4-Nitrophenyl 2-bromo-2-methylpropanoate

In the title compound, C10H10BrNO4, the planes of the carboxylate and nitro groups are rotated by 60.53 (13) and 6.4 (3)°, respectively, to the benzene ring. In the crystal, intermolecular C—H⋯O hydrogen bonds link the molecules into zigzag chains parallel to the c axis.

In the title compound, C 10 H 10 BrNO 4 , the planes of the carboxylate and nitro groups are rotated by 60.53 (13) and 6.4 (3) , respectively, to the benzene ring. In the crystal, intermolecular C-HÁ Á ÁO hydrogen bonds link the molecules into zigzag chains parallel to the c axis.
Financial support from the Universitá Politecnica delle Marche and the Universitá degli Studi di Parma is gratefully acknowledged.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2722).

Comment
The synthesis of the title compound and analogues was originally reported in the early part of last century (Bischoff, 1907), and in the seventies several of these compounds were found to possess useful miticidal, insecticidal, nematocidal or fungicidal activities (Kaeriyama et al., 1976). More recently, the title compound was prepared (Haddleton & Waterson, 1999) and used as initiator for H-atom transfer polymerization. The same compound was also used in the preparation of new alkoxyamines derived from imadaziline-, imidazoline-and pyrrolidine-1-oxyl nitroxides (Edeleva et al., 2009) and, within our group, for the synthesis of phenyl-and 4-nitrophenyl-2-(2,2-diphenyl-3-(phenylimino)-indolin-1-yloxy)-2-methylpropionate (Guillaneuf et al., 2007). In order to obtain structural parameters for molecular mechanics calculations for the above mentioned alkoxyamines, the X-ray crystal structure of the title compound has been determined and the results are reported herein.
In the molecule of the title compound ( Fig. 1), the plane of the nitro group is approximately coplanar with the benzene ring (dihedral angle 6.4 (3) °), whereas the plane of the carboxylic group is tilted by 60.53 (13) °. All bond lengths and angles are unexceptional. In the crystal structure (Fig. 2), the molecules are linked by intermolecular C-H···O hydrogen bonds (Table 1) into zigzag chains running parallel to the c axis.

Refinement
All H atoms were placed in geometrically idealized positions and treated as riding atoms, with C-H = 0.93-0.96 Å, and U iso (H) = 1.2 U eq (C) or 1.5 U eq (C) for methyl H atoms. Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 40% probability level.