Most Frequent Organic Interactions Compressed in Toluene

Marciniak, Jędrzej; Bąkowicz, Julia; Dobrowolski, Michał A.; Dziubek, Kamil; Kaźmierczak, Michał; Paliwoda, Damian; Rajewski, Kacper W.; Sobczak, Szymon; Stachowicz, Marcin; Katrusiak, Andrzej

doi:10.1021/acs.cgd.5b01538

Cited by 34 publications

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References 53 publications

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“…This is in agreement with the previously reported analysis of the shortest contacts hierarchy in crystals of compounds manifesting high-pressure poly- morphism, showing that the nature of the shortest contact, relative to the sum of van der Waals radii, remains unchanged (Kaźmierczak & Katrusiak, 2015). At the same time, a significant rearrangement in contacts of larger value can be observed (Kaźmierczak & Katrusiak, 2015;Marciniak et al, 2016a), and such tendency is present in BZC (Fig. 6).…”

Section: Resultssupporting

confidence: 93%

A new high-pressure benzocaine polymorph — towards understanding the molecular aggregation in crystals of an important active pharmaceutical ingredient (API)

Patyk‐Kaźmierczak

Kaźmierczak

2020

Acta Crystallogr B Struct Sci Cryst Eng Mater

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Benzocaine (BZC), an efficient and highly permeable anaesthetic and an active pharmaceutical ingredient of many commercially available drugs, was studied under high pressure up to 0.78 GPa. As a result, new BZC polymorph (IV) was discovered. The crystallization of polymorph (IV) can be initiated by heating crystals of polymorph (I) at a pressure of at least 0.45 GPa or by their compression to 0.60 GPa. However, no phase transition from polymorph (I) to (IV) was observed. Although polymorph (IV) exhibits the same main aggregation motif as in previously reported BZC polymorphs (I)–(III), i.e. a hydrogen-bonded ribbon, its molecular packing and hydrogen-bonding pattern differ considerably. The N—H...N hydrogen bonds joining parallel BZC ribbons in crystals at ambient pressure are eliminated in polymorph (IV), and BZC ribbons become positioned at an angle of about 80°. Unfortunately, crystals of polymorph (IV) were not preserved on pressure release, and depending on the decompression protocol they transformed into polymorph (II) or (I).

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Section: Resultssupporting

confidence: 93%

A new high-pressure benzocaine polymorph — towards understanding the molecular aggregation in crystals of an important active pharmaceutical ingredient (API)

Patyk‐Kaźmierczak

Kaźmierczak

2020

Acta Crystallogr B Struct Sci Cryst Eng Mater

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“…The first series was aimed at checking that there are no other high-pressure phases, which would require in situ recrystallization. Such 'hidden' polymorphs were observed previously for other organic compounds: imidazole (Paliwoda et al, 2012), benzene (Bridgman, 1911), di-p-tolyl disulfide ( Sobczak & Katrusiak, 2017), 3-hydroxy-4,5-dimethyl-1 phenylpyridazin-6-one (Roszak et al, 2016), toluene (Marciniak et al, 2016), and others (Boldyreva et al, 2002;Fabbiani et al, 2014). Thus, in the first series of experiments, the crystal of xylitol was grown in situ in a diamond-anvil cell (DAC) of the Merrill-Bassett type (Merrill & Bassett, 1974).…”

Section: Methodssupporting

confidence: 71%

Structure–property relationships of molecular shape and orientation with compression and expansion of xylitol

Safari

Katrusiak

2021

Acta Crystallogr Sect B

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Easy crystallization distinguishes xylitol from other sugars, which usually condense into a syrup from aqueous solution. Although two polymorphs, i.e. metastable monoclinic and high-density orthorhombic, have been reported for xylitol, only the latter is in practical use. Under high pressure, the same orthorhombic phase has been obtained by both isothermal and isochoric recrystallization. The stability of the orthorhombic xylitol phase to 5.0 GPa has been correlated with a uniform compression of all hydrogen bonds and some flexibility of the molecular conformation, which cushion the pressure-induced local strains. The anisotropic compressibility of xylitol and its thermal expansion are consistent with the rule of inverse effects of pressure and temperature. This inverse strain relationship has been correlated with the dimensions and orientation of xylitol molecules in the crystal structure.

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“…A suitable approach to circumvent crystal structures with Z′ > 1 could be the usage of in situ crystallization technique directly on the diffractometer . Other approaches to circumvent large Z′ were demonstrated by Katrusiak et al in recent studies, which focused on the influence of high pressure on Z′ …”

Section: Introductionmentioning

confidence: 99%

In situ Crystallization Technique - an Approach to Circumvent Crystal Structures with high Z′-Crystallization Behavior of (CF₃)₂C-OH

Lipinski

Mallik

Merz

2017

Z. Anorg. Allg. Chem.

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In situ crystallization on the diffractometer of 1,1,1,3,3,3hexafluoro-2-propanol (HFIP) with and without pyridine allows to obtain the new polymorphic form II of HFIP and the cocrystal HFIPpyridine. In contrast of the known HFIP form I, single-crystal X-ray diffraction analysis of HFIP form II shows a reduced number of mol-683 ecules in the asymmetric unit (form I: ZЈ = 8, form II: ZЈ = 4) Furthermore, UNI Force Field calculations were used to gain a deeper understanding of the intermolecular potentials of the main interactions of the described crystal structures.

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Most Frequent Organic Interactions Compressed in Toluene

Abstract: sp3)C7-H7AC•••C3' 2.789(3) 2.726(2) 2.667(2) 2.668(6) x-1, y, z (sp2)C6-H6•••C5' 2.706(2) 2.661(2) 2.642(2) 2.632(5) x-0.5, y, 0.5-z

Cited by 34 publications

References 53 publications

A new high-pressure benzocaine polymorph — towards understanding the molecular aggregation in crystals of an important active pharmaceutical ingredient (API)

A new high-pressure benzocaine polymorph — towards understanding the molecular aggregation in crystals of an important active pharmaceutical ingredient (API)

Structure–property relationships of molecular shape and orientation with compression and expansion of xylitol

In situ Crystallization Technique - an Approach to Circumvent Crystal Structures with high Z′-Crystallization Behavior of (CF₃)₂C-OH

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Most Frequent Organic Interactions Compressed in Toluene

Abstract: sp3)C7-H7AC•••C3' 2.789(3) 2.726(2) 2.667(2) 2.668(6) x-1, y, z (sp2)C6-H6•••C5' 2.706(2) 2.661(2) 2.642(2) 2.632(5) x-0.5, y, 0.5-z

Cited by 34 publications

References 53 publications

A new high-pressure benzocaine polymorph — towards understanding the molecular aggregation in crystals of an important active pharmaceutical ingredient (API)

A new high-pressure benzocaine polymorph — towards understanding the molecular aggregation in crystals of an important active pharmaceutical ingredient (API)

Structure–property relationships of molecular shape and orientation with compression and expansion of xylitol

In situ Crystallization Technique - an Approach to Circumvent Crystal Structures with high Z′-Crystallization Behavior of (CF3)2C-OH

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In situ Crystallization Technique - an Approach to Circumvent Crystal Structures with high Z′-Crystallization Behavior of (CF₃)₂C-OH