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Title: Powder diffraction and crystal structure prediction identify four new coumarin polymorphs

Abstract

Coumarin, a simple, commodity chemical isolated from beans in 1820, has, to date, only yielded one solid state structure. Here, we report a rich polymorphism of coumarin grown from the melt. Four new metastable forms were identified and their crystal structures were solved using a combination of computational crystal structure prediction algorithms and X-ray powder diffraction. With five crystal structures, coumarin has become one of the few rigid molecules showing extensive polymorphism at ambient conditions. We demonstrate the crucial role of advanced electronic structure calculations including many-body dispersion effects for accurate ranking of the stability of coumarin polymorphs and the need to account for anharmonic vibrational contributions to their free energy. As such, coumarin is a model system for studying weak intermolecular interactions, crystallization mechanisms, and kinetic effects.

Authors:
ORCiD logo [1]; ORCiD logo [2];  [3]; ORCiD logo [4]; ORCiD logo [5];  [4];  [4];  [6];  [6]; ORCiD logo [5]; ORCiD logo [7]; ORCiD logo [3];  [8]; ORCiD logo [9]
  1. New York Univ. (NYU), NY (United States). Department of Chemistry, Molecular Design Institute
  2. Univ. of Nevada, Las Vegas, NV (United States). Department of Physics and Astronomy, High Pressure Science and Engineering Center; Stony Brook Univ., NY (United States). Department of Geosciences
  3. Curtin University, Perth (Australia). Curtin Institute for Computation and Department of Chemistry
  4. New York Univ. (NYU), NY (United States). Department of Chemistry
  5. Fritz-Haber-Institut der Max-Planck-Gesellschaft, Berlin (Germany); University of Luxembourg (Luxembourg). Physics and Materials Science Research Unit
  6. Technion Israel Institute of Technology, Haifa (Israel). Department of Materials Science and Engineering, Russell Berrie Nanotechnology Institute
  7. Skolkovo Institute of Science and Technology, Skolkovo Innovation Center, Moscow (Russia); Stony Brook Univ., NY (United States). Department of Geosciences
  8. New York Univ. (NYU), NY (United States). Department of Chemistry and Courant Institute of Mathematical Sciences; New York University-East China Normal University Center for Computational Chemistry at NYU Shanghai (China)
  9. New York Univ. (NYU), NY (United States). Department of Chemistry, Molecular Design Institute; Waseda Univ., Shinjuku (Japan). Department of Advanced Science and Engineering (TWIns)
Publication Date:
Research Org.:
Board of Regents Nevada System of Higher Education, Las Vegas, NV (United States)
Sponsoring Org.:
USDOE National Nuclear Security Administration (NNSA)
OSTI Identifier:
1426142
Grant/Contract Number:  
NA0001982; AC02-98CH10086
Resource Type:
Journal Article: Accepted Manuscript
Journal Name:
Chemical Science
Additional Journal Information:
Journal Volume: 8; Journal Issue: 7; Journal ID: ISSN 2041-6520
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Shtukenberg, Alexander G., Zhu, Qiang, Carter, Damien J., Vogt, Leslie, Hoja, Johannes, Schneider, Elia, Song, Hongxing, Pokroy, Boaz, Polishchuk, Iryna, Tkatchenko, Alexandre, Oganov, Artem R., Rohl, Andrew L., Tuckerman, Mark E., and Kahr, Bart. Powder diffraction and crystal structure prediction identify four new coumarin polymorphs. United States: N. p., 2017. Web. doi:10.1039/c7sc00168a.
Shtukenberg, Alexander G., Zhu, Qiang, Carter, Damien J., Vogt, Leslie, Hoja, Johannes, Schneider, Elia, Song, Hongxing, Pokroy, Boaz, Polishchuk, Iryna, Tkatchenko, Alexandre, Oganov, Artem R., Rohl, Andrew L., Tuckerman, Mark E., & Kahr, Bart. Powder diffraction and crystal structure prediction identify four new coumarin polymorphs. United States. doi:10.1039/c7sc00168a.
Shtukenberg, Alexander G., Zhu, Qiang, Carter, Damien J., Vogt, Leslie, Hoja, Johannes, Schneider, Elia, Song, Hongxing, Pokroy, Boaz, Polishchuk, Iryna, Tkatchenko, Alexandre, Oganov, Artem R., Rohl, Andrew L., Tuckerman, Mark E., and Kahr, Bart. Mon . "Powder diffraction and crystal structure prediction identify four new coumarin polymorphs". United States. doi:10.1039/c7sc00168a. https://www.osti.gov/servlets/purl/1426142.
@article{osti_1426142,
title = {Powder diffraction and crystal structure prediction identify four new coumarin polymorphs},
author = {Shtukenberg, Alexander G. and Zhu, Qiang and Carter, Damien J. and Vogt, Leslie and Hoja, Johannes and Schneider, Elia and Song, Hongxing and Pokroy, Boaz and Polishchuk, Iryna and Tkatchenko, Alexandre and Oganov, Artem R. and Rohl, Andrew L. and Tuckerman, Mark E. and Kahr, Bart},
abstractNote = {Coumarin, a simple, commodity chemical isolated from beans in 1820, has, to date, only yielded one solid state structure. Here, we report a rich polymorphism of coumarin grown from the melt. Four new metastable forms were identified and their crystal structures were solved using a combination of computational crystal structure prediction algorithms and X-ray powder diffraction. With five crystal structures, coumarin has become one of the few rigid molecules showing extensive polymorphism at ambient conditions. We demonstrate the crucial role of advanced electronic structure calculations including many-body dispersion effects for accurate ranking of the stability of coumarin polymorphs and the need to account for anharmonic vibrational contributions to their free energy. As such, coumarin is a model system for studying weak intermolecular interactions, crystallization mechanisms, and kinetic effects.},
doi = {10.1039/c7sc00168a},
journal = {Chemical Science},
issn = {2041-6520},
number = 7,
volume = 8,
place = {United States},
year = {2017},
month = {5}
}

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Cited by: 19 works
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    Works referencing / citing this record:

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    • Shtukenberg, Alexander G.; Punin, Yurii O.; Gujral, Ankit
    • Angewandte Chemie International Edition, Vol. 53, Issue 3
    • DOI: 10.1002/anie.201301223

    Many-Body Dispersion Interactions in Molecular Crystal Polymorphism
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    • Marom, Noa; DiStasio, Robert A.; Atalla, Viktor
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    • Hoja, Johannes; Reilly, Anthony M.; Tkatchenko, Alexandre
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    • Blum, Volker; Gehrke, Ralf; Hanke, Felix
    • Computer Physics Communications, Vol. 180, Issue 11
    • DOI: 10.1016/j.cpc.2009.06.022

    New developments in evolutionary structure prediction algorithm USPEX
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    • Lyakhov, Andriy O.; Oganov, Artem R.; Stokes, Harold T.
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    • DOI: 10.1016/j.cpc.2012.12.009

    Using experimental studies and theoretical calculations to analyze the molecular mechanism of coumarin, p-hydroxybenzoic acid, and cinnamic acid
    journal, May 2005


    Dispersion-Corrected Mean-Field Electronic Structure Methods
    journal, April 2016


    Modeling Polymorphic Molecular Crystals with Electronic Structure Theory
    journal, March 2016


    First-Principles Models for van der Waals Interactions in Molecules and Materials: Concepts, Theory, and Applications
    journal, March 2017


    Convergence Properties of Crystal Structure Prediction by Quasi-Random Sampling
    journal, January 2016

    • Case, David H.; Campbell, Josh E.; Bygrave, Peter J.
    • Journal of Chemical Theory and Computation, Vol. 12, Issue 2
    • DOI: 10.1021/acs.jctc.5b01112

    Exchange-Hole Dipole Dispersion Model for Accurate Energy Ranking in Molecular Crystal Structure Prediction
    journal, January 2017

    • Whittleton, Sarah R.; Otero-de-la-Roza, A.; Johnson, Erin R.
    • Journal of Chemical Theory and Computation, Vol. 13, Issue 2
    • DOI: 10.1021/acs.jctc.6b00679

    Harmonically Assisted Methods for Computing the Free Energy of Classical Crystals by Molecular Simulation: A Comparative Study
    journal, January 2017

    • Moustafa, Sabry G.; Schultz, Andrew J.; Kofke, David A.
    • Journal of Chemical Theory and Computation, Vol. 13, Issue 2
    • DOI: 10.1021/acs.jctc.6b01082

    How Evolutionary Crystal Structure Prediction Works—and Why
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    Realizing Predicted Crystal Structures at Extreme Conditions:  The Low-Temperature and High-Pressure Crystal Structures of 2-Chlorophenol and 4-Fluorophenol
    journal, May 2005

    • Oswald, Iain D. H.; Allan, David R.; Day, Graeme M.
    • Crystal Growth & Design, Vol. 5, Issue 3
    • DOI: 10.1021/cg049647b

    Hirshfeld Surfaces Identify Inadequacies in Computations of Intermolecular Interactions in Crystals: Pentamorphic 1,8-Dihydroxyanthraquinone
    journal, December 2008

    • Rohl, Andrew L.; Moret, Massimo; Kaminsky, Werner
    • Crystal Growth & Design, Vol. 8, Issue 12
    • DOI: 10.1021/cg8005212

    Phase Behavior and Polymorphism of Organic Crystals Confined within Nanoscale Chambers
    journal, November 2009

    • Ha, Jeong-Myeong; Hamilton, Benjamin D.; Hillmyer, Marc A.
    • Crystal Growth & Design, Vol. 9, Issue 11
    • DOI: 10.1021/cg9006185

    Conformational Polymorphism
    journal, December 2013

    • Cruz-Cabeza, Aurora J.; Bernstein, Joel
    • Chemical Reviews, Vol. 114, Issue 4
    • DOI: 10.1021/cr400249d

    Benchmarking Calculated Lattice Parameters and Energies of Molecular Crystals Using van der Waals Density Functionals
    journal, July 2014

    • Carter, Damien J.; Rohl, Andrew L.
    • Journal of Chemical Theory and Computation, Vol. 10, Issue 8
    • DOI: 10.1021/ct500335b

    Development and Testing of the OPLS All-Atom Force Field on Conformational Energetics and Properties of Organic Liquids
    journal, January 1996

    • Jorgensen, William L.; Maxwell, David S.; Tirado-Rives, Julian
    • Journal of the American Chemical Society, Vol. 118, Issue 45
    • DOI: 10.1021/ja9621760

    Resorcinol Crystallization from the Melt: A New Ambient Phase and New “Riddles”
    journal, March 2016

    • Zhu, Qiang; Shtukenberg, Alexander G.; Carter, Damien J.
    • Journal of the American Chemical Society, Vol. 138, Issue 14
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    Exploring the Lower Limit in Hydrogen Bonds:  Analysis of Weak C−H···O and C−H···π Interactions in Substituted Coumarins from Charge Density Analysis
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    Role of Electrostatic Interactions in Determining the Crystal Structures of Polar Organic Molecules. A Distributed Multipole Study
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    Density functional theory including dispersion corrections for intermolecular interactions in a large benchmark set of biologically relevant molecules
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    Modelling organic crystal structures using distributed multipole and polarizability-based model intermolecular potentials
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    Crystal-structure prediction of pyridine with four independent molecules
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    ROY revisited, again: the eighth solved structure
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    A benchmark for non-covalent interactions in solids
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    Perspective: Advances and challenges in treating van der Waals dispersion forces in density functional theory
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    Van der Waals Density Functional for General Geometries
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    Ab initio determination of the crystalline benzene lattice energy to sub-kilojoule/mole accuracy
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    Polymorphism of l -Tryptophan
    journal, November 2019

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    Hydrogen bonding vs. stacking interaction in the crystals of the simplest coumarin derivatives: a study from the energetic viewpoint
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    Polymorphism of l -Tryptophan
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    • Angewandte Chemie International Edition, Vol. 58, Issue 52
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    ROY revisited, again: the eighth solved structure
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    Hydrogen bonding vs. stacking interaction in the crystals of the simplest coumarin derivatives: a study from the energetic viewpoint
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    Discovery of new polymorphs of the tuberculosis drug isoniazid
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