Understanding the agglomerate crystallisation of hexamine through X-ray microscopy and crystallographic modelling

Bulterov, 1859, Hexamethylenetetramine, Justus Liebigs Ann. Chem., 11, 250 Dickinson, 1923, The crystal structure of hexamethylene-tetramine, J. Am. Chem. Soc., 45, 22, 10.1021/ja01654a003 Brill, 1939, Anwendung der röntgenographischen Fourieranalyse auf Fragen der chemischen Bindung, Ann. Phys., 426, 393, 10.1002/andp.19394260502 Wyckoff, 1934, Spectrometric Measurements on Hexamethylene Tetramine and Urea, Zeitschrift für Kristallographie - Crystalline Materials, 89, 462, 10.1524/zkri.1934.89.1.462 Blažzević, 1979, Hexamethylenetetramine, a versatile reagent in organic synthesis, Synthesis, 1979, 161, 10.1055/s-1979-28602 Myerson, 1986, Solvent selection and batch crystallization, Ind. Eng. Chem. Process Des. Dev., 25, 925, 10.1021/i200035a015 Forno, 1974, The growth of large crystals of hexamine from solution, J. Cryst. Growth, 21, 61, 10.1016/0022-0248(74)90150-X Duckett, 1973, The growth of nearly perfect hexamethylenetetramine crystals from solution, J. Cryst. Growth, 18, 135, 10.1016/0022-0248(73)90190-5 Gottlieb, 1965, The Controlled Sublimation Technique and Its Utilization for the Crystal Growth of Hexamine, J. Electrochem. Soc., 112, 903, 10.1149/1.2423727 Alamdari, 2004, Kinetics of hexamine crystallization in industrial scale, Chem. Eng. Process., 43, 803, 10.1016/S0255-2701(03)00085-0 Bourne, 1976, The growth of hexamethylene tetramine crystals from ethanolic solutions, J. Cryst. Growth, 34, 230, 10.1016/0022-0248(76)90134-2 Bourne, 1976, The rotating disc configuration in the measurement of crystal growth kinetics from solution, J. Cryst. Growth, 34, 221, 10.1016/0022-0248(76)90133-0 Davey, 1976, Agglomeration in the crystallisation of hexamethylene tetramine from aqueous solution, J. Cryst. Growth, 32, 221, 10.1016/0022-0248(76)90036-1 Denbigh, 1966, Studies on liquid inclusions in crystals, Chem. Eng. Sci., 21, 739, 10.1016/0009-2509(66)87002-1 E.T. White, The formation and drying out of liquid inclusions in crystals. PhD thesis. 1964, Imperial College London, UK. Gibbs, 1878, On the equilibrium of heterogeneous substances, Am. J. Sci. Arts (1820-1879), 16, 441 Wulff, 1901, XXV. Zur frage der geschwindigkeit des wachsthums und der auflösung der krystallflächen, Zeitschrift für Kristallographie-Crystalline Materials, 34, 449, 10.1524/zkri.1901.34.1.449 O’hara, 1968, Discussion of interface stability of large facets on solution grown crystals, J. Cryst. Growth, 3-4, 555, 10.1016/0022-0248(68)90223-6 Brice, 1974, The stability of facets on growing crystals, J. Cryst. Growth, 26, 59, 10.1016/0022-0248(74)90200-0 Sun, 2009, Materials Science Tetrahedron—A Useful Tool for Pharmaceutical Research and Development, J. Pharm. Sci., 98, 1671, 10.1002/jps.21552 Shekunov, 2000, Crystallization processes in pharmaceutical technology and drug delivery design, J. Cryst. Growth, 211, 122, 10.1016/S0022-0248(99)00819-2 Datta, 2004, Crystal structures of drugs: advances in determination, prediction and engineering, Nat. Rev. Drug Discov., 3, 42, 10.1038/nrd1280 Feeder, 2015, The integration of solid-form informatics into solid-form selection, J. Pharm. Pharmacol., 67, 857, 10.1111/jphp.12394 Gajjar, 2021, Crystallographic tomography and molecular modelling of structured organic polycrystalline powders, CrstEngComm, 23, 2520, 10.1039/D0CE01712D Desiraju, 1995, Supramolecular synthons in crystal engineering—a new organic synthesis, Angew. Chem. Int. Ed. Eng., 34, 2311, 10.1002/anie.199523111 Nguyen, 2020, A digital workflow from crystallographic structure to single crystal particle attributes for predicting the formulation properties of terbutaline sulfate, CrstEngComm, 22, 3347, 10.1039/D0CE00026D Docherty, 1991, Application of Bravais-Friedel-Donnay-Harker, attachment energy and Ising models to predicting and understanding the morphology of molecular crystals, J. Phys. D Appl. Phys., 24, 89, 10.1088/0022-3727/24/2/001 Rosbottom, 2015, The solid state, surface and morphological properties of p-aminobenzoic acid in terms of the strength and directionality of its intermolecular synthons, CrstEngComm, 17, 5768, 10.1039/C5CE00302D Nguyen, 2017, Crystal morphology and interfacial stability of RS-Ibuprofen in relation to its molecular and synthonic structure, Cryst. Growth Des., 17, 3088, 10.1021/acs.cgd.6b01878 Turner, 2019, Habit Modification of the API Lovastatin through a Predictive Solvent Selection Approach, J. Pharm. Sci., 108, 1779, 10.1016/j.xphs.2018.12.012 Clydesdale, 2003, Molecular Modeling of Bulk Impurity Segregation and Impurity-Mediated Crystal Habit Modification of Naphthalene and Phenanthrene in the Presence of Heteroimpurity Species, J. Phys. Chem. B, 107, 4826, 10.1021/jp022423o Clydesdale, 2005, A Molecular Modeling Study of the Crystal Morphology of Adipic Acid and Its Habit Modification by Homologous Impurities, Cryst. Growth Des., 5, 2154, 10.1021/cg049720y Hammond, 2011, Molecular modelling of the incorporation of habit modifying additives: α-glycine in the presence of l-alanine, CrstEngComm, 13, 4935, 10.1039/c0ce00910e K.J. Roberts, R.B. Hammond, V. Ramachandran, R. Docherty, Synthonic engineering: from molecular and crystallographic structure to the rational design of pharmaceutical solid dosage forms, chapter 7, in Y.A. Abramov (Ed.), Computational Pharmaceutical Solid State Chemistry, Wiley, 2016, pp. 175–210. Pickering, 2017, Synthonic engineering modelling tools for product and process design, 155 Bunker, 2005, Towards screening of inhalation formulations: measuring interactions with atomic force microscopy, Expert Opin. Drug Deliv., 2, 613, 10.1517/17425247.2.4.613 Kampermann, 1995, Hexamethylenetetramine: extinction and thermal vibrations from neutron diffraction at six temperatures, Acta Crystallographica Section A: Foundations of Crystallography., 51, 489, 10.1107/S0108767394013711 Bachmann, 2019, 3D grain reconstruction from laboratory diffraction contrast tomography, J. Appl. Cryst., 52, 643, 10.1107/S1600576719005442 Feldkamp, 1984, Practical cone-beam algorithm, J. Opt. Soc. Am. A, 1, 612, 10.1364/JOSAA.1.000612 Clydesdale, 1994, Computational studies of the morphology of molecular crystals through solid-state intermolecular force calculations using the atom-atom method, 95 Mayo, 1990, DREIDING: a generic force field for molecular simulations, J. Phys. Chem., 94, 8897, 10.1021/j100389a010 Clydesdale, 1996, HABIT95—a program for predicting the morphology of molecular crystals as a function of the growth environment, J. Cryst. Growth, 166, 78, 10.1016/0022-0248(96)00056-5 Donnay, 1937, A new law of crystal morphology extending the law of Bravais, Am. Mineral.: J. Earth Planet. Mater., 22, 446 Friedel, 1907, Etudes sur la loi de Bravais, Bull. Minér., 30, 326 A. Bravais, Etudes Cristallographiques. Gauthier-Villars, Paris, 1866. Hartman, 1980, The attachment energy as a habit controlling factor: I. Theoretical considerations, J. Cryst. Growth, 49, 145, 10.1016/0022-0248(80)90075-5 Denbigh, 1963, Regular Inclusion Pattern in Crystals, Nature, 199, 799, 10.1038/199799a0 Plusjé, 1949, General discussion, Discuss. Faraday Soc., 5, 183, 10.1039/DF9490500183 W. Berg, Crystal growth from solutions, Proc. Roy. Soc. Lond. Series A-Math. Phys. Sci., 164 (916) (1938), 79-95. Bunn, 1949, Crystal growth from solution. II. Concentration gradients and the rates of growth of crystals, Discuss. Faraday Soc., 5, 132, 10.1039/df9490500132 C.W. Bunn, Crystals: Their Role in Nature and in Science, Academic Press, New York and London, 1964. J.W. Mullin, Crystallization, fourth ed., Butterworth-Heinemann, Oxford, 2001. Burton, 1951, The growth of crystals and the equilibrium structure of their surfaces, Philosophical Transactions of the Royal Society of London. Series A, Mathematical and Physical Sciences, 243, 299 Roberts, 1981, Dislocations in Y3Al5O12, J. Mater. Sci., 16, 2517, 10.1007/BF01113590 H. Klapper, Defects in non-metal crystals, in: B.K. Tanner, D.K. Bowen, (Eds.), Characterization of Crystal Growth Defects by X-Ray Methods, Nato Advanced Study Institutes Series, vol 63, Springer, Boston, MA, 1980, pp.133-160. Libbrecht, 2017, Physical dynamics of ice crystal growth, Annu. Rev. Mat. Res., 47, 271, 10.1146/annurev-matsci-070616-124135 J.D. Birchall, Private Communication, 1964, cited in the reference [14].