4-[(7-Fluoro­quinazolin-4-yl)­oxy]aniline

Jia, J.; Wang, G.; Lu, D.

doi:10.1107/S1600536810053286

Volume 67
Part 1
Page o229
January 2011

Received 18 October 2010
Accepted 19 December 2010
Online 24 December 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.045
wR = 0.110
Data-to-parameter ratio = 7.3
Details

4-[(7-Fluoroquinazolin-4-yl)oxy]aniline

Jing Jia,^a,^b Guibin Wang ^c and Dingqiang Lu ^a,^b ^*

^aSchool of Pharmaceutical Sciences, Nanjing University of Technology, No. 5 Xinmofan Road, Nanjing 210009, People's Republic of China,^bJiangsu Provincial Institute of Materia Medica, Nanjing University of Technology, No. 26 Majia Street, Nanjing 210009, People's Republic of China, and ^cPRC DAYAOWAN Administration for Entry & Exit Inspection and Quarantine, Haiqingdao Foreign Area Development Zone, Dalian 116610, Liaoning Province, People's Republic of China
Correspondence e-mail: jiajing.jj@gmail.com

In the molecule of the title compound, C₁₄H₁₀FN₃O, the bicyclic quinazoline system is effectively planar, with a mean deviation from planarity of 0.0140 (3) Å. The quinazoline heterocyclic system and the adjacent benzene ring make a dihedral angle of 85.73 (9)°. Two intermolecular N-HN hydrogen bonds contribute to the stability of the crystal structure. In addition, a weak [pi] - [pi] stacking interaction [centroid-centroid distance = 3.902 (2) Å] is observed.

Related literature

For general background to quinazolines, see: Labuda et al. (2009). Graves et al. (2002); For the preparation of the title compound, see: Zhang et al. (2010). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₄H₁₀FN₃O
M_r = 255.25
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.0210 (16) Å
b = 8.3370 (17) Å
c = 17.562 (4) Å
V = 1174.4 (4) Å³
Z = 4
Mo K radiation
= 0.11 mm^-1
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.969, T_max = 0.990
2351 measured reflections
1256 independent reflections
883 reflections with I > 2(I)
R_int = 0.082
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.110
S = 1.02
1256 reflections
172 parameters
H-atom parameters constrained
_max = 0.12 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AN2ⁱ	0.89	2.67	3.408 (4)	142
N1-H1BN3ⁱⁱ	0.89	2.38	3.205 (4)	154
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y-{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+{\script{1\over 2}}, -y, z-{\script{1\over 2}}]$ .

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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: SHELXL97 and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2317 ).

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for the data collection.

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.
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Graves, P. R., Kwiek, J. J., Fadden, P., Ray, R., Hardeman, K., Coley, A. M., Foley, M. & Haystead, T. A. J. (2002). Mol. Pharmacol. 62, 1364-1372.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Labuda, J., Ovadekova, R. & Galandova, J. (2009). Mikrochim. Acta, 164, 371-377.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Zhang, A. H., Yuan, S. T., Shen, Y. P., Wu, Y. D. & Ji, A. C. (2010). CN Patent Appl. CN101671301.

organic compounds