• Keine Ergebnisse gefunden

Sample handling differs from one compound to another; for each of the compounds studied detailed and tailor-made crystallisation protocols have been established. These are described in the experimental section of each chapter.

Chapter 1. Introduction 9

References 1.3.

(1) Burchell, T. D. Carbon Materials for Advanced Technologies, 1st ed.; Elsevier Science, 1999.

(2) Ströck, M. Eight Allotropes of Carbon (from the Wikipedia Commons) https://en.wikipedia.org/wiki/File:Eight_Allotropes_of_Carbon.png (accessed Aug 16, 2015).

(3) Haleblian, J.; McCrone, W. Pharmaceutical Applications of Polymorphism. J. Pharm. Sci.

1969, 58 (8), 911–929.

(4) IUCr. Online Dictionary of Crystallography - IUCr (accessed 13/08/2015) http://reference.iucr.org/dictionary/Polymorphism.

(5) Bernstein, J. Polymorphism in Molecular Crystals, 1st ed.; Oxford University Press: Oxford, United Kingdom, 2002.

(6) Bauer, J.; Spanton, S.; Henry, R.; Quick, J.; Dziki, W.; Porter, W.; Morris, J. Ritonavir: An Extraordinary Example of Conformational Polymorphism. Pharm. Res. 2001, 18 (6), 859–866.

(7) Morissette, S. L.; Soukasene, S.; Levinson, D.; Cima, M. J.; Almarsson, O. Elucidation of Crystal Form Diversity of the HIV Protease Inhibitor Ritonavir by High-Throughput Crystallization. Proc. Natl. Acad. Sci. U. S. A. 2003, 100 (5), 2180–2184.

(8) Bučar, D.-K.; Lancaster, R. W.; Bernstein, J. Disappearing Polymorphs Revisited. Angew.

Chemie Int. Ed. 2015, 54 (24), 6972–6993.

(9) Hilfiker, R. Polymorphism in the Pharmaceutical Industry, 1st ed.; WILEY-VCH Verlag GmbH

& Co.: Weinheim, 2006.

(10) Hilfiker, R.; Blatter, F.; von Raumer, M. Relevance of Solid-Stete Properties for Pharmaceutical Products. In Polymorphism: in the Pharmaceutical Industry; Hilfiker, R., Ed.;

WILEY-VCH Verlag GmbH & Co. KGaA: Weinheim - Germany, 2006; pp 1–17.

(11) Karpinski, P. H. Polymorphism of Active Pharmaceutical Ingredients. Chem. Eng. Technol.

2006, 29 (2), 233–237.

(12) Lee, E. H. A Practical Guide to Pharmaceutical Polymorph Screening & Selection. Asian J.

Pharm. Sci. 2014, 9 (4), 1–13.

(13) Lin, S. Y. An Overview of Famotidine Polymorphs: Solid-State Characteristics, Thermodynamics, Polymorphic Transformation and Quality Control. Pharm. Res. 2014, 31 (7), 1619–1631.

(14) Braga, D.; Grepioni, F.; Maini, L. The Growing World of Crystal Forms. Chem. Commun.

(Camb). 2010, 46 (34), 6232–6242.

(15) Fabbiani, F. P. A.; Pulham, C. R. High-Pressure Studies of Pharmaceutical Compounds and Energetic Materials. Chem. Soc. Rev. 2006, 35 (10), 932–942.

(16) Katrusiak, A. High-Pressure Crystallography. Acta Crystallogr. A. 2008, 64, 135–148.

(17) Boldyreva, E. V. Multicomponent Organic Crystals at High Pressure. Zeitschrift für Krist. -

Chapter 1. Introduction 10

Cryst. Mater. 2014, 229, 236–245.

(18) Boldyreva, E. High-Pressure Polymorphs of Molecular Solids: When Are They Formed, and When Are They Not? Some Examples of the Role of Kinetic Control. Cryst. Growth Des.

2007, 7 (9), 1662–1668.

(19) Merrill, L.; Bassett, W. A. Miniature Diamond Anvil Pressure Cell for Single Crystal X-Ray Diffraction Studies. Rev. Sci. Instrum. 1974, 45, 290–294.

(20) Allan, D. R.; Miletich, R.; Angel, R. J. A Diamond-Anvil Cell for Single-Crystal X-Ray Diffraction Studies to Pressures in Excess of 10 GPa. Rev. Sci. Instrum. 1996, 67 (3), 840–842.

(21) Ahsbahs, H. New Pressure Cell for Single-Crystal X-Ray Investigations on Diffractometers with Area Detectors. Zeitschrift für Krist. 2004, 219 (6-2004), 305–308.

(22) Moggach, S. A.; Allan, D. R.; Parsons, S.; Warren, J. E. Incorporation of a New Design of Backing Seat and Anvil in a Merrill-Bassett Diamond Anvil Cell. J. Appl. Crystallogr. 2008, 41 (2), 249–251.

(23) Billing, D. G.; Katrusiak, A. Non-Ambient Crystallography – Is Extreme Becoming Common? Acta Crystallogr. Sect. B Struct. Sci. Cryst. Eng. Mater. 2014, 70 (3), 399–400.

(24) Angel, R.; Bouvier, P.; Fabbiani, F. P. A. Preface – Special Issue on High Pressure. Zeitschrift für Krist. – Cryst. Mater. 2014, 229 (2).

(25) Hejny, C.; Minkov, V. S. High-Pressure Crystallography of Periodic and Aperiodic Crystals.

IUCrJ 2015, 2 (2), 218–229.

(26) Loftsson, T.; Brewster, M. E.; Rewster, M. A. E. B. Pharmaceutical Applications of Cyclodextrins. 1. Drug Solubilization and Stabilization. J. Pharm. Sci. 1996, 85 (10), 1017–

1025.

(27) Mizuuchi, H.; Jaitely, V.; Murdan, S.; Florence, a. T. Room Temperature Ionic Liquids and Their Mixtures: Potential Pharmaceutical Solvents. Eur. J. Pharm. Sci. 2008, 33 (4-5), 326–331.

(28) Smith, K. B.; Bridson, R. H.; Leeke, G. A. Solubilities of Pharmaceutical Compounds in Ionic Liquids. J. Chem. Eng. Data 2011, 56, 2039–2043.

(29) Giron, D. Investigations of Polymorphism and Pseudo-Polymorphism in Pharmaceuticals by Combined Thermoanalytical Techniques. J. Therm. Anal. Calorim. 2001, 64, 37–60.

(30) Arunan, E.; Desiraju, G. R.; Klein, R. a.; Sadlej, J.; Scheiner, S.; Alkorta, I.; Clary, D. C.;

Crabtree, R. H.; Dannenberg, J. J.; Hobza, P.; et al. Defining the Hydrogen Bond: An Account (IUPAC Technical Report). Pure Appl. Chem. 2011, 83 (8), 1619–1636.

(31) Stone, A. The Theory of Intermolecular Forces, 2nd ed.; Oxford University Press: Oxford, United Kingdom, 2013.

(32) Rissanen, K. Advanced X-Ray Crystallography; Springer-Verlag Berlin Heidelberg: Berlin - Heidelberg, Germany, 2012.

(33) Giacovazzo, C.; Monaco, H. L.; Viterbo, D.; Scordari, F.; Gilli, G.; Zanotti, G.; Catti, M.

Fundamentals of Crystallography; Giacovazzo, C., Ed.; Oxford University Press: New York, 1997; Vol. 198.

Chapter 1. Introduction 11

(34) Massa, W. Crystal Structure Determination, 2nd ed.; Springer-Verlag Berlin Heidelberg:

Berlin - Heidelberg, Germany, 2004.

(35) Müller, P.; Herbst-Irmer, R.; Spek, A.; Schneider, T.; Sawaya, M. Crystal Structure Refinement:

A Crystallographer’s Guide to SHELXL; Oxford University Press: Oxford, United Kingdom, 2006.

(36) Clegg, B.; Cooper, R.; Copley, R. C. B.; Howard, J. A. K.; Palatinus, L.; Parsons, S.; Sivia, D.

X-Ray Structure Analysis - 14th BCA/CCG Intensive Teaching School on X-Ray Structure Analysis; Trevelyan College, Durham, UK: Durham, IK, 2012.

(37) Glusker, J. P.; Trueblood, K. N. Crystal Structure Analysis: A Primer, 3rd ed.; Oxford University Press: Oxford, United Kingdom, 2010.

(38) Borchard-Ott, W. Crystallography: An Introduction, 3rd ed.; Springer-Verlag Berlin Heidelberg: Berlin - Heidelberg, Germany, 2012.

(39) Bridgman, P. W. The Physics of High Pressure; Dover Publications: London, United Kingdom, 1931.

(40) Bridgman, P. W. Recent Work in the Field of High Pressures. Rev. Mod. Phys. 1946, 18 (1), 1–

93.

(41) Jayaraman, A. Diamond Anvil Cell and High-Pressure Physical Investigations. Rev. Mod.

Phys. 1983, 55 (1), 65–108.

(42) Hazen, R. M.; Downs, R. T. High-Temperature & High-Pressure Crystal Chemistry (Reviews in Mineralogy and Geochemistry Volume 41); Mineralogical Society of America: Chantilly, United States, 2001.

(43) Hazen, R. M.; Finger, L. W. Comparative Crystal Chemistry: Temperature, Pressure, Composition, and the Variation of Crystal Structure, 1st ed.; Finger, L. W., Ed.; John Wiley & Sons Ltd: New Jersey, 1982.

(44) McMahon, M. I. High Pressure Diffraction from Good Powders, Poor Powders and Poor Single Crystals. In High-pressure Crystallography; Katrusiak, A., McMillan, P., Eds.; Springer Netherlands: Dordrecht, Netherlands, 2004; pp 1–20.

(45) Jamieson, J. C.; Lawson, A. W.; Nachtrieb, N. D. New Device for Obtaining X-Ray Diffraction Patterns from Substances Exposed to High Pressure. Rev. Sci. Instrum. 1959, 30 (11), 1016–1019.

(46) Weir, C. E.; E. R. Lippincott; Valkenburg, A. Van; Bunting, E. N. Infrared Studies in the 1- to 15-Micron Region to 30,000 Atmospheres. J. Reasearch Natl. Bur. Stand. - A. Phys. Chem. 1959, 63A (1), 55–62.

(47) Piermarini, G. J.; Block, S.; Barnett, J. D.; Forman, R. A. Calibration of the Pressure Dependence of the R1 Ruby Fluorescence Line to 195 Kbar. J. Appl. Phys. 1975, 46 (6), 2774–

2780.

(48) Boldyreva, E. V.; Dera, P. High-Pressure Crystallography: From Fundamental Phenomena to Technological Applications, 1st ed.; Springer Netherlands: Dordrecht, Netherlands, 2010.

(49) Miletich, R.; Allan, D. R.; Kuhs, W. F. High-Pressure Single-Crystal Techniques. In

High-Chapter 1. Introduction 12

Temperature & High-Pressure Crystal Chemistry (Reviews in Mineralogy and Geochemistry Volume 41); Hazen, R. M., Downs, R. T., Eds.; Mineralogical Society of America: Chantilly, United States, 2001; pp 445–519.

(50) Schrader, B. Infrared and Raman Spectroscopy: Methods and Applications, 1st ed.; VCH:

Weinheim, Germany, 1995.

(51) Colthup, N. B.; Daly, L. H.; Wiberley, S. E. Introduction to Infrared and Raman Spectroscopy, 3rd ed.; Academic Press, Inc.: San Diego, 1990.

(52) Ferraro, J. R.; Nakamoto, K.; Brown, C. W. Introductory Raman Spectroscopy, 2nd ed.;

Academic Press, Inc.: Waltham, 2003.

(53) McCrone, W. C. Fusion Methods in Chemical Microscopy; Interscience Publishers Inc.: New York, United States of America, 1957.

(54) Vitez, I. M.; Newman, A. W.; Davidovich, M.; Kiesnowski, C. The Evolution of Hot-Stage Microscopy to Aid Solid-State Characterizations of Pharmaceutical Solids. Thermochim. Acta 1998, 324 (1-2), 187–196.

(55) Bakar, M. R. A.; Nagy, Z. K.; Rielly, C. D. A Combined Approach of Differential Scanning Calorimetry and Hot-Stage Microscopy with Image Analysis in the Investigation of Sulfathiazole Polymorphism. J. Therm. Anal. Calorim. 2010, 99 (2), 609–619.

(56) McCall, J. L.; French, P. M. Interpretive Techniques for Microstructural Analysis, 1st Ed.;

Springer US: New York, United States of America, 1977.

13

PART I.

Exploring Inclusion Complex Formation of