7-Fluoro-6-nitroquinazolin-4(3H)-one

The quinazolinone unit of the title compound, C8H4FN3O3, is essentially planar, with a maximum deviation of 0.0538 (14) Å for the O atom. The nitro group is twisted by 12.0 (3)° from the mean plane of the quinazolinone ring system. The crystal structure is stabilized by intermolecular N—H⋯O, C—H⋯N and C—H⋯O hydrogen bonds.


Related literature
The title compound is used as an intermediate for the production of several multi-targeted Raf kinase inhibitors, such as 4(3H)-quinazolinone and its derivatives, see: Bridges et al. (1996); Kim et al. (2008). For the antitumor activities of quinolines, see: Labuda et al. (2009). For synthetic aspects, see: Rewcastle et al. (1996). For bond-length data, see: Allen et al. (1987).

Structure Reports Online
As part of our studies on the synthesis of 4(3H)-quinazolinone and its derivatives, the title compound, (I), which is used as the key intermediate , has been synthesized in our laboratory. We report herein the crystal structure of the title compound.
The molecule of the title compound is planar (Fig. 1). The quinazolinone moiety is essentially planar with maximum deviation for for any atoms being 0.0538 (14) for O1. The nitro group is twisted from the mean-plane of the quinazolinone ring by 12.0 (3)°. The bond lengths and angles in (I) are within normal ranges (Allen et al., 1987). The crtstal structure of (I) is stabilized by classical and non-classical intermolecular hydrogen bonds of the types N-H···O, C-H···N and C-H···O; details have been provided in Table 1 and presented as a packing diagram in Fig. 2.

Experimental
The title compound, was prepared by following a reported procedure . 7-Fluoroquinazolin-4(3H)-one (47.4 g, 0.29 mmol) was added to a mixture of concentrated H 2 SO 4 (100 ml) and fuming HNO 3 (100 ml), and heated at 373 K for 1 h. The crude product, 7-fluoro-6-nitroquinazolin-4(3H)-one, was obtained by pouring the reacting mixture onto ice-water (1500 ml). The crystals of (I) suitable for X-ray diffraction studies were obtained by recrystallization from acetic acid.

Refinement
H atoms were positioned geometrically at distances N-H = 0.86 Å and C-H = 0.93 Å and constrained to ride on their parent atoms, with U iso (H) = 1.2 times U eq (parent atoms). Fig. 1. The molecular structure of the titlecompound with the atom numbering scheme. Displacement ellipsoids are drawn at 30% probability levels.