Crystal structure and Hirshfeld surface analysis of dimethyl 5-[2-(2,4,6-trioxo-1,3-diazinan-5-yl-idene)hydrazin-1-yl]benzene-1,3-di-carboxyl-ate 0.224-hydrate.

Zeliha Atioğlu,Nazim T Shamilov,Fatali E Huseynov,Mehmet Akkurt,Ajaya Bhattarai,Sevinj R Hajiyeva,Gunay Z Mammadova

doi:10.1107/s2056989021006563

Abstract

In the crystal, the whole mol-ecule of the title compound, C14H12N4O7·0.224H2O, is nearly planar with a maximum deviation from the least-squares plane of 0.352 (1) Å. The mol-ecular conformation is stabilized by an intra-molecular N-H⋯O hydrogen bond, generating an S(6) ring motif. In the crystal, mol-ecules are linked by centrosymmetric pairs of N-H⋯O hydrogen bonds, forming ribbons along the c-axis direction. These ribbons connected by van der Waals contacts, forming sheets parallel to the ac plane. There are also inter-molecular van der Waals contacts and and C-H⋯π inter-actions between the sheets. A Hirshfeld surface analysis indicates that the most prevalent inter-actions are O⋯H/H⋯O (41.2%), H⋯H (19.2%), C⋯H/H⋯C (12.2%) and C⋯O/ O⋯C (8.4%).

Highlights

The molecular conformation is stabilized by an intramolecular N— HÁ Á ÁO hydrogen bond, generating an S(6) ring motif
Molecules are linked by centrosymmetric pairs of N—HÁ Á ÁO hydrogen bonds, forming ribbons along the c-axis direction
A Hirshfeld surface analysis indicates that the most prevalent interactions are OÁ Á ÁH/HÁ Á ÁO (41.2%), HÁ Á ÁH (19.2%), CÁ Á ÁH/HÁ Á ÁC (12.2%) and CÁ Á ÁO/ OÁ Á ÁC (8.4%)

Summary

Chemical context

Arylhydrazones, besides their biological significance (Viswanathan et al, 2019), can be used as precursors in the synthesis of coordination compounds (Gurbanov et al, 2017, 2018a,b; Ma et al, 2017a,b) and as building blocks in the construction of supramolecular structures owing to their hydrogen-bond donor and acceptor capabilities (Mahmoudi et al, 2016, 2017a,b,c, 2018a,b; 2019). Non-covalent interactions such as hydrogen, halogen and chalcogen bonds as well as -interactions or their cooperation are able to contribute to synthesis and catalysis and improve the properties of materials (Gurbanov et al, 2020b; Karmakar et al, 2017; Khalilov et al, 2018a,b; Mac Leod et al, 2012; Shikhaliyev et al, 2019; Shixaliyev et al, 2014). The main skeleton of the hydrazone ligand should be decorated by non-covalent bond donor centre(s).

Structural commentary

Supramolecular features

Hirshfeld surface analysis

Synthesis and crystallization

Findings

Refinement details