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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 [sigma](C-C) = 0.003 Å
R = 0.055
wR = 0.134
Data-to-parameter ratio = 15.6
Details
Open access

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

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-H...N hydrogen bond connects the molecules into a chain along [101].

Related literature

For the biological activity of quinazoline derviatives, see: Alagarsamy et al. (2005[Alagarsamy, V., Giridhar, R. & Yadav, M. R. (2005). Bioorg. Med. Chem. Lett. 15, 1877-1880.], 2007[Alagarsamy, V., Solomon, V. R. & Murugan, M. (2007). Bioorg. Med. Chem. 15, 4009-4015.]). For our study of the chemical and pharmacological properties of triazolo quinazoline derivatives, see: Al-Salahi (2009[Al-Salahi, R. (2009). PhD dissertation, Hamburg University, Germany.]); Al-Salahi et al. (2010[Al-Salahi, R. & Geffken, D. (2010). Molecules, 15, 7016-7034.], 2011[Al-Salahi, R., Geffken, D. & Koellner, M. (2011). Chem. Pharm. Bull. 59, 730-733.]); Berezank et al. (2008a[Berezank, J. F., Chan, D., Geffken, D., Hanagan, M. A., Lepone, G. E., Pasteris, R. S. & Swan, T. (2008a). World patent WO 2008103357.],b[Berezank, J. F., Chan, D., Geffken, D., Hanagan, M. A., Lepone, G. E., Pasteris, R. S. & Swan, T. (2008b). Chem. Abstr. 1042828.]). For related structures, see: El-Tombary et al. (1999[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.]).

[Scheme 1]

Experimental

Crystal data
  • C13H12N6O

  • Mr = 268.29

  • Monoclinic, P 21 /c

  • a = 7.4121 (11) Å

  • b = 19.240 (3) Å

  • c = 9.3096 (14) Å

  • [beta] = 109.051 (2)°

  • V = 1254.9 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.959, Tmax = 0.995

  • 2851 measured reflections

  • 2851 independent reflections

  • 1817 reflections with I > 2[sigma](I)

  • Rint = 0.053

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.134

  • S = 0.91

  • 2851 reflections

  • 183 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3...N4i 0.95 2.60 3.533 (2) 166
Symmetry code: (i) x-1, y, z-1.

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART, 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: 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: 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.  [CrossRef] [PubMed] [ChemPort]
Alagarsamy, V., Solomon, V. R. & Murugan, M. (2007). Bioorg. Med. Chem. 15, 4009-4015.  [CrossRef] [PubMed] [ChemPort]
Al-Salahi, R. (2009). PhD dissertation, Hamburg University, Germany.
Al-Salahi, R. & Geffken, D. (2010). Molecules, 15, 7016-7034.  [ChemPort]
Al-Salahi, R., Geffken, D. & Koellner, M. (2011). Chem. Pharm. Bull. 59, 730-733.  [ChemPort] [PubMed]
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.  [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o101  [ doi:10.1107/S1600536811052810 ]

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