2-Eth­oxy-5-methylbis[1,2,4]triazolo[1,5-a:4′,3′-c]quinazoline

Al-Salahi, R.; Geffken, D.; Bari, A.

doi:10.1107/S1600536811052810

Volume 68
Part 1
Page o101
January 2012

Received 1 November 2011
Accepted 7 December 2011
Online 14 December 2011

Key indicators
Single-crystal X-ray study
T = 153 K
Mean (C-C) = 0.003 Å
R = 0.055
wR = 0.134
Data-to-parameter ratio = 15.6
Details

2-Ethoxy-5-methylbis[1,2,4]triazolo[1,5-a:4',3'-c]quinazoline

Rashad Al-Salahi,^a ^* Detlef Geffken ^b and Ahmed Bari ^a

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, and ^bDepartment of Chemistry, Institute of Pharmacy, University of Hamburg, Bundesstrasse 45, 20146, Hamburg, Germany
Correspondence e-mail: abari@ksu.edu.sa

The title compound, C₁₃H₁₂N₆O, is a functionalized ditriazoloquinazoline with substituted ethoxy and methyl groups attached at the 2-position of each triazole spacer. The fused-ring system is essentially planar [r.m.s. deviation = 0.016 (2) Å]. In the crystal, a weak C-HN hydrogen bond connects the molecules into a chain along [101].

Related literature

For the biological activity of quinazoline derviatives, see: Alagarsamy et al. (2005, 2007). For our study of the chemical and pharmacological properties of triazolo quinazoline derivatives, see: Al-Salahi (2009); Al-Salahi et al. (2010, 2011); Berezank et al. (2008a,b). For related structures, see: El-Tombary et al. (1999).

Experimental

Crystal data

C₁₃H₁₂N₆O
M_r = 268.29
Monoclinic, P 2₁ /c
a = 7.4121 (11) Å
b = 19.240 (3) Å
c = 9.3096 (14) Å
= 109.051 (2)°
V = 1254.9 (3) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 153 K
0.43 × 0.21 × 0.05 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998) T_min = 0.959, T_max = 0.995
2851 measured reflections
2851 independent reflections
1817 reflections with I > 2(I)
R_int = 0.053

Refinement

R[F² > 2(F²)] = 0.055
wR(F²) = 0.134
S = 0.91
2851 reflections
183 parameters
H-atom parameters constrained
_max = 0.29 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3N4ⁱ	0.95	2.60	3.533 (2)	166
Symmetry code: (i) x-1, y, z-1.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5002 ).

Acknowledgements

We wish to express our gratitude to the Department of Chemistry, X-ray crystallography division of Hamburg University for their valuable help in the determination of the X-ray crystal structure.

References

Alagarsamy, V., Giridhar, R. & Yadav, M. R. (2005). Bioorg. Med. Chem. Lett. 15, 1877-1880.
Alagarsamy, V., Solomon, V. R. & Murugan, M. (2007). Bioorg. Med. Chem. 15, 4009-4015.
Al-Salahi, R. (2009). PhD dissertation, Hamburg University, Germany.
Al-Salahi, R. & Geffken, D. (2010). Molecules, 15, 7016-7034.
Al-Salahi, R., Geffken, D. & Koellner, M. (2011). Chem. Pharm. Bull. 59, 730-733.
Berezank, J. F., Chan, D., Geffken, D., Hanagan, M. A., Lepone, G. E., Pasteris, R. S. & Swan, T. (2008a). World patent WO 2008103357.
Berezank, J. F., Chan, D., Geffken, D., Hanagan, M. A., Lepone, G. E., Pasteris, R. S. & Swan, T. (2008b). Chem. Abstr. 1042828.
Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
El-Tombary, A. A., Ismail, K. A., Aboulwafa, O. M., Omar, A.-M., El-Azzouni, M. Z. & El-Mansoury, S. T. (1999). Farmaco, 54, 486-488.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds