organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

1-n-Decyl-5-nitro-1H-benzimidazol-2(3H)-one

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 27 January 2011; accepted 6 February 2011; online 12 February 2011)

The benzimidazolone part of the title mol­ecule, C17H25N3O3, is almost planar (r.m.s. deviation = 0.016 Å) and its mean plane is aligned at 7.9 (4) ° with respect to the mean plane of the nitro substituent. In the crystal, two mol­ecules are disposed about a center of inversion, generating a N—H⋯O hydrogen-bonded cyclic dimer with a R22(8) graph-set motif.

Related literature

For the crystal structure of 1-isopropenyl-1H-benzimidazol-2(3H)-one, see: Saber et al. (2010[Saber, A., Zouihri, H., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o1409.]) and for 5-nitro-1-n-octyl-1H-benzimidazol-2(3H)-one, see: Ouzidan et al. (2011[Ouzidan, Y., Kandri Rodi, Y., Saffon, N., Essassi, E. M. & Ng, S. W. (2011). Acta Cryst. E67, o558.]). For graph-set notation, see: Etter (1990[Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.]).

[Scheme 1]

Experimental

Crystal data
  • C17H25N3O3

  • Mr = 319.40

  • Triclinic, [P \overline 1]

  • a = 5.4933 (2) Å

  • b = 10.3063 (4) Å

  • c = 16.1655 (6) Å

  • α = 106.504 (2)°

  • β = 98.545 (2)°

  • γ = 96.809 (2)°

  • V = 855.21 (6) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 293 K

  • 0.32 × 0.06 × 0.04 mm

Data collection
  • Bruker APEXII diffractometer

  • 10701 measured reflections

  • 2971 independent reflections

  • 1600 reflections with I > 2σ(I)

  • Rint = 0.068

Refinement
  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 0.175

  • S = 0.89

  • 2971 reflections

  • 209 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.31 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O1i 0.88 1.92 2.784 (3) 168
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

Tetraalkylammonium halides are used as phase-transfer catalyst in the synthesis of alkyl-substituted benzimidazolones. A previous study reported the 1-isopropenyl derivative in which the amino –NH unit forms a hydrogen bond to the inversion-related molecule to generate a hydrogen-bonded dimer (Saber et al., 2010). The present compound (Scheme I) features a long n-octyl chain that adopts an extended zigzag conformation (Fig. 1). The benzimidazolone part of the C17H25N3O3 molecule is planar (r.m.s. deviation 0.016 Å) and its mean plane is aligned at 7.9 (4) ° with respect to the mean plane of the nitro substituent. Two molecules are disposed about a center of inversion to generate a hydrogen-bonded cyclic dimer (Table 1), whose hydrogen-bonding motif is described by the R22(8) graph set (Etter, 1990).

Related literature top

For the crystal structure of 1-isopropenyl-1H-benzimidazol-2(3H)-one, see: Saber et al. (2010) and for 5-nitro-1-n-octyl-1H-benzimidazol-2(3H)-one, see: Ouzidan et al. (2011). For graph-set notation, see: Etter (1990).

Experimental top

To 5-nitro-1H-benzoimidazol-2(3H)-one (0.2 g, 1.1 mmol), potassium carbonate (0.30 g, 2.2 mmol) and tetra-n-butylammonium bromide (0.07 g, 0.2 mmol) in DMF (15 ml) was added 1-bromo-n-decane (0.46 ml, 2.2 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 chromatography on a column of silica gel with ethyl acetate/hexane (1/2) as eluent. The compound was recrystallized from diethyl ether to give colorless crystals.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93–0.97, N–H 0.88 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2–1.5Ueq(C,N).

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
[Figure 1] Fig. 1. Thermal ellipsoid plot drawn at the 50% probability level (Barbour, 2001), of two molecules of C17H25N3O3 disposed about a center of inversion.
1-n-decyl-5-nitro-1H-benzimidazol-2(3H)-one top
Crystal data top
C17H25N3O3Z = 2
Mr = 319.40F(000) = 344
Triclinic, P1Dx = 1.240 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.4933 (2) ÅCell parameters from 1521 reflections
b = 10.3063 (4) Åθ = 2.7–27.3°
c = 16.1655 (6) ŵ = 0.09 mm1
α = 106.504 (2)°T = 293 K
β = 98.545 (2)°Prism, colorless
γ = 96.809 (2)°0.32 × 0.06 × 0.04 mm
V = 855.21 (6) Å3
Data collection top
Bruker APEXII
diffractometer
1600 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.068
Graphite monochromatorθmax = 25.0°, θmin = 3.9°
ϕ and ω scansh = 66
10701 measured reflectionsk = 1012
2971 independent reflectionsl = 1919
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.175 w = 1/[σ2(Fo2) + (0.1056P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.89(Δ/σ)max = 0.001
2971 reflectionsΔρmax = 0.30 e Å3
209 parametersΔρmin = 0.31 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.034 (6)
Crystal data top
C17H25N3O3γ = 96.809 (2)°
Mr = 319.40V = 855.21 (6) Å3
Triclinic, P1Z = 2
a = 5.4933 (2) ÅMo Kα radiation
b = 10.3063 (4) ŵ = 0.09 mm1
c = 16.1655 (6) ÅT = 293 K
α = 106.504 (2)°0.32 × 0.06 × 0.04 mm
β = 98.545 (2)°
Data collection top
Bruker APEXII
diffractometer
1600 reflections with I > 2σ(I)
10701 measured reflectionsRint = 0.068
2971 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0550 restraints
wR(F2) = 0.175H-atom parameters constrained
S = 0.89Δρmax = 0.30 e Å3
2971 reflectionsΔρmin = 0.31 e Å3
209 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.6868 (3)0.57512 (19)0.61197 (12)0.0413 (6)
O20.8896 (4)0.0690 (2)0.29737 (16)0.0579 (7)
O31.2510 (4)0.0845 (2)0.36526 (16)0.0680 (7)
N10.7157 (4)0.3830 (2)0.49844 (15)0.0357 (6)
H10.58630.38320.45920.043*
N20.9999 (4)0.4426 (2)0.61946 (15)0.0337 (6)
N31.0691 (5)0.0264 (2)0.35868 (19)0.0482 (7)
C10.7879 (5)0.4765 (3)0.57918 (19)0.0354 (7)
C20.8734 (5)0.2871 (3)0.48616 (18)0.0328 (7)
C30.8717 (5)0.1718 (3)0.41760 (19)0.0371 (7)
H30.74830.14350.36710.044*
C41.0672 (5)0.1002 (3)0.4288 (2)0.0380 (7)
C51.2516 (5)0.1396 (3)0.5022 (2)0.0397 (8)
H51.38010.08900.50520.048*
C61.2493 (5)0.2538 (3)0.5717 (2)0.0385 (7)
H61.37230.28050.62230.046*
C71.0566 (5)0.3268 (3)0.56298 (19)0.0347 (7)
C81.1434 (5)0.5230 (3)0.70567 (18)0.0399 (7)
H8A1.07860.60780.72540.048*
H8B1.31570.54690.70070.048*
C91.1361 (5)0.4479 (3)0.77434 (19)0.0420 (7)
H9A1.19540.36180.75300.050*
H9B1.25190.50270.82760.050*
C100.8830 (5)0.4174 (3)0.7976 (2)0.0457 (8)
H10A0.76780.35750.74570.055*
H10B0.81850.50230.81710.055*
C110.8982 (5)0.3489 (3)0.8699 (2)0.0463 (8)
H11A0.95930.26320.84910.056*
H11B1.02020.40760.92040.056*
C120.6562 (6)0.3190 (3)0.8998 (2)0.0516 (9)
H12A0.58960.40360.91790.062*
H12B0.53660.25560.85050.062*
C130.6824 (6)0.2585 (3)0.9749 (2)0.0492 (8)
H13A0.80600.32101.02340.059*
H13B0.74570.17310.95610.059*
C140.4445 (6)0.2305 (3)1.0082 (2)0.0535 (9)
H14A0.37540.31461.02350.064*
H14B0.32440.16340.96080.064*
C150.4751 (6)0.1780 (3)1.0874 (2)0.0531 (9)
H15A0.54000.09261.07170.064*
H15B0.59810.24391.13440.064*
C160.2378 (7)0.1537 (4)1.1214 (2)0.0692 (11)
H16A0.11890.08251.07600.083*
H16B0.16590.23711.13310.083*
C170.2764 (8)0.1116 (4)1.2043 (3)0.0862 (13)
H17A0.11890.09651.22200.129*
H17B0.38880.18321.25030.129*
H17C0.34600.02861.19320.129*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0513 (12)0.0398 (11)0.0402 (12)0.0189 (10)0.0180 (10)0.0148 (10)
O20.0723 (16)0.0459 (14)0.0531 (16)0.0082 (12)0.0178 (14)0.0095 (12)
O30.0794 (17)0.0556 (14)0.0770 (18)0.0342 (13)0.0326 (14)0.0149 (13)
N10.0405 (13)0.0385 (13)0.0363 (15)0.0144 (11)0.0142 (11)0.0176 (13)
N20.0368 (13)0.0354 (13)0.0344 (14)0.0097 (10)0.0119 (11)0.0151 (12)
N30.0618 (18)0.0381 (15)0.056 (2)0.0155 (14)0.0303 (16)0.0194 (14)
C10.0446 (17)0.0345 (16)0.0357 (18)0.0080 (14)0.0186 (14)0.0179 (15)
C20.0383 (16)0.0332 (16)0.0355 (18)0.0072 (13)0.0170 (14)0.0184 (14)
C30.0440 (17)0.0374 (16)0.0355 (18)0.0054 (13)0.0146 (14)0.0172 (15)
C40.0491 (18)0.0321 (16)0.0444 (19)0.0096 (14)0.0273 (16)0.0192 (15)
C50.0412 (17)0.0383 (17)0.051 (2)0.0139 (14)0.0212 (16)0.0215 (16)
C60.0371 (16)0.0431 (17)0.0436 (19)0.0086 (13)0.0137 (14)0.0226 (16)
C70.0415 (16)0.0346 (16)0.0376 (18)0.0073 (13)0.0212 (14)0.0191 (14)
C80.0435 (16)0.0414 (17)0.0352 (18)0.0068 (13)0.0102 (14)0.0114 (15)
C90.0466 (17)0.0414 (17)0.0382 (18)0.0102 (14)0.0075 (14)0.0119 (14)
C100.0541 (19)0.0456 (18)0.044 (2)0.0130 (15)0.0156 (16)0.0185 (16)
C110.0561 (19)0.0483 (18)0.0399 (19)0.0123 (15)0.0140 (15)0.0183 (16)
C120.064 (2)0.0493 (19)0.050 (2)0.0120 (16)0.0166 (17)0.0237 (17)
C130.059 (2)0.0508 (19)0.043 (2)0.0115 (16)0.0125 (16)0.0199 (16)
C140.060 (2)0.056 (2)0.054 (2)0.0110 (16)0.0165 (17)0.0275 (18)
C150.070 (2)0.0456 (18)0.046 (2)0.0063 (16)0.0131 (18)0.0188 (17)
C160.086 (3)0.071 (2)0.068 (3)0.017 (2)0.036 (2)0.037 (2)
C170.136 (4)0.076 (3)0.063 (3)0.012 (3)0.041 (3)0.038 (2)
Geometric parameters (Å, º) top
O1—C11.240 (3)C10—C111.525 (4)
O2—N31.228 (3)C10—H10A0.9700
O3—N31.231 (3)C10—H10B0.9700
N1—C11.353 (3)C11—C121.508 (4)
N1—C21.382 (3)C11—H11A0.9700
N1—H10.8800C11—H11B0.9700
N2—C11.379 (3)C12—C131.511 (4)
N2—C71.382 (3)C12—H12A0.9700
N2—C81.454 (4)C12—H12B0.9700
N3—C41.468 (4)C13—C141.513 (4)
C2—C31.374 (4)C13—H13A0.9700
C2—C71.402 (4)C13—H13B0.9700
C3—C41.391 (4)C14—C151.520 (4)
C3—H30.9300C14—H14A0.9700
C4—C51.367 (4)C14—H14B0.9700
C5—C61.380 (4)C15—C161.509 (4)
C5—H50.9300C15—H15A0.9700
C6—C71.382 (3)C15—H15B0.9700
C6—H60.9300C16—C171.517 (5)
C8—C91.526 (4)C16—H16A0.9700
C8—H8A0.9700C16—H16B0.9700
C8—H8B0.9700C17—H17A0.9600
C9—C101.514 (4)C17—H17B0.9600
C9—H9A0.9700C17—H17C0.9600
C9—H9B0.9700
C1—N1—C2110.5 (2)C9—C10—H10B109.3
C1—N1—H1124.7C11—C10—H10B109.3
C2—N1—H1124.7H10A—C10—H10B108.0
C1—N2—C7109.0 (2)C12—C11—C10115.4 (2)
C1—N2—C8124.0 (2)C12—C11—H11A108.4
C7—N2—C8126.9 (2)C10—C11—H11A108.4
O2—N3—O3123.7 (3)C12—C11—H11B108.4
O2—N3—C4118.5 (2)C10—C11—H11B108.4
O3—N3—C4117.8 (3)H11A—C11—H11B107.5
O1—C1—N1127.5 (3)C13—C12—C11113.7 (2)
O1—C1—N2125.5 (3)C13—C12—H12A108.8
N1—C1—N2107.0 (2)C11—C12—H12A108.8
C3—C2—N1132.1 (3)C13—C12—H12B108.8
C3—C2—C7121.8 (2)C11—C12—H12B108.8
N1—C2—C7106.1 (2)H12A—C12—H12B107.7
C2—C3—C4115.5 (3)C12—C13—C14115.2 (2)
C2—C3—H3122.3C12—C13—H13A108.5
C4—C3—H3122.3C14—C13—H13A108.5
C5—C4—C3123.6 (3)C12—C13—H13B108.5
C5—C4—N3118.8 (3)C14—C13—H13B108.5
C3—C4—N3117.6 (3)H13A—C13—H13B107.5
C4—C5—C6120.7 (2)C15—C14—C13115.0 (3)
C4—C5—H5119.6C15—C14—H14A108.5
C6—C5—H5119.6C13—C14—H14A108.5
C7—C6—C5117.2 (3)C15—C14—H14B108.5
C7—C6—H6121.4C13—C14—H14B108.5
C5—C6—H6121.4H14A—C14—H14B107.5
N2—C7—C6131.5 (3)C16—C15—C14114.5 (3)
N2—C7—C2107.3 (2)C16—C15—H15A108.6
C6—C7—C2121.2 (3)C14—C15—H15A108.6
N2—C8—C9113.2 (2)C16—C15—H15B108.6
N2—C8—H8A108.9C14—C15—H15B108.6
C9—C8—H8A108.9H15A—C15—H15B107.6
N2—C8—H8B108.9C15—C16—C17113.5 (3)
C9—C8—H8B108.9C15—C16—H16A108.9
H8A—C8—H8B107.8C17—C16—H16A108.9
C10—C9—C8115.7 (2)C15—C16—H16B108.9
C10—C9—H9A108.4C17—C16—H16B108.9
C8—C9—H9A108.4H16A—C16—H16B107.7
C10—C9—H9B108.4C16—C17—H17A109.5
C8—C9—H9B108.4C16—C17—H17B109.5
H9A—C9—H9B107.4H17A—C17—H17B109.5
C9—C10—C11111.6 (2)C16—C17—H17C109.5
C9—C10—H10A109.3H17A—C17—H17C109.5
C11—C10—H10A109.3H17B—C17—H17C109.5
C2—N1—C1—O1179.0 (2)C8—N2—C7—C62.5 (4)
C2—N1—C1—N21.4 (3)C1—N2—C7—C20.7 (3)
C7—N2—C1—O1180.0 (2)C8—N2—C7—C2177.4 (2)
C8—N2—C1—O13.2 (4)C5—C6—C7—N2179.3 (3)
C7—N2—C1—N10.4 (3)C5—C6—C7—C20.8 (4)
C8—N2—C1—N1176.4 (2)C3—C2—C7—N2177.8 (2)
C1—N1—C2—C3177.4 (3)N1—C2—C7—N21.4 (3)
C1—N1—C2—C71.7 (3)C3—C2—C7—C62.3 (4)
N1—C2—C3—C4179.3 (2)N1—C2—C7—C6178.4 (2)
C7—C2—C3—C41.7 (4)C1—N2—C8—C9114.0 (3)
C2—C3—C4—C50.3 (4)C7—N2—C8—C969.7 (3)
C2—C3—C4—N3178.0 (2)N2—C8—C9—C1065.3 (3)
O2—N3—C4—C5172.5 (2)C8—C9—C10—C11177.1 (2)
O3—N3—C4—C57.0 (4)C9—C10—C11—C12177.9 (3)
O2—N3—C4—C35.8 (4)C10—C11—C12—C13176.8 (3)
O3—N3—C4—C3174.7 (2)C11—C12—C13—C14178.5 (3)
C3—C4—C5—C61.8 (4)C12—C13—C14—C15176.4 (3)
N3—C4—C5—C6176.5 (2)C13—C14—C15—C16178.6 (3)
C4—C5—C6—C71.2 (4)C14—C15—C16—C17175.7 (3)
C1—N2—C7—C6179.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.881.922.784 (3)168
Symmetry code: (i) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC17H25N3O3
Mr319.40
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)5.4933 (2), 10.3063 (4), 16.1655 (6)
α, β, γ (°)106.504 (2), 98.545 (2), 96.809 (2)
V3)855.21 (6)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.32 × 0.06 × 0.04
Data collection
DiffractometerBruker APEXII
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
10701, 2971, 1600
Rint0.068
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.175, 0.89
No. of reflections2971
No. of parameters209
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.31

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.881.922.784 (3)168
Symmetry code: (i) x+1, y+1, z+1.
 

Acknowledgements

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

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
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