Crystal structures of 4-chlorophenyl N-(3,5-dinitrophenyl)carbamate and phenyl N-(3,5-dinitrophenyl)carbamate

Abstract

The title compounds, C13H8ClN3O6, (I), and C13H9N3O6, (II), differ in the orientation of the two aromatic rings. In (I), they are essentially coplanar, making a dihedral angle of 8.2 (1)°, while in (II), they are inclined to one another by 76.2 (1)°. The two nitro groups are essentially coplanar with the attached benzene rings, as indicated by the dihedral angles of 1.4 (2) and 2.3 (2)° in (I), and 4.96 (18) and 5.4 (2)° in (II). The carbamate group is twisted slightly from the attached benzene ring, with a C—N—C—O torsion angle of −170.17 (15)° for (I) and 168.91 (13)° for (II). In the crystals of of both compounds, molecules are linked via N—H...O hydrogen bonds, forming chains propagating along [010]. In (I), C—H...O hydrogen bonds also link molecules within the chains. The crystal packing in (I) also features a very weak π–π interaction [centroid–centroid distance = 3.7519 (9) Å].

Keywords

• crystal structure
• carbamate
• 3,5-dinitrophenylcarbamate
• hydrogen bonding