Suppression of Disorder in Benzamide and Thiobenzamide Crystals by Fluorine Substitution

Shtukenberg, Alexander G.; Braun, Doris E.; Tan, Melissa; Fellah, Noalle; Kahr, Bart

doi:10.1021/acs.cgd.4c00517

Suppression of Disorder in Benzamide and Thiobenzamide Crystals by Fluorine Substitution

Journal Article · Mon Jun 10 00:00:00 EDT 2024 · Crystal Growth and Design

DOI:https://doi.org/10.1021/acs.cgd.4c00517· OSTI ID:2470191

^[1]; ^[2]; Tan, Melissa ^[1]; Fellah, Noalle ^[1]; ^[1]

New York Univ. (NYU), NY (United States)
Univ. of Innsbruck (Austria)

Disorder is a common feature of molecular crystals that complicates determination of structures and can potentially affect electric and mechanical properties. Suppression of disorder is observed in otherwise severely disordered benzamide and thiobenzamide crystals by substituting hydrogen with fluorine in the ortho-position of the phenyl ring. Fluorine occupancies of 20–30% are sufficient to suppress disorder without changing the packing motif. Crystal structure prediction calculations reveal a much denser lattice energy landscape for benzamide compared to 2-fluorobenzamide, suggesting that fluorine substitution makes disorder less likely.

View Accepted Manuscript (DOE)

Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF)

Grant/Contract Number:: AC02-06CH11357

OSTI ID:: 2470191

Journal Information:: Crystal Growth and Design, Journal Name: Crystal Growth and Design Journal Issue: 12 Vol. 24; ISSN 1528-7483

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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CCDC 2339530: Experimental Crystal Structure Determination G., Shtukenberg, Alexander; E., Braun, Doris; Melissa, Tan, https://doi.org/10.5517/ccdc.csd.cc2jjgq8 The current record is supplemented by this dataset	dataset	January 2024
CCDC 2339531: Experimental Crystal Structure Determination G., Shtukenberg, Alexander; E., Braun, Doris; Melissa, Tan, https://doi.org/10.5517/ccdc.csd.cc2jjgr9 The current record is supplemented by this dataset	dataset	January 2024
CCDC 2339532: Experimental Crystal Structure Determination G., Shtukenberg, Alexander; E., Braun, Doris; Melissa, Tan, https://doi.org/10.5517/ccdc.csd.cc2jjgsb The current record is supplemented by this dataset	dataset	January 2024
CCDC 2339533: Experimental Crystal Structure Determination G., Shtukenberg, Alexander; E., Braun, Doris; Melissa, Tan, https://doi.org/10.5517/ccdc.csd.cc2jjgtc The current record is supplemented by this dataset	dataset	January 2024
CCDC 2339534: Experimental Crystal Structure Determination G., Shtukenberg, Alexander; E., Braun, Doris; Melissa, Tan, https://doi.org/10.5517/ccdc.csd.cc2jjgvd The current record is supplemented by this dataset	dataset	January 2024
CCDC 2339535: Experimental Crystal Structure Determination G., Shtukenberg, Alexander; E., Braun, Doris; Melissa, Tan, https://doi.org/10.5517/ccdc.csd.cc2jjgwf The current record is supplemented by this dataset	dataset	January 2024
CCDC 2339536: Experimental Crystal Structure Determination G., Shtukenberg, Alexander; E., Braun, Doris; Melissa, Tan, https://doi.org/10.5517/ccdc.csd.cc2jjgxg The current record is supplemented by this dataset	dataset	January 2024

Suppression of Disorder in Benzamide and Thiobenzamide Crystals by Fluorine Substitution

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