Method Article

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

DOI:

10.3791/53418

⸱

February 15th, 2016

 ,  ,  ,  ,  ,  , 
1Department of Material and Life Science, Graduate School of Engineering, Osaka University

In This Article

Summary

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This article describes construction of a series of hydrogen-bonding supramolecular clusters in crystals using primary ammonium triphenylacetates, which are recrystallized from non-polar solvents. This selective construction of the supramolecular clusters leads to effective systematical symmetric studies about a correlation between the supramolecular clusters and their components.

Abstract

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Functions of clusters in nano or sub-nano scale significantly depend on not only kinds of their components but also arrangements, or symmetry, of their components. Therefore, the arrangements in the clusters have been precisely characterized, especially for metal complexes. Contrary to this, characterizations of molecular arrangements in supramolecular clusters composed of organic molecules are limited to a few cases. This is because construction of the supramolecular clusters, especially obtaining a series of the supramolecular clusters, is difficult due to low stability of non-covalent bonds compare to covalent bonds. From this viewpoint, utilization of organic salts is one of the most useful strategies. A series of the supramolecules could be constructed by combinations of a specific organic molecule with various counter ions. Especially, primary ammonium carboxylates are suitable as typical examples of supramolecules because various kinds of carboxylic acids and primary amines are commercially available, and it is easy to change their combinations. Previously, it was demonstrated that primary ammonium triphenylacetates using various kinds of primary amines specifically construct supramolecular clusters, which are composed of four ammoniums and four triphenylacetates assembled by charge-assisted hydrogen bonds, in crystals obtained from non-polar solvents. This study demonstrates an application of the specific construction of the supramolecular clusters as a strategy to conduct systematical symmetric study for clarification of correlations between molecular arrangements in supramolecules and kinds and numbers of their components. In the same way with binary salts composed of triphenylacetates and one kind of primary ammoniums, ternary organic salts composed of triphenylacetates and two kinds of ammoniums construct the supramolecular clusters, affording a series of the supramolecular clusters with various kinds and numbers of the components.

Introduction

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Supramolecules are fascinating and important research targets because of their unique functions, such as construction of supramolecular architectures, sensing of ions and/or molecules, and chiral separations, originated from their molecular recognition abilities using flexible non-covalent bonds1-11. In molecular recognitions, symmetry of supramolecular assemblies is one of the most important factors. Despite the importance, it is still difficult to design supramolecules with desired symmetries due to flexibility in numbers and kinds of the components as well as angles and distances of non-covalent bonds.

Clarification of correlations between symmetries of supramolecules and their components based on systematical studies is useful strategy to achieve construction of desired supramolecules. For this purpose, supramolecular clusters were selected as research targets because they are composed of limited number of components and are evaluable theoretically12-14. However, contrary to metal complexes, there are a limited number of reports constructing supramolecular clusters due to low stability of non-covalent bonds for sustaining the supramolecular structures15,16. This low stability also becomes a problem in obtaining a series of supramolecular assemblies which have the same kinds of structures. In this study, charge-assisted hydrogen bonds of organic salts, which are one of the most robust non-covalent bonds17-20, are mainly employed to construct specific supramolecular assemblies preferentially21-32. It is also noteworthy that organic salts are composed of acids and bases, and thus numerous kinds of organic salts are easily obtained just by mixing different combinations of acids and bases. Especially, organic salts are useful for systematic studies because combinations of a specific component with various kinds of counter ions result in the same types of supramolecular assemblies. Therefore, it is possible to compare structural differences of supramolecular assemblies based on kinds of counter ions.

In previous works, supramolecules with 0-dimensional (0-D), 1-dimensional (1-D), and 2-dimensional (2-D) hydrogen-bonding networks by primary ammonium carboxylates were confirmed and characterized from a viewpoint of chirality32. These multi-dimensional supramolecules are important research targets in hierarchical crystal design27 as well as applications exploiting their dimensionality. In addition, characterization of the hydrogen-bonding networks would give important knowledge about roles of biological molecules because all of amino acids have ammonium and carboxylic groups. Providing guidelines to obtain these supramolecules separately gives them further opportunities in applications. In these supramolecules, construction of supramolecular clusters with 0-D hydrogen-bonding networks is relatively difficult as demonstrated in statistical study28. However, after clarification of factors for constructing the supramolecular clusters, they were selectively constructed, and a series of the supramolecular clusters was obtained21-25,32. These works make it possible to conduct systematical symmetric study on the supramolecular clusters to clarify component-dependent symmetric characteristics of the supramolecular clusters. For this purpose, the supramolecular clusters of primary ammonium triphenylacetates have interesting features, that is, their topological variety in hydrogen-bonding networks24,32, which would reflect their symmetric features as well as chiral conformations of the component trityl groups (Figure 1a and 1b). Here methodologies for constructing a series of supramolecular clusters using primary ammonium triphenylacetates and for characterizing symmetric features of the supramolecular clusters are demonstrated. Keys for the construction of the supramolecular clusters are introduction of bulky trityl groups and recrystallization of the organic salts from non-polar solvents. Binary and ternary primary ammonium triphenylacetates were prepared for the construction of the supramolecular clusters. Crystallographic studies from viewpoints of topologies of the hydrogen-bonding networks24,32, topographies (conformations) of trityl groups33,34, and molecular arrangements as analogues of octacoordinated polyhedrons12 (Figure 1c) revealed component-dependent symmetric characteristics of the supramolecular clusters25.

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Protocol

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1. Preparation of Single Crystals Composed of Primary Ammonium Triphenylacetates

  1. Prepare organic salts, primary ammonium triphenylacetates (Figure 1a).
    1. Dissolve triphenylacetic acid (TPAA, 0.10 g, 0.35 mmol) and primary amine: n-butylamine (nBu, 2.5 x 10-2 g, 0.35 mmol), isobutylamine (isoBu, 2.5 x 10-2 g, 0.35 mmol), t-butylamine (tBu, 2.5 x 10-2 g, 0.35 mmol), or t-amylamine (tAm, 3.0 x 10-2 g, 0.35 mmol), together in methanol (20 ml) in TPAA : amine = 1:1 molar ratio for preparation of binary organic salts.
    2. In the case of ternary organic salts, dissolve TPAA (0.10 g, 0.35 mmol) and two kinds of primary amines: nBu (1.3 x 10-2 g, 0.17 mmol)-tBu (1.3 x 10-2 g, 0.17 mmol), nBu (1.3 x 10-2 g, 0.17 mmol)-tAm (1.5 x 10-2 g, 0.17 mmol), isoBu (1.3 x 10-2 g, 0.17 mmol)-tBu (1.3 x 10-2 g, 0.17 mmol), or isoBu (1.3 x 10-2 g, 0.17 mmol)-tAm (1.5 x 10-2 g, 0.17 mmol), together in methanol (20 ml) in TPAA : amine-1 : amine-2 = 2:1:1.
    3. Evaporate all of the solutions by rotary evaporators (40 °C, 200 Torr), affording organic salts: TPAA-nBu, TPAA-isoBu, TPAA-tBu, TPAA-tAm, TPAA-nBu-tBu, TPAA-nBu-tAm, TPAA-isoBu-tBu, and TPAA-isoBu-tAm.
  2. Prepare single crystals composed of supramolecular clusters.
    1. Dissolve each of the organic salts (5.0 mg) in a glass vial in toluene (0.30 ml) as a non-polar good solvent, which was selected because the supramolecular clusters are preferably constructed in non-polar environment. For the organic salts TPAA-tBu, TPAA-tAm, TPAA-isoBu-tBu, and TPAA-isoBu-tAm, heat toluene up to 40 °C to dissolve them.
    2. Add hexane: 0.5 ml, 0.5 ml, 0.5 ml, 2 ml, 2 ml, 1 ml, and 0.5 ml, to the solution of the organic salts of TPAA-nBu, TPAA-isoBu, TPAA-tAm, TPAA-nBu-tBu, TPAA-nBu-tAm, TPAA-isoBu-tBu, and TPAA-isoBu-tAm, respectively, as a poor solvent to decrease solubility of the organic salt, except for the solution of the organic salt TPAA-tBu.
    3. Keep the solution stable at room temperature in the glass vial, affording single crystals within a day.
  3. Confirm the organic salt formation by Fourier transform infrared (FT-IR) spectra35,36.
    1. Mix the single crystals of the organic salt with potassium bromide (KBr) in 1:100 weight ratio.
    2. Grind the mixture by an agate mortar until it becomes homogeneous powdered mixture.
    3. Fill up a round die (diameter: 5 mm) with the powdered mixture and make a pellet by pressing it with a pellet press.
    4. Put the pellet into a FT-IR spectrometer, and perform measurements (cumulative number: 16, resolution: 1 cm-1).

2. Crystallographic Studies

  1. Pick up a high quality single crystal of the organic salt TPAA-tAm from the glass vial into paraffin on a glass plate. The crystal looks uniform under a stereomicroscope, meaning the crystal is not assemblies of multiple crystals but a single crystal,  and has a crystal size around 0.3 to 1 mm without cracks.
  2. Put the single crystal on a loop.
  3. Set the loop with the single crystal in single crystal X-ray diffraction equipment.
  4. Select a collimator: 0.3, 0.5, 0.8, or 1 mm, depending on the maximum size of the single crystal.
  5. Start a preparatory measurement of single crystal X-ray diffraction to collect X-ray diffraction patterns37,38 from the single crystal using the single crystal X-ray diffraction equipment (radiation source: graphite monochromated CuKα (λ = 1.54187 Å), exposure time: 30 sec (determine based on the crystal size), detector: e.g. imaging plate, crystal-to-detector distance: 127.40 mm, temperature: 213.1 K, number of frames: 3).
  6. Determine possible crystal parameters and set conditions: exposure time, angles of X-ray exposure: ω, χ, and φ, and number of frames, for following measurement based on the result of the above preparatory measurement.
  7. Start a regular measurement of single crystal X-ray diffraction to collect X-ray diffraction patterns37,38 from the single crystals using the single crystal X-ray diffraction equipment under the conditions (radiation source: graphite monochromated CuKα (λ = 1.54187 Å), detector: e.g. imaging plate, crystal-to-detector distance: 127.40 mm, temperature: 213.1 K).
  8. Solve a crystal structure from the diffraction patterns by direct methods, SIR200439 or SHELXS9740, and refine by a full-matrix least-squares procedure using all the observed reflections based on F2. Refine all the non-hydrogen atoms with anisotropic displacement parameters, and place the hydrogen atoms in idealized positions with isotropic displacement parameters relative to the connected non-hydrogen atoms and not refined. Perform these calculations using a software such as the CrystalStructure41.
  9. Repeat the procedures from steps 2.1 to 2.8 with some modifications of the conditions: collimator size, exposure time of X-ray for preparatory measurements and regular measurements, and angles of X-ray exposure: ω, χ, and φ, and number of frames, for the single crystals of organic salts: TPAA-nBu-tBu, TPAA-nBu-tAm, TPAA-isoBu-tBu, and TPAA-isoBu-tAm to reveal their crystal structures.
  10. Retrieve crystal structures of the organic salts: TPAA-nBu (refcode: MIBTOH)22, TPAA-isoBu (refcode: GIVFEX)24, and TPAA-tBu (refcode: GIVFIB)23, from Cambridge Structural Database42 using a software, Conquest43, or a request form44.
  11. Investigate the supramolecular clusters in the crystal structures by computer graphics using software such as Mercury45-48 and Pymol49; Determine point group symmetries of hydrogen-bonding patterns in the supramolecular clusters by comparing the obtained patterns with the previously classified ones (Figure 1b) and chiral conformations of the trityl groups as Λ or Δ (Figure 1a).
  12. Characterize polyhedral features of the supramolecular clusters in each of the crystal structures of the organic salts.
    1. Delete all of the atoms in the supramolecular clusters except for carbon and nitrogen atoms of the component carboxylate anions and ammonium cations.
    2. Make bonds between the carbon and nitrogen atoms of which original carboxylate and ammonium cations are connected by hydrogen bonds.
    3. Measure distances between carbon-carbon and nitrogen-nitrogen atoms, and set boundaries for making further bonds (5.3 and 4.1 Å for carbon-carbon and nitrogen-nitrogen distances, respectively, in this study).
    4. Make further bonds between carbon-carbon and nitrogen-nitrogen atoms of which distances are less than 5.4 and 4.2 Å, respectively.
    5. Determine the resulting polyhedrons of the organic salts: TPAA-isoBu, TPAA-tBu, TPAA-tAm, TPAA-isoBu-tBu, and TPAA-isoBu-tAm, as trans-bicapped octahedron (tbo), triangular dodecahedron (td), td, td, and td, respectively, by considering rotational axis (C3 or C2) as well as numbers of sides of the polyhedrons.
    6. Make additional bonds to the resulting polyhedrons of the organic salts: TPAA-nBu, TPAA-nBu-tBu, and TPAA-nBu-tAm, by considering number of sides, symmetry elements, and intermolecular interactions in the supramolecular clusters because they have less sides than ideal ones: td, tbo, and square antiprism (sa).
    7. Determine the polyhedron of the TPAA-nBu salt as sa by making two addition bonds due to its C2 symmetry and 14 original bonds. Determine the other polyhedrons of the organic salts TPAA-nBu-tBu and TPAA-nBu-tAm as td based on their C2 symmetry and "bands" of the trityl groups around the supramolecular cluster. Namely, the trityl groups in the supramolecular clusters of the ternary organic salts form "bands" by intermeshing their three phenyl rings and the polyhedron td has sides connecting four acids (Figure 1c(ii)), meaning they have similar structural features.

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Results

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Organic salt formation of TPAA and primary amines were confirmed by FT-IR measurements. Crystal structures of the organic salts were analyzed by single crystal X-ray diffraction measurements. As a result, the same kinds of the supramolecular clusters, which are composed of four ammoniums and four triphenylacetates by charge-assisted hydrogen bonds (Figure 1a), were confirmed in all of the single crystals of the organic salts regardless of kinds and numbers of the componen...

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Discussion

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A series of supramolecular clusters with closed hydrogen-bonding networks was successfully constructed and characterized from viewpoints of chirality and polyhedral features using organic salts of TPAA, which has a trityl group, and various kinds and combinations of primary amines. In this method, the critical steps are introduction of a molecule with a bulky trityl group and recrystallization of organic salts composed of the molecule and counter ions from non-polar solvents. This is because the supramolecular cluster ha...

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Disclosures

$$\rightleftharpoonup{xx}$$ $$\longleftharp{xx}$$, $$\longrightharp{xx}$$,

The authors have nothing to disclose.

Acknowledgements

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This work was financially supported by Grant-in-Aid for Scientific Research B (24350072, 25288036) and Grant-in-Aid for Scientific Research on Innovative Areas (24108723) from MEXT and JSPS, Japan. T.S. acknowledges Grant-in-Aid for JSPS Fellows (25763), the GCOE Program of Osaka University and Grants for Excellent Graduate Schools, MEXT, Japan.

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Materials

List of materials used in this article
NameCompanyCatalog NumberComments
Triphenylacetic acidAldrichT81205-10G
n-ButylamineTCIB0707
IsobutylamineTCII0095
tert-ButylamineTCIB0709
tert-AmylamineTCIA1002
MethanolWako131-01826hazardous substance
TolueneWako204-01866hazardous substance
HexaneWako085-00416
KBrWako165-17111

References

$$\rightleftharpoonup{xx}$$ $$\longleftharp{xx}$$, $$\longrightharp{xx}$$,
  1. Lehn, J. -M. Supramolecular Chemistry. , Wiley-VCH. (1995).
  2. Lehn, J. -M. Perspectives in Supramolecular Chemistry-From Molecular Recognition towards Molecular Information Processing and Self-Organization. Angew. Chem. Int. Ed. Engl. 29 (11), 1304-1319 (1990).
  3. Lehn, J. -M. From Supramolecular Chemistry towards Constitutional Dynamic Chemistry and Adaptive Chemistry. Chem. Soc. Rev. 36 (2), 151-160 (2007).
  4. Fabbrizzi, L., Poggi, A. Sensors and Switches from Supramolecular Chemistry. Chem. Soc. Rev. 24 (3), 197-202 (1995).
  5. Zeng, F., Zimmerman, S. C. Dendrimers in Supramolecular Chemistry: From Molecular Recognition to Self-Assembly. Chem. Rev. 97 (5), 1681-1712 (1997).
  6. Joseph, R., Rao, C. P. Ion and Molecular Recognition by Lower Rim 1,3-Di-conjugates of Calix[4]arene as Receptors. Chem. Rev. 111 (8), 4658-4702 (2011).
  7. Kinbara, K., Hashimoto, Y., Sukegawa, M., Nohira, H., Saigo, K. Crystal Structures of the Salts of Chiral Primary Amines with Achiral Carboxylic Acids: Recognition of the Commonly-Occurring Supramolecular Assemblies of Hydrogen-Bond Networks and Their Role in the Formation of Conglomerates. J. Am. Chem. Soc. 118 (14), 3441-3449 (1996).
  8. Tamura, R., et al. Mechanism of Preferential Enrichment, an Unusual Enantiomeric Resolution Phenomenon Caused by Polymorphic Transition during Crystallization of Mixed Crystals Composed of Two Enantiomers. J. Am. Chem. Soc. 124 (44), 13139-13153 (2002).
  9. Megumi, K., Arif, F. N. B. M., Matumoto, S., Akazome, M. Design and Evaluation of Salts between N-Trityl Amino Acid and tert-Butylamine as Inclusion Crystals of Alcohols. Cryst. Growth Des. 12 (11), 5680-5685 (2012).
  10. Davey, R. J., et al. Racemic Compound Versus Conglomerate: Concerning the Crystal Chemistry of the Triazoylketone, 1-(4-chlorophenyl)-4,4-dimethyl-2-(1 H-1,2,4-triazol-1-yl)pentan-3-one. CrystEngComm. 16 (21), 4377-4381 (2014).
  11. Iwama, S., et al. Highly Efficient Chiral Resolution of DL-Arginine by Cocrystal Formation Followed by Recrystallization under Preferential-Enrichment Conditions. Chem. Eur. J. 20 (33), 10343-10350 (2014).
  12. Connelly, N. G., Damhus, T., Hartshorn, R. M., Hutton, A. T. Nomenclature of Inorganic Chemistry − IUPAC Recommendations 2005. , RSC Publishing. Cambridge, U.K. (2005).
  13. McDonald, S., Ojamäe, L., Singer, S. J. Graph Theoretical Generation and Analysis of Hydrogen-Bonded Structures with Applications to the Neutral and Protonated Water Cube and Dodecahedral Cluster. J. Phys. Chem. A. 102 (17), 2824-2832 (1998).
  14. Xantheas, S. S., Dunning, T. H. Jr Ab initio. Studies of Cyclic Water Cluster (H2O)n, n = 1-6. I. Optimal Structures and Vibrational Spectra. J. Chem. Phys. 99 (11), 8774-8792 (1993).
  15. MacGillivray, L. R., Atwood, J. L. A chiral spherical molecular assembly held together by 60 hydrogen bonds. Nature. 389 (6650), 469-472 (1997).
  16. Liu, Y., Hu, A., Comotti, A., Ward, M. D. Supramolecular Archimedean Cages Assembled with 72 Hydrogen Bonds. Science. 333 (6041), 436-440 (2011).
  17. Mautner, M. The Ionic Hydrogen Bond. Chem. Rev. 105 (1), 213-284 (2005).
  18. Ward, M. D. Charge-Assisted Hydrogen-Bonded Networks. Struct. Bond. 132, 1-23 (2009).
  19. Holman, K. T., Pivovar, A. M., Ward, M. D. Engineering Crystal Symmetry and Polar Order in Molecular Host Frameworks. Science. 294 (5548), 1907-1911 (2001).
  20. Ward, M. D. Design of Crystalline Molecular Networks with Charge-Assisted Hydrogen Bonds. Chem. Commun. 47, 5838-5842 (2005).
  21. Tohnai, N., et al. Well-Designed Supramolecular Clusters Comprising Triphenylmethylamine and Various Sulfonic Acids. Angew. Chem. Int. Ed. 46 (13), 2220-2223 (2007).
  22. Yuge, T., Tohnai, N., Fukuda, T., Hisaki, I., Miyata, M. Topological Study of Pseudo-Cubic Hydrogen-Bond Networks in a Binary System Composed of Primary Ammonium Carboxylates: An Analogue of an Ice Cube. Chem. Eur. J. 13 (15), 4163-4168 (2007).
  23. Sada, K., et al. Well-defined Ion-pair Clusters of Alkyl- and Dialkylammonium Salts of a Sterically-Hindered Carboxylic Acid. Implication for Hydrogen-bonded Lys Salt Bridges. Chem. Lett. 33 (2), 160-161 (2004).
  24. Yuge, T., Hisaki, I., Miyata, M., Tohnai, N. Guest-Induced Topological Polymorphism of Pseudo-Cubic Hydrogen Bond Networks-Robust and Adaptable Supramolecular Synthon. CrystEngComm. 10 (3), 263-266 (2008).
  25. Sasaki, T., et al. Chirality Generation in Supramolecular Clusters: Analogues of Octacoordinated Polyhedrons. Cryst. Growth Des. 15 (2), 658-665 (2015).
  26. Hisaki, I., Sasaki, T., Tohnai, N., Miyata, M. Supramolecular-Tilt-Chirality on Twofold Helical Assemblies. Chem. Eur. J. 18 (33), 10066-10073 (2012).
  27. Sasaki, T., Hisaki, I., Tsuzuki, S., Tohnai, N., Miyata, M. Halogen Bond Effect on Bundling of Hydrogen Bonded 2-Fold Helical Columns. CrystEngComm. 14 (18), 5749-5752 (2012).
  28. Yuge, T., Sakai, T., Kai, N., Hisaki, I., Miyata, M., Tohnai, N. Topological Classification and Supramolecular Chirality of 21-Helical Ladder-Type Hydrogen-Bond Networks Composed of Primary Ammonium Carboxylates: Bundle Control in 21-Helical Assemblies. Chem. Eur. J. 14 (10), 2984-2993 (2008).
  29. Sada, K., et al. Organic Layered Crystals with Adjustable Interlayer Distances of 1-Naphthylmethylammonium n-Alkanoates and Isomerism of Hydrogen-Bond Networks by Steric Dimension. J. Am. Chem. Soc. 126 (6), 1764-1771 (2004).
  30. Tanaka, A., et al. Supramolecular Chirality in Layered Crystals of Achiral Ammonium Salts and Fatty Acids: A Hierarchical Interpretation. Angew. Chem. Int. Ed. 45 (25), 4142-4145 (2006).
  31. Sada, K., et al. Multicomponent Organic Alloys Based on Organic Layered Crystals. Angew. Chem. Int. Ed. 44 (43), 7059-7062 (2005).
  32. Sasaki, T., et al. Characterization of Supramolecular Hidden Chirality of Hydrogen-Bonded Networks by Advanced Graph Set Analysis. Chem. Eur. J. 20 (9), 2478-2487 (2014).
  33. Okamoto, Y., Honda, S., Yashima, E., Yuki, H. Complete Chromatographic Resolution of Tris(acetylacetonato)cobalt(III) and Chromium(III) on an Optically Active Poly(triphenylmethyl methacrylate) Column. Chem. Lett. 12 (8), 1221-1224 (1983).
  34. Nakano, T., Okamoto, Y. Synthetic Helical Polymers: Conformation and Function. Chem. Rev. 101 (12), 4013-4038 (2001).
  35. Chalmers, J. M., Griffiths, P. R. Handbook of Vibrational Spectroscopy. , Wiley. (2002).
  36. Griffiths, P. R., Delaseth, J. A. Fourier Transform Infrared Spectrometry. , 2nd ed, John Wiley & Sons, Inc. (2007).
  37. Stout, G. H., Jensen, L. H. X-Ray Structure Determination: A Practical Guide. Wiley-Interscience. , 2nd ed, (1989).
  38. Massa, W. Crystal Structure Determination. , Springer. (2004).
  39. Burla, M. C., et al. SIR2004: an Improved Tool for Crystal Structure Determination and Refinement. J. Appl. Cryst. 32 (2), 115-119 (2005).
  40. Sheldrick, G. M. A Short History of SHELX. Acta Cryst. A. 64 (1), 112-122 (2008).
  41. Rigaku. CrystalStructure 3.8: Crystal Structure Analysis Package. , The Woodlands, TX, USA. (2007).
  42. Allen, F. H. The Cambridge Structural Database: A Quarter of a Million Crystal Structures and Rising. Acta Cryst. B: Structural Science. 58 (3), 380-388 (2002).
  43. Bruno, I. J., et al. New Software for Searching the Cambridge Structural Database and Visualising Crystal Structures. Acta Cryst. B: Structural Science. 58 (3), 389-397 (2002).
  44. Cambridge Crystallographic Data Centre. Cambridge Strucural Database Access From. , Available from: https://summary.ccdc.cam.ac.uk/structure-summary-form (2015).
  45. Macrae, C. F. Mercury CSD 2.0 - New Features for the Visualization and Investigation of Crystal Structures. J. Appl. Cryst. 41 (2), 466-470 (2008).
  46. Macrae, C. F. Mercury: Visualization and Analysis of Crystal Structures. J. Appl. Cryst. 39 (3), 453-457 (2006).
  47. Bruno, I. J. New Software for Searching the Cambridge Structural Database and Visualising Crystal Structures. Acta Cryst. B. 58 (3), 389-397 (2002).
  48. Taylor, R., Macrae, C. F. Rules Governing the Crystal Packing of Mono- and Di-alcohols. Acta Cryst. B. 57 (6), 815-827 (2001).
  49. Schrödinger, L. L. C. The PyMOL Molecular Graphics System, Version 1.7.1.6. , (2015).
  50. Gruenloh, C. J., Carney, J. R., Arrington, C. A., Zwier, T. S., Fredericks, S. Y., Jordan, K. D. Infrared Spectrum of a Molecular Ice Cube: The S4 and D2d Water Octamers in Benzene-(Water)8. Science. 276 (5319), 1678-1681 (1997).
  51. Blanton, W. B., et al. Synthesis and Crystallographic Characterization of an Octameric Water Complex (H2O)8. J. Am. Chem. Soc. 121 (14), 3551-3552 (1999).
  52. Yamamoto, A., et al. Diamondoid Porous Organic Salts toward Applicable Strategy for Construction of Versatile Porous Structures. Cryst. Growth Des. 12 (9), 4600-4606 (2012).

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