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Published in:
Early History of X-Ray Crystallography Read chapter Read first chapter

2020 | OriginalPaper | Chapter

Crystallography Under High Pressures

Authors : Stephen A. Moggach, Iain D. H. Oswald

Published in: 21st Century Challenges in Chemical Crystallography I

Publisher: Springer International Publishing

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Abstract

This chapter highlights the area of crystallography of molecular systems under high-pressure conditions. It is an area of crystallography that has seen a rapid expansion over the last two decades. Advances in technology and data processing have facilitated the discovery of new materials, polymorphs and chemistries under extreme conditions. We discuss these advances using examples of organic and metal-organic materials as well as providing guidance to the pitfalls to be avoided conducting these studies.

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previous chapter Leading Edge Chemical Crystallography Service Provision and Its Impact on Crystallographic Data Science in the Twenty-First Century
next chapter Watching Photochemistry Happen: Recent Developments in Dynamic Single-Crystal X-Ray Diffraction Studies
Literature
1.
Oswald IDH, Lennie AR, Pulham CR, Shankland K (2010) High-pressure structural studies of the pharmaceutical, chlorothiazide. CrystEngComm 12:2533
2.
Moggach SA, Parsons S, Wood PA (2008) High-pressure polymorphism in amino acids. Crystallogr Rev 14:143–184
3.
Fairen-Jimenez D, Moggach SA, Wharmby MT, Wright PA, Parsons S, Düren T (2011) Opening the gate: framework flexibility in ZIF-8 explored by experiments and simulations. J Am Chem Soc 133:8900–8902PubMed
4.
Yoo CS, Cynn H (1999) Equation of state, phase transition, decomposition of β-HMX (octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine) at high pressures. J Chem Phys 111:10229–10235
5.
Millar DIA, Marshall WG, Oswald IDH, Pulham CR (2010) High-pressure structural studies of energetic materials. Crystallogr Rev 16:115–132
6.
Neumann MA, Van De Streek J, Fabbiani FPA, Hidber P, Grassmann O (2015) Combined crystal structure prediction and high-pressure crystallization in rational pharmaceutical polymorph screening. Nat Commun 6:7793PubMedPubMedCentral
7.
Bhardwaj RM, McMahon JA, Nyman J, Price LS, Konar S, Oswald IDH, Pulham CR, Price SL, Reutzel-Edens SM (2019) A prolific solvate former, galunisertib, under the pressure of crystal structure prediction, produces ten diverse polymorphs. J Am Chem Soc 141:13887–13897PubMed
8.
Boldyreva EV (2008) High-pressure diffraction studies of molecular organic solids. A personal view. Acta Crystallogr Sect A Found Crystallogr 64:218–231
9.
Fabbiani FPA, Pulham CR (2006) High-pressure studies of pharmaceutical compounds and energetic materials. Chem Soc Rev 35:932–942PubMed
10.
Katrusiak A (2008) High-pressure crystallography. Acta Cryst 64:135–148
11.
Miletich R, Allan DR, Kuhs WF (2000) High-pressure single-crystal techniques. Rev Mineral Geochem 41:445–519
12.
Sidorov NV, Krasyukov YN, Mukhtarova ÉI, Shkrabo DM (2000) Phase transition and domain structure in iodoform crystals. Crystallogr Rep 45:288–293
13.
Dziubek KF, Katrusiak A (2008) Polar symmetry in new high-pressure phases of chloroform and bromoform. J Phys Chem B 112:12001–12009PubMed
14.
Allan DR, Clark SJ (1999) Comparison of the high-pressure and low-temperature structures of ethanol and acetic acid. Phys Rev B Condens Matter Mater Phys 60:6328–6334
15.
Allan DR, Clark SJ, Brugmans MJP, Ackland GJ, Vos WL (1998) Structure of crystalline methanol at high pressure. Phys Rev B 58:R11809–R11812
16.
Ridout J, Probert MR (2014) Low-temperature and high-pressure polymorphs of isopropyl alcohol. CrystEngComm 16:7397–7400
17.
Bull CL, Funnell NP, Pulham CR, Marshall WG, Allan DR (2017) A new high-pressure polymorph of phosphoric acid. Acta Crystallogr Sect B Struct Sci Cryst Eng Mater 73:1068–1074
18.
Bridgman PW (1914) Change of phase under pressure. I. The phase diagram of eleven substances with especial reference to the melting curve. Phys Rev 3:126–141
19.
Dziubek K (2014) Complementing diffraction data with volumetric measurements. Zeitschrift für Krist Cryst Mater 229:129–134
20.
Marciniak J, Bakowicz J, Dobrowolski MA, Dziubek KF, Kaźmierczak M, Paliwoda D, Rajewski KW, Sobczak S, Stachowicz M, Katrusiak A (2016) Most frequent organic interactions compressed in toluene. Cryst Growth Des 16:1435–1441
21.
Oswald IDH, Crichton WA (2009) Structural similarities of 2-chlorophenol and 2-methylphenol. CrystEngComm 11:463–469
22.
Funnell NP, Dawson A, Marshall WG, Parsons S (2013) Destabilisation of hydrogen bonding and the phase stability of aniline at high pressure. CrystEngComm 15:1047–1060
23.
Oswald IDH, Allan DR, Motherwell WDS, Parsons S (2005) Structures of the monofluoro- and monochlorophenols at low temperature and high pressure. Acta Crystallogr Sect B Struct Sci 61:69–79
24.
Paliwoda D, Dziubek KF, Katrusiak A (2012) Imidazole hidden polar phase. Cryst Growth Des 12:4302–4305
25.
Delori A, Hutchison IB, Bull CL, Funnell NP, Urquhart AJ, Oswald IDH (2018) Reaction of acetylenedicarboxylic acid made easy: high-pressure route for polymerization. Cryst Growth Des 18:1425–1431
26.
Allan DR, Clark SJ, Ibberson RM, Parsons S, Pulham CR, Sawyer L (1999) The influence of pressure and temperature on the crystal structure of acetone. Chem Commun:751–752
27.
Vos WL, Finger LW, Hemley RJ, Hu JZ, Mao HK, Schouten JA (1992) A high-pressure van der Waals compound in solid nitrogen-helium mixtures. Nature 358:46–48
28.
Vos WL, Finger LW, Hemley RJ, Mao HK (1993) Novel H2-H2O clathrates at high pressures. Phys Rev Lett 71:3150–3153PubMed
29.
Weck G, Loubeyre P, LeToullec R, LeToullec R (2002) Observation of structural transformations in metal oxygen. Phys Rev Lett 88:4
30.
Lundegaard LF, Weck G, McMahon MI, Desgreniers S, Loubeyre P (2006) Observation of an O8 molecular lattice in the epsilon phase of solid oxygen. Nature 443:201–204PubMed
31.
Oswald IDH, Urquhart AJ (2011) Polymorphism and polymerisation of acrylic and methacrylic acid at high pressure. CrystEngComm 13:4503–4507
32.
Murli C, Song Y (2010) Pressure-induced polymerization of acrylic acid: a Raman spectroscopic study. J Phys Chem B 114:9744–9750PubMed
33.
Johnston BF, Marshall WG, Parsons S, Urquhart AJ, Oswald IDH (2014) Investigation of acrylic acid at high pressure using neutron diffraction. J Phys Chem B 118:4044–4051PubMedPubMedCentral
34.
Marshall WG, Urquhart AJ, Oswald IDH (2015) Investigation of methacrylic acid at high pressure using neutron diffraction. J Phys Chem B 119:12147–12154PubMed
35.
Marciniak J, Katrusiak A (2017) Direct and inverse relations between temperature and pressure effects in crystals: a case study on o-xylene. J Phys Chem C 121:22303–22309
36.
Haisa M, Kashino S, Kawai R, Maeda H (1976) The monoclinic form of p-hydroxyacetanilide. Acta Crystallogr Sect B Struct Crystallogr Cryst Chem 32:1283–1285
37.
Haisa M, Kashino S, Maeda H (1974) The orthorhombic form of p-hydroxyacetanilide. Acta Crystallogr Sect B Struct Crystallogr Cryst Chem 30:2510–2512
38.
Perlovich GL, Volkova TV, Bauer-Brandl A (2007) Polymorphism of paracetamol. J Therm Anal Calorim 89:767–774
39.
Nichols G, Frampton CS (1998) Physicochemical characterization of the orthorhombic polymorph of paracetamol crystallized from solution. J Pharm Sci 87:684–693PubMed
40.
Boldyreva EV, Shakhtshneider TP, Ahsbahs H, Sowa H, Uchtmann H (2002) Effect of high pressure on the polymorphs of paracetamol. J Therm Anal Calorim 68:437–452
41.
Fabbiani FPA, Allan DR, Dawson A, David WIF, McGregor PA, Oswald IDH, Parsons S, Pulham CR (2003) Pressure-induced formation of a solvate of paracetamol. Chem Commun (Camb) 3:3004–3005
42.
Fabbiani FPA, Allan DR, David WIF, Moggach SA, Parsons S, Pulham CR (2004) High-pressure recrystallisation - a route to new polymorphs and solvates. CrystEngComm 6:504–511
43.
Oswald IDH, Chataigner I, Elphick S, Fabbiani FPA, Lennie AR, Maddaluno J, Marshall WG, Prior TJ, Pulham CR, Smith RI (2009) Putting pressure on elusive polymorphs and solvates. CrystEngComm 11:359–366
44.
Fabbiani FPA, Allan DR, David WIF, Davidson AJ, Lennie AR, Parsons S, Pulham CR, Warren JE (2007) High-pressure studies of pharmaceuticals: an exploration of the behavior of piracetam. Cryst Growth Des 7:1115–1124
45.
Fabbiani FPA, Buth G, Levendis DC, Cruz-Cabeza AJ (2014) Pharmaceutical hydrates under ambient conditions from high-pressure seeds: a case study of GABA monohydrate. Chem Commun (Camb) 50:1817–1819
46.
Ledru J, Imrie CT, Pulham CR, Céolin R, Hutchinson JM (2007) High pressure differential scanning calorimetry investigations on the pressure dependence of the melting of paracetamol polymorphs I and II. J Pharm Sci 96:2784–2794PubMed
47.
Ward MR, Oswald IDH (2019) Antisolvent addition at extreme conditions. CrystEngComm 21:4437–4443
48.
Fabbiani FPA, Allan DR, Parsons S, Pulham CR (2005) An exploration of the polymorphism of piracetam using high pressure. CrystEngComm 7:179
49.
Collings IE, Hanfland M, Collings IE, Hanfland M (2019) Packing rearrangements in 4-hydroxycyanobenzene under pressure. Molecules 24:1759PubMedCentral
50.
McKellar SC, Moggach SA (2015) Structural studies of metal-organic frameworks under high pressure. Acta Crystallogr Sect B 71:587–607
51.
Eikeland E, Thomsen MK, Madsen SR, Overgaard J, Spackman MA, Iversen BB (2016) Structural collapse of the hydroquinone-formic acid clathrate: a pressure-medium-dependent phase transition. Chem Eur J 22:4061–4069PubMed
52.
Eikeland E, Thomsen MK, Overgaard J, Spackman MA, Iversen BB (2017) Intermolecular interaction energies in hydroquinone clathrates at high pressure. Cryst Growth Des 17:3834–3846
53.
Merrill L, Bassett WA (1974) Miniature diamond anvil pressure cell for single crystal x-ray diffraction studies. Rev Sci Instrum 45:290–294
54.
Boehler R, De Hantsetters K (2004) New anvil designs in diamond-cells. High Press Res 24:391–396
55.
Moggach SA, Allan DR, Parsons S, Warren JE (2008) Incorporation of a new design of backing seat and anvil in a Merrill–Bassett diamond anvil cell. J Appl Crystallogr 41:249–251
56.
Yamanaka T, Fukuda T, Hattori T, Sumiya H (2001) New diamond anvil cell for single-crystal analysis. Rev Sci Instrum 72:1458
57.
Kenichi T, Satoshi N (2003) Performance of a synthetic diamond backing-plate for the diamond-anvil cell at ultrahigh pressures. Rev Sci Instrum 74:3017
58.
Ahsbahs H (2004) New pressure cell for single-crystal X-ray investigations on diffractometers with area detectors. Zeitschrift für Krist Cryst Mater 219:305–308
59.
Fabbiani FPA, Buth G, Dittrich B, Sowa H (2010) Pressure-induced structural changes in wet vitamin B12. CrystEngComm 12:2541
60.
Grzechnik A, Meven M, Friese K (2018) Single-crystal neutron diffraction in diamond anvil cells with hot neutrons. J Appl Crystallogr 51:351–356
61.
Haberl B, Dissanayake S, Wu Y et al (2018) Next-generation diamond cell and applications to single-crystal neutron diffraction. Rev Sci Instrum 89:092902PubMed
62.
Binns J, Kamenev KV, McIntyre GJ, Moggach SA, Parsons S (2016) Use of a miniature diamond-anvil cell in high-pressure single-crystal neutron Laue diffraction. IUCrJ 3:168–179PubMedPubMedCentral
63.
Akella J, Kennedy GC (1971) Phase diagram of benzene to 35 kbar. J Chem Phys 55:793
64.
Lomberget T, Chataigner I, Bouyssi D, Maddaluno J, Balme G (2004) Diels–Alder cycloadditions of functionalized (Z)-1-benzylidene-2-methylene cyclohexanes: the beneficial effect of high pressure. Tetrahedron Lett 45:3437–3441
65.
Hutchison IB, Bull CL, Marshall WG, Parsons S, Urquhart AJ, Oswald IDH (2017) Compression of glycolide-h4 to 6GPa. Acta Crystallogr Sect B Struct Sci Cryst Eng Mater 73:1151–1157
66.
Ward MR, Younis S, Cruz-Cabeza AJ, Bull CL, Funnell NP, Oswald IDH (2019) Discovery and recovery of delta p -aminobenzoic acid. CrystEngComm 21:2058–2066
67.
Zieliński W, Katrusiak A (2015) Hydrate smaller than the anhydrate. CrystEngComm 17:5468–5473
68.
Millar DIA, Oswald IDH, Barry C, Francis DJ, Marshall WG, Pulham CR, Cumming AS (2010) Pressure-cooking of explosives - the crystal structure of ε-RDX as determined by X-ray and neutron diffraction. Chem Commun 46:5662–5664
69.
Wang W, Fortes AD, Dobson DP, Howard CM, Bowles J, Hughes NJ, Wood IG (2018) Investigation of high-pressure planetary ices by cryo-recovery. II. High-pressure apparatus, examples and a new high-pressure phase of MgSO 4 ·5H 2 O. J Appl Crystallogr 51:692–705PubMedPubMedCentral
70.
Hutchison IB, Delori A, Wang X, Kamenev KV, Urquhart AJ, Oswald IDH (2015) Polymorphism of a polymer precursor: metastable glycolide polymorph recovered via large scale high-pressure experiments. CrystEngComm 17:1778–1782
71.
Wood IG, Fortes AD, Dobson DP, Wang W, Pajdzik L, Cosier J (2018) Investigation of high-pressure planetary ices by cryo-recovery. I. An apparatus for X-ray powder diffraction from 40 to 315 K, allowing `cold loading’ of samples. J Appl Crystallogr 51:685–691
72.
Roszak K, Katrusiek A, Katrusiak A (2016) High-pressure preference for the low Z′ polymorph of a molecular crystal. Cryst Growth Des 16:3947–3953
73.
Yan TT, Xi DY, Wang JH, Fan XF, Wan Y, Zhang LX, Wang K (2019) High-pressure-induced phase transition in cinchomeronic acid polycrystalline form-I. Chinese Phys B 28:16104
74.
Abbas N, Oswald IDH, Pulham CR (2017) Accessing mefenamic acid form II through high-pressure recrystallisation. Pharmaceutics 9:16PubMedCentral
75.
Cosier J, Glazer AM (1986) A nitrogen-gas-stream cryostat for general X-ray diffraction studies. J Appl Crystallogr 19:105–107
76.
Brock CP, Duncan LL (1994) Anomalous space-group frequencies for monoalcohols CnHmOH. Chem Mater 6:1307–1312
77.
McGregor PA, Allan DR, Parsons S, Pulham CR (2005) The low-temperature and high-pressure crystal structures of cyclobutanol (C4H7OH). Acta Crystallogr Sect B Struct Sci 61:449–454
78.
Moggach SA, Allan DR, Lozano-Casal P, Parsons S (2005) High-pressure polymorphism of cyclopentanol (C5H10O): the structure of cyclopentanol phase-V at 1.5 GPa. J Synchrotron Radiat 12:590–597PubMed
79.
Mcgregor PA, Allan DR, Parsons S, Clark SJ (2006) Structural science hexamer formation in tertiary butyl alcohol (2-methyl-2-propanol, C 4 H 10 O). Res Pap Acta Cryst 62:599–605
80.
Oswald IDH, Allan DR, Day GM, Motherwell WDS, Parsons S (2005) Realizing predicted crystal structures at extreme conditions: the low-temperature and high-pressure crystal structures of 2-chlorophenol and 4-fluorophenol. Cryst Growth Des 5:1055–1071
81.
Allan DR, Clark SJ, Dawson A, McGregor PA, Parsons S (2002) Pressure-induced polymorphism in phenol. Acta Crystallogr Sect B Struct Sci 58:1018–1024
82.
Podsiadło M, Patyk E, Katrusiak A (2012) Chiral aggregation hierarchy in high-pressure resolved 2-butanol and 2,3-butanediol. CrystEngComm 14:6419
83.
Cavallo G, Metrangolo P, Milani R, Pilati T, Priimagi A, Resnati G, Terraneo G (2016) The halogen bond. Chem Rev 116:2478–2601PubMedPubMedCentral
84.
Bertolotti F, Curetti N, Benna P, Gervasio G (2013) The effects of P–T changes on intermolecular interactions in crystal structure of iodoform. J Mol Struct 1041:106–112
85.
Ridout J, Probert MR (2013) High-pressure and low-temperature polymorphism in C-H⋯F-C hydrogen bonded monofluorotoluenes. Cryst Growth Des 13:1943–1948
86.
Anioła M, Kwas K, Cai W, Katrusiak A (2016) High-pressure crystallizations of meta-dichlorobenzene and dibromobenzene and their solid solutions scheme 1. Atomic labels in the symmetry-independent molecules (labeled A and B) of. Cryst Growth Des 16:6304–6309
87.
Giordano N, Afanasjevs S, Beavers CM et al (2019) The effect of pressure on halogen bonding in 4-iodobenzonitrile. Molecules 24:2018PubMedCentral
88.
Enkelmann V, Wegner G, Novak K, Wagener KB (1993) Single-crystal-to-single-crystal photodimerization of cinnamic acid. J Am Chem Soc 115:10390–10391
89.
Fernandes MA, Levendis DC (2016) Photodimerisation of the α′-polymorph of ortho-ethoxy-trans-cinnamic acid occurs via a two-stage mechanism at 343 K yielding 100% α-truxillic acid. CrystEngComm 18:7363–7376
90.
Galica T, Bąkowicz J, Konieczny K, Turowska-Tyrk I (2018) Structural transformations in crystals induced by radiation and pressure. Part 6. The reactivity of difluorocinnamic acids under ambient and high pressures – comparative studies. Cryst Growth Des 18:1636–1644
91.
Galica T, Bąkowicz J, Konieczny K, Turowska-Tyrk I (2016) Structural transformations in crystals induced by radiation and pressure. Part 5. The influence of pressure on the course of the photochemical reaction in crystals of 2,6-difluorocinnamic acid. CrystEngComm 18:8871–8879
92.
Kaupp G (2003) Solid-state molecular syntheses: complete reactions without auxiliaries based on the new solid-state mechanism. CrystEngComm 5:117
93.
Fanetti S, Nobrega MM, Dziubek K, Citroni M, Sella A, McMillan PF, Hanfland M, Bini R (2019) Structure and reactivity of 2,4,6-tricyano-1,3,5-triazine under high-pressure conditions. CrystEngComm 21:4493–4500
94.
Wilhelm C, Boyd SA, Chawda S et al (2008) Pressure-induced polymerization of diiodobutadiyne in assembled cocrystals. J Am Chem Soc 130:4415–4420PubMed
95.
Jin HJ, Plonka AM, Parise JB, Goroff NS (2013) Pressure induced topochemical polymerization of diiodobutadiyne: a single-crystal-to-single-crystal transformation. CrystEngComm 15:3106–3110
96.
Poręba T, Ernst M, Zimmer D, Macchi P, Casati N (2019) Pressure-induced polymerization and electrical conductivity of a polyiodide. Angew Chem 131:6697–6701
97.
Groom CR, Bruno IJ, Lightfoot MP, Ward SC (2016) The Cambridge structural database. Acta Crystallogr Sect B Struct Sci Cryst Eng Mater B72:171–179
98.
Freire PTC (2010) Pressure-induced phase transitions in crystalline amino acids. Raman spectroscopy and x-ray diffraction. NATO Sci Peace Secur Ser B Phys Biophys:559–572
99.
Dawson A, Allan DR, Belmonte SA, Clark SJ, David WIF, McGregor PA, Parsons S, Pulham CR, Sawyer L (2005) Effect of high pressure on the crystal structures of polymorphs of glycine. Cryst Growth Des 5:1415–1427
100.
Moggach SA, Marshall WG, Rogers DM, Parsons S (2015) How focussing on hydrogen bonding interactions in amino acids can miss the bigger picture: a high-pressure neutron powder diffraction study of ε-glycine. CrystEngComm 17:5315–5328
101.
Boldyreva EV, Ivashevskaya SN, Sowa H, Ahsbahs H, Weber HP (2005) Effect of hydrostatic pressure on the γ-polymorph of glycine 1. A polymorphic transition into a new δ-form. Zeitschrift fur Krist 220:50–57
102.
Bull CL, Flowitt-Hill G, de Gironcoli S, Küçükbenli E, Parsons S, Pham CH, Playford HY, Tucker MG (2017) ζ-Glycine: insight into the mechanism of a polymorphic phase transition. IUCrJ 4:569–574PubMedPubMedCentral
103.
Tumanov NA, Boldyreva EV, Kolesov BA, Kurnosov AV, Quesada Cabrera R (2010) Pressure-induced phase transitions in l-alanine, revisited. Acta Crystallogr Sect B Struct Sci 66:458–471
104.
Funnell NP, Marshall WG, Parsons S (2011) Alanine at 13.6 GPa and its pressure-induced amorphisation at 15 GPa. CrystEngComm 13:5841–5848
105.
Funnell NP, Dawson A, Francis D, Lennie AR, Marshall WG, Moggach SA, Warren JE, Parsons S (2010) The effect of pressure on the crystal structure of l-alanine. CrystEngComm 12:2573
106.
Tumanov NA, Boldyreva EV (2012) X-ray diffraction and Raman study of dl-alanine at high pressure: revision of phase transitions. Acta Crystallogr Sect B Struct Sci 68:412–423
107.
Moggach SA, Allan DR, Clark SJ, Gutmann MJ, Parsons S, Pulham CR, Sawyer L (2006) High-pressure polymorphism in l-cysteine: the crystal structures of l-cysteine-III and l-cysteine-IV. Acta Crystallogr Sect B Struct Sci 62:296–309
108.
Minkov VS, Drebushchak VA, Ogienko AG, Boldyreva EV (2011) Decreasing particle size helps to preserve metastable polymorphs. A case study of dl-cysteine. CrystEngComm 13:4417
109.
Moggach SA, Allan DR, Morrison CA, Parsons S, Sawyer L (2005) Effect of pressure on the crystal structure of l-serine-I and the crystal structure of l-serine-II at 5.4 GPa. Acta Crystallogr Sect B 61:58–68
110.
Wood PA, Francis D, Marshall WG, Moggach SA, Parsons S, Pidcock E, Rohl AL (2008) A study of the high-pressure polymorphs of L-serine using ab initio structures and PIXEL calculations. CrystEngComm 10:1154–1166
111.
Moggach SA, Marshall WG, Parsons S (2006) High-pressure neutron diffraction study of L-serine-I and L-serine-II, and the structure of L-serine-III at 8.1 GPa. Acta Crystallogr Sect B Struct Sci 62:815–825
112.
Fisch M, Lanza A, Boldyreva E, Macchi P, Casati N (2015) Kinetic control of high-pressure solid-state phase transitions: a case study on l-serine. J Phys Chem C 119:18611–18617
113.
Johnstone RDL, Francis D, Lennie AR, Marshall WG, Moggach SA, Parsons S, Pidcock E, Warren JE (2008) High-pressure polymorphism in L-serine monohydrate: identification of driving forces in high pressure phase transitions and possible implications for pressure-induced protein denaturation. CrystEngComm 10:1758–1769
114.
Zakharov BA, Kolesov BA, Boldyreva EV (2012) Effect of pressure on crystalline l- and dl-serine: revisited by a combined single-crystal X-ray diffraction at a laboratory source and polarized Raman spectroscopy study. Acta Crystallogr Sect B Struct Sci 68:275–286
115.
Giordano N, Beavers CM, Kamenev KV, Marshall WG, Moggach SA, Patterson SD, Teat SJ, Warren JE, Wood PA, Parsons S (2019) High-pressure polymorphism in l-threonine between ambient pressure and 22 GPa. CrystEngComm 21:4444–4456
116.
Lozano-Casal P, Allan DR, Parsons S (2008) High-pressure structural study of L-α-glutamine and the use of Hirshfeld surfaces and graph-set notation to investigate the hydrogen bonding present in the structure up to 4.9 GPa. Acta Crystallogr Sect B Struct Sci 64:466–475
117.
Moggach SA, Allan DR, Parsons S, Sawyer L, Warren JE (2005) The effect of pressure on the crystal structure of hexagonal l-cystine. J Synchrotron Radiat 12:598–607PubMed
118.
Davidson AJ, Oswald IDH, Francis DJ, Lennie AR, Marshall WG, Millar DIA, Pulham CR, Warren JE, Cumming AS (2008) Explosives under pressure - the crystal structure of gamma-RDX as determined by high-pressure X-ray and neutron diffraction. CrystEngComm 10:162–165
119.
Sheldrick GM, IUCr (2015) SHELXT – integrated space-group and crystal-structure determination. Acta Crystallogr Sect A Found Adv 71:3–8
120.
Drebushchak TN, Drebushchak VA, Boldyreva EV (2011) Solid-state transformations in the β-form of chlorpropamide on cooling to 100 K. Acta Crystallogr Sect B Struct Sci 67:163–176
121.
Drebushchak TN, Drebushchak VA, Pankrushina NA, Boldyreva EV (2016) Single-crystal to single-crystal conformational polymorphic transformation in tolbutamide at 313 K. Relation to other polymorphic transformations in tolbutamide and chlorpropamide. CrystEngComm 18:5736–5743
122.
Drebushchak VA, Drebushchak TN, Chukanov NV, Boldyreva EV (2008) Transitions among five polymorphs of chlorpropamide near the melting point. J Therm Anal Calorim 93:343–351
123.
Boldyreva EV, Dmitriev V, Hancock BC (2006) Effect of pressure up to 5.5 GPa on dry powder samples of chlorpropamide form-A. Int J Pharm 327:51–57PubMed
124.
Seryotkin YV, Drebushchak TN, Boldyreva EV (2013) A high-pressure polymorph of chlorpropamide formed on hydrostatic compression of the [alpha]-form in saturated ethanol solution. Acta Crystallogr Sect B 69:77–85
125.
Zakharov BA, Goryainov SV, Boldyreva EV (2016) Unusual seeding effect in the liquid-assisted high-pressure polymorphism of chlorpropamide. CrystEngComm 18:5423–5428
126.
Zakharov BA, Seryotkin YV, Tumanov NA, Paliwoda DD, Hanfland M, Kurnosov AV, Boldyreva EV (2016) The role of fluids in high-pressure polymorphism of drugs: different behaviour of β-chlorpropamide in different inert gas and liquid media. RSC Adv 6:92629–92637
127.
Boldyreva EV, Arkhipov SG, Drebushchak TN et al (2015) Isoenergetic polymorphism: the puzzle of tolazamide as a case study. Chem - A Eur J 21:15395–15404
128.
Fedorov AY, Rychkov DA, Losev EA, Zakharov BA, Stare J, Boldyreva EV (2017) Effect of pressure on two polymorphs of tolazamide: why no interconversion? CrystEngComm 19:2243–2252
129.
Connor LE, Delori A, Hutchison IB, Nic Daeid N, Sutcliffe OB, Oswald IDH (2015) The ecstasy and the agony; compression studies of 3,4-methylenedioxymethamphetamine (MDMA). Acta Crystallogr Sect B Struct Sci Cryst Eng Mater 71:3–9
130.
Derollez P, Dudognon E, Affouard F, Danède F, Correia NT, Descamps M (2010) Ab initio structure determination of phase II of racemic ibuprofen by X-ray powder diffraction. Acta Crystallogr Sect B Struct Sci 66:76–80
131.
Freer AA, Bunyan JM, Shankland N, Sheen DB (1993) Structure of (S)-(+)-ibuprofen. Acta Crystallogr Sect C Cryst Struct Commun 49:1378–1380
132.
Ostrowska K, Kropidowska M, Katrusiak A (2015) High-pressure crystallization and structural transformations in compressed R, S -ibuprofen. Cryst Growth Des 15:1512–1517
133.
Rietveld IB, Barrio M, Tamarit J-L, Do B, Céolin R (2011) Enantiomer resolution by pressure increase: inferences from experimental and topological results for the binary enantiomer system ( R )- and ( S )-mandelic acid. J Phys Chem B 115:14698–14703PubMed
134.
Cai W, Marciniak J, Andrzejewski M, Katrusiak A (2013) Pressure effect on D, L-mandelic acid racemate crystallization. J Phys Chem C 117(14):7279–7285
135.
Marciniak J, Andrzejewski M, Cai W, Katrusiak A (2014) Wallach’s rule enforced by pressure in mandelic acid. J Phys Chem C 118(8):4309–4313
136.
Connor LE, Vassileiou AD, Halbert GW, Johnston BF, Oswald IDH (2019) Structural investigation and compression of a co-crystal of indomethacin and saccharin. CrystEngComm 21:4465–4472
137.
Caira MR, Alkhamis KA, Obaidat RM (2004) Preparation and crystal characterization of a polymorph, a monohydrate, and an ethyl acetate solvate of the antifungal fluconazole. J Pharm Sci 93:601–611PubMed
138.
Gorkovenko EA, Kichanov SE, Kozlenko DP, Belushkin AV, Wąsicki J, Nawrocik W, Mielcarek J, Dubrovinsky LS, Lathe C, Savenko BN (2015) The pressure-induced polymorphic transformations in fluconazole. J Pharm Sci 104:4164–4169PubMed
139.
Hutchison IB, Bull CL, Marshall WG, Urquhart AJ, Oswald IDH (2019) Pressure-induced polymorphism of caprolactam: a neutron diffraction study. Molecules 24:2174PubMedCentral
140.
Oswald IDH, Pulham CR (2008) Co-crystallisation at high pressure - an additional tool for the preparation and study of co-crystals. CrystEngComm 10:1114–1116
141.
Satthaphut N, Sutcliffe OB, Oswald IDH (2014) Putting the squeeze on mephedrone hydrogen sulfate. Zeitschrift für Krist Cryst Mater 229:101–111
142.
Cairns AB, Catafesta J, Levelut C, Rouquette J, van der Lee A, Peters L, Thompson AL, Dmitriev V, Haines J, Goodwin AL (2013) Giant negative linear compressibility in zinc dicyanoaurate. Nat Mater 12:212–216PubMed
143.
Moggach SA, Parsons S (2009) High pressure crystallography of inorganic and organometallic complexes. Spectrosc Prop Inorg Organomet Compd 40:324–354
144.
Tidey JP, Wong HLS, Schröder M, Blake AJ (2014) Structural chemistry of metal coordination complexes at high pressure. Coord Chem Rev 277–278:187–207
145.
Gütlich P, Ksenofontov V, Gaspar AB (2005) Pressure effect studies on spin crossover systems. Coord Chem Rev 249:1811–1829
146.
Woodall CH, Beavers CM, Christensen J, Hatcher LE, Intissar M, Parlett A, Teat SJ, Reber C, Raithby PR (2013) Hingeless negative linear compression in the mechanochromic gold complex [(C6F5Au)2(μ-1,4-diisocyanobenzene)]. Angew Chem Int Ed 52:9691–9694
147.
Cairns AB, Goodwin AL (2015) Negative linear compressibility. Phys Chem Chem Phys 17:20449–20465PubMed
148.
Madsen SR, Overgaard J, Stalke D, Iversen BB (2015) High-pressure single crystal X-ray diffraction study of the linear metal chain compound Co3(dpa)4Br2·CH2Cl2. Dalt Trans 44:9038–9043
149.
Wu L-C, Jones C, Stasch A, Platts JA, Overgaard J (2014) Non-nuclear attractor in a molecular compound under external pressure. Eur J Inorg Chem 2014:5536–5540
150.
Arnold PL, Prescimone A, Farnaby JH, Mansell SM, Parsons S, Kaltsoyannis N (2015) Characterizing pressure-induced uranium C−H agostic bonds. Angew Chem Int Ed 54:6735–6739
151.
Jarzembska KN, Kamiński R, Dziubek KF, Citroni M, Paliwoda D, Durka K, Fanetti S, Bini R (2018) Impact of high pressure on metallophilic interactions and its consequences for spectroscopic properties of a model tetranuclear Silver(I)–Copper(I) complex in the solid state. Inorg Chem 57:8509–8520PubMed
152.
Woodall CH, Christensen J, Skelton JM et al (2016) Observation of a re-entrant phase transition in the molecular complex tris(μ 2-3,5-diisopropyl-1,2,4-triazolato-κ 2 N 1:N 2)trigold(I) under high pressure. IUCrJ 3:367–376PubMedPubMedCentral
153.
Byrne PJ, Richardson PJ, Chang J, Kusmartseva AF, Allan DR, Jones AC, Kamenev KV, Tasker PA, Parsons S (2012) Piezochromism in Nickel salicylaldoximato complexes: tuning crystal-field splitting with high pressure. Chem Eur J 18:7738–7748PubMed
154.
Bruce-Smith IF, Zakharov BA, Stare J, Boldyreva EV, Pulham CR (2014) Structural properties of nickel dimethylglyoxime at high pressure: single-crystal X-ray diffraction and DFT studies. J Phys Chem C 118:24705–24713
155.
Takeda K, Hayashi J, Shirotani I, Fukuda H, Yakushi K (2006) Structural, optical, and electrical properties of one-dimensional bis(dimethylglyoximato)nickel(II), Ni(dmg) 2 at high pressure. Mol Cryst Liq Cryst 460:131–144
156.
Wu L-C, Overgaard J, Madsen SR, Schmøkel MS, Brummerstedt Iversen B (2013) High-pressure single-crystal X-ray diffraction study of the photomagnetic switching complex – [Y(DMF)4(H2O)3(μ-CN)Fe(CN)5]·H2O. J Chin Chem Soc 60:929–934
157.
Casati N, Macchi P, Sironi A (2005) Staggered to eclipsed conformational rearrangement of [Co2(CO)6(PPh3)2] in the solid state: an X-ray diffraction study at high pressure and low temperature. Angew Chem Int Ed 44:7736–7739
158.
Parois P, Moggach SA, Lennie AR, Warren JE, Brechin EK, Murrie M, Parsons S (2010) The effect of pressure on the crystal structure of Gd(PhCOO)(3)(DMF) (n) to 3.7 GPa and the transition to a second phase at 5.0 GPa. Dalt Trans 39:7004–7011
159.
Wittlinger J, Werner S, Schulz H (1998) Pressure-induced order-disorder phase transition of spinel single crystals. Acta Crystallogr Sect B 54:714–721
160.
Yan H, Yang F, Pan D et al (2018) Sterically controlled mechanochemistry under hydrostatic pressure. Nature 554:505PubMed
161.
Clegg JK, Brock AJ, Jolliffe KA, Lindoy LF, Parsons S, Tasker PA, White FJ (2017) Reversible pressure-controlled depolymerization of a copper(II)-containing coordination polymer. Chem Eur J 23:12480–12483PubMed
162.
Prescimone A, Morien C, Allan D, Schlueter JA, Tozer SW, Manson JL, Parsons S, Brechin EK, Hill S (2012) Pressure-driven orbital reorientations and coordination-sphere reconstructions in [CuF2(H2O)2(pyz)]. Angew Chem Int Ed 51:7490–7494
163.
Willett RD, Gatteschi D, Kahn O (1985) Magneto-structural correlations in exchange coupled systems. D Reidel Publishing, Boston
164.
Parois P, Moggach SA, Sanchez-Benitez J, Kamenev KV, Lennie AR, Warren JE, Brechin EK, Parsons S, Murrie M (2010) Pressure-induced Jahn–Teller switching in a Mn12 nanomagnet. Chem Commun 46:1881–1883
165.
Ghannadzadeh S, Möller JS, Goddard PA et al (2013) Evolution of magnetic interactions in a pressure-induced Jahn-Teller driven magnetic dimensionality switch. Phys Rev B 87:241102
166.
Ovcharenko V, Romanenko G, Polushkin A et al (2019) Pressure-controlled migration of paramagnetic centers in a heterospin crystal. Inorg Chem 58:9187–9194PubMed
167.
Dobe C, Strässle T, Juranyi F, Tregenna-Piggott PLW (2006) Pressure-induced switch of the direction of the unique Jahn−Teller axis of the Chromium(II) hexaqua cation in the deuterated ammonium chromium Tutton salt. Inorg Chem 45:5066–5072PubMed
168.
Augustyniak MA, Krupski M (1999) The temperature dependence of the pressure switching of Jahn–Teller deformation in the deuterated ammonium copper Tutton salt. Chem Phys Lett 311:126–130
169.
Prescimone A, Milios CJ, Sanchez-Benitez J et al (2009) High pressure induced spin changes and magneto-structural correlations in hexametallic SMMs. Dalt Trans 25:4858–4867
170.
Craig GA, Sarkar A, Woodall CH et al (2018) Probing the origin of the giant magnetic anisotropy in trigonal bipyramidal Ni(ii) under high pressure. Chem Sci 9:1551–1559PubMed
171.
Shepherd HJ, Rosa P, Vendier L, Casati N, Létard J-F, Bousseksou A, Guionneau P, Molnár G (2012) High-pressure spin-crossover in a dinuclear Fe(ii) complex. Phys Chem Chem Phys 14:5265–5271PubMed
172.
Shepherd HJ, Bonnet S, Guionneau P, Bedoui S, Garbarino G, Nicolazzi W, Bousseksou A, Molnár G (2011) Pressure-induced two-step spin transition with structural symmetry breaking: X-ray diffraction, magnetic, and Raman studies. Phys Rev B 84:144107
173.
Laisney J, Shepherd HJ, Rechignat L, Molnár G, Rivière E, Boillot ML (2018) Pressure-induced switching properties of the iron(iii) spin-transition complex [FeIII(3-OMeSalEen)2]PF6. Phys Chem Chem Phys 20:15951–15959PubMed
174.
Shepherd HJ, Palamarciuc T, Rosa P, Guionneau P, Molnár G, Létard J-F, Bousseksou A (2012) Antagonism between extreme negative linear compression and spin crossover in [Fe(dpp)2(NCS)2]·py. Angew Chem Int Ed 51:3910–3914
175.
Batten Stuart R, Champness Neil R, Chen X-M, Garcia-Martinez J, Kitagawa S, Öhrström L, O’Keeffe M, Paik Suh M, Reedijk J (2013) Terminology of metal–organic frameworks and coordination polymers (IUPAC recommendations 2013). Pure Appl Chem 85:1715
176.
Bennett TD, Cheetham AK (2014) Amorphous metal–organic frameworks. Acc Chem Res 47:1555–1562PubMed
177.
Gaillac R, Pullumbi P, Beyer KA, Chapman KW, Keen DA, Bennett TD, Coudert F-X (2017) Liquid metal–organic frameworks. Nat Mater 16:1149PubMed
178.
Moggach SA, Bennett TD, Cheetham AK (2009) The effect of pressure on ZIF-8: increasing pore size with pressure and the formation of a high-pressure phase at 1.47 GPa. Angew Chem Int Ed 48:7087–7089
179.
Serre C, Millange F, Thouvenot C, Noguès M, Marsolier G, Louër D, Férey G (2002) Very large breathing effect in the first nanoporous Chromium(III)-based solids: MIL-53 or CrIII(OH)·{O2C−C6H4−CO2}·{HO2C−C6H4−CO2H}x·H2Oy. J Am Chem Soc 124:13519–13526PubMed
180.
Zhang C, Gee JA, Sholl DS, Lively RP (2014) Crystal-size-dependent structural transitions in nanoporous crystals: adsorption-induced transitions in ZIF-8. J Phys Chem C 118:20727–20733
181.
Hobday CL, Woodall CH, Lennox MJ, Frost M, Kamenev K, Düren T, Morrison CA, Moggach SA (2018) Understanding the adsorption process in ZIF-8 using high pressure crystallography and computational modelling. Nat Commun 9:1429PubMedPubMedCentral
182.
Chapman KW, Halder GJ, Chupas PJ (2008) Guest-dependent high pressure phenomena in a nanoporous metal−organic framework material. J Am Chem Soc 130:10524–10526PubMed
183.
Graham AJ, Tan J-C, Allan DR, Moggach SA (2012) The effect of pressure on Cu-btc: framework compression vs. guest inclusion. Chem Commun 48:1535–1537
184.
Graham AJ, Allan DR, Muszkiewicz A, Morrison CA, Moggach SA (2011) The effect of high pressure on MOF-5: guest-induced modification of pore size and content at high pressure. Angew Chem Int Ed 50:11138–11141
185.
Graham AJ, Banu A-M, Düren T, Greenaway A, McKellar SC, Mowat JPS, Ward K, Wright PA, Moggach SA (2014) Stabilization of scandium terephthalate MOFs against reversible amorphization and structural phase transition by guest uptake at extreme pressure. J Am Chem Soc 136:8606–8613PubMed
186.
Aguado S, Bergeret G, Titus MP, Moizan V, Nieto-Draghi C, Bats N, Farrusseng D (2011) Guest-induced gate-opening of a zeolite imidazolate framework. New J Chem 35:546–550
187.
Yot PG, Ma Q, Haines J et al (2012) Large breathing of the MOF MIL-47(VIV) under mechanical pressure: a joint experimental–modelling exploration. Chem Sci 3:1100–1104
188.
Cavka JH, Jakobsen S, Olsbye U, Guillou N, Lamberti C, Bordiga S, Lillerud KP (2008) A new zirconium inorganic building brick forming metal organic frameworks with exceptional stability. J Am Chem Soc 130:13850–13851
189.
Su Z, Miao Y-R, Zhang G, Miller JT, Suslick KS (2017) Bond breakage under pressure in a metal organic framework. Chem Sci 8:8004–8011PubMedPubMedCentral
190.
Hobday CL, Marshall RJ, Murphie CF et al (2016) A computational and experimental approach linking disorder, high-pressure behavior, and mechanical properties in UiO frameworks. Angew Chem Int Ed 55:2401–2405
191.
Rogge SMJ, Wieme J, Vanduyfhuys L, Vandenbrande S, Maurin G, Verstraelen T, Waroquier M, Van Speybroeck V (2016) Thermodynamic insight in the high-pressure behavior of UiO-66: effect of linker defects and linker expansion. Chem Mater 28:5721–5732PubMedPubMedCentral
192.
Yot PG, Yang K, Ragon F, Dmitriev V, Devic T, Horcajada P, Serre C, Maurin G (2016) Exploration of the mechanical behavior of metal organic frameworks UiO-66(Zr) and MIL-125(Ti) and their NH2 functionalized versions. Dalt Trans 45:4283–4288
193.
Bennett TD, Tan J-C, Moggach SA, Galvelis R, Mellot-Draznieks C, Reisner BA, Thirumurugan A, Allan DR, Cheetham AK (2010) Mechanical properties of dense zeolitic imidazolate frameworks (ZIFs): a high-pressure X-ray diffraction, nanoindentation and computational study of the zinc framework Zn(Im)2, and its lithium boron analogue, LiB(Im)4. Chem Eur J 16:10684–10690PubMed
194.
Dissegna S, Vervoorts P, Hobday CL, Düren T, Daisenberger D, Smith AJ, Fischer RA, Kieslich G (2018) Tuning the mechanical response of metal–organic frameworks by defect engineering. J Am Chem Soc 140:11581–11584PubMed
195.
Wu H, Yildirim T, Zhou W (2013) Exceptional mechanical stability of highly porous zirconium metal–organic framework UiO-66 and its important implications. J Phys Chem Lett 4:925–930PubMed
196.
Peterson GW, DeCoste JB, Glover TG, Huang Y, Jasuja H, Walton KS (2013) Effects of pelletization pressure on the physical and chemical properties of the metal–organic frameworks Cu3(BTC)2 and UiO-66. Microporous Mesoporous Mater 179:48–53
197.
Peterson GW, DeCoste JB, Fatollahi-Fard F, Britt DK (2014) Engineering UiO-66-NH2 for toxic gas removal. Ind Eng Chem Res 53:701–707
Metadata
Title
Crystallography Under High Pressures
Authors
Stephen A. Moggach
Iain D. H. Oswald
Copyright Year
2020
Book
21st Century Challenges in Chemical Crystallography I

Print ISBN: 978-3-030-64742-1

Electronic ISBN: 978-3-030-64743-8

Copyright Year: 2020

DOI
https://doi.org/10.1007/430_2020_70

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