Characterization of ephedrine HCl and pseudoephedrine HCl using quadrupolar NMR crystallography guided crystal structure prediction

Fleischer, Carl H.; Holmes, Sean T.; Levin, Kirill; Veinberg, Stanislav L.; Schurko, Robert W.

doi:10.1039/D4FD00089G

Characterization of ephedrine HCl and pseudoephedrine HCl using quadrupolar NMR crystallography guided crystal structure prediction

Journal Article · Tue Jan 07 23:00:00 EST 2025 · Faraday Discussions

DOI:https://doi.org/10.1039/D4FD00089G· OSTI ID:2447637

^[1]; ^[1]; ^[2]; Veinberg, Stanislav L. ^[2]; ^[1]

Department of Chemistry & Biochemistry, Florida State University, Tallahassee, FL 32306, USA, National High Magnetic Field Laboratory, Tallahassee, FL, 32310, USA
Department of Chemistry & Biochemistry, University of Windsor, Windsor, ON, N9B 3P4, Canada

We report a quadrupolar guided NMR crystallography crystal structure prediction protocol as applied for pseudoephedrine HCl and ephedrine HCl. We explore the crystal structure prediction of pseudoephedrine HCl in the dosage form.

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Sponsoring Organization:: USDOE

Grant/Contract Number:: SC0022310

OSTI ID:: 2447637

Journal Information:: Faraday Discussions, Journal Name: Faraday Discussions Vol. 255; ISSN 1359-6640; ISSN FDISE6

Publisher:: Royal Society of Chemistry (RSC)Copyright Statement

Country of Publication:: United Kingdom

Language:: English

References (122)

Spin echoes in half-integer quadrupole systems Chan, Jerry C. C. Concepts in Magnetic Resonance, Vol. 11, Issue 6 https://doi.org/10.1002/(SICI)1099-0534(1999)11:6<363::AID-CMR2>3.0.CO;2-A	journal	January 1999
Quadrupolar Nuclei in Solids Vega, Alexander J. eMagRes https://doi.org/10.1002/9780470034590.emrstm0431	book	March 2007
Fast Acquisition of Proton‐Detected HETCOR Solid‐State NMR Spectra of Quadrupolar Nuclei and Rapid Measurement of NH Bond Lengths by Frequency Selective HMQC and RESPDOR Pulse Sequences Wijesekara, Anuradha V.; Venkatesh, Amrit; Lampkin, Bryan J. Chemistry – A European Journal, Vol. 26, Issue 35 https://doi.org/10.1002/chem.202000390	journal	May 2020
¹³C CP/MAS: Application to glycine Taylor, Robert E. Concepts in Magnetic Resonance Part A, Vol. 22A, Issue 2 https://doi.org/10.1002/cmr.a.20015	journal	June 2004
Analysis of electric field gradient tensors at quadrupolar nuclei in common structural motifs Autschbach, Jochen; Zheng, Shaohui; Schurko, Robert W. Concepts in Magnetic Resonance Part A, Vol. 36A, Issue 2 https://doi.org/10.1002/cmr.a.20155	journal	March 2010
Exploring the Potential of Multinuclear Solid‐State ¹H, ¹³C, and ³⁵Cl Magnetic Resonance To Characterize Static and Dynamic Disorder in Pharmaceutical Hydrochlorides Szell, Patrick M. J.; Rehman, Zainab; Tatman, Ben P. ChemPhysChem, Vol. 24, Issue 3 https://doi.org/10.1002/cphc.202200558	journal	October 2022
Effect of the damping function in dispersion corrected density functional theory Grimme, Stefan; Ehrlich, Stephan; Goerigk, Lars Journal of Computational Chemistry, Vol. 32, Issue 7 https://doi.org/10.1002/jcc.21759	journal	March 2011
Solid-State NMR Analysis of a Boron-Containing Pharmaceutical Hydrochloride Salt Vogt, Frederick G.; Williams, Glenn R.; Copley, Royston C. B. Journal of Pharmaceutical Sciences, Vol. 102, Issue 10 https://doi.org/10.1002/jps.23679	journal	October 2013
Reducing the computational cost of NMR crystallography of organic powders at natural isotopic abundance with the help of ¹³ C- ¹³ C dipolar couplings Thureau, Pierre; Sturniolo, Simone; Zilka, Miri Magnetic Resonance in Chemistry, Vol. 57, Issue 5 https://doi.org/10.1002/mrc.4848	journal	March 2019
³⁵ Cl– ¹ H Heteronuclear correlation magic‐angle spinning nuclear magnetic resonance experiments for probing pharmaceutical salts Iuga, Dinu; Corlett, Emily K.; Brown, Steven P. Magnetic Resonance in Chemistry, Vol. 59, Issue 9-10 https://doi.org/10.1002/mrc.5188	journal	July 2021
Relaxation of Crystals with the Quasi-Newton Method Pfrommer, Bernd G.; Côté, Michel; Louie, Steven G. Journal of Computational Physics, Vol. 131, Issue 1 https://doi.org/10.1006/jcph.1996.5612	journal	February 1997
Comparing, Modeling, and Assigning Chemical-Shift Tensors in the Cartesian, Irreducible Spherical, and Icosahedral Representations Alderman, D. W.; Sherwood, M. H.; Grant, D. M. Journal of Magnetic Resonance, Series A, Vol. 101, Issue 2 https://doi.org/10.1006/jmra.1993.1029	journal	February 1993
Variable-Amplitude Cross-Polarization MAS NMR Peersen, O. B.; Wu, X. L.; Kustanovich, I. Journal of Magnetic Resonance, Series A, Vol. 104, Issue 3 https://doi.org/10.1006/jmra.1993.1231	journal	October 1993
Ramped-Amplitude Cross Polarization in Magic-Angle-Spinning NMR Metz, G.; Wu, X. L.; Smith, S. O. Journal of Magnetic Resonance, Series A, Vol. 110, Issue 2 https://doi.org/10.1006/jmra.1994.1208	journal	October 1994
Prediction and Calculation of Crystal Structures: Methods and Applications Atahan-Evrenk, Sule; Aspuru-Guzik, Alan Topics in Current Chemistry https://doi.org/10.1007/978-3-319-05774-3	book	January 2014
Proton-enhanced nuclear induction spectroscopy 13C chemical shielding anisotropy in some organic solids Pines, A.; Gibby, M. G.; Waugh, J. S. Chemical Physics Letters, Vol. 15, Issue 3 https://doi.org/10.1016/0009-2614(72)80191-X	journal	August 1972
Arrangements of ligands giving low electric field gradients Akitt, J. W.; McDonald, W. S. Journal of Magnetic Resonance (1969), Vol. 58, Issue 3 https://doi.org/10.1016/0022-2364(84)90144-6	journal	July 1984
Protein Crystallography and Drug Discovery Rondeau, Jean-Michel; Schreuder, Herman The Practice of Medicinal Chemistry, p. 511-537 https://doi.org/10.1016/B978-0-12-417205-0.00022-5	book	July 2015
NMR Crystallography Martineau, Charlotte; Senker, Jürgen; Taulelle, Francis Annual Reports on NMR Spectroscopy https://doi.org/10.1016/B978-0-12-800184-4.00001-1	book	January 2014
Computational Techniques McRee, Duncan E. Practical Protein Crystallography, p. 91-269 https://doi.org/10.1016/B978-012486052-0/50005-1	book	January 1999
High-resolution solid state 13C nuclear magnetic resonance spectra of 3,4-methylenedioxyamphetamine hydrochloride and related compounds and their mixtures with lactose Lee, Garry S. H.; Taylor, Renee C.; Dawson, Michael Solid State Nuclear Magnetic Resonance, Vol. 16, Issue 4 https://doi.org/10.1016/S0926-2040(00)00071-0	journal	July 2000
35Cl quadrupolar constants obtained by solid-state NMR: study of chlorinated Al–O–P clusters, involving OH⋯Cl hydrogen bonds Azaı̈s, T.; Bonhomme, C.; Smith, M. E. Solid State Nuclear Magnetic Resonance, Vol. 23, Issue 1-2 https://doi.org/10.1016/S0926-2040(02)00012-7	journal	February 2003
USPEX—Evolutionary crystal structure prediction Glass, Colin W.; Oganov, Artem R.; Hansen, Nikolaus Computer Physics Communications, Vol. 175, Issue 11-12 https://doi.org/10.1016/j.cpc.2006.07.020	journal	December 2006
XtalOpt: An open-source evolutionary algorithm for crystal structure prediction Lonie, David C.; Zurek, Eva Computer Physics Communications, Vol. 182, Issue 2 https://doi.org/10.1016/j.cpc.2010.07.048	journal	February 2011
CALYPSO: A method for crystal structure prediction Wang, Yanchao; Lv, Jian; Zhu, Li Computer Physics Communications, Vol. 183, Issue 10 https://doi.org/10.1016/j.cpc.2012.05.008	journal	October 2012
ssNake: A cross-platform open-source NMR data processing and fitting application van Meerten, S. G. J.; Franssen, W. M. J.; Kentgens, A. P. M. Journal of Magnetic Resonance, Vol. 301 https://doi.org/10.1016/j.jmr.2019.02.006	journal	April 2019
NMR crystallography of molecular organics Hodgkinson, Paul Progress in Nuclear Magnetic Resonance Spectroscopy, Vol. 118-119 https://doi.org/10.1016/j.pnmrs.2020.03.001	journal	June 2020
The PAW/GIPAW approach for computing NMR parameters: A new dimension added to NMR study of solids Charpentier, Thibault Solid State Nuclear Magnetic Resonance, Vol. 40, Issue 1 https://doi.org/10.1016/j.ssnmr.2011.04.006	journal	July 2011
15N chemical shift referencing in solid state NMR Bertani, Philippe; Raya, Jésus; Bechinger, Burkhard Solid State Nuclear Magnetic Resonance, Vol. 61-62 https://doi.org/10.1016/j.ssnmr.2014.03.003	journal	July 2014
Narrowing down the conformational space with solid-state NMR in crystal structure prediction of linezolid cocrystals Khalaji, Mehrnaz; Paluch, Piotr; Potrzebowski, Marek J. Solid State Nuclear Magnetic Resonance, Vol. 121, p. 101813 https://doi.org/10.1016/j.ssnmr.2022.101813	journal	August 2022
Hydrates of active pharmaceutical ingredients: A 35Cl and 2H solid-state NMR and DFT study Holmes, Sean T.; Vojvodin, Cameron S.; Veinberg, Natan Solid State Nuclear Magnetic Resonance, Vol. 122 https://doi.org/10.1016/j.ssnmr.2022.101837	journal	December 2022
An Introduction to X-ray Crystallography (2nd edition) Woolfson, Michael M. https://doi.org/10.1017/CBO9780511622557	book	January 2010
Crystal Structure Prediction via Efficient Sampling of the Potential Energy Surface Wang, Yanchao; Lv, Jian; Gao, Pengyue Accounts of Chemical Research, Vol. 55, Issue 15 https://doi.org/10.1021/acs.accounts.2c00243	journal	July 2022
Synergy of Solid-State NMR, Single-Crystal X-ray Diffraction, and Crystal Structure Prediction Methods: A Case Study of Teriflunomide (TFM) Pawlak, Tomasz; Sudgen, Isaac; Bujacz, Grzegorz Crystal Growth & Design, Vol. 21, Issue 6, p. 3328-3343 https://doi.org/10.1021/acs.cgd.1c00123	journal	May 2021
Synthesis and Characterization of Xylazine Hydrochloride Polymorphs, Hydrates, and Cocrystals: A ³⁵Cl Solid-State NMR and DFT Study Abdulla, Louae M.; Peach, Austin A.; Holmes, Sean T. Crystal Growth & Design, Vol. 23, Issue 5 https://doi.org/10.1021/acs.cgd.2c01539	journal	April 2023
Evaluating the Energetic Driving Force for Cocrystal Formation Taylor, Christopher R.; Day, Graeme M. Crystal Growth & Design, Vol. 18, Issue 2 https://doi.org/10.1021/acs.cgd.7b01375	journal	December 2017
Inconvenient Truths about Solid Form Landscapes Revealed in the Polymorphs and Hydrates of Gandotinib Braun, Doris E.; McMahon, Jennifer A.; Bhardwaj, Rajni M. Crystal Growth & Design, Vol. 19, Issue 5, p. 2947-2962 https://doi.org/10.1021/acs.cgd.9b00162	journal	April 2019
In Situ Characterization of Waters of Hydration in a Variable-Hydrate Active Pharmaceutical Ingredient Using ³⁵Cl Solid-State NMR and X-ray Diffraction Hirsh, David A.; Holmes, Sean T.; Chakravarty, Paroma Crystal Growth & Design, Vol. 19, Issue 12 https://doi.org/10.1021/acs.cgd.9b01218	journal	October 2019
Ab Initio Prediction of Metal-Organic Framework Structures Darby, James P.; Arhangelskis, Mihails; Katsenis, Athanassios D. Chemistry of Materials, Vol. 32, Issue 13 https://doi.org/10.1021/acs.chemmater.0c01737	journal	June 2020
Dispersion-Corrected DFT Methods for Applications in Nuclear Magnetic Resonance Crystallography Holmes, Sean T.; Vojvodin, Cameron S.; Schurko, Robert W. The Journal of Physical Chemistry A, Vol. 124, Issue 49 https://doi.org/10.1021/acs.jpca.0c06372	journal	December 2020
Exploring Systematic Discrepancies in DFT Calculations of Chlorine Nuclear Quadrupole Couplings Socha, Ondřej; Hodgkinson, Paul; Widdifield, Cory M. The Journal of Physical Chemistry A, Vol. 121, Issue 21 https://doi.org/10.1021/acs.jpca.7b02810	journal	May 2017
A Machine Learning Model of Chemical Shifts for Chemically and Structurally Diverse Molecular Solids Cordova, Manuel; Engel, Edgar A.; Stefaniuk, Artur The Journal of Physical Chemistry C, Vol. 126, Issue 39, p. 16710-16720 https://doi.org/10.1021/acs.jpcc.2c03854	journal	September 2022
Refining Crystal Structures with Quadrupolar NMR and Dispersion-Corrected Density Functional Theory Holmes, Sean T.; Schurko, Robert W. The Journal of Physical Chemistry C, Vol. 122, Issue 3 https://doi.org/10.1021/acs.jpcc.7b12314	journal	January 2018
Virtual Coformer Screening by Crystal Structure Predictions: Crucial Role of Crystallinity in Pharmaceutical Cocrystallization Sun, Guangxu; Jin, Yingdi; Li, Sizhu The Journal of Physical Chemistry Letters, Vol. 11, Issue 20 https://doi.org/10.1021/acs.jpclett.0c02371	journal	September 2020
Nutraceuticals in Bulk and Dosage Forms: Analysis by ³⁵Cl and ¹⁴N Solid-State NMR and DFT Calculations Holmes, Sean T.; Hook, James M.; Schurko, Robert W. Molecular Pharmaceutics, Vol. 19, Issue 2 https://doi.org/10.1021/acs.molpharmaceut.1c00708	journal	November 2021
Cocrystal Synthesis through Crystal Structure Prediction Abramov, Yuriy A.; Iuzzolino, Luca; Jin, Yingdi Molecular Pharmaceutics, Vol. 20, Issue 7 https://doi.org/10.1021/acs.molpharmaceut.2c01098	journal	June 2023
Ultrafast ¹H MAS NMR Crystallography for Natural Abundance Pharmaceutical Compounds Struppe, Jochem; Quinn, Caitlin M.; Sarkar, Sucharita Molecular Pharmaceutics, Vol. 17, Issue 2, 674-682 https://doi.org/10.1021/acs.molpharmaceut.9b01157	journal	December 2019
Computed Crystal Energy Landscapes for Understanding and Predicting Organic Crystal Structures and Polymorphism Price, Sarah (Sally) L. Accounts of Chemical Research, Vol. 42, Issue 1 https://doi.org/10.1021/ar800147t	journal	January 2009
An Assessment of Lattice Energy Minimization for the Prediction of Molecular Organic Crystal Structures Day, Graeme M.; Chisholm, James; Shan, Ning Crystal Growth & Design, Vol. 4, Issue 6 https://doi.org/10.1021/cg0498148	journal	November 2004
Enhancing Crystal-Structure Prediction with NMR Tensor Data Harper, James K.; Grant, David M. Crystal Growth & Design, Vol. 6, Issue 10 https://doi.org/10.1021/cg060244g	journal	September 2006
DREIDING: a generic force field for molecular simulations Mayo, Stephen L.; Olafson, Barry D.; Goddard, William A. The Journal of Physical Chemistry, Vol. 94, Issue 26, p. 8897-8909 https://doi.org/10.1021/j100389a010	journal	December 1990
Carbon-13 nuclear magnetic resonance of polymers spinning at the magic angle Schaefer, Jacob; Stejskal, E. O. Journal of the American Chemical Society, Vol. 98, Issue 4 https://doi.org/10.1021/ja00420a036	journal	February 1976
Characterization of Stereochemistry and Molecular Conformation Using Solid-State NMR Tensors Harper, James K.; Mulgrew, Anna E.; Li, Jia Yao Journal of the American Chemical Society, Vol. 123, Issue 40 https://doi.org/10.1021/ja010997l	journal	October 2001
De Novo Determination of the Crystal Structure of a Large Drug Molecule by Crystal Structure Prediction-Based Powder NMR Crystallography Baias, Maria; Dumez, Jean-Nicolas; Svensson, Per H. Journal of the American Chemical Society, Vol. 135, Issue 46 https://doi.org/10.1021/ja4088874	journal	November 2013
Application of Solid-State ³⁵ Cl NMR to the Structural Characterization of Hydrochloride Pharmaceuticals and their Polymorphs Hamaed, Hiyam; Pawlowski, Jenna M.; Cooper, Benjamin F. T. Journal of the American Chemical Society, Vol. 130, Issue 33 https://doi.org/10.1021/ja802486q	journal	August 2008
Powder Crystallography by Combined Crystal Structure Prediction and High-Resolution ¹ H Solid-State NMR Spectroscopy Salager, Elodie; Day, Graeme M.; Stein, Robin S. Journal of the American Chemical Society, Vol. 132, Issue 8 https://doi.org/10.1021/ja909449k	journal	March 2010
Rapid Structure Determination of Molecular Solids Using Chemical Shifts Directed by Unambiguous Prior Constraints Hofstetter, Albert; Balodis, Martins; Paruzzo, Federico M. Journal of the American Chemical Society, Vol. 141, Issue 42 https://doi.org/10.1021/jacs.9b03908	journal	May 2019
Stereochemical Analysis by Solid-State NMR: Structural Predictions in Ambuic Acid Harper, James K.; Barich, Dewey H.; Hu, Jian Z. The Journal of Organic Chemistry, Vol. 68, Issue 12 https://doi.org/10.1021/jo020377i	journal	June 2003
High-Field Chlorine NMR Spectroscopy of Solid Organic Hydrochloride Salts: A Sensitive Probe of Hydrogen Bonding Environment Bryce, David L.; Gee, Myrlene; Wasylishen, Roderick E. The Journal of Physical Chemistry A, Vol. 105, Issue 45 https://doi.org/10.1021/jp011962a	journal	October 2001
Combined First-Principles Computational and Experimental Multinuclear Solid-State NMR Investigation of Amino Acids Gervais, Christel; Dupree, Ray; Pike, Kevin J. The Journal of Physical Chemistry A, Vol. 109, Issue 31 https://doi.org/10.1021/jp0513925	journal	August 2005
Chlorine-35/37 NMR Spectroscopy of Solid Amino Acid Hydrochlorides: Refinement of Hydrogen-Bonded Proton Positions Using Experiment and Theory Bryce, David L.; Sward, Gregory D. The Journal of Physical Chemistry B, Vol. 110, Issue 51 https://doi.org/10.1021/jp065878c	journal	December 2006
NMR Crystallography of Campho[2,3-c]pyrazole (Z′ = 6): Combining High-Resolution ¹H-¹³C Solid-State MAS NMR Spectroscopy and GIPAW Chemical-Shift Calculations Webber, Amy L.; Emsley, Lyndon; Claramunt, Rosa M. The Journal of Physical Chemistry A, Vol. 114, Issue 38 https://doi.org/10.1021/jp104901j	journal	September 2010
Solid-State NMR Analysis of a Complex Crystalline Phase of Ronacaleret Hydrochloride Vogt, Frederick G.; Williams, Glenn R.; Strohmeier, Mark The Journal of Physical Chemistry B, Vol. 118, Issue 34 https://doi.org/10.1021/jp505061j	journal	August 2014
From computational discovery to experimental characterization of a high hole mobility organic crystal Sokolov, Anatoliy N.; Atahan-Evrenk, Sule; Mondal, Rajib Nature Communications, Vol. 2, Issue 1 https://doi.org/10.1038/ncomms1451	journal	August 2011
Combined crystal structure prediction and high-pressure crystallization in rational pharmaceutical polymorph screening Neumann, M. A.; van de Streek, J.; Fabbiani, F. P. A. Nature Communications, Vol. 6, Issue 1 https://doi.org/10.1038/ncomms8793	journal	July 2015
Crystal structure prediction from first principles Woodley, Scott M.; Catlow, Richard Nature Materials, Vol. 7, Issue 12 https://doi.org/10.1038/nmat2321	journal	December 2008
Chemical shifts in molecular solids by machine learning Paruzzo, Federico M.; Hofstetter, Albert; Musil, Félix Nature Communications, Vol. 9, Issue 1 https://doi.org/10.1038/s41467-018-06972-x	journal	October 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
Combining solid-state NMR spectroscopy with first-principles calculations – a guide to NMR crystallography Ashbrook, Sharon E.; McKay, David Chemical Communications, Vol. 52, Issue 45 https://doi.org/10.1039/C6CC02542K	journal	January 2016
³⁵ Cl solid-state NMR spectroscopy of HCl pharmaceuticals and their polymorphs in bulk and dosage forms Namespetra, Andrew M.; Hirsh, David A.; Hildebrand, Marcel P. CrystEngComm, Vol. 18, Issue 33 https://doi.org/10.1039/C6CE01069E	journal	January 2016
Multi-component crystals containing urea: mechanochemical synthesis and characterization by ³⁵Cl solid-state NMR spectroscopy and DFT calculations Vojvodin, Cameron S.; Holmes, Sean T.; Watanabe, Lara K. CrystEngComm, Vol. 24, Issue 14 https://doi.org/10.1039/D1CE01610E	journal	January 2022
Quadrupolar NMR crystallography guided crystal structure prediction (QNMRX-CSP) Peach, Austin A.; Fleischer, Carl H.; Levin, Kirill CrystEngComm, Vol. 26, Issue 35, p. 4782-4803 https://doi.org/10.1039/D3CE01306E	journal	July 2024
GULP: A computer program for the symmetry-adapted simulation of solids Gale, Julian D. Journal of the Chemical Society, Faraday Transactions, Vol. 93, Issue 4 https://doi.org/10.1039/a606455h	journal	January 1997
NMRcrystallography of oxybuprocaine hydrochloride, Modification II° Harris, Robin K.; Cadars, Sylvian; Emsley, Lyndon Phys. Chem. Chem. Phys., Vol. 9, Issue 3 https://doi.org/10.1039/b614318k	journal	January 2007
A high-field solid-state 35/37Cl NMR and quantum chemical investigation of the chlorine quadrupolar and chemical shift tensors in amino acid hydrochlorides Chapman, Rebecca P.; Bryce, David L. Physical Chemistry Chemical Physics, Vol. 9, Issue 47 https://doi.org/10.1039/b712688c	journal	January 2007
Application of multinuclear magnetic resonance and gauge-including projector-augmented-wave calculations to the study of solid group 13 chlorides Chapman, Rebecca P.; Bryce, David L. Physical Chemistry Chemical Physics, Vol. 11, Issue 32 https://doi.org/10.1039/b906627f	journal	January 2009
Refining crystal structures with experimental 13C NMR shift tensors and lattice-including electronic structure methods Harper, James K.; Iuliucci, Robbie; Gruber, Matthew CrystEngComm, Vol. 15, Issue 43 https://doi.org/10.1039/c3ce40108a	journal	January 2013
NMR crystallography: the use of dipolar interactions in polymorph and co-crystal investigation Chierotti, Michele R.; Gobetto, Roberto CrystEngComm, Vol. 15, Issue 43 https://doi.org/10.1039/c3ce41026a	journal	January 2013
Powder crystallography of pharmaceutical materials by combined crystal structure prediction and solid-state 1H NMR spectroscopy Baias, Maria; Widdifield, Cory M.; Dumez, Jean-Nicolas Physical Chemistry Chemical Physics, Vol. 15, Issue 21 https://doi.org/10.1039/c3cp41095a	journal	January 2013
Predicting crystal structures of organic compounds Price, Sarah L. Chem. Soc. Rev., Vol. 43, Issue 7 https://doi.org/10.1039/c3cs60279f	journal	January 2014
³⁵ Cl solid-state NMR of HCl salts of active pharmaceutical ingredients: structural prediction, spectral fingerprinting and polymorph recognition Hildebrand, Marcel; Hamaed, Hiyam; Namespetra, Andrew M. CrystEngComm, Vol. 16, Issue 31 https://doi.org/10.1039/c4ce00544a	journal	January 2014
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
Two-dimensional proton-detected ³⁵ Cl/ ¹ H correlation solid-state NMR experiment under fast magic angle sample spinning: application to pharmaceutical compounds Pandey, Manoj Kumar; Kato, Hiroshi; Ishii, Yuji Physical Chemistry Chemical Physics, Vol. 18, Issue 8 https://doi.org/10.1039/c5cp06042g	journal	January 2016
Does Z′ equal 1 or 2? Enhanced powder NMR crystallography verification of a disordered room temperature crystal structure of a p38 inhibitor for chronic obstructive pulmonary disease Widdifield, Cory M.; Nilsson Lill, Sten O.; Broo, Anders Physical Chemistry Chemical Physics, Vol. 19, Issue 25, p. 16650-16661 https://doi.org/10.1039/c7cp02349a	journal	June 2017
Mechanochemical syntheses and ³⁵ Cl solid-state NMR characterization of fluoxetine HCl cocrystals Peach, Austin A.; Hirsh, David A.; Holmes, Sean T. CrystEngComm, Vol. 20, Issue 20 https://doi.org/10.1039/c8ce00378e	journal	January 2018
Crystal-energy landscapes of active pharmaceutical ingredients using composite approaches LeBlanc, Luc M.; Johnson, Erin R. CrystEngComm, Vol. 21, Issue 40 https://doi.org/10.1039/c9ce00895k	journal	January 2019
Resolving alternative organic crystal structures using density functional theory and NMR chemical shifts Widdifield, Cory M.; Farrell, James D.; Cole, Jason C. Chemical Science, Vol. 11, Issue 11 https://doi.org/10.1039/c9sc04964a	journal	January 2020
Crystal structure determination of an elusive methanol solvate – hydrate of catechin using crystal structure prediction and NMR crystallography Dudek, Marta K.; Paluch, Piotr; Śniechowska, Justyna CrystEngComm, Vol. 22, Issue 30, p. 4969-4981 https://doi.org/10.1039/d0ce00452a	journal	June 2020
Evolutionary chemical space exploration for functional materials: computational organic semiconductor discovery Cheng, Chi Y.; Campbell, Josh E.; Day, Graeme M. Chemical Science, Vol. 11, Issue 19 https://doi.org/10.1039/d0sc00554a	journal	January 2020
Along the road to crystal structure prediction (CSP) of pharmaceutical-like molecules Dudek, Marta K.; Drużbicki, Kacper CrystEngComm, Vol. 24, Issue 9, p. 1665-1678 https://doi.org/10.1039/d1ce01564h	journal	February 2022
Frontiers of molecular crystal structure prediction for pharmaceuticals and functional organic materials Beran, Gregory J. O. Chemical Science, Vol. 14, Issue 46, p. 13290-13312 https://doi.org/10.1039/d3sc03903j	journal	November 2023
Proton‐enhanced NMR of dilute spins in solids Pines, A.; Gibby, M. G.; Waugh, J. S. The Journal of Chemical Physics, Vol. 59, Issue 2 https://doi.org/10.1063/1.1680061	journal	July 1973
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
The zero‐order regular approximation for relativistic effects: The effect of spin–orbit coupling in closed shell molecules van Lenthe, E.; Snijders, J. G.; Baerends, E. J. The Journal of Chemical Physics, Vol. 105, Issue 15 https://doi.org/10.1063/1.472460	journal	October 1996
Extension of the D3 dispersion coefficient model Caldeweyher, Eike; Bannwarth, Christoph; Grimme, Stefan The Journal of Chemical Physics, Vol. 147, Issue 3 https://doi.org/10.1063/1.4993215	journal	July 2017
Year-2017 nuclear quadrupole moments Pyykkö, Pekka Molecular Physics, Vol. 116, Issue 10 https://doi.org/10.1080/00268976.2018.1426131	journal	February 2018
Current approaches to predicting molecular organic crystal structures Day, Graeme M. Crystallography Reviews, Vol. 17, Issue 1 https://doi.org/10.1080/0889311X.2010.517526	journal	January 2011
Monte Carlo methods in Materials Studio Akkermans, Reinier L. C.; Spenley, Neil A.; Robertson, Struan H. Molecular Simulation, Vol. 39, Issue 14-15 https://doi.org/10.1080/08927022.2013.843775	journal	December 2013
CrySPY: a crystal structure prediction tool accelerated by machine learning Yamashita, Tomoki; Kanehira, Shinichi; Sato, Nobuya Science and Technology of Advanced Materials: Methods, Vol. 1, Issue 1, p. 87-97 https://doi.org/10.1080/27660400.2021.1943171	journal	January 2021
Ab initio random structure searching Pickard, Chris J.; Needs, R. J. Journal of Physics: Condensed Matter, Vol. 23, Issue 5 https://doi.org/10.1088/0953-8984/23/5/053201	journal	January 2011
The Weak Hydrogen Bond Desiraju, Gautam; Steiner, Thomas Oxford University Press https://doi.org/10.1093/acprof:oso/9780198509707.001.0001	book	January 2001
MAGUS: machine learning and graph theory assisted universal structure searcher Wang, Junjie; Gao, Hao; Han, Yu National Science Review, Vol. 10, Issue 7 https://doi.org/10.1093/nsr/nwad128	journal	May 2023
Spin Echoes Hahn, E. L. Physical Review, Vol. 80, Issue 4 https://doi.org/10.1103/PhysRev.80.580	journal	November 1950
Calculation of NMR chemical shifts for extended systems using ultrasoft pseudopotentials Yates, Jonathan R.; Pickard, Chris J.; Mauri, Francesco Physical Review B, Vol. 76, Issue 2 https://doi.org/10.1103/PhysRevB.76.024401	journal	July 2007
A test of crystal structure prediction of small organic molecules Lommerse, Jos P. M.; Motherwell, W. D. Sam; Ammon, Herman L. Acta Crystallographica Section B Structural Science, Vol. 56, Issue 4 https://doi.org/10.1107/S0108768100004584	journal	August 2000
The Cambridge Structural Database: a quarter of a million crystal structures and rising Allen, Frank H. Acta Crystallographica Section B Structural Science, Vol. 58, Issue 3 https://doi.org/10.1107/S0108768102003890	journal	May 2002
Crystal structure prediction of small organic molecules: a second blind test Motherwell, W. D. Sam; Ammon, Herman L.; Dunitz, Jack D. Acta Crystallographica Section B Structural Science, Vol. 58, Issue 4 https://doi.org/10.1107/S0108768102005669	journal	July 2002
A third blind test of crystal structure prediction Day, G. M.; Motherwell, W. D. S.; Ammon, H. L. Acta Crystallographica Section B Structural Science, Vol. 61, Issue 5 https://doi.org/10.1107/S0108768105016563	journal	September 2005
17 salts of ephedrine: crystal structures and packing analysis Collier, Edwin A.; Davey, Roger J.; Black, Simon N. Acta Crystallographica Section B Structural Science, Vol. 62, Issue 3 https://doi.org/10.1107/S0108768106012018	journal	May 2006
Significant progress in predicting the crystal structures of small organic molecules – a report on the fourth blind test Day, Graeme M.; Cooper, Timothy G.; Cruz-Cabeza, Aurora J. Acta Crystallographica Section B Structural Science, Vol. 65, Issue 2 https://doi.org/10.1107/S0108768109004066	journal	March 2009
Towards crystal structure prediction of complex organic compounds – a report on the fifth blind test Bardwell, David A.; Adjiman, Claire S.; Arnautova, Yelena A. Acta Crystallographica Section B Structural Science, Vol. 67, Issue 6 https://doi.org/10.1107/S0108768111042868	journal	November 2011
The crystal and molecular structures of (+)-pseudoephedrine and (+)-pseudoephedrine hydrochloride Mathew, M.; Palenik, G. J. Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry, Vol. 33, Issue 4 https://doi.org/10.1107/S0567740877005287	journal	April 1977
Mercury 4.0 : from visualization to analysis, design and prediction Macrae, Clare F.; Sovago, Ioana; Cottrell, Simon J. Journal of Applied Crystallography, Vol. 53, Issue 1 https://doi.org/10.1107/S1600576719014092	journal	February 2020
NMR crystallography: structure and properties of materials from solid-state nuclear magnetic resonance observables Bryce, David L. IUCrJ, Vol. 4, Issue 4 https://doi.org/10.1107/S2052252517006042	journal	May 2017
The Cambridge Structural Database Groom, Colin R.; Bruno, Ian J.; Lightfoot, Matthew P. Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials, Vol. 72, Issue 2, p. 171-179 https://doi.org/10.1107/S2052520616003954	journal	April 2016
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
A multinuclear NMR and quantum chemical study of solid trimethylammonium chloride Penner, Glenn H.; Webber, Renee; O’Dell, Luke A. Canadian Journal of Chemistry, Vol. 89, Issue 9 https://doi.org/10.1139/v11-034	journal	September 2011
Crystal Structure Prediction Methods for Organic Molecules: State of the Art Bowskill, David H.; Sugden, Isaac J.; Konstantinopoulos, Stefanos Annual Review of Chemical and Biomolecular Engineering, Vol. 12, Issue 1 https://doi.org/10.1146/annurev-chembioeng-060718-030256	journal	June 2021
Using the Cambridge Structural Database to validate powder structures Barr, G.; Dong, W.; Gilmore, C. J. Zeitschrift für Kristallographie, Vol. 2007, Issue suppl_26 https://doi.org/10.1524/zkri.2007.2007.suppl_26.209	journal	November 2007
First principles methods using CASTEP Clark, Stewart J.; Segall, Matthew D.; Pickard, Chris J. Zeitschrift für Kristallographie - Crystalline Materials, Vol. 220, Issue 5/6 https://doi.org/10.1524/zkri.220.5.567.65075	journal	January 2005
NMR Crystallography as a Vital Tool in Assisting Crystal Structure Determination from Powder XRD Data Harris, Kenneth D. M. Crystals, Vol. 12, Issue 9 https://doi.org/10.3390/cryst12091277	journal	September 2022
Zwitterionic or Not? Fast and Reliable Structure Determination by Combining Crystal Structure Prediction and Solid-State NMR Bravetti, Federica; Russo, Raffaele E.; Bordignon, Simone Molecules, Vol. 28, Issue 4 https://doi.org/10.3390/molecules28041876	journal	February 2023

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