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Volume 69 
Part 1 
Page o8  
January 2013  

Received 21 November 2012
Accepted 28 November 2012
Online 5 December 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.002 Å
R = 0.042
wR = 0.120
Data-to-parameter ratio = 12.5
Details
Open access

N-(2,5-Dimethoxyphenyl)-6-nitroquinazolin-4-amine

aH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan, and bPCSIR Labortories Complex, Karachi, Shahrah-e-Dr. Salmuzzaman Siddiqui, Karachi 75280, Pakistan
Correspondence e-mail: dr.sammer.yousuf@gmail.com

In the title molecule, C16H14N4O4, the quinazoline ring is substantially planar (r.m.s. deviation = 0.0129 Å) and forms a dihedral angle of 2.73 (8)° with the benzene ring. The conformation of the molecule is stabilized by an intramolecular C-H...N hydrogen bond. In the crystal, molecules are linked into chains running parallel to the b axis by C-H...O hydrogen bonds. In addition, [pi]-[pi] stacking is observed between dimethoxy-substituted and nitro-substituted benzene rings, with centroid-centroid distances in the range 3.6438 (10)-3.7148 (10) Å.

Related literature

For the biological activity of quinazoline derivatives, see: Arfan et al. (2008[Arfan, M., Khan, R., Imran, M., Khan, H. & Mehmood, J. (2008). J. Chem. Soc. Pak. 30, 299-305.]); Sheng-Li et al. (2005[Sheng-Li, C., Yu-Ping, F., Yu-Yang, J., Shi-Ying, L., Guo-Yu, D. & Run-Tao, L. (2005). Bioorg. Med. Chem. Lett. 15, 1915-1917.]); Kung et al. (1999[Kung, P.-P., Casper, M. D., Cook, K. L., Wilson-Lingardo, L., Risen, L. M., Vickers, T. A., Ranken, R., Blyn, L. B., Wyatt, J. R., Cook, P. D. & Ecker, D. J. (1999). J. Med. Chem. 42, 4705-4713.]); Ram et al. (1990[Ram, V. J., Singha, U. K. & Guru, P. Y. (1990). Eur. J. Med. Chem. 25 , 533-538.]); Misra et al. (1981[Misra, V. S., Singh, C., Agarwal, R. & Choudhary, K. C. (1981). J. Chem. Soc. Pak. 3,, 209-213.]); Hess et al. (1968[Hess, H. J., Cronin, T. H. & Scriabine, A. (1968). J. Med. Chem. 11, 130-136.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C16H14N4O4

  • Mr = 326.31

  • Triclinic, [P \overline 1]

  • a = 7.2440 (7) Å

  • b = 10.2832 (10) Å

  • c = 11.1622 (11) Å

  • [alpha] = 72.475 (2)°

  • [beta] = 83.663 (2)°

  • [gamma] = 70.429 (2)°

  • V = 747.05 (13) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 298 K

  • 0.29 × 0.19 × 0.15 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.970, Tmax = 0.984

  • 8510 measured reflections

  • 2792 independent reflections

  • 2249 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.120

  • S = 1.05

  • 2792 reflections

  • 224 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C5-H5A...N2 0.93 2.22 2.833 (2) 123
C8-H8A...O3i 0.93 2.60 3.490 (2) 161
Symmetry code: (i) x, y+1, z.

Data collection: SMART (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. 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: SHELXTL, PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5029 ).


Acknowledgements

The authors are thankful to the Higher Education Commission (HEC) Pakistan (project No. 20-2073) and the Pakistan Academy of Sciences (PAS) for their financial support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Arfan, M., Khan, R., Imran, M., Khan, H. & Mehmood, J. (2008). J. Chem. Soc. Pak. 30, 299-305.  [ChemPort]
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Hess, H. J., Cronin, T. H. & Scriabine, A. (1968). J. Med. Chem. 11, 130-136.  [CrossRef] [ChemPort] [PubMed] [ISI]
Kung, P.-P., Casper, M. D., Cook, K. L., Wilson-Lingardo, L., Risen, L. M., Vickers, T. A., Ranken, R., Blyn, L. B., Wyatt, J. R., Cook, P. D. & Ecker, D. J. (1999). J. Med. Chem. 42, 4705-4713.  [ISI] [CrossRef] [PubMed] [ChemPort]
Misra, V. S., Singh, C., Agarwal, R. & Choudhary, K. C. (1981). J. Chem. Soc. Pak. 3,, 209-213.
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Ram, V. J., Singha, U. K. & Guru, P. Y. (1990). Eur. J. Med. Chem. 25 , 533-538.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sheng-Li, C., Yu-Ping, F., Yu-Yang, J., Shi-Ying, L., Guo-Yu, D. & Run-Tao, L. (2005). Bioorg. Med. Chem. Lett. 15, 1915-1917.  [PubMed]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o8  [ doi:10.1107/S1600536812048878 ]

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