RESUMO
The crystal structures and Hirshfeld surface analyses of three similar azo compounds are reported. Methyl 4-{2,2-di-chloro-1-[(E)-phenyl-diazen-yl]ethen-yl}benzoate, C16H12Cl2N2O2, (I), and methyl 4-{2,2-di-chloro-1-[(E)-(4-methyl-phen-yl)diazen-yl]ethen-yl}benzoate, C17H14Cl2N2O2, (II), crystallize in the space group P21/c with Z = 4, and methyl 4-{2,2-di-chloro-1-[(E)-(3,4-di-methyl-phen-yl)diazen-yl]ethen-yl}benzoate, C18H16Cl2N2O2, (III), in the space group P with Z = 2. In the crystal of (I), mol-ecules are linked by C-Hâ¯N hydrogen bonds, forming chains with C(6) motifs parallel to the b axis. Short inter-molecular Clâ¯O contacts of 2.8421â (16)â Å and weak van der Waals inter-actions between these chains stabilize the crystal structure. In (II), mol-ecules are linked by C-Hâ¯O hydrogen bonds and C-Clâ¯π inter-actions, forming layers parallel to (010). Weak van der Waals inter-actions between these layers consolidate the mol-ecular packing. In (III), mol-ecules are linked by C-Hâ¯π and C-Clâ¯π inter-actions forming chains parallel to [011]. Furthermore, these chains are connected by C-Clâ¯π inter-actions parallel to the a axis, forming (01) layers. The stability of the mol-ecular packing is ensured by van der Waals forces between these layers.
RESUMO
A new polymorph of the title compound, C14H8Br3N3O2, (form-2) was obtained in the same manner as the previously reported form-1 [Akkurt et al. (2022 â¸). Acta Cryst. E78, 732-736]. The structure of the new polymorph is stabilized by a C-Hâ¯O hydrogen bond that links mol-ecules into chains. These chains are linked by face-to-face π-π stacking inter-actions, resulting in a layered structure. Short inter-mol-ecular Brâ¯O contacts and van der Waals inter-actions between the layers aid in the cohesion of the crystal packing. In the previously reported form-1, C-Hâ¯Br inter-actions connect mol-ecules into zigzag chains, which are linked by C-Brâ¯π inter-actions into layers, whereas the van der Waals inter-actions between the layers stabilize the crystal packing of form-2. Hirshfeld mol-ecular surface analysis was used to compare the inter-molecular inter-actions of the polymorphs.
RESUMO
In the title compound, C14H8Br2FN3O2, the 4-fluoro-phenyl ring and the nitro-substituted phenyl ring form a dihedral angle of 64.37â (10)°. Mol-ecules in the crystal are connected by C-Hâ¯O and C-Hâ¯F hydrogen bonds into layers parallel to (011). The crystal packing is consolidated by C-Brâ¯π and C-Fâ¯π inter-actions, as well as by π-π stacking inter-actions. According to a Hirshfeld surface analysis of the crystal structure, the most significant contributions to the crystal packing are from Oâ¯H/Hâ¯O (15.0%), Hâ¯H (14.3%), Brâ¯H/Hâ¯Br (14.2%), Câ¯H/Hâ¯C (10.1%), Fâ¯H/Hâ¯F (7.9%), Brâ¯Br (7.2%) and Brâ¯C/Câ¯Br (5.8%) contacts.