Crystal structures of 4-chloro-phenyl N-(3,5-di-nitro-phen-yl)carbamate and phenyl N-(3,5-di-nitro-phen-yl)carbamate.
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, mol-ecules are linked via N-H⋯O hydrogen bonds, forming chains propagating along [010]. In (I), C-H⋯O hydrogen bonds also link mol-ecules within the chains. The crystal packing in (I) also features a very weak π-π inter-action [centroid-centroid distance = 3.7519 (9) Å].
Department of Physics, Presidency College (Autonomous), Chennai 600 005, India.
Rajamani
R
Raja
Department of Polymer Science, University of Madras, Guindy campus, Chennai 602 025, India.
Subramaniyan
S
Sathiyaraj
Department of Polymer Science, University of Madras, Guindy campus, Chennai 602 025, India.
B Mohamad
BM
Ali
Department of Polymer Science, University of Madras, Guindy campus, Chennai 602 025, India.
A Sultan
AS
Nasar
3,5-di­nitro­phenyl­carbamate; carbamate; crystal structure; hydrogen bonding