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4-Nitro-N'-[(E)-3-pyridylmethyl-idene]benzohydrazide.

Tanveer Ahmad, Muhammad Zia-Ur-Rehman, Hamid Latif Siddiqui

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This study details the molecular structure of C(13)H(10)N(4)O(3), revealing a planar methyl-idene-hydrazide core. Crystal analysis shows hydrogen bonds forming molecular chains, with disordered nitro groups impacting structure.

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Area of Science:

Crystallography
Organic Chemistry
Molecular Structure Analysis

Background:

Understanding the precise three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
The methyl-idene-hydrazide moiety is a key functional group found in various biologically active compounds and materials.

Purpose of the Study:

To elucidate the detailed molecular and crystal structure of the compound C(13)H(10)N(4)O(3).
To investigate the intermolecular interactions and packing arrangements within the crystal lattice.
To characterize the planarity of the methyl-idene-hydrazide fragment and its orientation relative to aromatic rings.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the atomic coordinates and bond parameters.
Analysis of dihedral angles was performed to assess the relative orientation of the ring systems and the central fragment.
Identification and analysis of intermolecular interactions, including hydrogen bonding and weaker C-H···O interactions.

Main Results:

The methyl-idene-hydrazide fragment [-C(=O)-N-N=C-] was found to be essentially planar (max deviation 0.0228 Å).
Dihedral angles between the methyl-idene-hydrazide plane and the benzene/pyridine rings were 25.44° and 5.47°, respectively.
Intermolecular N-H⋯N hydrogen bonds formed chains along the b axis, with additional stabilization from C-H⋯O interactions. The nitro group oxygen atoms exhibited disorder.

Conclusions:

The crystal structure of C(13)H(10)N(4)O(3) is stabilized by a network of hydrogen bonds, leading to a specific chain-like arrangement.
The observed planarity of the core fragment and the relative orientations of the rings provide insights into the electronic and steric factors governing the molecule's conformation.
The disorder in the nitro group suggests conformational flexibility or specific packing forces influencing its orientation.