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Volume 69 
Part 7 
Page o1159  
July 2013  

Received 31 May 2013
Accepted 17 June 2013
Online 26 June 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.004 Å
R = 0.047
wR = 0.126
Data-to-parameter ratio = 9.4
Details
Open access

5-Nitro-1,3-bis(prop-2-ynyl)-1H-1,3-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,bUnité Chimie Inorganique, Matériaux et Interfaces (CIMI), Université d'Angers, CNRS UMR 6200, France,cInstitute of Solid State Physics RAS, 142432 Chernogolovka MD, Russia,dLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batouta, Rabat, Morocco, and eLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014 Rabat, Morocco
Correspondence e-mail: k_misbahi@yahoo.fr

The title compound, C13H9N3O3, crystallizes with two identical but differently oriented molecules in the asymmetric unit, the dihedral angle between the fused-ring systems of the two molecules being 64.39 (7)°. The two prop-2-ynyl chains are located on opposite sides of the molecule and are nearly perpendicular to the fused ring plane, as indicated by the C-N-C-C torsion angles in the range 106.0 (3)-113.4 (3)°. In the crystal, the two molecules are linked through C-H...O hydrogen bonds into dimers, which are subsequently linked by further C-H...O interactions, building a three-dimensional network.

Related literature

For the biological activity of benzimidazole derivatives, see: Horton et al. (2003[Horton, D. A., Bourne, G. T. & Smythe, M. L. (2003). Chem. Rev. 103, 893-930.]); Kim et al. (1996[Kim, J. S., Gatto, B., Yu, C., Liu, A., Liu, L. F. & La Voie, E. J. (1996). J. Med. Chem. 39, 992-998.]); Roth et al. (1997[Roth, T., Morningstar, M. L., Boyer, P. L., Hughes, S. H., Buckheit, R. W. & Michejda, C. J. (1997). J. Med. Chem. 40, 4199-4207.]). For examples of benzimidazol-2-one derivatives, see: Ouzidan et al. (2011a[Ouzidan, Y., Kandri Rodi, Y., Butcher, R. J., Essassi, E. M. & El Ammari, L. (2011a). Acta Cryst. E67, o283.],b[Ouzidan, Y., Kandri Rodi, Y., Fronczek, F. R., Venkatraman, R., El Ammari, L. & Essassi, E. M. (2011b). Acta Cryst. E67, o362-o363.],c[Ouzidan, Y., Kandri Rodi, Y., Jasinski, J. P., Butcher, R. J., Golen, J. A. & El Ammari, L. (2011c). Acta Cryst. E67, o1091.]).

[Scheme 1]

Experimental

Crystal data
  • C13H9N3O3

  • Mr = 255.23

  • Orthorhombic, P c a 21

  • a = 20.0988 (16) Å

  • b = 4.2645 (3) Å

  • c = 28.669 (2) Å

  • V = 2457.3 (3) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 150 K

  • 0.48 × 0.2 × 0.13 mm

Data collection
  • Agilent Xcalibur (Ruby, Gemini) diffractometer

  • Absorption correction: multi-scan (ABSFAC; Agilent, 2012[Agilent (2012). ABSFAC and CrysAlis PRO. Agilent Technologies Ltd, Yarnton, Oxfordshire, England.]) Tmin = 0.520, Tmax = 1

  • 16703 measured reflections

  • 3233 independent reflections

  • 2971 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.126

  • S = 1.05

  • 3233 reflections

  • 343 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.48 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C5-H5...O6i 0.95 2.43 3.316 (3) 155
C8-H8A...O4ii 0.99 2.28 3.186 (3) 151
C11-H11A...O6i 0.99 2.45 3.257 (4) 139
C13-H13...O2iii 0.95 2.32 3.205 (4) 155
C21-H21B...O1iv 0.99 2.27 3.191 (3) 154
C24-H24B...O3 0.99 2.49 3.350 (4) 146
C26-H26...O5i 0.95 2.40 3.320 (4) 164
Symmetry codes: (i) [x-{\script{1\over 2}}, -y-1, z]; (ii) [-x+{\script{1\over 2}}, y-1, z+{\script{1\over 2}}]; (iii) [x-{\script{1\over 2}}, -y+1, z]; (iv) [-x+{\script{1\over 2}}, y+1, z-{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). ABSFAC and CrysAlis PRO. Agilent Technologies Ltd, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KJ2228 ).


References

Agilent (2012). ABSFAC and CrysAlis PRO. Agilent Technologies Ltd, Yarnton, Oxfordshire, England.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Horton, D. A., Bourne, G. T. & Smythe, M. L. (2003). Chem. Rev. 103, 893-930.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Kim, J. S., Gatto, B., Yu, C., Liu, A., Liu, L. F. & La Voie, E. J. (1996). J. Med. Chem. 39, 992-998.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Ouzidan, Y., Kandri Rodi, Y., Butcher, R. J., Essassi, E. M. & El Ammari, L. (2011a). Acta Cryst. E67, o283.  [CSD] [CrossRef] [IUCr Journals]
Ouzidan, Y., Kandri Rodi, Y., Fronczek, F. R., Venkatraman, R., El Ammari, L. & Essassi, E. M. (2011b). Acta Cryst. E67, o362-o363.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Ouzidan, Y., Kandri Rodi, Y., Jasinski, J. P., Butcher, R. J., Golen, J. A. & El Ammari, L. (2011c). Acta Cryst. E67, o1091.  [CSD] [CrossRef] [IUCr Journals]
Roth, T., Morningstar, M. L., Boyer, P. L., Hughes, S. H., Buckheit, R. W. & Michejda, C. J. (1997). J. Med. Chem. 40, 4199-4207.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1159  [ doi:10.1107/S1600536813016814 ]

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