(3S,6S)-3-Isopropyl-1,4-diazabicyclo[4.4.0]decane-2,5-dione, C11H18N2O2: Bayesian statistics in data analysis

Lenstra, A. T. H.; Verbruggen, M.; Bracke, B.; Vanhouteghem, F.; Reyniers, F.; Borremans, Frans

doi:10.1107/s0108768190007868

Cited by 5 publications

(2 citation statements)

References 6 publications

(12 reference statements)

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“…Bond lengths and va lence angles agree with standard values for analo gous derivatives [12][13][14][15]. Structural disorder was expected for C6 and C7 which have the most con formational freedom.…”

Section: Resultssupporting

confidence: 74%

Structural Investigation of Two 4-AryIhexahydro-1H,3H-pyrido[1,2-c]pyrimidine-1,3-diones

Wolska

Herold

2000

Zeitschrift Für Naturforschung B

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4-A rylhexahydro-l//,3//-pyrido[l,2-c]pyrim idine-l,3-dione Derivatives, Hydrogen Bonds, Dimers The X-ray crystal structure determination o f 4-(4'-fluorophenyl)hexahydro-l//,3//-pyrido[l,2-c]pyrim idine-l,3-dione (5) and 4-(4'-chlorophenyl)hexahydro-l//,3//-pyrido [1,2-c]pyrimidine-l,3-dione (8) is reported. The crystal structures show the formation o f centrosym metric dimers via intermolecular N-H -O hydrogen bonds. The saturated ring adopts a slightly distorted sofa conformation both in 5 and in 8. In either compound the planar phenyl ring is twisted with respect to the pyrimidine-1,3-dione fragment.

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Section: Resultssupporting

confidence: 74%

Structural Investigation of Two 4-AryIhexahydro-1H,3H-pyrido[1,2-c]pyrimidine-1,3-diones

Wolska

Herold

2000

Zeitschrift Für Naturforschung B

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“…These are typically right-handed helices for l-imino residues (Pro or Pip) and have a short pitch of 6.2-6.8 Å . Chains that link OCC NHÁ Á ÁOCC NH moieties involving NH and O C groups of the same amino acid residue appear in cyclo(l-Pro-l-Phe) (9A) and the alkyl analogs cyclo(l-Pro-l-Leu) (Karle, 1972;Hendea et al, 2006), cyclo(d-Pip-l-Leu) (Symerský et al, 1987) and cyclo(l-Pip-l-Val) (Lenstra et al, 1991). These helices are typically lefthanded for l-imino acid residues (Pro or Pip) and have a pitch of 9.5-11 Å .…”

Section: Hydrogen Bonding and Molecular Packingmentioning

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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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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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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(3S,6S)-3-Isopropyl-1,4-diazabicyclo[4.4.0]decane-2,5-dione, C₁₁H₁₈N₂O₂: Bayesian statistics in data analysis

Cited by 5 publications

References 6 publications

Structural Investigation of Two 4-AryIhexahydro-1H,3H-pyrido[1,2-c]pyrimidine-1,3-diones

Structural Investigation of Two 4-AryIhexahydro-1H,3H-pyrido[1,2-c]pyrimidine-1,3-diones

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

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

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