[Journal logo]

Volume 68 
Part 11 
Page o3069  
November 2012  

Received 15 September 2012
Accepted 1 October 2012
Online 6 October 2012

[im2402sup1]
[3d view]

[Cited in]
[Download citation]
Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.141
Data-to-parameter ratio = 23.3
Details
Open access

1-Dodecyl-1H-benzo[d]imidazol-2(3H)-one

Dounia Belaziz,a* Youssef Kandri Rodi,a Fouad Ouazzani Chahdi,a El Mokhtar Essassi,b,c Mohamed Saadid and Lahcen El Ammarid

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, C19H30N2O, the fused ring system is essentially planar, the maximum deviation from the mean plane being 0.013 (2) Å for the N atom bearing the dodecyl chain. The 1-dodecyl group is almost perpendicular to the 1H-benzo[d]imidazol-2(3H)-one plane as indicated by the dihedral angle of 82.9 (2)°between planes through the fused ring system and the first three C atoms of the chain. The C-C-C-C torsion angles (about ±179°) of the dodecyl group indicate an antiperiplanar conformation. In the crystal, inversion dimers are formed by pairs of N-H...O hydrogen bonds.

Related literature

For pharmacological and biochemical properties of benzimidazoles and their derivatives, see: Al Muhaimeed (1997[Al Muhaimeed, H. (1997). J. Int. Med. Res. 25, 175-181.]); Scott et al. (2002[Scott, L. J., Dunn, C. J., Mallarkey, G. & Sharpe, M. (2002). Drugs, 62, 1503-1538.]); Nakano et al. (2000[Nakano, H., Inoue, T., Kawasaki, N., Miyataka, H., Matsumoto, H., Taguchi, T., Inagaki, N., Nagai, H. & Satoh, T. (2000). Bioorg. Med. Chem. 8, 373-380.]); Zhu et al. (2000[Zhu, Z., Lippa, B., Drach, J. C. & Townsend, L. B. (2000). J. Med. Chem. 43, 2430-2437.]); Zarrinmayeh et al. (1998[Zarrinmayeh, H., Nunes, A. M., Ornstein, P. L., Zimmerman, D. M., Arnold, M. B., Schober, D. A., Gackenheimer, S. L., Bruns, R. F., Hipskind, P. A., Britton, T. C., Cantrell, B. E. & Gehlert, D. R. (1998). J. Med. Chem. 41, 2709-2719.]). For compounds with closely related structures, see: Ouzidan et al. (2011[Ouzidan, Y., Kandri Rodi, Y., Butcher, R. J., Essassi, E. M. & El Ammari, L. (2011). Acta Cryst. E67, o283.]); Kandri Rodi et al. (2011[Kandri Rodi, Y., Ouazzani Chahdi, F., Essassi, E. M., Luis, S. V., Bolte, M. & El Ammari, L. (2011). Acta Cryst. E67, o3340-o3341.]); Belaziz et al. (2012[Belaziz, D., Kandri Rodi, Y., Essassi, E. M. & El Ammari, L. (2012). Acta Cryst. E68, o1276.]).

[Scheme 1]

Experimental

Crystal data

  • C19H30N2O

  • Mr = 302.45

  • Monoclinic, C 2/c

  • a = 38.3223 (14) Å

  • b = 4.8318 (2) Å

  • c = 21.9831 (8) Å

  • [beta] = 117.843 (2)°

  • V = 3599.3 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 296 K

  • 0.47 × 0.31 × 0.14 mm
Data collection

  • Bruker X8 APEX Diffractometer

  • 29002 measured reflections

  • 4637 independent reflections

  • 3179 reflections with I > 2[sigma](I)

  • Rint = 0.028
Refinement

  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.141

  • S = 1.01

  • 4637 reflections

  • 199 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 0.86 1.97 2.815 (1) 168
Symmetry code: (i) -x, -y+2, -z.

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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) 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: IM2402 ).

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

References

Al Muhaimeed, H. (1997). J. Int. Med. Res. 25, 175-181.  [ChemPort] [PubMed]
Belaziz, D., Kandri Rodi, Y., Essassi, E. M. & El Ammari, L. (2012). Acta Cryst. E68, o1276.  [CSD] [CrossRef] [details]
Bruker (2005). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Kandri Rodi, Y., Ouazzani Chahdi, F., Essassi, E. M., Luis, S. V., Bolte, M. & El Ammari, L. (2011). Acta Cryst. E67, o3340-o3341.  [CSD] [CrossRef] [details]
Nakano, H., Inoue, T., Kawasaki, N., Miyataka, H., Matsumoto, H., Taguchi, T., Inagaki, N., Nagai, H. & Satoh, T. (2000). Bioorg. Med. Chem. 8, 373-380.  [CrossRef] [PubMed] [ChemPort]
Ouzidan, Y., Kandri Rodi, Y., Butcher, R. J., Essassi, E. M. & El Ammari, L. (2011). Acta Cryst. E67, o283.  [CSD] [CrossRef] [details]
Scott, L. J., Dunn, C. J., Mallarkey, G. & Sharpe, M. (2002). Drugs, 62, 1503-1538.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Zarrinmayeh, H., Nunes, A. M., Ornstein, P. L., Zimmerman, D. M., Arnold, M. B., Schober, D. A., Gackenheimer, S. L., Bruns, R. F., Hipskind, P. A., Britton, T. C., Cantrell, B. E. & Gehlert, D. R. (1998). J. Med. Chem. 41, 2709-2719.  [ISI] [CrossRef] [ChemPort] [PubMed]
Zhu, Z., Lippa, B., Drach, J. C. & Townsend, L. B. (2000). J. Med. Chem. 43, 2430-2437.  [ISI] [CrossRef] [PubMed] [ChemPort]

Acta Cryst (2012). E68, o3069  [ doi:10.1107/S1600536812041189 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.