Synthesis and crystal structure of 2-(2,4-dioxo-6-methylpyran-3-ylidene)-4-(4-hydroxyphenyl)-2,3,4,5-tetrahydro-1$H$-1,5-benzodiazepine

The title compound, C$_{21}$H$_{18}$N$_{2}$O$_{4}$, contains non-planar diazepine (in a boat–sofa conformation) and pyran (envelope) rings. In the crystal, O—H...O and N—H...O hydrogen bonds link the molecules, enclosing R $_{2}$ $^{2}$(16) and R $_{2}$ $^{2}$(24) ring motifs, to generate [110] chains. Very weak π–π stacking interactions between the phenyl rings of adjacent molecules with an inter-centroid distance of 4.0264 (9) Å help to consolidate a three-dimensional architecture. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (45.1%), H...O/O...H (23.2%) and H...C/C...H (19.2%) interactions.

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Publication Details

Journal
Universität Zürich, ZORA
Published
2025-04-08
DOI
https://doi.org/10.5167/uzh-290958
Primary Topic
Synthesis and pharmacology of benzodiazepine derivatives
Type
article
Field-Weighted Citation Impact
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article

Synthesis and crystal structure of 2-(2,4-dioxo-6-methylpyran-3-ylidene)-4-(4-hydroxyphenyl)-2,3,4,5-tetrahydro-1$H$-1,5-benzodiazepine

Olivier Blacque, Imane Faraj, Nada Kheira Sebbar, Lhoussaine El Ghayati et al.
Universität Zürich, ZORA
Synthesis and pharmacology of benzodiazepine derivatives
article

Synthesis and crystal structure of 2-(2,4-dioxo-6-methylpyran-3-ylidene)-4-(4-hydroxyphenyl)-2,3,4,5-tetrahydro-1$H$-1,5-benzodiazepine

Olivier Blacque, Imane Faraj, Nada Kheira Sebbar, Lhoussaine El Ghayati, El Mokhtar Essassi, Ahmed Mazzah, Tuncer Hökelek
article en

Abstract

The title compound, C$_{21}$H$_{18}$N$_{2}$O$_{4}$, contains non-planar diazepine (in a boat–sofa conformation) and pyran (envelope) rings. In the crystal, O—H...O and N—H...O hydrogen bonds link the molecules, enclosing R $_{2}$ $^{2}$(16) and R $_{2}$ $^{2}$(24) ring motifs, to generate [110] chains. Very weak π–π stacking interactions between the phenyl rings of adjacent molecules with an inter-centroid distance of 4.0264 (9) Å help to consolidate a three-dimensional architecture. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (45.1%), H...O/O...H (23.2%) and H...C/C...H (19.2%) interactions.

Universität Zürich, ZORA
Openalex Percentile: Top 31%
Synthesis and pharmacology of benzodiazepine derivatives
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Synthesis and crystal structure of 2-(2,4-dioxo-6-methylpyran-3-ylidene)-4-(4-hydroxyphenyl)-2,3,4,5-tetrahydro-1$H$-1,5-benzodiazepine — Olivier Blacque, Imane Faraj, et al. · Universität Zürich, ZORA (2025) | TGRS Research Map | TGRS