organic compounds
1-(4-Methylbenzyl)-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, 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
In the title compound, C15H14N2O, the fused five- and six-membered ring system is essentially planar, the maximum deviation from the mean plane being 0.009 (1) Å. The benzimidazol-2(3H)-one residue is nearly perpendicular to the benzyl ring, forming a dihedral angle of 77.41 (6)°. In the crystal, inversion dimers are formed by pairs of N—H⋯O hydrogen bonds; these dimers are linked by weak C—H⋯O interactions into a two-dimensional array in the (102) plane.
Related literature
For pharmacological and biochemical properties of benzimidazole derivatives, see: Lee et al. (2004); Deligeorgiev et al. (2011); Scott et al. (2002); Gothelf et al. (1998). For related structures, see: Belaziz et al. (2012); Ouzidan et al. (2011).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); 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
https://doi.org/10.1107/S1600536812050726/tk5182sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812050726/tk5182Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812050726/tk5182Isup3.cml
To 1H-benzimidazol-2(3H)-one (0.2 g, 1.49 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 methyl benzyl bromide (0.33 g, 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
on a column of silica gel with ethyl acetate/hexane (1/2) as The compound was recrystallized from hexane to give colorless crystals.H atoms were located in a difference map and treated as riding with N—H = 0.94 Å, C—H = 0.93 Å (aromatic), C—H = 0.97 Å (methylene) and C—H = 0.96 Å (methyl), and with Uiso(H) = 1.2 Ueq (N, aromatic-C, methylene-C) and Uiso(H) = 1.5 Ueq(methyl-C). Two reflections, i.e. (-1 0 1) and (1 0 1), were omitted owing to poor agreement.
The development of benzimidazole derivatives has experienced in recent years, a considerable expansion following reports of biological activities presented by this type of compound. Benzimidazole derivatives are endowed with anti-viral, anti-ulcer, anti-hypertensive and anti-cancer activities (Lee et al., 2004; Deligeorgiev et al., 2011; Scott et al., 2002). Heterocycles containing the benzimidazole nucleus are also antagonists of a number of biological receptors, namely angiotensin II and prostaglandin D2 (Gothelf et al., 1998).
In a previous study, we reacted benzimidazol-2-one with dodecyl bromide in the presence of a catalytic quantity of tetra-n-butylammonium bromide under mild conditions to form 1-dodecyl-1H-benzimidazol-2(3H)-one (Belaziz et al., 2012; Ouzidan et al., 2011). The study is extended to the synthesis of new benzimidazol-2-one derivative by action of methylbenzyl bromide with 1H-benzimidazol-2(3H)-one to form the title compound (Scheme 1).
The
of the title compound, C15H14N2O, is built up from two fused five- and six-membered rings (C1-C7,N1,N2,O1) linked to (C8-C15) the p-methyl-benzyl residue as shown in Fig. 1. The fused-ring system is essentially planar, with the maximum deviation of 0.009 (1) Å for the N2 atom. The dihedral angle between the benzimidazol-2(3H-one system and the (C9 to C14) benzyl ring is 77.41 (6)°.In the crystal, inversion dimers are linked by N1—H1N···O1 hydrogen bonds. These are linked by weak C8–H8A···O1 and C15–H15C···O1 non-classic hydrogen bonds to form a layer parallel to (1 0 2); see Fig. 2 and Table 1.
For pharmacological and biochemical properties of benzimidazole derivatives, see: Lee et al. (2004); Deligeorgiev et al. (2011); Scott et al. (2002); Gothelf et al. (1998). For related structures, see: Belaziz et al. (2012); Ouzidan et al. (2011).
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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).C15H14N2O | F(000) = 504 |
Mr = 238.28 | Dx = 1.271 Mg m−3 |
Monoclinic, P21/n | Melting point: 456 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 12.5585 (5) Å | Cell parameters from 3211 reflections |
b = 5.7181 (2) Å | θ = 3.3–28.7° |
c = 17.4153 (7) Å | µ = 0.08 mm−1 |
β = 95.277 (2)° | T = 296 K |
V = 1245.31 (8) Å3 | Block, colourless |
Z = 4 | 0.51 × 0.42 × 0.15 mm |
Bruker X8 APEXII diffractometer | 2157 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.029 |
Graphite monochromator | θmax = 28.7°, θmin = 3.3° |
φ and ω scans | h = −16→10 |
16486 measured reflections | k = −7→7 |
3211 independent reflections | l = −23→23 |
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)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.122 | w = 1/[σ2(Fo2) + (0.0511P)2 + 0.2271P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
3211 reflections | Δρmax = 0.17 e Å−3 |
164 parameters | Δρmin = −0.15 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: 0.0047 (19) |
C15H14N2O | V = 1245.31 (8) Å3 |
Mr = 238.28 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.5585 (5) Å | µ = 0.08 mm−1 |
b = 5.7181 (2) Å | T = 296 K |
c = 17.4153 (7) Å | 0.51 × 0.42 × 0.15 mm |
β = 95.277 (2)° |
Bruker X8 APEXII diffractometer | 2157 reflections with I > 2σ(I) |
16486 measured reflections | Rint = 0.029 |
3211 independent reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.17 e Å−3 |
3211 reflections | Δρmin = −0.15 e Å−3 |
164 parameters |
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 | 0.40817 (8) | 0.80403 (18) | 0.04185 (6) | 0.0541 (3) | |
N1 | 0.59419 (10) | 0.8138 (2) | 0.06169 (7) | 0.0456 (3) | |
H1N1 | 0.6036 | 0.9478 | 0.0317 | 0.055* | |
C6 | 0.67241 (12) | 0.6686 (2) | 0.09809 (7) | 0.0416 (3) | |
N2 | 0.50984 (9) | 0.51864 (19) | 0.10975 (6) | 0.0425 (3) | |
C9 | 0.41188 (10) | 0.3448 (2) | 0.21353 (8) | 0.0399 (3) | |
C5 | 0.61861 (11) | 0.4813 (2) | 0.12841 (7) | 0.0405 (3) | |
C8 | 0.42295 (12) | 0.3671 (2) | 0.12812 (8) | 0.0475 (4) | |
H8A | 0.4343 | 0.2127 | 0.1073 | 0.057* | |
H8B | 0.3565 | 0.4273 | 0.1029 | 0.057* | |
C4 | 0.67330 (13) | 0.3032 (3) | 0.16849 (8) | 0.0498 (4) | |
H4 | 0.6375 | 0.1783 | 0.1886 | 0.060* | |
C14 | 0.44588 (12) | 0.5170 (2) | 0.26587 (8) | 0.0498 (4) | |
H14 | 0.4778 | 0.6517 | 0.2487 | 0.060* | |
C10 | 0.36386 (12) | 0.1473 (3) | 0.24098 (9) | 0.0500 (4) | |
H10 | 0.3403 | 0.0291 | 0.2069 | 0.060* | |
C7 | 0.49498 (12) | 0.7221 (2) | 0.06784 (8) | 0.0425 (3) | |
C1 | 0.78212 (12) | 0.6843 (3) | 0.10756 (9) | 0.0518 (4) | |
H1 | 0.8181 | 0.8099 | 0.0879 | 0.062* | |
C3 | 0.78367 (13) | 0.3187 (3) | 0.17738 (9) | 0.0568 (4) | |
H3 | 0.8228 | 0.2012 | 0.2039 | 0.068* | |
C12 | 0.38486 (12) | 0.2947 (3) | 0.37129 (9) | 0.0568 (4) | |
C2 | 0.83703 (13) | 0.5043 (3) | 0.14782 (9) | 0.0581 (4) | |
H2 | 0.9113 | 0.5093 | 0.1550 | 0.070* | |
C11 | 0.35059 (12) | 0.1242 (3) | 0.31856 (9) | 0.0582 (4) | |
H11 | 0.3178 | −0.0095 | 0.3356 | 0.070* | |
C13 | 0.43294 (13) | 0.4911 (3) | 0.34360 (9) | 0.0580 (4) | |
H13 | 0.4571 | 0.6084 | 0.3779 | 0.070* | |
C15 | 0.37084 (17) | 0.2654 (5) | 0.45607 (11) | 0.0944 (7) | |
H15A | 0.3991 | 0.4000 | 0.4839 | 0.142* | |
H15B | 0.4084 | 0.1281 | 0.4753 | 0.142* | |
H15C | 0.2962 | 0.2495 | 0.4628 | 0.142* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0523 (7) | 0.0521 (6) | 0.0563 (6) | 0.0055 (5) | −0.0040 (5) | 0.0144 (5) |
N1 | 0.0529 (8) | 0.0409 (6) | 0.0424 (7) | 0.0004 (5) | 0.0018 (5) | 0.0097 (5) |
C6 | 0.0511 (9) | 0.0410 (7) | 0.0326 (7) | 0.0025 (6) | 0.0027 (6) | −0.0010 (5) |
N2 | 0.0466 (7) | 0.0404 (6) | 0.0399 (6) | 0.0001 (5) | 0.0003 (5) | 0.0076 (5) |
C9 | 0.0376 (8) | 0.0381 (7) | 0.0431 (8) | 0.0002 (5) | −0.0018 (6) | 0.0029 (5) |
C5 | 0.0484 (9) | 0.0403 (7) | 0.0323 (7) | 0.0019 (6) | 0.0006 (6) | −0.0010 (5) |
C8 | 0.0535 (9) | 0.0437 (7) | 0.0440 (8) | −0.0072 (6) | −0.0024 (7) | 0.0014 (6) |
C4 | 0.0621 (10) | 0.0427 (8) | 0.0432 (8) | 0.0042 (6) | −0.0029 (7) | 0.0051 (6) |
C14 | 0.0565 (10) | 0.0425 (8) | 0.0497 (9) | −0.0090 (6) | 0.0009 (7) | −0.0003 (6) |
C10 | 0.0496 (9) | 0.0448 (8) | 0.0542 (9) | −0.0094 (6) | −0.0019 (7) | 0.0020 (6) |
C7 | 0.0520 (9) | 0.0398 (7) | 0.0348 (7) | 0.0029 (6) | 0.0000 (6) | 0.0033 (5) |
C1 | 0.0519 (10) | 0.0568 (9) | 0.0471 (9) | −0.0046 (7) | 0.0063 (7) | −0.0004 (6) |
C3 | 0.0599 (11) | 0.0558 (9) | 0.0526 (9) | 0.0145 (7) | −0.0063 (8) | 0.0023 (7) |
C12 | 0.0410 (9) | 0.0808 (12) | 0.0485 (9) | 0.0004 (8) | 0.0044 (7) | 0.0068 (8) |
C2 | 0.0490 (10) | 0.0715 (11) | 0.0529 (9) | 0.0090 (8) | 0.0000 (7) | −0.0049 (8) |
C11 | 0.0481 (10) | 0.0646 (10) | 0.0619 (11) | −0.0107 (7) | 0.0054 (8) | 0.0173 (8) |
C13 | 0.0599 (11) | 0.0654 (10) | 0.0478 (9) | −0.0044 (8) | −0.0003 (7) | −0.0104 (7) |
C15 | 0.0829 (15) | 0.148 (2) | 0.0539 (12) | −0.0091 (14) | 0.0142 (10) | 0.0111 (12) |
O1—C7 | 1.2338 (16) | C14—C13 | 1.386 (2) |
N1—C7 | 1.3649 (18) | C14—H14 | 0.9300 |
N1—C6 | 1.3933 (17) | C10—C11 | 1.383 (2) |
N1—H1N1 | 0.9411 | C10—H10 | 0.9300 |
C6—C1 | 1.375 (2) | C1—C2 | 1.392 (2) |
C6—C5 | 1.3959 (19) | C1—H1 | 0.9300 |
N2—C7 | 1.3770 (16) | C3—C2 | 1.380 (2) |
N2—C5 | 1.3913 (17) | C3—H3 | 0.9300 |
N2—C8 | 1.4521 (17) | C12—C11 | 1.381 (2) |
C9—C14 | 1.3822 (19) | C12—C13 | 1.383 (2) |
C9—C10 | 1.3857 (19) | C12—C15 | 1.512 (2) |
C9—C8 | 1.5120 (19) | C2—H2 | 0.9300 |
C5—C4 | 1.3811 (18) | C11—H11 | 0.9300 |
C8—H8A | 0.9700 | C13—H13 | 0.9300 |
C8—H8B | 0.9700 | C15—H15A | 0.9600 |
C4—C3 | 1.383 (2) | C15—H15B | 0.9600 |
C4—H4 | 0.9300 | C15—H15C | 0.9600 |
C7—N1—C6 | 110.24 (11) | C9—C10—H10 | 119.7 |
C7—N1—H1N1 | 121.3 | O1—C7—N1 | 127.42 (13) |
C6—N1—H1N1 | 128.2 | O1—C7—N2 | 125.97 (13) |
C1—C6—N1 | 132.24 (13) | N1—C7—N2 | 106.61 (12) |
C1—C6—C5 | 121.27 (13) | C6—C1—C2 | 117.16 (14) |
N1—C6—C5 | 106.49 (12) | C6—C1—H1 | 121.4 |
C7—N2—C5 | 109.63 (11) | C2—C1—H1 | 121.4 |
C7—N2—C8 | 123.58 (12) | C2—C3—C4 | 121.57 (14) |
C5—N2—C8 | 126.76 (11) | C2—C3—H3 | 119.2 |
C14—C9—C10 | 118.08 (13) | C4—C3—H3 | 119.2 |
C14—C9—C8 | 122.55 (12) | C11—C12—C13 | 117.44 (15) |
C10—C9—C8 | 119.36 (12) | C11—C12—C15 | 120.94 (18) |
C4—C5—N2 | 131.55 (13) | C13—C12—C15 | 121.61 (17) |
C4—C5—C6 | 121.43 (14) | C3—C2—C1 | 121.44 (15) |
N2—C5—C6 | 107.02 (11) | C3—C2—H2 | 119.3 |
N2—C8—C9 | 113.95 (11) | C1—C2—H2 | 119.3 |
N2—C8—H8A | 108.8 | C12—C11—C10 | 121.61 (15) |
C9—C8—H8A | 108.8 | C12—C11—H11 | 119.2 |
N2—C8—H8B | 108.8 | C10—C11—H11 | 119.2 |
C9—C8—H8B | 108.8 | C12—C13—C14 | 121.43 (15) |
H8A—C8—H8B | 107.7 | C12—C13—H13 | 119.3 |
C5—C4—C3 | 117.12 (14) | C14—C13—H13 | 119.3 |
C5—C4—H4 | 121.4 | C12—C15—H15A | 109.5 |
C3—C4—H4 | 121.4 | C12—C15—H15B | 109.5 |
C9—C14—C13 | 120.74 (14) | H15A—C15—H15B | 109.5 |
C9—C14—H14 | 119.6 | C12—C15—H15C | 109.5 |
C13—C14—H14 | 119.6 | H15A—C15—H15C | 109.5 |
C11—C10—C9 | 120.69 (14) | H15B—C15—H15C | 109.5 |
C11—C10—H10 | 119.7 | ||
C7—N1—C6—C1 | −179.97 (14) | C8—C9—C10—C11 | −178.65 (14) |
C7—N1—C6—C5 | −0.56 (15) | C6—N1—C7—O1 | −179.46 (13) |
C7—N2—C5—C4 | −179.25 (14) | C6—N1—C7—N2 | 1.05 (15) |
C8—N2—C5—C4 | −1.2 (2) | C5—N2—C7—O1 | 179.35 (13) |
C7—N2—C5—C6 | 0.82 (14) | C8—N2—C7—O1 | 1.3 (2) |
C8—N2—C5—C6 | 178.83 (12) | C5—N2—C7—N1 | −1.15 (15) |
C1—C6—C5—C4 | −0.6 (2) | C8—N2—C7—N1 | −179.24 (12) |
N1—C6—C5—C4 | 179.90 (12) | N1—C6—C1—C2 | −179.93 (14) |
C1—C6—C5—N2 | 179.33 (12) | C5—C6—C1—C2 | 0.7 (2) |
N1—C6—C5—N2 | −0.16 (14) | C5—C4—C3—C2 | 0.3 (2) |
C7—N2—C8—C9 | −117.18 (14) | C4—C3—C2—C1 | −0.1 (2) |
C5—N2—C8—C9 | 65.08 (17) | C6—C1—C2—C3 | −0.4 (2) |
C14—C9—C8—N2 | 26.23 (19) | C13—C12—C11—C10 | 0.2 (2) |
C10—C9—C8—N2 | −155.20 (13) | C15—C12—C11—C10 | −179.31 (17) |
N2—C5—C4—C3 | −179.82 (14) | C9—C10—C11—C12 | −0.4 (2) |
C6—C5—C4—C3 | 0.1 (2) | C11—C12—C13—C14 | 0.3 (2) |
C10—C9—C14—C13 | 0.5 (2) | C15—C12—C13—C14 | 179.84 (16) |
C8—C9—C14—C13 | 179.13 (14) | C9—C14—C13—C12 | −0.7 (2) |
C14—C9—C10—C11 | 0.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N1···O1i | 0.94 | 1.91 | 2.8317 (15) | 166 |
C15—H15C···O1ii | 0.96 | 2.58 | 3.514 (2) | 165 |
C8—H8A···O1iii | 0.97 | 2.61 | 3.5504 (18) | 164 |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+1/2, y−1/2, −z+1/2; (iii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C15H14N2O |
Mr | 238.28 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 296 |
a, b, c (Å) | 12.5585 (5), 5.7181 (2), 17.4153 (7) |
β (°) | 95.277 (2) |
V (Å3) | 1245.31 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.51 × 0.42 × 0.15 |
Data collection | |
Diffractometer | Bruker X8 APEXII |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16486, 3211, 2157 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.676 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.122, 1.02 |
No. of reflections | 3211 |
No. of parameters | 164 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.15 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2009) and publCIF (Westrip,2010).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N1···O1i | 0.94 | 1.91 | 2.8317 (15) | 166 |
C15—H15C···O1ii | 0.96 | 2.58 | 3.514 (2) | 165 |
C8—H8A···O1iii | 0.97 | 2.61 | 3.5504 (18) | 164 |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+1/2, y−1/2, −z+1/2; (iii) x, y−1, z. |
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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The development of benzimidazole derivatives has experienced in recent years, a considerable expansion following reports of biological activities presented by this type of compound. Benzimidazole derivatives are endowed with anti-viral, anti-ulcer, anti-hypertensive and anti-cancer activities (Lee et al., 2004; Deligeorgiev et al., 2011; Scott et al., 2002). Heterocycles containing the benzimidazole nucleus are also antagonists of a number of biological receptors, namely angiotensin II and prostaglandin D2 (Gothelf et al., 1998).
In a previous study, we reacted benzimidazol-2-one with dodecyl bromide in the presence of a catalytic quantity of tetra-n-butylammonium bromide under mild conditions to form 1-dodecyl-1H-benzimidazol-2(3H)-one (Belaziz et al., 2012; Ouzidan et al., 2011). The study is extended to the synthesis of new benzimidazol-2-one derivative by action of methylbenzyl bromide with 1H-benzimidazol-2(3H)-one to form the title compound (Scheme 1).
The crystal structure of the title compound, C15H14N2O, is built up from two fused five- and six-membered rings (C1-C7,N1,N2,O1) linked to (C8-C15) the p-methyl-benzyl residue as shown in Fig. 1. The fused-ring system is essentially planar, with the maximum deviation of 0.009 (1) Å for the N2 atom. The dihedral angle between the benzimidazol-2(3H-one system and the (C9 to C14) benzyl ring is 77.41 (6)°.
In the crystal, inversion dimers are linked by N1—H1N···O1 hydrogen bonds. These are linked by weak C8–H8A···O1 and C15–H15C···O1 non-classic hydrogen bonds to form a layer parallel to (1 0 2); see Fig. 2 and Table 1.