Synthesis, crystal structure and Hirshfeld surface analysis of Schiff base Bis ((1-chlorophenyl) methylene) carbonohydrazide
Abstract
A organic Schiff base, bis((1-chlorophenyl)methylene)carbohydrazide, was synthesized by condensation of carbohydrazide with 2-chlorobenzaldehyde. After slow evaporation for one week, colorless crystals suitable for X-ray diffraction analysis were obtained. producing crystals suitable for X-ray diffraction analysis. The compound crystallizes in the monoclinic system with space group P 2₁/c and has a non-planar conformation due to ortho-chlorinated aromatic rings, which induce significant torsion angles. Hirshfeld surface and contact enrichment analysis reveal that O...H-N hydrogen bonds are the most abundant and dominant intermolecular interactions, while hydrophobic and hydrophilic contacts are clearly separated in the crystal stacking. The crystal structure is stabilized by a combination of strong hydrogen bonds (particularly O...H-N), van der Waals forces, and specific halogen interactions (Cl...π, C–H...Cl). These structural characteristics suggest that the synthesized Schiff base could serve as an effective chelating agent, with its stability and interaction profile showing promise for applications in coordination chemistry and materials science. Electrostatic complementarity shows that the Cl1B…H4A interaction (Cl1B…H4A distance = 2.828 Å) also appears as two inverted images in Fig. 5c. The angle C1B–Cl1B…H4A = 164.4° is close to 180°, but is not optimal, as the electropositive region of the sigma hole of the chlorine atom faces the hydrogen atom, which is also electropositive.
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BibTeX
@misc{jelsch2026synthesis,
title = {{Synthesis, crystal structure and Hirshfeld surface analysis of Schiff base Bis ((1-chlorophenyl) methylene) carbonohydrazide}},
author = {Christian Jelsch and Abdoulaye Diatta and Mbaye Diagne Mbaye and Ibrahima Goudiaby and Insa Badiane and Emmanuel Wenger and Magatte Camara},
howpublished = {HAL},
year = {2026},
month = jul,
doi = {10.21203/rs.3.rs-10418370/v1},
url = {https://hal.science/hal-05850235v1},
note = {CC BY 4.0},
}
RIS
TY - UNPB
TI - Synthesis, crystal structure and Hirshfeld surface analysis of Schiff base Bis ((1-chlorophenyl) methylene) carbonohydrazide
AU - Christian Jelsch
AU - Abdoulaye Diatta
AU - Mbaye Diagne Mbaye
AU - Ibrahima Goudiaby
AU - Insa Badiane
AU - Emmanuel Wenger
AU - Magatte Camara
PY - 2026
DA - 2026/07/21
PB - HAL
DO - 10.21203/rs.3.rs-10418370/v1
UR - https://hal.science/hal-05850235v1
AB - A organic Schiff base, bis((1-chlorophenyl)methylene)carbohydrazide, was synthesized by condensation of carbohydrazide with 2-chlorobenzaldehyde. After slow evaporation for one week, colorless crystals suitable for X-ray diffraction analysis were obtained. producing crystals suitable for X-ray diffraction analysis. The compound crystallizes in the monoclinic system with space group P 2₁/c and has a non-planar conformation due to ortho-chlorinated aromatic rings, which induce significant torsion angles. Hirshfeld surface and contact enrichment analysis reveal that O...H-N hydrogen bonds are the most abundant and dominant intermolecular interactions, while hydrophobic and hydrophilic contacts are clearly separated in the crystal stacking. The crystal structure is stabilized by a combination of strong hydrogen bonds (particularly O...H-N), van der Waals forces, and specific halogen interactions (Cl...π, C–H...Cl). These structural characteristics suggest that the synthesized Schiff base could serve as an effective chelating agent, with its stability and interaction profile showing promise for applications in coordination chemistry and materials science. Electrostatic complementarity shows that the Cl1B…H4A interaction (Cl1B…H4A distance = 2.828 Å) also appears as two inverted images in Fig. 5c. The angle C1B–Cl1B…H4A = 164.4° is close to 180°, but is not optimal, as the electropositive region of the sigma hole of the chlorine atom faces the hydrogen atom, which is also electropositive.
ER -