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Volume 69 
Part 5 
Pages o641-o642  
May 2013  

Received 19 March 2013
Accepted 26 March 2013
Online 5 April 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.051
wR = 0.145
Data-to-parameter ratio = 12.9
Details
Open access

Ethyl 2-oxo-3-(3-phthalimidopropyl)-2,3-dihydro-1H-1,3-benzimidazole-1-carboxylate

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, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014 Rabat, Morocco,cInstitute of Nanomaterials and Nanotechnology, MASCIR, Rabat, Morocco, and dLaboratoire de Chimie du Solide Appliquée, Université Mohammed V-Agdal, Faculté des Sciences, Avenue Ibn Battouta, BP 1014 Rabat, Morocco
Correspondence e-mail: d_belaziz@yahoo.fr

In the title compound, C21H19N3O5, the phthalimide and benzamidazole ring systems are linked by a propyl chain. The benzamidazole unit also carries an ethoxycarbonyl substituent. The phthalimido and benzimidazole ring systems are essentially planar, the maximum deviations from their mean planes being 0.008 (2) and 0.020 (2) Å, respectively. The two ring systems are almost orthogonal to one another, making a dihedral angle of 82.37 (8)°. In the crystal, C-H...O hydrogen bonds and C-H...[pi] contacts stack the molecules along the b axis.

Related literature

For the pharmacological and biochemical properties of benzamidazoles, see: Gravatt et al. (1994[Gravatt, G. L., Baguley, B. C., Wilson, W. R. & Denny, W. A. (1994). J. Med. Chem. 37, 4338-4345.]); 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.]); 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.]); Spasov et al. (1999[Spasov, A. A., Yozhitsa, I. N., Bugaeva, L. I. & Anisimova, V. A. (1999). Pharm. Chem. J. 33, 232-243.]). For their use as intermediates in many organic reactions, see: Bai et al. (2001[Bai, Y., Lu, J., Shi, Z. & Yang, B. (2001). Synlett, 12, 544-546.]); Hasegawa et al. (1999[Hasegawa, E., Yoneoka, A., Suzuki, K., Kato, T., Kitazume, T. & Yangi, K. (1999). Tetrahedron, 55, 12957-12968.]). For their use as ligands to transition metals, see: Bouwman et al. (1990[Bouwman, E., Driessen, W. L. & Reedjik, J. (1990). Coord. Chem. Rev. 104, 143-172.]). For a related structure, see: Belaziz et al. (2013[Belaziz, D., Kandri Rodi, Y., Ouazzani Chahdi, F., Essassi, E. M., Saadi, M. & El Ammari, L. (2013). Acta Cryst. E69, o122.]).

[Scheme 1]

Experimental

Crystal data
  • C21H19N3O5

  • Mr = 393.39

  • Triclinic, [P \overline 1]

  • a = 5.2850 (7) Å

  • b = 10.6663 (12) Å

  • c = 16.505 (2) Å

  • [alpha] = 86.454 (7)°

  • [beta] = 83.424 (8)°

  • [gamma] = 89.376 (7)°

  • V = 922.5 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.41 × 0.32 × 0.21 mm

Data collection
  • Bruker X8 APEXII area-detector diffractometer

  • 19211 measured reflections

  • 3384 independent reflections

  • 2405 reflections with I > 2[sigma](I)

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.145

  • S = 1.04

  • 3384 reflections

  • 263 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.61 e Å-3

  • [Delta][rho]min = -0.38 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C12-C17 ring

D-H...A D-H H...A D...A D-H...A
C9-H9A...O2i 0.97 2.72 3.523 (3) 141
C13-H13...O2i 0.93 2.67 3.375 (3) 133
C21-H21B...O3ii 0.96 2.67 3.261 (4) 121
C11-H11A...O1iii 0.97 2.68 3.201 (3) 114
C5-H5...Cg1iv 0.93 2.91 3.750 (3) 151
Symmetry codes: (i) x+1, y, z; (ii) -x-1, -y+1, -z+1; (iii) -x+1, -y+1, -z; (iv) -x, -y, -z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. 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, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); 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: SJ5310 ).


Acknowledgements

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

References

Bai, Y., Lu, J., Shi, Z. & Yang, B. (2001). Synlett, 12, 544-546.
Belaziz, D., Kandri Rodi, Y., Ouazzani Chahdi, F., Essassi, E. M., Saadi, M. & El Ammari, L. (2013). Acta Cryst. E69, o122.  [CSD] [CrossRef] [details]
Bouwman, E., Driessen, W. L. & Reedjik, J. (1990). Coord. Chem. Rev. 104, 143-172.  [CrossRef] [ChemPort] [ISI]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gravatt, G. L., Baguley, B. C., Wilson, W. R. & Denny, W. A. (1994). J. Med. Chem. 37, 4338-4345.  [CrossRef] [ChemPort] [PubMed] [ISI]
Hasegawa, E., Yoneoka, A., Suzuki, K., Kato, T., Kitazume, T. & Yangi, K. (1999). Tetrahedron, 55, 12957-12968.  [ISI] [CrossRef] [ChemPort]
Horton, D. A., Bourne, G. T. & Smythe, M. L. (2003). Chem. Rev. 103, 893-930.  [ISI] [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] [ISI]
Roth, T., Morningstar, M. L., Boyer, P. L., Hughes, S. H., Buckheit, R. W. & Michejda, C. J. (1997). J. Med. Chem. 40, 4199-4207.  [ISI] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spasov, A. A., Yozhitsa, I. N., Bugaeva, L. I. & Anisimova, V. A. (1999). Pharm. Chem. J. 33, 232-243.  [CrossRef] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [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]


Acta Cryst (2013). E69, o641-o642   [ doi:10.1107/S1600536813008325 ]

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