1,3-Diallyl-5-chloro-1H-benzimidazol-2(3H)-one

Ouzidan, Y.; Kandri Rodi, Y.; Saffon, N.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536811003035

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o520

doi:10.1107/S1600536811003035

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1,3-Diallyl-5-chloro-1H-benzimidazol-2(3H)-one

Younes Ouzidan,^a Y. Kandri Rodi,^a Natalie Saffon,^b El Mokhtar Essassi ^c and Seik Weng Ng ^d ^*

^aLaboratoire de Chimie Organique Appliquée, Faculté des Sciences et Techniques, Université Sidi Mohamed Ben Abdallah, Fés, Morocco, ^bService Commun Rayons-X FR2599, Université Paul Sabatier Bâtiment 2R1, 118 route de Narbonne, Toulouse, France, ^cLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 19 January 2011; accepted 23 January 2011; online 29 January 2011)

The benzimidazolone part of the title molecule, C₁₃H₁₃ClN₂O, is almost planar (r.m.s. deviation = 0.006 Å) and its mean plane is aligned at dihedral angles of 62.5 (1) and 78.0 (1)° with respect to the mean planes of the allyl substituents.

Related literature

For the synthesis, see: Vernin et al. (1981 ).

Experimental

Crystal data

C₁₃H₁₃ClN₂O
M_r = 248.70
Monoclinic, P 2₁ /c
a = 7.8831 (1) Å
b = 15.2481 (3) Å
c = 10.3593 (2) Å
β = 93.056 (1)°
V = 1243.44 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 295 K
0.35 × 0.20 × 0.20 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ) T_min = 0.905, T_max = 0.944
17723 measured reflections
2858 independent reflections
2230 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.156
S = 1.03
2858 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.98 e Å⁻³
Δρ_min = −0.34 e Å⁻³

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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811003035/jh2259sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811003035/jh2259Isup2.hkl

checkCIF report

Comment top

Tetraalkylammonium halides are used as phase-transfer catalyst in the synthesis of 1,3-dialkyl-1,2-benzimidazolones, butyltriethylammonium chloride being used in the synthesis of the 1,3-diallyl derivative (Vernin et al., 1981). Thhis compound as well as its derivatives possess pharmalogically important properties. The title chlorine-substitutent compound (Scheme I) was synthesized for evaluation of such properties. The benzimidazolone part of the C₁₃H₁₃ClN₂O molecule (Fig. 1) is planar (r.m.s. deviation 0.006 Å); its mean plane is aligned at 62.5 (1) and 78.0 (1) with respect to the mean planes of the allyl substituents.

Related literature top

For the synthesis, see: Vernin et al. (1981).

Experimental top

To 5-chloro-1H-benzo[d]imidazol-2(3H)-one (0.2 g, 1.18 mmol), potassium carbonate (0.4 g, 2.8 mmol), and tetra-n-butylammonium bromide (0.08 g, 0.23 mmol) in DMF (15 ml) was added allyl-bromide (0.22 ml, 2.6 mmol). Stirring was continued at room temperature for 6 h. The salts were 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. Colorless crystals were isolated when the solvent was allowed to evaporate.

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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₁₃H₁₃ClN₂O at the 50% probability level; hydrogen atoms are drawn as arbitrary radius.

1,3-Diallyl-5-chloro-1H-benzimidazol-2(3H)-one top

Crystal data top

C₁₃H₁₃ClN₂O	F(000) = 520
M_r = 248.70	D_x = 1.329 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4645 reflections
a = 7.8831 (1) Å	θ = 2.4–29.0°
b = 15.2481 (3) Å	µ = 0.29 mm⁻¹
c = 10.3593 (2) Å	T = 295 K
β = 93.056 (1)°	Block, colourless
V = 1243.44 (4) Å³	0.35 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	2858 independent reflections
Radiation source: fine-focus sealed tube	2230 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −10→10
T_min = 0.905, T_max = 0.944	k = −19→19
17723 measured reflections	l = −12→13

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) = 0.156	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0846P)² + 0.6164P] where P = (F_o² + 2F_c²)/3
2858 reflections	(Δ/σ)_max = 0.001
154 parameters	Δρ_max = 0.98 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₃H₁₃ClN₂O	V = 1243.44 (4) Å³
M_r = 248.70	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.8831 (1) Å	µ = 0.29 mm⁻¹
b = 15.2481 (3) Å	T = 295 K
c = 10.3593 (2) Å	0.35 × 0.20 × 0.20 mm
β = 93.056 (1)°

Data collection top

Bruker APEXII diffractometer	2858 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	2230 reflections with I > 2σ(I)
T_min = 0.905, T_max = 0.944	R_int = 0.033
17723 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.156	H-atom parameters constrained
S = 1.03	Δρ_max = 0.98 e Å⁻³
2858 reflections	Δρ_min = −0.34 e Å⁻³
154 parameters

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

	x	y	z	U_iso*/U_eq
Cl1	0.25390 (9)	0.66457 (5)	0.19928 (6)	0.0609 (2)
O1	0.6243 (2)	0.62064 (10)	0.86933 (14)	0.0468 (4)
N1	0.5616 (2)	0.66732 (10)	0.65711 (15)	0.0341 (4)
N2	0.4252 (2)	0.55197 (10)	0.72844 (15)	0.0340 (4)
C1	0.4530 (2)	0.63903 (12)	0.55655 (17)	0.0304 (4)
C2	0.4221 (2)	0.67167 (12)	0.43253 (18)	0.0346 (4)
H2	0.4781	0.7208	0.4029	0.042*
C3	0.3021 (3)	0.62631 (14)	0.35525 (19)	0.0388 (5)
C4	0.2168 (3)	0.55288 (14)	0.3964 (2)	0.0407 (5)
H4	0.1391	0.5244	0.3403	0.049*
C5	0.2476 (2)	0.52151 (13)	0.5227 (2)	0.0371 (4)
H5	0.1904	0.4728	0.5526	0.045*
C6	0.3663 (2)	0.56580 (12)	0.60094 (17)	0.0307 (4)
C7	0.5461 (3)	0.61349 (12)	0.76399 (18)	0.0348 (4)
C8	0.6889 (3)	0.73629 (13)	0.6498 (2)	0.0385 (5)
H8A	0.7127	0.7607	0.7353	0.046*
H8B	0.6442	0.7829	0.5941	0.046*
C9	0.8507 (3)	0.70238 (14)	0.5983 (2)	0.0438 (5)
H9	0.9055	0.6560	0.6414	0.053*
C10	0.9186 (3)	0.73440 (16)	0.4965 (3)	0.0548 (6)
H10A	0.8664	0.7808	0.4516	0.066*
H10B	1.0192	0.7109	0.4687	0.066*
C11	0.3710 (3)	0.48204 (13)	0.8125 (2)	0.0410 (5)
H11A	0.4544	0.4757	0.8842	0.049*
H11B	0.3681	0.4274	0.7645	0.049*
C12	0.2008 (3)	0.49716 (17)	0.8649 (2)	0.0561 (7)
H12	0.1536	0.4507	0.9088	0.067*
C13	0.1120 (4)	0.5692 (2)	0.8550 (3)	0.0647 (8)
H13A	0.1540	0.6174	0.8120	0.078*
H13B	0.0066	0.5723	0.8911	0.078*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0596 (4)	0.0792 (5)	0.0427 (3)	−0.0024 (3)	−0.0096 (3)	0.0139 (3)
O1	0.0592 (10)	0.0442 (8)	0.0362 (7)	−0.0043 (7)	−0.0055 (7)	0.0002 (6)
N1	0.0399 (9)	0.0296 (8)	0.0326 (8)	−0.0039 (6)	0.0018 (7)	−0.0010 (6)
N2	0.0393 (9)	0.0291 (8)	0.0339 (8)	−0.0015 (6)	0.0054 (6)	0.0019 (6)
C1	0.0300 (9)	0.0290 (8)	0.0329 (9)	0.0024 (7)	0.0062 (7)	−0.0024 (7)
C2	0.0335 (10)	0.0357 (10)	0.0352 (9)	0.0027 (7)	0.0070 (8)	0.0034 (7)
C3	0.0355 (10)	0.0477 (11)	0.0335 (9)	0.0087 (8)	0.0041 (8)	0.0005 (8)
C4	0.0320 (10)	0.0473 (11)	0.0427 (11)	−0.0002 (8)	0.0013 (8)	−0.0081 (9)
C5	0.0332 (10)	0.0350 (9)	0.0437 (10)	−0.0031 (8)	0.0069 (8)	−0.0039 (8)
C6	0.0303 (9)	0.0288 (8)	0.0336 (9)	0.0028 (7)	0.0071 (7)	−0.0023 (7)
C7	0.0406 (10)	0.0288 (9)	0.0351 (9)	0.0020 (8)	0.0043 (8)	−0.0014 (7)
C8	0.0465 (12)	0.0300 (9)	0.0391 (10)	−0.0081 (8)	0.0024 (8)	−0.0036 (8)
C9	0.0348 (11)	0.0325 (10)	0.0627 (13)	−0.0023 (8)	−0.0097 (9)	0.0045 (9)
C10	0.0429 (13)	0.0474 (12)	0.0750 (17)	−0.0005 (10)	0.0119 (11)	−0.0051 (12)
C11	0.0500 (12)	0.0313 (10)	0.0424 (11)	0.0032 (8)	0.0094 (9)	0.0089 (8)
C12	0.0663 (16)	0.0553 (14)	0.0492 (13)	0.0046 (12)	0.0263 (12)	0.0163 (10)
C13	0.0656 (17)	0.0776 (18)	0.0535 (14)	0.0202 (14)	0.0259 (13)	0.0098 (13)

Geometric parameters (Å, º) top

Cl1—C3	1.741 (2)	C5—H5	0.9300
O1—C7	1.229 (2)	C8—C9	1.501 (3)
N1—C1	1.382 (2)	C8—H8A	0.9700
N1—C7	1.389 (2)	C8—H8B	0.9700
N1—C8	1.459 (2)	C9—C10	1.303 (3)
N2—C7	1.373 (3)	C9—H9	0.9300
N2—C6	1.393 (2)	C10—H10A	0.9300
N2—C11	1.455 (2)	C10—H10B	0.9300
C1—C2	1.387 (3)	C11—C12	1.492 (3)
C1—C6	1.400 (3)	C11—H11A	0.9700
C2—C3	1.390 (3)	C11—H11B	0.9700
C2—H2	0.9300	C12—C13	1.303 (4)
C3—C4	1.385 (3)	C12—H12	0.9300
C4—C5	1.402 (3)	C13—H13A	0.9300
C4—H4	0.9300	C13—H13B	0.9300
C5—C6	1.381 (3)

C1—N1—C7	109.83 (16)	N2—C7—N1	106.21 (16)
C1—N1—C8	125.89 (16)	N1—C8—C9	111.75 (16)
C7—N1—C8	123.90 (17)	N1—C8—H8A	109.3
C7—N2—C6	110.02 (15)	C9—C8—H8A	109.3
C7—N2—C11	124.17 (17)	N1—C8—H8B	109.3
C6—N2—C11	125.80 (17)	C9—C8—H8B	109.3
N1—C1—C2	131.12 (17)	H8A—C8—H8B	107.9
N1—C1—C6	107.17 (16)	C10—C9—C8	123.5 (2)
C2—C1—C6	121.71 (18)	C10—C9—H9	118.2
C3—C2—C1	115.81 (18)	C8—C9—H9	118.2
C3—C2—H2	122.1	C9—C10—H10A	120.0
C1—C2—H2	122.1	C9—C10—H10B	120.0
C4—C3—C2	123.46 (19)	H10A—C10—H10B	120.0
C4—C3—Cl1	118.11 (17)	N2—C11—C12	113.75 (17)
C2—C3—Cl1	118.43 (16)	N2—C11—H11A	108.8
C3—C4—C5	120.04 (19)	C12—C11—H11A	108.8
C3—C4—H4	120.0	N2—C11—H11B	108.8
C5—C4—H4	120.0	C12—C11—H11B	108.8
C6—C5—C4	117.31 (18)	H11A—C11—H11B	107.7
C6—C5—H5	121.3	C13—C12—C11	126.3 (2)
C4—C5—H5	121.3	C13—C12—H12	116.9
C5—C6—N2	131.58 (17)	C11—C12—H12	116.9
C5—C6—C1	121.65 (18)	C12—C13—H13A	120.0
N2—C6—C1	106.76 (16)	C12—C13—H13B	120.0
O1—C7—N2	127.35 (18)	H13A—C13—H13B	120.0
O1—C7—N1	126.44 (18)

C7—N1—C1—C2	179.23 (19)	C2—C1—C6—C5	1.1 (3)
C8—N1—C1—C2	−7.7 (3)	N1—C1—C6—N2	0.17 (19)
C7—N1—C1—C6	0.2 (2)	C2—C1—C6—N2	−178.95 (16)
C8—N1—C1—C6	173.33 (17)	C6—N2—C7—O1	179.96 (19)
N1—C1—C2—C3	−179.86 (18)	C11—N2—C7—O1	−1.2 (3)
C6—C1—C2—C3	−1.0 (3)	C6—N2—C7—N1	0.6 (2)
C1—C2—C3—C4	−0.1 (3)	C11—N2—C7—N1	179.50 (16)
C1—C2—C3—Cl1	178.90 (14)	C1—N1—C7—O1	−179.86 (19)
C2—C3—C4—C5	1.1 (3)	C8—N1—C7—O1	6.9 (3)
Cl1—C3—C4—C5	−177.91 (15)	C1—N1—C7—N2	−0.5 (2)
C3—C4—C5—C6	−1.0 (3)	C8—N1—C7—N2	−173.81 (16)
C4—C5—C6—N2	179.97 (18)	C1—N1—C8—C9	−83.2 (2)
C4—C5—C6—C1	−0.1 (3)	C7—N1—C8—C9	88.9 (2)
C7—N2—C6—C5	179.44 (19)	N1—C8—C9—C10	122.9 (2)
C11—N2—C6—C5	0.6 (3)	C7—N2—C11—C12	104.9 (2)
C7—N2—C6—C1	−0.5 (2)	C6—N2—C11—C12	−76.4 (3)
C11—N2—C6—C1	−179.34 (17)	N2—C11—C12—C13	−9.0 (4)
N1—C1—C6—C5	−179.79 (17)

Experimental details

Crystal data
Chemical formula	C₁₃H₁₃ClN₂O
M_r	248.70
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	7.8831 (1), 15.2481 (3), 10.3593 (2)
β (°)	93.056 (1)
V (Å³)	1243.44 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.35 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1997)
T_min, T_max	0.905, 0.944
No. of measured, independent and observed [I > 2σ(I)] reflections	17723, 2858, 2230
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.156, 1.03
No. of reflections	2858
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.98, −0.34

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

We thank Université Sidi Mohamed Ben Abdallah, Université Mohammed V-Agdal and the University of Malaya for supporting this study.

References

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