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

Bao-Hua Zou; Zheng Fang; Hui Zhong; Guo Kai; Ping Wei

doi:10.1107/S1600536812030930

. 2012 Jul 25;68(Pt 8):o2547. doi: 10.1107/S1600536812030930

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

Bao-Hua Zou ^a, Zheng Fang ^a, Hui Zhong ^a, Guo Kai ^b,^*, Ping Wei ^b

PMCID: PMC3414992 PMID: 22904979

Abstract

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 ▶).

Experimental

Crystal data

C₁₃H₉ClN₂O₄
M _r = 292.67
Monoclinic,
a = 8.4760 (17) Å
b = 5.9270 (12) Å
c = 24.996 (5) Å
β = 94.77 (3)°
V = 1251.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.910, T _max = 0.969
2466 measured reflections
2300 independent reflections
1593 reflections with I > 2σ(I)
R _int = 0.084
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.155
S = 1.00
2300 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.22 e Å⁻³

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-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812030930/jj2143sup1.cif

e-68-o2547-sup1.cif^{(21.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030930/jj2143Isup2.hkl

e-68-o2547-Isup2.hkl^{(113.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812030930/jj2143Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O2ⁱ	0.93	2.48	3.312 (4)	150
C13—H13A⋯O1ⁱⁱ	0.93	2.56	3.419 (4)	154

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This research work was financially supported by the School of Pharmaceutical Science, Nanjing University of Technology, and the National Key Basic Research Program of China (973 Program) (grant Nos. 2011CB710803 and 2012CB725204).

supplementary crystallographic information

Comment

The title compound, C₁₃H₉ClN₂O₄, (I), is an important derivative of Dovitinib (Huynh, 2010). We report herein its crystal structure.

In the title compound, C₁₃H₉ClN₂O₄, the dihedral angle between the two benzene rings is 79.5 (1)° (Fig. 1). The angles between the mean plane of the carbamate group (N2/C7/O3/O4) and the two 6-membered benzene rings (C1–C6 and C8–C13) is 7.4° and 73.6°, respectively. Bond lengths are in normal ranges (Zhu et al., 2007). In the crystal structure, weak C—H···O (Table 1 )intermolecular interactions are observed which link the molecules into a two-dimensional network array (Fig. 2).

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.