Opening Pandora’s Box: Chirality, Polymorphism, and Stoichiometric Diversity in Flurbiprofen/Proline Cocrystals

Natalia Tumanova; Nikolay Tumanov; Koen Robeyns; Franziska Fischer; Luca Fusaro; Fabrice Morelle; Voraksmy Ban; Geoffroy Hautier; Yaroslav Filinchuk; Johan Wouters; Tom Leyssens; Franziska Emmerling

doi:10.1021/acs.cgd.7b01436

Opening Pandora’s Box: Chirality, Polymorphism, and Stoichiometric Diversity in Flurbiprofen/Proline Cocrystals

Natalia Tumanova, Nikolay Tumanov, Koen Robeyns, Franziska Fischer, Luca Fusaro, Fabrice Morelle, Voraksmy Ban, Geoffroy Hautier, Yaroslav Filinchuk, Johan Wouters, Tom Leyssens, Franziska Emmerling

Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

Résumé

Proline has been widely used for various cocrystallization applications, including pharmaceutical cocrystals. Combining enantiopure and racemic flurbiprofen and proline, we discovered 18 new crystal structures. Liquid-assisted grinding proved highly efficient to explore all the variety of crystal forms. A unique combination of state-of-the-art characterization techniques, comprising variable temperature in situ X-ray diffraction and in situ ball-milling, along with other physicochemical methods and density functional theory calculations, was indispensable for identifying all the phases. Analyzing the results of in situ ball-milling, we established a stepwise mechanism for the formation of several 1:1 cocrystals via an intermediate 2:1 phase. The nature of the solvent in liquid-assisted grinding was found to significantly affect the reaction rate and, in some cases, the reaction pathway.

langue originale	Anglais
Pages (de - à)	954-961
Nombre de pages	8
journal	Crystal Growth and Design
Volume	18
Numéro de publication	2
Les DOIs	https://doi.org/10.1021/acs.cgd.7b01436 https://doi.org/10.1021/acs.cgd.7b01436
Etat de la publication	Publié - 4 janv. 2018

Financement

Bailleurs de fonds	Numéro du bailleur de fonds
CISM
European Cooperation in Science and Technology	CM1402
European Synchrotron Radiation Facility
Fonds De La Recherche Scientifique - FNRS
Fonds pour la Formation à la Recherche dans l'Industrie et l'Agriculture
Paul Scherrer Institut
Université Catholique de Louvain

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Autres fichiers et liens

Link to publication in Scopus

Physico-chimie et caractérisation (PC2)
Wouters, J. (!!Manager), Aprile, C. (!!Manager) & Fusaro, L. (!!Manager)
Plateforme technologique Caracterisation physico-chimiques
Equipement/installations: Plateforme technolgique
Plateforme Technologique Calcul Intensif
Champagne, B. (!!Manager)
Plateforme technologique Calcul intensif
Equipement/installations: Plateforme technolgique

CCDC 1537421: Experimental Crystal Structure Determination
Tumanova, N. (Contributeur), Tumanov, N. (Contributeur), Robeyns, K. (Contributeur), Fischer, F. (Contributeur), Fusaro, L. (Contributeur), Morelle, F. (Contributeur), Ban, V. (Contributeur), Hautier, G. (Contributeur), Filinchuk, Y. (Contributeur), Wouters, J. (Contributeur), Leyssens, T. (Contributeur) & Emmerling, F. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2018
DOI: 10.5517/ccdc.csd.cc1nlt79, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1nlt79&sid=DataCite
Ensemble de données
CCDC 1537416: Experimental Crystal Structure Determination
Tumanova, N. (Contributeur), Tumanov, N. (Contributeur), Robeyns, K. (Contributeur), Fischer, F. (Contributeur), Fusaro, L. (Contributeur), Morelle, F. (Contributeur), Ban, V. (Contributeur), Hautier, G. (Contributeur), Filinchuk, Y. (Contributeur), Wouters, J. (Contributeur), Leyssens, T. (Contributeur) & Emmerling, F. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2018
DOI: 10.5517/ccdc.csd.cc1nlt24, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1nlt24&sid=DataCite
Ensemble de données
CCDC 1537410: Experimental Crystal Structure Determination
Tumanova, N. (Contributeur), Tumanov, N. (Contributeur), Robeyns, K. (Contributeur), Fischer, F. (Contributeur), Fusaro, L. (Contributeur), Morelle, F. (Contributeur), Ban, V. (Contributeur), Hautier, G. (Contributeur), Filinchuk, Y. (Contributeur), Wouters, J. (Contributeur), Leyssens, T. (Contributeur) & Emmerling, F. (Contributeur), Cambridge Crystallographic Data Centre, 1 janv. 2018
DOI: 10.5517/ccdc.csd.cc1nlswx, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1nlswx&sid=DataCite
Ensemble de données

Contient cette citation

Tumanova, N., Tumanov, N., Robeyns, K., Fischer, F., Fusaro, L., Morelle, F., Ban, V., Hautier, G., Filinchuk, Y., Wouters, J., Leyssens, T., & Emmerling, F. (2018). Opening Pandora’s Box: Chirality, Polymorphism, and Stoichiometric Diversity in Flurbiprofen/Proline Cocrystals. Crystal Growth and Design, 18(2), 954-961. https://doi.org/10.1021/acs.cgd.7b01436, https://doi.org/10.1021/acs.cgd.7b01436

@article{65e1fe7c8ee24e958accef2cd0a636d1,

title = "Opening Pandora{\textquoteright}s Box: Chirality, Polymorphism, and Stoichiometric Diversity in Flurbiprofen/Proline Cocrystals",

abstract = "Proline has been widely used for various cocrystallization applications, including pharmaceutical cocrystals. Combining enantiopure and racemic flurbiprofen and proline, we discovered 18 new crystal structures. Liquid-assisted grinding proved highly efficient to explore all the variety of crystal forms. A unique combination of state-of-the-art characterization techniques, comprising variable temperature in situ X-ray diffraction and in situ ball-milling, along with other physicochemical methods and density functional theory calculations, was indispensable for identifying all the phases. Analyzing the results of in situ ball-milling, we established a stepwise mechanism for the formation of several 1:1 cocrystals via an intermediate 2:1 phase. The nature of the solvent in liquid-assisted grinding was found to significantly affect the reaction rate and, in some cases, the reaction pathway.",

author = "Natalia Tumanova and Nikolay Tumanov and Koen Robeyns and Franziska Fischer and Luca Fusaro and Fabrice Morelle and Voraksmy Ban and Geoffroy Hautier and Yaroslav Filinchuk and Johan Wouters and Tom Leyssens and Franziska Emmerling",

note = "Funding Information: The authors thank UCL, FNRS, FRIA (scholarship allocated to N.T.), and COST Action (CM1402) for the financial support; PC2 platform (UNamur) for the equipment; ESRF, PSI, and BESSY II for the beam time; Dr. D. Waroquiers, Dr. G. Yu, Prof. R. Cerny, Prof. J. van de Streek, L. Baulard, and P. Van Velthem for their help and advice; and CISM/UCL and C{\'E}CI for providing computational resources. Funding Information: The authors thank UCL, FNRS, FRIA (scholarship allocated to N.T.), and COST Action (CM1402) for the financial support; PC2 platform (UNamur) for the equipment; ESRF, PSI, and BESSY II for the beam time; Dr. D. Waroquiers, Dr. G. Yu, Prof. R. Cerny, Prof. J. van de Streek L. Baulard, and P. Van Velthem for their help and advice; and CISM/UCL and CECI for providing computational resources. Publisher Copyright: {\textcopyright} 2018 American Chemical Society. Copyright: Copyright 2021 Elsevier B.V., All rights reserved.",

year = "2018",

month = jan,

day = "4",

doi = "10.1021/acs.cgd.7b01436",

language = "English",

volume = "18",

pages = "954--961",

journal = "Crystal Growth and Design",

issn = "1528-7483",

publisher = "American Chemical Society",

number = "2",

}

Tumanova, N, Tumanov, N, Robeyns, K, Fischer, F, Fusaro, L, Morelle, F, Ban, V, Hautier, G, Filinchuk, Y, Wouters, J, Leyssens, T & Emmerling, F 2018, 'Opening Pandora’s Box: Chirality, Polymorphism, and Stoichiometric Diversity in Flurbiprofen/Proline Cocrystals', Crystal Growth and Design, VOL. 18, Numéro 2, p. 954-961. https://doi.org/10.1021/acs.cgd.7b01436, https://doi.org/10.1021/acs.cgd.7b01436

TY - JOUR

T1 - Opening Pandora’s Box

T2 - Chirality, Polymorphism, and Stoichiometric Diversity in Flurbiprofen/Proline Cocrystals

AU - Tumanova, Natalia

AU - Tumanov, Nikolay

AU - Robeyns, Koen

AU - Fischer, Franziska

AU - Fusaro, Luca

AU - Morelle, Fabrice

AU - Ban, Voraksmy

AU - Hautier, Geoffroy

AU - Filinchuk, Yaroslav

AU - Wouters, Johan

AU - Leyssens, Tom

AU - Emmerling, Franziska

N1 - Funding Information: The authors thank UCL, FNRS, FRIA (scholarship allocated to N.T.), and COST Action (CM1402) for the financial support; PC2 platform (UNamur) for the equipment; ESRF, PSI, and BESSY II for the beam time; Dr. D. Waroquiers, Dr. G. Yu, Prof. R. Cerny, Prof. J. van de Streek, L. Baulard, and P. Van Velthem for their help and advice; and CISM/UCL and CÉCI for providing computational resources. Funding Information: The authors thank UCL, FNRS, FRIA (scholarship allocated to N.T.), and COST Action (CM1402) for the financial support; PC2 platform (UNamur) for the equipment; ESRF, PSI, and BESSY II for the beam time; Dr. D. Waroquiers, Dr. G. Yu, Prof. R. Cerny, Prof. J. van de Streek L. Baulard, and P. Van Velthem for their help and advice; and CISM/UCL and CECI for providing computational resources. Publisher Copyright: © 2018 American Chemical Society. Copyright: Copyright 2021 Elsevier B.V., All rights reserved.

PY - 2018/1/4

Y1 - 2018/1/4

N2 - Proline has been widely used for various cocrystallization applications, including pharmaceutical cocrystals. Combining enantiopure and racemic flurbiprofen and proline, we discovered 18 new crystal structures. Liquid-assisted grinding proved highly efficient to explore all the variety of crystal forms. A unique combination of state-of-the-art characterization techniques, comprising variable temperature in situ X-ray diffraction and in situ ball-milling, along with other physicochemical methods and density functional theory calculations, was indispensable for identifying all the phases. Analyzing the results of in situ ball-milling, we established a stepwise mechanism for the formation of several 1:1 cocrystals via an intermediate 2:1 phase. The nature of the solvent in liquid-assisted grinding was found to significantly affect the reaction rate and, in some cases, the reaction pathway.

AB - Proline has been widely used for various cocrystallization applications, including pharmaceutical cocrystals. Combining enantiopure and racemic flurbiprofen and proline, we discovered 18 new crystal structures. Liquid-assisted grinding proved highly efficient to explore all the variety of crystal forms. A unique combination of state-of-the-art characterization techniques, comprising variable temperature in situ X-ray diffraction and in situ ball-milling, along with other physicochemical methods and density functional theory calculations, was indispensable for identifying all the phases. Analyzing the results of in situ ball-milling, we established a stepwise mechanism for the formation of several 1:1 cocrystals via an intermediate 2:1 phase. The nature of the solvent in liquid-assisted grinding was found to significantly affect the reaction rate and, in some cases, the reaction pathway.

UR - https://www.scopus.com/pages/publications/85041915775

U2 - 10.1021/acs.cgd.7b01436

DO - 10.1021/acs.cgd.7b01436

M3 - Article

SN - 1528-7483

VL - 18

SP - 954

EP - 961

JO - Crystal Growth and Design

JF - Crystal Growth and Design

IS - 2

ER -

Opening Pandora’s Box: Chirality, Polymorphism, and Stoichiometric Diversity in Flurbiprofen/Proline Cocrystals

Résumé

Financement

Accès au document

Autres fichiers et liens

Empreinte digitale

Équipement

Physico-chimie et caractérisation (PC2)

Plateforme Technologique Calcul Intensif

Ensembles de données

CCDC 1537421: Experimental Crystal Structure Determination

CCDC 1537416: Experimental Crystal Structure Determination

CCDC 1537410: Experimental Crystal Structure Determination

Contient cette citation