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

Ouahrouch, A.; Taourirte, M.; El Azhari, M.; Saadi, M.; El Ammari, L.

doi:10.1107/S1600536812042778

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 (C-C) = 0.004 Å
R = 0.033
wR = 0.081
Data-to-parameter ratio = 10.0
Details

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

Abdelaaziz Ouahrouch,^a Moha Taourirte,^a Mohamed El Azhari,^b Mohamed Saadi ^c and Lahcen El Ammari ^c ^*

^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-HN and C-HO hydrogen bonds, building an infinite three-dimensional network.

Related literature

For details of the synthesis, see: Ines et al. (2008); Krim et al. (2009); Huisgen (1963), Wu et al. (2004). For background to the biological activity of quinazolines, see: Traxler (1998); Bridges (2001); Wakeling (2005); Diana & Nitz (1993); Chen et al. (2000); Manfredini et al. (2000). For conformational analysis, see: Cremer & Pople (1975).

Experimental

Crystal data

C₃₇H₂₉N₅O₈
M_r = 671.65
Monoclinic, P 2₁
a = 11.2646 (2) Å
b = 5.6471 (1) Å
c = 25.7507 (4) Å
= 99.595 (1)°
V = 1615.15 (5) Å³
Z = 2
Mo K radiation
= 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(I)
R_int = 0.029

Refinement

R[F² > 2(F²)] = 0.033
wR(F²) = 0.081
S = 1.03
4490 reflections
451 parameters
1 restraint
H-atom parameters constrained
_max = 0.14 e Å^-3
_min = -0.13 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3O6ⁱ	0.93	2.57	3.483 (3)	168
C13-H13O6ⁱⁱ	0.98	2.36	3.293 (3)	159
C6-H6N1ⁱⁱⁱ	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); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia,1997); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

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.
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.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Diana, G. D. & Nitz, J. J. (1993). Eur. Patent 1, 1-38.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
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.
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.

organic compounds