Ethyl 2-(6-nitro-1H-indazol-1-yl)acetate

Abstract

The asymmetric unit of the title compound, C 11 H 11 N 3 O 4 , comprises two independent molecules, both of which display positional disorder of their ethyl chains in 0.868 (4):0.132 (4) and 0.839 (4):0.161 (4) ratios. The packing is directed by a combination of C-HÁ Á ÁO hydrogen bonds and N-OÁ Á Á interactions between nitro groups and the aromatic rings. Structure descriptionAs a continuation of our studies of N-substituted indazole derivatives and their potential pharmacological activities (Boulhaoua et al., 2016;Mohamed Abdelahi et al., 2017), we now describe the synthesis and structure of the title compound.The asymmetric unit comprises two independent molecules differing primarily in the orientations of the ester groups (Fig. 1). The dihedral angle between the five-and sixmembered rings making up the imidazole rings are 1.12 (3) in the molecule containing N1 and N2 and 1.28 (3) in the other. In both molecules, the ethyl groups are approximately 15% disordered.The packing is directed by a combination of C-HÁ Á ÁO hydrogen bonds (Table 1) and N-OÁ Á Á contacts between nitro groups and the six-membered rings of the indazole moieties. Fig. 1 shows the C8-H8AÁ Á ÁO5 hydrogen bond occurring within the asymmetric unit as well as the N3-O3Á Á Á(C12-C17 ring) interaction [OÁ Á Á = 3.131 (1) Å , N-OÁ Á Á = 102.81 (9) ] The second N-OÁ Á Á interaction occurs between N6-O7 and the centroid of the C1-C6 ring at x, y, z + 1 [OÁ Á Á = 3.14 (1) Å , N-OÁ Á Á = 109.16 (9) ]. The combination of hydrogen bonds and N-OÁ Á Á interactions leads to a layer structure parallel to (100) (Figs. 2 and 3).