1-Allyl-1H-1,3-benzimidazol-2(3H)-one

Belaziz, D.; Kandri Rodi, Y.; Ouazzani Chahdi, F.; Essassi, E.M.; Saadi, M.; El Ammari, L.

doi:10.1107/S1600536812043620

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3212

doi:10.1107/S1600536812043620

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1-Allyl-1H-1,3-benzimidazol-2(3H)-one

Dounia Belaziz,^a ^* Youssef Kandri Rodi,^a Fouad Ouazzani Chahdi,^a El Mokhtar Essassi,^b,^c Mohamed Saadi ^d and Lahcen El Ammari ^d

^aLaboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'immouzzer, BP 2202 Fès, Morocco, ^bLaboratoire de Chimie Organique Hétérocyclique URAC21, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco, ^cInstitute of Nanmaterials and Nanotechnology, MASCIR, Rabat, Morocco, and ^dLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
^*Correspondence e-mail: d_belaziz@yahoo.fr

(Received 9 October 2012; accepted 21 October 2012; online 27 October 2012)

The fused five- and six-membered rings in the title compound, C₁₀H₁₀N₂O, are approximately coplanar, with an r.m.s. deviation of 0.008 Å. The mean plane of the allyl group is roughly perpendicular to the mean plane of the 1,3-benzimidazol-2(3H)-one system, making a dihedral angle of 86.1 (2)°. In the crystal, each molecule is linked to its symmetry equivalent partner by a pair of N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For the pharmacological and biochemical properties of the title compound, see: Gravatt et al. (1994 ); Horton et al. (2003 ); Kim et al. (1996 ); Roth et al. (1997 ). For compounds with similar structures, see: Belaziz et al. (2012 ); Ouzidan et al. (2011 ).

Experimental

Crystal data

C₁₀H₁₀N₂O
M_r = 174.20
Monoclinic, P 2₁ /c
a = 10.2749 (5) Å
b = 5.5787 (3) Å
c = 16.6220 (9) Å
β = 100.976 (4)°
V = 935.35 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.38 × 0.29 × 0.27 mm

Data collection

Bruker X8 APEX diffractometer
13429 measured reflections
2570 independent reflections
1393 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.128
S = 1.04
2570 reflections
120 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1ⁱ	0.86	2.00	2.8274 (14)	161
C3—H3⋯O1ⁱⁱ	0.93	2.52	3.3080 (19)	142
Symmetry codes: (i) -x+1, -y, -z+2; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812043620/fj2602sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812043620/fj2602Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812043620/fj2602Isup3.cml

checkCIF report

Comment top

Benzimidazoles are very useful intermediates/subunits for the development of molecules of pharmaceutical or biological interest. Benzimidazole and its derivatives are an important class of bioactive molecules in the field of drugs and pharmaceuticals. Benzimidazole derivatives have found applications in diverse therapeutic areas including anti-ulcers, anti-hypertensives, anti-virals, anti-fungals, anti-cancers, (Gravatt et al. 1994; Horton et al. 2003; Kim et al. 1996; Roth et al. 1997).

As a continuation of our research work devoted to the development of substituted benzimidazol-2-one derivatives (Belaziz et al., 2012; Ouzidan et al. 2011), we reported in this paper the synthesis of new benzimidazol-2-one derivative by action of allyl bromide with 1H-1,3-benzimidazol-2(3H)-one in the presence of a catalytic quantity of tetra-n-butylammonium bromide under mild conditions to furnish mono-substituted compound (Scheme 1).

The crystal structure of the 1-allyl-1H-1,3-benzimidazol-2(3H)-one molecule is built up from fused six-and five-membered rings linked to C₃H₅ chain as shown in Fg.1. The fused-ring system is essentially planar, with a maximum deviation of -0.010 (1) Å for C10. The allyl group is nearly perpendicular to the 1H-1,3-benzimidazol-2(3H)-one plane as indicated by the torsion angle of C8 C7 N1 C6 - 70.44 (18)°. In the crystal, each molecule and its symmetry through the inversion center are linked by N2—H2···O1 and C3—H3···O1 hydrogen bonds in the way to form dimers as shown in Fig.2.

Related literature top

For the pharmacological and biochemical properties of the title compound, see: Gravatt et al. (1994); Horton et al. (2003); Kim et al. (1996); Roth et al. (1997). For compounds with similar structures, see: Belaziz et al. (2012); Ouzidan et al. (2011).

Experimental top

To 1H-1,3-benzimidazol-2(3H)-one (0.2 g, 1.49 mmol), potassium carbonate (0.41 g, 2.98 mmol) and tetra-n-butylammonium bromide (0.05 g, 0.15 mmol) in DMF (15 ml) was added allyl bromide (0.14 ml, 1.78 mmol). Stirring was continued at room temperature for 6 h. The salt was removed by filtration and the filtrate concentrated under reduced pressure. The residue was separated by chromatography on a column of silica gel with ethyl acetate/hexane (1/2) as eluent. The product was obtained with quantitative yield of 70%. It was recrystallized from hexan/acetate to give colourless crystals.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. Molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles.
	Fig. 2. Molecule and its symmetry through the inversion center linked by hydrogen bonds and building dimers.

1-Allyl-1H-1,3-benzimidazol-2(3H)-one top

Crystal data top

C₁₀H₁₀N₂O	F(000) = 368
M_r = 174.20	D_x = 1.237 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 342.7 K
Hall symbol: -p 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.2749 (5) Å	Cell parameters from 2570 reflections
b = 5.5787 (3) Å	θ = 2.9–29.4°
c = 16.6220 (9) Å	µ = 0.08 mm⁻¹
β = 100.976 (4)°	T = 296 K
V = 935.35 (8) Å³	Block, colourless
Z = 4	0.38 × 0.29 × 0.27 mm

Data collection top

Bruker X8 APEX diffractometer	1393 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.046
Graphite monochromator	θ_max = 29.4°, θ_min = 2.9°
ϕ and ω scans	h = −13→14
13429 measured reflections	k = −7→7
2570 independent reflections	l = −22→22

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.128	w = 1/[σ²(F_o²) + (0.0584P)²] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2570 reflections	Δρ_max = 0.14 e Å⁻³
120 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.011 (4)

Crystal data top

C₁₀H₁₀N₂O	V = 935.35 (8) Å³
M_r = 174.20	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.2749 (5) Å	µ = 0.08 mm⁻¹
b = 5.5787 (3) Å	T = 296 K
c = 16.6220 (9) Å	0.38 × 0.29 × 0.27 mm
β = 100.976 (4)°

Data collection top

Bruker X8 APEX diffractometer	1393 reflections with I > 2σ(I)
13429 measured reflections	R_int = 0.046
2570 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 1.04	Δρ_max = 0.14 e Å⁻³
2570 reflections	Δρ_min = −0.14 e Å⁻³
120 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C1	0.64101 (14)	0.3295 (2)	0.87918 (9)	0.0444 (4)
C2	0.63854 (16)	0.3098 (3)	0.79675 (9)	0.0549 (4)
H2A	0.5937	0.1851	0.7662	0.066*
C3	0.70534 (18)	0.4825 (3)	0.76048 (9)	0.0638 (5)
H3	0.7056	0.4732	0.7046	0.077*
C4	0.77162 (19)	0.6684 (3)	0.80584 (10)	0.0651 (5)
H4	0.8153	0.7820	0.7798	0.078*
C5	0.77454 (16)	0.6892 (2)	0.88889 (10)	0.0557 (4)
H5	0.8189	0.8149	0.9191	0.067*
C6	0.70925 (14)	0.5166 (2)	0.92520 (8)	0.0436 (4)
C7	0.74323 (15)	0.6384 (2)	1.07492 (9)	0.0512 (4)
H7A	0.7020	0.5928	1.1205	0.061*
H7B	0.7180	0.8027	1.0605	0.061*
C8	0.88971 (17)	0.6264 (3)	1.10148 (10)	0.0656 (5)
H8	0.9191	0.4602	1.1144	0.105 (7)*
C9	0.9688 (2)	0.8074 (4)	1.11471 (13)	0.0968 (7)
H9A	1.0714	0.7945	1.1346	0.116*
H9B	0.9256	0.9702	1.1048	0.116*
C10	0.61611 (15)	0.2860 (2)	1.01062 (9)	0.0441 (4)
N1	0.69312 (11)	0.48505 (18)	1.00561 (7)	0.0452 (3)
N2	0.58638 (12)	0.19162 (19)	0.93391 (7)	0.0481 (3)
H2	0.5401	0.0640	0.9210	0.058*
O1	0.58255 (11)	0.21105 (17)	1.07330 (6)	0.0559 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0415 (9)	0.0445 (7)	0.0468 (9)	0.0002 (5)	0.0072 (7)	0.0025 (6)
C2	0.0578 (11)	0.0578 (9)	0.0476 (10)	−0.0040 (7)	0.0064 (8)	−0.0033 (6)
C3	0.0733 (13)	0.0750 (11)	0.0442 (9)	−0.0033 (8)	0.0137 (8)	0.0056 (7)
C4	0.0751 (13)	0.0680 (11)	0.0555 (11)	−0.0120 (8)	0.0205 (9)	0.0106 (8)
C5	0.0597 (11)	0.0523 (9)	0.0567 (10)	−0.0101 (7)	0.0149 (8)	0.0027 (6)
C6	0.0417 (9)	0.0443 (7)	0.0451 (8)	0.0006 (6)	0.0091 (6)	0.0028 (5)
C7	0.0556 (11)	0.0511 (8)	0.0483 (9)	−0.0034 (6)	0.0132 (8)	−0.0068 (6)
C8	0.0591 (12)	0.0633 (11)	0.0695 (12)	−0.0024 (8)	0.0001 (9)	−0.0102 (8)
C9	0.0674 (15)	0.0902 (15)	0.130 (2)	−0.0206 (10)	0.0128 (13)	−0.0189 (12)
C10	0.0420 (9)	0.0437 (7)	0.0469 (9)	0.0000 (6)	0.0090 (7)	0.0037 (6)
N1	0.0476 (8)	0.0444 (6)	0.0442 (7)	−0.0063 (5)	0.0106 (6)	−0.0014 (4)
N2	0.0514 (8)	0.0439 (6)	0.0491 (8)	−0.0094 (5)	0.0100 (6)	−0.0008 (5)
O1	0.0631 (8)	0.0575 (6)	0.0491 (7)	−0.0111 (5)	0.0159 (6)	0.0066 (4)

Geometric parameters (Å, º) top

C1—C2	1.370 (2)	C7—N1	1.4487 (17)
C1—N2	1.3890 (17)	C7—C8	1.487 (2)
C1—C6	1.4007 (18)	C7—H7A	0.9700
C2—C3	1.386 (2)	C7—H7B	0.9700
C2—H2A	0.9300	C8—C9	1.288 (2)
C3—C4	1.383 (2)	C8—H8	0.9858
C3—H3	0.9300	C9—H9A	1.0463
C4—C5	1.380 (2)	C9—H9B	1.0104
C4—H4	0.9300	C10—O1	1.2313 (16)
C5—C6	1.3768 (19)	C10—N2	1.3594 (17)
C5—H5	0.9300	C10—N1	1.3751 (17)
C6—N1	1.3890 (16)	N2—H2	0.8600

C2—C1—N2	132.67 (13)	C8—C7—H7A	108.9
C2—C1—C6	121.20 (13)	N1—C7—H7B	108.9
N2—C1—C6	106.13 (12)	C8—C7—H7B	108.9
C1—C2—C3	117.58 (14)	H7A—C7—H7B	107.7
C1—C2—H2A	121.2	C9—C8—C7	125.79 (19)
C3—C2—H2A	121.2	C9—C8—H8	122.9
C4—C3—C2	121.15 (15)	C7—C8—H8	111.0
C4—C3—H3	119.4	C8—C9—H9A	124.4
C2—C3—H3	119.4	C8—C9—H9B	115.7
C5—C4—C3	121.56 (14)	H9A—C9—H9B	119.9
C5—C4—H4	119.2	O1—C10—N2	127.79 (13)
C3—C4—H4	119.2	O1—C10—N1	125.63 (13)
C6—C5—C4	117.39 (14)	N2—C10—N1	106.57 (12)
C6—C5—H5	121.3	C10—N1—C6	109.64 (11)
C4—C5—H5	121.3	C10—N1—C7	123.39 (12)
C5—C6—N1	131.91 (13)	C6—N1—C7	126.93 (11)
C5—C6—C1	121.11 (13)	C10—N2—C1	110.67 (12)
N1—C6—C1	106.97 (11)	C10—N2—H2	124.7
N1—C7—C8	113.31 (12)	C1—N2—H2	124.7
N1—C7—H7A	108.9

N2—C1—C2—C3	−179.87 (15)	N2—C10—N1—C6	1.06 (15)
C6—C1—C2—C3	−0.4 (2)	O1—C10—N1—C7	−1.5 (2)
C1—C2—C3—C4	−0.2 (3)	N2—C10—N1—C7	178.85 (12)
C2—C3—C4—C5	0.3 (3)	C5—C6—N1—C10	178.59 (15)
C3—C4—C5—C6	0.3 (3)	C1—C6—N1—C10	−0.59 (15)
C4—C5—C6—N1	179.99 (14)	C5—C6—N1—C7	0.9 (2)
C4—C5—C6—C1	−0.9 (2)	C1—C6—N1—C7	−178.28 (13)
C2—C1—C6—C5	1.0 (2)	C8—C7—N1—C10	112.16 (16)
N2—C1—C6—C5	−179.39 (13)	C8—C7—N1—C6	−70.44 (18)
C2—C1—C6—N1	−179.73 (12)	O1—C10—N2—C1	179.19 (14)
N2—C1—C6—N1	−0.11 (15)	N1—C10—N2—C1	−1.14 (15)
N1—C7—C8—C9	130.56 (19)	C2—C1—N2—C10	−179.66 (15)
O1—C10—N1—C6	−179.26 (13)	C6—C1—N2—C10	0.79 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.86	2.00	2.8274 (14)	161
C3—H3···O1ⁱⁱ	0.93	2.52	3.3080 (19)	142

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

Experimental details

Crystal data
Chemical formula	C₁₀H₁₀N₂O
M_r	174.20
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.2749 (5), 5.5787 (3), 16.6220 (9)
β (°)	100.976 (4)
V (Å³)	935.35 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.38 × 0.29 × 0.27

Data collection
Diffractometer	Bruker X8 APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13429, 2570, 1393
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.690

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.128, 1.04
No. of reflections	2570
No. of parameters	120
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.14

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.86	2.00	2.8274 (14)	161
C3—H3···O1ⁱⁱ	0.93	2.52	3.3080 (19)	142

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

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

References

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