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Title: ROY Revisited, Again: The Eighth Solved Structure

X-ray powder diffraction and crystal structure prediction (CSP) algorithms were used in synergy to establish the crystal structure of the eighth polymorph of 5-methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile (ROY), form R05. R05 crystallizes in the monoclinic space group P2_1 with lattice parameters a = 11.479(4) Å, b = 11.030(1) Å, c = 10.840(6) Å, β = 118.23(1)°. This is both the first acentric ROY polymorph, and the first with Z' > 1. The torsion angles defined by the S-C-N-C atom sequence of each molecule in the asymmetric unit are -34.0° and 44.9°. These angles fall between those previously determined for the red and orange forms of ROY. Hirshfeld surface analysis was employed to understand the crystal packing and intermolecular interactions in R05 and an updated energy stability ranking was determined using computational methods. Finally, although the application of CSP was critical to the structure solution of R05, energy stability rankings determined using a series of DFT vdW-inclusive models substantially deviate from experiment, indicating that ROY polymorphism continues to be a challenge for CSP.
 [1] ;  [1] ;  [2] ;  [3] ;  [4] ;  [5] ;  [1] ;  [6] ;  [2]
  1. New York Univ. (NYU), NY (United States). Dept. of Chemistry and Molecular Design Inst.
  2. Univ. of Nevada, Las Vegas, NV (United States). High Pressure Science and Engineering Center (HiPSEC), and Dept. of Physics and Astronomy
  3. Argonne National Lab. (ANL), Argonne, IL (United States). Advanced Photon Source (APS), X-ray Science Division
  4. Brookhaven National Lab. (BNL), Upton, NY (United States). National Synchrotron Light Source II (NSLS-II), Photon Sciences Division
  5. New York Univ. (NYU), NY (United States). Dept. of Chemistry and Molecular Design Inst.; Harvard Univ., Cambridge, MA (United States). Dept. of Chemistry and Chemical Biology
  6. New York Univ. (NYU), NY (United States). Dept. of Chemistry and Molecular Design Inst.; Waseda Univ., Shinjuku (Japan). Dept. of Advanced Science and Engineering
Publication Date:
Report Number(s):
Journal ID: ISSN 1359-6640; FDISE6
Grant/Contract Number:
SC0012704; NA0001982
Accepted Manuscript
Journal Name:
Faraday Discussions
Additional Journal Information:
Journal Name: Faraday Discussions; Journal ID: ISSN 1359-6640
Royal Society of Chemistry
Research Org:
Brookhaven National Laboratory (BNL), Upton, NY (United States)
Sponsoring Org:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
Country of Publication:
United States
OSTI Identifier:
Alternate Identifier(s):
OSTI ID: 1461212