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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 Jan 12;67(Pt 2):o362–o363. doi: 10.1107/S1600536810052141

1,3-Bis[2-(2-oxo-1,3-oxazolidin-3-yl)eth­yl]-1H-benzimidazol-2(3H)-one

Younes Ouzidan a, Youssef Kandri Rodi a, Frank R Fronczek b, Ramaiyer Venkatraman c, Lahcen El Ammari d, El Mokhtar Essassi e,*
PMCID: PMC3051530  PMID: 21523041

Abstract

The mol­ecular structure of the title compound, C17H20N4O5, contains a central fused-ring system, comprised of six- and five-membered rings. This unit is linked by C2 chains to two 2-oxo-1,3-oxazolidine five-membered rings. The central fused-ring system is essentially planar, with a maximum deviation of 0.008 (1) Å from the mean plane. Both oxazolidine five-membered rings are also nearly planar, with maximum deviations of 0.090 (1) and 0.141 (1) Å.

Related literature

For the pharmacological and biochemical properties of oxazolidin-2-ones, see: Gribkoff et al. (1994 ▶); Olesen et al. (1994 ▶); Soderlind et al. (1999 ▶). For their anti­bacterial activity, see: Diekema & Jones (2000 ▶); Mukhtar & Wright (2005 ▶). For related structures, see: Ouzidan et al. (2010 ▶); Matsunaga et al. (2005 ▶); Evans et al. (1993 ▶); Caleb et al. (2009 ▶); Ahoya et al. (2010 ▶); Bel-Ghacham et al. (2010 ▶); Alsubari et al. (2009 ▶).graphic file with name e-67-0o362-scheme1.jpg

Experimental

Crystal data

  • C17H20N4O5

  • M r = 360.37

  • Monoclinic, Inline graphic

  • a = 10.5331 (10) Å

  • b = 10.9647 (10) Å

  • c = 14.5541 (14) Å

  • β = 103.258 (5)°

  • V = 1636.1 (3) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 0.92 mm−1

  • T = 90 K

  • 0.30 × 0.28 × 0.18 mm

Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.770, T max = 0.852

  • 15549 measured reflections

  • 2914 independent reflections

  • 2842 reflections with I > 2σ(I)

  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.030

  • wR(F 2) = 0.074

  • S = 1.05

  • 2914 reflections

  • 235 parameters

  • H-atom parameters constrained

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.19 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: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810052141/fj2373sup1.cif

e-67-0o362-sup1.cif (18.5KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052141/fj2373Isup2.hkl

e-67-0o362-Isup2.hkl (143.1KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

Benzimidazol-2-one derivatives are useful heterocyclic building blocks and are prominent structural elements of compounds presenting 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 the previous works, we have studied the crystal structure of several heterocyclic systems containng oxazolidin-2-one (Ouzidan et al. (2010); Caleb et al. (2009); Ahoya et al. (2010); Bel-Ghacham et al. (2010); Alsubari et al. (2009)). In this work, we have synthesized benzimidazol-2-one possessing Oxazolidin-2-one ring by action of bis(2-chloroethyl)amine hydrochloride with 1H-benzo[d]imidazol-2(3H)-one using same conditions, the reaction provided the title compound (Scheme 1).

The 1,3-bis(2-(2-oxo-oxazolidin-3-yl)ethyl)-1H-benzimidazol -\2(3H)-one molecule structure is built up from two fused six-and five-membered rings linked to two chains of five-membered rings by ethylene groups as schown in Fg.1. The fused-ring system is essentially planar, with a maximum deviation of 0.008 (1) Å and -0.008 (1) Å for C1 and C7 or N2 respectyvely. The dihedral angle between them does not exceed 0.23 (6)°. The both five-membered rings (2-oxo-oxazolidine) are almost planar with maximum deviation of -0.090 (1) Å and -0.141 (1) Å for C11 and C16 respectyvely. Their puckering parameters are Q2 = 0.1498 (2) Å and φ2 = 131.6 (5)° for (O2C10N3C12C11) and Q2 = 0.2343 (2) Å and φ2 = -49.4 (3)° for (O4C15N4C17C16). The dihedral angles between each of them and the fused rings are 43.02 (5)° (O2C10N3C12C11) and 49.12 (6)° (O4C15N4C17C16). The torsion angles C1 N1 C8 C9 and C1 N2 C13 C14 are -87.85 (2)° and 101.00 (2)° respectively. These values show the strong asymmetry of the molecule.

Experimental

To 1H-benzo[d]imidazol-2(3H)-one (0,2 g, 1,5 mmol), potassium carbonate (0,82 g, 6 mmol), and tetra-n-butylammonium bromide (0.1 g, 0,3 mmol) in DMF (15 ml) was added bis(2-chloroethyl)amine hydrochloride (0,64 g, 3,58 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 column chromatography on silica gel by using (ethanol/ethyl acetate: 1/4) as eluent. Colorless crystals were isolated when the solvent was allowed to evaporate.

Refinement

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 Ueq(aromatic, methine).

Figures

Fig. 1.

Fig. 1.

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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.

Crystal data

C17H20N4O5 F(000) = 760
Mr = 360.37 Dx = 1.463 Mg m−3
Monoclinic, P21/c Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc Cell parameters from 9916 reflections
a = 10.5331 (10) Å θ = 4.0–68.1°
b = 10.9647 (10) Å µ = 0.92 mm−1
c = 14.5541 (14) Å T = 90 K
β = 103.258 (5)° Fragment, colourless
V = 1636.1 (3) Å3 0.30 × 0.28 × 0.18 mm
Z = 4
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Data collection

Bruker APEXII CCD diffractometer 2914 independent reflections
Radiation source: fine-focus sealed tube 2842 reflections with I > 2σ(I)
graphite Rint = 0.024
φ and ω scans θmax = 68.2°, θmin = 4.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005) h = −12→9
Tmin = 0.770, Tmax = 0.852 k = −12→13
15549 measured reflections l = −17→17
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Refinement

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)] = 0.030 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074 H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0315P)2 + 0.8105P] where P = (Fo2 + 2Fc2)/3
2914 reflections (Δ/σ)max < 0.001
235 parameters Δρmax = 0.23 e Å−3
0 restraints Δρmin = −0.19 e Å−3
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Special details

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

x y z Uiso*/Ueq
O1 0.51156 (8) 0.90454 (8) 0.65034 (6) 0.01864 (19)
O2 0.81349 (8) 0.63845 (8) 0.39970 (6) 0.0221 (2)
O3 0.61653 (8) 0.68768 (8) 0.42496 (6) 0.0209 (2)
O4 0.22108 (8) 0.77982 (8) 0.47938 (6) 0.01792 (19)
O5 0.18927 (8) 0.77876 (8) 0.62760 (6) 0.0217 (2)
N1 0.71846 (9) 0.83091 (9) 0.64775 (7) 0.0145 (2)
N2 0.58627 (9) 0.71116 (9) 0.70549 (7) 0.0143 (2)
N3 0.79091 (9) 0.81926 (9) 0.46197 (7) 0.0149 (2)
N4 0.33456 (9) 0.64839 (9) 0.58183 (7) 0.0158 (2)
C1 0.59511 (11) 0.82469 (11) 0.66601 (8) 0.0143 (2)
C2 0.78498 (11) 0.72200 (10) 0.67384 (8) 0.0142 (2)
C3 0.70112 (11) 0.64616 (11) 0.71027 (7) 0.0137 (2)
C4 0.73829 (11) 0.52998 (11) 0.74338 (8) 0.0157 (2)
H4 0.6828 0.4800 0.7679 0.019*
C5 0.86290 (11) 0.49150 (11) 0.73819 (8) 0.0174 (3)
H5 0.8907 0.4137 0.7591 0.021*
C6 0.94645 (11) 0.56687 (11) 0.70237 (8) 0.0176 (3)
H6 1.0288 0.5384 0.7000 0.021*
C7 0.90915 (11) 0.68422 (11) 0.66999 (8) 0.0162 (2)
H7 0.9653 0.7350 0.6468 0.019*
C8 0.76194 (11) 0.93510 (10) 0.60123 (8) 0.0159 (2)
H8A 0.8558 0.9432 0.6227 0.019*
H8B 0.7223 1.0086 0.6190 0.019*
C9 0.72673 (11) 0.92265 (11) 0.49385 (8) 0.0162 (2)
H9A 0.6330 0.9132 0.4724 0.019*
H9B 0.7516 0.9966 0.4659 0.019*
C10 0.72954 (11) 0.71504 (11) 0.42958 (8) 0.0160 (2)
C11 0.94356 (12) 0.69048 (12) 0.42409 (9) 0.0210 (3)
H11A 0.9846 0.6861 0.3709 0.025*
H11B 0.9977 0.6475 0.4771 0.025*
C12 0.92429 (11) 0.82316 (11) 0.45003 (8) 0.0170 (3)
H12A 0.9852 0.8466 0.5080 0.020*
H12B 0.9329 0.8785 0.3998 0.020*
C13 0.47432 (11) 0.67173 (11) 0.74094 (8) 0.0156 (2)
H13A 0.4262 0.7430 0.7533 0.019*
H13B 0.5050 0.6290 0.8002 0.019*
C14 0.38313 (11) 0.58849 (11) 0.67225 (8) 0.0169 (2)
H14A 0.4293 0.5147 0.6628 0.020*
H14B 0.3102 0.5655 0.6989 0.020*
C15 0.24555 (11) 0.73773 (11) 0.57032 (8) 0.0159 (2)
C16 0.31809 (12) 0.72690 (11) 0.43458 (9) 0.0198 (3)
H16A 0.3889 0.7837 0.4355 0.024*
H16B 0.2794 0.7048 0.3697 0.024*
C17 0.36658 (12) 0.61423 (11) 0.49327 (8) 0.0197 (3)
H17A 0.3204 0.5413 0.4665 0.024*
H17B 0.4596 0.6023 0.5006 0.024*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
O1 0.0189 (4) 0.0159 (4) 0.0217 (4) 0.0033 (3) 0.0056 (3) 0.0003 (3)
O2 0.0169 (4) 0.0205 (5) 0.0288 (5) −0.0003 (3) 0.0049 (3) −0.0081 (4)
O3 0.0160 (4) 0.0201 (5) 0.0261 (5) −0.0024 (3) 0.0038 (3) −0.0008 (4)
O4 0.0165 (4) 0.0186 (4) 0.0190 (4) 0.0030 (3) 0.0048 (3) 0.0007 (3)
O5 0.0178 (4) 0.0263 (5) 0.0222 (4) 0.0031 (4) 0.0069 (3) −0.0052 (4)
N1 0.0156 (5) 0.0134 (5) 0.0151 (5) 0.0001 (4) 0.0047 (4) 0.0010 (4)
N2 0.0135 (5) 0.0143 (5) 0.0155 (5) 0.0002 (4) 0.0044 (4) 0.0001 (4)
N3 0.0145 (5) 0.0147 (5) 0.0159 (5) −0.0007 (4) 0.0042 (4) −0.0003 (4)
N4 0.0161 (5) 0.0158 (5) 0.0155 (5) 0.0018 (4) 0.0037 (4) −0.0017 (4)
C1 0.0158 (6) 0.0145 (6) 0.0123 (5) −0.0005 (5) 0.0025 (4) −0.0022 (4)
C2 0.0164 (6) 0.0143 (6) 0.0108 (5) −0.0001 (5) 0.0010 (4) −0.0011 (4)
C3 0.0139 (5) 0.0159 (6) 0.0111 (5) −0.0006 (4) 0.0020 (4) −0.0023 (4)
C4 0.0184 (6) 0.0160 (6) 0.0125 (5) −0.0018 (5) 0.0031 (4) 0.0001 (4)
C5 0.0211 (6) 0.0153 (6) 0.0148 (5) 0.0034 (5) 0.0019 (4) 0.0014 (4)
C6 0.0157 (6) 0.0212 (6) 0.0158 (5) 0.0038 (5) 0.0033 (4) −0.0002 (5)
C7 0.0163 (6) 0.0188 (6) 0.0141 (5) −0.0013 (5) 0.0047 (4) 0.0001 (4)
C8 0.0181 (6) 0.0118 (6) 0.0183 (6) −0.0016 (5) 0.0054 (4) −0.0003 (4)
C9 0.0179 (6) 0.0133 (6) 0.0175 (6) 0.0020 (5) 0.0042 (4) 0.0017 (4)
C10 0.0177 (6) 0.0163 (6) 0.0136 (5) 0.0017 (5) 0.0024 (4) 0.0017 (4)
C11 0.0149 (6) 0.0240 (7) 0.0241 (6) 0.0000 (5) 0.0049 (5) −0.0046 (5)
C12 0.0146 (6) 0.0201 (6) 0.0169 (6) −0.0007 (5) 0.0046 (4) 0.0016 (5)
C13 0.0147 (6) 0.0172 (6) 0.0159 (5) −0.0010 (5) 0.0057 (4) −0.0003 (5)
C14 0.0166 (6) 0.0161 (6) 0.0179 (6) −0.0008 (5) 0.0038 (4) 0.0012 (5)
C15 0.0121 (5) 0.0165 (6) 0.0183 (6) −0.0028 (5) 0.0020 (4) −0.0030 (5)
C16 0.0215 (6) 0.0197 (6) 0.0206 (6) 0.0029 (5) 0.0097 (5) 0.0006 (5)
C17 0.0246 (6) 0.0175 (6) 0.0197 (6) 0.0033 (5) 0.0106 (5) −0.0001 (5)
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Geometric parameters (Å, °)

O1—C1 1.2252 (14) C5—H5 0.9300
O2—C10 1.3612 (14) C6—C7 1.3955 (17)
O2—C11 1.4510 (15) C6—H6 0.9300
O3—C10 1.2144 (14) C7—H7 0.9300
O4—C15 1.3692 (14) C8—C9 1.5273 (16)
O4—C16 1.4531 (14) C8—H8A 0.9700
O5—C15 1.2147 (14) C8—H8B 0.9700
N1—C1 1.3862 (15) C9—H9A 0.9700
N1—C2 1.3926 (15) C9—H9B 0.9700
N1—C8 1.4545 (15) C11—C12 1.5282 (17)
N2—C1 1.3831 (15) C11—H11A 0.9700
N2—C3 1.3921 (15) C11—H11B 0.9700
N2—C13 1.4570 (14) C12—H12A 0.9700
N3—C10 1.3439 (16) C12—H12B 0.9700
N3—C9 1.4496 (15) C13—C14 1.5215 (16)
N3—C12 1.4552 (14) C13—H13A 0.9700
N4—C15 1.3396 (15) C13—H13B 0.9700
N4—C17 1.4542 (15) C14—H14A 0.9700
N4—C14 1.4546 (15) C14—H14B 0.9700
C2—C7 1.3853 (16) C16—C17 1.5220 (17)
C2—C3 1.4027 (16) C16—H16A 0.9700
C3—C4 1.3862 (17) C16—H16B 0.9700
C4—C5 1.3971 (17) C17—H17A 0.9700
C4—H4 0.9300 C17—H17B 0.9700
C5—C6 1.3927 (17)
C10—O2—C11 108.99 (9) C8—C9—H9B 109.2
C15—O4—C16 107.65 (9) H9A—C9—H9B 107.9
C1—N1—C2 109.92 (9) O3—C10—N3 128.03 (11)
C1—N1—C8 122.48 (10) O3—C10—O2 122.02 (11)
C2—N1—C8 127.44 (10) N3—C10—O2 109.95 (10)
C1—N2—C3 109.94 (9) O2—C11—C12 105.27 (9)
C1—N2—C13 123.46 (9) O2—C11—H11A 110.7
C3—N2—C13 126.51 (10) C12—C11—H11A 110.7
C10—N3—C9 123.71 (10) O2—C11—H11B 110.7
C10—N3—C12 112.52 (10) C12—C11—H11B 110.7
C9—N3—C12 123.31 (10) H11A—C11—H11B 108.8
C15—N4—C17 112.04 (10) N3—C12—C11 100.84 (9)
C15—N4—C14 122.29 (10) N3—C12—H12A 111.6
C17—N4—C14 125.49 (10) C11—C12—H12A 111.6
O1—C1—N2 127.34 (11) N3—C12—H12B 111.6
O1—C1—N1 126.44 (11) C11—C12—H12B 111.6
N2—C1—N1 106.22 (9) H12A—C12—H12B 109.4
C7—C2—N1 131.76 (11) N2—C13—C14 112.67 (9)
C7—C2—C3 121.35 (11) N2—C13—H13A 109.1
N1—C2—C3 106.88 (10) C14—C13—H13A 109.1
C4—C3—N2 131.36 (11) N2—C13—H13B 109.1
C4—C3—C2 121.60 (11) C14—C13—H13B 109.1
N2—C3—C2 107.03 (10) H13A—C13—H13B 107.8
C3—C4—C5 116.91 (11) N4—C14—C13 111.20 (10)
C3—C4—H4 121.5 N4—C14—H14A 109.4
C5—C4—H4 121.5 C13—C14—H14A 109.4
C6—C5—C4 121.54 (11) N4—C14—H14B 109.4
C6—C5—H5 119.2 C13—C14—H14B 109.4
C4—C5—H5 119.2 H14A—C14—H14B 108.0
C5—C6—C7 121.36 (11) O5—C15—N4 128.51 (11)
C5—C6—H6 119.3 O5—C15—O4 121.68 (11)
C7—C6—H6 119.3 N4—C15—O4 109.79 (10)
C2—C7—C6 117.21 (11) O4—C16—C17 104.61 (9)
C2—C7—H7 121.4 O4—C16—H16A 110.8
C6—C7—H7 121.4 C17—C16—H16A 110.8
N1—C8—C9 112.19 (9) O4—C16—H16B 110.8
N1—C8—H8A 109.2 C17—C16—H16B 110.8
C9—C8—H8A 109.2 H16A—C16—H16B 108.9
N1—C8—H8B 109.2 N4—C17—C16 99.92 (9)
C9—C8—H8B 109.2 N4—C17—H17A 111.8
H8A—C8—H8B 107.9 C16—C17—H17A 111.8
N3—C9—C8 112.07 (9) N4—C17—H17B 111.8
N3—C9—H9A 109.2 C16—C17—H17B 111.8
C8—C9—H9A 109.2 H17A—C17—H17B 109.5
N3—C9—H9B 109.2
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2373).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810052141/fj2373sup1.cif

e-67-0o362-sup1.cif (18.5KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052141/fj2373Isup2.hkl

e-67-0o362-Isup2.hkl (143.1KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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