Crystalline Polymorphism of Organic Compounds

Crystal polymorphism is encountered in all areas of research involving solid substances. Its occurrence introduces complications during manufacturing processes and adds another dimension to the complexity of designing materials with specific properties. Research on polymorphism is fraught with unique difficulties due to the subtlety of polymorphic transformations and the inadvertent formation of pseudopolymorphs. In this report, a summary of thermodynamic, kinetic and structural considerations of polymorphism is presented. A wide variety of techniques appropriate to the study of organic crystalline polymorphism and pseu-dopolymorphism is then surveyed, ranging from simple crystal density measurement to observation of polymorphic transformations using variable-temperature synchrotron X-ray diffraction methods. Application of newer methodology described in this report is yielding fresh insights into the nature of the crystallization process, holding promise for a deeper understanding of the phenomenon of polymorphism and its practical control.

[1]  D. Fox Physics and Chemistry of the Organic Solid State , 1963 .

[2]  Joseph H. Flynn,et al.  A quick, direct method for the determination of activation energy from thermogravimetric data , 1966 .

[3]  A J Aguiar,et al.  Effect of polymorphism on the absorption of chloramphenicol from chloramphenicol palmitate. , 1967, Journal of pharmaceutical sciences.

[4]  H. Rietveld A profile refinement method for nuclear and magnetic structures , 1969 .

[5]  István Náray-Szabó,et al.  Inorganic crystal chemistry , 1969 .

[6]  W. Mccrone,et al.  Pharmaceutical applications of polymorphism. , 1969, Journal of pharmaceutical sciences.

[7]  F. Allen,et al.  Crystal and molecular structure of thalidomide, N-(α-glutarimido)-phthalimide , 1971 .

[8]  M. Kuhnert-Brandstätter Thermomicroscopy in the analysis of pharmaceuticals , 1971 .

[9]  J. Glusker,et al.  Crystal Structure Analysis: A Primer , 1972 .

[10]  F. Giordano,et al.  Preparation and characterization of 2-sulfanîlamido-5-methoxypyrimidine crystal forms. , 1974, Il Farmaco; edizione pratica.

[11]  J. Haleblian,et al.  Characterization of habits and crystalline modification of solids and their pharmaceutical applications. , 1975, Journal of pharmaceutical sciences.

[12]  Rex A. Palmer,et al.  Structure determination by X-ray crystallography , 1977 .

[13]  V. L. Himes,et al.  Structure of carbamazepine: 5H-dibenz[b,f]azepine-5-carboxamide , 1981 .

[14]  G. Kartha,et al.  Crystal structure of sulfamerazine , 1982 .

[15]  S. Byrn Solid state chemistry of drugs , 1982 .

[16]  A. Hoelgaard,et al.  Hydrate formation of metronidazole benzoate in aqueous suspensions , 1983 .

[17]  G. Bolhuis,et al.  Increased binding capacity and flowability of α‐lactose monohydrate after dehydration , 1983, The Journal of pharmacy and pharmacology.

[18]  J. Bernstein,et al.  Conformational polymorphism VI: the crystal and molecular structures of form II, form III, and form V of 4-amino-N-2-pyridinylbenzenesulfonamide (sulfapyridine). , 1985, Journal of pharmaceutical sciences.

[19]  Z. Berkovitch-yellin Toward an ab initio derivation of crystal morphology , 1985 .

[20]  R. Davey,et al.  The kinetics of solvent-mediated phase transformations , 1985, Proceedings of the Royal Society of London. A. Mathematical and Physical Sciences.

[21]  William A. Tiller Thermodynamic and kinetic considerations for crystal growth of complex molecules from solution , 1986 .

[22]  L. Addadi,et al.  Design of polymeric inhibitors for the control of crystal polymorphism. Induced enantiomeric resolution at racemic histidine by crystallization at 25.degree.C , 1987 .

[23]  A. P. Lötter,et al.  Physicochemical properties and X-ray structural studies of the trigonal polymorph of carbamazepine. , 1987, Journal of pharmaceutical sciences.

[24]  G. Desiraju Organic solid state chemistry , 1987 .

[25]  E. Ciurczak Uses of near-infrared spectroscopy in pharmaceutical analysis , 1987 .

[26]  Anthony R. West,et al.  Basic Solid State Chemistry , 1988 .

[27]  H. Chan,et al.  Serendipitous preparation of crystals of methotrexate and attempts to modify its crystal habit , 1989 .

[28]  M. Suleiman,et al.  Isolation and physicochemical characterization of solid forms of glibenclamide , 1989 .

[29]  M. Caira,et al.  Polymorphism of doxylamine succinate and X-ray structural study of Form I and of doxylamine succinate 0.5 succinic acid , 1990 .

[30]  J. Bernstein,et al.  Decoding hydrogen-bond patterns. The case of iminodiacetic acid , 1990 .

[31]  J. Dunitz,et al.  Conformational polymorphism of dimethyl 3,6-dichloro-2,5-dihydroxyterephthalate. II, Structural, thermodynamic, kinetic and mechanistic aspects of phase transformations among the three crystal forms , 1990 .

[32]  W. Mayer Acousto-optic imaging in different fields of acoustics , 1990 .

[33]  D. Seebach,et al.  Organic Synthesis—Where now? , 1990 .

[34]  K. Furic,et al.  Application of Raman spectroscopy in recognition of the two crystalline forms of terephthalic acid , 1990 .

[35]  Aalt Bast,et al.  Comprehensive medicinal chemistry , 1991 .

[36]  A. Gavezzotti,et al.  Generation of possible crystal structures from molecular structure for low-polarity organic compounds , 1991 .

[37]  Yoshio Harano,et al.  Growth and Solvent-Mediated Phase Transition of Cimetidine Polymorphic Forms A and B , 1991 .

[38]  M. Janik,et al.  Influence of solvent effect on polymorphism of 4-hydroxy-2-methyl-N-2-pyridyl-2H-1,2-benzothiazine-3-carboxamide-1, 1-dioxide (piroxicam) , 1991 .

[39]  W. H. Baur,et al.  The perils of Cc : comparing the frequencies of falsely assigned space groups with their general population , 1992 .

[40]  M. Merlo,et al.  Numerircal Determination of Nucleatilon Parameters in Polymoriphic Crystalliization from Solutiions , 1992 .

[41]  M. Kitamura Crystallization with Polymorphism and the Various Problems , 1992 .

[42]  D. Sandman,et al.  4, 4′-(butadiyne-l, 4-diyl)-bis-(2, 2, 6, 6-tetramethyl-4-hydroxypiperidin-1 -oxyl): A Convenient Synthesis and a Polymorphic Transformation Induced by Ionizing Radiation , 1992 .

[43]  M. C. Etter,et al.  Polymorphism in anthranilic acid: a reexamination of the phase transitions , 1992 .

[44]  L. McCusker,et al.  Ab initio structure determination from severely overlapping powder diffraction data , 1992 .

[45]  M. Caria,et al.  Positive indentification of two orthorhombic polymorphs of sulfamerazine (C11H12N4O2S), their thermal analyses and structural comparison , 1992 .

[46]  R. Gdanitz Prediction of molecular crystal structures by Monte Carlo simulated annealing without reference to diffraction data , 1992 .

[47]  I. Natkaniec,et al.  Neutron Diffraction and Direct Dilatometric Studies of Two Polymorphs of Meta‐Nitrophenol Crystal , 1992 .

[48]  M. Caira,et al.  X-ray structural characterization of anhydrous metronidazole benzoate and metronidazole benzoate monohydrate. , 1993, Journal of pharmaceutical sciences.

[49]  K. Sato,et al.  Polymorphic transformations in crystal growth , 1993 .

[50]  J. Anwar,et al.  Crystallization of polymorphs : the effect of solvent , 1993 .

[51]  V. Boldyrev,et al.  Phase Transformations in Sulfathiazole During Mechanical Activation , 1993 .

[52]  W. C. Kidd,et al.  The applicability of powder X-ray diffraction to the quantification of drug substance polymorphs using a model organic system , 1993, Powder Diffraction.

[53]  L. Leiserowitz,et al.  Tailor-made auxiliaries for the control of nucleation, growth and dissolution of two- and three-dimensional crystals , 1993 .

[54]  A. P. Lötter,et al.  Structures of two conformational polymorphs of the cholesterol-lowering drug probucol , 1993 .

[55]  J. Benvenuto,et al.  Degradation and inactivation of antitumor drugs. , 1993, Journal of pharmaceutical sciences.

[56]  A. Mitra,et al.  Development of Methods for tee Preparation and Evaluation of Chlorampeenicol Palmitate Ester and its Biopearmaceutically Effective Metastable Polymorph , 1993 .

[57]  M. Otsuka,et al.  Effects of Environmental Temperature and Compression Energy on Polymorphic Transformation During Tabletting , 1993 .

[58]  I. Dance,et al.  Prediction and structure of polymorphic lattice inclusion compounds of 2,7-dimethyltricyclo[4.3.1.03,8]undecane-syn-2,syn-7-diol , 1993 .

[59]  A. P. Lötter,et al.  Polymorphs of nitrofurantoin. 2. Preparation and X-ray crystal structures of two anhydrous forms of nitrofurantoin , 1993 .

[60]  J. Bernstein Crystal growth, polymorphism and structure-property relationships in organic crystals , 1993 .

[61]  P. Paronen,et al.  Effects of grinding and compression on crystal structure of anhydrous caffeine , 1993 .

[62]  M. Kitamura Crystallization behavior and transformation kinetics of L-histidine polymorphs , 1993 .

[63]  A. Gavezzotti,et al.  Are Crystal Structures Predictable , 1994 .

[64]  W. Winter,et al.  Molecular and crystal structure of a high-temperature polymorph of chitosan from electron diffraction data , 1994 .

[65]  Kenneth D. M. Harris,et al.  CRYSTAL STRUCTURE DETERMINATION FROM POWDER DIFFRACTION DATA BY MONTE CARLO METHODS , 1994 .

[66]  A. C. Mehta Review of analytical methods used in the dissolution testing of pharmaceuticals , 1994 .

[67]  M. C. Martínez‐Ohárriz,et al.  Polymorphism of diflunisal: isolation and solid-state characteristics of a new crystal form. , 1994, Journal of pharmaceutical sciences.

[68]  M. Caira,et al.  X-ray structural studies and physicochemical characterization of the 1-butanol, 1-pentanol, and 1,4-dioxane solvates of succinylsulfathiazole. , 1994, Journal of pharmaceutical sciences.

[69]  M. Caira,et al.  Polymorphism of N-(2,6-dioxo-3-piperidyl)pthalimide (thalidomide): Structural characterization of a second monoclinic racemic modification , 1994 .

[70]  R. Davey,et al.  Morphology and polymorphism in molecular crystals: terephthalic acid , 1994 .

[71]  T. Madan,et al.  Preparation and Characterization of Ranitidine-HC1 Crystals , 1994 .

[72]  M. Caira Molecular complexes of sulfonamides. 3. Structure of 5-methoxysulfadiazine (form II) and its 1∶1 complex with acetylsalicylic acid , 1994 .

[73]  M. Otsuka,et al.  Relation Between Polymorphic Transformation Pathway During Grinding and the Physicochemical Properties of Bulk Powders for Pharmaceutical Preparations , 1994 .

[74]  T. Yui,et al.  Effect of Explosion on the Crystalline Polymorphism of Chitin and Chitosan , 1994 .

[75]  P. Bruce,et al.  Probing molecular motion by solid-state NMR spectroscopy and high resolution powder X-ray diffraction , 1994 .

[76]  B. Ibragimov,et al.  Inclusion complexes of the natural product gossypol. The formation of different gossypol polymorphs on decomposition of channel type inclusion complexes , 1994 .

[77]  H. Furukawa,et al.  Solvent effect of ethanol on crystallization and growth process of L-histidine polymorphs , 1994 .

[78]  Morin,et al.  Model of the kinetics of polymorphous crystallization. , 1995, Physical review letters.

[79]  M. Ward,et al.  Selective Nucleation and Growth of an Organic Polymorph by Ledge-Directed Epitaxy on a Molecular Crystal Substrate , 1995 .

[80]  Raymond E. Davis,et al.  Patterns in Hydrogen Bonding: Functionality and Graph Set Analysis in Crystals , 1995 .

[81]  M. Caira,et al.  Crystal and molecular structures of three modifications of the androgen dehydroepiandrosterone (DHEA) , 1995 .

[82]  B. Lotz Structural polymorphism of crystalline polymers: Electron and atomic force microscopy contributions , 1995 .

[83]  A. Gubskaya,et al.  Effect of Cryogrinding on Physico-Chemical Properties of Drugs. II. Cortisone Acetate: Particles Sizes and Polymorphic Transition , 1995 .

[84]  M. Caira,et al.  Zwitterionic nature of tenoxicam: crystal structures and thermal analyses of a polymorph of tenoxicam and a 1:1 tenoxicam:acetonitrile solvate. , 1995, Journal of pharmaceutical sciences.

[85]  S. Byrn,et al.  Polymorphic characterization and structural comparisons of the non-linear optically active and inactive forms of two polymorphs of 1,3-bis(m-nitrophenyl)urea , 1995 .

[86]  P. Moretti,et al.  Growth rates of different polymorphs from interspherulitic boundary profiles , 1995 .

[87]  D. Giron Thermal analysis and calorimetric methods in the characterisation of polymorphs and solvates , 1995 .

[88]  M. Yasui Phase Transition of Organic Crystals , 1995 .

[89]  R. Céolin,et al.  Structure of a metastable phase of piracetami from X-ray powder diffraction using the atom–atom potential method , 1995 .

[90]  Kevin J. Roberts,et al.  On-line processing of pharmaceutical materials using in situ X-ray diffraction , 1995 .

[91]  K. Kjaer,et al.  Self‐assembled crystalline monolayers and multilayers of n‐alkanes on the water surface* , 1995 .

[92]  R. Popovitz‐Biro,et al.  Understanding and control of nucleation, growth, habit, dissolution and structure of two‐ and three‐dimensional crystals using `tailor‐made' auxiliaries , 1995 .

[93]  M. Caira,et al.  Solid state characterization of dehydroepiandrosterone. , 1995, Journal of pharmaceutical sciences.

[94]  L. Bartell Nucleation Rates in Freezing and Solid-State Transitions. Molecular Clusters as Model Systems , 1995 .

[95]  C. Alsenoy,et al.  Solids modeled by ab initio crystal field methods. X. Structure of α‐glycine, β‐glycine, and γ‐glycine using a 15‐molecule cluster , 1995 .

[96]  G. Wójcik,et al.  MONOTROPIC CHARACTER OF POLYMORPHISM IN PENTACHLOROPYRIDINE CRYSTAL STUDIED BY CALORIMETRIC AND SPECTROSCOPIC METHODS , 1995 .

[97]  A. Gavezzotti,et al.  Polymorphic Forms of Organic Crystals at Room Conditions: Thermodynamic and Structural Implications , 1995 .

[98]  J. Staněk,et al.  Crystal Packing Calculations and Rietveld Refinement in Elucidating the Crystal Structures of Two Modifications of 4-Amidinoindanone Guanylhydrazone , 1996 .

[99]  V. Hongisto,et al.  X-ray diffraction and microcalorimetry study of the α→β transformation of tripalmitin , 1996 .

[100]  K. Sato,et al.  13C cross-polarization and magic-angle spinning nuclear magnetic resonance of polymorphic forms of three triacylglycerols , 1996 .

[101]  K. Sada,et al.  Novel additive effect of inclusion crystals on polymorphs–cholic acid crystals having different hydrogen-bonded networks with the same organic guest , 1996 .

[102]  T. Yamanobe,et al.  Polymorphisms of 4,5-Bis(4-Methoxyphenyl)-2-(3-Nitrophenyl)-1H-Imidazole as Studied by Solid State NMR , 1996 .

[103]  Keiichi Koga,et al.  Process Systems Engineering. Behavior of Thiazol Acid Polymorphs in MethanolWater Mixed Solution. , 1996 .

[104]  C. Rérat,et al.  HIGH PRESSURE SOLID PHASES OF BENZENE. III. MOLECULAR PACKING ANALYSIS OF THE CRYSTALLINE STRUCTURES OF C6H6 , 1996 .

[105]  J. Greenberg Topology of P-T-X phase diagrams of binary systems. Polymorphism, metastable states and high-pressure equilibria , 1996 .

[106]  S. Bhatia,et al.  Formation and aggregation of polymorphs in continuous precipitation. 1. Mathematical modeling , 1996 .

[107]  Giuseppe Filippini,et al.  Computer Prediction of Organic Crystal Structures Using Partial X-ray Diffraction Data , 1996 .

[108]  P. Gemperline,et al.  Near-IR Detection of Polymorphism and Process-Related Substances , 1996 .

[109]  H. Yoshida,et al.  Conformational dependence of the isolated C-D stretching and CHD rocking vibrations of selectively monodeuterated alkyl chains as proved by conformational polymorphism of 1-bromopentane , 1996 .

[110]  A. Burger,et al.  POLYMORPHISM AND PSEUDOPOLYMORPHISM ON NIFEDIPINE , 1996 .

[111]  A. P. Lötter,et al.  Polymorphism and Pseudopolymorphism of the Antibacterial Nitrofurantoin , 1996 .

[112]  J. Sherwood,et al.  Polymorphism, twinning and morphology of crystals of 2,4,6-trinitrotoluene grown from solution , 1996 .

[113]  J. Wolff Crystal Packing and Molecular Geometry , 1996 .

[114]  D. E. Williams,et al.  Ab initio molecular packing analysis , 1996 .

[115]  Jean-Marie Lehn,et al.  Comprehensive Supramolecular Chemistry , 1996 .

[116]  J. Helliwell,et al.  X-Ray crystallography in structural chemistry and molecular biology , 1996 .

[117]  F. Vrečer,et al.  Polymorphism and pseudopolymorphism: Influencing the dissolution properties of the guanine derivative acyclovir , 1996 .

[118]  F. Leusen Ab initio prediction of polymorphs , 1996 .

[119]  E. Weber,et al.  Polymorphism of crystalline host–guest complexes and unsolvated hosts. Part 6. Pseudo-dimorphism of complexes between 1,1′-binaphthyl-2,2′-dicarboxylic acid and ethanol. X-Ray crystal structures of the β-form and of the unsolvated host compound , 1997 .

[120]  H. Brittain,et al.  Spectral methods for the characterization of polymorphs and solvates. , 1997, Journal of pharmaceutical sciences.

[121]  A. Gavezzotti,et al.  Theoretical aspects and computer modeling of the molecular solid state , 1997 .