.0361 (13)	0.0598 (17)	0.0015 (10)	0.0041 (13)	0.0046 (11)
C9	0.0476 (16)	0.0476 (15)	0.0630 (18)	0.0006 (12)	0.0042 (13)	0.0164 (13)
C2	0.0496 (16)	0.0492 (15)	0.0524 (16)	−0.0107 (12)	0.0084 (13)	0.0017 (12)
C21	0.0587 (19)	0.0660 (18)	0.075 (2)	−0.0033 (15)	0.0197 (16)	0.0149 (16)
N9	0.0561 (16)	0.090 (2)	0.0816 (19)	−0.0035 (14)	0.0180 (15)	0.0179 (15)
C20	0.0483 (18)	0.094 (2)	0.0610 (19)	0.0058 (16)	0.0080 (15)	0.0023 (17)
C3	0.0483 (16)	0.0508 (16)	0.0585 (17)	0.0027 (12)	0.0148 (14)	−0.0039 (12)

Geometric parameters (Å, º) top

N1—C7	1.352 (3)	N8—N3	1.368 (3)
N1—C5	1.395 (3)	N3—C21	1.335 (3)
N2—C7	1.338 (3)	C12—C13	1.381 (3)
N2—C6	1.377 (3)	C12—H12	0.9300
N2—H19	0.8600	C4—C3	1.368 (3)
C8—C9	1.386 (3)	C4—H4	0.9300
C8—C13	1.392 (3)	C10—C9	1.380 (4)
C8—C7	1.461 (3)	C10—H10	0.9300
C5—C4	1.386 (3)	C13—H13	0.9300
C5—C6	1.400 (3)	C9—H9	0.9300
C6—C1	1.387 (3)	C2—C3	1.392 (4)
C1—C2	1.374 (3)	C2—H2	0.9300
C1—H1	0.9300	C21—N9	1.316 (4)
C11—C10	1.382 (3)	C21—H21	0.9300
C11—C12	1.386 (3)	N9—C20	1.342 (4)
C11—N3	1.425 (3)	C20—H20	0.9300
N8—C20	1.312 (4)	C3—H3	0.9300

C7—N1—C5	105.10 (18)	C13—C12—H12	120.2
C7—N2—C6	107.00 (17)	C11—C12—H12	120.2
C7—N2—H19	126.5	C3—C4—C5	117.8 (2)
C6—N2—H19	126.5	C3—C4—H4	121.1
C9—C8—C13	118.3 (2)	C5—C4—H4	121.1
C9—C8—C7	119.7 (2)	C9—C10—C11	119.1 (2)
C13—C8—C7	122.0 (2)	C9—C10—H10	120.5
C4—C5—N1	131.2 (2)	C11—C10—H10	120.5
C4—C5—C6	120.6 (2)	C12—C13—C8	120.8 (2)
N1—C5—C6	108.1 (2)	C12—C13—H13	119.6
N2—C6—C1	131.5 (2)	C8—C13—H13	119.6
N2—C6—C5	107.15 (19)	C10—C9—C8	121.7 (2)
C1—C6—C5	121.3 (2)	C10—C9—H9	119.2
N2—C7—N1	112.7 (2)	C8—C9—H9	119.2
N2—C7—C8	123.5 (2)	C1—C2—C3	121.4 (2)
N1—C7—C8	123.73 (19)	C1—C2—H2	119.3
C2—C1—C6	117.3 (2)	C3—C2—H2	119.3
C2—C1—H1	121.4	N9—C21—N3	111.9 (3)
C6—C1—H1	121.4	N9—C21—H21	124.0
C10—C11—C12	120.5 (2)	N3—C21—H21	124.0
C10—C11—N3	119.4 (2)	C21—N9—C20	101.4 (2)
C12—C11—N3	120.1 (2)	N8—C20—N9	116.5 (3)
C20—N8—N3	102.0 (2)	N8—C20—H20	121.8
C21—N3—N8	108.2 (2)	N9—C20—H20	121.8
C21—N3—C11	130.7 (2)	C4—C3—C2	121.7 (2)
N8—N3—C11	121.0 (2)	C4—C3—H3	119.2
C13—C12—C11	119.6 (2)	C2—C3—H3	119.2

C7—N1—C5—C4	175.3 (3)	C10—C11—N3—N8	17.1 (4)
C7—N1—C5—C6	−1.2 (2)	C12—C11—N3—N8	−163.6 (2)
C7—N2—C6—C1	−176.6 (3)	C10—C11—C12—C13	−0.2 (4)
C7—N2—C6—C5	−0.1 (2)	N3—C11—C12—C13	−179.6 (2)
C4—C5—C6—N2	−176.2 (2)	N1—C5—C4—C3	−176.6 (2)
N1—C5—C6—N2	0.8 (2)	C6—C5—C4—C3	−0.5 (4)
C4—C5—C6—C1	0.8 (4)	C12—C11—C10—C9	2.0 (4)
N1—C5—C6—C1	177.7 (2)	N3—C11—C10—C9	−178.7 (2)
C6—N2—C7—N1	−0.7 (3)	C11—C12—C13—C8	−1.4 (4)
C6—N2—C7—C8	175.9 (2)	C9—C8—C13—C12	1.2 (4)
C5—N1—C7—N2	1.2 (3)	C7—C8—C13—C12	179.6 (2)
C5—N1—C7—C8	−175.4 (2)	C11—C10—C9—C8	−2.2 (4)
C9—C8—C7—N2	−26.1 (3)	C13—C8—C9—C10	0.6 (4)
C13—C8—C7—N2	155.5 (2)	C7—C8—C9—C10	−177.9 (2)
C9—C8—C7—N1	150.1 (2)	C6—C1—C2—C3	0.9 (4)
C13—C8—C7—N1	−28.3 (3)	N8—N3—C21—N9	0.1 (4)
N2—C6—C1—C2	175.1 (2)	C11—N3—C21—N9	178.1 (3)
C5—C6—C1—C2	−1.0 (4)	N3—C21—N9—C20	0.0 (4)
C20—N8—N3—C21	−0.2 (3)	N3—N8—C20—N9	0.2 (4)
C20—N8—N3—C11	−178.4 (2)	C21—N9—C20—N8	−0.1 (4)
C10—C11—N3—C21	−160.7 (3)	C5—C4—C3—C2	0.4 (4)
C12—C11—N3—C21	18.7 (4)	C1—C2—C3—C4	−0.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H19···N1ⁱ	0.86	2.06	2.877 (3)	159
C21—H21···N9ⁱⁱ	0.93	2.62	3.309 (5)	132

Symmetry codes: (i) −x+1/2, y−1/2, z; (ii) −x+2, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₁N₅
M_r	261.29
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	8.323 (5), 10.002 (5), 30.068 (5)
V (Å³)	2503 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	16453, 2194, 1563
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.171, 1.15
No. of reflections	2194
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.22

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H19···N1ⁱ	0.86	2.06	2.877 (3)	159
C21—H21···N9ⁱⁱ	0.93	2.62	3.309 (5)	132

Symmetry codes: (i) −x+1/2, y−1/2, z; (ii) −x+2, −y+1, −z.

Acknowledgements

This work was supported by a grant from the Anhui University Student Innovative Experiment Plan (KYXL20110033), the Program for New Century Excellent Talents in Universities of China, the Doctoral Program Foundation of the Ministry of Education of China (20113401110004), the 211 Project of Anhui University and the Natural Science Foundation of the Education Committee of Anhui Province, China (KJ2012A024).

References

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