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On the Influence of Solvent Properties on the Structural Characteristics of Molecular Crystal Polymorphs

Cite this: Cryst. Growth Des. 2020, 20, 11, 7152–7162
Publication Date (Web):September 17, 2020
https://doi.org/10.1021/acs.cgd.0c00753
Copyright © 2020 American Chemical Society

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    Abstract

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    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.

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    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)

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    Cited By

    This article is cited by 10 publications.

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    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
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