The Crystal Structure of (3R,65)‐3‐Benzyl‐4‐Methyl‐1, 4‐Diaza‐Bicyclo [4.4.0] Decan‐2,5‐Dione

Poucke, M. Van; Lenstra, A. T. H.

doi:10.1002/bscb.19820910306

Cited by 6 publications

(1 citation statement)

References 7 publications

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“…In addition, new measurements were performed on (2B) and (9B) for which previously only the positions of heavy atoms were determined (Ramani et al, 1976;Van Poucke et al, 1982), and also on compounds (9A) and (10A), which have already been published in the literature (Budesinsky et al, 1992;Mazza et al, 1984).…”

Section: X-ray Structure Analysismentioning

confidence: 99%

Structures of cyclic dipeptides: an X-ray and computational study of cis- and trans-cyclo(Pip-Phe), cyclo(Pro-Phe) and their N-methyl derivatives

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Podlaha

et al. 2010

Acta Crystallogr Sect B

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The crystal structures of eight cyclodipeptides are determined, incorporating pipecolic acid or proline and phenylalanine or N-methyl phenylalanine. This set of structures allows the evaluation of the effects on molecular conformation and crystal packing of imino acid ring-size, relative configuration of the two amino acids, and N-methylation. In the non-methylated compounds, hydrogen-bonding interactions form one-dimensional motifs that dominate the packing arrangement. Three compounds have more than one symmetry-independent molecule in the asymmetric unit (Z' > 1), indicative of a broad and shallow molecular energy minimum. Density functional theory calculations reveal the interplay between inter- and intramolecular factors in the crystals. Only for the N-methylated compounds do simulations of the molecules in the isolated state succeed to reproduce the observed crystallographic conformations. Puckering of the diketopiperazine ring and the deviation from planarity of the amide bonds are not reproduced in the remaining compounds. Cluster in vacuo calculations with a central cyclodipeptide molecule surrounded by hydrogen-bound molecules establish that hydrogen bonding is of major importance but that other intermolecular interactions must also contribute substantially to the crystal structure. More advanced periodic calculations, incorporating the crystallographic environment to the full extent, are necessary to correctly describe all the conformational features of these cyclodipeptide crystals.

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Section: X-ray Structure Analysismentioning

confidence: 99%

Structures of cyclic dipeptides: an X-ray and computational study of cis- and trans-cyclo(Pip-Phe), cyclo(Pro-Phe) and their N-methyl derivatives

Budêšínský

Císařová

Podlaha

et al. 2010

Acta Crystallogr Sect B

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ChemInform Abstract: THE CRYSTAL STRUCTURE OF (3R,6S)‐3‐BENZYL‐4‐METHYL‐1,4‐DIAZABICYCLO(4.4.0)DECANE‐2,5‐DIONE

Poucke¹,

Lenstra²

1982

Chemischer Informationsdienst

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Bicyclic 6-6 Systems with One Ring Junction Nitrogen Atom: One Extra Heteroatom 1:0

Hermecz

Vasvári‐Debreczy

Mátyus³

1996

Comprehensive Heterocyclic Chemistry II

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The Crystal Structure of (3R,65)‐3‐Benzyl‐4‐Methyl‐1, 4‐Diaza‐Bicyclo [4.4.0] Decan‐2,5‐Dione

Abstract: The piperidine ring in the title compound is in the chair conformation, whereas the diketopiperazine ring has a boat form. The benzyl group is axially positioned and folded above the diketopiperazine ring. No dimerisation is observed.

Cited by 6 publications

References 7 publications

Structures of cyclic dipeptides: an X-ray and computational study of cis- and trans-cyclo(Pip-Phe), cyclo(Pro-Phe) and their N-methyl derivatives

Structures of cyclic dipeptides: an X-ray and computational study of cis- and trans-cyclo(Pip-Phe), cyclo(Pro-Phe) and their N-methyl derivatives

ChemInform Abstract: THE CRYSTAL STRUCTURE OF (3R,6S)‐3‐BENZYL‐4‐METHYL‐1,4‐DIAZABICYCLO(4.4.0)DECANE‐2,5‐DIONE

Bicyclic 6-6 Systems with One Ring Junction Nitrogen Atom: One Extra Heteroatom 1:0

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