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

Saber, A.; Zouihri, H.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536810017897

organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page o1409

https://doi.org/10.1107/S1600536810017897

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

Asmaa Saber,^a Hafid Zouihri,^b El Mokhtar Essassi ^a and Seik Weng Ng ^c ^*

^aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, ^bCNRST Division UATRS, Angle Allal Fassi/FAR, BP 8027 Hay Riad, Rabat, Morocco, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 27 April 2010; accepted 14 May 2010; online 22 May 2010)

In the title N-substituted benzimidazol-2-one, C₁₀H₁₀N₂O, the fused ring system is almost planar (r.m.s. deviation = 0.01 Å) and aligned at 57.9 (1)° with respect to the propenyl fragment. In the crystal, adjacent molecules are linked by pairs of N—H⋯O hydrogen bonds into inversion dimers.

Related literature

For the transformation of 1-isopropenyl-1,3-benzimidazol-2-one to other biologically-active compounds, see: Lakhrissi et al. (2010 ); Li et al. (2010 ). A shorter heating time in the synthesis leads to the formation of 4-methyl-2,3-dihydro-1H-1,5-benzodiazepin-2-one; see: Saber et al. (2010 ).

Experimental

Crystal data

C₁₀H₁₀N₂O
M_r = 174.20
Monoclinic, C 2/c
a = 15.8724 (2) Å
b = 6.0971 (1) Å
c = 17.9313 (3) Å
β = 90.961 (2)°
V = 1735.07 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.35 × 0.30 × 0.18 mm

Data collection

Bruker X8 APEXII diffractometer
13930 measured reflections
2506 independent reflections
2231 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.114
S = 0.98
2506 reflections
123 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.87 (1)	1.95 (1)	2.811 (1)	172 (2)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810017897/nc2184sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810017897/nc2184Isup2.hkl

checkCIF report

Comment top

Benzimidazol-2-one derivatives possess a range of biological and pharmacological activities. Among the many compounds is N-isopropenyl benzimidazol-2-one, which can be further converted to 1-acyl-3-isopropenyl benzimidazol-2-ones that are active against Botrytis cinerea fungi that affect vegetables and fruits (Li et al. 2010). The reagent is also commercially available. We have recently reported the use of this reagent in the synthesis of some glucose-substituted benzimidazol-2-ones (Lakhrissi et al., 2010). For the purpose of understanding the chemistry of these compounds, the crystal structure of the reagent is determined in the present study.

In the molecule of C₁₀H₁₀N₂O (Scheme I, Fig. 1), the fused-ring is planar (r.m.s. deviation 0.01 Å); the propenyl fragment is aligned at 57.9 (1) ° with respect to the fused-ring. Adjacent molecules are linked about a center-of-inversion by an N–H···O hydrogen bond.

Related literature top

For the transformation of 1-isopropenyl-1,3-benzimidazol-2-one to other biologically-active compounds, see: Lakhrissi et al. (2010); Li et al. (2010). A shorter heating time in the synthesis leads to the formation of 4-methyl-2,3-dihydro-1H-1,5-benzodiazepin-2-one; see: Saber et al. (2010).

Experimental top

o-Phenylenediamine (1.0 g, 9 mmol) and ethyl acetoacetate (1.2 ml, 9 mmol) were heated in xylene (10 ml) for 6 hours. The mixture was set aside for the growth of colorless crystals of N-isopropenyl benzimidazol-2-one; yield 90%. When the heating time is shortened to 1 hour, the product is 4-methyl-2,3-dihydro-1H-1,5-benzodiazepin-2-one; details are given in another report (Saber et al., 2010).

Structure description top

For the transformation of 1-isopropenyl-1,3-benzimidazol-2-one to other biologically-active compounds, see: Lakhrissi et al. (2010); Li et al. (2010). A shorter heating time in the synthesis leads to the formation of 4-methyl-2,3-dihydro-1H-1,5-benzodiazepin-2-one; see: Saber et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the molecule of C₁₀H₁₀N₂O at the 70% probability level shown as a hydrogen-bonded dimer; hydrogen atoms are drawn as spheres of arbitrary radius. Symmetry code: i = 1 - x, 1 - y, 1 - z.

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

Crystal data top

C₁₀H₁₀N₂O	F(000) = 736
M_r = 174.20	D_x = 1.334 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8296 reflections
a = 15.8724 (2) Å	θ = 2.3–35.0°
b = 6.0971 (1) Å	µ = 0.09 mm⁻¹
c = 17.9313 (3) Å	T = 100 K
β = 90.961 (2)°	Block, colorless
V = 1735.07 (5) Å³	0.35 × 0.30 × 0.18 mm
Z = 8

Data collection top

Bruker X8 APEXII diffractometer	2231 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 30.0°, θ_min = 3.4°
φ and ω scans	h = −21→21
13930 measured reflections	k = −8→8
2506 independent reflections	l = −25→25

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ²(F_o²) + (0.0716P)² + 0.9009P] where P = (F_o² + 2F_c²)/3
2506 reflections	(Δ/σ)_max = 0.001
123 parameters	Δρ_max = 0.39 e Å⁻³
1 restraint	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₀H₁₀N₂O	V = 1735.07 (5) Å³
M_r = 174.20	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 15.8724 (2) Å	µ = 0.09 mm⁻¹
b = 6.0971 (1) Å	T = 100 K
c = 17.9313 (3) Å	0.35 × 0.30 × 0.18 mm
β = 90.961 (2)°

Data collection top

Bruker X8 APEXII diffractometer	2231 reflections with I > 2σ(I)
13930 measured reflections	R_int = 0.023
2506 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	1 restraint
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	Δρ_max = 0.39 e Å⁻³
2506 reflections	Δρ_min = −0.21 e Å⁻³
123 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.58630 (4)	0.41270 (11)	0.43646 (4)	0.02815 (17)
N1	0.45280 (5)	0.26700 (13)	0.45678 (4)	0.02451 (18)
H1	0.4355 (10)	0.366 (2)	0.4880 (7)	0.048 (4)*
N2	0.53743 (5)	0.08911 (12)	0.38109 (4)	0.02211 (17)
C1	0.40921 (5)	0.08279 (14)	0.43226 (5)	0.02174 (18)
C2	0.32851 (6)	0.00950 (17)	0.44634 (5)	0.0275 (2)
H2	0.2922	0.0883	0.4783	0.033*
C3	0.30248 (6)	−0.18432 (17)	0.41176 (6)	0.0296 (2)
H3	0.2473	−0.2386	0.4201	0.036*
C4	0.35602 (6)	−0.29936 (17)	0.36524 (6)	0.0296 (2)
H4	0.3367	−0.4314	0.3426	0.035*
C5	0.43747 (6)	−0.22577 (15)	0.35092 (5)	0.0259 (2)
H5	0.4740	−0.3051	0.3193	0.031*
C6	0.46266 (5)	−0.03240 (14)	0.38485 (4)	0.02048 (18)
C7	0.53105 (6)	0.27304 (14)	0.42624 (5)	0.02226 (18)
C8	0.60775 (5)	0.04385 (15)	0.33453 (5)	0.02371 (19)
C9	0.64627 (6)	−0.14799 (17)	0.33983 (6)	0.0338 (2)
H9A	0.6272	−0.2545	0.3743	0.041*
H9B	0.6930	−0.1793	0.3091	0.041*
C10	0.62872 (7)	0.21916 (17)	0.27950 (6)	0.0327 (2)
H10A	0.6743	0.1682	0.2476	0.049*
H10B	0.6469	0.3517	0.3062	0.049*
H10C	0.5788	0.2524	0.2487	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0268 (3)	0.0240 (3)	0.0338 (4)	−0.0062 (2)	0.0053 (3)	−0.0065 (3)
N1	0.0231 (4)	0.0223 (4)	0.0284 (4)	−0.0013 (3)	0.0057 (3)	−0.0049 (3)
N2	0.0214 (4)	0.0209 (3)	0.0242 (3)	−0.0038 (3)	0.0054 (3)	−0.0036 (3)
C1	0.0218 (4)	0.0219 (4)	0.0216 (4)	−0.0003 (3)	0.0012 (3)	0.0005 (3)
C2	0.0215 (4)	0.0315 (5)	0.0298 (4)	−0.0009 (3)	0.0044 (3)	−0.0010 (3)
C3	0.0222 (4)	0.0350 (5)	0.0316 (5)	−0.0075 (3)	0.0017 (3)	0.0001 (4)
C4	0.0282 (5)	0.0304 (5)	0.0302 (4)	−0.0090 (4)	0.0004 (3)	−0.0036 (4)
C5	0.0265 (4)	0.0258 (4)	0.0255 (4)	−0.0044 (3)	0.0034 (3)	−0.0044 (3)
C6	0.0199 (4)	0.0216 (4)	0.0200 (4)	−0.0022 (3)	0.0016 (3)	0.0008 (3)
C7	0.0234 (4)	0.0204 (4)	0.0230 (4)	−0.0008 (3)	0.0027 (3)	−0.0013 (3)
C8	0.0215 (4)	0.0263 (4)	0.0235 (4)	−0.0056 (3)	0.0057 (3)	−0.0045 (3)
C9	0.0292 (5)	0.0292 (5)	0.0433 (6)	−0.0002 (4)	0.0114 (4)	−0.0055 (4)
C10	0.0352 (5)	0.0346 (5)	0.0287 (5)	−0.0088 (4)	0.0090 (4)	0.0014 (4)

Geometric parameters (Å, º) top

O1—C7	1.2338 (11)	C3—H3	0.9500
N1—C7	1.3663 (11)	C4—C5	1.3963 (13)
N1—C1	1.3868 (11)	C4—H4	0.9500
N1—H1	0.871 (9)	C5—C6	1.3827 (12)
N2—C7	1.3878 (11)	C5—H5	0.9500
N2—C6	1.4016 (10)	C8—C9	1.3225 (14)
N2—C8	1.4319 (11)	C8—C10	1.4960 (13)
C1—C2	1.3839 (12)	C9—H9A	0.9500
C1—C6	1.3999 (11)	C9—H9B	0.9500
C2—C3	1.3939 (14)	C10—H10A	0.9800
C2—H2	0.9500	C10—H10B	0.9800
C3—C4	1.3907 (14)	C10—H10C	0.9800

C7—N1—C1	110.29 (7)	C4—C5—H5	121.5
C7—N1—H1	122.5 (11)	C5—C6—C1	121.42 (8)
C1—N1—H1	127.2 (11)	C5—C6—N2	131.94 (8)
C7—N2—C6	109.21 (7)	C1—C6—N2	106.63 (7)
C7—N2—C8	124.13 (7)	O1—C7—N1	127.42 (8)
C6—N2—C8	126.52 (7)	O1—C7—N2	125.86 (8)
C2—C1—N1	131.46 (8)	N1—C7—N2	106.72 (7)
C2—C1—C6	121.39 (8)	C9—C8—N2	119.50 (8)
N1—C1—C6	107.14 (7)	C9—C8—C10	124.87 (9)
C1—C2—C3	117.45 (9)	N2—C8—C10	115.54 (8)
C1—C2—H2	121.3	C8—C9—H9A	120.0
C3—C2—H2	121.3	C8—C9—H9B	120.0
C4—C3—C2	120.99 (9)	H9A—C9—H9B	120.0
C4—C3—H3	119.5	C8—C10—H10A	109.5
C2—C3—H3	119.5	C8—C10—H10B	109.5
C3—C4—C5	121.69 (9)	H10A—C10—H10B	109.5
C3—C4—H4	119.2	C8—C10—H10C	109.5
C5—C4—H4	119.2	H10A—C10—H10C	109.5
C6—C5—C4	117.05 (9)	H10B—C10—H10C	109.5
C6—C5—H5	121.5

C7—N1—C1—C2	−178.46 (10)	C8—N2—C6—C5	4.24 (15)
C7—N1—C1—C6	0.49 (10)	C7—N2—C6—C1	1.11 (10)
N1—C1—C2—C3	179.14 (9)	C8—N2—C6—C1	−174.64 (8)
C6—C1—C2—C3	0.31 (14)	C1—N1—C7—O1	−179.45 (9)
C1—C2—C3—C4	0.29 (15)	C1—N1—C7—N2	0.19 (10)
C2—C3—C4—C5	−0.32 (16)	C6—N2—C7—O1	178.83 (9)
C3—C4—C5—C6	−0.25 (15)	C8—N2—C7—O1	−5.29 (15)
C4—C5—C6—C1	0.85 (13)	C6—N2—C7—N1	−0.81 (10)
C4—C5—C6—N2	−177.89 (9)	C8—N2—C7—N1	175.06 (8)
C2—C1—C6—C5	−0.91 (13)	C7—N2—C8—C9	127.09 (10)
N1—C1—C6—C5	−179.99 (8)	C6—N2—C8—C9	−57.76 (13)
C2—C1—C6—N2	178.11 (8)	C7—N2—C8—C10	−56.22 (12)
N1—C1—C6—N2	−0.97 (9)	C6—N2—C8—C10	118.93 (9)
C7—N2—C6—C5	179.99 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.87 (1)	1.95 (1)	2.811 (1)	172 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₀N₂O
M_r	174.20
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	15.8724 (2), 6.0971 (1), 17.9313 (3)
β (°)	90.961 (2)
V (Å³)	1735.07 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.35 × 0.30 × 0.18

Data collection
Diffractometer	Bruker X8 APEXII
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13930, 2506, 2231
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.114, 0.98
No. of reflections	2506
No. of parameters	123
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.21

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.87 (1)	1.947 (9)	2.811 (1)	171.6 (15)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

We thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lakhrissi, B., Benksim, A., Massoui, M., Essassi, E. M., Lequart, V., Joly, N., Beaupeŕe, D., Wadouachi, A. & Martin, P. (2010). Carbohydr. Res. 343, 421–433. Web of Science CrossRef Google Scholar
Li, S.-K., Ji, Z.-Q., Zhang, J.-W., Guo, Z.-Y. & Wu, W.-J. (2010). J. Agric. Food Chem. 58, 2668–2672. Web of Science CrossRef CAS PubMed Google Scholar
Saber, A., Zouihri, H., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o1408. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43. Submitted. Google Scholar