ACS Publications. Most Trusted. Most Cited. Most Read
On the Influence of Solvent Properties on the Structural Characteristics of Molecular Crystal Polymorphs

OR SEARCH CITATIONS

My Activity
Publications

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:Crystal Growth & Design 2020, 20, 11, 7152-7162
    Article

    On the Influence of Solvent Properties on the Structural Characteristics of Molecular Crystal Polymorphs
    Click to copy article linkArticle link copied!

    Other Access OptionsSupporting Information (2)

    Crystal Growth & Design

    Cite this: Cryst. Growth Des. 2020, 20, 11, 7152–7162
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.cgd.0c00753
    Published September 17, 2020
    Copyright © 2020 American Chemical Society
    Request reuse permissions

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    A set of structures of homomolecular organic crystals with information on the solvent utilized for crystallization was extracted from the Cambridge Structural Database in order to identify possible general relationships between changes in the crystal structure characteristics of polymorphs and changes in the properties of solvents from which they were crystallized. Feature descriptions of crystal structures and solvents were introduced, which are based on various types of numerical descriptors reflecting different aspects of crystal structures (molecular packing characteristics, lattice energy) and solvent properties (polarity, acid–base behavior, bulk characteristics, etc.). A statistical analysis of the studied set of compounds revealed that the crystal structures of polymorphs obtained from different solvents tend to differ slightly more from each other than the crystal structures of polymorphs crystallized from the same solvent, though these differences in crystal structure properties are not statistically significant. By analyzing the subset of polymorphs obtained from different solvents, we have discovered positive correlations between changes in the tightness of molecular packing and the solvent’s descriptors related to polarity (Spearman’s correlation coefficients ρ = 0.28–0.33). Notably, the more similar the molecular conformations in crystals of polymorphs and the more polar the compound, the more pronounced are the identified correlations (moderate correlations with ρ = 0.5–0.6). At the same time, the expected correlations between changes in the conformation-related properties of a molecule in a crystal and changes in the solvent properties were not found.

    Copyright © 2020 American Chemical Society

    Subjects

    what are subjects

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    Supporting Information

    Click to copy section linkSection link copied!

    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.cgd.0c00753.

    • Spreadsheet tables containing a list of 7987 homomolecular organic polymorphs extracted from the CSD, mapping of solvent names from the CSD, data on crystal structures in SSP and DSP subsets, descriptors of crystal molecules and solvents, specification of molecular descriptors, crystal descriptor difference values for polymorph pairs in the SSP subset and DSP subset, crystal and solvent descriptor difference values in the DSP subset, and crystal molecule and solvent descriptor difference values in the DSP subset (XLSX)

    • Heatmap of the distance matrix for solvents in 62-dimensional feature space, histograms and bar plots of crystal descriptor differences in SSP and DSP subsets, combined histograms and kernel density estimates of descriptors characterizing molecules in SSP and DSP subsets, the difference, number of polymorph pairs, and magnitude of Spearman’s correlation coefficients demonstrated for each pair of crystal and solvent descriptor, depending on a maximum RMSD between crystal molecules in the polymorph pair, Spearman’s correlation coefficients demonstrated for pairs of crystal and solvent descriptor difference values in Figure 3, depending on the polarity of compounds in polymorph pairs, characteristics of crystal descriptor difference distributions in SSP and DSP subsets, characteristics of crystal descriptor difference distributions in 21 compounds common to SSP and DSP subsets, pairs of crystal and solvent descriptor difference pairs showing the lowest p values of correlation coefficients in a set of nonconformational polymorphs (PDF)

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!
    Citation Statements
    Explore this article's citation statements on scite.ai
    powered by  Scite

    This article is cited by 11 publications.

    1. Subhajit Saha, Elena V. Murashova, Vladimir V. Chernyshev, Kumar Biradha. Halogen and Hydrogen Bonding Interplay Triggered Reversible Phase Transformations through Water Release/Uptake: X-ray Powder Diffraction Studies on Halogen-Substituted 1,4-Bis(4,5-diphenyl-imidazolyl)benzene. Crystal Growth & Design 2024, 24 (5) , 2179-2187. https://doi.org/10.1021/acs.cgd.3c01491
    2. Roman A. Eremin, Innokentiy S. Humonen, Pavel N. Zolotarev, Inna V. Medrish, Leonid E. Zhukov, Semen A. Budennyy. Hybrid DFT/Data-Driven Approach for Searching for New Quasicrystal Approximants in Sc-X (X = Rh, Pd, Ir, Pt) Systems. Crystal Growth & Design 2022, 22 (7) , 4570-4581. https://doi.org/10.1021/acs.cgd.2c00463
    3. Jason C. Cole, Paul R. Raithby, Robin Taylor. Prior Likelihoods and Space-Group Preferences of Solvates. Crystal Growth & Design 2021, 21 (2) , 1178-1189. https://doi.org/10.1021/acs.cgd.0c01490
    4. V. E. Kireev, A. M. Banaru, V. A. Bataev, D. S. Kononovich, A. Z. Voskoboynikov, S. M. Aksenov. Crystal Structure and Topological Features of Two New Indene Derivatives. Journal of Structural Chemistry 2024, 65 (10) , 2029-2040. https://doi.org/10.1134/S0022476624100135
    5. Lotfi Derdour, John L. Woodard, Grazyna Graczyk-Millbrandt, Kevin P. Leach. An NMR-based approach for the design of crystallization processes for rigid molecules and effects of molecular rigidity and impurities on crystallization pathways. Chemical Engineering Science 2024, 285 , 119604. https://doi.org/10.1016/j.ces.2023.119604
    6. Roman A. Eremin, Innokentiy S. Humonen, Alexey A. Kazakov, Vladimir D. Lazarev, Anatoly P. Pushkarev, Semen A. Budennyy. Graph neural networks for predicting structural stability of Cd- and Zn-doped γ -CsPbI3. Computational Materials Science 2024, 232 , 112672. https://doi.org/10.1016/j.commatsci.2023.112672
    7. Miao Luo, Juan Zhao, Yanyan Liu, Zhu Mao, Sheng Wang, Zhenguo Chi. All‐Visible‐Light Triggered Photoswitch of Dithienylethene Derivatives with Molecular Conformation Changes Excess 5 Å. Advanced Functional Materials 2023, 33 (9) https://doi.org/10.1002/adfm.202211009
    8. Yan Wang, Defu Sun, Fan Meng, Yangyang Dang, Chuanying Shen, Duanliang Wang. The synthesis, structures, high thermal stability and photoluminescence of two new crown ether clathrates. Inorganica Chimica Acta 2022, 535 , 120842. https://doi.org/10.1016/j.ica.2022.120842
    9. Sotaro Kusumoto, Ryo Suzuki, Masaru Tachibana, Yoshihiro Sekine, Yang Kim, Shinya Hayami. Recrystallization solvent-dependent elastic/plastic flexibility of an n -dodecyl-substituted tetrachlorophthalimide. Chemical Communications 2022, 58 (35) , 5411-5414. https://doi.org/10.1039/D2CC00663D
    10. Guijun Zhu, Jianxin Chen, Jian Han, Jihui Li, Yupeng Li, Kaili Liu. Preparation, Characterization, and Desolvation of 5‐Sulfoisophthalic Acid Sodium Salt Solvates. Chemical Engineering & Technology 2022, 45 (4) , 678-686. https://doi.org/10.1002/ceat.202100576
    11. Valentina A. Karnoukhova, Vladimir V. Baranov, Anna V. Vologzhanina, Angelina N. Kravchenko, Ivan V. Fedyanin. Self-organization of 1,6-dialkyl-3a,6a-diphenylglycolurils in the crystalline state. CrystEngComm 2021, 23 (24) , 4312-4319. https://doi.org/10.1039/D1CE00434D
    Download PDF
    Go to Crystal Growth & Design
    Get e-Alerts
    Get e-Alerts

    Crystal Growth & Design

    Cite this: Cryst. Growth Des. 2020, 20, 11, 7152–7162
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.cgd.0c00753
    Published September 17, 2020
    Copyright © 2020 American Chemical Society
    Request reuse permissions

    Article Views

    1055

    Altmetric

    -

    Citations

    11
    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.