Phenyl N-(5-chloro-2-nitrophenyl)carbamate

In the title compound, C13H9ClN2O4, the dihedral angle between the benzene rings is 79.5 (1)°. The mean plane of the carbamate group makes angles of 7.4 (2) and 73.6 (2)° with the mean planes of the two benzene rings. In the crystal, weak C—H⋯O interactions are observed between the molecules, connecting them into a two-dimensional network.


Related literature
For details of dovitinib, of which the title compound is a derivative, see: Huynh (2010). For the synthesis of the title compound, see: Bandgar et al. (2011). For bond lengths, see: Zhu et al. (2007).

Comment
The title compound, C 13 H 9 ClN 2 O 4 , (I), is an important derivative of Dovitinib (Huynh, 2010). We report herein its crystal structure.
Experimental 5-chloro-2-nitroaniline (10.46 mmol, 1.80 g) and Et3N (1.5 ml) were dissolved in dichloromethane (30 ml). Phenyl carbonochloridate (19.23 mmol, 3.01 g) was added to the solution and the reaction mixture stired at room temperature for 5 h. The solution was washed with water (15 ml) for 3 times, dried and concentrated to get the crude. The crude was purified by ethanol to get the title compound (1.83 g) (Bandgar et al. 2011). pure: yellow solid. Crystals of the title compound for X-ray diffraction were obtained by slow evaporation of an ethanol solution.

Refinement
H atoms were positioned geometrically with C-H = 0.93 and N-H = 0.86 for aromatic and amine, respectively, and constrained to ride on their parent atoms, with U iso (H) = 1.2 times U eq (C).

Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.