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ROY revisited, again: the eighth solved structure.

Melissa Tan1, Alexander G Shtukenberg, Shengcai Zhu

  • 1Department of Chemistry, Molecular Design Institute, New York University, 100 Washington Square East, Room 1001, New York City, NY 10003, USA. bart.kahr@nyu.edu.

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Summary
This summary is machine-generated.

The eighth polymorph of 5-methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile (ROY), form R05, was identified using X-ray diffraction and crystal structure prediction. This novel polymorph is the first acentric form with multiple molecules in its asymmetric unit.

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Area of Science:

  • Crystallography
  • Materials Science
  • Computational Chemistry

Background:

  • Polymorphism in 5-methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile (ROY) presents challenges for materials characterization.
  • Understanding crystal structures is crucial for predicting material properties and applications.

Purpose of the Study:

  • To determine the crystal structure of the eighth polymorph of ROY, designated as form R05.
  • To analyze the crystal packing, intermolecular interactions, and energetic stability of R05.
  • To evaluate the effectiveness of crystal structure prediction (CSP) algorithms in solving complex polymorphs.

Main Methods:

  • X-ray powder diffraction was employed for experimental structure determination.
  • Crystal structure prediction (CSP) algorithms were utilized in synergy with experimental data.
  • Hirshfeld surface analysis was performed to investigate intermolecular interactions.
  • Computational methods, including DFT with van der Waals (vdW)-inclusive models, were used for energy stability ranking.

Main Results:

  • The crystal structure of ROY form R05 was successfully established, crystallizing in the monoclinic space group P21.
  • R05 is the first known acentric polymorph of ROY and the first with more than one molecule in the asymmetric unit (Z' > 1).
  • Torsion angles within the asymmetric unit molecules (R05-1 and R05-2) were quantified and compared to other ROY forms.
  • Hirshfeld surface analysis provided insights into crystal packing and intermolecular forces.
  • Energy stability rankings derived from computational models showed discrepancies with experimental observations.

Conclusions:

  • The crystal structure of the novel ROY polymorph R05 has been elucidated.
  • ROY polymorphism remains a significant challenge for current crystal structure prediction methodologies.
  • Further refinement of computational models is needed to accurately predict energy stabilities of ROY polymorphs.