organic compounds
H-benzimidazol-2(3H)-one
of 5-chloro-1,3-bis[2-(2-oxo-1,3-oxazolidin-3-yl)ethyl]-1aLaboratoire de Chimie de la Matière condensée, Faculté des Sciences et Techniques, Université Sidi Mohamed Ben Abdallah, Fès, Morocco, bLaboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Immouzzer, BP 2202, Fès, Morocco, cLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétences Pharmacochimie, Université Mohammed V, BP 1014 Avenue Ibn Batouta, Rabat, Morocco, and dLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
*Correspondence e-mail: k_bouayad@yahoo.fr
In the title compound, C17H19ClN4O5, the benzimidazole fused-ring system is essentially planar, the maximum deviation from the mean plane being 0.06 (1) Å. Both oxazolidine rings are nearly planar, the maximum deviations from the mean planes are 0.071 (13) and 0.070 (10) Å. The dihedral angle between the mean planes of the oxazolidine rings is 69.9 (7)°. The benzimidazole mean plane makes the dihedral angles of 43.9 (6) and 45.6 (6)° with the two oxazolidine rings. In the crystal, the molecules are linked together by weak C—H⋯O hydrogen bonds building zigzag tapes running along the c axis. The Cl atom is split over two positions with an occupancy ratio of 0.567 (7):0.433 (7). This means that the reaction yields two isomers, A and B; the A component has the Cl-atom substituent in the 5-position of the benzimidazolone ring and the B component has the Cl atom in the 6-position. The two isomers form the disordered with a nearly half Cl atom in each of them, as indicated by the occupancy ratio. The was refined as an inversion twin.
CCDC reference: 1421051
1. Related literature
For biological properties of benzimidazol-2-one derivatives, see: Gribkoff et al. (1994); Olesen et al. (1994); Soderlind et al. (1999). For antibacterial activity oxazolidin-2-ones, see: Diekema & Jones (2000); Mukhtar & Wright (2005). For asymmetric reactions of oxazolidin-2-ones, see: Evans et al. (1993); Matsunaga et al. (2005). For oxazolidin-2-one derivatives, see: Ouzidan et al. (2011); Dardouri et al. (2011).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: APEX2 (Bruker, 2009); cell SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus ; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: ORTEP-3 (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).
Supporting information
CCDC reference: 1421051
10.1107/S2056989015016102/xu5863sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989015016102/xu5863Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015016102/xu5863Isup3.cml
To 5-chloro-1H-benzo[d]imidazol-2(3H)-one (0,2 g, 1.18 mmol), potassium carbonate (0.65 g, 4.74 mmol), and tetra-n-butylammonium bromide (0.05 g, 0,1 mmol) in DMF (15 ml) was added bis(2-chloroethyl)amine hydrochloride (0.52 g, 3 mmol). The mixture was heated for 48 h. After the completion of the reaction (as monitored by TLC), the inorganic material salt was filtered and the solvent was removed under reduced pressure. The residue was purified by
on silica gel by using (ethanol/ethylacetate: 1/4) as to furnish colourless crystals.Crystal data, data collection and structure
details are summarized in Table 1. In the molecule there is a pseudo center of symmetry but the results of the structure in the centro symmetric Pbcn are not satisfactory. The cannot be determined reliably and the structure is refined as a 2-component inversion twin.All H atoms could be located in a difference Fourier map. However, they were placed in calculated positions with C—H = 0.93 Å (aromatic), and C—H = 0.97 Å (methylene) and refined as riding on their parent atoms with Uiso(H) = 1.2 Ueq (C).
The chlorine atom is disordered over two positions so that leads to two isomers: 5-chloro-3-methylbenzimidazol-2-one component and a 6-chloro-3-methylbenzimidazol-2-one. The occupancy refined to an 0.567 (7): 0.433 (7) ratio. The C7–C8, C8–C9 and C9–C10 distances were restrained to 1.38 (1) Å.
Data collection: APEX2 (Bruker, 2009); cell
SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: ORTEP-3 (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).C17H19ClN4O5 | Dx = 1.423 Mg m−3 |
Mr = 394.81 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pca21 | Cell parameters from 3701 reflections |
a = 14.053 (8) Å | θ = 1.5–26.4° |
b = 13.438 (6) Å | µ = 0.25 mm−1 |
c = 9.733 (4) Å | T = 296 K |
V = 1838.1 (15) Å3 | Block, colourless |
Z = 4 | 0.35 × 0.31 × 0.26 mm |
F(000) = 820 |
Bruker X8 APEX diffractometer | 3701 independent reflections |
Radiation source: fine-focus sealed tube | 1697 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
φ and ω scans | θmax = 26.4°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −13→17 |
Tmin = 0.504, Tmax = 0.748 | k = −16→16 |
9588 measured reflections | l = −12→12 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.057 | w = 1/[σ2(Fo2) + (0.0473P)2 + 0.3226P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.150 | (Δ/σ)max < 0.001 |
S = 1.01 | Δρmax = 0.21 e Å−3 |
3701 reflections | Δρmin = −0.16 e Å−3 |
255 parameters | Absolute structure: Refined as an inversion twin. |
4 restraints | Absolute structure parameter: 0.5 (5) |
C17H19ClN4O5 | V = 1838.1 (15) Å3 |
Mr = 394.81 | Z = 4 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 14.053 (8) Å | µ = 0.25 mm−1 |
b = 13.438 (6) Å | T = 296 K |
c = 9.733 (4) Å | 0.35 × 0.31 × 0.26 mm |
Bruker X8 APEX diffractometer | 3701 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 1697 reflections with I > 2σ(I) |
Tmin = 0.504, Tmax = 0.748 | Rint = 0.052 |
9588 measured reflections |
R[F2 > 2σ(F2)] = 0.057 | H-atom parameters constrained |
wR(F2) = 0.150 | Δρmax = 0.21 e Å−3 |
S = 1.01 | Δρmin = −0.16 e Å−3 |
3701 reflections | Absolute structure: Refined as an inversion twin. |
255 parameters | Absolute structure parameter: 0.5 (5) |
4 restraints |
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. Refined as a 2-component inversion twin. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.5061 (11) | 0.6238 (11) | 0.3946 (17) | 0.141 (6) | |
H1A | 0.5660 | 0.5943 | 0.3660 | 0.169* | |
H1B | 0.5119 | 0.6955 | 0.3879 | 0.169* | |
C2 | 0.4284 (10) | 0.5885 (9) | 0.3051 (13) | 0.094 (4) | |
H2A | 0.3888 | 0.6431 | 0.2737 | 0.113* | |
H2B | 0.4527 | 0.5523 | 0.2264 | 0.113* | |
C3 | 0.4066 (8) | 0.5371 (8) | 0.5275 (13) | 0.060 (3) | |
C4 | 0.2918 (6) | 0.4698 (6) | 0.3603 (12) | 0.068 (3) | |
H4A | 0.2585 | 0.5066 | 0.2894 | 0.082* | |
H4B | 0.2501 | 0.4650 | 0.4395 | 0.082* | |
C5 | 0.3133 (7) | 0.3677 (7) | 0.3089 (10) | 0.074 (3) | |
H5A | 0.2552 | 0.3394 | 0.2721 | 0.089* | |
H5B | 0.3582 | 0.3733 | 0.2336 | 0.089* | |
C6 | 0.4456 (8) | 0.2814 (7) | 0.4386 (11) | 0.058 (3) | |
C7 | 0.5213 (9) | 0.3189 (9) | 0.3704 (15) | 0.093 (4) | |
H7 | 0.5100 | 0.3570 | 0.2923 | 0.111* | |
C8 | 0.6121 (8) | 0.3041 (8) | 0.4091 (11) | 0.093 (3) | |
H8 | 0.6648 | 0.3351 | 0.3704 | 0.112* | 0.567 (7) |
C9 | 0.6151 (7) | 0.2357 (7) | 0.5151 (15) | 0.085 (4) | |
H9 | 0.6762 | 0.2161 | 0.5395 | 0.102* | 0.433 (7) |
C10 | 0.5401 (8) | 0.1888 (8) | 0.5959 (13) | 0.087 (4) | |
H10 | 0.5521 | 0.1462 | 0.6692 | 0.104* | |
C11 | 0.4446 (10) | 0.2151 (7) | 0.5506 (11) | 0.067 (3) | |
C12 | 0.2912 (5) | 0.2497 (9) | 0.5031 (13) | 0.0513 (14) | |
C13 | 0.3124 (7) | 0.1304 (6) | 0.6914 (9) | 0.071 (3) | |
H13A | 0.2538 | 0.1570 | 0.7293 | 0.085* | |
H13B | 0.3582 | 0.1240 | 0.7654 | 0.085* | |
C14 | 0.2935 (7) | 0.0280 (6) | 0.6264 (11) | 0.067 (3) | |
H14A | 0.2558 | −0.0113 | 0.6898 | 0.080* | |
H14B | 0.2560 | 0.0373 | 0.5437 | 0.080* | |
C15 | 0.4330 (8) | −0.0839 (8) | 0.6883 (11) | 0.068 (3) | |
H15A | 0.3959 | −0.1385 | 0.7256 | 0.081* | |
H15B | 0.4552 | −0.0423 | 0.7632 | 0.081* | |
C16 | 0.5157 (7) | −0.1221 (8) | 0.6022 (10) | 0.075 (3) | |
H16A | 0.5743 | −0.0876 | 0.6247 | 0.090* | |
H16B | 0.5248 | −0.1931 | 0.6146 | 0.090* | |
C17 | 0.4082 (9) | −0.0368 (8) | 0.4637 (11) | 0.066 (3) | |
N1 | 0.3770 (6) | 0.5234 (5) | 0.3986 (8) | 0.052 (2) | |
N2 | 0.3510 (7) | 0.3007 (6) | 0.4064 (9) | 0.064 (2) | |
N3 | 0.3503 (6) | 0.1993 (5) | 0.5834 (8) | 0.0473 (19) | |
N4 | 0.3790 (6) | −0.0276 (6) | 0.5914 (9) | 0.059 (2) | |
O1 | 0.4858 (6) | 0.5965 (7) | 0.5304 (9) | 0.094 (3) | |
O2 | 0.3747 (6) | 0.4989 (7) | 0.6326 (8) | 0.094 (3) | |
O3 | 0.2045 (3) | 0.2489 (6) | 0.4997 (11) | 0.0705 (11) | |
O4 | 0.3742 (6) | −0.0045 (6) | 0.3617 (8) | 0.096 (3) | |
O5 | 0.4846 (6) | −0.0991 (6) | 0.4629 (8) | 0.087 (3) | |
Cl1A | 0.7305 (5) | 0.2867 (5) | 0.4090 (11) | 0.103 (4) | 0.433 (7) |
Cl1B | 0.7313 (5) | 0.2114 (5) | 0.5813 (11) | 0.140 (4) | 0.567 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.139 (13) | 0.160 (14) | 0.123 (13) | −0.094 (11) | 0.019 (12) | 0.004 (12) |
C2 | 0.131 (13) | 0.087 (10) | 0.064 (8) | −0.026 (9) | 0.012 (9) | 0.007 (7) |
C3 | 0.053 (8) | 0.066 (7) | 0.060 (7) | −0.007 (5) | −0.007 (6) | −0.006 (6) |
C4 | 0.067 (9) | 0.056 (7) | 0.082 (8) | −0.004 (5) | −0.033 (6) | 0.012 (6) |
C5 | 0.104 (10) | 0.066 (8) | 0.053 (6) | −0.031 (6) | −0.025 (7) | 0.003 (6) |
C6 | 0.040 (7) | 0.060 (6) | 0.074 (8) | −0.013 (6) | 0.008 (6) | −0.028 (6) |
C7 | 0.070 (8) | 0.105 (9) | 0.103 (8) | −0.019 (7) | 0.012 (7) | −0.040 (7) |
C8 | 0.076 (8) | 0.106 (9) | 0.097 (7) | −0.015 (6) | 0.012 (6) | −0.010 (6) |
C9 | 0.047 (5) | 0.071 (8) | 0.137 (11) | 0.024 (5) | −0.028 (8) | −0.047 (7) |
C10 | 0.099 (10) | 0.077 (7) | 0.084 (7) | 0.048 (8) | −0.036 (7) | −0.051 (6) |
C11 | 0.099 (11) | 0.044 (5) | 0.058 (7) | 0.009 (6) | −0.012 (7) | −0.020 (6) |
C12 | 0.070 (4) | 0.041 (3) | 0.043 (3) | −0.013 (7) | 0.002 (7) | −0.003 (2) |
C13 | 0.120 (11) | 0.045 (6) | 0.047 (5) | 0.003 (6) | 0.021 (6) | 0.008 (5) |
C14 | 0.102 (10) | 0.046 (6) | 0.052 (6) | 0.018 (6) | 0.018 (6) | 0.007 (5) |
C15 | 0.083 (9) | 0.063 (8) | 0.056 (6) | 0.014 (6) | −0.006 (6) | 0.013 (6) |
C16 | 0.089 (8) | 0.082 (7) | 0.055 (6) | 0.023 (6) | −0.013 (6) | −0.007 (6) |
C17 | 0.079 (10) | 0.080 (8) | 0.038 (6) | 0.000 (7) | 0.006 (7) | −0.003 (6) |
N1 | 0.075 (6) | 0.037 (5) | 0.042 (4) | −0.019 (4) | 0.000 (5) | −0.004 (4) |
N2 | 0.090 (7) | 0.048 (5) | 0.055 (5) | −0.005 (5) | 0.005 (6) | −0.007 (4) |
N3 | 0.054 (5) | 0.041 (5) | 0.047 (4) | 0.003 (4) | 0.001 (4) | 0.010 (4) |
N4 | 0.079 (7) | 0.059 (6) | 0.040 (4) | 0.004 (5) | 0.015 (5) | 0.013 (4) |
O1 | 0.096 (7) | 0.120 (7) | 0.064 (5) | −0.036 (6) | −0.001 (5) | −0.019 (5) |
O2 | 0.097 (7) | 0.135 (7) | 0.051 (5) | −0.013 (5) | 0.005 (4) | 0.012 (5) |
O3 | 0.055 (3) | 0.068 (2) | 0.090 (3) | −0.008 (5) | 0.002 (7) | −0.0005 (19) |
O4 | 0.098 (7) | 0.151 (8) | 0.038 (4) | 0.031 (5) | 0.003 (4) | 0.019 (5) |
O5 | 0.082 (6) | 0.113 (7) | 0.066 (5) | 0.037 (5) | 0.015 (5) | −0.008 (5) |
Cl1A | 0.067 (6) | 0.075 (5) | 0.166 (8) | −0.006 (4) | 0.006 (5) | 0.010 (5) |
Cl1B | 0.071 (5) | 0.123 (5) | 0.226 (9) | 0.038 (4) | −0.040 (5) | 0.020 (6) |
C1—O1 | 1.401 (15) | C9—Cl1A | 2.042 (15) |
C1—C2 | 1.475 (17) | C9—H9 | 0.9300 |
C1—H1A | 0.9700 | C10—C11 | 1.456 (15) |
C1—H1B | 0.9700 | C10—H10 | 0.9300 |
C2—N1 | 1.454 (13) | C11—N3 | 1.379 (14) |
C2—H2A | 0.9700 | C12—O3 | 1.219 (6) |
C2—H2B | 0.9700 | C12—N3 | 1.326 (12) |
C3—O2 | 1.230 (14) | C12—N2 | 1.436 (13) |
C3—N1 | 1.334 (14) | C13—N3 | 1.499 (11) |
C3—O1 | 1.369 (12) | C13—C14 | 1.538 (12) |
C4—N1 | 1.447 (11) | C13—H13A | 0.9700 |
C4—C5 | 1.491 (12) | C13—H13B | 0.9700 |
C4—H4A | 0.9700 | C14—N4 | 1.455 (11) |
C4—H4B | 0.9700 | C14—H14A | 0.9700 |
C5—N2 | 1.411 (12) | C14—H14B | 0.9700 |
C5—H5A | 0.9700 | C15—N4 | 1.428 (12) |
C5—H5B | 0.9700 | C15—C16 | 1.522 (13) |
C6—C7 | 1.352 (16) | C15—H15A | 0.9700 |
C6—N2 | 1.391 (13) | C15—H15B | 0.9700 |
C6—C11 | 1.408 (8) | C16—O5 | 1.458 (11) |
C7—C8 | 1.345 (10) | C16—H16A | 0.9700 |
C7—H7 | 0.9300 | C16—H16B | 0.9700 |
C8—C9 | 1.383 (11) | C17—O4 | 1.183 (14) |
C8—Cl1A | 1.680 (13) | C17—N4 | 1.315 (14) |
C8—H8 | 0.9300 | C17—O5 | 1.362 (13) |
C9—C10 | 1.458 (10) | Cl1A—Cl1B | 1.959 (6) |
C9—Cl1B | 1.786 (10) | ||
O1—C1—C2 | 108.8 (11) | N3—C11—C6 | 106.6 (12) |
O1—C1—H1A | 109.9 | N3—C11—C10 | 141.1 (11) |
C2—C1—H1A | 109.9 | C6—C11—C10 | 112.2 (14) |
O1—C1—H1B | 109.9 | O3—C12—N3 | 129.7 (12) |
C2—C1—H1B | 109.9 | O3—C12—N2 | 124.8 (12) |
H1A—C1—H1B | 108.3 | N3—C12—N2 | 105.3 (5) |
N1—C2—C1 | 101.1 (10) | N3—C13—C14 | 109.0 (7) |
N1—C2—H2A | 111.6 | N3—C13—H13A | 109.9 |
C1—C2—H2A | 111.6 | C14—C13—H13A | 109.9 |
N1—C2—H2B | 111.6 | N3—C13—H13B | 109.9 |
C1—C2—H2B | 111.6 | C14—C13—H13B | 109.9 |
H2A—C2—H2B | 109.4 | H13A—C13—H13B | 108.3 |
O2—C3—N1 | 127.6 (10) | N4—C14—C13 | 114.4 (8) |
O2—C3—O1 | 121.5 (11) | N4—C14—H14A | 108.7 |
N1—C3—O1 | 110.7 (11) | C13—C14—H14A | 108.7 |
N1—C4—C5 | 112.2 (8) | N4—C14—H14B | 108.7 |
N1—C4—H4A | 109.2 | C13—C14—H14B | 108.7 |
C5—C4—H4A | 109.2 | H14A—C14—H14B | 107.6 |
N1—C4—H4B | 109.2 | N4—C15—C16 | 102.8 (8) |
C5—C4—H4B | 109.2 | N4—C15—H15A | 111.2 |
H4A—C4—H4B | 107.9 | C16—C15—H15A | 111.2 |
N2—C5—C4 | 115.9 (8) | N4—C15—H15B | 111.2 |
N2—C5—H5A | 108.3 | C16—C15—H15B | 111.2 |
C4—C5—H5A | 108.3 | H15A—C15—H15B | 109.1 |
N2—C5—H5B | 108.3 | O5—C16—C15 | 102.2 (8) |
C4—C5—H5B | 108.3 | O5—C16—H16A | 111.3 |
H5A—C5—H5B | 107.4 | C15—C16—H16A | 111.3 |
C7—C6—N2 | 124.9 (12) | O5—C16—H16B | 111.3 |
C7—C6—C11 | 128.7 (15) | C15—C16—H16B | 111.3 |
N2—C6—C11 | 106.4 (12) | H16A—C16—H16B | 109.2 |
C8—C7—C6 | 123.6 (14) | O4—C17—N4 | 129.3 (12) |
C8—C7—H7 | 118.2 | O4—C17—O5 | 122.5 (11) |
C6—C7—H7 | 118.2 | N4—C17—O5 | 108.0 (10) |
C7—C8—C9 | 109.6 (11) | C3—N1—C4 | 124.7 (9) |
C7—C8—Cl1A | 163.7 (10) | C3—N1—C2 | 110.5 (9) |
C9—C8—Cl1A | 83.0 (9) | C4—N1—C2 | 123.4 (9) |
C7—C8—H8 | 125.2 | C6—N2—C5 | 129.0 (10) |
C9—C8—H8 | 125.2 | C6—N2—C12 | 108.8 (9) |
Cl1A—C8—H8 | 43.4 | C5—N2—C12 | 121.7 (10) |
C8—C9—C10 | 131.9 (10) | C12—N3—C11 | 112.8 (8) |
C8—C9—Cl1B | 114.8 (10) | C12—N3—C13 | 120.4 (9) |
C10—C9—Cl1B | 112.8 (9) | C11—N3—C13 | 126.7 (9) |
C8—C9—Cl1A | 54.8 (8) | C17—N4—C15 | 114.1 (10) |
C10—C9—Cl1A | 172.8 (7) | C17—N4—C14 | 121.8 (10) |
Cl1B—C9—Cl1A | 61.2 (4) | C15—N4—C14 | 123.8 (8) |
C8—C9—H9 | 114.0 | C3—O1—C1 | 107.4 (10) |
C10—C9—H9 | 114.0 | C17—O5—C16 | 111.2 (8) |
Cl1B—C9—H9 | 8.4 | C8—Cl1A—Cl1B | 94.4 (5) |
Cl1A—C9—H9 | 59.3 | C8—Cl1A—C9 | 42.2 (4) |
C11—C10—C9 | 113.4 (10) | Cl1B—Cl1A—C9 | 53.0 (4) |
C11—C10—H10 | 123.3 | C9—Cl1B—Cl1A | 65.9 (6) |
C9—C10—H10 | 123.3 |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···O2i | 0.97 | 2.42 | 3.247 (13) | 143 |
C14—H14A···O4ii | 0.97 | 2.48 | 3.315 (13) | 144 |
Symmetry codes: (i) −x+1/2, y, z−1/2; (ii) −x+1/2, y, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···O2i | 0.97 | 2.42 | 3.247 (13) | 143.3 |
C14—H14A···O4ii | 0.97 | 2.48 | 3.315 (13) | 144.3 |
Symmetry codes: (i) −x+1/2, y, z−1/2; (ii) −x+1/2, y, z+1/2. |
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Benzimidazol-2-one derivatives are useful heterocyclic building blocks and are prominent structural elements of compounds demonstrating a wide variety of pharmacological and biochemical properties(Gribkoff et al., 1994; Olesen et al., 1994; Soderlind et al., 1999).
Also, oxazolidin-2-ones are a very important class of heterocyclic compounds and their derivatives have attracted attention in various areas of drug development for antibacterial activity (Diekema & Jones, 2000; Mukhtar & Wright, 2005). Some oxazolidin-2-ones have been used as chiral auxiliaries in a wide range of asymmetric reactions (Evans et al., 1993; Matsunaga et al., 2005). In a previous study, we reacted 1H-benzo[d]imidazol-2(3H)-one with bis(2-chloroethyl)amine hydrochloride in the presence of a catalytic quantity of tetra-n-butylammonium bromide to form 1,3-bis(2-(2-oxooxazolidin-3-yl)ethyl)-1H-benzo[d]imidazol-2(3H)-one (Ouzidan et al., 2011). The study is extended to the synthesis of the 5-chloro analog to furnish the title compound (Scheme 1).
The molecule of title compound is build up from a fused five- and six-membered rings linked through ethyl groups, on opposite side, to two 2-oxo-oxazolidin- 3-yl rings as shown in Fig. 1. The chlorine in 5-chloro-benzo[d]imidazol-2(3H) -one is splited in two positions with an occupancy ratio of Cl1B = 0.567 (7) and Cl1A = 0.433 (7). As a matter of fact, we have two isomers that form a disordered co-crystal, like in the 5-Chloro-1-[(E)-3-(dimethylamino)acryloyl]- 3-methyl-1H-benzimidazol-2(3H)-one-6-chloro-1-[(E)-3-(dimethylamino)acryloyl]- 3-methyl-1H-benzimidazol-2(3H)-one(4/1) (Dardouri et al., 2011), but with a nearly half chlorine atom in each of them as shown in the occupancy ratio of Cl1A and Cl1B. The fused rings system (N2N3C6 – C12) is essentially planar with the largest deviation from the mean plane being 0.06 (1) Å at C8 atom. The benzimidazole plane makes dihedral angles of 43.9 (6)° and 45.6 (6)° with the two 2-oxo-oxazolidin-3-yl rings, (O1N1C1-C3) and (O5N4C15-C17), respectively. The dihedral angle between the two 2-oxo-oxazolidin-3-yl rings is of 69.9 (7)°. In the crystal, the molecules are linked together by C4–H4A···O2 and C14–H14A···O4 hydrogen bonds in the way to build a zigzag tape along c axis as shown in Fig. 2 and Table 2.