Report on the sixth blind test of organic crystal structure prediction methods

Anthony M. Reilly; Richard I. Cooper; Claire S. Adjiman; Saswata Bhattacharya; A. Daniel Boese; Jan Gerit Brandenburg; Peter J. Bygrave; Rita Bylsma; Josh E. Campbell; Roberto Car; David H. Case; Renu Chadha; Jason C. Cole; Katherine Cosburn; Herma M. Cuppen; Farren Curtis; Graeme M. Day; Robert A. DiStasio; Alexander Dzyabchenko; Bouke P. Van Eijck; Dennis M. Elking; Joost A. Van Den Ende; Julio C. Facelli; Marta B. Ferraro; Laszlo Fusti-Molnar; Christina Anna Gatsiou; Thomas S. Gee; René De Gelder; Luca M. Ghiringhelli; Hitoshi Goto; Stefan Grimme; Rui Guo; Detlef W.M. Hofmann; Johannes Hoja; Rebecca K. Hylton; Luca Iuzzolino; Wojciech Jankiewicz; Daniël T. De Jong; John Kendrick; Niek J.J. De Klerk; Hsin Yu Ko; Liudmila N. Kuleshova; Xiayue Li; Sanjaya Lohani; Frank J.J. Leusen; Albert M. Lund; Jian Lv; Yanming Ma; Noa Marom; Artëm E. Masunov; Patrick McCabe; David P. McMahon; Hugo Meekes; Michael P. Metz; Alston J. Misquitta; Sharmarke Mohamed; Bartomeu Monserrat; Richard J. Needs; Marcus A. Neumann; Jonas Nyman; Shigeaki Obata; Harald Oberhofer; Artem R. Oganov; Anita M. Orendt; Gabriel I. Pagola; Constantinos C. Pantelides; Chris J. Pickard; Rafal Podeszwa; Louise S. Price; Sarah L. Price; Angeles Pulido; Murray G. Read; Karsten Reuter; Elia Schneider; Christoph Schober; Gregory P. Shields; Pawanpreet Singh; Isaac J. Sugden; Krzysztof Szalewicz; Christopher R. Taylor; Alexandre Tkatchenko; Mark E. Tuckerman; Francesca Vacarro; Manolis Vasileiadis; Alvaro Vazquez-Mayagoitia; Leslie Vogt; Yanchao Wang; Rona E. Watson; Gilles A. De Wijs; Jack Yang; Qiang Zhu; Colin R. Groom

doi:10.1107/S2052520616007447

Report on the sixth blind test of organic crystal structure prediction methods

Anthony M. Reilly, Richard I. Cooper, Claire S. Adjiman, Saswata Bhattacharya, A. Daniel Boese, Jan Gerit Brandenburg, Peter J. Bygrave, Rita Bylsma, Josh E. Campbell, Roberto Car, David H. Case, Renu Chadha, Jason C. Cole, Katherine Cosburn, Herma M. Cuppen, Farren Curtis, Graeme M. Day, Robert A. DiStasio, Alexander Dzyabchenko, Bouke P. Van EijckDennis M. Elking, Joost A. Van Den Ende, Julio C. Facelli, Marta B. Ferraro, Laszlo Fusti-Molnar, Christina Anna Gatsiou, Thomas S. Gee, René De Gelder, Luca M. Ghiringhelli, Hitoshi Goto, Stefan Grimme, Rui Guo, Detlef W.M. Hofmann, Johannes Hoja, Rebecca K. Hylton, Luca Iuzzolino, Wojciech Jankiewicz, Daniël T. De Jong, John Kendrick, Niek J.J. De Klerk, Hsin Yu Ko, Liudmila N. Kuleshova, Xiayue Li, Sanjaya Lohani, Frank J.J. Leusen, Albert M. Lund, Jian Lv, Yanming Ma, Noa Marom, Artëm E. Masunov, Patrick McCabe, David P. McMahon, Hugo Meekes, Michael P. Metz, Alston J. Misquitta, Sharmarke Mohamed, Bartomeu Monserrat, Richard J. Needs, Marcus A. Neumann, Jonas Nyman, Shigeaki Obata, Harald Oberhofer, Artem R. Oganov, Anita M. Orendt, Gabriel I. Pagola, Constantinos C. Pantelides, Chris J. Pickard, Rafal Podeszwa, Louise S. Price, Sarah L. Price, Angeles Pulido, Murray G. Read, Karsten Reuter, Elia Schneider, Christoph Schober, Gregory P. Shields, Pawanpreet Singh, Isaac J. Sugden, Krzysztof Szalewicz, Christopher R. Taylor, Alexandre Tkatchenko, Mark E. Tuckerman, Francesca Vacarro, Manolis Vasileiadis, Alvaro Vazquez-Mayagoitia, Leslie Vogt, Yanchao Wang, Rona E. Watson, Gilles A. De Wijs, Jack Yang, Qiang Zhu, Colin R. Groom

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

The sixth blind test of organic crystal structure prediction (CSP) methods has been held, with five target systems: a small nearly rigid molecule, a polymorphic former drug candidate, a chloride salt hydrate, a co-crystal and a bulky flexible molecule. This blind test has seen substantial growth in the number of participants, with the broad range of prediction methods giving a unique insight into the state of the art in the field. Significant progress has been seen in treating flexible molecules, usage of hierarchical approaches to ranking structures, the application of density-functional approximations, and the establishment of new workflows and 'best practices' for performing CSP calculations. All of the targets, apart from a single potentially disordered Z′ = 2 polymorph of the drug candidate, were predicted by at least one submission. Despite many remaining challenges, it is clear that CSP methods are becoming more applicable to a wider range of real systems, including salts, hydrates and larger flexible molecules. The results also highlight the potential for CSP calculations to complement and augment experimental studies of organic solid forms.The results of the sixth blind test of organic crystal structure prediction methods are presented and discussed, highlighting progress for salts, hydrates and bulky flexible molecules, as well as on-going challenges.

Original language	English (US)
Pages (from-to)	439-459
Number of pages	21
Journal	Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials
Volume	72
Issue number	4
DOIs	https://doi.org/10.1107/S2052520616007447
State	Published - Aug 1 2016

Keywords

Cambridge Structural Database
crystal structure prediction
lattice energies
polymorphism

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
Atomic and Molecular Physics, and Optics
Metals and Alloys
Materials Chemistry

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10.1107/S2052520616007447

Cite this

Reilly, A. M., Cooper, R. I., Adjiman, C. S., Bhattacharya, S., Boese, A. D., Brandenburg, J. G., Bygrave, P. J., Bylsma, R., Campbell, J. E., Car, R., Case, D. H., Chadha, R., Cole, J. C., Cosburn, K., Cuppen, H. M., Curtis, F., Day, G. M., DiStasio, R. A., Dzyabchenko, A., ... Groom, C. R. (2016). Report on the sixth blind test of organic crystal structure prediction methods. Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials, 72(4), 439-459. https://doi.org/10.1107/S2052520616007447

Reilly, AM, Cooper, RI, Adjiman, CS, Bhattacharya, S, Boese, AD, Brandenburg, JG, Bygrave, PJ, Bylsma, R, Campbell, JE, Car, R, Case, DH, Chadha, R, Cole, JC, Cosburn, K, Cuppen, HM, Curtis, F, Day, GM, DiStasio, RA, Dzyabchenko, A, Van Eijck, BP, Elking, DM, Van Den Ende, JA, Facelli, JC, Ferraro, MB, Fusti-Molnar, L, Gatsiou, CA, Gee, TS, De Gelder, R, Ghiringhelli, LM, Goto, H, Grimme, S, Guo, R, Hofmann, DWM, Hoja, J, Hylton, RK, Iuzzolino, L, Jankiewicz, W, De Jong, DT, Kendrick, J, De Klerk, NJJ, Ko, HY, Kuleshova, LN, Li, X, Lohani, S, Leusen, FJJ, Lund, AM, Lv, J, Ma, Y, Marom, N, Masunov, AE, McCabe, P, McMahon, DP, Meekes, H, Metz, MP, Misquitta, AJ, Mohamed, S, Monserrat, B, Needs, RJ, Neumann, MA, Nyman, J, Obata, S, Oberhofer, H, Oganov, AR, Orendt, AM, Pagola, GI, Pantelides, CC, Pickard, CJ, Podeszwa, R, Price, LS, Price, SL, Pulido, A, Read, MG, Reuter, K, Schneider, E, Schober, C, Shields, GP, Singh, P, Sugden, IJ, Szalewicz, K, Taylor, CR, Tkatchenko, A, Tuckerman, ME, Vacarro, F, Vasileiadis, M, Vazquez-Mayagoitia, A, Vogt, L, Wang, Y, Watson, RE, De Wijs, GA, Yang, J, Zhu, Q & Groom, CR 2016, 'Report on the sixth blind test of organic crystal structure prediction methods', Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials, vol. 72, no. 4, pp. 439-459. https://doi.org/10.1107/S2052520616007447

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title = "Report on the sixth blind test of organic crystal structure prediction methods",

abstract = "The sixth blind test of organic crystal structure prediction (CSP) methods has been held, with five target systems: a small nearly rigid molecule, a polymorphic former drug candidate, a chloride salt hydrate, a co-crystal and a bulky flexible molecule. This blind test has seen substantial growth in the number of participants, with the broad range of prediction methods giving a unique insight into the state of the art in the field. Significant progress has been seen in treating flexible molecules, usage of hierarchical approaches to ranking structures, the application of density-functional approximations, and the establishment of new workflows and 'best practices' for performing CSP calculations. All of the targets, apart from a single potentially disordered Z′ = 2 polymorph of the drug candidate, were predicted by at least one submission. Despite many remaining challenges, it is clear that CSP methods are becoming more applicable to a wider range of real systems, including salts, hydrates and larger flexible molecules. The results also highlight the potential for CSP calculations to complement and augment experimental studies of organic solid forms.The results of the sixth blind test of organic crystal structure prediction methods are presented and discussed, highlighting progress for salts, hydrates and bulky flexible molecules, as well as on-going challenges.",

keywords = "Cambridge Structural Database, crystal structure prediction, lattice energies, polymorphism",

author = "Reilly, {Anthony M.} and Cooper, {Richard I.} and Adjiman, {Claire S.} and Saswata Bhattacharya and Boese, {A. Daniel} and Brandenburg, {Jan Gerit} and Bygrave, {Peter J.} and Rita Bylsma and Campbell, {Josh E.} and Roberto Car and Case, {David H.} and Renu Chadha and Cole, {Jason C.} and Katherine Cosburn and Cuppen, {Herma M.} and Farren Curtis and Day, {Graeme M.} and DiStasio, {Robert A.} and Alexander Dzyabchenko and {Van Eijck}, {Bouke P.} and Elking, {Dennis M.} and {Van Den Ende}, {Joost A.} and Facelli, {Julio C.} and Ferraro, {Marta B.} and Laszlo Fusti-Molnar and Gatsiou, {Christina Anna} and Gee, {Thomas S.} and {De Gelder}, Ren{\'e} and Ghiringhelli, {Luca M.} and Hitoshi Goto and Stefan Grimme and Rui Guo and Hofmann, {Detlef W.M.} and Johannes Hoja and Hylton, {Rebecca K.} and Luca Iuzzolino and Wojciech Jankiewicz and {De Jong}, {Dani{\"e}l T.} and John Kendrick and {De Klerk}, {Niek J.J.} and Ko, {Hsin Yu} and Kuleshova, {Liudmila N.} and Xiayue Li and Sanjaya Lohani and Leusen, {Frank J.J.} and Lund, {Albert M.} and Jian Lv and Yanming Ma and Noa Marom and Masunov, {Art{\"e}m E.} and Patrick McCabe and McMahon, {David P.} and Hugo Meekes and Metz, {Michael P.} and Misquitta, {Alston J.} and Sharmarke Mohamed and Bartomeu Monserrat and Needs, {Richard J.} and Neumann, {Marcus A.} and Jonas Nyman and Shigeaki Obata and Harald Oberhofer and Oganov, {Artem R.} and Orendt, {Anita M.} and Pagola, {Gabriel I.} and Pantelides, {Constantinos C.} and Pickard, {Chris J.} and Rafal Podeszwa and Price, {Louise S.} and Price, {Sarah L.} and Angeles Pulido and Read, {Murray G.} and Karsten Reuter and Elia Schneider and Christoph Schober and Shields, {Gregory P.} and Pawanpreet Singh and Sugden, {Isaac J.} and Krzysztof Szalewicz and Taylor, {Christopher R.} and Alexandre Tkatchenko and Tuckerman, {Mark E.} and Francesca Vacarro and Manolis Vasileiadis and Alvaro Vazquez-Mayagoitia and Leslie Vogt and Yanchao Wang and Watson, {Rona E.} and {De Wijs}, {Gilles A.} and Jack Yang and Qiang Zhu and Groom, {Colin R.}",

note = "Publisher Copyright: {\textcopyright} Anthony M. Reilly et al. 2016.",

year = "2016",

month = aug,

day = "1",

doi = "10.1107/S2052520616007447",

language = "English (US)",

volume = "72",

pages = "439--459",

journal = "Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials",

issn = "2052-5192",

publisher = "John Wiley and Sons Inc.",

number = "4",

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TY - JOUR

T1 - Report on the sixth blind test of organic crystal structure prediction methods

AU - Reilly, Anthony M.

AU - Cooper, Richard I.

AU - Adjiman, Claire S.

AU - Bhattacharya, Saswata

AU - Boese, A. Daniel

AU - Brandenburg, Jan Gerit

AU - Bygrave, Peter J.

AU - Bylsma, Rita

AU - Campbell, Josh E.

AU - Car, Roberto

AU - Case, David H.

AU - Chadha, Renu

AU - Cole, Jason C.

AU - Cosburn, Katherine

AU - Cuppen, Herma M.

AU - Curtis, Farren

AU - Day, Graeme M.

AU - DiStasio, Robert A.

AU - Dzyabchenko, Alexander

AU - Van Eijck, Bouke P.

AU - Elking, Dennis M.

AU - Van Den Ende, Joost A.

AU - Facelli, Julio C.

AU - Ferraro, Marta B.

AU - Fusti-Molnar, Laszlo

AU - Gatsiou, Christina Anna

AU - Gee, Thomas S.

AU - De Gelder, René

AU - Ghiringhelli, Luca M.

AU - Goto, Hitoshi

AU - Grimme, Stefan

AU - Guo, Rui

AU - Hofmann, Detlef W.M.

AU - Hoja, Johannes

AU - Hylton, Rebecca K.

AU - Iuzzolino, Luca

AU - Jankiewicz, Wojciech

AU - De Jong, Daniël T.

AU - Kendrick, John

AU - De Klerk, Niek J.J.

AU - Ko, Hsin Yu

AU - Kuleshova, Liudmila N.

AU - Li, Xiayue

AU - Lohani, Sanjaya

AU - Leusen, Frank J.J.

AU - Lund, Albert M.

AU - Lv, Jian

AU - Ma, Yanming

AU - Marom, Noa

AU - Masunov, Artëm E.

AU - McCabe, Patrick

AU - McMahon, David P.

AU - Meekes, Hugo

AU - Metz, Michael P.

AU - Misquitta, Alston J.

AU - Mohamed, Sharmarke

AU - Monserrat, Bartomeu

AU - Needs, Richard J.

AU - Neumann, Marcus A.

AU - Nyman, Jonas

AU - Obata, Shigeaki

AU - Oberhofer, Harald

AU - Oganov, Artem R.

AU - Orendt, Anita M.

AU - Pagola, Gabriel I.

AU - Pantelides, Constantinos C.

AU - Pickard, Chris J.

AU - Podeszwa, Rafal

AU - Price, Louise S.

AU - Price, Sarah L.

AU - Pulido, Angeles

AU - Read, Murray G.

AU - Reuter, Karsten

AU - Schneider, Elia

AU - Schober, Christoph

AU - Shields, Gregory P.

AU - Singh, Pawanpreet

AU - Sugden, Isaac J.

AU - Szalewicz, Krzysztof

AU - Taylor, Christopher R.

AU - Tkatchenko, Alexandre

AU - Tuckerman, Mark E.

AU - Vacarro, Francesca

AU - Vasileiadis, Manolis

AU - Vazquez-Mayagoitia, Alvaro

AU - Vogt, Leslie

AU - Wang, Yanchao

AU - Watson, Rona E.

AU - De Wijs, Gilles A.

AU - Yang, Jack

AU - Zhu, Qiang

AU - Groom, Colin R.

PY - 2016/8/1

Y1 - 2016/8/1

N2 - The sixth blind test of organic crystal structure prediction (CSP) methods has been held, with five target systems: a small nearly rigid molecule, a polymorphic former drug candidate, a chloride salt hydrate, a co-crystal and a bulky flexible molecule. This blind test has seen substantial growth in the number of participants, with the broad range of prediction methods giving a unique insight into the state of the art in the field. Significant progress has been seen in treating flexible molecules, usage of hierarchical approaches to ranking structures, the application of density-functional approximations, and the establishment of new workflows and 'best practices' for performing CSP calculations. All of the targets, apart from a single potentially disordered Z′ = 2 polymorph of the drug candidate, were predicted by at least one submission. Despite many remaining challenges, it is clear that CSP methods are becoming more applicable to a wider range of real systems, including salts, hydrates and larger flexible molecules. The results also highlight the potential for CSP calculations to complement and augment experimental studies of organic solid forms.The results of the sixth blind test of organic crystal structure prediction methods are presented and discussed, highlighting progress for salts, hydrates and bulky flexible molecules, as well as on-going challenges.

AB - The sixth blind test of organic crystal structure prediction (CSP) methods has been held, with five target systems: a small nearly rigid molecule, a polymorphic former drug candidate, a chloride salt hydrate, a co-crystal and a bulky flexible molecule. This blind test has seen substantial growth in the number of participants, with the broad range of prediction methods giving a unique insight into the state of the art in the field. Significant progress has been seen in treating flexible molecules, usage of hierarchical approaches to ranking structures, the application of density-functional approximations, and the establishment of new workflows and 'best practices' for performing CSP calculations. All of the targets, apart from a single potentially disordered Z′ = 2 polymorph of the drug candidate, were predicted by at least one submission. Despite many remaining challenges, it is clear that CSP methods are becoming more applicable to a wider range of real systems, including salts, hydrates and larger flexible molecules. The results also highlight the potential for CSP calculations to complement and augment experimental studies of organic solid forms.The results of the sixth blind test of organic crystal structure prediction methods are presented and discussed, highlighting progress for salts, hydrates and bulky flexible molecules, as well as on-going challenges.

KW - Cambridge Structural Database

KW - crystal structure prediction

KW - lattice energies

KW - polymorphism

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DO - 10.1107/S2052520616007447

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JO - Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials

JF - Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials

IS - 4

ER -

Report on the sixth blind test of organic crystal structure prediction methods

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