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| Item type: | Article | ||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|
| Journal or Publication Title: | Acta Crystallogr. C | ||||||||||
| Publisher: | Wiley | ||||||||||
| Volume: | 68 | ||||||||||
| Number of Issue or Book Chapter: | 6 | ||||||||||
| Page Range: | o240-o246 | ||||||||||
| Date: | 2012 | ||||||||||
| Additional Information (public): | CAN 157:478373 Crystallography and Liquid Crystals 5814-41-5 Role: PRP (Properties), RCT (Reactant), RACT (Reactant or reagent) (crystal structure of and reaction with chloroacetyl chloride); 1397284-56-8P Role: PRP (Properties), SPN (Synthetic preparation), PREP (Preparation) (crystal structure of and reaction with chloroacetyl chloride); 64262-18-6P; 1590371-33-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (in dibenzob,ediazepinone and (hydroxydibenzob,ediazepinyl){(imidazolyl)propylpiperidinyl}ethanone ethanol monosolvate crystals); 1397284-55-7P Role: PRP (Properties), SPN (Synthetic preparation), PREP (Preparation) (prepn. and crystn. from ethanol of); 90747-59-4 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of (chloroacetyl)dibenzob,ediazepinone with (imidazolyl)propylpiperidine in anhyd. acetonitrile followed by addn. of potassium carbonate); 93986-09-5P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (reaction of (chloroacetyl)dibenzob,ediazepinone with (imidazolyl)propylpiperidine in anhyd. acetonitrile followed by addn. of potassium carbonate); 79-04-9 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of dibenzob,ediazepinone chloroacetyl chloride) | ||||||||||
| Institutions: | Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical/Medicinal Chemistry II (Prof. Buschauer) | ||||||||||
| Identification Number: |
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| Keywords: | Dimers Role: PRP (Properties), SPN (Synthetic preparation), PREP (Preparation) (hydrogen-bonded in dibenzob,ediazepinone and (hydroxydibenzob,ediazepinyl){(imidazolyl)propylpiperidinyl}ethanone ethanol monosolvate crystals) Hydrogen bond (in dibenzob,ediazepinone and (hydroxydibenzob,ediazepinyl){(imidazolyl)propylpiperidinyl}ethanone ethanol monosolvate crystals) Crystal structure Molecular structure (of dibenzob,ediazepinone and (hydroxydibenzob,ediazepinyl){(imidazolyl)propylpiperidinyl}ethanone ethanol monosolvate) mol structure dibenzodiazepinone acylated deriv crystal structure dibenzodiazepinone acylated deriv hydrogen bond dimer dibenzodiazepinone acylated deriv | ||||||||||
| Dewey Decimal Classification: | 500 Science > 540 Chemistry & allied sciences | ||||||||||
| Status: | Published | ||||||||||
| Refereed: | Yes, this version has been refereed | ||||||||||
| Created at the University of Regensburg: | No | ||||||||||
| Item ID: | 32268 |
Abstract
In two dibenzodiazepinones, viz. the tricyclic core structure, 5H-dibenzob,ediazepin-11(10H)-one, C13H10N2O, and an acylated deriv., 1-(11-hydroxy-5H-dibenzob,ediazepin-5-yl)-2-{4-3-(1H-imidazol-1-yl)propylpiperidin-1-yl}ethanone EtOH monosolvate, C26H29N5O2·EtOH, dimeric assocn. via H-bond bridging between the cyclic amide entities is evident, but there are considerable differences between the ...
Abstract
In two dibenzodiazepinones, viz. the tricyclic core structure, 5H-dibenzob,ediazepin-11(10H)-one, C13H10N2O, and an acylated deriv., 1-(11-hydroxy-5H-dibenzob,ediazepin-5-yl)-2-{4-3-(1H-imidazol-1-yl)propylpiperidin-1-yl}ethanone EtOH monosolvate, C26H29N5O2·EtOH, dimeric assocn. via H-bond bridging between the cyclic amide entities is evident, but there are considerable differences between the parent compd. and the amidated deriv. Highly consistent with reported structures of related tricyclic lactams, two mols. of the nonsubstituted compd. are bridged through two N-H···O H bonds across a crystallog. center of symmetry and the bond lengths of the cyclic amide entity correspond to the amino-oxo (lactam) tautomeric form. In contrast, the structure of the deriv. shows two similar, but crystallog. unique, mols. H bonded into a dimeric unit exhibiting an approx. (noncrystallog.) C2 axis. The bond lengths of the two deriv. cyclic amide groups support their potential presence in the hydroxyimine (lactim) tautomeric forms, with the resulting possibility of intermol. tautomerism. Likely driving forces for the two extreme configurations are discussed. Crystallog. data are given. on SciFinder(R)
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