Powder diffraction and crystal structure prediction identify four new coumarin polymorphs

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

doi:10.1039/c7sc00168a

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

Journal Article · Mon May 15 00:00:00 EDT 2017 · Chemical Science

DOI:https://doi.org/10.1039/c7sc00168a· OSTI ID:1426142

^[1];

^[2]; Carter, Damien J. ^[3];

^[4];

^[5]; Schneider, Elia ^[4]; Song, Hongxing ^[4]; Pokroy, Boaz ^[6]; Polishchuk, Iryna ^[6];

^[5];

^[7];

^[3]; Tuckerman, Mark E. ^[8];

^[9]

New York Univ. (NYU), NY (United States). Department of Chemistry, Molecular Design Institute
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
Curtin University, Perth (Australia). Curtin Institute for Computation and Department of Chemistry
New York Univ. (NYU), NY (United States). Department of Chemistry
Fritz-Haber-Institut der Max-Planck-Gesellschaft, Berlin (Germany); University of Luxembourg (Luxembourg). Physics and Materials Science Research Unit
Technion Israel Institute of Technology, Haifa (Israel). Department of Materials Science and Engineering, Russell Berrie Nanotechnology Institute
Skolkovo Institute of Science and Technology, Skolkovo Innovation Center, Moscow (Russia); Stony Brook Univ., NY (United States). Department of Geosciences
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)
New York Univ. (NYU), NY (United States). Department of Chemistry, Molecular Design Institute; Waseda Univ., Shinjuku (Japan). Department of Advanced Science and Engineering (TWIns)

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.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Board of Regents Nevada System of Higher Education, Las Vegas, NV (United States)

Sponsoring Organization:: USDOE National Nuclear Security Administration (NNSA)

Grant/Contract Number:: NA0001982; AC02-98CH10086

OSTI ID:: 1426142

Journal Information:: Chemical Science, Vol. 8, Issue 7; ISSN 2041-6520

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 82 works

Citation information provided by
Web of Science

References (80)

Generalized Gradient Approximation Made Simple Perdew, John P.; Burke, Kieron; Ernzerhof, Matthias Physical Review Letters, Vol. 77, Issue 18, p. 3865-3868 https://doi.org/10.1103/PhysRevLett.77.3865	journal	October 1996
Conformational Polymorphism Cruz-Cabeza, Aurora J.; Bernstein, Joel Chemical Reviews, Vol. 114, Issue 4 https://doi.org/10.1021/cr400249d	journal	December 2013
Transient Resonance Raman and ab Initio MO Calculation Studies of the Structures and Vibrational Assignments of the T ₁ State and the Anion Radical of Coumarin and Its Isotopically Substituted Analogues Uesugi, Yuki; Mizuno, Misao; Shimojima, Atsuhiko The Journal of Physical Chemistry A, Vol. 101, Issue 3 https://doi.org/10.1021/jp9626881	journal	January 1997
Projector augmented-wave method Blöchl, P. E. Physical Review B, Vol. 50, Issue 24, p. 17953-17979 https://doi.org/10.1103/PhysRevB.50.17953	journal	December 1994
Porous and Dense Magnesium Borohydride Frameworks: Synthesis, Stability, and Reversible Absorption of Guest Species Filinchuk, Yaroslav; Richter, Bo; Jensen, Torben R. Angewandte Chemie, Vol. 123, Issue 47 https://doi.org/10.1002/ange.201100675	journal	September 2011
Benchmarking Calculated Lattice Parameters and Energies of Molecular Crystals Using van der Waals Density Functionals Carter, Damien J.; Rohl, Andrew L. Journal of Chemical Theory and Computation, Vol. 10, Issue 8 https://doi.org/10.1021/ct500335b	journal	July 2014
First-Principles Determination of the Structure of Magnesium Borohydride Zhou, Xiang-Feng; Oganov, Artem R.; Qian, Guang-Rui Physical Review Letters, Vol. 109, Issue 24 https://doi.org/10.1103/PhysRevLett.109.245503	journal	December 2012
New developments in evolutionary structure prediction algorithm USPEX Lyakhov, Andriy O.; Oganov, Artem R.; Stokes, Harold T. Computer Physics Communications, Vol. 184, Issue 4 https://doi.org/10.1016/j.cpc.2012.12.009	journal	April 2013
COMPACK : a program for identifying crystal structure similarity using distances Chisholm, James Alexander; Motherwell, Sam Journal of Applied Crystallography, Vol. 38, Issue 1 https://doi.org/10.1107/S0021889804027074	journal	January 2005
Hirshfeld Surfaces Identify Inadequacies in Computations of Intermolecular Interactions in Crystals: Pentamorphic 1,8-Dihydroxyanthraquinone Rohl, Andrew L.; Moret, Massimo; Kaminsky, Werner Crystal Growth & Design, Vol. 8, Issue 12 https://doi.org/10.1021/cg8005212	journal	December 2008
Modelling organic crystal structures using distributed multipole and polarizability-based model intermolecular potentials Price, Sarah L.; Leslie, Maurice; Welch, Gareth W. A. Physical Chemistry Chemical Physics, Vol. 12, Issue 30 https://doi.org/10.1039/c004164e	journal	January 2010
Recent advances in magnetic structure determination by neutron powder diffraction Rodríguez-Carvajal, Juan Physica B: Condensed Matter, Vol. 192, Issue 1-2 https://doi.org/10.1016/0921-4526(93)90108-I	journal	October 1993
Exploring polymorphism of benzene and naphthalene with free energy based enhanced molecular dynamics Schneider, Elia; Vogt, Leslie; Tuckerman, Mark E. Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials, Vol. 72, Issue 4 https://doi.org/10.1107/S2052520616007873	journal	August 2016
Crystal-structure prediction of pyridine with four independent molecules van de Streek, Jacco; Neumann, Marcus A. CrystEngComm, Vol. 13, Issue 23 https://doi.org/10.1039/c1ce05881a	journal	January 2011
Resorcinol Crystallization from the Melt: A New Ambient Phase and New “Riddles” Zhu, Qiang; Shtukenberg, Alexander G.; Carter, Damien J. Journal of the American Chemical Society, Vol. 138, Issue 14 https://doi.org/10.1021/jacs.6b01120	journal	March 2016
First-Principles Models for van der Waals Interactions in Molecules and Materials: Concepts, Theory, and Applications Hermann, Jan; DiStasio, Robert A.; Tkatchenko, Alexandre Chemical Reviews, Vol. 117, Issue 6 https://doi.org/10.1021/acs.chemrev.6b00446	journal	March 2017
Fingerprinting intermolecular interactions in molecular crystals Spackman, Mark A.; McKinnon, Joshua J. CrystEngComm, Vol. 4, Issue 66 https://doi.org/10.1039/B203191B	journal	January 2002
Bernauer′s Bands Shtukenberg, Alexander; Gunn, Erica; Gazzano, Massimo ChemPhysChem, Vol. 12, Issue 8 https://doi.org/10.1002/cphc.201000963	journal	March 2011
First-principles modeling of molecular crystals: structures and stabilities, temperature and pressure: First-principles modeling of molecular crystals Hoja, Johannes; Reilly, Anthony M.; Tkatchenko, Alexandre Wiley Interdisciplinary Reviews: Computational Molecular Science, Vol. 7, Issue 1 https://doi.org/10.1002/wcms.1294	journal	December 2016
Ab initio determination of the crystalline benzene lattice energy to sub-kilojoule/mole accuracy Yang, J.; Hu, W.; Usvyat, D. Science, Vol. 345, Issue 6197 https://doi.org/10.1126/science.1254419	journal	August 2014
Accurate description of van der Waals complexes by density functional theory including empirical corrections Grimme, Stefan Journal of Computational Chemistry, Vol. 25, Issue 12 https://doi.org/10.1002/jcc.20078	journal	January 2004
Report on the sixth blind test of organic crystal structure prediction methods Reilly, Anthony M.; Cooper, Richard I.; Adjiman, Claire S. Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials, Vol. 72, Issue 4 https://doi.org/10.1107/S2052520616007447	journal	August 2016
Exploiting multiple levels of parallelism in Molecular Dynamics based calculations via modern techniques and software paradigms on distributed memory computers Tuckerman, Mark E.; Yarne, D. A.; Samuelson, Shane O. Computer Physics Communications, Vol. 128, Issue 1-2 https://doi.org/10.1016/S0010-4655(00)00077-1	journal	June 2000
Zum mikrochemischen Nachweis des Cumarins Kofler, A.; Geyr, J. Mikrochemie, Vol. 15, Issue 1 https://doi.org/10.1007/BF02789352	journal	December 1934
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 Munshi, Parthapratim; Guru Row, Tayur N. The Journal of Physical Chemistry A, Vol. 109, Issue 4 https://doi.org/10.1021/jp046388s	journal	February 2005
How Evolutionary Crystal Structure Prediction Works—and Why Oganov, Artem R.; Lyakhov, Andriy O.; Valle, Mario Accounts of Chemical Research, Vol. 44, Issue 3 https://doi.org/10.1021/ar1001318	journal	March 2011
Convergence Properties of Crystal Structure Prediction by Quasi-Random Sampling Case, David H.; Campbell, Josh E.; Bygrave, Peter J. Journal of Chemical Theory and Computation, Vol. 12, Issue 2 https://doi.org/10.1021/acs.jctc.5b01112	journal	January 2016
Role of Dispersion Interactions in the Polymorphism and Entropic Stabilization of the Aspirin Crystal Reilly, Anthony M.; Tkatchenko, Alexandre Physical Review Letters, Vol. 113, Issue 5 https://doi.org/10.1103/PhysRevLett.113.055701	journal	July 2014
Monte Carlo indexing with McMaille Le Bail, A. Powder Diffraction, Vol. 19, Issue 3 https://doi.org/10.1154/1.1763152	journal	September 2004
Effect of packing motifs on the energy ranking and electronic properties of putative crystal structures of tricyano-1,4-dithiino[ c ]-isothiazole Curtis, Farren; Wang, Xiaopeng; Marom, Noa Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials, Vol. 72, Issue 4 https://doi.org/10.1107/S2052520616009227	journal	August 2016
Organic crystal polymorphism: a benchmark for dispersion-corrected mean-field electronic structure methods Brandenburg, Jan Gerit; Grimme, Stefan Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials, Vol. 72, Issue 4 https://doi.org/10.1107/S2052520616007885	journal	August 2016
Using experimental studies and theoretical calculations to analyze the molecular mechanism of coumarin, p-hydroxybenzoic acid, and cinnamic acid Hsieh, Tiane-Jye; Su, Chia-Ching; Chen, Chung-Yi Journal of Molecular Structure, Vol. 741, Issue 1-3 https://doi.org/10.1016/j.molstruc.2005.02.009	journal	May 2005
Order-parameter-aided temperature-accelerated sampling for the exploration of crystal polymorphism and solid-liquid phase transitions Yu, Tang-Qing; Chen, Pei-Yang; Chen, Ming The Journal of Chemical Physics, Vol. 140, Issue 21 https://doi.org/10.1063/1.4878665	journal	June 2014
A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu Grimme, Stefan; Antony, Jens; Ehrlich, Stephan The Journal of Chemical Physics, Vol. 132, Issue 15 https://doi.org/10.1063/1.3382344	journal	April 2010
Realizing Predicted Crystal Structures at Extreme Conditions: The Low-Temperature and High-Pressure Crystal Structures of 2-Chlorophenol and 4-Fluorophenol Oswald, Iain D. H.; Allan, David R.; Day, Graeme M. Crystal Growth & Design, Vol. 5, Issue 3 https://doi.org/10.1021/cg049647b	journal	May 2005
Mikroskopische Untersuchungen an polymorphen Substanzen: II. Mitteilung Lindpaintner, E. Mikrochemie / Mikrochimica Acta, Vol. 27, Issue 1-2 https://doi.org/10.1007/BF01402981	journal	March 1939
Phase Behavior and Polymorphism of Organic Crystals Confined within Nanoscale Chambers Ha, Jeong-Myeong; Hamilton, Benjamin D.; Hillmyer, Marc A. Crystal Growth & Design, Vol. 9, Issue 11 https://doi.org/10.1021/cg9006185	journal	November 2009
Development and Testing of the OPLS All-Atom Force Field on Conformational Energetics and Properties of Organic Liquids Jorgensen, William L.; Maxwell, David S.; Tirado-Rives, Julian Journal of the American Chemical Society, Vol. 118, Issue 45 https://doi.org/10.1021/ja9621760	journal	January 1996
Thermal properties of molecular crystals through dispersion-corrected quasi-harmonic ab initio calculations: the case of urea Erba, Alessandro; Maul, Jefferson; Civalleri, Bartolomeo Chemical Communications, Vol. 52, Issue 9 https://doi.org/10.1039/C5CC08982D	journal	January 2016
Determination of the molecular packing in the crystal of coumarin by means of potential-energy calculations Gavuzzo, E.; Mazza, F.; Giglio, E. Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry, Vol. 30, Issue 5 https://doi.org/10.1107/S0567740874004791	journal	May 1974
Why don't we find more polymorphs? Price, Sarah L. Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials, Vol. 69, Issue 4 https://doi.org/10.1107/S2052519213018861	journal	July 2013
Higher-accuracy van der Waals density functional Lee, Kyuho; Murray, Éamonn D.; Kong, Lingzhu Physical Review B, Vol. 82, Issue 8 https://doi.org/10.1103/PhysRevB.82.081101	journal	August 2010
High-throughput crystallization: polymorphs, salts, co-crystals and solvates of pharmaceutical solids Morissette, S. Advanced Drug Delivery Reviews, Vol. 56, Issue 3 https://doi.org/10.1016/j.addr.2003.10.020	journal	February 2004
Efficient iterative schemes for ab initio total-energy calculations using a plane-wave basis set Kresse, G.; Furthmüller, J. Physical Review B, Vol. 54, Issue 16, p. 11169-11186 https://doi.org/10.1103/PhysRevB.54.11169	journal	October 1996
Dispersion-Corrected Mean-Field Electronic Structure Methods Grimme, Stefan; Hansen, Andreas; Brandenburg, Jan Gerit Chemical Reviews, Vol. 116, Issue 9 https://doi.org/10.1021/acs.chemrev.5b00533	journal	April 2016
A benchmark for non-covalent interactions in solids Otero-de-la-Roza, A.; Johnson, Erin R. The Journal of Chemical Physics, Vol. 137, Issue 5 https://doi.org/10.1063/1.4738961	journal	August 2012
Seamless and Accurate Modeling of Organic Molecular Materials Reilly, Anthony M.; Tkatchenko, Alexandre The Journal of Physical Chemistry Letters, Vol. 4, Issue 6 https://doi.org/10.1021/jz400226x	journal	March 2013
Toward reliable density functional methods without adjustable parameters: The PBE0 model Adamo, Carlo; Barone, Vincenzo The Journal of Chemical Physics, Vol. 110, Issue 13 https://doi.org/10.1063/1.478522	journal	April 1999
Perspective: Advances and challenges in treating van der Waals dispersion forces in density functional theory Klimeš, Jiří; Michaelides, Angelos The Journal of Chemical Physics, Vol. 137, Issue 12 https://doi.org/10.1063/1.4754130	journal	September 2012
Accurate and Efficient Method for Many-Body van der Waals Interactions Tkatchenko, Alexandre; DiStasio, Robert A.; Car, Roberto Physical Review Letters, Vol. 108, Issue 23 https://doi.org/10.1103/PhysRevLett.108.236402	journal	June 2012
Constrained evolutionary algorithm for structure prediction of molecular crystals: methodology and applications Zhu, Qiang; Oganov, Artem R.; Glass, Colin W. Acta Crystallographica Section B Structural Science, Vol. 68, Issue 3 https://doi.org/10.1107/S0108768112017466	journal	May 2012
Van der Waals Density Functional for General Geometries Dion, M.; Rydberg, H.; Schröder, E. Physical Review Letters, Vol. 92, Issue 24 https://doi.org/10.1103/PhysRevLett.92.246401	journal	June 2004
Static and lattice vibrational energy differences between polymorphs Nyman, Jonas; Day, Graeme M. CrystEngComm, Vol. 17, Issue 28 https://doi.org/10.1039/C5CE00045A	journal	January 2015
Growth Actuated Bending and Twisting of Single Crystals Shtukenberg, Alexander G.; Punin, Yurii O.; Gujral, Ankit Angewandte Chemie International Edition, Vol. 53, Issue 3 https://doi.org/10.1002/anie.201301223	journal	January 2014
Ab initio molecular simulations with numeric atom-centered orbitals Blum, Volker; Gehrke, Ralf; Hanke, Felix Computer Physics Communications, Vol. 180, Issue 11 https://doi.org/10.1016/j.cpc.2009.06.022	journal	November 2009
Upack program package for crystal structure prediction: Force fields and crystal structure generation for small carbohydrate molecules van Eijck, Bouke P.; Kroon, Jan Journal of Computational Chemistry, Vol. 20, Issue 8 https://doi.org/10.1002/(SICI)1096-987X(199906)20:8<799::AID-JCC6>3.0.CO;2-Z	journal	June 1999
Density functional theory including dispersion corrections for intermolecular interactions in a large benchmark set of biologically relevant molecules Antony, Jens; Grimme, Stefan Physical Chemistry Chemical Physics, Vol. 8, Issue 45 https://doi.org/10.1039/b612585a	journal	January 2006
Harmonically Assisted Methods for Computing the Free Energy of Classical Crystals by Molecular Simulation: A Comparative Study Moustafa, Sabry G.; Schultz, Andrew J.; Kofke, David A. Journal of Chemical Theory and Computation, Vol. 13, Issue 2 https://doi.org/10.1021/acs.jctc.6b01082	journal	January 2017
Understanding the role of vibrations, exact exchange, and many-body van der Waals interactions in the cohesive properties of molecular crystals Reilly, Anthony M.; Tkatchenko, Alexandre The Journal of Chemical Physics, Vol. 139, Issue 2 https://doi.org/10.1063/1.4812819	journal	July 2013
Role of Electrostatic Interactions in Determining the Crystal Structures of Polar Organic Molecules. A Distributed Multipole Study Coombes, David S.; Price, Sarah L.; Willock, David J. The Journal of Physical Chemistry, Vol. 100, Issue 18 https://doi.org/10.1021/jp960333b	journal	January 1996
Many-Body Dispersion Interactions in Molecular Crystal Polymorphism Marom, Noa; DiStasio, Robert A.; Atalla, Viktor Angewandte Chemie International Edition, Vol. 52, Issue 26 https://doi.org/10.1002/anie.201301938	journal	May 2013
Modeling Polymorphic Molecular Crystals with Electronic Structure Theory Beran, Gregory J. O. Chemical Reviews, Vol. 116, Issue 9 https://doi.org/10.1021/acs.chemrev.5b00648	journal	March 2016
A Projector Augmented Wave (PAW) code for electronic structure calculations, Part I: atompaw for generating atom-centered functions Holzwarth, N. A. W.; Tackett, A. R.; Matthews, G. E. Computer Physics Communications, Vol. 135, Issue 3 https://doi.org/10.1016/S0010-4655(00)00244-7	journal	April 2001
First-principles calculations of the ferroelastic transition between rutile-type and ${CaCl}_{2}$ -type ${SiO}_{2}$ at high pressures Togo, Atsushi; Oba, Fumiyasu; Tanaka, Isao Physical Review B, Vol. 78, Issue 13 https://doi.org/10.1103/PhysRevB.78.134106	journal	October 2008
Crystal structure prediction using ab initio evolutionary techniques: Principles and applications Oganov, Artem R.; Glass, Colin W. The Journal of Chemical Physics, Vol. 124, Issue 24 https://doi.org/10.1063/1.2210932	journal	June 2006
Exchange-Hole Dipole Dispersion Model for Accurate Energy Ranking in Molecular Crystal Structure Prediction Whittleton, Sarah R.; Otero-de-la-Roza, A.; Johnson, Erin R. Journal of Chemical Theory and Computation, Vol. 13, Issue 2 https://doi.org/10.1021/acs.jctc.6b00679	journal	January 2017
Porous and Dense Magnesium Borohydride Frameworks: Synthesis, Stability, and Reversible Absorption of Guest Species Filinchuk, Yaroslav; Richter, Bo; Jensen, Torben R. Angewandte Chemie International Edition, Vol. 50, Issue 47 https://doi.org/10.1002/anie.201100675	journal	September 2011
Mbd Hermann, Jan Zenodo https://doi.org/10.5281/zenodo.47528	software	March 2016
Many-Body Dispersion Interactions in Molecular Crystal Polymorphism Marom, Noa; DiStasio, Robert A.; Atalla, Viktor Angewandte Chemie, Vol. 125, Issue 26 https://doi.org/10.1002/ange.201301938	journal	May 2013
Quantum dissipation driven by electron transfer within a single molecule investigated with atomic force microscopy Berger, Jan; Ondráček, Martin; Stetsovych, Oleksandr Nature Communications, Vol. 11, Issue 1 https://doi.org/10.1038/s41467-020-15054-w	journal	March 2020
Electronic structure of AlFeN films exhibiting crystallographic orientation change from c- to a-axis with Fe concentrations and annealing effect Tatemizo, Nobuyuki; Imada, Saki; Okahara, Kizuna Scientific Reports, Vol. 10, Issue 1 https://doi.org/10.1038/s41598-020-58835-5	journal	February 2020
Constrained evolutionary algorithm for structure prediction of molecular crystals: methodology and applications Zhu, Qiang; Oganov, Artem R.; Glass, Colin W. arXiv https://doi.org/10.48550/arxiv.1204.4756	text	January 2012
A Materials Perspective on Casimir and van der Waals Interactions Woods, L. M.; Dalvit, D. A. R.; Tkatchenko, A. arXiv https://doi.org/10.48550/arxiv.1509.03338	text	January 2015
Anharmonic and Quantum Fluctuations in Molecular Crystals: A First-Principles Study of the Stability of Paracetamol Rossi, Mariana; Gasparotto, Piero; Ceriotti, Michele arXiv https://doi.org/10.48550/arxiv.1609.04469	text	January 2016
A New Era for ab initio Molecular Crystal Lattice Energy Prediction Beran, Gregory J. O. Angewandte Chemie International Edition https://doi.org/10.1002/anie.201409823	journal	October 2014
QUANTUM ESPRESSO: a modular and open-source software project for quantum simulations of materials Giannozzi, Paolo; Baroni, Stefano; Bonini, Nicola Journal of Physics: Condensed Matter, Vol. 21, Issue 39, Article No. 395502 https://doi.org/10.1088/0953-8984/21/39/395502	journal	September 2009
Temperature-Accelerated Method for Exploring Polymorphism in Molecular Crystals Based on Free Energy Yu, Tang-Qing; Tuckerman, Mark E. Physical Review Letters, Vol. 107, Issue 1 https://doi.org/10.1103/physrevlett.107.015701	journal	June 2011
Anharmonic and Quantum Fluctuations in Molecular Crystals: A First-Principles Study of the Stability of Paracetamol Rossi, Mariana; Gasparotto, Piero; Ceriotti, Michele Physical Review Letters, Vol. 117, Issue 11 https://doi.org/10.1103/physrevlett.117.115702	journal	September 2016
First-Principles Determination of the Structure of Magnesium Borohydride Zhou, Xiang-Feng; Oganov, Artem R.; Qian, Guang-Rui arXiv https://doi.org/10.48550/arxiv.1211.6948	text	January 2012
Van der Waals Density Functional for General Geometries Dion, M.; Rydberg, H.; Schroder, E. arXiv https://doi.org/10.48550/arxiv.cond-mat/0402105	text	January 2004

Cited By (26)

Polymorphism of l -Tryptophan Al Rahal, Okba; Hughes, Colan E.; Williams, P. Andrew Angewandte Chemie International Edition, Vol. 58, Issue 52 https://doi.org/10.1002/anie.201908247	journal	November 2019
In situ temperature-modulated microscopy observation of two-phase co-existing states of coumarin and coumarin derivative in melting Honda, Hidehiko Journal of Thermal Analysis and Calorimetry, Vol. 135, Issue 5 https://doi.org/10.1007/s10973-018-7952-x	journal	November 2018
Structure prediction drives materials discovery Oganov, Artem R.; Pickard, Chris J.; Zhu, Qiang Nature Reviews Materials, Vol. 4, Issue 5 https://doi.org/10.1038/s41578-019-0101-8	journal	April 2019
Computational polymorph screening reveals late-appearing and poorly-soluble form of rotigotine Mortazavi, Majid; Hoja, Johannes; Aerts, Luc Communications Chemistry, Vol. 2, Issue 1 https://doi.org/10.1038/s42004-019-0171-y	journal	June 2019
From serendipity to supramolecular design: assessing the utility of computed crystal form landscapes in inferring the risks of crystal hydration in carboxylic acids Mohamed, Sharmarke; Li, Liang CrystEngComm, Vol. 20, Issue 39 https://doi.org/10.1039/c8ce00758f	journal	January 2018
Crystal structure prediction of flexible pharmaceutical-like molecules: density functional tight-binding as an intermediate optimisation method and for free energy estimation Iuzzolino, Luca; McCabe, Patrick; Price, Sarah L. Faraday Discussions, Vol. 211 https://doi.org/10.1039/c8fd00010g	journal	January 2018
Crystal structure prediction is changing from basic science to applied technology Nyman, Jonas; Reutzel-Edens, Susan M. Faraday Discussions, Vol. 211 https://doi.org/10.1039/c8fd00033f	journal	January 2018
Towards the systematic crystallisation of molecular ionic cocrystals: insights from computed crystal form landscapes Mohamed, Sharmarke; Alwan, Ahmad A.; Friščić, Tomislav Faraday Discussions, Vol. 211 https://doi.org/10.1039/c8fd00036k	journal	January 2018
ROY revisited, again: the eighth solved structure Tan, Melissa; Shtukenberg, Alexander G.; Zhu, Shengcai Faraday Discussions, Vol. 211 https://doi.org/10.1039/c8fd00039e	journal	January 2018
First-principles stability ranking of molecular crystal polymorphs with the DFT+MBD approach Hoja, Johannes; Tkatchenko, Alexandre Faraday Discussions, Vol. 211 https://doi.org/10.1039/c8fd00066b	journal	January 2018
Is zeroth order crystal structure prediction (CSP_0) coming to maturity? What should we aim for in an ideal crystal structure prediction code? Price, Sarah L. Faraday Discussions, Vol. 211 https://doi.org/10.1039/c8fd00121a	journal	January 2018
Crystal structure prediction: reflections on present status and challenges Oganov, Artem R. Faraday Discussions, Vol. 211 https://doi.org/10.1039/c8fd90033g	journal	January 2018
Hydrogen bonding vs. stacking interaction in the crystals of the simplest coumarin derivatives: a study from the energetic viewpoint Shishkina, Svitlana V.; Konovalova, Irina S.; Kovalenko, Sergiy M. CrystEngComm, Vol. 21, Issue 45 https://doi.org/10.1039/c9ce01344j	journal	January 2019
Theory and practice of modeling van der Waals interactions in electronic-structure calculations Stöhr, Martin; Van Voorhis, Troy; Tkatchenko, Alexandre Chemical Society Reviews, Vol. 48, Issue 15 https://doi.org/10.1039/c9cs00060g	journal	January 2019
Discovery of new polymorphs of the tuberculosis drug isoniazid Zhang, Keke; Fellah, Noalle; Shtukenberg, Alexander G. CrystEngComm https://doi.org/10.1039/d0ce00440e	journal	January 2020
Towards hybrid density functional calculations of molecular crystals via fragment-based methods Loboda, Oleksandr A.; Dolgonos, Grygoriy A.; Boese, A. Daniel The Journal of Chemical Physics, Vol. 149, Issue 12 https://doi.org/10.1063/1.5046908	journal	September 2018
Reliable and practical computational description of molecular crystal polymorphs Hoja, Johannes; Ko, Hsin-Yu; Neumann, Marcus A. Science Advances, Vol. 5, Issue 1 https://doi.org/10.1126/sciadv.aau3338	journal	January 2019
A theoretical NMR study of selected benzazoles: Comparison of GIPAW and GIAO-PCM (DMSO) calculations Marín-Luna, Marta; Alkorta, Ibon; Elguero, José Magnetic Resonance in Chemistry, Vol. 56, Issue 3 https://doi.org/10.1002/mrc.4674	journal	November 2017
Evolutionary niching in the GAtor genetic algorithm for molecular crystal structure prediction Curtis, Farren; Rose, Timothy; Marom, Noa Faraday Discussions, Vol. 211 https://doi.org/10.1039/c8fd00067k	journal	January 2018
Overcoming the difficulties of predicting conformational polymorph energetics in molecular crystals via correlated wavefunction methods Greenwell, Chandler; McKinley, Jessica L.; Zhang, Peiyu Chemical Science, Vol. 11, Issue 8 https://doi.org/10.1039/c9sc05689k	journal	January 2020
Endpoint-restricted adiabatic free energy dynamics approach for the exploration of biomolecular conformational equilibria Cuendet, Michel A.; Margul, Daniel T.; Schneider, Elia The Journal of Chemical Physics, Vol. 149, Issue 7 https://doi.org/10.1063/1.5027479	journal	August 2018
Structure Prediction Drives Materials Discovery Oganov, Artem; Pickard, Christopher; Zhu, Qiang Apollo - University of Cambridge Repository https://doi.org/10.17863/cam.39313	text	January 2019
Towards Hybrid Density Functional Calculations of Molecular Crystals via Fragment-Based Methods Loboda, Oleksandr A.; Dolgonos, Grygoriy A.; Boese, A. Daniel arXiv https://doi.org/10.48550/arxiv.1809.09959	text	January 2018
PyXtal: A Python library for crystal structure generation and symmetry analysis Fredericks, Scott; Parrish, Kevin; Sayre, Dean Computer Physics Communications, Vol. 261 https://doi.org/10.1016/j.cpc.2020.107810	journal	April 2021
Using X-ray Diffraction Techniques for Biomimetic Drug Development, Formulation, and Polymorphic Characterization Rodríguez, Israel; Gautam, Ritika; Tinoco, Arthur D. Biomimetics, Vol. 6, Issue 1 https://doi.org/10.3390/biomimetics6010001	journal	December 2020
GAtor: A First Principles Genetic Algorithm for Molecular Crystal Structure Prediction Curtis, Farren; Li, Xiayue; Rose, Timothy arXiv https://doi.org/10.48550/arxiv.1802.08602	text	January 2018

Linked Research (6)

Similar Records

Beyond single crystals: Imaging rubrene polymorphism across crystalline batches through lattice phonon Raman microscopy

Journal Article · Wed Dec 15 00:00:00 EST 2021 · Journal of Chemical Physics · OSTI ID:1426142

Clapham, Margaret L.; Leighton, Ryan E.; Douglas, Christopher J.; +1 more

Single-crystal polarized electronic spectra of the compounds dichlorotetrakis(. mu. -pivalato)dirhenium(III), tetra-n-butylammonium octachlorodirhenate(III), tetra-n-butylammonium octabromodirhenate(III), dimolybdenum(II) tetrapivalate, and the x-ray diffraction crystal structures of tetra-n-butylammonium octabromodirhenate(III) and two polymorphs of dimolybdenum(II) tetrapivalate

Technical Report · Tue Oct 01 00:00:00 EDT 1985 · OSTI ID:1426142

Huang, H W

Crystal Engineering on Industrial Diaryl Pigments Using Lattice Energy Minimizations and X-ray Powder Diffraction

Journal Article · Mon Jan 01 00:00:00 EST 2007 · Journal of Physical Chemistry B · OSTI ID:1426142

Schmidt, M; Dinnebier, R; Kalkhof, H

Related Subjects

36 MATERIALS SCIENCE
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

CCDC 1542946: Experimental Crystal Structure Determination: 2H-1-benzopyran-2-one Shtukenberg, Alexander G.; Zhu, Qiang; Carter, Damien J. https://doi.org/10.5517/ccdc.csd.cc1nskgg The current record is supplemented by this dataset	dataset	April 2017
CCDC 1542947: Experimental Crystal Structure Determination: COUMAR14 : 2H-1-benzopyran-2-one Shtukenberg, Alexander; Zhu, Qiang; Carter, Damien https://doi.org/10.5517/ccdc.csd.cc1nskhh The current record is supplemented by this dataset	dataset	April 2017
CCDC 1542948: Experimental Crystal Structure Determination: COUMAR15 : 2H-1-benzopyran-2-one Shtukenberg, Alexander G.; Zhu, Qiang; Carter, Damien J. https://doi.org/10.5517/ccdc.csd.cc1nskjj The current record is supplemented by this dataset	dataset	April 2017
CCDC 1542949: Experimental Crystal Structure Determination: COUMAR16 : 2H-1-benzopyran-2-one Space Group: P 21 21 21 (19), Cell: a 24.27024(27)Å b 5.920620(65)Å c 14.18934(27)Å, α 90° β 90° γ 90° Shtukenberg, Alexander G.; Zhu, Qiang; Carter, Damien J. https://doi.org/10.5517/ccdc.csd.cc1nskkk The current record is supplemented by this dataset	dataset	April 2017
CCDC 1542950: Experimental Crystal Structure Determination: COUMAR17 : 2H-1-benzopyran-2-one Shtukenberg, Alexander G.; Zhu, Qiang; Carter, Damien J. https://doi.org/10.5517/ccdc.csd.cc1nskll The current record is supplemented by this dataset	dataset	April 2017
CCDC 1542951: Experimental Crystal Structure Determination: COUMAR18 : 2H-1-benzopyran-2-one Shtukenberg, Alexander G.; Zhu, Qiang; Carter, Damien J. https://doi.org/10.5517/ccdc.csd.cc1nskmm The current record is supplemented by this dataset	dataset	April 2017