Expanding the Supramolecular Toolkit: Computed Molecular and Crystal Properties for Supporting the Crystal Engineering of Higher-Order Molecular Ionic Cocrystals

被引:9
作者
Alkhidir, Tamador [1 ]
Saeed, Zeinab M. [1 ]
Shunnar, Abeer F. [1 ]
Abujami, Eman [1 ]
Nyadzayo, Runyararo M. [1 ]
Dhokale, Bhausaheb [1 ]
Mohamed, Sharmarke [1 ]
机构
[1] Khalifa Univ Sci & Technol, Green Chem & Mat Modelling Lab, Dept Chem, Abu Dhabi, U Arab Emirates
关键词
TOTAL-ENERGY CALCULATIONS; PYRIDINE HYDROGEN-BONDS; TERNARY COCRYSTALS; CHARGE-TRANSFER; HIERARCHY; SYNTHONS; SALTS; CONTAIN; SOLIDS; ACID;
D O I
10.1021/acs.cgd.1c01107
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Over the past 2 decades, significant progress has been made in developing a robust supramolecular toolkit for the crystal engineering of simple binary cocrystals. By contrast, crystal engineering of higher-order molecular ionic cocrystals (ICCs) is not well established. Her; we report the results of the most extensive survey of the molecular and crystal properties of ICCs reported to date and use the resulting data to propose a set of guiding principles to aid the crystallization of molecular ICCs sustained by charge-assisted hydrogen bonding interactions. Using a data set comprising a total of 94 ICC crystal structures, this work reveals that molecular ICCs are favored within a narrow range of the property landscape. Specifically, most of the ICCs in the data set are crystallized using molecules with significantly different polar surface areas. The data also highlight the importance of choosing molecules with a similar number of conformational degrees of freedom when targeting higher-order cocrystals. Molecular ICCs comprising conjugate acid-base fragments are more likely to be observed in crystallization screens when the difference in the ionization constants of the acid-base pair lie within the "gray" zone of the salt-cocrystal continuum. This work also reveals the hierarchy in the supramolecular heterosynthons of molecular ICCs. Finally, periodic dispersion-corrected density functional theory calculations on a limited subset of crystal structures reveals that most of the ICCs surveyed are driven to form on the basis of favorable energetics as indicated by a mean stabilization energy of -5 kJ mol(-1).
引用
收藏
页码:485 / 496
页数:12
相关论文
共 53 条
[1]   Constructing, deconstructing, and reconstructing ternary supermolecules [J].
Aakeroey, Christer B. ;
Desper, John ;
Smith, Michelle M. .
CHEMICAL COMMUNICATIONS, 2007, (38) :3936-3938
[2]   Building co-crystals with molecular sense and supramolecular sensibility [J].
Aakeröy, CB ;
Salmon, DJ .
CRYSTENGCOMM, 2005, 7 :439-448
[3]  
[Anonymous], 2020, MARVINSKETCH V20 21
[4]  
[Anonymous], 2020, MARVIN WAS USED DRAW
[5]   A Prolific Solvate Former, Galunisertib, under the Pressure of Crystal Structure Prediction, Produces Ten Diverse Polymorphs [J].
Bhardwaj, Rajni M. ;
McMahon, Jennifer A. ;
Nyman, Jonas ;
Price, Louise S. ;
Konar, Sumit ;
Oswald, Iain D. H. ;
Pulham, Colin R. ;
Price, Sarah L. ;
Reutzel-Edens, Susan M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (35) :13887-13897
[6]   Hierarchy of supramolecular synthons:: Persistent hydroxyl•••pyridine hydrogen bonds in cocrystals that contain a cyano acceptor [J].
Bis, Joanna A. ;
Vishweshwar, Peddy ;
Weyna, David ;
Zaworotko, Michael J. .
MOLECULAR PHARMACEUTICS, 2007, 4 (03) :401-416
[7]   CIF2Cell: Generating geometries for electronic structure programs [J].
Bjorkman, Torbjorn .
COMPUTER PHYSICS COMMUNICATIONS, 2011, 182 (05) :1183-1186
[8]   Organic-inorganic ionic co-crystals: a new class of multipurpose compounds [J].
Braga, Dario ;
Grepioni, Fabrizia ;
Shemchuk, Oleksii .
CRYSTENGCOMM, 2018, 20 (16) :2212-2220
[9]   From unexpected reactions to a new family of ionic co-crystals: the case of barbituric acid with alkali bromides and caesium iodide [J].
Braga, Dario ;
Grepioni, Fabrizia ;
Maini, Lucia ;
Prosperi, Susanna ;
Gobetto, Roberto ;
Chierotti, Michele R. .
CHEMICAL COMMUNICATIONS, 2010, 46 (41) :7715-7717
[10]   Complex Polymorphic System of Gallic Acid-Five Monohydrates, Three Anhydrates, and over 20 Solvates [J].
Braun, Doris E. ;
Bhardwaj, Rajni M. ;
Florence, Alastair J. ;
Tocher, Derek A. ;
Price, Sarah L. .
CRYSTAL GROWTH & DESIGN, 2013, 13 (01) :19-23