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An Intramolecular OH···#(arene) Interaction in a BINOL-Phenazine Cocrystal with a ‘Free’ N-Atom Katherine Peterson, Rodger F. Henry, Geoff G.Z. Zhang, and Leonard R. MacGillivray Cryst. Growth Des., Just Accepted Manuscript • DOI: 10.1021/acs.cgd.8b00199 • Publication Date (Web): 05 Jun 2018 Downloaded from http://pubs.acs.org on June 5, 2018
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Crystal Growth & Design
An Intramolecular OH···π(arene) Interaction in a BINOLPhenazine Cocrystal with a ‘Free’ N-Atom Katherine E. Peterson,a,b Rodger F. Henry,a Geoff G. Z. Zhang*a and Leonard R. MacGillivray*b a Research
and Development, AbbVie, Inc., North Chicago, Illinois, USA 60064.
b Department
of Chemistry, University of Iowa, Iowa City, Iowa, USA 52242.
Electronic supplementary information is available. We report the occurrence of the hydrogen-bond-donor molecule 1,1’-binaphthyl-2,2’-diol (BINOL) that in the presence of the appreciably strong hydrogen-bond-acceptor phenazine forms a cocrystal stabilized by weak OH···π (arene) interactions. We also present a survey of the Cambridge Structural Database involving BINOL that reveals a limited number of structures that demonstrate the presence of a hydrogen-bond-acceptor group viz-a-viz phenazine that does not participate in a traditional hydrogen bond with BINOL.
Introduction Non-conventional hydrogen bond (H-bond) formation is of considerable interest in fields such as supramolecular chemistry, biology, and medicine. Interests are based on the prominent roles H-bonds play in stabilizing structures of biomolecules.(1)(2) Investigations of relatively weak interactions such as CH···X,(3)(4)(5) CH···π(6),(7)(8) and OH···π(9),(10) have led to significant progress in understanding how weak noncovalent forces stabilize the organic solid state. The studies have, as a result, ultimately supported continued efforts to advance applications of supramolecular chemistry and crystal engineering. An area within the field of crystal engineering that has gained attention, and especially in the pharmaceutical industry, is cocrystallization. The desire to control material properties of Active Pharmaceutical Ingredients (APIs) is of considerable interest in pharmaceutical development. Cocrystallization has, thus, demonstrated an ability to exert control of properties of solid forms of APIs by improving solubility and dissolution rate,(11) stability,(12) and mechanical properties(13) by the formation of non-covalent interactions between complementary functional groups of different molecules. Intermolecular H-bonding has provided a foundation for cocrystal formation, and rational design of corresponding supramolecular synthons relies on levels of predictability of H-bonds through preferential interactions between relatively strong H-bond donors and acceptors as delineated by Etter(14) and Desiraju.(15) The concept of supramolecular hierarchy, a common approach to crystal
engineering, is defined by competing intermolecular interactions;(16) therefore, it is of critical interest when the preferential formation of a non-conventional H-bond interaction can be viewed as the stabilizing factor in a cocrystal, particularly in the presence of available and more traditional H-bond donor and/or acceptor groups. A general focus of our research is crystal engineering cocrystals and, in the current case, cocrystals of 1,1’binaphthyl-2,2’-diol (BINOL) (Scheme Scheme 1). 1 BINOL exhibits axial chirality, being commonly used as a chiral auxiliary in asymmetric organic syntheses.(17) An examination of crystal structures of both racemic (ref. code BIRKOC01) and enantiopure forms (ref. codes WANNII and UKILAC) of BINOL reveals the molecule to tend to form extended chains via intermolecular OH···O H-bonds. While the crystal data for racBINOL (1) was first reported by Gridunova et al. in 1982,(18) and additional structural details were provided by Mori, et al.(19) and Toda, et al.(20) several years later in 1993 and 1997, respectively, neither of the reports discuss the possibility of an intramolecular OH···π interaction between one of the hydroxyl substituents and adjacent binaphthyl ring (Fig. Fig. 1). Scheme 1. Rac-BINOL and enantiomers and phenazine
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OH OH
OH OH
N
N
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achieved using SHELX-97. Crystallographic data are available in the supplementary information. Single-crystal X-ray diffraction data were collected for (S-BINOL)·(phen) and are also available in the supplementary information. Survey of CSD. A survey of the CSD (version 5.39, May 2017) was performed with ConQuest (version 1.19). BINOL derivatives were defined as molecules with hydroxyl substituents at 2- and 2’- positions on respective binaphthyl rings while allowing for substitution at any or all other positions on ring system. All structures were targeted to satisfy: (a) crystallographic R-factor < 0.10, (b) no metal coordination, (c) 3D coordinates fully determined, (d) refined hydroxyl hydrogen atom positions, and (e) a contact distance of < 4.0 Å between each BINOL substituent and an intermolecular atom defined as any atom with an atomic mass less than Cl. Figure 1. Crystal structure of enantiopure R-Binol (WANNII) showing intramolecular OH···π (green) and intermolecular OH···O (blue) H-bonds.
Our research here focuses on the H-bonding preferences of BINOL upon addition of a second component through cocrystallization. More specifically, we describe a cocrystallization of enantiopure BINOL with the diazine phenazine that affords the 1:1 cocrystal (R-BINOL)·(phen) (where: phen = phenazine). In addition to a primary OH···N Hbond, we observe the second OH group of BINOL to participate in an intramolecular OH···π(arene) interaction versus a second OH···N H-bond with the second N-atom of phen. We also provide a comparison of the structure of (RBINOL)·(phen) to reported structures of pure BINOL and reported BINOL-based cocrystals from the Cambridge Structural Database (CSD). Our findings demonstrate that such a ‘free’ hydroxyl group for BINOL in both pure and cocrystal forms is rare among the known crystal structures, being observed in two percent (3 out of 134) of similar BINOLcontaining multi-component solids.
Experimental Section Preparation of Cocrystals. Cocrystals Enantiopure BINOL (> 99% ee.), phen (98%) and 2-propanol (HPLC grade, 99.9%) were used as received from Sigma-Aldrich®. Cocrystals of (RBINOL)·(phen) were obtained by dissolution of equimolar amounts of (R)-(+)-BINOL (50 mg) and phen (32 mg) in 2propanol (1 mL). Following slow evaporation, small rods of (RBINOL)·(phen) suitable for single-crystal X-ray diffraction formed. A corresponding cocrystal of (S-BINOL)·(phen) was also obtained and an X-ray crystal analysis confirmed a solid of opposite handedness. SingleSingle-Crystal XX-ray Diffraction. A single crystal of (RBINOL)·(phen) was individually mounted on MiTeGen mounts. Intensity data were collected on a Bruker APEX2 system. Data were collected at 100 K with graphite-monochromated Cu Kα radiation (λ = 1.54178 A). Data were obtained in four sets using omega–phi scans with omega steps of 0.5° and phi steps of 90°. A total of 1464 frames were collected. The data were processed using SaintPlus. Corrections for Lorentzpolarisation effects were applied. Absorption was negligible. All structures were solved using direct methods that yielded the non-hydrogen atoms. All hydrogen atoms were located in Fourier-difference electron density maps. All non-hydrogen atoms were refined anisotropically. Hydrogen atoms associated with carbon atoms were refined in geometrically constrained riding positions. Hydrogen atoms associated with oxygen atoms were included in the located positions and refined isotropically without constraints. Refinement was
Results and Discussion Structural Analysis of (R-BINOL)·(phen). BINOL)·(phen Single crystals of (RBINOL)·(phen) (Fig, Fig, 2) 2 crystallize as bright yellow rods in the chiral monoclinic space group P21 (Fig. Fig. 2a). The asymmetric unit contains one R-BINOL and one phen molecule that interact via an intermolecular O-H···N H-bond (Fig. Fig. 2b). The components assemble such that the phen molecule participates in a face-to-face π···π stacking interaction with one naphthyl ring of R-BINOL (R-BINOLcentroid - phencentroid: 3.84 Å; tilt angle: 22.6°). The assembly packs as a stacked chain along the crystallographic a-axis and exhibits herringbone packing within the ac-plane (Fig. Fig. 2c). A most notable feature of (R-BINOL)·(phen) is the presence of a ‘free’ hydroxyl group and N-atom of R-BINOL and phen, respectively. Both groups are typically considered relatively strong H-bond donors and acceptors, and it is generally accepted that strong H-bond donors will interact with strong H-bond acceptors in a solid.(12)(21) Strictly speaking, the guiding principle is not demonstrated by the components of (R-BINOL)·(phen). As will be discussed, the presence of a ‘free’ N-atom has been observed in phen-based cocrystals;(22)(23)(24) however, in all examples, there was a general lack, or deficiency, of more traditional H-bond donor groups to interact with a free N-atom.
(a)
(c)
A B (b)
c a Figure 2. Cocrystal (R-BINOL)·(phen): (a) optical micrograph of single crystals, (b) ORTEP perspective showing intermolecular O-H···N Hbond, and (c) discrete assemblies pack in a herringbone fashion.
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Crystal Growth & Design
Figure 4. Intramolecular BINOL)·(phen). Figure 3. (R-BINOL)·(phen) showing relative orientation of phen and R-BINOL (green), intramolecular O-H···π interaction (green), and intermolecular O-H···N interaction (blue).
The X-ray structure of (R-BINOL)·(phen) reveals the free hydroxyl group of BINOL to be oriented so as to participate in an intramolecular OH···π interaction with the adjoining naphthyl ring (Fig. Fig. 3). The ability of an aromatic π-ring system to function as a H-bond acceptor, and with hydroxyl groups as donors,(3)(4)(25),(26) is well established.(3),(27),(28),(29) For (R-BINOL)·(phen), the distance and angle parameters conform to metrics wherein a hydroxyl group is the donor to a π-system. Specifically, the H···π (centroid) separation (3.13 Å) lies well within the range of reported values of solids possessing an O-H···π interaction.(26) The H-atoms of the hydroxyl group were clearly visible in the final difference electron-density map. We note that the X-ray structure of (RBINOL)·(phen) was collected at low temperature and the hydroxyl H-atoms were successfully refined. The corresponding O-H···π (centroid) angle (138o) also falls within the reported range.(26) According to Malone,(26) intra- and intermolecular H-bonds wherein a π-system acts as the acceptor can be classified into five categories. The categories are based on the orientation of the donor H-atom to the π-ring system. The intramolecular O-H···π interaction present in (RBINOL)·(phen) is Type V according to the criteria of Malone. A Type V interaction involves off-centering of the H-atom with respect to the centroid of π-acceptor. The geometry of the Hatom relative to the centroid of the π-acceptor is defined by θ, which is the angle of the H-atom to the normal plane containing the π-acceptor (Fig. Fig. 4). Off-centering is, therefore, defined by θ < 90°. The θ value of 47.2o for (R-BINOL)·(phen) meets the criteria for the Type V O-H···π interaction. The Type V geometry is described as the most frequent geometry for an OH···π type interaction.(26) Structural analyses of R-BINOL and RacRac-BINOL The presence of the intramolecular H-bond in (R-BINOL)·(phen) prompted us to examine reported solid forms of BINOL (Fig Fig. Fig. 5). Specifically, we analyzed the existing crystallographic data of racemic BINOL (ref. code BIRKOC01) and the R-enantiomer of BINOL (ref. code WANNII). The assembly properties of both racemic and enantiopure BINOL are described as being stabilized by conventional intermolecular O-H···O H-bonds (Fig. Fig. 5 a, b).(18),(19),(20) As illustrated by the structure of R-BINOL (Fig. Fig. 5 b, c), the diol forms an extended chain sustained by OH···O forces.(19),(20) Thus, as a single component, BINOL utilizes all available hydroxyl groups in conventional H-bonds. Our analysis of the data, however, also shows that the O-H groups of each structure can be considered to also interact with the π-ring system in a Type V geometry.(26) The interaction is of a bifurcated type and, thus, more secondary to the primary O-H···O H-bond. A similar interaction has been reported in the case of the solid form of an ortho-phenylphenol (Table Table 1).(5)
O-H···π
interaction
in
(R-
Table 1. Metrics of O-H(hydroxyl)···π(naphthyl) forces present in (R-BINOL)·(phen) and forms of pure BINOL.
D (Å)
Type V H-bond(26)
d(Å)
θ (°)
α (°)
< 4.0
> 1.4
< 90
90 3 Å. These N-atoms tend to be described as “inactive”. (30),(31) Collectively, our observations are consistent with a ‘free’ Natom being present in (R-BINOL)·(phen). All available H-bond donor groups of molecules cocrystallized with phen participate in a conventional H-bond. This observation underscores the rarity of the H-bonding preference in (R-BINOL)·(phen). The lack of an appreciable interaction between the free N-atom of phen and the OH (hydroxyl) group of BINOL contrasts those guidelines to understand the supramolecular hierarchy of noncovalent bonds in organic solids.(33) The lack of the interaction in (RBINOL)·(phen) further attests to how intermolecular forces, molecular size, and conformation can compete to render the components of a cocrystal to not interact in more expected geometries.
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Bilton, C; Howard, A. K.; Madhavi, N. N. L.; Nangia, A.; Desiraju, G. R.; Allen, F. H.; Wilson, C. C. Crystal engineering in the gem-alkynol family: the key role of water in the structure of 2,3,5,6-tetrabromo-trans-1,4diethynyl-cyclohexa-2,5-diene-1,4-diol dihydrate determined by X-ray and neutron diffraction at 150K. Acta Cryst. Sect. B 2000, 2000 B56, 1071–1079.
(4)
Steiner, T. CHO Hydrogen bonding in crystals. Cryst. Rev. 1996, 1996 6, 1–57.
(5)
Desiraju, G. R.; Steiner, T. The Weak Hydrogen Bond in Structural Chemistry and Biology. 2001, 2001 Oxford University
Table 4 Multi-component solids of Phen from CSD.
No. of structures
Phen cocrystals
No. of structures with one or more ‘free’ N-atoms
79
20a
No. of structures with a ‘free’ Natom in a CH···N geometry
18
a
Phen-containing systems having one molecule of phen lying along a symmetry element, where neither N (atom) participated in a conventional Hbond interaction,(22),(32) were not included.
Press. (6)
Steinwender, E.; Lutz, E. T. G.; van der Maas, J. H.; Kanters, J. A. 2-Ethynyladamantan-2-ol: a model compound with distinct O-H···π and CH···O hydrogen bonds. Vib. Spect. 1993, 1993 4, 217–229.
(7)
Hirota, M.; Sakaibara, K.; Suezawa, H.; Yuzuri, T.; Ankai, E.; Nishio, M. Intramolecular CH···π interaction. Substituent effect as a probe for hydrogen bond-like character. J. Phys. Org. Chem. 2000, 2000 13, 620–623.
(8)
Farrugia, L. J.; Kocovský, P.; Senn, H. M.; Vyskocil, S. Weak intra- and intermolecular interactions in a binaphthol imine: an experimental charge-density study on (+)-8’benzhydrylideneamino-1,1’-binaphthyl-2-ol. Acta Cryst. Sect. B 2009, 2009 B56, 757–769.
(9)
Garcia, J. G.; Ramos, B.; Rodriguez, A. 1.1-Diphenyl-3propyn-1-ol. Acta Cryst. Sect. C 1995, 1995 C51, 2674–2676.
Conclusion We have reported an intramolecular O-H···π interaction in the cocrystal (R-BINOL)·(phen) that forms in the presence of a ‘free’ N-atom. The presence of such a hydroxyl group and a free N-atom in a solid is shown to be limited or rare. Our results underscore a need to be cognizant of the subtleties that define interactions of different molecules in crystals, particularly as related supramolecular synthesis and cocrystal formation. Studies are ongoing to further study BINOL and elucidate additional cocrystals that exhibit similar structural behaviors.
Supporting Information Electronic supplementary information (ESI) available: Single crystal X-ray diffraction data for (S-BINOL)·(phen), powder xray diffraction patterns for (S-BINOL)·(phen) and (RBINOL)·(phen) and preparation of (S-BINOL)·(phen) and (RBINOL)·(phen). For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c000000x/.
AUTHOR INFORMATION
(10) Steiner, T.; Starikov, E. B.; Tamm, M. Weak hydrogen
bonding. Part 3. A benzyl group accepting equally strong hydrogen bonds from O-H and C-H donors: 5-ethynyl-5Hdibenzo[a,d]cyclohepten-5-ol. J. Chem. Soc. Perkin Trans. 2 1996, 1996 67–71. (11) Lee, H.-G.; Zhang, G. G. Z.; Flanagan, D. R. Cocrystal
Corresponding Author E-mail:
[email protected]; Tel: +1 319-335-3504. E-mail:
[email protected]; Tel. +1 847-937-4702
Disclosure This study was funded by AbbVie. AbbVie participated in the study design, research, data collection, analysis and interpretation of data, as well as writing, reviewing, and approving the publication. Katherine Peterson is a former employee of AbbVie and a current student of the University of Iowa. Geoff Zhang and Rodger Henry are AbbVie employees and may own AbbVie stock/options. Dr. Leonard MacGillivray is a Professor of Chemistry at the University of Iowa and was involved in the study design, writing, reviewing, and approving the publication; he has not received personal compensation from AbbVie.
intrinsic dissolution behavior using a rotating disk. J. Pharm. Sci. 2011, 2011 100, 1736–1744. (12) Frišćić,
T.; Jones, W. Cocrystal architecture and properties: design and building of chiral and racemic structures by solid-solid reactions. Faraday Discuss. 2007, 2007 136, 167–178.
(13) Karki, S.; Frišćić, T.; Fábián, L.; Laity, P. R.; Day, G. M.;
Jones, W. Improving mechanical properties of crystalline solids by cocrystal formation: new compressible forms of paracetamol. Adv. Mat. 2009, 2009 21, 3905–3909. (14) Etter, M. C. Encoding and decoding hydrogen-bond patterns
of organic compounds. Acc. Chem. Res. 1990, 1990 23, 120–126. (15) Desiraju,
G. R. Surpamolecular synthons in crystal engineering—a new organic synthesis. Angew. Chem. Int. Ed. Engl. 1995, 1995 34, 2311–2327.
(16) Bućar, D.-K.; Henry, R. F.; Zhang, G. G. Z.; MacGillivray, L. R.
References (1)
Steiner, T.; Koellner, G. Hydrogen bonds with piacceptors in proteins: frequencies and role in stabilizing local 3D structures. J. Mol. Biol. 2001, 2001 305, 535–557.
(2)
Salonen, L. M.; Ellermann, M.; Diederich, F. Aromatic rings in chemical and biological recognition: energetics and structures. Angew. Chem. 2011, 2011 50, 4808–4842.
Synthon hierarchies in crystal forms composed of theophylline and hydroxybenzoic acids: cocrystal screening via solutionmediated phase transformation. Cryst. Growth Des. 2014, 2014 14, 5318–5328. (17) Brunel, J. M. BINOL: a versatile chiral reagent.
Chem.
Rev. 2007, 2007 107, PR1–PR45.
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(18) Gridunova, G. V.; Furmanova, N. G.; Shklover, V. E.;
(33) Bis, J. A.; Vishweshwar, P.; Weyna, D.; Zaworotko, M. J.
Struchkov, Y. T.; Ezhkova, Z. I.;Chayanov, B. A. Sov. Phys. Crystallogr. 1982, 1982 27, 290–294.
Hierarchy of supramolecular synthons: persistent hydroxyl···pyridine hydrogen bonds in cocrystal that contain a cyano acceptor. Mol. Pharm. 2007, 2007 4, 401– 416.
(19) Mori, K.; Masuda, Y.; Kashino, S. (+)-(R)- and racemic forms
of 2,2’-dihyroxy-1,1’-binaphthyl. Acta Cryst. Sect. C. 1993, 1993 C49, 1224–1227. (20) Toda, F.; Tanaka, K.; Miyamoto, H.; Koshima, H.; Miyahara, I.;
Hirotsu, K. Formation of racemic compound crystals by mixing of two enantiomeric crystals in the solid state. Liquid transport of molecules from crystal to crystal. J. Chem. Soc. Perkins Trans. 2 1997, 1997 1877–1885. (21) Schollmeyer, D.; Shishkin, O. V.; Ruhl, T.; Vysotsky, M.
O. O-H··· π and halogen ··· π interactions as driving forces in the crystal organisations of tri-bromo and tri-iodo trityl alcohols. CrystEngComm. 2008, 2008 10, 715–723. (22) Chakraborty, S.; Rajput, L.; Desiraju, G. R. Designing ternary
co-crystals with stacking interactions and weak hydrogen bonds. 4,4’-Bis-hydroxyazobenzene. Cryst. Growth Des. 2014, 2014 14, 2571–2577. (23) V. R. Thalladi, V. R; Smolka, T.;Boese, R.; Sustmann, R. T.
Reproducible phenazine molecular stacks. CrystEngComm., 2000, 2, 96–101. 2000 (24) SeethaLekshmi, S.; Varughese, S.; Giri, L.; Pedireddi, V.R.
Molecular complexes of 4-halophenylboronic acids: a systematic exploration of isostructurality and structural landscape. Cryst. Growth Des. 2014, 2014 14, 4143–4154. (25) Ferguson, G.; Gallagher, J. F.; Glidewell, C.; Zakaria, C. M.
O-H···π (arene) intermolecular hydrogen bonding in the structure of 1,1,2-triphenylethanol. Acta Cryst.Sect. C 1994, 1994 C50, 70–73. (26) Malone, J. F.; Murray, C. M.; Charlton, M. H.; Docherty, R.;
Lavery, A. J. X-H···π(phenyl) interactions. Theoretical and crystallographic observations. J. Chem. Soc., Faraday Trans. 1997, 1997 93, 3429–3436. (27) Etter,
M. C.; Reutzel, S. M. Hydrogen bond directed cocrystallization and molecular recognition properties of acyclic imides. J. Am. Chem. Soc. 1991, 1991 113, 2586–2598.
(28) Atwood, J. L.; Hamada, F.; Robinson, K. D.; Orr, G. W.;
Vincent, R. L. X-ray diffraction evidence for aromatic π hydrogen bonding to water. Nature (London) 1991, 1991 349, 683– 684. (29) Hanton, L. R.; Hunter, C. A.; Purvis, D. H. Structural
consequences of a molecular assembly that is deficient in hydrogen-bond acceptors. J. Chem. Soc. Chem. Commun. 1992, 1992 1134–1136. (30) Smolka, T.; Boese, R.; Sustmann, R. Design of a three
component crystal based on the cocrystal of phenazine and 2,2’-dihydroxybiphenyl. Structural Chemistry 1999, 1999 10, 429– 431. (31) Kumar, V. S. S.; Kuduva.S. S.; Desiraju,
G. R. 3,5Dinitrosalicylic acid-phenazine (1/1). Acta Cryst. Sect. E. 2002, 2002 E58, o865–o866.
(32) Men, Y.; Sun, J.; Huang, Z.; Zheng, Q. Rational construction
of 2D and 3D borromean arrayed organic crystals by hydrogen-bond-directed self-assembly. Angew. Chem. Int. Ed. Engl. 2009, 2009 48, 2873–2876.
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Table of Contents Graphic
A rare mix of hydrogen bonding is reported in a cocrystal based on BINOL.
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