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Volume 68 
Part 11 
Page o3166  
November 2012  

Received 1 October 2012
Accepted 12 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.033
wR = 0.081
Data-to-parameter ratio = 10.0
Details
Open access

3-{[1-(2,3,5-Tri-O-benzoyl-[beta]-D-ribofuranos-1-yl)-1H-1,2,3-triazol-4-yl]methyl}quinazolin-4(3H)-one

aLaboratoire de Chimie Bio-organique et Macromoléculaire, Faculté des Sciences et Techniques Guéliz, Marrakech, Morocco,bLaboratoire de la Matière Condensée et des Nanostructures, Faculté des Sciences et Techniques Guéliz, Marrakech, Morocco, and cLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
Correspondence e-mail: m_elazhari52@yahoo.com

In the compound, C37H29N5O8, the quinazoline residue forms a dihedral angle of 72.90 (9)° with the triazole ring. The furan ring adopts a twist conformation. In the crystal, the molecules are linked by non-classical C-H...N and C-H...O hydrogen bonds, building an infinite three-dimensional network.

Related literature

For details of the synthesis, see: Ines et al. (2008[Ines, N., Ioannis, K. K., Carole, D., Elizabeth, C., Mauro, I. & Thierry, B. (2008). Tetrahedron Lett. 49, 7033-7036.]); Krim et al. (2009[Krim, J., Sillahi, B., Taourirte, M., Rakib, E. M. & Engels, J. W. (2009). Arkivoc, xiii, 142-152.]); Huisgen (1963[Huisgen, R. (1963). Angew. Chem. Int. Ed. 2, 565-598.]), Wu et al. (2004[Wu, P., Feldman, A. K., Nugent, A. K., Hawker, C. J., Scheel, A., Voit, B., Pyun, J., Frechet, J. M. J., Sharpless, K. B. & Fokin, V. V. (2004). Angew. Chem. Int. Ed. 43, 3928-3932.]). For background to the biological activity of quinazolines, see: Traxler (1998[Traxler, P. M. (1998). Exp. Opin. Ther. Patents, 8, 1599-1625.]); Bridges (2001[Bridges, A. J. (2001). Chem. Rev. 101, 2541-2571.]); Wakeling (2005[Wakeling, A. E. (2005). Handbook of Experimental Pharmacology, Vol. 167, pp. 433-450.]); Diana & Nitz (1993[Diana, G. D. & Nitz, J. J. (1993). Eur. Patent 1, 1-38.]); Chen et al. (2000[Chen, M. D., Lu, S. J., Yuag, G. P., Yang, S. Y. & Du, X. L. (2000). Heterocycl. Commun. 6, 421-426.]); Manfredini et al. (2000[Manfredini, S., Vicentini, C. B., Manfrini, M., Bianchi, N., Rutigliano, C., Mischiati, C. & Gambari, R. (2000). Bioorg. Med. Chem. 8, 2343-2346.]). For conformational analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C37H29N5O8

  • Mr = 671.65

  • Monoclinic, P 21

  • a = 11.2646 (2) Å

  • b = 5.6471 (1) Å

  • c = 25.7507 (4) Å

  • [beta] = 99.595 (1)°

  • V = 1615.15 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.33 × 0.29 × 0.25 mm

Data collection
  • Bruker X8 APEXII diffractometer

  • 26180 measured reflections

  • 4490 independent reflections

  • 3651 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.033

  • wR(F2) = 0.081

  • S = 1.03

  • 4490 reflections

  • 451 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.13 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3...O6i 0.93 2.57 3.483 (3) 168
C13-H13...O6ii 0.98 2.36 3.293 (3) 159
C6-H6...N1iii 0.93 2.62 3.390 (3) 141
Symmetry codes: (i) x+1, y-1, z; (ii) x, y-1, z; (iii) [-x+3, y-{\script{1\over 2}}, -z+2].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). 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,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: BT6845 ).


Acknowledgements

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

References

Bridges, A. J. (2001). Chem. Rev. 101, 2541-2571.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, M. D., Lu, S. J., Yuag, G. P., Yang, S. Y. & Du, X. L. (2000). Heterocycl. Commun. 6, 421-426.  [CrossRef] [ChemPort]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Diana, G. D. & Nitz, J. J. (1993). Eur. Patent 1, 1-38.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Huisgen, R. (1963). Angew. Chem. Int. Ed. 2, 565-598.
Ines, N., Ioannis, K. K., Carole, D., Elizabeth, C., Mauro, I. & Thierry, B. (2008). Tetrahedron Lett. 49, 7033-7036.
Krim, J., Sillahi, B., Taourirte, M., Rakib, E. M. & Engels, J. W. (2009). Arkivoc, xiii, 142-152.
Manfredini, S., Vicentini, C. B., Manfrini, M., Bianchi, N., Rutigliano, C., Mischiati, C. & Gambari, R. (2000). Bioorg. Med. Chem. 8, 2343-2346.  [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]
Traxler, P. M. (1998). Exp. Opin. Ther. Patents, 8, 1599-1625.
Wakeling, A. E. (2005). Handbook of Experimental Pharmacology, Vol. 167, pp. 433-450.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Wu, P., Feldman, A. K., Nugent, A. K., Hawker, C. J., Scheel, A., Voit, B., Pyun, J., Frechet, J. M. J., Sharpless, K. B. & Fokin, V. V. (2004). Angew. Chem. Int. Ed. 43, 3928-3932.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3166  [ doi:10.1107/S1600536812042778 ]

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