ABSTRACT
The title compound, C12H11N3O2, is a second monoclinic polymorph (P21, with Z' = 4) of the previously reported monoclinic (P21/c, with Z' = 2) form [Akhmad Aznan et al. (2010 â¶). Acta Cryst. E66, o2400]. Four independent mol-ecules comprise the asymmetric unit, which have the common features of a syn disposition of the pyridine N atom and the toluene ring, and an intra-molecular amine-nitro N-Hâ¯O hydrogen bond. The differences between mol-ecules relate to the dihedral angles between the rings which range from 2.92â (19) to 26.24â (19)°. The geometry-optimized structure [B3LYP level of theory and 6-311â g+(d,p) basis set] has the same features except that the entire mol-ecule is planar. In the crystal, the three-dimensional architecture is consolidated by a combination of C-Hâ¯O, C-Hâ¯π, nitro-N-Oâ¯π and π-π inter-actions [inter-centroid distances = 3.649â (2)-3.916â (2)â Å].
ABSTRACT
The dihedral angle between the benzene and pyridyl rings in the title compound, C(11)H(8)ClN(3)O(2), is 22.65â (10)°, indicating a twisted mol-ecule. The amine H and nitro O atoms form a donor-acceptor pair for an intra-molecular N-Hâ¯O hydrogen bond so that the nitro group is almost coplanar with the pyridine ring to which it is connected [O-N-C-C torsion angle = 7.4â (3)°]. The pyridine N and Cl atoms are approximately syn. The crystal packing features C-Hâ¯Cl inter-actions that lead to undulating supra-molecular chains along [101]. These are connected into sheets by π-π inter-actions occurring between the benzene rings and between the pyridine rings of translationally related mol-ecules along the b axis [centroid-centroid distances = length of b axis = 3.7157â (2)â Å].
ABSTRACT
Four independent mol-ecules comprise the asymmetric unit of the title co-crystal, C(10)H(9)N(3)·C(7)H(5)NO(4), two for each component. Small conformational differences are noted for the benzoic acid derivatives, notably in the twists of the carb-oxy-lic acid residue out of the plane of the benzene ring to which it is connected [torsion angles = 167.62â (17) and 174.54â (17)°]. In the aniline derivative, the major difference is observed in the dihedral angles formed between the CN(3) and phenyl least-squares planes [1.51â (5) and 6.25â (6)°]. Pairs of mol-ecules associate via O-Hâ¯N and N-Hâ¯O hydrogen bonds leading to eight-membered {â¯HOCOâ¯HNCN} hetero-synthons. The two-mol-ecule aggregates are consolidated in the crystal structure by C-Hâ¯O(nitro) and π-π inter-actions [shortest centroid-centroid distance between benzene rings = 3.6242â (10)â Å].