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access1,3-Dibenzyl-1H-benzimidazol-2(3H)-one
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, Av. Ibn Battouta, BP 1014, Rabat, Morocco, cDepartamento de Quimica Inorganica & Organica, ESTCE, Universitat Jaume I, E-12080 Castellon, Spain, dInstitut für Anorganische Chemie, J.W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany, and eLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
*Correspondence e-mail: ouazzani_chahid@yahoo.fr
In the molecular structure of the title compound, C21H18N2O, the fused-ring system is essentially planar, the largest deviation from the mean plane being 0.0121 (9) Å. The O atom and adjacent C atom are located in 4e on a twofold axis (0, y, 1/4). The two benzyl groups are almost perpendicular to the benzimidazole plane, but point in opposite directions. The dihedral angle between the benzimidazole mean plane and the phenyl ring is 81.95 (5)°, whereas that between the two benzyl groups is 60.96 (7)°.
Related literature
For pharmacological and biochemical properties of benzimidazoles, see: Gravatt et al. (1994![[Gravatt, G. L., Baguley, B. C., Wilson, W. R. & Denny, W. A. (1994). J. Med. Chem. 37, 4338-4345.]](../../../../../../logos/arrows/e_arr.gif "Gravatt, G. L., Baguley, B. C., Wilson, W. R. & Denny, W. A. (1994). J. Med. Chem. 37, 4338-4345.")
); Horton et al. (2003); Kim et al. (1996); Roth et al. (1997). Ouzidan et al. (2011a,b,c).
![[Scheme 1]](im2334scheme1.gif)
Experimental
Crystal data
|
Data collection
Data collection: CrysAlis PRO (Agilent, 2011); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.
Supporting information
contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811046071/im2334sup1.cif
Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811046071/im2334Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536811046071/im2334Isup3.cml
To a mxture of 1H-benzimidazol-2(3H)-one (0.2 g, 1.5 mmol), potassium carbonate (0.41 g, 3 mmol) and tetra-n-butylammonium bromide (0.05 g, 0.15 mmol) in DMF (15 ml) was added benzyl chloride (0.34 ml, 3 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 on a column of silica gel with ethyl acetate/hexane (1/2) as The compound was recrystallized from ethanol to give colourless crystals (yield: 75%).
H atoms were located in a difference map and treated as riding with C—H = 0.93 Å for all H atoms with Uiso(H) = 1.2 Ueqfor aromatic and methylene.
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 (Ouzidan et al., 2011a, 2011b), we reported the synthesis of new benzimidazol-2-one derivative by action of benzyl chloride with 1H-benzimidazol-2(3H)-one in the presence of a catalytic quantity of tetra-n-butylammonium bromide under mild conditions to furnish two compounds: mono-substituted (Ouzidan et al., 2011c) and the title compound (Scheme 1).
The title compound C21H18N2O is a new heterocyclic system deriving from benzimidazole. The of this molecule is built up from two fused six and five-membered rings linked to two benzyl groups. The oxygen and the adjacent carbon atom are located in the 4 e on the twofold axis (0, y, 1/4). The fused-ring system is essentially planar, with the maximum deviation of 0.0121 (9) Å for N1 as shown in Fig.1. The benzyl groups are almost perpendicular to the benzimidazole plane but oriented in opposite directions, with a dihedral angle of 81.95 (7). The dihedral angle between the two benzyl rings is abut 60.965 (7)°.
For pharmacological and biochemical properties of benzimidazoles, see: Gravatt et al. (1994); Horton et al. (2003); Kim et al. (1996); Roth et al. (1997). Ouzidan et al. (2011a,b,c).
Data collection: CrysAlis PRO (Agilent, 2011); cell CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./im2334fig1thm.gif) | 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. |
| C21H18N2O | F(000) = 664 |
| Mr = 314.37 | Dx = 1.294 Mg m−3 |
| Monoclinic, C2/c | Cu Kα radiation, λ = 1.54184 Å |
| Hall symbol: -C 2yc | Cell parameters from 5000 reflections |
| a = 19.5983 (7) Å | θ = 5–50° |
| b = 9.0882 (2) Å | µ = 0.63 mm−1 |
| c = 10.0473 (3) Å | T = 200 K |
| β = 115.593 (4)° | Block, colourless |
| V = 1613.98 (10) Å3 | 0.37 × 0.21 × 0.15 mm |
| Z = 4 |
| Agilent SuperNova Dual Cu at zero Atlas diffractometer | 1611 independent reflections |
| Radiation source: SuperNova (Cu) X-ray Source | 1397 reflections with I > 2σ(I) |
| Mirror monochromator | Rint = 0.028 |
| Detector resolution: 10.4051 pixels mm-1 | θmax = 73.4°, θmin = 5.0° |
| ω scans | h = −23→18 |
| Absorption correction: multi-scan [CrysAlis PRO (Agilent, 2011), using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm (Clark & Reid (1995)] | k = −11→11 |
| Tmin = 0.950, Tmax = 1.000 | l = −12→12 |
| 7837 measured reflections |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
| wR(F2) = 0.106 | w = 1/[σ2(Fo2) + (0.0565P)2 + 0.4305P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.07 | (Δ/σ)max = 0.001 |
| 1611 reflections | Δρmax = 0.15 e Å−3 |
| 111 parameters | Δρmin = −0.16 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: 0.0010 (2) |
| C21H18N2O | V = 1613.98 (10) Å3 |
| Mr = 314.37 | Z = 4 |
| Monoclinic, C2/c | Cu Kα radiation |
| a = 19.5983 (7) Å | µ = 0.63 mm−1 |
| b = 9.0882 (2) Å | T = 200 K |
| c = 10.0473 (3) Å | 0.37 × 0.21 × 0.15 mm |
| β = 115.593 (4)° |
| Agilent SuperNova Dual Cu at zero Atlas diffractometer | 1611 independent reflections |
| Absorption correction: multi-scan [CrysAlis PRO (Agilent, 2011), using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm (Clark & Reid (1995)] | 1397 reflections with I > 2σ(I) |
| Tmin = 0.950, Tmax = 1.000 | Rint = 0.028 |
| 7837 measured reflections |
| R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
| wR(F2) = 0.106 | H-atom parameters constrained |
| S = 1.07 | Δρmax = 0.15 e Å−3 |
| 1611 reflections | Δρmin = −0.16 e Å−3 |
| 111 parameters |
Experimental. CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm (Clark & Reid (1995)). |
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. |
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.5000 | 0.58201 (13) | 0.2500 | 0.0492 (4) | |
| N1 | 0.53746 (5) | 0.35600 (11) | 0.19370 (10) | 0.0366 (3) | |
| C1 | 0.52407 (6) | 0.20943 (12) | 0.21516 (11) | 0.0333 (3) | |
| C2 | 0.54925 (7) | 0.08014 (14) | 0.17958 (13) | 0.0390 (3) | |
| H2 | 0.5835 | 0.0806 | 0.1346 | 0.047* | |
| C3 | 0.52422 (7) | −0.05071 (14) | 0.21593 (14) | 0.0432 (3) | |
| H3 | 0.5402 | −0.1444 | 0.1907 | 0.052* | |
| C4 | 0.5000 | 0.44731 (19) | 0.2500 | 0.0378 (4) | |
| C5 | 0.58741 (7) | 0.40758 (14) | 0.13068 (13) | 0.0412 (3) | |
| H5A | 0.5785 | 0.5117 | 0.1088 | 0.049* | |
| H5B | 0.5751 | 0.3564 | 0.0384 | 0.049* | |
| C11 | 0.67024 (7) | 0.38418 (13) | 0.23142 (12) | 0.0376 (3) | |
| C12 | 0.71696 (8) | 0.30976 (15) | 0.18389 (14) | 0.0459 (3) | |
| H12 | 0.6970 | 0.2694 | 0.0896 | 0.055* | |
| C13 | 0.79366 (8) | 0.29464 (16) | 0.27566 (17) | 0.0522 (4) | |
| H13 | 0.8249 | 0.2450 | 0.2425 | 0.063* | |
| C14 | 0.82333 (8) | 0.35325 (17) | 0.41560 (16) | 0.0518 (4) | |
| H14 | 0.8748 | 0.3445 | 0.4765 | 0.062* | |
| C15 | 0.77703 (8) | 0.42476 (16) | 0.46569 (14) | 0.0507 (4) | |
| H15 | 0.7970 | 0.4626 | 0.5610 | 0.061* | |
| C16 | 0.70099 (8) | 0.44026 (15) | 0.37424 (14) | 0.0450 (3) | |
| H16 | 0.6699 | 0.4888 | 0.4085 | 0.054* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0546 (8) | 0.0361 (7) | 0.0477 (7) | 0.000 | 0.0136 (6) | 0.000 |
| N1 | 0.0302 (5) | 0.0396 (6) | 0.0357 (5) | −0.0023 (4) | 0.0103 (4) | 0.0015 (4) |
| C1 | 0.0233 (5) | 0.0391 (6) | 0.0293 (5) | −0.0018 (4) | 0.0036 (4) | 0.0003 (4) |
| C2 | 0.0295 (6) | 0.0461 (7) | 0.0374 (6) | 0.0012 (5) | 0.0107 (5) | −0.0031 (5) |
| C3 | 0.0371 (7) | 0.0390 (6) | 0.0469 (7) | 0.0015 (5) | 0.0120 (6) | −0.0036 (5) |
| C4 | 0.0329 (9) | 0.0390 (9) | 0.0311 (8) | 0.000 | 0.0038 (7) | 0.000 |
| C5 | 0.0356 (7) | 0.0493 (7) | 0.0337 (6) | −0.0049 (5) | 0.0101 (5) | 0.0064 (5) |
| C11 | 0.0331 (6) | 0.0406 (6) | 0.0349 (6) | −0.0063 (5) | 0.0106 (5) | 0.0064 (5) |
| C12 | 0.0424 (7) | 0.0531 (8) | 0.0415 (6) | −0.0052 (6) | 0.0174 (6) | 0.0003 (6) |
| C13 | 0.0403 (8) | 0.0581 (9) | 0.0592 (8) | 0.0011 (6) | 0.0224 (7) | 0.0053 (7) |
| C14 | 0.0336 (7) | 0.0607 (9) | 0.0511 (8) | −0.0050 (6) | 0.0088 (6) | 0.0129 (6) |
| C15 | 0.0412 (7) | 0.0618 (9) | 0.0377 (7) | −0.0089 (6) | 0.0065 (6) | 0.0011 (6) |
| C16 | 0.0393 (7) | 0.0527 (7) | 0.0397 (7) | −0.0028 (6) | 0.0139 (6) | 0.0000 (6) |
| O1—C4 | 1.224 (2) | C5—H5B | 0.9700 |
| N1—C4 | 1.3807 (14) | C11—C12 | 1.3790 (19) |
| N1—C1 | 1.3924 (15) | C11—C16 | 1.3910 (18) |
| N1—C5 | 1.4541 (15) | C12—C13 | 1.3896 (19) |
| C1—C2 | 1.3801 (17) | C12—H12 | 0.9300 |
| C1—C1i | 1.397 (2) | C13—C14 | 1.376 (2) |
| C2—C3 | 1.3939 (18) | C13—H13 | 0.9300 |
| C2—H2 | 0.9576 | C14—C15 | 1.376 (2) |
| C3—C3i | 1.390 (3) | C14—H14 | 0.9300 |
| C3—H3 | 0.9773 | C15—C16 | 1.3790 (18) |
| C4—N1i | 1.3807 (14) | C15—H15 | 0.9300 |
| C5—C11 | 1.5118 (17) | C16—H16 | 0.9300 |
| C5—H5A | 0.9700 | ||
| C4—N1—C1 | 110.02 (10) | H5A—C5—H5B | 107.8 |
| C4—N1—C5 | 124.18 (11) | C12—C11—C16 | 118.71 (12) |
| C1—N1—C5 | 125.68 (10) | C12—C11—C5 | 121.24 (11) |
| C2—C1—N1 | 131.45 (11) | C16—C11—C5 | 120.04 (12) |
| C2—C1—C1i | 121.63 (7) | C11—C12—C13 | 120.56 (12) |
| N1—C1—C1i | 106.92 (6) | C11—C12—H12 | 119.7 |
| C1—C2—C3 | 116.92 (12) | C13—C12—H12 | 119.7 |
| C1—C2—H2 | 121.4 | C14—C13—C12 | 119.89 (14) |
| C3—C2—H2 | 121.7 | C14—C13—H13 | 120.1 |
| C3i—C3—C2 | 121.44 (8) | C12—C13—H13 | 120.1 |
| C3i—C3—H3 | 119.4 | C13—C14—C15 | 120.15 (13) |
| C2—C3—H3 | 119.1 | C13—C14—H14 | 119.9 |
| O1—C4—N1i | 126.94 (7) | C15—C14—H14 | 119.9 |
| O1—C4—N1 | 126.94 (7) | C14—C15—C16 | 119.88 (13) |
| N1i—C4—N1 | 106.12 (14) | C14—C15—H15 | 120.1 |
| N1—C5—C11 | 113.16 (9) | C16—C15—H15 | 120.1 |
| N1—C5—H5A | 108.9 | C15—C16—C11 | 120.78 (13) |
| C11—C5—H5A | 108.9 | C15—C16—H16 | 119.6 |
| N1—C5—H5B | 108.9 | C11—C16—H16 | 119.6 |
| C11—C5—H5B | 108.9 |
| Symmetry code: (i) −x+1, y, −z+1/2. |
Experimental details
| Crystal data | |
| Chemical formula | C21H18N2O |
| Mr | 314.37 |
| Crystal system, space group | Monoclinic, C2/c |
| Temperature (K) | 200 |
| a, b, c (Å) | 19.5983 (7), 9.0882 (2), 10.0473 (3) |
| β (°) | 115.593 (4) |
| V (Å3) | 1613.98 (10) |
| Z | 4 |
| Radiation type | Cu Kα |
| µ (mm−1) | 0.63 |
| Crystal size (mm) | 0.37 × 0.21 × 0.15 |
| Data collection | |
| Diffractometer | Agilent SuperNova Dual Cu at zero Atlas |
| Absorption correction | Multi-scan [CrysAlis PRO (Agilent, 2011), using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm (Clark & Reid (1995)] |
| Tmin, Tmax | 0.950, 1.000 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 7837, 1611, 1397 |
| Rint | 0.028 |
| (sin θ/λ)max (Å−1) | 0.621 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.106, 1.07 |
| No. of reflections | 1611 |
| No. of parameters | 111 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.15, −0.16 |
Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Sheldrick, 2008).
References
Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887–897. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gravatt, G. L., Baguley, B. C., Wilson, W. R. & Denny, W. A. (1994). J. Med. Chem. 37, 4338–4345. CrossRef CAS PubMed Web of Science Google Scholar
Horton, D. A., Bourne, G. T. & Smythe, M. L. (2003). Chem. Rev. 103, 893–930. Web of Science CrossRef PubMed CAS Google Scholar
Kim, J. S., Gatto, B., Yu, C., Liu, A., Liu, L. F. & La Voie, E. J. (1996). J. Med. Chem. 39, 992–998. CrossRef CAS PubMed Web of Science Google Scholar
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
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 (Ouzidan et al., 2011a, 2011b), we reported the synthesis of new benzimidazol-2-one derivative by action of benzyl chloride with 1H-benzimidazol-2(3H)-one in the presence of a catalytic quantity of tetra-n-butylammonium bromide under mild conditions to furnish two compounds: mono-substituted (Ouzidan et al., 2011c) and the title compound (Scheme 1).
The title compound C21H18N2O is a new heterocyclic system deriving from benzimidazole. The crystal structure of this molecule is built up from two fused six and five-membered rings linked to two benzyl groups. The oxygen and the adjacent carbon atom are located in the Wyckoff position 4 e on the twofold axis (0, y, 1/4). The fused-ring system is essentially planar, with the maximum deviation of 0.0121 (9) Å for N1 as shown in Fig.1. The benzyl groups are almost perpendicular to the benzimidazole plane but oriented in opposite directions, with a dihedral angle of 81.95 (7). The dihedral angle between the two benzyl rings is abut 60.965 (7)°.