Isostructurality among Five Solvates of Phenylbutazone

Hosokawa, Toshihito; Datta, Sharmistha; Sheth, Agam R.; Brooks, Neil R.; Grant, David J.W.

doi:10.1021/cg049923m

Cited by 50 publications

(32 citation statements)

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“…3,4 According to the IUCr definition of isostructurality, "Two crystals are said to be isostructural if they have the same structure, but not necessarily the same unitcell dimensions nor the same chemical composition, with a comparable variability in the atomic coordinates to that of the cell dimensions and chemical composition". 5 It is of interest to study the phenomenon of isostructurality in isostructural polymorphs, [6][7][8][9][10][11] isostructural co-crystals 1,12,13 and isostructural solvates 14 on account of their applications in the pharmaceutical industry. [15][16][17][18][19][20] This behaviour is very common in similar related compounds having different types of structural equivalent functionalities like -H, -CH 3 , -F, -Cl, -Br and I.…”

Section: Introductionmentioning

confidence: 99%

Occurrence of 3D isostructurality in fluorinated phenyl benzamidines

Dey

Chopra

2017

CrystEngComm

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In the current study, we report the existence of 3D isostructurality behaviour in pairs of isomeric molecules existing as E-Z isomers. The polymorphic forms E1 and E2 of (E)-2-fluoro-N′-(3-phenyl) benzimidamide are individually isostructural with (E)-2-fluoro-N′-phenylbenzimidamide and (E)-2-fluoro-N′-(2fluorophenyl) benzimidamide, respectively. Furthermore, a similar compound, (Z)-3-fluoro-N′-(4fluorophenyl) benzimidamide, is isostructural with (Z)-4-fluoro-N′-(4-fluorophenyl) benzimidamide. The structural feature has been analyzed in terms of the nature and energetics of the equivalent supramolecular building blocks associated with the presence of various intermolecular interactions in the crystal packing. The crystal packing similarities have been investigated quantitatively via XPac analysis and the energy vector model. It is noteworthy to observe the presence of a rarely observed N-H⋯F interaction which plays an important role in the crystal packing of [(Z)-3-fluoro-N′-(4-fluorophenyl) benzimidamide]/[(Z)-4-fluoro-N′-(4-fluorophenyl) benzimidamide]. The NCI isosurface signifies the "attractive" nature of the N-H⋯F and N-H⋯π interactions and the different types of C-H⋯F dimeric motifs. An analysis of the two-dimensional fingerprint plots also provides a quantitative understanding of the occurrence of isostructurality in these compounds.

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Section: Introductionmentioning

confidence: 99%

Occurrence of 3D isostructurality in fluorinated phenyl benzamidines

Dey

Chopra

2017

CrystEngComm

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“…This phenomenon is typical for non-stoichiometric channel solvates [7; 8], but is not limited to non-stoichiometric solvates [9; 10; 11] nor to channel solvates [12]. The formation of isostructural solvates is typically driven by the presence of specific solventhost interactions [9; 12] or by the specific shape of the solvent molecule [7]. It is also possible to form mixed isostructural solvates, where solvent molecules can be exchanged in only a subset of the crystallographic sites [13; 14].…”

Section: Introductionmentioning

confidence: 99%

Solid-state NMR and computational investigation of solvent molecule arrangement and dynamics in isostructural solvates of droperidol

Be̅rziņš

Hodgkinson

2015

Solid State Nuclear Magnetic Resonance

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Citation for published item:frzi § sD eF nd rodgkinsonD F @PHISA 9olidEstte xw nd omputtionl investigtion of solvent moleule rrngement nd dynmis in isostruturl solvtes of droperidolF9D olid stte nuler mgneti resonneFD TS F ppF IPEPHF Further information on publisher's website: httpXGGdxFdoiForgGIHFIHITGjFssnmrFPHIRFHWFHHI Publisher's copyright statement: NOTICE: this is the author's version of a work that was accepted for publication in Solid State Nuclear Magnetic Resonance. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reected in this document. Changes may have been made to this work since it was submitted for publication. A denitive version was subsequently published in Solid State Nuclear Magnetic Resonance, 65, February 2015, 10.1016/j.ssnmr.2014.001. Additional information:Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details. 2 H NMR spectra of deuterium-labelled samples allowed the characterization of the solvent molecule dynamics in the alcohol solvates and the non-stoichiometric hydrate. The likely motion of the alcohol molecules is rapid libration within a site, plus occasional exchange into an equivalent site related by the inversion symmetry, while the water molecules are more strongly disordered. DFT calculations strongly suggest that the differences in dynamics between the solvates are related to differences in the energetic penalty for reversing the orientation of a solvent molecule.Keywords: droperidol; solid-state NMR; hydrates/solvates; isostructural solvates; solvent dynamics; spin-lattice relaxation; motional broadening; ab initio calculations Graphical abstract Highlights 15 N CP/MAS NMR clearly distinguishes ordered and dynamically disordered systems.  Spectral quality is strongly correlated to ABMS broadenings.  2 H MAS NMR provides direct insight into the nature of the solvent motion.  DFT calculations help to rationalise the differences in experimental observations.

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“…Solvates are defined as crystal structures which contain, in addition to the compound(s) of interest, molecules of the solvent of crystallization, i.e., to be a solvate, the guest must be a liquid at room temperature and pressure. 1 Solvates of organic compounds can be described as falling into one of two broad categories; 2 (1) inclusion compounds where the solvent molecules essentially act as space filling moieties and there are few or no strong interactions between the solvent and the host compound, 3 and (2) hydrogen-bonded systems where the solvent is an integral part of the structure and forms strong interactions with the host molecules. 4 Previous studies on o-acetamidobenzamide (AABA, Scheme 1) have tended to focus on its hydrogen-bonding capabilities 5,6 and solid-state transformations.…”

Section: Introductionmentioning

confidence: 99%

The solvates of o-acetamidobenzamide

2006

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A series of six solvates of o-acetamidobenzamide have been prepared and characterized by single crystal X-ray diffraction. With the exception of the chloroform solvate, five of these, the 1-propanol, 1-butanol, 2-butanol, 1,2-dichloroethane, and 1,4-dioxane solvates are isostructural with similar unit cells and atomic positions for the o-acetamidobenzamide molecules. In all cases, the solvent molecules occupy pores within the hydrogen-bonded sheets of o-acetamidobenzamide. These molecules are readily lost when the crystals are exposed to the atmosphere.

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Isostructurality among Five Solvates of Phenylbutazone

Cited by 50 publications

References 11 publications

Occurrence of 3D isostructurality in fluorinated phenyl benzamidines

Occurrence of 3D isostructurality in fluorinated phenyl benzamidines

Solid-state NMR and computational investigation of solvent molecule arrangement and dynamics in isostructural solvates of droperidol

The solvates of o-acetamidobenzamide

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