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

Saad, S.M.; Khan, I.; Perveen, S.; Khan, K.M.; Yousuf, S.

doi:10.1107/S1600536812048878

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 (C-C) = 0.002 Å
R = 0.042
wR = 0.120
Data-to-parameter ratio = 12.5
Details

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

Syed Muhammad Saad,^a Imran Khan,^b Shahnaz Perveen,^b Khalid M. Khan ^a and Sammer Yousuf ^a ^*

^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-HN hydrogen bond. In the crystal, molecules are linked into chains running parallel to the b axis by C-HO 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); Sheng-Li et al. (2005); Kung et al. (1999); Ram et al. (1990); Misra et al. (1981); Hess et al. (1968). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₆H₁₄N₄O₄
M_r = 326.31
Triclinic, $[P \overline 1]$
a = 7.2440 (7) Å
b = 10.2832 (10) Å
c = 11.1622 (11) Å
= 72.475 (2)°
= 83.663 (2)°
= 70.429 (2)°
V = 747.05 (13) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.970, T_max = 0.984
8510 measured reflections
2792 independent reflections
2249 reflections with I > 2(I)
R_int = 0.021

Refinement

R[F² > 2(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
_max = 0.18 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C5-H5AN2	0.93	2.22	2.833 (2)	123
C8-H8AO3ⁱ	0.93	2.60	3.490 (2)	161
Symmetry code: (i) x, y+1, z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2009).

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.
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.
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.
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.
Ram, V. J., Singha, U. K. & Guru, P. Y. (1990). Eur. J. Med. Chem. 25 , 533-538.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
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.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds