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Exploring concomitant/conformational dimorphism in a difluoro-substituted phosphoramidate derivative.

Avantika Hasija¹, Deepak Chopra¹

¹Department of Chemistry, Indian Institute of Science Education and Research, Bhopal By-Pass Road, Bhopal, Madhya Pradesh 462 066, India.

Acta Crystallographica. Section C, Structural Chemistry

|April 9, 2019

Summary

Two crystalline forms (dimorphs) of diphenyl (3,4-difluorophenyl)phosphoramidate were discovered through solution-mediated crystallization. Their distinct structures and intermolecular interactions were analyzed, revealing conformational polymorphism.

Keywords:

Z prime conformational polymorph crystal structure energy framework phosphoramidates polymorphism

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Area of Science:

Solid-state chemistry
Crystallography
Materials science

Background:

Polymorphism is common in organic molecules, influencing physical properties.
Understanding crystal packing and intermolecular forces is crucial for materials design.

Purpose of the Study:

To investigate the concomitant occurrence of dimorphs of diphenyl (3,4-difluorophenyl)phosphoramidate.
To characterize the structural and energetic differences between the observed crystal forms.
To classify the observed polymorphism based on molecular conformation.

Main Methods:

Solution-mediated crystallization
Single-crystal X-ray diffraction
Differential scanning calorimetry (DSC)
Powder X-ray diffraction (PXRD)
Energy decomposition analysis (PIXEL method)
Hirshfeld surface analysis

Main Results:

Two distinct crystalline forms (Form I: block, Z'=1; Form II: needle, Z'=2) were identified.
Quantitative analysis revealed N-H...O hydrogen bonds as primary contributors to crystal stability, supplemented by dispersion energy.
Significant variations in torsion angles confirmed the conformational nature of the polymorphism.
Lattice energies showed opposite trends despite similar melting points.

Conclusions:

Diphenyl (3,4-difluorophenyl)phosphoramidate exhibits conformational polymorphism.
Intermolecular interactions, particularly hydrogen bonding and dispersion forces, dictate crystal structure and stability.
The study provides insights into the relationship between molecular conformation, crystal packing, and thermodynamic stability.